CZ401397A3 - Bicyklické aminoderiváty a antagonist PGD2, který je obsahuje - Google Patents
Bicyklické aminoderiváty a antagonist PGD2, který je obsahuje Download PDFInfo
- Publication number
- CZ401397A3 CZ401397A3 CZ974013A CZ401397A CZ401397A3 CZ 401397 A3 CZ401397 A3 CZ 401397A3 CZ 974013 A CZ974013 A CZ 974013A CZ 401397 A CZ401397 A CZ 401397A CZ 401397 A3 CZ401397 A3 CZ 401397A3
- Authority
- CZ
- Czechia
- Prior art keywords
- mhz
- chc1
- chcl
- cdcl
- hydrate
- Prior art date
Links
- 239000005557 antagonist Substances 0.000 title claims abstract description 20
- -1 Bicyclic amino derivatives Chemical class 0.000 title claims description 150
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 72
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000003814 drug Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000005905 mesyloxy group Chemical group 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000005390 cinnolyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 229940079593 drug Drugs 0.000 abstract description 6
- 210000003630 histaminocyte Anatomy 0.000 abstract description 6
- 208000006673 asthma Diseases 0.000 abstract description 5
- 206010039085 Rhinitis allergic Diseases 0.000 abstract description 4
- 201000010105 allergic rhinitis Diseases 0.000 abstract description 4
- 201000010099 disease Diseases 0.000 abstract description 4
- 230000009284 tracheal contraction Effects 0.000 abstract description 4
- 206010010744 Conjunctivitis allergic Diseases 0.000 abstract description 3
- 201000008736 Systemic mastocytosis Diseases 0.000 abstract description 3
- 208000024780 Urticaria Diseases 0.000 abstract description 3
- 208000002205 allergic conjunctivitis Diseases 0.000 abstract description 3
- 208000024998 atopic conjunctivitis Diseases 0.000 abstract description 3
- 230000004064 dysfunction Effects 0.000 abstract description 3
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 abstract description 3
- 230000010410 reperfusion Effects 0.000 abstract description 3
- 229910052708 sodium Inorganic materials 0.000 abstract description 3
- 230000009885 systemic effect Effects 0.000 abstract description 3
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 abstract description 2
- 101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 abstract description 2
- 208000027418 Wounds and injury Diseases 0.000 abstract description 2
- 230000020411 cell activation Effects 0.000 abstract description 2
- 230000006378 damage Effects 0.000 abstract description 2
- 208000035475 disorder Diseases 0.000 abstract description 2
- 208000014674 injury Diseases 0.000 abstract description 2
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 abstract description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000000302 ischemic effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 666
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 210000001772 blood platelet Anatomy 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000027455 binding Effects 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 210000003928 nasal cavity Anatomy 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002464 receptor antagonist Substances 0.000 description 3
- 229940044551 receptor antagonist Drugs 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- ABGGBXIEVBJCCD-DUMHOLGYSA-N (z)-7-[(1s,2r,3r,4r)-3-(dibenzofuran-2-ylsulfonylamino)-2-bicyclo[2.2.1]heptanyl]hept-5-enoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)N[C@@H]4[C@@H]5CC[C@@H](C5)[C@H]4C\C=C/CCCC(=O)O)=CC=C3OC2=C1 ABGGBXIEVBJCCD-DUMHOLGYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 206010057190 Respiratory tract infections Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- PWTCIBWRMQFJBC-ZEMKZVSASA-N domitroban Chemical compound N([C@H]1[C@H]2CC[C@H](C2)[C@@H]1C\C=C/CCCC(=O)O)S(=O)(=O)C1=CC=CC=C1 PWTCIBWRMQFJBC-ZEMKZVSASA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- YAWJRWLJIAFBFV-CIVIXNTOSA-N methyl (Z)-7-[(1S,2R,3R,4R)-3-(dibenzofuran-2-ylsulfonylamino)-2-bicyclo[2.2.1]heptanyl]hept-5-enoate Chemical compound C1=C(C=CC=2OC3=C(C21)C=CC=C3)S(=O)(=O)N[C@H]3[C@@H]([C@H]2CC[C@@H]3C2)CC=C/CCCC(=O)OC YAWJRWLJIAFBFV-CIVIXNTOSA-N 0.000 description 2
- NMLYCAZKJKGWMR-BSTDHMEGSA-N methyl (Z)-7-[(1S,2R,3R,4R)-3-amino-2-bicyclo[2.2.1]heptanyl]hept-5-enoate Chemical compound C1C[C@]2([H])[C@@H](C\C=C/CCCC(=O)OC)[C@H](N)[C@@]1([H])C2 NMLYCAZKJKGWMR-BSTDHMEGSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000004323 oxepin-2-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C(*)O1 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 210000005259 peripheral blood Anatomy 0.000 description 2
- 239000011886 peripheral blood Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 210000004623 platelet-rich plasma Anatomy 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 230000002685 pulmonary effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 210000003437 trachea Anatomy 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 1
- OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical group CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- APIXJSLKIYYUKG-UHFFFAOYSA-N 3 Isobutyl 1 methylxanthine Chemical compound O=C1N(C)C(=O)N(CC(C)C)C2=C1N=CN2 APIXJSLKIYYUKG-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 1
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004229 4H-chromen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(OC(*)=C([H])C2([H])[H])=C1[H] 0.000 description 1
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
- FYVMIBRAJOMHGZ-UHFFFAOYSA-N 6-(3-amino-2-bicyclo[2.2.1]heptanyl)hex-5-enoic acid Chemical compound C1CC2C(C=CCCCC(O)=O)C(N)C1C2 FYVMIBRAJOMHGZ-UHFFFAOYSA-N 0.000 description 1
- UKZROAVOALUTST-UHFFFAOYSA-N 7-(3-amino-2-bicyclo[2.2.1]heptanyl)hept-5-enoic acid Chemical compound C1CC2C(CC=CCCCC(O)=O)C(N)C1C2 UKZROAVOALUTST-UHFFFAOYSA-N 0.000 description 1
- UKXLPCGOHBVAOS-UHFFFAOYSA-N 7-(3-amino-2-bicyclo[2.2.1]heptanyl)heptanoic acid Chemical compound C1CC2C(N)C(CCCCCCC(O)=O)C1C2 UKXLPCGOHBVAOS-UHFFFAOYSA-N 0.000 description 1
- PYBRYBRGGCBFPJ-UHFFFAOYSA-N 7-(4-amino-6,6-dimethyl-3-bicyclo[3.1.1]heptanyl)hept-5-enoic acid Chemical compound C1C2C(C)(C)C1CC(CC=CCCCC(O)=O)C2N PYBRYBRGGCBFPJ-UHFFFAOYSA-N 0.000 description 1
- DNGUEWLQENWEDJ-UHFFFAOYSA-N 7-[3-(methylamino)-2-bicyclo[2.2.1]heptanyl]hept-5-enoic acid Chemical compound C1CC2C(CC=CCCCC(O)=O)C(NC)C1C2 DNGUEWLQENWEDJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010027654 Allergic conditions Diseases 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IVSAJJSQPNMZJU-UHFFFAOYSA-L C(CCCC=CC)(=O)[O-].[Ca+2].C(CCCC=CC)(=O)[O-] Chemical compound C(CCCC=CC)(=O)[O-].[Ca+2].C(CCCC=CC)(=O)[O-] IVSAJJSQPNMZJU-UHFFFAOYSA-L 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241001631457 Cannula Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101100511454 Epichloe uncinata lolO1 gene Proteins 0.000 description 1
- 101100511455 Epichloe uncinata lolO2 gene Proteins 0.000 description 1
- CTKXFMQHOOWWEB-UHFFFAOYSA-N Ethylene oxide/propylene oxide copolymer Chemical compound CCCOC(C)COCCO CTKXFMQHOOWWEB-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ONKJLIUSEXIAKL-UHFFFAOYSA-N Garamine Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(O)C(N)CC1N ONKJLIUSEXIAKL-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 208000035268 Mast Cell Activation disease Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005277 alkyl imino group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- YCSBALJAGZKWFF-UHFFFAOYSA-N anthracen-2-amine Chemical compound C1=CC=CC2=CC3=CC(N)=CC=C3C=C21 YCSBALJAGZKWFF-UHFFFAOYSA-N 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 229950008138 carmellose Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- ULCKEERECJMLHP-UHFFFAOYSA-N dibenzofuran-2-sulfonyl chloride Chemical compound C1=CC=C2C3=CC(S(=O)(=O)Cl)=CC=C3OC2=C1 ULCKEERECJMLHP-UHFFFAOYSA-N 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 125000005049 dihydrooxadiazolyl group Chemical group O1N(NC=C1)* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- ONKJLIUSEXIAKL-QUDADGMASA-N garamine Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](N)C[C@H]1N ONKJLIUSEXIAKL-QUDADGMASA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KPSZWAJWFMFMFF-UHFFFAOYSA-N hept-5-enoic acid Chemical compound CC=CCCCC(O)=O KPSZWAJWFMFMFF-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 208000037906 ischaemic injury Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 239000006390 lc 2 Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- BZLKUBLVRNYSBG-DHMWGJHJSA-N n-[(1r,2s,3s,4s)-2-(2-oxoethyl)-3-bicyclo[2.2.1]heptanyl]benzenesulfonamide Chemical compound N([C@H]1[C@@]2([H])CC[C@](C2)([C@@H]1CC=O)[H])S(=O)(=O)C1=CC=CC=C1 BZLKUBLVRNYSBG-DHMWGJHJSA-N 0.000 description 1
- FKJARBPQBIATJT-UHFFFAOYSA-N n-benzyl-n-phenylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)C1=CC=CC=C1 FKJARBPQBIATJT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical compound CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000006218 nasal suppository Substances 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229940044519 poloxamer 188 Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/74—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/84—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/54—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
- C07C281/14—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/43—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C337/06—Compounds containing any of the groups, e.g. thiosemicarbazides
- C07C337/08—Compounds containing any of the groups, e.g. thiosemicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. thiosemicarbazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/20—[b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/14—[b,f]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/24—[b,e]-condensed with two six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/14—[b,f]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
- C07F9/5355—Phosphoranes containing the structure P=N-
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Vynález se týká bicyklických aminoderivátů a antagonistů prostaglandinu D2 (dále uváděný jako PDG2), který j e obsahuj e.
Dosavadní stav techniky
Některé bicyklické aminoderiváty podle -vynálezu jsou známé jako užitečné antagonisty tromboxanu A2 (TXA2) (Japonská patentová publikace (KOKOKU) č. 79060/1993). Avšak Japonská patentová publikace (KOKOKU) č. 79060/1993 pouze uvádí, že sloučeniny jsou užitečné jako antagonist TXA2 a neuvádí jejich užitečnost jako antagonist PDG2 jak je uvedeno v této přihlášce vynálezu.
Je známo, že TXA2 je účinný proti shlukování destiček, trombogenézi atd. Antagonist TXA2 je proto považován za užitečné antitrombotické činidlo a také při léčbě infarktu myokardu nebo astmatu antagonizací TXA2.
Na druhé straně, antagonist PDG2 podle vynálezu je užitečný ke zlepšení stavů způsobených nadbytečnou produkcí PDG2. Zejména je užitečný jako léčivo pro léčbu nemocí způsobených disfunkcí žírné buňky, například systemické mastocytózy a poruch aktivace systemické žírné buňky a také tracheální kontrakce, astmatu, alergické rinitidy, alergické konjuktivitidy, kopřivky, poranění následkem ischemické . reperfuze a zánětu.
Jak je zřejmé ze shora uvedeného, antagonist TXA2 a antagonist PDG2 jsou zcela navzájem odlišné v místě působení, mechanizmu účinku a aplikaci a mají zcela různé vlastnosti.
Podle toho nemohlo být očekáváno, že jakákoliv sloučenina • · · bude vykazovat tyto účinky současně.
PDG2 se připravuje přes PGG2 a PGH2 z kyseliny arachidonové působením cyklooxygenázy aktivované imunologickou nebo neimunologickou stimulací a je hlavní produkt, který je produkován a uvolňován z žírných buněk. PGD2 má různě silné fyziologické a patologické účinky. Například PDG2 může způsobit silnou tracheální kontrakci, která vede k bronchiálnímu astmatu a v systemickém alergickém stavu může rozšiřovat periferní cévy, což vede k anafylaktickému šoku. Zejména, zvláštní pozornost je věnována myšlence, že PDG2 je jedna ze základních substancí, které způsobuj í počátek nazální okluze při alergické rinitidě. Proto bylo navrženo vyvinout inhibitor proti biosyntéze PDG2 nebo antagonist receptoru PDG2 jako léčivo pro snížení nazální okluze. Avšak inhibitor biosyntézy PDG2 zvyšuje syntézu prostaglandinů v jiných organismech a je proto žádoucí vyvinout antagonist (blokátor) specifický vůči receptoru PDG2.
Podstata vynálezu
Vynálezci studovali intenzivně vývoj antagonistů receptoru PDG2 (blokátory) specifických vůči receptoru PDG2 a zjistili, že sloučenina obecného vzorce I uvedená dále a její sůl vykazují silnou účinnost jako antagonist receptoru PDG2 a jsou chemicky stabilní.
Vynález se týká antagonistů PDG2, který zahrnuje jako aktivní složku sloučeninu obecného vzorce I uvedený dále nebo její sůl nebo hydrát
kde
znamená
A je alkylenová skupina, která je případně přerušena heteroatomem nebo fenylenem a obsahuje oxoskupinu a/nebo nenasycenou vazbu;
B je vodík, alkyl, aralkyl nebo acyl,R je skupina COORj, CH2OR2 nebo CON(R3)(R4);
je vodík nebo alkyl;
R2 je vodík nebo alkyl;
R3 a R4 jsou nezávisle vodík, alkyl, hydroxyskupina nebo alkylsulfonyl;
X^ je jednoduchá vazba, fenylen, naftylen, thiofendiyl, indoldiyl nebo oxazoldiyl ,X2 je jednoduchá vazba, skupina -N=N-, -N=CH-, -CH=N-N-,
-CH=N-O-,-C=NNHCSNH-, -C=NNHCONH-, -CH=CH~, -CH(OH)-,
-C(C1)=C(C1)-, -(CH2)n-, ethinylen, -N(Rg)-, -N(R51)CO-, -n(r52)so2~, -n(r53)Concr54)-, -conír55)-, -so2n(r56)-, -0-,
-S-, -S0-, -S02-, -C0-, oxadiazoldiyl, thiadiazoldiyl, tetrazoldiyl;
X3 je alkyl, alkenyl, alkinyl, aryl, aralkyl, heterocyklická skupina, cykloalkyl, cykloalkenyl, thiazolinylidenmethyl, tiazolidinylidenmethyl, -CH=NRg nebo -N=C(R7)Rg,R5' R51' R52' R53' R54 a R55 znamenajr každý vodík nebo alkyl;
Rg ίθ vodík, alkyl, hydoxyskupina, alkoxyskupina, karbamoyloxyskupina, thiokarbamoyloxyskupina, ureidoskupina nebo thioureidoskupina;
R7 a Rg znamenají každý nezávisle alkyl, alkoxyskupinu nebo aryl ;
n je 1 nebo 2;
Z je skupina -S02- nebo -CO- a m je 0 nebo 1, kde cyklický subsituent může obsahovat jeden až tři substituenty vybrané ze souboru, který zahrnuje nitroskupinu, alkoxyskupinu, sulfamoylovou skupinu, substituovanou nebo nesubstituovanou aminoskupinu, acylskupinu, acyloxyskupinu, hydroxyskupinu, halogen, alkyl, alkinyl, karboxyskupinu, alkoxykarbonyl, aralkoxykarbonyl, aryloxykarbonyl, mesyloxyskupinu, kyanoskupinu, alkenyloxyskupinu, hydroxyalkyl, trifluormethyl, alkylthioskupinu, skupinu -N=PPh3, oxoskupinu, thioxoskupinu, hydroxyiminoskupinu, alkoxyiminoskupinu, fenyl a alkylendioxyskupinu.
Specifické příklady sloučenin vhodných jako antagonist PDG2 shora zahrnují sloučeninu obecného vzorce I, kde • · • · ·
9 9
Je
m je 0; a kde Z je SO2, obě X-^ a X2 jsou jednoduchá vazba,- X je alkyl, fenyl, naftyl, styryl, chinolyl a thienyl; a cyklický substituent obsahuje případně jeden až tři substituenty vybrané ze souboru, který zahrnuje nitroskupinu, alkoxyskupinu, substituovanou nebo nesubstituovanou aminoskupinu, halogen, alkyl a hydroxyalkyl nebo její sůl nebo hydrát.
Podobně, specifické příklady zahrnují sloučeninu obecného vzorce I, kde je kde m je 1, obě X^ a X2 jsou jednoduchá vazba; a X3 je fenyl, případně substituovaný halogenem nebo její sůl nebo hydrát.
Podobně specifické příklady zahrnuji sloučeninu obecného vzorce I, kde ······ ·· · ·· ·· • · < · · c · · ·· · • · · · · · · · ····9
9 9 9 9 9 9 9 99
99 9 9 999 9 99 9
kde m je 1, X-^ je fenyl, X2 je -CH2- nebo -N-N- a X3 je fenyl nebo její sůl nebo hydrát.
Podobně, příklady sloučenin obecného vzorce I zahrnují ty sloučeniny obecného vzorce Ia
(Ia) kde A, B, R, X-^, X2 a X3 jsou jak definováno shora nebo jejich sůl nebo hydrát s tím, že nejsou zahrnuty ty sloučeniny, kde (1) X-j^ a X2 znamenají jednoduchou vazbu a X3 je substituovaný nebo nesubstituovaný fenyl nebo naftyl;
a (2) A je 5-heptenylen, R je COOR-^ (R-j_ je vodík nebo methyl), X^ je 1,4-fenylen, X2 je jednoduchá vazba a X3 je fenyl.
Podobně, příklady sloučenin obecného vzorce I zahrnují ty sloučeniny obecného vzorce Ib (Ib)
kde je
nebo
A, B, R, Xlz X2 a X^ mají význam definovaný shora nebo jejich sůl nebo hydrát, s tím, že nejsou zahrnuty ty sloučeniny, kde X-^ a X2 znamenají jednoduchou vazbu a X3 je fenyl a kde X-^ je jednoduchá vazba a X2 je -O- a X3 je benzyl.
Specifičtěji, příklady sloučenin obecného vzorce I zahrnují ty sloučeniny obecného vzorce Ia, kde Xj a X2 znamenají jednoduchou vazbu, X^ je isoxazolyl, thiadiazolyl, isothiazolyl, morfolyl, indolyl, benzofuryl, dibenzofuryl, dibenzodioxinyl, benzothienyl, dibenzothienyl, karbazolyl, xanthenyl, fenantridinyl, dibenzoxepinyl, dibenzothiepinyl, cinnolyl, chromeny!, benzimidazolyl nebo dihydrobenzothiepinyl nebo jejich sůl nebo hydrát.
Podobně, příklady sloučenin obecného vzorce I zahrnují ty sloučeniny obecného vzorce Ia, kde X·] je jednoduchá vazba, • · · ® • 9 ·
X2 je fenylen, X3 je alkenyl, alkinyl, -CH-NRg nebo
-N=C(Ry)Rg nebo jejich sůl nebo hydrát.
Podobně, příklady sloučenin obecného vzorce I zahrnují ty sloučeniny obecného vzorce la, kde R je COOR^, X^ je fenylen nebo thiofendiyl, X2 je jednoduchá vazba, -N-N-, -CH=CH-, -CONH-, -NHCO- nebo ethynilen a X3 je fenyl, thiazolinylidenmethyl, thiazolidinylidenmethyl nebo thienyl nebo jejich sůl nebo hydrát.
Specifičtěji, příklady sloučeniny obecného vzorce I zahrnují ty sloučeniny obecného vzorce lb, kde
nebo jejich sůl nebo hydrát. Příklady specifičtějších sloučenin zahrnují ty sloučeniny obecného vzorce lb, kde R je COOR^ (Rj má význam uvedený shora) nebo jejich sůl nebo hydrát.
Podobně, příklady sloučeniny obecného vzorce I zahrnují ty sloučeniny obecného vzorce lb, kde X je fenylen nebo thiofendiyl, X2 je jednoduchá vazba, -N=N-, -CH=CH-, ethinylen, -0-, -S-, -CO-, -C0N(R55)-, (R55 má význam definovaný shora),
-N(R51)C0- (R51 má význam definovaný shora) a X3 je fenyl nebo její sůl nebo hydrát.
Specifičtěji, příklady sloučeniny obecného vzorce I «····· ·« · ·· · · • · · 9 9 99 9 9 9 · zahrnuji ty sloučeniny obecného vzorce lb, kde • · · · · · · · · · · 9* ······· 9 99
9 9 9 9 9 9 9 9 9 9«Τ*
je
nebo jejich sůl nebo hydrát. Příklady výhodnějších sloučenin zahrnují ty sloučeniny, kde B je vodík, obě X-^ a X2 znamenají jednoduchou vazbu, X3 je thiehyl, thiazolyl, thiadiazolyl, isothiazolyl, pyrrolyl, pyridyl, benzofuryl, benzimidazolyl, benzothienyl, dibenzofuryl, chinolyl nebo indolyl nebo jejich sůl nebo hydrát. Podobně, příklady zahrnují ty sloučeniny, kde je fenylen, thiofendiyl, indoldiyl nebo oxazoldiyl, X2 je jednoduchá vazba, -N=N~, -CH=CH-, ethinylen, -S- nebo -O- a Xg je aryl nebo heterocyklická skupina nebo jejich sůl nebo hydrát.
Sloučeniny obecného vzorce Ia a lb jsou nové sloučeniny, které připravili autoři vynálezu.
Termíny použité v popise mají význam uvedený dále.
Termín alkylen znamená alkylenový řetězec, přímý nebo rozvětvený s 1 až 9 atomy uhlíku, například methylen, methylmethylen, dimethylmethylen, methylethylmethylen, ethylen, trimethylen, tetramethylen, pentamethylen, hexamethylen, heptamethylen, oktamethylen, nonamethylen nebo pod. Alkylen uvedený shora může být přerušen heteroatomem nebo heteroatomy (atomy kyslíku, síry, dusíku nebo pod.) nebo fenylenem (např. 1,4-fenylen, 1,3-fenylen, 1,2-fenylen nebo pod.), obsahuje oxoskupinua/nebo má jednu nebo více dvojných nebo trojných vazeb v kterékoliv poloze řetězce. Příklady zahrnují -(CH2)2-O-CH2-, -(CH2)2-0-(CH2)2-, -(ch2)2-o-(ch2)3-, -(ch2)2-o-(ch2)4-, -(ch2)2-o-(ch2)5-( -(ch2)2-0-(CH2)6-, -(CH2)2-s-(CH)2-, -(ch2)3-s-<ch2)2-, -ch2-s-ch2-, -ch2-s- (CH2)4-, -CH2-N(CH3)-ch2-,
-CH2~NH-(CH2)2-, -(CH2)2-N(CH2CH3)-(CH2)3-,
-(CH2)2~1,4-fenylen-CH2~, -(CH2)2-O-l,3-fenylen-CH2-,
- (CH2) 2 -0-1, 2 - f enylen-CH2 -, - (CH2) 2-O-1,4- f enylen- CII2 - , -CH=CH-S-CH2-1,4-fenylen-CH2-, -CH=CH-S-1,3-fenylen-(CH2)2-,
2- oxopropylen, 3-oxopentylen, 5-oxohexylen, vinylen,
1-propenylen, 2-propenylen, 1-butenylen, 2-butenylen,
3- butenylen, 1,2-butadienylen, 1,3-butadiénylen,
1- pentenylen, 2-pentenylen, 3-pentenylen, 4-pentenylen,
1.2- pentadienylen, 1,3-pentadienylen, 1,4-pentadienylen,
2.3- pentadienylen, 2,4-pentadienylen, 1-hexenylen,
2- hexenylen, 3-hexenylen, 4-hexenylen, 5-hexenylen,
1,2-hexadienylen,
1.5- hexadienylen,
2.5- hexadienylen,
1.3- hexadienylen,
2.3- hexadienylen,
3.4- hexadienylen,
1.4- hexadienylen,
2.4- hexadienylen,
3.5- hexadienylen,
4,5-hexadienylen,
1,1-dimethyl-4-hexenylen, 1-heptenylen,
2-heptenylen, 3-heptenylen, 4-heptenylen, 5-héptenylen,
2,2-dimethyl-5-heptenylen, 6-heptenylen, 1,2-heptadienylen,
1,3 - hep t ad i enyl en,
1,4-heptadienylen,
2,3-heptadienylen,
2.6- heptadienylen,
3.6- heptadienylen,
1,5-heptadienylen,
2.4- heptadienylen,
3.4- heptadienylen,
4.5- heptadienylen,
1-propinylen,
1,6-heptadienylen,
2.5- heptadienylen,
3.5- heptadienylen,
4.6- heptadienylen, 5,6-heptadienylen,
3-butinylen, 2-pentinylen, 5-hexinylen, 6-heptinylen,
-(CH2)-ch=ch-o-(ch2)2-, -ch2-s-(ch2)3-,
-CH2-cis-CH=CH-l,2-fenylen-CH2-, -CH=CH-1,4-fenylen-(CH2)2~, -4-OXO-4,5-hexenylen- apod.
Termín alkyl znamená přímý nebo rozvětvený alkyl s 1 až 20 atomy uhlíku, jako je například methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sek.butyl, terc.butyl, n-pentyl, i-pentyl, neopentyl, terc.pentyl, hexyl, heptyl, oktyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, oktadecyl, nonadecyl, ikosyl a pod.
Termín aryl znamená monocyklický nebo kondenzovaný kruh se 6 až 14 atomy uhlíku, například fenyl, naftyl (například 1-naftyl, 2-naftyl) anthryl (například 1-anthryl,
2- anthryl, 9-anthryl), fenanthry1 (například 2-fenanthry1,
3- fenanthryl, 9-fenanthryl), fluorenyl (například
2- fluorenyl) apod. Zvlášť výhodný je fenyl.
Termín aralkyl znamená skupinu vzniklou substitucí alkylu jak je definován shora arylem v kterékoliv substituovalné poloze alkylu. Příklady zahrnují benzyl, fenethyl, fenylpropyl (například 3-fenylpropyl), naftylmethyl (například oi-naftylmethyl) , anthrylmethyl (například
9-anthrylmethyl), fenanthrylmethyl (například
3- fenanthrylmethyl) apod.
Termín acyl znamená acyl odvozený od alifatické karboxylové kyseliny obsahující 1 až 9 atomů uhlíku, například formyl, acetyl, propionyl, butyryl, valeryl a pod.
Termín alkylsulfonyl znamená skupinu vzniklou substitucí sulfonylu alkylem uvedeným shora, například methylsulfonyl, ethylsulfonyl, propylsulfonyl a pod.
Termín alkenyl znamená alkenyl s přímým nebo rozvětveným řetězcem se 2 až 20 atomy uhlíku, který odpovídá alkylu uvedeném shora obsahující jednu nebo více dvojných vazeb. .Příklady zahrnují vinyl, 1-propenyl, 2-propenyl,
1-butenyl, 2-butenyl, 3-butenyl, 1,2-butadienyl, 1-pentenyl,
1,2-pentadienyl, 2-hexenyl, 1,2-hexadienyl, 3-heptenyl, * *
1,5-heptadienyl apod.
Termín alkinyl znamená alkinyl s přímým nebo rozvětveným řetězcem se 2 až 20 atomy uhlíku, který odpovídá alkylu uvedeném shora obsahující jednu nebo více trojných vazeb. Příklady zahrnují ethinyl, 1-propinyl, 2-butinyl,
3-butinyl apod.
Termín heterocyklická skupina znamená 5 až 7 člennou cyklickou skupinu obsahující jeden nebo více heteroatomů vybraných nezávisle ze skupiny, která zahrnuje atom kyslíku, síry a/nebo dusíku v kruhu a je případně kondenzována s uhlíkatým kruhem nebo jinou heterocyklickou skupinou v kterékoliv substituovatelné poloze. Příklady zahrnují pyrrolyl (například 1-pyrrolyl, 3-pyrrolyl), indolyl (například 2-indolyl, 3-indolyl, 6-indolyl), karbazolyl (například 2-karbazolyl, 3-karbazolyl), imidazolyl (například 1-imidazolyl, 4-imidazolyl), pyrazolyl (například
1- pyrazolyl, 3-pyrazolyl), benzimidazolyl (například
2- benzimidazolyl, 5-benzimidazolyl), indazolyl (například
3- indazolyl), indolizinyl (například 6-indolyzinyl), pyridyl (například 2-pyridyl, 3-pyridyl, 4-pyridyl), chinolyl (například 8-chinolyl), isochinolyl (například
3- isochinolyl), akridyl (například 1-akridyl), fenanthrydinyl (například 2-fenanthrydinyl, 3-fenanthrydinyl), pyridazinyl (například 3-pyridazinyl), pyrimidinyl (například
4- pyrimidinyl), pyrazinyl (například 2-pyrazinyl), cinnolinyl (například 3-cinnolinyl), ftaladinyl (například
5- ftaladinyl), chinazolinyl (například 2-chinazolinyl), isoxazolyl (například 3-isoxazolyl, 4-isoxazolyl), benzisoxazolyl (například 1,2-benzisoxazol-4-yl),
2,l-benzisoxazol-3-yl), oxazolyl (například 2-oxazolyl,
4-oxazolyl, 5-oxazolyl), benzoxazolyl (například 2-benzoxazolyl), benzoxadiazolyl (například
4-benzoxadiazolyl), isothiazolyl (například 3-isothiazolyl),
4-isothiazolyl), benzisothiazolyl (například
1.2- benzisothiazol-3-yl, 2,l-benzisothiazol-5-yl), thiazolyl (například 2-thiazolyl), benzothiazolyl (například
2- benzothiazolyl), thiadiazolyl (například 1,2,3-thiadiazol-
4-yl), oxadiazolyl (například 1,3,4-oxadiazol-2-yl), dihydrooxadiazolyl (například 4,5-dihydro-1,2,4-oxadiazol-3-yl), furyl (například 2-furyl, 3-furyl), benzofuryl (například
3- benzofuryl), isobenzofuryl (například 1-isobenzofuryl), thienyl (například (2-thienyl, 3-thienyl), benzothienyl (například l-benzothiofen-2-yl, 2-benzothiofen-l-yl), tetrazolyl (například 5-tetrazolyl), benzodioxolyl (například
1.3- benzodioxol-5-yl), dibenzofuryl (například
2-dibenzofuryl, 3-dibenzofuryl), dibenzoxepinyl (například dibenz[b,f]oxepin-2-yl, dihydrodibenzoxepinyl (například dihydrodibenz[b,f]oxepin-2-yl, chromenyl (například 2H-chrpmen-3-yl, 4H-chromen-2-yl), dibenzothiepinyl (například dibenzo[b,f1thiepin-3-yl, dihydrodibenzo[b,f]thiepin-3-yl, morfolinyl (například 1,4-morfolin-4-yl), fenothiadinyl (2-fenothiadinyl), cyklopentathienyl (například cyklopenta[b]thiofen-3-yl) apod.
Termín cykloalkyl znamená cyklický alkyl se 3 až 8 atomy uhlíku, například cyklopropyl, cyklobutyl, cyklopentyl, cyklohexyl apod.
Termín cykloalkenyl znamená cyklický alkenyl se 3 až atomy uhlíku, například cyklopropenyl (například 1-cyklopropenyl), cyklobutenyl (například 2-cyklobuten-l-yl), cyklopentenyl (1-cyklopenten-l-yl), cyklohexenyl (1-cyklohexen-l-yl) apod.
Termín alkoxyskupina znamená alkoxyskupinu s 1 až 6 atomy uhlíku, například methoxyskupinu, ethoxyskupinu, n-propoxyskupinu, i-propoxyskupinu, n-butoxyskupinu apod.
Příklad substituované aminoskupiny v definici substituovaná nebo nesubstituovaná aminoskupina zahrnuje mono nebo disubstituovanou aminoskupinu, jako je methylaminóskupina, ethylaminoskupina, dimethylaminoskupina, cyklohexy1aminoskupina, fenylaminoskupina, difenylaminoskupina nebo cyklická aminoskupina, jako je piperidinoskupina, piperazinoskupina nebo morfolinoskupina.
Termín acyloxyskupina znamená acyloxyskupinu
Odvozenou od acylu uvedeném shora, například acetyloxyskupinu, propionyloxyskupinu, butyryloxyskupinu, valeryloxyskupinu apod.
Termín halogen znamená fluor, chlor, brom a jod.
Termín alkoxykarbonyl znamená alkoxykarbonylovou skupinu odvozenou od alkoxyskupiny uvedené shora, například methoxykarbonyl, ethoxykarbonyl, fenyloxykarbonyl apod.
Termín aralkyloxykarbonyl znamená aralkyloxykarbonylovou skupinu odvozenou od aralkylu uvedeném shora, například benzyloxykarbonyl, fene thyloxykarbonyl apod.
Termín aryloxykarbonyl znamená skupinu odvozenou od arylu” uvedeném shora, například fenyloxykarbonyl, naf tyloxykarbonyl apod.
Termín alkenyloxyskupina znamená alkenyloxyskupinu odvozenou od alkenylu uvedeném shora, například vinyloxyskupinu, 1-propenyloxyskupinu, 2-butenyloxyskupinu apod.
Termín hydroxyalkyl znamená hydroxyalkylovou skupinu odvozenou od alkylu uvedeném shora, například hydroxymethyl, hydroxyethyl, hydroxypropyl apod.
Termín alkylthioskupina znamená alkylthioskupinu ··♦· ·· φ· φ φφ φφ' • · · φ ♦ φ · φ « φ φ
9 9 9 9 9 9 999
ΦΦ ΦΦΦ φ φ φ Φφφφ φ
9 9 9 9 9 9 9 99
9 9 9 9 9 9 99 9 99 9 odvozenou od alkylu uvedeném shora, například methylthioskupinu, ethylthioskupinu, propylthioskupinu apod.
Termín ”alkylendioxyskupina znamená alkylendioxyskupinu s 1 až 3 atomy uhlíku, například methylendioxyskupinu, ethylendioxyskupinu, propylendioxyskupinu apod.
V případě fenylenu, naftylenu, thiofendiylu, indoldiylu, oxazoldiylu, oxadiazoldiylu a tetrazoldiylu může být uvedená skupina vázána k sousedním skupinám v kterékoliv ze dvou substituovatelných místech.
V definicích uvedených shora, pokud je substituent cyklický, může být substituován jedním až třemi substituenty vybrané ze souboru který zahrnuje nitroskupiny, alkoxyskupiny, sulfaomoylové skupiny, substituované nebo nesubstituované aminoskupiny, acyly, acyloxyskupiny, hydroxyskupiny, atomy halogenu, alkyly, alkinyly, karboxyskupiny, alkoxylkarbonyly, aralkoxykarbonyly, aryloxykarbonyly, mesyloxyskupiny, kyanoskupiny, alkenyloxyskupiny, hydroxyalkyly, trifluormethyly, alkylthioskupiny, skupiny N=PPh-j, oxoskupiny, thioxoskupiny, hydroxyiminoskupiny, alkyliminoskupiny, fenyly a alkylendioxyskupiny. Substituenty mohou být vázány k jakékoliv substituovatelné poloze kruhu.
Příklady solí sloučeniny obecného vzorce I zahrnují soli tvořené s alkalickým kovem (například lithium, sodík nebo draslík), kovem alkalických zemin (například vápník), organickou bází (například tromethamin, trimethylamin, triethylamin, 2-aminobutan, terč.butylamin, diisopropylethylamin, n-butylmethylamin, cyklohexylamin, dicyklohexylamin, N-isopropylcyklohexylamin, furfurylamin, benzylamin, methylbenzylamin, dibenzylamin, N,N-dimethylbenzylamin, 2 -chlorbenzylamin,
• •4» | • 4 | 4« | 4 | 44 | 4 4 | ||
• | • 4 | 4 | 4 | 4 4 | • 4 | 4 | 4 |
4 | 4 4 | 4 4 | • | • 4 | 4 4 | ||
• | 4 4 · | 4 4 | 4 | 4 444 | 4 | 4 | |
• 4 | 4 4 | 4 | • | 4 | 4 | 4 | 4 |
4-methoxybenzylamin, 1-naftylenmethylamin, difenylbenzylamin, trifenylamin, 1-naftylamin, 1-aminoantracen, 2-aminoantracen, dehydroabietylamin, N-methylmorfolin nebo pyridin), aminokyselinami (například lysin nebo arginin) apod.
Termín hydrát znamená hydrát sloučeniny obecného vzorce I nebo její soli. Příklady zahrnují mono a dihydráty.
Sloučeniny podle vynálezu jsou představovány obecným vzorcem I a zahrnují rovněž formu nebo jakýkoliv typ stereoisomeru (například diastereomer, epimer, enantiomer) a racemické sloučeniny.
Ze sloučenin obecného vzorce I jsou ty sloučeniny, kde m=l, zejména ty, které jsou uvedeny v Tabulkách 3b a 3c dále známé sloučeniny a jsou popsány v Japonské patentové publikaci (KOKAI) č. 180862/1990.
Ze sloučenin obecného vzorce I se ty sloučeniny, kde m=0 [tj . sloučeniny představované obecným vzorcem I'] mohou připravit reakcí aminosloučeniny obecného vzorce II s reaktivním derivátem sulfonové kyseliny nebo karboxylové kyseliny odpovídající parciální struktuře Z-X1~X2“X3» jak je uvedeno dále.
(n
Kde A, B, R, Χχ, X2, X3,
Y a Z maj í význam uvedený shora.
• · · · • · · • · · ·♦· · 9
9 9
Kyselina sulfonová, odpovídající parciální struktuře
Z-X1-X2~x3 j® sloučenina obecného vzorce X3~X2-Xi-SO2OH a karboxylová kyselina odpovídající uvedené parciální struktuře je sloučenina obecného vzorce X3-X2-X1-COOH. Reaktivní derivát této sulfonové nebo karboxylové kyseliny znamená odpovídající halogenid (například chlorid, bromid, jodid), anhydrid kyseliny (například směsný anhydrid s kyselinou mravenčí nebo kyselinou octovou), aktivní ester (například sukcinimidester) a příklady obvykle zahrnují acylační činidla pro acylaci aminoskupiny. Karboxylová kyselina X3-X2-X1_C®OH se může použít při reakci bez přeměny na reaktivní derivát, v přítomnosti kondenzačního činidla (například dicyklohexylkarbodíimidu (DCC), 1-ethyl-3-(3-dimethylaminopropyl)karbodiimidu, N,N'-karbonyIdiimidazolu), které se použijí při kondenzační reakci mezi aminem a karboxy!ovou kyselinou.
Reakce se provádí při podmínkách obvykle užívaných pro acylaci aminoskupiny. Například v případě kondenzace užívající acidhalogenid se reakce provede za použití rozpouštědla, jako je etherové rozpouštědlo (například diethylether, tetrahydrofuran, dioxan), benzenové rozpouštědlo (například benzen, toluen, xylen), halogenované uhlovodíkové rozpouštědlo (například dichlormethan, dichlorethan, chloroform), ethylacetát, dimethylformamid, dimethylsulfoxid, acetonitril nebo pod, je-li to nezbytné, v přítomnosti báze (například organická báze jako je triethylamin, pyridin, N,N-dimethylaminopyridin, N-methylmorfolin; anorganická báze, jako je hydroxid sodný, hydroxid draselný, uhličitan draselný nebo pod.) za chlazení, při teplotě místnosti nebo při zahřívání, výhodně při teplotě od -20 °C do teploty za chlazení nebo od teploty místnosti do teploty refluxu reakčního systému, po několik minut nebo několik hodin, výhodně po dobu 0,5 až 24 hodin, výhodněji po dobu 1 hodiny až 12 hodin.
Reakční podmínky pro reakci mezi jiným reaktivním • 4 · · · · • · • · · derivátem nebo volnou kyselinou a aminem II se stanoví konvenčním způsobem v závislosti na vlastnostech reaktivního derivátu nebo volné kyseliny.
Reakční produkt se čistí obvyklými čistícími způsoby, například extrakcí rozpouštědlem, chromatografií, rekrystalizácí nebo pod.
Specifické příklady sloučenin obecného vzorce II jako výchozího materiálu pro způsob podle vynálezu jsou následuj ící. Příklady 3-amino[2.2.1]byciklické sloučeniny zahrnuj í 7-(3-aminobicyklo[2.2.1]hept-2-yl)-5-heptenovou kyselinu, 7-(3-aminobicyklo[2.2.1]hept-2-yl)-2,2-dimethyl-
5-heptenovou kyselinu, 7-(N-methyl-3-aminobicyklo[2.2.1]hept2-yl)-5-heptenovou kyselinu, 6-(3-aminobicyklo[2.2.1]hept-2yl)-5-hexenovou kyselinu. Specifické příklady 2-amino-6,6-dimethyl[3.1.1]bicyklické sloučeniny zahrnují 7-(2-amino-6,6-dimethylbicyklo[3.1.1]hept-3-yl)-5-heptenovou kyselinu. V těchto výchozích sloučeninách může být řetězec heptenové kyseliny nasycen za tvorby řetězce heptanové kyseliny, může být přerušen heteroatomy nebo heteroskupinami, jako je -0-, -S-, -NU- nebo fenylenem nebo může být substituován oxoskupinou. Příklady takových sloučenin zahrnují 7-(3-aminobicyklo[2.2.1]hept-2-yl)heptanovou kyselinu, 4-[2-(2-aminobicyklo[3.1.1]hept-3-yl)ethoxyfenyloctovou kyselinu, 7-(3-aminonicyklo[2.2.1]hept-2-yl)-6oxoheptanovou kyselinu. Tyto výchozí sloučeniny jsou popsány buď v Japonské patentové publikaci (ROKOKU) č. 79060/1993 nebo 23170/1991 nebo se mohou připravit podle způsobu který je zde popsán.
Sulfonová kyselina X3-X2~Xi-SO2OH a karboxylová kyselina X3-X2-X1-COOH odpovídající parciální struktuře
Z-X1-X2-X3 znamená sulfonovou nebo karboxylovou kyselinu mající substituenty odpovídající skupinám X shora. Příklady zahrnují alkan-sulfonovou kyselinu nebo -karboxylovou kyselinu, ······ ·· · ·· ·· ··· · · ♦· · · · · • · · ·· · ···· • · · · · · · * · · · · · ···· · · · ··· alken-sulfonovou kyselinu nebo -karboxylovou kyselinu, alkin-sulfonovou nebo -karboxylovou kyselinu, cykloalkan-sulfonovou kyselinu nebo -karboxylovou kyselinu, cykloalken-sulfonovou kyselinu nebo -karboxylovou kyselinu, aryl-sulfonovou kyselinu nebo -karboxylovou kyselinu, aralkyloxý-sulfonovou kyselinu nebo -karboxylovou kyselinu, heterocyklickou substituovanou-sulfonovou kyselinu nebo -karboxylovou kyselinu, heteroarylalkyl-sulfonovou nebo -karboxylovou kyselinu a substituovanou amin-sulfonovou nebo -karboxylovou kyselinu. Každá z těchto sulfonových a karboxylových kyselin může obsáhuvat substituenty uvedené shora. Tyto sulfonové kyseliny a karboxylové kyseliny jsou komerčně dostupné nebo se mohou připravit ze známých sloučenin podle známých způsobů. Je-li to nezbytné sulfonová kyselina nebo karboxylové kyselina se může převést na odpovídající reaktivní derivát uvedený Shora. Například jestliže je potřeba halogenid kyseliny, sloučenina reaguje s thionylhalogenidem (například thionylchlorid), halogenidem fosforu (například chlorid fosforitý, chlorid fosforečný) nebo oxalylhalogenidem (například oxalylchlorid) podle známých způsobů, jako jsou například popsány v literatuře (například Shin-Jikken-Kagaku-Koza, díl 14, str. 1787 (1978); Synthesis, 852-854 (1986); Shin-Jikken-Kagaku-Koza, díl 22, str. 115 (1992)). Ostatní reaktivní deriváty se také připraví podle známých způsobů.
Z cílových sloučenin obecného vzorce I se ty, kde postranní řetězec obsahuje nenasycenou vazbu, zejména dvojnou vazbu mohou také připravit reakcí aldehydového derivátu obecného vzorce III dále s ylidovou sloučeninou odpovídající zbytkové části postranního řetězce A-R při podmínkách pro Wittigovu reakci
ΦΦ φ Φ ΦΦ · · φ ·· ·· • · φ φ φ φφ φ φφ φ φφ φφφ φ φ φ φφφφ φ φφφφ φφφ φφφ
kde A, Β, R, Χ-ρ Χ2, Χ3, Υ a Z mají význam definovaný shora.
Výchozí sloučenina obecného vzorce III se může připravit podle postupu popsaném například v Japonské patentové publikaci (ΚΟΚΆΙ) č. 256650/1990. Dále, ylidová sloučeina odpovídající zbytku postranního řetězce A-R se může připravit reakcí trifenylfosfinu s odpovídající halogenovanou alkanovou kyselinou nebo esterovým derivátem, etherovým detivátem nebo amidovým derivátem v přítomnosti báze podle známých způsobů.
Z cílových sloučenin obecného vzorce I se ty, kde R znamená skupinu COOH, pokud je to nutné, mohou převést na odpovídající esterový derivát, alkoholový derivát, etherový derivát a amidový derivát. Například esterové deriváty se připraví esterifikací karboxylové kyseliny konvenčním způsobem. Esterový derivát se redukcí převede na alkoholový derivát, amidací dá amidový derivát. Etherový derivát se připraví O-alkylací alkoholového derivátu.
Sloučenina obecného vzorce podle vynálezu vykazuje antagonistickou účinnost proti PGD2 in vitro vázáním k PGD2 receptoru a je proto účinná jako léčivo pro léčení nemocí, při kterých dochází k disfunkci žírných buněk následkem přebytečné produkce PGD2. Například sloučenina obecného vzorce I je užitečná jako léčivo pro léčbu nemocí jako jsou ···♦ ·· ·· · ·· ·· • · · · · ·« «··· • · · · · · · · ··*· · ····«·· ··· systemická mastocytóza a poruch aktivace žírných buněk a tracheální kontrakce, astma, alergická rinitida, alergická konjuktivitida, kopřivka, poranění následkem ischeraické reperfůze a záněty. Sloučenina obecného vzorce vykazuje preventivní účinek na nazální okluzi in vivo a proto je užitečná jako léčivo pro její léčení.
Sloučenina obecného vzorce I podle vynálezu se pro léčbě může formulovat do formulací pro orální nebo parenterální podání. Farmaceutický prostředek obsahující sloučeninu obecného vzorce I podle vynálezu může být ve formě pro orální nebo parenterální podání. Specificky může být formulován do formulací pro orální podání, jako jsou tablety, kapsle, granule, prášky, sirupy apód; pro parenterální. podání ve formě injektovatelných roztoků nebo suspenzí pro intravenózní, intramuskulární nebo subkutánní injekce, inhalačních prostředků, očních kapek, nazálních kapek, čípků nebo perkutánních formulací, jako jsou masti.
Při přípravě formulací, nosičů, excipientů a rozpouštědel se použije způsobů známých odborníkům. Tablety se připraví lisováním nebo formulováním aktivní složky společně s pomocnou složkou. Příklady vhodných pomocných složek zahrnují farmaceuticky přijatelné excipienty, jako jsou pojivá (například kukuřičný škrob), plniva (například laktóza, mikrokrystalická celulóza), dezintegrační činidla (například sodný glykolát odvozený od škrobu) nebo mazadla (například stearát hořečnatý). Tablety mohou být vhodně povlečeny. V případě kapalných formulací, jako jsou sirupy, roztoky nebo suspenze, mohou obsahovat suspenzační činidla (například methylcelulóza), emulgátory (například lecitin), ochranná činidla apod. V případě injektovatelných formulací, mohou být ve formě roztoku nebo suspenze nebo olejovité vodné emulze, které mohou obsahovat stabilizátory suspenze nebo dispergátory apod. V případě inhalačního prostředku je formulován do kapalné formulace vhodné pro inhalační zařízení. V případě očních kapek je formulace provedena do roztoku nebo suspenze. Specielně, v případě nazálního léčiva pro léčbu nazální okluze se léčivo muže použít jako roztok nebo suspenze připravené konvenčním formulačním způsobem nebo jako prášek formulovaný za použití práškových činidel (například hydroxypropylcelulóza, karbopol), které jsou podány do nazální dutiny. Alternativně se může použít jako aerosol po naplnění do speciální nádoby společně s rozpouštědlem o nízkém bodu varu.
Ačkoliv vhodná dávka sloučeniny obecného vzorce I závisí na cestě podání, věku, tělesné hmotnosti, pohlaví nebo stavu pacienta a druhu současně podávaného léčiva, pokud se podává, a nakonec by měla být stanovena ošetřujícím lékařem, v případě orálního podání činí denní dávka mezi 0,01 až 100 mg, výhodněji 0,01 až 10 mg, ještě výhodněji 0,1 až 10 mg/kg hmotnosti. V případě parenterálního podání činí denní dávka 0,001 až 100 mg, výhodněji 0,001 až 1 mg, ještě výhodněji 0,01 až 1 mg/kg hmotnoti. Denní dávka může být podána v 1 až 4 dílčích dávkách.
Následující příklady jsou uvedeny pouze pro ilustraci a v žádném případě neomezují rozsah vynálezu.
Příklad 1
999 · | • 9 | 9· | 9 | 99 | 9 V | |||
• | • | 9 | • 9 | 99 | 9 9 | 9 | • | |
• | • | • | 9 | 9 | 9 | 9 9 | 99 | |
• | • | • 9 | 9 9 | 9 | 9 999 | 9 | 9 | |
• · | • | 9 | 9 | 9 | 9 | 9 | 9 | 9 |
Methyl (Z)-7-[(lS, 2R, 3R, 4R)-3aminobicyklo[2.2.1]hept-2-yl]-5-heptenoát (II-l) (251 mg, 1,00 mmol) se rozpustí v methylenchloridu (8 ml)a pod atmosférou dusíku se přidá triethylamin (0,238 ml, 2,00 mol). Ke směsi se přidá za Chlazení ledem 2-chlorsulfonyldibenzofuran (350 mg, 1,31 mmol) a směs se míchá po dobu 30 minut a nechá se ohřát na teplotu místnosti. Reakční směs se čistí sloupcovou chromatografií na silikagelu (n-hexan/ethylacetát (1:4)) a rekrystaluje se z n-hexanu (10 ml) a získá se methyl (Z)-7-[(1S,2R,3R,4R)-3-(2-dibenzofuryl)sulfonylaminobicyklo[2.2.1]hept-2-yl]-5-heptenoát (la-1) (342 mg, 0,710 mmol). Výtěžek 71 %, teplota tání 115 až 116 °C.
Elementární analýza (C27H31NO5S)
Vypočteno (%) : C, 67,34; H, 6,49; N, 2,91; S, 6,66
Nalezeno (%) . C, 67,16; H, 6,47; N, 2,99; S, 6,66
IČ (CHC13): 3382, 3024, 2952, 2874, 1726, 1583, 1465, 1442, 1319, 1245, 1154, 1121, 1104, 1071, 1019, 890, 840, 817 /cm.
XH NMR (CDC13) δ: 0,94 - 1,92 (14H, m) , 2,15 - 2,24 (3H, m), 2,99 - 3,07 (1H, m), 3,66 (3H, s), 4,98 (1H, d, J=6,6 Hz),
5,10 - 5,22 (2H, m) , 7,39 - 7,46 (1H, m), 7,51 - 7,70 (3H, m), 7,87 - 8,13 (2H, m) , 8,53 (1H, d, J=2,1 Hz).
[a]D = -0,6° (CHC13, c=1,01 %, 23 °C). [«]365 = +37,0° (CHC13, c=l,01 %, 23 °C).
Methyl (Z)-7-[(1S,2R,3R,4R)-3 -(2-dibenzofuryl)sulfonylaminobícyklo[2.2.1]hept-2-yl]-5-heptenoát (la-1) (234 mg, 0,50 mmol) se rozpustí ve směsi 6 ml methanolu a 4 ml tetrahydrofuranu. K roztoku se přidá za chlazení 1 N hydroxid draselný (1,50 ml, 1,50 mmol). Reakční směs se nechá ohřát na teplotu místnosti a potom se nechá reagovat po dobu 16 hodin a koncentrací se odstraní rozpouštědlo. Ke zbytku se přidá ethylacetát (50 ml) a voda (10 ml) a potom 1 N HC1 (2,00 mmol) a organická vrstva se oddělí. Organická vrstva se promyje nasycenou solankou, suší se přes bezvodý síran sodný a koncentruje se. Zbytek se čistí sloupcovou chromatografií na silikagelu (n-hexan/ethylacetát (1:1) obsahující 0,2 % kyseliny octové a získá se (Z)-7-[(1S,2R,3R,4R)-3-(2dibenzofuryl)sulfonylamidobicyklo[2.2.1]hept-2-yl]-5heptenová kyselina (la-2) (203 mg, 0,434 mmol). Výtěžek 87 %, olej .
IČ (CHC13): 3266, 3026, 2952, 2874, 1708, 1465, 1443, 1423, 1319, 1267, 1245, 1153, 1121, 1104, 1072, 906 /cm.
XH NMR (CDC13)S: 0,93 - 1,94 (14H, m), 2,12 - 2,19 (1H, m) , 2,26 (2H, t, J-7,2 Hz), 3,00 - 3,08 (1H, m), 5,12 - 5,25 (2H, m), 5,26 (1H, d, J=6,6 Hz), 7,38 - 7,45 (1H, m), 7,51 - 7,70 (3H, m), 7,87 - 8,13 (2H, m), 8,54 (1H, d, J=2,lHz).
[a]D = +6,8° (CHC13, c=1,08 %, 23 %).
(Z)-7-[(1S,2R,3R,4R)-3-(2-dibenzofuryl)sulfonylaminobicyklo[2.2.1]hept-2-yl]-5-heptenová kyselina (la-2) (453 mg,
0,97 mmol) se rozpustí v methanolu (5 ml). Přidá se 1 N methoxid sodný v methanolu (1,034 N, 0,937 ml, 0,97 mmol) a směs se nechá ohřát na teplotu místnosti a reaguje 1 hodinu. Rozpouštědlo se odstraní destilací a získá se sodná sůl (la-3) (457 mg, 0,933 mmol). Výtěžek 96 %.
Amorfní prášek.
Elementární analýza (C26H2gN05SNa.O,6H20)
Vypočteno (%) : C, 62,41; H, 5,88; N, 2,80; S, 6,41; Na, 4,59
Nalezeno (%): C, 62,45; H, 5,92; N, 2,99; S, 6,49;
Na, 4,46
IČ (KBr): 434, 3280, 3074, 3007, 2952, 2873, 1566, 1467, 1444, 1417, 1344, 1315, 1270, 1248, 1200, 1189, 1154, 1124, 1107, 1075, 1058, 895, 842, 818 /cm.
XH NMR (CHC13)Ó: 1,02 - 2,05 (16H, m), 2,16 - 2,23 (1H, m), 2,94 - 3,00 (1H, m), 4,98 - 5,05 (2H, m) , 7,41 - 7,48 (1H, m), 7,53 - 7,62 (1H, m), 7,66 (1H, d, J=8,4 Hz), 7,77 (1H, d, J=8,4 Hz), 8,57 (1H, d, J=2,l Hz).
[a ]D = -15,2° (CH3OH, c=1,07 %, 22 °C).
»····· ·· · ·· · · • · · · · · · · · · · • · ··· · · · ···· · • · · · ··· ♦ · ·
Příklad 2
Methyl (Z)-7-[(1S,2R,3R,4Rj-3-aminobicyklo[2.2.1]hept2-yl]-5-heptanoát trifluoracetát (II-2) (232 mg, 0,636 mmol), který byl připraven podle způsobu popsaném v referenčním příkladu 4 Japonské patentové publikace (KOKOKU) č. 79060/1993 se rozpustí v methylenchloridu (5 ml). K roztoku se přidá za chlazení triethylamin (0,279 ml, 2,0 mmol) a 4-bifenylkarbonylchlorid a roztok se míchá po dobu 7 hodin při téže teplotě. Reakční směs se čistí sloupcovou chromatografií na silikagelu (ethylacetát/n-hexan (1:4)) a získá se methyl (Z)-[(1S,2R,3R,4R)-3-(4-bifenyl)karbonylaminobicyklo[2.2.1Íhept-2-yl]-5-heptenoát (lk-11) (221 mg,
0,512 mmol). Sloučenina lk-11 (190 mg, 0,440 mmol) se rozpustí v methanolu (6 ml) . K roztoku se přidá za chlazení 1 Ν KOH a směs se míchá po dobu 15 hodin při teplotě místnosti. Reakční směs se koncentruje ve vakuu. Zbytek, po přidání vody (20 ml) a 1 N HC1 (2 ml)' se extrahuje ethylacetátem. Organická vrstva se promyje nasycenou solankou, suší se přes bezvodý síran sodný a koncentruje se. Zbytek se čistí sloupcovou chromatografií na silikagelu (ethylacetát/hexan (1:1) obsahující 0,3 % kyseliny octové) a získá se (Z)-7[(1S,2R,3R,4R)-3-(4-bifenyl)karbonylaminobicyklo(2.2.1]hept2-yl]-5-heptenové kyselina (lk-12) (172 mg, 0,412 mmol).
Výtěžek 94 %.
Následující sloučeniny se také mohou připravit následujícím postupem.
Příklad 3
CHO
NHSO2
(ΠΙ-1)
-j^Ca2* ^^NHSO;
(3d-l
K suspenzi 4-karboxybutyltrifenylfosfoniumbromidu (14/8 g, 33,3 mmol) a tetrahydrofuranu (80 ml) se přidá při teplotě místnosti a pod atmosférou dusíku terc.butyrát draselný (7,55 g, 67,3 mmol). Směs se míchá 1 hodinu při teplotě místnosti a potom se ochladí na -20 °C a pomalu se přidá roztok N-[(1S,2S,3S,4R)-3-formylmethylbicyklo[2.2.1]hept-2-yl]benzensulfonamidu (III-l) (Japonská patentová publikace (KOKAI) č. 256650/1990, referenční příklad 2) (3,25 g, 11,1 mmol) v tetrahydrofuranu (20 ml). Směs se míchá 1 hodinu při teplotě -20 °C, chladící lázeň se odstaví a směs se dále míchá 1 hodinu. K reakčnímu roztoku se přidá 2 N HC1 a směs se extrahuje ethylacetátem, promyje se solankou a koncentruje se. Po přidání toluenu a 1 N hydroxidu sodného ke vzniklému surovému produktu se vodná vrstva oddělí. Organická vrstva se promyje opět vodou a promývací kapalině se spojí s dříve získanou vodnou vrstvou. Přidá se 2 N HC1 a vodný roztok se extrahuje ethylacetátem. Extrakt se promyje vodou a solankou, suší se nad síranem sodným a koncentruje se. Zbytek se čistí sloupcovou chromatografíí na silikagelu a získá se (Z)-7-[(IR,2S,3S,4S)-3-fenylsulfonylaminobicyklo[2.2.ijhept2-yl]-5-heptenoát (ld-1) (3,29 g, výtěžek 99 %, teplota tání °C).
Elementární analýza (C2qH27NO4S)
Vypočteno (%): C, 63,63; H, 7,21; N, 3,71; S, 8,49
Nalezeno (%): C, 63,56; H, 7,21; N, 3,83; S, 8,43.
[a]D =+5,3 ± 0,5° (CHC13, c=l,003 %, 22 °C) [a]D =+27,1 ± 0,7® (MeOH, c=l,015 %, 24 ®C)
IČ (Nujol) 3282, 3260, 3300, 2400, 1708, 1268, 1248, 1202, 1162, 1153, 1095, 1076 /cm.
1H NMR δ | 0,88 - 2,10 | (m, | 14H) | , 2,14 | (š s, | 1H), 2,34 (t, J=7,2 |
Hz, 2H), | 2,95 - 3,07 | (m, | 1H) , | 5,13 - | 5, 35 | (m, 3H) , 7,45 - |
7,64 (m, | 3H), 7,85 - | 7,94 | (m, | 2H) , 9 | ,52 š | s, 1H). |
Sloučeniny připravené podle postupu popsaném v příkladech shora jsou uvedeny v tabulce dále.
- 28 • · · ·
Tabulka l a
la-1 la-2 la-3 la-4 la-5 la-6 la-7
H
Na
CHg
H
CHs
H
Ia-8 | ch3 |
la-9 | H |
la-10 | CHa |
la-11 | H |
la-12 | CHa |
la-13 | H |
la-14 | CHg |
la-15 | H |
la-I6 | CHa |
la-17 | H |
la-18 | CH3 |
la-19 | H |
la-20 | CH3 |
la-21 | H |
la-22 | H |
la-23 | H |
-O-O*°c^
• · — 29 -
la-24 | ch3 |
la-25 | H |
la-26 | Na |
la-27 | ch3 |
la-28 | H |
la-29 | Na |
la-30 | ch3 |
ja-31 | H |
la-32 | ch3 |
la-33 | H |
la-34 | CH3 |
la-35 | ch3 |
la-36 | H |
la-37 | CHa |
la-38 | H |
la-39 | CHg |
la-40 | H |
la-41 | H |
la-42 | ch3 |
Ia-43 | H |
la-44 | CHa |
la-45 | H |
Ia-46 la-47 la-48 la-49 la-50 la-51
Ia-52 la-53 la-54 la-55 la-56 la-57
Ia-58 la-59 la-«0 la~61 la-62 la-63 la-64 la-65 la-66 la-67 la-68
—
la-73
CH3 la-74
la-75
CHg la-76 “^^0-c°oRl la-77
CHa la-78
la-79 la-80 CH3 la-81 H
Ia-82
CH3 la-83
la-84
la-85H la-86H la-87H
- 32 •» 4 4 4 4 4· 4 • 44 · 4 · · · · ·· • « · ·· · ···· ·· ··· · · · ···· ·
4 4 · · 4 · 4· • 4 4« ·· 4 »· *444
χΓχ2-χ3 la-88 la-89
Ia-90 la-91 la-92 la-93 la-94 la-95 la-96 la-97 la-98 la-99
H H~C^OCK3
• · • » • ·
a · · · a a • · · ·» a a 8 a· • a a a aa « a a a a a a a a a aa • · · * a * a a a a * a * « « a a a · · la-100 CH3 la-101 H la-102
CHa la-103
CHg la-104 H la-105 la-106 la-107 la-108 la-109 la-110 ía-111 la-112 la-113 la-114
GHs
H
CHa
H
CHs
H
CH3
H
CH3
H
- 34 • ··
č. | Ri. | XrX2-X3 |
la-115 la-116 la-117 la-lJ8 | CHa H Na fPr | ~O~ch2O |
la-119 la-120 la-121 | CH, Na H | -0-°-0 |
Ia-122 la-123 | ch3 H | -O~nhO |
la-124 | CH3 | |
la-125 la-126 | CHg H | |
la-127 la-128 | CHg H | ~O~ch2^O~oh |
la-129 | ch3 | -^^-CHj-^^-GCHš |
la-130 la-131 | CH3 H | |
la-132 la-133 | CH, H | -Ό-θ-Ο-θ^ |
la-134 | H | |
la-135 la-136 | CHa H | |
la-137 la-138 | CHa H | ΛΜ-Ο o |
la-139 la-140 | CHa H | -^-0-0 |
la-145 la-146
Ia-147 la-148 la-149 la-150 la-151
H
H
H
H
OCH3
• 9 · · · 9 · · « · · · · • · · · t ·· 9 9 9 9
9 ♦ 9 9 9 «· 9 · 9 9 · «······ 9 9 ·
la-156 H la-157 H
la-158
la-160 H
• » · ♦ » » · · · · • · » · ♦ · • · · » « « • · ·« · · •··· ··
« ·· ·· • · · · · * • · « «* • » ·»» · ♦ • · · · ··· ·* · · la-162 la-163 la-164 la-165 la-166 la-167 la-168 la-169
Ja-í70 la-171 la-172
H
H
H
CHs
H
CH,
···· ·· ·· • · · · · · • · · · · • · · · ♦ ·
9 9 9 9 9
99
9 9 9
9 99
9999 9
Χι-Χ2-Χ3 la-173H la-174H la-175 la-176H la-177 la-178H la-17SCHg la-180H la-181H la-182CHs la-183H
···· • · • · • · — 39 —
·· • · ♦· •· ·· • · · ·<
• ·* ·· ·
la-184 la-185 la-186 la-187 la-188 la-189 la-190 la-191 la-192 la-193
H
CH3
H
CH3
H
CHa
H
COOR| — 40 ···· ··
la-195 la-196 la-197 la-198 la-199 la-200 la-0201 la-202 la-203
OChfe
Č.
xrxrx3 la-204 la-205 la-206 la-207
lá-208 la-209 la-210 la-211
Ia-212 la-213
OCHs
V?“OCH3
OCH;Í
99
9 9 9 « 9 9 9
9 9 9
9 9
99 9 ··· · • · · 9 ·9
9 9 ·9 • · · 9 ·· • 9 9 9 99
xrx2-x3 la-214 la-215
Ia-216 la-217 la-218 la-219 la-220 la-221
Ia-222
Ia-223
XrX2-X3 la-224 la-225 la-226 la-227
Ia-228 la-229 la-230 la-231 la-232 la-233
Ia-234 la-235
- 44 *··ι ·* • ·
la-237 la-238 la-239 la-240
Ja-242
00¾ la-243 la-244 la-245
OCHj la-246
X1-X2-X3
Č.
la-247 la-248 lař249 la-250 la-251 la-252 la-253 la-254 la-255 la-256 la-257
CHjO OCH3
·· ·· τ · · · • · ·· • ··· · · • · ·
COOH
č.
XrX2-X3 la-258 la-259 la-260 la-261 la-262 la-263 la-264 la-265 la-266 la-267 la-268 la-269 la-270 la-271
OCHa
CHs
CHa
- 47 COOH
la-273 la-274 la-275 la-276 la-277 la-278 la-279
la-283
la-284 la-285 la-286 la-287 la-288
Ia-289 la-290 la-291 la-292 la-293 la-294
S — 49 —
la-295
la-296
la-297
la-298 la-299 la-300 la-301
CHgQ, la-302 y-NO;, la-303 la-304 la-305
• ·
- 50 Tabulka lb
Č.
lb-1 lb-2 lb-3 lb~4 lb-5 lb-6 R1
CHs
CH3
H
H
H
H
XrX2-X3 ^0-0
CHgO
lb-9 lb-10
-δΙ-
ό.
Ri
XrX2-X3 lb-ll
OCHa lb-12 lb-13
OCHa lb-14 lb-15
H
- 52 _
Tabulka lc
c. | Ri |
lc-1 | CHa |
lc-2 | CHg |
lc-3 | K |
lc-4 | H |
loS | H |
lc-6 | H |
R-7 | H |
lc-8 | H |
Ic-9 | H |
lolO | H |
loll | H |
lc-12 | H |
X1-X2-X3 ·· · · • ·
Tabulka ld
xrx2-x3
ld-4
H SO2CH3 ld-5
ld-6 | H | SO2CH3 |
ld-7 | H | SO2CH3 |
ld-8 | H | SOjCHs |
ld-9 | H | SO2CH, |
ld-10
H SO2CH3
ld-11
H SOgCHg ld-12
H SO2CH3 ld-13
Η $θ2^Η3
Id-14
H SOgCHg
ld-15
H SOjCHg
- 55 Tabulka le
C.
Ri
Xi-X2-X3 le-1 'le-2
le-3 le-4 H le-5 H le-í
le-7 le-8
1C-9 h le-10 H
- 66 Tabulka lf
Č. R2 xrx2-x3 lf-1
If-2
lf-3 lf-4
If-5
1M ···» ··
lf-7H lf-Sh
If-9H lf-10H
··· · ·· *
c • ·
Tabulka lg
00¾
lg-7
H
lg-8
H
1g-9
H lg-10
lg-11
H
φ φ «
- 58 φ φ ·
Tabulka 11ι
♦ * φφφ *· • φ φ ·♦ • · φφφ· φ φ ·· φ · φ φ · ·♦♦ φφφφ ·· • φ
Η “0^0 lh-4 lh-5 Η lh-<>
• · · • * · ·
Tabulka li
č.
R2 xrx2-x3
* 4
Tabulka Ij
xrx2-x3
Ij-1 lj-2 lj-3 lj-4
IK lj-4»
11-7 lj-8
CHj
H
Na
H
CHg
CHa
H
CH3
lj-5 CH3 lj-10 h lj-11 CHa lj-12 H lj-13 CHg lj-14 H lj-15 CHa lj-Μ» H
- 61 ΦΦΦΦ Φ Φ
Φ Φ φφ
Φ
Φ
Φ
Φ Φ ♦
·»· ♦ Φ * · ·
Φ · «φ
Č. | *1 |
lj-17 | H |
lj-18 | CHa |
Ij-19 | H |
lj-20 | CHg |
lj-21 | H |
lj-22 | H |
lj-23 | CHa |
lj-24 | H |
lj-25 | CHg |
lj-26 | H |
lj-27 | H |
lj-28 | CHa |
lj-29 | H |
ΧΓΧ2-Χ3
-Οκ-ιτ€>
<···· ··
·♦
9 · 9
9 99
99 9 9 9
9 9
99
Tabulka lk
♦ ·« · ·· • · • · • 9 • · « · · * • « 4 · · · ·· ·· ··
c. | Ri | XrX2-X3 |
ik-i | H | -o-g^rQ |
lk-2 lk-3 | CHa H | |
lk-4 | H | —V/A? |
lk-5 | H | |
- w | ||
lk-6 | H | -O |
lk-7 | H | -0°-0 |
lk-8 | H | |
lk-9 | H | C~^~o_C^~oAc |
Ik-IO | H | |
lk-11 | CHa | ~o~o |
lk-12 | H | -ΟΌ. |
- 64 ···· ·· • ·· • 9· • · ·· • « · · ·
··· • ♦·
99
99
99999
9999
9 9·
999 • 99999
99
9999
COORj zNCOXrX2-X3
Č.
Ri xrx2-x3
Ik-13 lk-14
lk-15 lk-ló
lk-17 H
lk-18 lk-19 H lk-20
- 65 ···· ··
Tabulka hn
lin-1 | CH3 | |
lm-2 | H | |
lm-3 lm-4 | ch3 H | ~O~O |
lm-5 lm-6 | ch3 H | ~θ-Ν=Ν~θ |
lm-7 lm-8 | CHg H | |
lm-9 lm-10 | CH3 H | -O^°^O“oac |
I ni-11 lm-12 | CH3 H | ~O_o jO_oh |
lm-13 lm-14 | CHg H | |
lm-15 lm-16 | CHg H | —C^~“CXoAc |
lm-17 lm-18 | GHa H | —C^~~Ooh |
*· ·♦ • · · · é · ♦ ♦ ·· · · 9
9 · ·· ··
♦ ··· ··
lni—19 lm-20 lm-21
lm-22 | H | — |
lni-23 Im-24 | CHa H | ~o |
lna-25 lm-26 | CHa H | --θ-OAc |
lm-27 lm-28 | CHa H | _-ζ^-ΟΗ |
lm-29 lnj-30 | CHa H | |
Im-31 | H | O _ |
lm-32 | H | _ O /=\ » -O-C-Nv_v° |
lm-33 | H | ~o^o |
Ini-34 Η lm-35 lm-36 Η lnj-37 Η
lm-38 lm-39 lin-40 H
Tabulka 2a
Č.
Ri
XrX2-X3
2a-l | 0¾ |
2a-2 | H |
2a-3 | CHa |
2a-4 | H |
2a-5 | Na |
2a-6 | CHa |
2a-7 | H |
2a-8 | ch3 |
2a-9 | H |
2a-10 | 0¾ |
2a-ll | H |
2a-12 | CHa |
2a-13 | H |
2a-14 | CHa |
2a-15 | H |
2a-16 | CHa |
2a-17 | H |
2a-18 | CHa |
2a-19 | H |
2a-20 | CH3 |
2a-21 | H |
2a-22 | Na |
-θ-CHO
2a-23
2a-24
CH,
H
^^νηοοχ,-χ2 | ^COOR, *3 | XrXrX3 |
č. | Ri | |
2a-25 2a-26 | CHg Ή | “CKz~C^~O |
2a-27 2a-28 | ch3 H | “O~°~O |
2a-29 2a-30 | CHs H | |
2a-31 | CH3 | “O-Vn-q |
2a-32 2a-33 | CHa H | |
2a-34 | CH3 | /=\ _ M |
2a-3S | H | w — w |
2a-36 2a-37 | CH3 H | |
2a-38 2a-39 | CHa H | ^Q-Voh |
2a-40 | CHg | |
2a-41 | H | š |
2a-42 2a-43 | CHa H | ΟΛ”4 O |
2a-44 2a-45 | ch3 H | “O^N^yN-Q O |
2a*46 2a-47 | CHg H | Ολ |
s
4 4 4 •
· • 4
4 •4 •4 • 4 • 4
4
4
44· •
4
4
COORi
NHCOX1-X2-X3
č. | Ri | xrx2-x3 |
2a-48 2a-49 | ch3 H | |
2a-50 2a-51 | CHg H | s-4 NH2 |
2a-52 2a-53 | ch3 H | —θ-CN |
2a-54 2a-55 | CHg H | N-N H |
2a-56 2a-57 | CHg H | /=\ N-N ~Gr-VN GH3 |
2a-58 2a-59 | ch3 H | z=^ N=N |
2a-60 | CHa | “CrA |
2a-61 | H |
2a-62
2a-63
2a-64
2a-6S
2a-66
2a-67
»··· ··
c. | Ri | Xj-X2-X3 |
2a-68 | ch3 | |
2a-69 | H | Cs |
2a-70 2a-71 | ch3 H | |
2a-72 2a-73 | CHa H | |
2a-74 2a-75 | CHa H | |
2a-76 2a-77 | CHa H | cyc^°Ac |
2a-78 2a-79 | CHa H | -0-O°H |
2a-80 2a-81 | ch3 H | -O-hQ-och, |
2a-82 2a-83 | CHa H | -^Ooác |
2a-84 2a-85 | CHa H | ~O~oh |
2a-86 2a-87 | CHg H | —θ-QCHa |
···· | ·· | ·* | • | ·· | ·· | ||
• | • · | • · | ·· | • · | • | • | |
• | • · | • · | • | • · | ·· | ||
• | • · · | • · | • | • ··· | • | • | |
• · | • · | • · | • | • | • | • | |
·· | ·· | ·· | • e· | ·· | • · |
2a-90 CHa
2a-91 H
2a-92
2a-93
2a-94
2a-95
2a-96
2a-97
CH3
H
Na
Ca,/2
2a-98
2a-99
2a-100
2a-101
2a-102
2a-103
CHa
H
CH3
H
2a-104 | CHa |
2a-105 | Ή |
2a-106 | CHa |
2a-107 | H |
2alO8 | CHa |
2a-109 | H |
2a-310 | Na |
2a-Hl | CH3 |
2a-H2 | H |
······ ·· · ·· ·· ·· · · · · · · · · · ··· · · · ···· • · · · · · · · ···· · ······· ···
NHCOXpXg-Xg
č. | Rx | XrX2-X3 | |
2a-113 2a-114 | CHa H | -^-cf3 | |
2a-115 2a-116 | CH) H | ||
2a-117 2a-118 | CHg H | ||
2a-119 | H | OAc | |
2a-120 | H | OH | |
2a-121 | H | OCHg | |
2a-122 | H | O | |
2a-123 | H | -°*-Q | |
2a-124 | H | OH | |
2a-125 | H | ~y/ | - |
V# |
e · • ·
·· · ·· · • · · · ·
- 74 φφφφ φ φ • ·
č Rj
2a-126Η
2a-127Η
2a-128η
2a-129Η
2a-130n
2a-131Η
2a-132Η
2a-133
2a-134H
2a-135H
2a-136H xrx2-x3
Ό·
0Λ0 ίγΟ xo
• ·
Č.
Ri
XrX2-X3
2a-137
2a-138
2a-13í>
2a-140
2a-141
2a-142
2a-143
2a-144
2a-145
2a-146
2a-147
······ · · · ·Φ · · ·· · · · · » ¢44 4
4 ·«· 4 4 «9 44 4 44
4 4 4 4 4 4 4 44
4 4 4 4 4 44 4 4 44 4
COOR,
NHCOXi-Xz-Xg
c. | Ri | xrx2-x3 |
2a-148 | H | |
2a-14í> | H | |
- w | ||
2a-150 | H | |
2a-151 | H | |
2a-152 | H | H'c>~ -v |
2a-153 | H | H3C |
2a-154 | H | ~C^-CHa |
2a-155 | H | 3X3 |
2a-156 | H | H |
2a-157 | H | ~7T- h3cA'N |
2a-158 | H | V* |
2a-159 | H | “Ολ |
φ Φ « Φ Φ Φ ·· 9 ·· ·· • · · · Φ Φ Φ φ φφ φ
ΦΦΦ ΦΦ Φ ΦΦΦΦ
ΦΦ ΦΦΦ Φ φ φ ΦΦΦΦ φ
ΦΦΦΦ ΦΦ Φ ΦΦ Φ
ΦΦ ΦΦ ΦΦ «ΦΦ ΦΦ «Φ — ΊΊ —
Č. Rj xrx2-x3
2a-160 Η
2a-161Η
2a-162Η
2a-163Η
2a-I64Η
2a-165Η
2a-166Η
2a-167Η
2a-168Η
2a-169 Η
2a-170 Η
···· · · *· • · » · · »
‘COORj
NHCOXi-Xz-Xg
Č.
2a-171
2a-172
2a-173
2a-174
2a-175
2a-176
2a-177
2a-178
2a-179
2a-180
2a-181
2a-182
Rj XrX2-X3
H
H
H
H
H
H H
H
H
H
H
H
·«···· ·· * ·♦ · · • · · · · · · · « · 9 • · 9 9 9 9 9 9 999 ··
9 9 9 9 9 9 9 99
9 9 9 9 9 999 9 99 9
COOR,
NHCOXrXj-Xs
Č.
R1
2a-183
2a-184
2a-185
2a-186
2a-187
2a-188
2a-189
2a-190
2a-191
2a-192
2a-193
H
H
H
H
H
H
H
H
H
H
H
H
ČHg
H
CH3
CzHs
Ac ·
• · • · • ♦ ··· e ·· « • · · 9 9 · ····
9 ··· · · · 9 · · · · • · · « 9 9 · «·· • · · · 9 9 · 9 * 9 9 9 9
č. | xrx2-x3 | |
2a-194 | H |
2a-195
2a-196 H
2a-197 H
2a-198
2a-199
2a-200
2a-201
2a-202
2a-203
· • Μ
Č Χχ-Χ2-Χ3
2a-204
2a-205
2a-206
2a-207
2a-208
2a-209
2a-210
2a-211
2a-212
2a-213
2a-214
2a-215
2a-216
2a-217
2a-218
2a-2I9
2a-220
2a-221
2a-222
Xg^CHaOCHa
COCH,
2a-223 n
- 83 • · · ·
COOH 'NHGOXi-Xj-Xa
Č.
XrXrX3
2a-224
2a-227
2a-229
2a-232
2a-233
Č.
Xj-X2~X3
2a-237
2a-238
2a-239
2a-240
2a-241
2a-242
2a-243
2a-249
2a-250
HOffeC
2a-251
H3COH2C
COOH
NHCOVX2-X3
Č.
Xj-X2-X3
2a-252
2a-253
2a-254
HgCO
2a-255
2a-256
2a-2S7
COOH
Č.
2a-262
2a-2<S3
OCHg
2a-264
2a-265
2a-266
···· ·· · · • · · · ·· • 9999 • 9 9 9 9·
9 9 9 99 • 9 99 • · ·9
99 9
99 9 99
99
č ΧΓΧ2-Χ3
2a-269
2a-270
2a-271
2a-272
HO
2a-273
2a-274
O
2a-275
HON
Za-276
HO
2a-277
CHs
2a-279
CzHs
2a-280
2a-28í
2a-282
2a-283
COCH3
···· ·« • ·
č.
Χι-Χ2-Χ3
2a-290
2a-291
2a-292
2a-293
COCH,
2a-295
2a-296
OCHg
• ·
- 91 ···· ·♦
2a~297
2a-298 ~^^·^·η“0~ΟΟΗ3
2a-299
OCHa
2a-300
2a-301
HaC
2a-302
2a-303
2a-304
001¾
2a-305
2a-306
• ·· ·* ·· · · · · • · · ··
- 92 ···· ··
Č. xrx2-x3
2a-307
OCHg
2a-308
2a-3Q9
H3C
2a-310
OCHs
2á-311
2a-312
2a-313
2a-314
2a-3J5
OCHj
Tabulka 2b
2b-l
č. Rj X1-X2-X3
Tabulka 2d
Č.
2d-l
2d-2 xrx2-x3
-Q-°-Q “O
2d-3
Tabulka 2e
v,. | R1 | xrx2-x3 |
2e-l | H | “0~o-0 |
2c-2 | H | ~o |
2e-3 | H |
Tabulka 2f
c. | R1 | XrX2-X3 |
2f-l | H | |
2f-2 | H | -O |
2f-3 | H |
Tabulka 2g
XrX2-X3
2g-l
H SO2CH3
• · • · • · • ·· · · · · • · · · · · • · · · · · · · • · · · ·
- 95 Tabulka 2h
Tabulka 2i
COOH
O NHCOXj-Xj-Xa
Tabulka 2j
Č.
2H
2j-2
2j-3
2J-4
2j-5
Tabulka 2k
2j-«
2k-l
2k-2
2k-3
2k-4
2k-5
2k-6
- 97 Tabulka 3a
Č.
Ri
XrX2-X3
3a-l 3a-2 | CHa H | 'MU |
3a-3 | CHa | |
3a-4 | H | |
3a-5 | HaN+CťCHaOHla | “O~O |
3a-6 | Na | |
3a-7 | ijSCa | |
3a-8 | H | ——tBU |
3a-9
3a-10
3a-ll
3a-12
3a-13
3a-14
H
CHs
H
CHg
H
CHa
Br
3a-15 CHs
3a-16 H
3a-17 CH3
3a-18 u
• · · · · · • · · • · • ·
3a-21
3a-22
3a-23
3a-24
3a-25
3a-28
3a-29
3a-30
3a-26
3a-27
gCH?)3CH3 —(ChUbCH,
3a-31 | CHa | |
3a-32 | H | |
3a-33 | Ňa | |
3a-34 | H | γγ |
3a-35 | Na | kJL |
• · · · ·· · · • · · · · • · · 9 9 • 9 9 9 9 9
9 9 9 9 9 ·· 99*· • 9999 • · 9 9 9· • 9 99 9 • · · · 9 ·9 • · 99 •99 9999
Tabulka 3b
xrx2-x3
Tabulka 3c
3b-l
3b-2
3b-3 H
3b-4 H
Č.
Rt
3c-l
N=N
Tabulka 3d
3d-l 3d-2 | 1/2 Ca Na | -0 |
3d-3 | Na | |
3d-4 | Na | |
3d-5 3d-6 | CHa H | |
3d-7 | ch3 | |
3d-8 | H | |
3d-9 | Na | |
3d-10 | ch3 | |
3d-ll | H | “Vy |
3d-12 | Na | vJ |
3d-13 | 1/2 Ca | |
3d-14 | Ή | ΎΎΊ |
3d-15 | Na |
101 -
3d-17
3d-18 —(CHzfeCHg
3d-19 CHg
3d-20 H NHCHj
3d-21
3d-22
3d-23
CHa
H
H
Tabulka 3e
3d-24
3d-2S
3d-26
3d-27
3d-28
3d-2í>
3d-30
H Na
Na
CZHS raceniccompound raceniccoapound
racenic conpound
··· · ·· • ·
- 102 Fyzikálněchemické vlastnosti sloučenin uvedených shora jsou uvedeny dále. Číslo sloučeniny odpovídá číslu popsanému v tabulce shora.
Č. ia-4 [a]D = -11,5° (CHC13, c=l,01, 23,5 °C) .
Č. la-5 [Of] D = -10,0° (CHC13, C=l, 01, 25,0 °C) .
Č. la-6
CDC13 300 MHz
0,93 - 1,96 (14H, m) , 2,20 - 2,26 (3H, m), 3,03 (1H, m), 3,67 (3H, S), 4,99 (1H, d, J=6,6 Hz), 5,10 - 5,24 (2H, m), 7,37 7,51 (3H, m), 7,54 - 7,64 (3H, m), 7,76 - 7,88 (2H, m), 8,11 (1H, m) .
IČ (CHC13): 3384, 3278, 3026, 2952, 2874, 1727, 1436, 1411, 1324, 1155, 1097 /cm.
la]D = -9,0° (CHC13, C—1,04, 22,0 °C).
Č. la-7
CDC13 300 MHz
0,93 -2,0 (14H, m), 2,18 (1H, m), 2,28 (2H, t, 3=1,2 Hz),
3,04 (1H, m), 5,15 - 5,25 (2H, m), 5,28 (1H, d, J=6,9 Hz),
7,36 - 7,50 (3H, m), 7,54 - 7,63 (3H, m), 7,76 - 7,89 (2H,
m), 8,12 (1H, m).
IČ (CHC13): 3268, 3028, 2952, 2872, 1708, 1452, 1410, 1324, 1155, 1097 /cm.
[0f]D = -9,1° (CHC13, C=l,01, 24,0 °C) .
Č. la-8
CDC13 300 MHz
0,94 - 1,99 (14H, m), 2,21 - 2,29 (3H, m), 3,05 (1H, m), 3,67 (3H, s), 4,92 (1H, d, J-6,3 Hz), 5,14 - 5,30 (2H, m), 7,70 7,78 (6H, m), 7,96 - 8,01 (2H, m).
IČ (CHC13) : 3376, 3272, 3018, 2946, 2868, 1727, 1616, 1435,
103
1388, 1324, 1162, 1130, 1069 /cm.
[a]D = +1,6° (CHC13, c=1,01, 24,0 °C). teplota tání 117 až 119 GC.
Č. la-9
CDC13 300 MHz
0,95 - 2,08 (14Π, m), 2,19 (1H, m), 2,32 (2H, t, J=7,2 Hz),
3,06 (1H, m), 5,20 - 5,30 (2H, m), 5,34 (1H, d, J=6,6 Hz), 7,69 - 7,78 {6H, m), 7,96 - 8,03 (2H, m).
IČ (CHC13): 3260, 3020, 2950, 2868, 1708, 1389, 1324, 1162, 1130, 1069 /cm.
[a!]D = +13,3° (CHC13, c=l,05, 24,0 °C) .
teplota tání 118 až 120 °C.
Č. la-10
CDC13 300 MHz
0,96 - 1,98 (14H, m), 2,15 - 2,32 (3H, m), 3,04 (1H, m), 3,66 (3H, S), 5,12 - 5,26 (5H, m) , 7,67 - 7,78 (4H, m), 7,93 8,07 (4H, m).
IČ (CHC13): 3276, 3018, 2946, 2868, 1726, 1595, 1435, 1341, 1162, 1095 /cm.
[a]D = -1,5° (CHC13, c=l,01, 25,0 °C).
teplota tání 133 až 139 °C
Č. la-11
CD30D 300 MHz
1,05 - 1,98 (14H, m), 2,13 - 2,22 (3H, m), 2,97 (1H, m) , 5,09 - 5,22 (2H, m), 7,85 - 7,92 (4H, m), 7,95 - 8,05 (4H, m) .
IČ (KBr): 3385, 3261, 3069, 3003, 2954, 2872, 1708, 1596, 1428, 1413, 1378, 1343, 1326, 1236, 1186, 1160, 1096 /cm. teplota tání 144 až 146 °C.
Č. la-12
CDC13 300 MHz
0,96 - 1,96 (14H, m), 2,22 - 2,27 (3H, m), 3,03 (1H, m), 3,66 (3H, s) , 3,87 (3H, s) , 4,86 (TH, d, J=6,9 Hz), 5,18 - 5,24
104
(2H, m) , 6,99 - 7,02 (2H, m) , | 7,55 - 7,66 | (2H, | m) , 7, | 66 - |
7,69 (H, m), 7,89 - 7,92 (2H, | m) . | |||
IČ (CHC13): 3374, 3270, 3016, | 2948, 2870, | 1726, | 1608, | 1518, |
1487, 1458, 1437, 1248, 1157, | 1037 . | |||
[a]D = +4,2° (CHC13, C=l,01, | 24,0 °C). |
teplota tání 85 až 87 °C.
Č. ia-13
CDC13 300 MHz
0,97 - 1,99 (14H, m) , 2,18 (1H, m) , 2,30 (2H, t, J=7,2 Hz),
3,04 (1H, m) , 3,86 (3H, s) , 5,18 (1H, d, J=5,7 Hz), 5,23 5,26 (2H, m) , 6,99 - 7,02 (2H, m) , 7,55 - 7,58 (2H, m), 7,66 - 7,68 (2H, m) , 7,89 - 7,92 (2H, m) .
IČ (CHC13): 3380, 3260, 3020, 2948, 2868, 1708, 1608, 1519, 1487, 1458, 1306, 1293, 1248, 1156 /cm.
[a]D = +18,3° (CHC13, c=l,00, 25,5 °C) .
Č. ia-14
CDC13 300 MHz
0,98 - 2,00 (14H, m), 2,20 (1H, m), 2,25 (2H, t, J=7,2 Hz), 3,02 (1H, m), 3,67 (3H, s), 4,85 (1H, d, J=6,3 Hz), 5,19 5,25 (2H, m), 7,13 (1H, dd, J=4,8, 3,6 Hz), 7,39 (1H, d, J=4,8 Hz), 7,40 (1H, d, J=3,6 Hz), 7,71 - 7,74 (2H, m), 7,86 - 7,89 (2H, m).
IČ (CHC13): 3374, 3270, 3018, 2946, 2868, 1727, 1593, 1434, 1322 /cm.
[a]D = +5,6° (CHC13, c=1,01, 24,0 °C).
teplota tání 69 až 71 °G.
Č. la-15
CDC13 300 MHz
0,95 - 2,00 (14H, m), 2,17 (1H, m) , 2,32 (2H, t, J=7,2 Hz),
3,03 (1H, m), 5,20 (1H, d, J=6,9 Hz), 5,24 -5,28 (2H, m),
7,13 (1H, dd, J=4,8, 3,3 Hz), 7,38 (1H, d, J=4,8 Hz), 7,43 (1H, d, J=3,3 Hz), 7,73 (2H, d, J=8,4 Hz), 7,87 (2H, d, J=8,4
Hz) .
105
• · · | • · | • · | • · · | ·♦ | ||
• | • | • | • · | • · | • · | • |
• | • | • | • · | • | * · | • · |
• | • | • · | • · | • | • · · · | • |
• | • | • | • · | • | • | • |
IČ (CHC13): 3260, 3022, 2948, 2868, 1709, 1593, 1404, 1321, 1154 /cm.
[a]D = +20,8° (CHC13, c=1,07, 23,0 6C) .
teplota tání 71 až 73 °C.
Č. la-16
CDC13 300 MHz
0,98 - 2,00 (14H, m), 2,27 (2H, t, J=7,5 Hz), 2,28 (1H, m),
3.13 (1H, m), 3,66 (3H, s), 4,90 (1H, d, J=6,9 Hz), 5,25 5,29 (2H, m), 7,40 - 7,65 (6H, m), 7,76 (1H, d, J=8,4 Hz), 7,90 -8,02 (4H, m).
IČ (CHC13): 3376, 3276, 3018, 2946, 2868, 1726, 1593, 1435, 1394, 1322, 1159 /cm.
[tt]D = +7,0° (CHC13, c=l,07, 24,0 °C).
Č. la-17
CDC13 300 MHz
1,02 - 2,07 (14H, m), 2,25 (1H, m), 2,34 (2H, t, J=6,6 Hz),
3.14 (1H, m), 5,28 - 5,33 (3H, m), 7,39 - 7,57 (4H, m), 7,62 - 7,65 (2H, m), 7,76 (1H, d, J=8,l Hz), 7,89 - 8,02 (4H, m). IČ (CHC13): 3260, 2948, 2868, 1709, 1593, 1394, 1324, 1157 /cm.
[tt]D = +20,2° (CHC13, c=1,02, 24,0 °C).
Č. ia-18 t, J=7,2 Hz) , 2,33 (1H, m) , (1H, d, J=6,6 Hz), 5,24 ,9 Hz), 7,39 - 7,45 (3H, m), 7,62 (2H, m).
2946, 2868, 1727, 1433, 1331,
CDC13 300 MHz
1,05 | - 1, | 97 | (14H, m), 2 | ,25 | (2H |
3,12 | (1H, | ni) | , 3,67 (3H, | š) | , 4/ |
5,29 | (2H, | m) | , 7,24 (1H, | d, | J=3 |
7,56 | (1H, | d, | J-3,9 Hz), | 7, | 59 - |
IČ (chci3 | ) ·. | 3372, 3272, | 30 | 18, : | |
1152 | /cm. |
[tt]D = -5,7° (CHC13, C=l,01, 23,0 °C).
č. ia-19
CDC13 300 MHz • ♦· φφ φ φφ Φ· • · · · · φφ · φ φ φ
106 • φ · · · · · · φφ φ φ φ ··· φφφ φφ*
1,05 - 2,05 (14Η, m) , 2,28 - 2,33 (3Η, τη), 3,13 (1Η, τη), 5,18 (1Η, d, J=6,3 Hz), 5,27 - 5,31 (2Η, m) , 7,24 (1H, d, J=4,2 Hz), 7,39 - 7,42 (3H, τη) , 7,56 (ÍH, d, J=4,2 Hz), 7,58 - 7,62 (2H, m) .
IČ (CHC13) : 3372, 3254, 3018, 2948, 2868, 1707, 1431, 1328, 1151 /cm.
[a]D = +4,5° (CHC13, c=1,O1, 21,5 °C).
Č. la-20
CDC13 300 MHz
1,05 - 2,00 (14H, m), 2,26 (2H, t, J=7,5 Hz), 2,33 (1H, m),
3,11 (1H, m), 3,68 (3H, s) , 4,92 (1H, d, J-6,0 Hz), 5,27 (2H, m), 7,05 (1H, m), 7,10 (1H, d, J=3,6 Hz), 7,25 (1H, m), 7,32 (1H, m), 7,49 (1H, d, J=3,6 Hz).
IČ (CHC13): 3372, 3272, 3018, 2946, 2686, 1727, 1438, 1417, 1333, 1151 /cm.
[a]D = -9,2° (CHC13, C=l,01, 25,0 °C) .
Č. la-21
CDC13 300 MHz
1,02 - 2,01 (14H, m), 2,28 - 2,34 (3H, m), 3,13 (1H, m) , 5,12 (1H, d, J=6,9 Hz), 5,28 -5,32 (2H, m) , 7,06 (1H, m), 7,10 (1H, d, J=3,9 Hz), 7,25 (1H, m), 7,32 (1H, m), 7,50 (1H, d, J=3,9 Hz).
IČ (CHČ13): 3350, 3250, 2948, 1709, 1440, 1420, 1330, 1151. [a]D = +2,5° (CHC13, c=1,00, 25,0 ’C) .
Č. la-22
CDC13 300 MHz
0,96 - 2,05 (14H, m), 2,25 (1H, m), 2,35 (2H, t, J=7,0 Hz),
3,11 (ÍH, m), 5,20 - 5,34 (2H, m), 5,41 (ÍH, d, J=6,6 Hz),
7,31 - 7,49 (5H, mí), 7,62 (ÍH, d, J=7,8 Hž) , 8,11 (ÍH, dd, J=l,8 a 7,8 Hz), 8,35 (ÍH, d, J=l,8 Hz).
IČ (CHC13): 3384, 3271, 3025, 2958, 1708, 1608, 1559, 1537, 1168 /cm.
[a]D = +18,3° (CHC13, c=0,31,
22,0 °C) .
···· ♦ · ·· φ ·· ·· φφφ φφφφ φφφφ φφφ φφ φ φφφφ • φ φφφ φ φ φ φφφφ φ φφφφ φφφ φφφ
107
Č. la-23
CDC13 300 MHz
0,97 - 2,07 (14Η, m), 2,24 (1H, m), 2,35 (2H, t, J=6,9 Hz),
3,09 (1H, m), 3,86 (3H, s), 5,24 - 5,35 (2H, m), 5,44 (1H, d, J-6,3 Hz), 6,97 - 7,00 (2H, m), 7,26 - 7,28 (2H, m), 7,59 (1H, d, J=8,l Hz), 8,06 (1H, dd, J=2,1 a 8,1 Hz), 8,29 (1H, d, J=2,1 Hz) .
IČ (CHC13) : 3384, 3270, 2959, 1709, 1609, 1535, 1519, 1357, 1302, 1255, 1226, 1169 /cm.
[cďD = +17,0° (CHC13, c=1,OO, 21,0 °C) .
Č. la-24
CDC13 300 MHz
0,95 - 2,00 (14H, m), 2,20 - 2,25 (1H, m), 2,26 (2H, t, J=7,2 Hz), 3,02 - 3,10 (1H, m), 3,66 (3H, s), 4,92 (1H, d, J=6,6 Hz), 5,16 - 5,31 (2H, m), 7,52 - 7,60 (3H, m), 7,94 - 8,06 (6H, m) .
IČ (CHC13) : 3376, 3020, 2946, 2868, 1726, 1436, 1366, 1298, 1164, 1090, 890/cm.
[a]D = +11,2° (CHC13, c=1,04, 23,5 °C).
teplota tání 101 až 103 °C.
Č. la-25
CDC13 300 MHz
0,95 - 2,08 (14H, m), 2,15 - 2,22 (1H, m), 2,33 (2H, t, J-6,9 Hz), 3,02 - 3,10 (1H, m), 5,21 - 5,31 (2H, m), 5,34 (1H, d, J=6,3 Hz), 7,51 - 7,59 (3H, m) , 7,92 - 8,07 (6H, m).
IČ (CHC13): 3258, 3022, 2948, 2868, 1707, 1399, 1328, 1298, 1163, 1089, 1051, 892/cm.
[cdD = +29,8 ± 0,7° (CHC13, C=l,05, 25,0 °C) .
teplota tání 158 až 160 °C.
Č. la-26
Analýza pro c26H30N3°4SNa'8H2O:
Vypočteno: C, 60,29; H, 6,15; N, 8,11; S, 6,19; Na,
108
4,44;
Nalezeno: C, 60,15; H, 6,19; N, 8,15; S, 6,03; Na,
4,98.
[a]D = -16,6° (CHC13, C=l,04, 25,0 °C).
Č. la-27
CDC13 300 MHz
0,92 | - 1,98 | (14H, m), 2, | 20 (1H, m), 2, | 26 | (2H, t, J=7,5 Hz), |
3,03 | (1H, m) | , 3,12 (6H, | S), 3,66 (3H, | s) , | 4,87 (ÍH, d, J-6,6 |
HZ) , | 5,16 - | 5,32 (2H, m) | , 6,73 - 6,80 | (2H | , m), 7,88 - 8,00 |
(6H, | m) . | ||||
IČ (CHC13): | 3376, 3020, | 2946, 1726, 1601, | 1518, 1442, 1419, | ||
1362, | 1312, | 1163, 1133, | 1088/cm. |
[a]D = +55,3° (CHC13, C=0,53, 24,0 °C).
teplota tání 158 až 168 °C.
Č. la-28
CDC13 + CD3OD 300 MHz
0,99 - 2,14 (14H, m), 2,21 (TH, m), 2,31 (2H, t, J=7,2 Hz),
2,94 (1H, m), 3,12 (6H, s), 5,22 - 5,38 (2H, m) , 6,73 - 6,81 (2H, m), 7,87 - 8,00 (6H, m).
IČ (KBr): 3434, 3309, 2946, 1708, 1604, 1520, 1442, 1416, 1366, 1312, 1252, 1164, 1155, 1134, 1091/cm.
[aJD = neměřitelné (zbarvené, nedostatečná energie) teplota tání 193 až 196 °C
Č. la-29
CD3OD 300 MHz
1,02 - 1,96 (14H, m) , 2,10 (2H, t, J=7,8 Hz), 2,16 (1H, m),
2,98 (1H, m), 3,11 (6H, s), 5,07 - 5,27 (2H, m) , 6,80 - 6,87 (2H, m) , 7,84 - 8,0 (6H, m).
IČ (KBr): 3433, 3087, 3004, 2949, 2871, 1604, 1565, 1520,
1444, 1420, 1364, 1312, 1253, 1163, 1136, 1090/cm.
íce] neměřitelné ···· ·· • · • 9
- 109
Č. la-30
CDC13 300 MHz
0,95 -1,99 (14H, m), 2,22 (1H, m), 2,26 (2H, t, J=7,2 Hz),
2,35 (3H, s), 3,06 (1H, m), 3,66 (3H, s), 4,95 (1H, d | J=6, | |||
Hz), 5,15 - 5,30 (2H, m) | , 7,26 | - 7,32 (2H, | m), 7,97 - | 8,06 |
(6H, m). | ||||
IČ (CHC13): 3374, 2996, | 2946, | 2868, 1763, | 1728, 1591, | 1495, |
1435, 1368, 1299, 1228, | 1192, | 1163, 1139/cm. | ||
[a]D = +12,9° (CHC13, c= | :1,04, | 26,0 °C). |
Č. la-31
0,93 - 2,01 (14H, m) , 2,19 (1H, m) , 2,31 (2H, t, J=7,2 Hz),
2,35 (3H, S), 3,06 (1H, m), 5,17 - 5,32 (2H, m), 7,25 - 7,32 (2H, m) , 7,96 - 8,07 (6H, m). IČ (CHC13). 3267, 3028, 2952, 1368, 1328, 1299, 1163, 1138, [a]D = +21,7 ° (CHC13, c=0,51,
2874, 1759, 1708, 1592, 1495,
1088, 1050, 1008/cm.
22,0 °C).
Č. la-32
CDC13 300 MHz
0,93 - 1,99 (14H, m), 2,21 (1H, m), 2,27 (2H, t, J=7,2 Hz),
3,05 | (1H, m), 3,67 (3H, | S) , 4 | ,92 (1H, d, J=6,6 Hz), 5, | 15 - |
5,30 | (2H, m), 6,72 (1H, | S) , 6 | ,96 - 7,00 (2H, m), 7,86 | - 8,04 |
(6H, | m) . | |||
IČ (CHC13): 3374, 3276, | 3018, | 2946, 2686, 1725, 1605, | 1589, | |
1502, | 1433, 1396, 1330, | 1271, | 1164, 1135, 1089/cm. | |
[alD | = +18,6° (CHC13, c= | -1,00, | 26,0 °C). |
Č. la-33
CDC13 + CD3OD 300 MHz
0,98 - 2,08 (14H, m) , 2,20 (1H, m), 2,28 (2H, t, J=7,2 Hz),
2,98 (1H, m), 5,18 - 5,32 (2H, m) , 6,92 - 6,99 (2H, m) , 7,85
- 8,02 (6H, m) .
IČ (KBr): 3385, 3248, 2948, 2876, 1717, 1601, 1505, 1430,
1399, 1296, 1280, 1219, 1165, 1136, 1092/cm.
[a]D = -16,0° (CH3OH, c=l,08, 26,0 °C).
·· ··
V 9 9 9 ···· ·· • · 9 * · ·
110 teplota tání 208 až 210°C.
Č. la-34 teplota tání 82 až 83 PC.
[tt]D = +10,6° (CHC13, c=1,01, 23,5 °C).
Č. la-35 teplota tání 80 až 82 °C.
[a]D = -1,8° (CHC13, C=l,07, 22,0 °C).
Č. la-36
TLC Rf =^0,25 (ethylacetát/n-hexan=l: 1 (0,3 % kys. octová))
Č. la-37
CDC13 300 MHz
0,92 - 1,96 (14H, m) , 2,21 (IH, m), 2,27 (2H, t, J=7,4 Hz), 3,01 (IH, m), 3,66 (3H, s), 4,71 (IH, d, J-6,6 Hz), 5,14-5,29 (2H, m), 7,12 (IH, d, J=16,2 Hz), 7,24 (IH, d, J-16,2 Hz),
7,28 - 7,42 (3H, m) , 7,52 - 7,56 (2H, m) , 7,62 (2H, d, J=8,7 Hz), 7,85 (2H, d, J=8,7 Hz).
IČ (CHC13): 3384, 3283, 3023, 2954, 2876, 1730, 1595, 1494, 1317, 1163, 1147/cm.
[a]D = +10,5° (CHC13, c=l,01, 24,0 GC).
teplota tání 116 až 117 °c.
Č. ia-38
CDC13 300 MHz
0,92 - 1,99 (14H, m) , 2,17 :(1H, m) , 2,32 (2H, t, J=7,2 Hz) ,
3,02 (IH, m), 5,23 - 5,29 (3H, m), 7,11 (IH, d, J=16,2Hz), 7,23 (IH, d, J=16,2 Hz), 7,28 - 7,41 (3H, m), 7,52 - 7,55 (2H, m), 7,61 (2H, d, J=8,7 Hz), 7,86 (2H, d, J=8,7 Hz).
IČ (CHC13): 3515, 3384, 3270, 3022, 3015, 2957, 2876, 2669, 1708, 1595, 1496, 1320, 1157/cm.
[a]D = +27,1° (CHC13, C=l,02, 24,0 °C).
111
Č. la-39
CDC13 300 MHz
0,92 - 1,99 (14H, m) , 2,15 (1H, m), 2,28 (2H, t, J=7,4 Hz),
3,01 (1H, m), 3,68 (3H, s), 4,96 (1H, d, J=6,6 Hz), 5,16 -
5,32 (2H, m) , 6,60 (1H, d, J=12,0 Hz), 6,74 (1H, d, J=12,0 Hz), 7,16 - 7,23 (5H, m), 7,35 (2H, d, J=8,4 Hz), 7,72 (2H, d, J=8,4 Hz).
IČ (CHC13): 3384, 3283, 3023, 3015, 2954, 2876, 1730, 1595, 1493, 1324, 1163, 1147/cm.
[Of]D = +13,7° (CHC13, C=l,00, 24,0 ’C).
Č. la-40
CDC13 300 MHz
0,90 - 2,16 (14H, m) , 2,12 (1H, m) , 2,34 (2H, t, J=7,2 Hz),
3,02 (TH, m), 5,16 (1H, d, J=6,9 Hz), 5,23 - 5,34 (2H, m) ,
6,60 (1H, d, J=12,3 Hz), 6,74 (1H, d, J=12,3 Hz), 7,14 - 7,24 (5H, m), 7,35 (2H, d, J=8,lHz), 7,72 (2H, d, J=8,lHz).
IČ (CHC13): 3515, 3384, 3269, 3025, 3021, 3014, 2957, 2876, 2668, 1709, 1595, 1322, 1162, 1147/cm.
[of]D = +26,4° (CHC13, c=l,00, 24,0 °C) .
Č. la-41
CDC13 300 MHz
0,98 - 1,99 (14H, m), 2,17 (1H, m), 2,32 (2H, t, J=7,2 Hz),
3,00 (1H, m) , 3,84 (3H, S) , 5,20 - 5,26 (3H, m) , 6,90 - 6,95 (2H, m), 6,98 (TH, d, J=16,2 Hz), 7,17 (1H, d, J=16,2 Hz), 7,46 - 7,49 (2H, m), 7,58 (2H, d, J=8,4Hz), 7,83 (2H, d, J=8,4 Hz).
IČ (CHC13): 3258, 3018, 3002, 2950, 1709, 1590, 1509, 1457, 1404, 1302, 1250, 1153/cm.
[a]D = +30,2° (CHC13, c=l,00, 23,0 °C) .
teplota tání 99 až 100 °C.
Č. la-42
CDC13 300 MHz
1,01 - 1,99 (14H, m), 2,28 (2H, t, J=7,2 Hz), 2,30 (1H, m),
112 ······ · · « «· ·· • · · · ··· · · · · • · · · · · ···· • · · · · « · · · · · · · ······· ··· • · · ♦ · β · · · · 9 · ·
3,10 (1Η, m), 3,66 (3H, s), 5,07 (1H, š), 5,25 - 5,30 (2H,
m) , 6,98 - 7,04 (2H, m) , 7,16 (1H, d, J=16,2 Hz), 7,28 - 7,37 (3H, m) , 7,47 - 7,50 (3H, m).
IČ (CHC13): 3372, 3276, 3020, 2946, 2870, 1727, 1491, 1433, 1331, 1152/cm.
[a]D = -11,5° {CHC13, c=l,07, 21,5 °C).
Č. la-43
CDC13 300 MHz
0,98 - 2,00 (14H, m) , 2,11 - 2,36 (3H, m) , 3,12 (1H, m) , 5,10 (1H, d, J=6,6 Hz), 5,29 - 5,32 (2H, m), 6,99 - 7,04 (2H, m), 7,23 (1H, d, J=21,6 Hz), 7,32 - 7,49 (6H, m) .
IČ (CHC13): 3380, 3248, 3020, 2948, 2868, 1709, 1491, 1430, 1329, 1151/cm.
[a]D = +3,4° (CHC13, C=l,03, 25,0 °C).
Č. la-44
CDC13 300 MHz
1,00 - 2,00 (14H, m), 2,13 (1H, m), 2,29 (2H, t, J=7,4 Hz),
2,90 - 3,13 (5H, m) , 3,68 (3H, s), 4,74 (1H, d, J=6,6 Hz),
5,15 - 5,30 (2H, m), 7,18 - 7,29 (7H, m), 7,76 (2H, d, J=8,l Hz) .
IČ (CHC13): 3384, 3282, 3063, 3028, 3023, 3016, 2953, 2876, 1730, 1599, 1496, 1319, 1157/cm.
[a?]D = +2,3° (CHC13, c=l,00, 25,0 °C) .
teplota tání 85,0 až 86,0 °C.
Č. la-45
CDC13 300 MHz
0,90 - 2,05 (14H, m) , 2,09 (1H, m), 2,35 (2H, t, J=6,9 Hz),
2,90 - 3,13 (5H, m), 5,18 (1H, d, J=6,6 Hz), 5,24 - 5,34 (2H, m), 7,10 - 7,27 (7H, m) , 7,76 (2H, d, J=8,4 Hz).
IČ (CHC13): 3510, 3384, 3270, 3087, 3063, 3026, 3018, 3014, 2955, 2876, 2670, 1708, 1599, 1496, 1318, 1157/cm.
[o?]D = +8,5° (CHC13, c=l,01, 25,0 °C) .
113
Č. la-46 [a]D = +6,8° (CHC13, c=1,05, 25,0 °C) . teplota tání 99 až 100 °C.
Č. la-47
CDC13 300 MHz
0,97 - 2,01 (14H, m), 2,14 (1H, m), 2,36 (2H, t, J=7,2 Hz),
3,02 (1H, m), 5,23 (1H, d, J=5,4 Hz), 5,26 - 5,30 (2H, m),
7,37 - 7,39 (3H, m) , 7,54 - 7,58 (2H, m), 7,63 - 7,66 (2H,
m), 7,85 - 7,88 (2H, m).
IČ (CHC13): 3375, 3260,, 3022, 2948, 2212, 1707, 1596, 1497, 1396, 1322, 1160/cm.
[a]D = +25,0° (CHC13, c=1,02, 24,0 °C) .
teplota tání 117 až 118 °C.
č. ia-48
CD30D 300 MHz
1,05 - 1,93 (14H, m) , 2,10 - 2,15 (3H, m), 2,96 (1H, m), 5,08
- 5,28 (2H, m), 7,38 - 7,40 (3H, m) , 7,554 - 7,56 (2H, m) ,
7,69 <1H, d, J=8,4 Hz), 7,87 (1H, d, J=8,4 Hz).
Č. la-49
CDC13 300 MHz
0,96 - 1,97 (14H, m), 2,24 (1H, m) , 2,31 (2H, t, J=6,9 Hz),
3,05 (1H, m), 3,69 (3H, s), 5,15 (1H, d, J=6,6 Hz), 5,25 5,27 (2H, m) , 7,40 - 7,43 (3H, m), 7,61 - 7,64 (2H, m), 7,85 (1H, d, J=8,l Hz), 8,07 (1H, dd, J=8,l, 1,8 Hz), 8,58 (1H, d, J=l,8 Hz).
IČ (CHC13): 3374, 3020, 2948, 2870, 2212, 1726, 1606, 1530, 1493, 1345, 1167/cm.
[a]D = +2,4° (CHC13, c=l,03, 25,0 °C).
teplota tání 77 až 79 °C.
Č. la-50
CDC13 300 MHz
1,00 - 2,02 (T4H, m), 2,20 (1H, m), 2,34 (2H, t, j=6,6 Hz), ·····* ·· · · · · · • · · « e · · * · · ·
114 •· ··· · · · ···· · »······ ···
3,08 (1H, m), 5,26 - 5,29 (2H, m), 5,41 (1H, d, J=6,9 Hz),
7,40 - 7,43 (3H, m), 7,61 - 7,64 (2H, m), 7,84 (1H, d, J=8,l
Hz), 8,07 (1H, dd, J=8,< | 1, 1,8 Hz), 8,57 (1H, dd, J=l,8 Hz). | |||
IČ (CHC13): 3380, 3254, | 2952, | 2880, | 2212, 1707, | 1606, 1531, |
1493, 1409, 1344, 1166. | ||||
ía]D = +23,4° (CHC13, c= | =1,00, | 25,0 | °C) . |
Č. la-51 |
CDC13 300 MHz |
0,95 - 1,98 (14H, m), 2,23 (1H, m), 2,30 (2H, t, J=7,2 Hz), |
3,00 (1H, tn) , 3,66 (3H, s) , 4,56 (2H, š) , 4,70 (1H, d, J=6,9 |
Hz), 5,20 - 5,29 (2H, m), 7,15 (1H, dd, J=7,8, 1,8 Hz), 7,23 |
(1H, d, J=l,8 Hz), 7,36 - 7,39 (3H, m), 7,46 (1H, d, J=7,8 |
Hz) , 7,53 - 7,56 (2H, m) . |
IČ (CHC13): 3494, 3386, 3028, 2952, 2874, 1725, 1611, 1559, |
1497, 1422, 1317, 1162/cm. |
Č. la-52 |
CDC13 300 MHz |
0,96 - 2,04 (16H, m) , 2,20 (1H, m), 2,36 (2H, t, J=6,9 Hz), |
2,99 (1H, m), 5,17 (1H, d, J=6,3Hz), 5,28 - 5,31 (2H, m),
7,18 (ÍH, dd, J=9,6, 1,8 Hz), 7,25 (1H, m), 7,36 - 7,39 (3H, m), 7,46 (1H, d, J=7,8 Hz), 7,52 - 7,56 (2H, m).
IČ (CHCI3): 3482, 3378, 3260, 3022, 2948, 2868, 1708, 1612, 1495, 1422, 1317/cm.
[a]D = +15,0° (CHC13, c=1,00, 24,0 °C) .
Č. la-53
CDC13 300 MHz
1,0 - 2,05 (15H, m) , 2,31 (2H, t, J=7,2 Hz),
3,10 (1H, m),
3,67 (3H, s), 5,02 (1H, Š), 5,26 - 5,33 (2H, m), 7,18 (1H, d,
J=4,2 Hz), 7,36 - 7,39 (3H, m), 7,48 (1H, d, j~4,2 Hz), 7,51
- 7,55 (2H, m).
IČ (CHC13): 3372, 3270, 3018, 3004, 2946, 2868, 2202, 1726,
1486, 1433, 1336, 1154/cm.
[a]D = + 0,6° (CHC13, c=1,11, 25,0 °C) .
······ · · « ·· ·· • · · · · · · · · · ·
115 ·· ··· · · · · · · · · ······· ··· • · ·· · · · · · · · ·· ία]436 = +17,8° (CHCly, C=l,ll, 25 °C) Č. la-54
CDC13 300 MHz
0,99 - 2,11 (14H, m), 2,27 (ÍH, m), 2,37 (2H, t, J=7,5 Hz),
3,13 (1H, m), 5,16 (ÍH, d, J=6,6 Hz), 5,31 - 5,35 (2H, m),
7,18 (ÍH, d, J=3,6 Hz), 7,37 - 7,39 (3H, m), 7,50 (ÍH, d, J=3,6 Hz), 7,52 - 7,55 (2Ή, m).
IČ (CHC13): 3484, 3370, 3246, 2948, 2868, 2202, 1708, 1486, 1429, 1335, 1153/cm.
[tt]D = +17,8° (CHC13, c=l,00, 24,0 °C).
teplota tání 95 až 96 °C.
Č. la-55
CDC13 300 MHz
0,95 - 1,92 (14H, m), 2,15 (1H, m), 2,24 (2H, t, J=7,5 Hz), 3,00 (ÍH, m), 3,66 (3H, s), 5,10 - 5,30 (3H, m), 7,40 - 7,60 (7H, m), 7,70 (1H, d, J=7,8 Hz), 8,08 (ÍH, d, J=8,l Hz).
IČ (CHC13): 3356, 3020, 2948, 2868, 2210, 1727, 1437, 1341, 1165/ctn. [a]D = -58,4° (CHC13, c=l,00, 26,0 °C). teplota tání 84 až 85 °C. | 1490, 1458, | ||
Č. la-56 | |||
CDC13 300 MHz | |||
0,95 - 1,95 (14H, m) , | 2,10 (ÍH, m), 2,27 | (2H, t, | J=6,9 Hz), |
3,00 (1H, m) , 5,17 - í | j,21 (2H, m) , 5,38 | (ÍH, d, | J=6,9 Hz), |
7,39 - 7,60 (7H, m), 7,70 (ÍH, dd, J=7,8, J=6,6, 1,5 Hz). IČ (CHC13): 3364, 3026, 2952, 2874, 2212, 1458, 1411, 1341, 1164/cm. | 1,5 Hz), 8,07 (ÍH, | |||
1707, | 1597, | 1491, | ||
[a]D = -43,1° (CHC13, c=l,00, 25,0 | °C) . | |||
Č. la-57 | ||||
CDC13 300 MHz | ||||
0,99 - 1,97 (T4H, m), 2,23 - 2,30 | (3H, m) | , 3,01 | (ÍH, | m) , 3,67 |
116 (3H, s), 5,17 - (5,26 3H, m) , 7,36 - 7,38 (3H, m), 7,50 - 7,56 (3H, m), 7,60 (1H, m), 7,83 (1H, m) , 8,05 (1H, m) .
IČ (CHC13): 3376, 3020, 2946, 2870, 1727, 1598, 1491, 1437, 1412, 1330, 1245, 1163/cm.
[a]D = -12,7° (CHC13, c-1,00, 24,0 °C) .
Č. la-58
CDC13 300 MHz
0,97 - 1,98 (14H, m), 2,20 (1H, m), 2,33 (2H, t, J=6,9 Hz), 3,02 (1H, m), 5,19 - 5,28 (3H, m), 7,36 - 7,38 (3H, m), 7,47
- 7,55 (3H, ni), 7,69 (1H, m) , 7,83 (1H, m) , 8,04 (1H, m) .
IČ (CHC13): 3376, 3260, 3022, 3002, 2948, 2868, 2220, 1708, 1598, 1490, 1455, 1412, 1327, 1162/cm.
[θ'] D -8,6° (CHC13, C=l,01, 24,0 °C) .
Č. la-59
CDC13 300 MHz
0,95 - 1,99 (24H, m) , 2,20 (1H, m) , 2,28 (2H, t, J=7,8 Hz), 2,53 (1H, s), 2,96 (1H, m), 3,69 (3H, s), 4,99 (1H, d, J-6,6 HZ), 5,18 - 5,20 (2H, m), 7,53 (2H, d, J=8,4 Hz), 7,82 (2H, d, J=8,4 Hz) .
IČ (CHC13): 3583, 3376, 3002, 2936, 2852, 1725, 1591, 1490, 1437, 1393, 1325, 1160/cm.
[a]D = -8,8° (CHC13, c=1,00, 24,0 °C).
Č. la-60
CDC13 300 MHz
0,96 - 2,05 (24H, m), 2,22 (1H, m), 2,33 (2H, m), 2,88 (1H, m), 5,22 - 5,26 (2H, m) , 5,30 (1H, d, J=5,7 Hz), 7,50 (2H, d, J=8,7 Hz), 7,80 (2H, d, J=8,7 Hz).
IČ (CHC13): 3376, 3260, 3022, 2936, 2852, 1710, 1592, 1491, 1452, 1395, 1325, 1159/cm.
[Of]D = -8,9° (CHC13, c=1,06, 24,0 °C) .
teplota tání 88 až 91 °C.
Č. la-61
117
CDC13 300 MHZ
0,95 - 2,24 (23H, m, 2,29 (2H, m) , 2,99 (1H, m), 3,69 (3H,
S), 4,76 (1H, d, J=6,3 Hz), 5,21 - 5,24 (2H, m) , 6,28 (1H,
m), 7,50 - 7,53 (2H, m) , 7,77 - 7,80 (2H, m).
IČ (CHC13): 3374, 3270, 3018, 2942, 2868, 2196, 1726, 1589, 1490, 1435, 1324, 1158/cm.
[ff)D = +7,7° (CHC13, C=l,02, 24,0 °C).
teplota tání 93 až 95 °C.
Č. 1-62
CDC13 300 MHz
0,96 - 2,45 (23H, m), 2,36 (2H, d, J=6,9 Hz), 2,99 (1H, m),
5,24 (1H, d, J=6,3 Hz), 5,24 - 5,32 (2H, m), 6,28 (1H, m), 7,50 - 7,53 (2H, m) , 7,78 - 7,81 (2H, m) .
IČ (CHC13): 3468, 3374, 3260, 3020, 2942, 2868, 2196, 1598, 1490, 1455, 1398, 1322, 1157/cm.
[a]D = +19,4° (CHC13, C=l,03, 24,0 °C).
Č. la-63
CDC13 300 MHz
0,93 - 1,95 (25H, m), 2,16 (1H, m), 2,29 (2H, t, J=7,2 Hz), 2,43 (2H, t, J=6,9 Hz), 2,94 (1H, m), 3,69 (3H, s), 4,95 (1H, d, J=6,9 Hz), 5,21 - 5,24 (2H, m), 7,49 (2H, d, J=8,7 Hz), 7,79 (2H, J=8,7 Hz).
IČ (CHC13): 3376, 3018, 2946, 2866, 2222, 1727, 1592, 1456, 1435, 1325, 1158/cm.
[a]D = +3,7° (CHC13, c=l,00, 25,0 °C).
Č. la-64
CDC13 300 MHz
0,93 - 1,97 (26H, m), 2,35 (2H, t, J=7,2 Hz), 2,43 (2H, t, J=7,2 Hz), 3,00 (1H, m), 5,08 (1H, d, J=6,6 Hz), 5,26 - 5,27 (2H, m) , 7,49 (2H, d, J=8,7Hz), 7,78 (2H, d, J=8,7Hz).
IČ (CHC13) : 3260, 3020, 2948, 2864, 2222, 170.8, 1592, 1489, 1456, 1397, 1324, 1156/cm.
[a]D - +14,4° (CHC13, c=l,00, 25,0 °C).
999999 · 9 · 9 9 ··
999 9 9 99 9999
118
999 9 9 9 99999
9999 99 9999 • 9 99 99 999 9999 teplota tání 70 až 71 °C.
Č. la-65
CDC13 300 MHz
0,95 - 1,98 (14H, m), 2,18 (1H, m), 2,30 (2H, t, J=7,2 Hz),
3,00 (1H, m), 3,67 (3H, s) , 4,83 (1H, d, J=6,9 Hz), 5,22 5,25 (2H, m), 5,54 (1H, š), 6,82 - 6,85 (2H, m), 7,42 - 7,45 (2H, m), 7,59 - 7,62 (2H, m), 7,82 - 7,85 (2H, m).
IČ (CHC13): 3576, 3374, 3018, 2946, 2868, 2208, 1725, 1607,
1587, 1514, 1435, 1325, 1270, 1162, 1133/cm.
[o]D = +9,1° (CHC13, c=1,03, 24,0 °C) .
teplota tání 111 až 112 °C.
Č. la-66
CDC13 300 MHz
0,97 - 2,03 (14H, m) , 2,15 (1H, m), 2,35 (2H, t, J=7,5 Hz),
3,00 (1H, m), 5,17 (1H, d, J=6,6 Hz), 5,26 - 5,30 (2H, m),
6,82 - 6,85 (2H, m), 7,42 - 7,45 (2H, m), 7,59 - 7,62 (2H, m) , 7,82 - 7,85 (2H, m) .
IČ (CHC13): 3260, 2948, 2870, 2208, 1709, 1607, 1587, 1514, 1396, 1325, 1162, 1133/cm.
[a]D -21,0° (CHC13, c=l,00, 23,0 °C).
teplota tání 161 až 162 °C.
Č. la-67
CDC13 300 MHz
0,95 - 1,98 (14H, m), 2,20 (1H, m), 2,29 (2H, t, J=7,2 Hz),
3,01 (1H, m), 3,67 (3H, s), 4,82 (1H, d, J=6,6 Hz), 5,19 5,27 (2H, m), 7,05 - 7,10 (2H,m), 7,51 - 7,56 (2H, m), 7,61 - 7,64 (2H, m) , 7,84 - 7,87 (2H, m) .
IČ (CHC13): 3374, 3280, 3020, 2946, 2868, 2214, 1727, 1589,
1509, 1435, 1327, 1233, 1161, 1134/cm.
[cdD = +6-7° (CHC13, 0=1,01, 24,0 °C) .
teplota tání 84 až 85 °C.
119 ······ 99 9 99 99
9 9 9 9 99 9 9 99
9 9 9 9 9 9 99 9
9 9 9 9 9 9 · · 9 · ·· ······· ···
Č. la-68
CDC13 300 MHz
0,96 - 2,01 (14H, m) , 2,15 (1H, m), 2,34 (2H, t, J=6,9 Hz), 3,02 (1H, m), 5,23 - 5,27 (3H, m) , 7,04 - 7,10 (2H, m), 7,51 - 7,56 (2H, m) , 7,61 - 7,64 (2H, m) , 7,85 - 7,88 (2H, m). IČ (CHC13): 3374, 3258, 3020, 2948, 2868, 2214, 1708, 1589, 1509, 1455, 1398, 1322, 1156/cm.
[tt]D = +22,6° (CHC13, e=l,02, 24,0 °C) .
teplota tání 135 až 136 °C.
Č. 13-69
CDC13 300 MHz
0,95 - 1,98 (14H, m) , 2,19 (1H, m), 2,29 (2H, t, J=7,2 Hz), 2,39 (3H, S), 3,01 (1H, m) , 3,69 (3H, S) , 4,80 (1H, d, J=6,6 Hz), 5,20 - 5,29 (2H, m), 7,18 (2H, d, J=8,lHz), 7,44 (2H, d, J=8,l Hz), 7,62 (2H, d, J=8,4 Hz), 7,84 (2H, d, J=8,4 Hz). IČ (CHC13): 3374, 3022, 2946, 2868, 2210, 1727, 1589, 1511, 1436, 1323, 1161, 1133/cm.
[Oř] D = +9,2° (CHC13, C=l,02, 24,0 °C) .
teplota tání 116 až 118 °C.
Č. la-70
CDC13 300 MHz
1,15 | - 2,00 (14H, | m) , 2, | 13 (1H, m) , 2,33 - 2,38 | (5H, m), 3,04 |
(1Ή, | m) , 5,14 (1H, | d, J= | :6,6 Hz) , 5,25 - 5,30 (2H | , m), 7,17 |
(2H, | d, J=7,8 Hz) , | 7,44 | (2H, d, J=7,8 Hz), 7,62 | (2H, ď, J=8,4 |
Hz) , | 7,85 (2H, d, | J=8,4 | Hz) . | |
IČ (CHC13): 3380, | 3260, | 3020, 2948, 2868, 2210, | 1708, 1590, | |
1511, | 1396, 1324, | 1160, | 1133/cm. |
[a]D = +24,6° (CHC13, c=1,00, 24,0 °C).
Č. la-71
CDC13 300 MHz
0, | 95 | - 1,96 | (14H, m), 2, | 19 | (1H, m) , 2 | 1,29 | (2H, t, J=7,2 | Hz) , |
3, | 00 | (1H, m) | , 3,20 (1H, | s) , | 3,65 (3H, | s) , | 4,81 (1H, d, | J=6,6 |
Hz), 5,20 - 5,27 (2H, m) , 7,46 - 7,54 (4H, m) , 7,62 - 7,65 •ΦΦΦΦ* φφ · ·· φ· φφφ φφφ® φφφ
120 • « ··· · · · φφφφ · φφφφ φφφ φφφ (2Η, m) , 7,85 - 7,88 (2Η, mj .
IČ (CHC13): 3374, 3290, 3018, 3002, 2946, 2868, 2212, 2110, 1726, 1591, 1507, 1435, 1401, 1324, 1161/cm.
[α] D = +9,6° (CHC13 , c=1,01, 24,0 °C) .
teplota tání 136 až 138 °C.
Č. la-72
CDC13 | 300 | MHZ | ||
0,96 | - 2, | 01 | (14H, m), 2,14 (1H, m), 2,35 | (2H, t, J--7,2 Hz), |
3,05 | (1H, | m) | , 3,20 (ÍH, s), 5,16 (1H, d, | J=7,2 Hz), 5,26 - |
5,29 | (2H, | m) | , 7,45 - 7,53 (4H, m), 7,63 | (2H, d, J=8,4 Hz), |
7,87 | (2H, | d, | J=8,4 Hz). |
IČ (CHC13): 3462, 3374, 3290, 3024, 2948, 2868, 2212, 2110,
1708, 1591, 1508, 1455, 1401, 1321, 1274, 1160, 1132/cm.
[a] D = +24,3° (CHC13, c=l,03, 24,0 °C) .
teplota tání 96 až 99 °C.
Č. la-73
CDC13 300 MHz
0,95 - 1,98 (14H, m), 2,19 (1H, m) , 2,27 - 2,32 (5H, m) , 3,01 (1H, m) , 3,67 (3H, s) , 4,80 1H, d, J=6,6 Hz), 5,20 - 5,27 (2H, m), 7,12 (2H, m), 7,56 (2H, m) , 7,63 (2H, m) , 7,84 (2H, m) .
IČ (CHC13): 3374, 3276, 3018, 2946, 2868, 2214, 1762, 1730, 1589, 1506, 1435, 1368, 1161/cm.
[a]D = +7,8° (CHC13, C=l,02, 24,0 °C) .
teplota tání 102 až 104 °C.
Č. la-74
CDC13 300 MHz
0,95 - 2,05 (14H, m) , 2,15 (1H, m), 2,32 - 2,37 (5H, m), 3,02
(1H, m), 5,14 (1H, | d, J | =6,6 Hz), 5,26 - 5, | 30 (2H, m), | 7,10 - | |
7,13 (2H, m) | , 7,54 | - 7, | 57 (2H, m), 7,62 - | 7,64 (2H, m) | , 7,84 |
- 7,87 (2H, | m) . | ||||
IČ (CHC13) : | 3482, | 3250, | 3022, 2946, 2868, | 2214, 1716, | 1709, |
1589, 1507, | 1454, | 1396, | 1368, 1322, 1195, | 1161/cm. |
• · [a]D = +15,0° (CHC13, c=l,00, 24,0 °C).
teplota tání 129 až 131 °C.
- 121 Č. la-75
CDC13 300 MHz
0,95 - 1,99 (14H, m), 2,20 (1H, m), 2,30 (2H, t, J=7,2 Hz),
3,02 | (1H, m) , 3,67 (3H, s) , | 3,94 (3H, s), | 4,79 | (1H, d. | J=6,6 |
Hz) , | 5,19 - 5,29 (2H, m), 7, | 60 - 7,63 (2H, | m) , | 7,65 - | 7,67 |
(2H, | m), 7,86 - 7,89 (2H, m) | , 8,04 - 8,06 | (2H, | m) . | |
IČ (CHG13): 3378, 3018, 2946 | , 2880, 1720, | 1604, | 1435, | 1307, | |
1276, | 1161, 1106/cm. | ||||
[a]D | = +7,3° (CHCly, c=l,01, | 25,0 °C). |
teplota tání 132 až 133 °C.
Č. la-76
CDC13 + CD3OD 300 MHz
1,04 -2,05 (14H, m), 2,19 (1H, m), 2,32 (2H, t, J=6,9Hz),
2,93 (1H, m) , 5,27 - 5,31 (2H, m), 7,60 - 7,63 (2H, m), 7,65 - 7,68 (2H, m), 7,86 - 7,89 (2H, m), 8,05 - 8,07 (2H, m).
IČ (CHC13): 3402, 3299, 2955, 2876, 2665, 2549, 1455, 1422, 1313, 1281, 1164/cm.
[a]D = -21,1° (CH30H, c=l,03, 23,0 °C) . teplota tání 227 až 229 °C (rozklad).
Č. la-77
CDC13 300 MHz
0,96 - 1,99 (14H, m) , 2,20 (1H, m), 2,30 (2H, t, J=7,2 Hz), 3,02 (1H, m), 3,68 (3H, s), 4,88 (1H, d, J=6,3 Hz), 5,19 -
5,29 (2H, m) | , 7,67 - 7,72 (4H, m), 7,89 - 7,91 (2H, m), 8,24 | |||
- 8,27 (2H, | m) . | |||
IČ (CHC13): | 3376, 3276, | 3020, | 2946, 2870, | 2214, 1726, 1594, |
1519, 1455, | 1435, 1389, | 1344, | 1151/cm. | |
[a]Ď = +7,7° | (CHC13, c= | 1,02). |
teplota tání 87 až 89 °C.
♦ · ·· • · · · • · · · • · · · · • · ·
122 ···· ·♦ ·· • · · · ·· • · · ·· • · ♦ · ·· • · · · · ·
C. la-78
CDC13 300 MHz
0,98 - 2,00 (14H, m) , 2,18 (1H, m), 2,34
3,02 (1H, m) , 5,24 - 5,28 (2H, m) , 5,32 (
7,67 - 7,72 (4H, m) , 7,89 - 7,92 (2H, m) , m) .
IČ CHC13): 3374, 3260, 2948, 2214, 1708, [a]D = +23,3° (CHC13, c=l,00).
teplota tání 102 až 103 °C.
1595, 1344, 1160/cm.
C. la-79
CDC13 300 MHz
0,93 - 2,02 {14H, m),
3,05 (1H, m) ,
m) , 6,88 (2H, m) ,
IČ (CHG1?): 3380, 1511, (a]D = +26,7° (CHC13, teplota tání 75 až 77
2,13 (1H, m), 2,36
3,84 (3H, S), 5,18 (1H, ě), - 6,91 (2H, m) , 7,48 - 7,50 (2H, 7,83 - 7,85 (2H, m).
3): 3360, 3252, 3020, 2950, 2868, 1457, 1396, 1321, 1286, 1160/cm.
C=l,00).
°c.
(2H, t, J=7,1 Hz),
5,27 - 5,31 (2H,
m) , 7,60- 7,63
2208, 1708, 1589,
C. la-80
- 1,99 (14H, m) , (1H, m) , 3,68 (3H, s), (2H, m) , 7,51 - 7,77 (5H, m) .
2,21 (1H, m) , 2,30 (2H, t, □
4,80 (1H, d, J=6,6 Hz)
TO) , 7,87 - 7,90 (2B
CDC13 300 MHz
0,96
3,02
5,28 (1H,
IČ (CHC13): 3374, 3270, 3018, 1567, 1527, 1495, 1456, 1436, [q?]d = +7,4° (CHC13, c=1,00, teplota tání 68 až 70 °C.
2868,
1296,
22,0 °C) .
2946,
1344,
2216, 1726, 1607,
1161/cm.
Č. la-81
CDC13 300 MHz
0,97 - 2,01 (14H, m), 2,16 (1H, m) , 2,34
3,01 (1H, m), 5,22 - 5,28 (3Ή, m), 7,51 (1H, m), 7,65 (1H, (2H, t, J=7,2 HZ),
m) , 7,70 - 7,76 (3H, m), 7,88 - 7,91 (2H, m) , 8,12 (1H, dd,
J=6,9 Hz), 1,5 Hz).
IČ (CHC13): 3480, 3382, 3262, 3026, 2952, 2872, 2218, 1708,
1607, 1567, 1526, 1396, 1343, 1225, 1160/cm.
[a]D = +22,0° (CHC13, c=l,00).
teplota tání 92 až 94 °C.
123
Č. la-82
CDC13 300 MHz
0,95 - 1,98 (T4H, m) , 2,20 (1H, m) ,
2,29 (2H, t, J=7,2Hz),
3,01 | (1H, | m) , | 3,67 (3H, s), 4,30 (2H-, Š) , | 4,79 | (1H, | d, J=6,9 |
Hz) , | 5,20 | - 5 | ,29 (2H, m), 6,71 - 6,76 (2H, | m) , | 7,18 | (1H, m) , |
7,37 | (1H, | dd, | J=7,8, 1,2 Hz), 7,61 - 7,65 | (2H, | m) , | 7,83 - |
7,87 | (2H, | m) . |
IČ (CHC13): 3376, 3020, 2946, 2868, 2202, 1725, 1613, 1589, 1484, 1454, 1315, 1253, 1161/cm.
[a] D = +8,9° (CHC13, c=l,00, 22,0 °C) . teplota tání 68 až 70 PC.
Č. la-83
CDC13 300 MHz 0,97 - 1,99 (14H, m), 2,17 (1H, m), | 2,33 (2H, t, J=6,9 Hz) , | |||
2,99 (1H, m), 5,20 - 5,28 (2H, | m) , | 5,37 (1H, | d, | J=6,9 Hz), |
6,45 (2H, š) , 6,71 - 6,76 (2H, | m) , | 7,19 (1H, | dd, | J=7,8, 6,6 |
Hz), 7,37 (1H, m), 7,62 (2H, d | , J=8 | ,4 Hz), 7, | 85 | (2H, d, J=8,4 |
Hz) . | ||||
IČ (CHC13): 3478, 3378, 3260, | 3022, | 2950, 2868, | 2204, 1708, | |
1613, 1589, 1484, 1454, 1396, | 1316, | 1160/cm. | ||
[a]D = +17,1° (CHC13, c=l,01). |
Č. la-84
(1H, dt, J=8,l Hz), 8,04 (1H, dd, J=8,l & 1,8 Hz), 8,57 (1H,
124 d, J=2,1 Hz).
IČ (CHC13) : 3492, 3254, 3028, 2954, 2202, 1708, 1597, 1512, 1344, 1291, 1250/cm.
[a]D - +27,4° (CHC13, C-0,53, 23,0 °Cj .
Č. la-85
CDC13 300 MHz
0,96 - 2,05 (14H, m), 2,20 (1H, m), 2,35 (2H, t, J=6,9 Hz),
2,99 (1H, m), 3,84 (3H, s), 5,22 - 5,31 (3H, m), 6,89 (2H, d, J=8,7 Hz), 7,19 (1H, šs), 7,29 (1H, šs), 7,45 - 7,50 (3H, m) . IČ (CHC13): 3478, 3378, 3020, 2950, 2868, 2202, 1708, 1606, 1511, 1421, 1311, 1287, 1248, 1155/cm.
[tt]D = +17,1° (CHC13, c=l,00, 23,0 °C) .
Č. la-86
CDC13 300 MHz
1,03 - 2.05 (14H, m), 2,21 (lH,m), 2,37 (2H, t, J=6,9 Hz),
3,04 (lH,m), 5,29 - 5,33 (2H, m), 5,57 (1H, d, J=6,3 Hz),
6,84 - 6,87 (2H, m), 7,50 - 7,53 (2H, m), 7,79 (1H, d, J=8,l Hz), 8,03 (1H, d, d, J=l,5 a 8,1 Hz), 8,57 (1H, d, J=l,5 Hž). IČ (CHC13): 3250, 3024, 2950, 2868, 2200, 1707, 1515, 1344, 1271, 1166, 1143/cm.
[a]D = +21,2° (CHC13, c=0,26, 22,0 °C).
Č. la-87
CD3OD 300 MHz
1,04 - 2,00 (14H, m) , 2,18 (1H, m) , 2,26 (2H, t, J=5,4 Hz),
2,93 (1H, m), 5,19 - 5,24 (2H, m) , 6,77 - 6,80 (2H, m), 7,05 (1H, dd, J=2,l a 8,1 Hz), 7,22 (1H, d, J=2,l Hz), 7,38 - 7,42 (3H, m).
IČ (CHC13): 3377, 2952, 2873, 2204, 1705, 1607, 1515, 1425, 1312, 1267, 1222, 1153/cm.
[tt]D = -15,6° (CHC13, c=1,02, 22,0 °C).
125
Č. la-88
CDCI3 300 MHz
0,90 - 1,96 (14H, m), 2,22 - 2,31 (3H, m) , 2,95 (lH,m), 3,65 (3H, s), 4,87 (1Ή, d, J = 6,6 Hz), 5,13 - 5,28 (2H, m) , 7,46 7,62 (3H, m) , 7,82 - 7,89 (4H, m) , 7,90 - 7,96 (2H, m) , 8,42 (1H, šs).
IČ (CHC13): 3376, 3016, 2946, 2868, 1720, 1677, 1592, 1514, 1498, 1429, 1376, 1314, 1241, 1156, 1094/cm.
[a]D = -10,7° (CHC13, c=1,04, 22,0 °C) .
teplota tání 134 až 136 °C.
Č. la-89
CDC13 + CD3OD 300 MHz
0,96 - 2,08 (14H, m) , 2,23 (1H, m) , 2,28 (2H, t, J=7,2 Hz),
2,89 (1H, m), 5,20 - 5,32 (2H, m) , 7,46 - 7,62 (3H, m), 7,82
- 7,97 (6H, m).
IČ (KBr): 3272, 3007, 2952, 2874, 1708, 1660, 1592, 1527,
1498, 1433, 1400, 1317, 1260, 1152, 1094/cm.
[θ']D = -24,4° (CH3OH, c=l,02, 25,0 6C) .
Č. la-90
CDC13 300 MHz
0,89 - 1,96 (14H, m) , 2,23 - 2,33 (3H, m), 2,92 (1H, m), 3,67 (3H, s), 4,85 (1H, d, J-6,3 Hz), 5,10 - 5,25 (2H, m), 7,81 -
7,90 (4H, m), 8,10 - 8,18 (2H, m), 8,31 - 8,40 (2H, m), 8,71 (1H, s) .
IČ (CHC13): 3372, 3018, 2946, 2868, 1718, 1685, 1592, 1527, 1436, 1397, 1346, 1318, 1256, 1154, 1099/cm.
[a]D = -16,1° (CHC13, c=1,00, 23,0 °C).
Č. la-91
CDC13 + CD3OD 300 MHz
0,94 -2,02 (14H, m), 2,18 - 2,36 (3H, m), 2,87 (1H, m), 5,15
- 5,30 (2H, m), 7,82 - 7,92 (4H, m), 8,09 - 8,16 (2H, m),
8,30 - 8,37 (2H, m).
IČ (KBr): 3284, 3112, 3006, 2952, 2874, 1707, 1593, 1528, ······ ·« « ♦· ·· ··· ···· « · · ·
1498, 1399, 1348, 1320, 1259, 1153, 1093/cm.
126
9 9 9 9 9 9 9 99 9 99
9 9 9 9 9 9 9 99
99 99 999 ···· [a]D
-26,3° (CH3QH, c=l,01,
22,0 °C).
Č. la-92
CDC13 300 MHz
0,93 - 1,95 (14H, m) , (3H, s), 5,07 (1H, d, (1H, m) , 7,35 - 7,43
2,22 - 2,31 (3H, m) , 2,98 (1H, m) , 3,68
J=6,9 Hz), 5,10 - 5,24 (2H, m) , 7,18 (2H, m), 7,70 (2H, d, J=7,8 Hz), 7,88 8,05 (4Ή, m), 8,50 (1H, šs).
IČ (CHC13): 3382, 3008,
2952, 1720, 1675,
1599, 1525, 1499,
1438, 1321, 1253, 1161, 1087/cm.
[a]D = -16,6° (CHC13, c-1,03, 24,0 °C). teplota tání 100 až 101 °C.
Č. la-93
CDC13 + CD3OD 300 MHz
0,96 - 2,00 (14H, m), 2,18 - 2,35 (3H, m), 2,90 (1H, m), 5,15
- 5,30 (2H, m) , 7,18 (1H, m) , 7,33 - 7,42 (2Η, m), 7,65 7,74 (2H, m) , 7,90 - 8,08 (4H, m) .
IČ (KBr): 3347, 3194, 3011, 2955, 2875, 1706, 1650, 1602, 1544, 1499, 1443, 1325, 1265, 1165, 1091/cm.
[a]D = -19,4° (CH3OH, c=l,00, 24,0 °C).
teplota tání 158 až 159 °C.
Č la-94
CD30D 300 MHz
1,05 - 2,00 (14H, m), 2,14 (1H, m) , 2,23 (2H, t, J=7,2 Hz),
2,98 (1H, m) , 3,80 (3H, s), 5,13 - 5,27 (2H, m), 6,88 - 6,98 (2H, ttl) , 7,54 - 7,64 (2H, m) , 7,94 - 8,12 (4H, m) .
IČ (KBr): 3370, 3006, 2953, 1708, 1649, 1604, 1541, 1512,
1460, 1441, 1414, 1328, 1302, 1248, 1162, 1107, 1090,
1032/cm.
[Od D = -19,1° (CH30H, c=l,01, 24,0 °C) .
Č. la-95
CD30D 300 MHz
127
• 444 • | • 4 • · | • 4 • 4 | 44 | 44 • 4 | 44 4 4 | ||
• | • | • | • 4 4 | • | 4 444 | 4 | 4 |
• · | • | • | 4 4 | 4 | 4 | 4 | 4 |
1,04 - 2,02 (14H, m) , 2,14 (ÍH, m) , 2,23 (2H, t, J=7,2 Hz),
2,93 - 3,02 (7H, m), 5,13 - 5,27 (2H, m) , 6,82 - 6,92 (2H, m) , 7,51 - 7,59 (2H, m) , 7,95 - 8,02 (2Ή, m), 8,04 - 8,11 (2H, m) .
IČ (KBr): 3370, 3006, 2953, 1708, 1649, 1604, 1541, 1512,
1460, 1441, 1414, 1328, 1302, 1248, 1162, 1107, 1090,
1032/cm.
[a]D = -17,6° (CH3OH, c=l,01, 24,0 °C).
Č. la-96
CD3OD 300 MHz
1,05 - 2,02 (14H, m), 2,14 (ÍH, m), 2,23 (2H, t, J=7,2Hz),
2,98 (ÍH, m), 5,13 - 5,27 (2H, m), 6,75 - 6,84 (2H, m) , 7,43 - 7,52 (2H, m), 7,94 - 8,12 (4H, m).
IČ (KBr): 3339, 3197, 2953, 2875, 1707, 1644, 1606, 1541, 1514, 1446, 1325, 1293, 1259, 1240, 1225, 1161, 1091/cm. [ff]D = -18,7° (CH3OH, C=l,00, 24,0 °C) .
teplota tání 193 až 196 °C.
Č. la-97 dg-DMSO 300 MHz
1,05 - 2,08 (15H, m) , 2,15 (2H, t, J=7,5 Hz), 2,89 (1H, m), 5,18 - 5,28 (2H, m), 6,78 - 7,12 (3H, m) , 7,73 (ÍH, dd, J=l,4 a 7,8 Hz), 7,91 - 7,95 (3H, m), 8,14 (2H, d, J=8,4 Hz), 9,71 (ÍH, S) .
IČ (KBr): 3407, 3191, 2953, 1711, 1646, 1614, 1603, 1537, 1457, 1326, 1162, 1151/cm.
[a]D = -20,7° (CH3OH, C=l,01, 21,0 °C) .
Č. la-98
CDC13 300 MHz
0,93 - 2,00 (14H, m), 2,21 (ÍH, m), 2,31 (2H, t, J=7,2 Hz),
2,93 (ÍH, m), 3,84 (3H, s), 3,85 (6H, s), 5,15 | - 5,30 | (2H, | |||
m), 5,45 (ÍH, d, | J=6,3 | Hz), 7,04 (2H, s), | 7,78 | - 7,86 | (2H, |
m) , 7,90 - 7,98 | (2H, m) | , 8,58 (ÍH, S) . | |||
IČ (CHC13): 3264 | , 3008, | 2954, 2874, 1707, | 1670, | 1607, | 1537, |
1506, 1451, 1421, 1308, 1158, 1129, 1088/cm.
[a]D = -7,2° (CHC13, c=1,01, 23,5 °C).
teplota tání 147 až 149 °C.
128
Č. la-99
CD30D 300 MHz
1,04 - 1,98 (14H, m), 2,21 (IH, m), 2,10 (2H, t, J=7,2 Hz),
2,95 (IH, m), 3,76 (3H, s), 3,86 (6H, s) , 5,07 - 5,24 (2H, m), 7,19 (2H, s), 7,99 (2H, d, J=8,7 Hz), 8,13 (IH, d, J=8,7 Hz) .
IČ (KBr): 3354, 3002, 2950, 2874, 1656, 1607, 1570, 1508, 1452, 1413, 1314, 1233, 1185, 1157, 1127, 1092/cm.
[«] D = -20,3° (CH30H, C=l, 00, 23,5 °C) .
Č. la-100
CDC13 300 MHz
1,14 - 1,97 (14H, m) , 2,19 (IH, m), 2,28 (2H, t, J=7,4 Hz),
3,04 (IH, m), 3,69 (3H, s), 5,03 (IH, d, J=6,9 Hz), 5,15 -
5,29 (2H, m), 7,65 (2H, d, J-8,4 Hz), 7,87 (IH, s), 7,98 (2H, d, J=8,4 Hz).
IČ (CHC13): 3386, 3271, 3025, 3015, 2955, 2877, 1755, 1712, 1608, 1331, 1162/cm.
[a]D = -29,4° (CH3OH, c=1,01, 25,0 °C).
- 2,20 (17H, m) , 2,84 (IH, m) , d, J=8,2 Hz), 7,84 {IH, s), 3008, 2952,
Č. la-101 dg-DMSO
1, 00 (2H,
IČ (KBR): 3269, 3065,
1607, 1322, 1157/cm, [a]D = -26,2° (CH3OH,
5,00
7,89 - 7,95
2874, 2763,
C=l,01, 25,0
5,20 (2H, m), 7,78 (3H, m) .
1746, 1707,
Č. la-102 cd3od
1,00 - 2,25 (17H, m), (2H, m), 7,53 (IH, s)
2,92 (IH, s),
7,77 (2Ή, d,
3,64 (3H,
J=8,6 Hz)
I
J=8,6 Hz).
IČ (KBr) : 3430, 3277, 3006, 2952, 2873, 1720, 1687, 1620,
1571, 1438, 1312, 1156/cm.
[ff]D = -27,3° (CH3OH, c=0,51, 26,0 °C) .
teplota tání 230 až 232 °C.
129
Č. la-103
CDC13 300 MHz
0,94 - 1,96 (14H, m) , 2,19 (1H, m), 2,28 (2H, t, J=7,2 Hz),
3,04 (1H, m), 3,69 (3H, s), 5,11 (1H, d, J=6,6 Hz), 5,15 5,28 (2H, m), 7,60 (2H, d, J=8,4 Hz), 7,67 (1H, sj, 7,98 (2H, d, J=8,4 Hz).
IČ (CHClj): 3381, 3021, 2955, 2876, 1735, 1605, 1437, 1411, 1325, 1231, 1177/cm.
[a]D = +8,6° (CHC13, C=l,00, 23,0 GC).
Č. la-104
CDC13 300 MHz
0,94 - 1,96
2,99 (1H, m)
7,61 (2H, d,
IČ (CHC13):
1604, 1412, [a)D = +10,4° (14H, m) , 2,21 (1H, m) , 2,31 (2H, t, , 5,18 - 5,28 (2H, m), 5,45 (1H, d,
7,99 (2H, 2957, 2876, 1162/cm.
°C) .
5,28 (2H, m),
J=8,7 Hz),
3382, 3222,
1322, 1301, (chci3,
7,67
3028,
1286, c=l,02, (1H, s),
3019,
1179, 23,0
J=6,8 Hz), J-6,6 Hz), d, J=8,7 Hz). 1736, 1709,
Č. la-105
CDC13 300 MHz
0,92 - 1,98 (14H, m),
3,01 (1H, m), 3,69 (3H,
Hz), 5,14 - 5,30 (2H, d, J=8,7 Hz), 8,09 (1H,
IČ (CHC13): 3385, 3284,
1598, 1459, 1438, 1403, [a]D = +3,6° (CHC13, c=1,00,
2,17 (1H, m), s) ,
m) , 7,71 (2H,
s) .
3025,
4,01 (3H,
2,26 (2H, d, J=7,5 s), 4,84 (1H, d, d, J=8,7 Hz), 7,87
3015,
1160,
26,0 GC).
Hz) ,
J=6,3 (2H,
2954, 2877, 2821, 1730, 1052/cm.
1341,
- 130
Č. la-106
CDC13 300 MHz
0,92 - 2,08 (14H, | m) , 2,14 (1H, m) , | 2,34 (2H, d, J=7,2 Hz), | |||||
3,02 | (1H, m) | , 4,01 | (3H, | s) , 5 | ,19 (1H | [, d, J-6,9 | Hz), 5,23 - |
5,32 | (2H, m) | , 7,71 | (2H, | d, J= | 8,4 Hz) | , 7,88 (2H, | d, J=8,4 Hz), |
8,09 | (1H, S) | • | |||||
IČ (CHC13): | 3510, | 3384, | 3268, | 3028, | 3021, 3014, | 2957, 2877, | |
2821, | 2667, | 2666, | 1707, | 1598, | 1459, | 1404, 1341, | 1324, 1160, |
1052/cm.
[a]D = +11,8° (CHC13, c=l,01, 25,0 °C). teplota tání 95 až 96 °C.
Č. la-107
CDC13 300 MHz
0,92 - 1,97 (14H, m) , 1,34 (3H, t, J=7,2Hz), 2,18 (1H, m),
2,28 (2H, d, J=7,4 Hz), 3,01 (1H, m), 3,68 (3H, s), 4,26 (2H, q, J=7,2 Hz), 4,86 (1H, d, J=6,6 Hz), 5,15 - 5,29 (2H, m) , 7, 71 (2H, d, J=8,7 Hz), 7,87 (2H, d, J=8,7 Hz), 8,09 (1H, s). IČ (CHC13): 3385, 3282, 3025, 3026, 3015, 2954, 2877, 1729, 1599, 1480, 1458, 1438, 1403, 1338, 1161/cm.
[a]D = +4,4° (CHC13, 0=1,00, 25,0 °C).
Č. la-108
CDC13 300 MHz
0,90 - 2,04 (14Η, m), 1,34 (3H, t, J=7,2 Hz), 2,14 (1H, m),
2,34 (2H, d, J=7,l Hz), 3,01 (1H, m), 4,27 (2H, q, J=7,2 Hz),
5,20 (1H,, d, J=6,6 Hz), 5,21 - 5,35 (2H, m) , 7,71 (2H, d, J=8,4 Hz) , 7,88 (2H, d, J=8,4 Hz), 8,10 (1H, s) .
IČ (CHC13): 3514, 3384, 3270, 3025, 3015, 3015, 2957, 2877, 1708, 1599, 1458, 1403, 1324, 1324, 1160, 1050/cm.
[cdD = +12,7° (CHC13, 0=1,00, 25,0 °C) .
Č. la-109 [cdD = +8,5° (CHC13, c=l,00, 25,0 °C) .
teplota tání 109,0 až 111,0 °C
131
Č. la-110
CDC13:CD3OD (95:5)
0,92 - 2,06 (14H, m) , 2,20 (1H, m), 2,30 (2H, d, J=7,2 Hz),
2,99 (1H, m), 5,22 - 5,33 (2H, m), 7,54 -7,66 (3H, m), 8,07
(2H, d, J-9, | 0 Hz), 8,12 | - 8,20 | (2H, | m) , 8,29 (2H, d, J=9,0 |
Hz) . | ||||
IČ (Nujol): | 3270, 2956, | 2924, | 2 854, | 1716, 1548, 1485, 1319, |
1167/cm. | ||||
ícdD = +17,0 | 0 (CHC13, c= | 1,00, | 25,0 | °C) . |
teplota tání 166,5 až 168 °C.
Č. la-111 [cdD = +2,6° (CHC13, g=1,00, 24,0 °C) . teplota tání 120,0 až 121,0 °C.
Č la-112
CDC13 300 MHz
0,96 - 2,04 (14H, m), 2,19 (1H, m), 2,33 (2H, d, J=7,lHz),
3,07 (1H, m), 5,28 - 5,31 (2H, m), 5,33 (1H, d, J=6,6 Hz),
7,54 - 7,63 (3H, m), 8,05 (2H, d, J=8,4 Hz), 8,18 - 8,23 (2H, m) , 8,41 (2H, d, J=8,4 Hz).
IČ (CHC13): 3384, 3269, 3025, 3015, 2957, 2877, 1708, 1598, 1496, 1457, 1417, 1326, 1164/cm.
[a]D = +12,2° (CHC13, c=1,00, 24,0 °C).
teplota tání 163 až 164 °C.
Č. la-113 [a]D = +22,1° (CHC13, c=1,05, 25,0 °C).
teplota tání 90 až 92 QC.
Č. la-114 [a]D = +2,2° (CHC13, c=l,02, 25,0 °C).
Č. la-115
CDC13 300 MHz
0,90 - 1,98 (14H, m), 2,15 - 2,22 (1H, m), 2,27 (2H, t, J=7,2
132
Hz ) , | 2,95 - | 3,04 | (1H, m) | , 3,68 | (3H, | S), 4,04 (2H, S), 4,85 |
(1H, | d, J=6, | ,6 Hz) | , 5,10 | - 5,27 | (2H, | m) , 7,12 - 7,34 (7H, m), |
7,76 | - 7,82 | (2H, | m) . | |||
IČ (CHC13): | 3384, | 3026, | 2952, | 1727, | 1595, 1493, 1436, 1318, |
1155, 1091, 890/cm.
[θ'] D = 0° (0^436 = +4,9 + 0,4° (CHC13, c-1,05, 23 °C) .
Č. la-116
cdci3 | 300 | MHz | |||
0,90 - | 2, | 10 (14H, | m) , 2,10 - 2, | 18 (1H, | m), 2,32 (2H, t, J=7,2 |
Hz) , 2 | ,96 | - 3,04 | (1H, m), 4,04 | (2H, s) | , 5,14 (1H, d, J=6,6 |
Hz) , 5 | ,16 | - 5,28 | (2H, m) , 7,12 | - 7,34 | (7H, m), 7,76 - 7,82 |
(2H, m) .
IČ (CHC13) : 3260, 3020, 2950, 1709, 1407, 1318, 1154, 1091, 892/cm.
[a]D = +9,1 i 0,5° (CHC13, c=1,04, 23,0 °C).
Č. la-117
CD3OD 300 MHz
0,92 - 2,18 (17H, m), 2,89 - 2,92 (1H, m), 4,05 (2H, s), 4,95 -5,22 (2H, m), 7,15 - 7,42 (7H, m) , 7,75 - 7,81 (2H, m).
IČ (KBr); 3429, 3279, 2951, 2872, 1563, 1494, 1453, 1408, 1313, 1155, 1093, 1057/cm.
[a]D = -16,3 ± 0,5° (CHC13, c=l,06, 25,0 °C).
Č. la-118
CDC13 300 MHz
0,98 - 1,70 (15H, m) , 1,80 - 2,00 (5H, m) , 2,20 - 2,40 (3H,
m) , 2,98 (1H, m) , 4,06 (2H, s), 4,72 (1H, d, J=6,3 Hz) , 5,00
- 5,23 (3H, m) , 7,16 (2H, d, J=8,4 Hz), 7,26 - 7,33 (5H, m),
7,79 (2H, d, J=8,l Hz),
IČ CHC13): 3376, 3020, 2948, 2868, 1716, 1596, 1492, 1453, 1407, 1318, 1155, 1105/cm.
[tt]D = +2,4° (CHC13, c=1,08, 24,0 °C).
133
Č. ia-119
CDC13 300 MHz
0,90 - 2,02 (14H, m) , 2,20 (1Ή, m), 2,29 (2H, t, J=7,2 Hz),
3,00 (1H, m), 3,68 (3H, s), 4,86 (1H, d, J=6,9 Hz), 5,13 5,34 (2H, m) , 7,00 - 7,09 (4H, m), 7,22 (1H, m) , 7,37 - 7,45 (2H, m), 7,79 - 7,86 (2H, m).
IČ (CHC13): 3376, 3018, 2946, 2868, 1727, 1582, 1486, 1321, 1243, 1151, 1093/cm.
[a]D = +4,5° (CHC13, C-1,05, 23,5 °C).
Č. la-120
CD3OD 300 MHz
1,00 - 2,00 (14H, m) , 2,13 (2H, t, J=7,5 Hz), 2,16 (1H, m) ,
2,91 (1H, m) , 5,05 - 5,33 (2H, m), 7,04 - 7,11 (4H, m), 7,18 - 7,25 (1H, m) , 7,38 - 7,48 (2H, m), 7,80 - 7,87 (2H, m).
IČ (KBr): 3430, 3278, 3006, 2952, 2873, 1583, 1487, 1410, 1322, 1298, 1245, 1152, 1095/cm.
[a]D = -8,8° (CH3OH, c=l,05, 25,0 °C).
Č. la-121
CDC13 300 MHz
0,90 - 2,10 (14H, m) , 2,15 (1H, m) , 2,35 (2H, t, J=7,2 Hz), 3,01 (1H, m) , 5,20 (1H, d, J=6,9 Hz), 5,22 - 5,35 (2H, m) , 7,00 - 7,09 (4H, m), 7,18 - 7,25 (1H, m), 7,37 - 7,45 (2H, m) , 7,79 - 7,86 (2H, m) .
IČ (CHC13): 3260, 3020, 2948, 2868, 1708, 1582, 1486, 1409, 1321, 1296, 1243, 1151, 1093/cm.
[a]D = +13,1° (CHC13, C=l,04, 24,0 °C).
Č. la-122
CDC13 300 MHz
0,90 - 2,00 (14H, m) , 2,23 (1H, m) , 2,28 (2H, t, J=7,5 Hz),
2,96 (1H, m), 3,67 (3H, s) , 4,69 (1H, d, J=6,6 Hz), 5,15 -
5,32 (2H, m), 6,22 (1H, s), 6,98 - 7,40 (5H, m), 7,30 -7,38 (2H, m) , 7,68 - 7,74 (2H, m).
IČ (CHC13): 3416, 3370, 3018, 2946, 2868, 1725, 1587, 1508,
134
1437, 1400, 1320, 1149, 1094/cm.
[cdD = +6,2° (CHCI3, c=l,04, 25,0 °C).
Č. la-123
CDC13 300 MHz
0,90 - 2,04 (14H, m), 2,18 (1H, m) , 2,33 (2H, t, J=7,2 Hz),
2,96 (1H, m) , 5,04 - 5,35 (3II, m) , 6,98 - 7,12 (3H, m) , 7,12
- 7,20 (2H, m), 7,28 - 7,38 (2H, m) , 7,66 - 7,74 (2H, m) .
IČ (CHC13): 3424, 3270, 3028, 2952, 2872, 1708, 1587, 1508, 1445, 1399, 1320, 1148, 1092/cm.
[a]D = +20,9° (CHC13, c=1,06, 23,0 °C).
Č. la-124
CDC13 300 MHz
0,90 - 2,00 (14H, m), 2,18 (1H, m) , 2,28 (2H, t, J=7,2 Hz), 3,00 (1H, m), 3,14 (3H, s), 3,68 (3H, s), 4,56 (2H, s), 4,84 (1H, d, J=6,3 Hz), 5,10 - 5,29 (2Η, m), 7,16 - 7,26 (4H, m) ,
7,26 | - 7,34 (2Η, m) , 7,78 - 7,84 (2H, m) . | ||
IČ (CHC13): | 3384, 3028, 2952, | 2874, 1727, 1598, 1501, 1435 | |
1410, | 1370, | 1329, 1172, 1148, | 1091/cm. |
[alD | = +2,7 | 0 (CHC13, c-1,09, | 23,0 °C). |
Č. la-125
CDC13 300 MHz
0,90 - 2,00 (14H, m), 2,18 (1H, m) , 2,28 (2H, t, J=7,2 Hz),
2,29 (3H, s), 3,00 (1H, m) , 3,68 (3H, s), 4,04 (2H, s), 4,80 (1H, d, J=6,6 Hz), 5,11 - 5,29 (2H, m) , 6,99 - 7,06 (2H, m),
7,12 - 7,19 (2H, m), 7,31 (2H, d, J=8,l Hz), 7,79 (2H, d, J=8,1 Hz).
IČ (CHC13) : 3382, 3280, 3024, 2950, 2874, 1730, 1596, 1504, .1435, 1407, 1367, 1318, 1196, 1155, 1091/cm.
[a]D = +2,9° (CHC13, c=l,06, 23,0 °C).
Č. la-126
CDC13 300 MHz
0,90 - 2,02 (14H, m), 2,14 (1H, m), 2,29 (3H, s) , 2,32 (2H,
135
t, J=7,2 Hz), 3,01 (1H, m), 4,03 (2H, s) , 5,10 (1H, d, J=6,6
Hz), 5,15 - 5,30 (2H, m), 6,98 - 7,06 (2H, m), 7,11 - 7,18 (2H, m) , 7,30 (2H, d, J=8,l Hz), 7,79 (2H, d, J=8,l Hz).
IČ (CHC13): 3374, 3260, 3020, 2948, 2868, 1749, 1708, 1596, 1504, 1407, 1369, 1317, 1195, 1155, 1091/cm.
[a]D = +10,0° (CHC13, c=1,09, 23,0 °C)
Č. ia-127
CDC13 300 MHz
0,87 - 1,95 (14H, m), 2,18 - 2,32 (3H, m) , 2,95 (1H, m), 3,69 (3H, s), 3,96 (2H, s), 4,79 (1H, d, J=6,6 Hz), 4,97 - 5,17 (2H, m), 5,54 (1H, s), 6,75 - 6,82 (2H, m), 6,97 - 7,05 (2H, m), 7,25 - 7,33 (2H, m), 7,75 - 7,81 (2H, m).
IČ (CHC13): 3382, 3026, 2950, 2874, 1722, 1595, 1511, 1436, 1407, 1317, 1257, 1154, 1090/cm.
[cd D = -2,1° (CHC13, c=1,00, 21,5 °C) .
Č. la-128
CDC13 300 MHz
0,85 - 2,02 (14H, m), 2,18 (1H, m), 2,31 (2H, t, J=7,2 Hz),
2,96 (1H, tn) , 3,95 (2Ή, s) , 5,05 - 5,27 (3H, m) , 6,73 - 6,82 {2H, m), 6,96 - 7,04 (2H, m), 7,25 - 7,32 (2H, m), 7,74 7,81 (2H, m) .
IČ (CHClj): 3262, 3020, 2948, 2868, 1708, 1596, 1511, 1407, 1315, 1242, 1154, 1091/cm.
[<X]D = +4,8° (CHC13, c=1,G4, 22,0 °C) .
Č. la-129
CDC13 300 MHz
0,89 - 1,98 (14H, m), 2,18 (1H, m), 2,27 (2H, t, 1-7,2 Hz),
2,99 (1H, m), 3,68 (3H, s), 3,79 (3H, s), 3,98 (2H, s), 4,81 (1H, d, J=6,6 Hz), 5,10 - 5,27 (2H, m) , 6,81 - 6,87 (2H, m), 7,03 - 7,10 (2H, m), 7,25 - 7,32 (2H, m), 7,75 - 7,82 (2H, m) .
IČ (CHC13): 3382, 3276, 3006, 2950, 2874, 1726, 1609, 1509, 1457, 1436, 1407, 1315, 1244, 1154, 1091, 1033/cm.
•··· ··
- 136 [a] D = +19,3° (CHC13, c=1,05, 23,0 °C) .
Č. la-130
CDC13 300 MHz
0,90 | - 2,00 | (14H, m) , 2 | ,20 (1H, m) , 2,30 (2H, | t, J=7,2 Hz), | |
2,98 | (1H, m) | , 3,69 (3H, | S) , 4 | ,81 (1H, d, J-6, | 6 Hz), 5,12 - |
5,32 | (2H, m) | , 5,46 (1H, | šs) , | 6,84 - 7,01 (6H, | m), 7,76 - 7, |
(2H, | to) . | ||||
IČ (CHC13): | 3380, 3284, | 3024, | 2952, 2874, 1724, 1588, 1504, | ||
1488, | 1436, | 1321, 1296, | 1149, | 1091/cm. | |
[«]D | = +28,9 | ° (CHC13, c | =1,01, | 23,0 °C). |
Č. la-131
CDC13 300 MHz
0,92 - 2,10 (14H, m), 2,18 (1H, m) , 2,34 (2H, t, J=6,9 Hz),
2,96 (1H, m), 5,18 - 5,35 (3H, m), 6,84 - 7,01 (6H, m) , 7,75 - 7,83 (2H, m) .
IČ (CHC13): 3270, 3028, 2952, 2874, 1708, 1589, 1505, 1489, 1456, 1322, 1297, 1238, 1148, 1091/cm.
[a]D = +7,7° (CHC13, 0=1,09, 24,0 °C) .
Č. la-132
CDC13 300 MHz
0,91 - 2,02 (14H, m) , 2,19 (1H, m), 2,29 (2H, t, J=7,2 Hz),
2,99 (1H, m), 3,68 (3H, s), 3,83 (3H, s), 4,82 (1H, d, J=6,6 Hz), 5,14 - 5,33 (2H, m) , 6,90 - 7,04 (6H, m) , 7,76 - 7,83 (2H, m) .
IČ (CHC13): 3384, 3006, 2952, 2874, 1727, 1589, 1502, 1488, 1459, 1438, 1321, 1295, 1231, 1150, 1092, 1033/cm.
(a]D = +3,1° (CHC13, c=l,01, 23,0 °C).
Č. la-133
TLC Rf=0,21 (ethylacetát/n-hexan = 1:1 (0,3 % kys. octová))
Č. la-134
CDC13 300 MHz
137
0,97 - 2,10 (14H, m) , 2,20 (1H, m) , 2,36 (2H, t, J=6,9 Hz),
3,04 (1H, m) , 5,22 - 5,33 (2H, m), 5,41 (1H, d, J=6,6 Hz), 7,02 (1H, d, J=9,0 Hz), 7,09 - 7,13 (2H, m), 7,26 - 7,32 (1H, m) , 7,43 - 7,49 (2H, m), 7,93 (1H, dd, J=2,4 a 9,0 Hz), 8,46 (1H, d, J=2,4 Hz).
IČ (CHC13): 3384, 3270, 3020, 2958, 1709, 1610, 1587, 1537, 1479, 1352, 1271, 1252, 1167/cm.
[a]D = +20,9° (CHC13, c=0,51, 22,0 °C).
Č. la-135
CDC13 300 MHz
0,96 - 2,02 (14H, m) , 2,21 (1H, m) , 2,29 (2H, t, J=7,2 Hz),
3,07 | (1H, | m) , | 3,68 | (3H, s) | , 5,04 (1H, d, J=6,9 | Hz), 5,16 - |
5,33 | (2H, | m) , | 7,48 | - 7,55 | (2H, m) , 7,64 (1H, m) | , 7,76 - 7,82 |
(2Ή, | m) , | 7,88 | - 7, | 94 (2H, | m) , 7,98 - 8,04 (2H, | m) . |
IČ (CHC13): 3384, 3282, 3026, 2952, 2874, 1727, 1663, 1596, 1446, 1396, 1316, 1274, 1163, 1090/cm.
[a]D = +3,1° (CHC13, c=l,03, 22,0 °C). | |
Č. la-136 CDC13 300 MHz 0,95 - 2,05 (14H, m), 2,19 (1H, m), 2,34 (2H, t 3,08 (1H, m), 5,10 - 5,40 (2H, m), 5,35 (1H, d, 7,45 - 7,58 (2H, m), 7,64 (1H, m), 7,74 - 7,84 - 7,95 (2Ή, m), 7,95 - 8,06 (2H, m). IČ (CHC13): 3260, 3018, 2950, 2870, 1708, 1662, | , J=7,2Hz), J=6,8 Hz), (2H, m) , 7,84 1595, 1446, |
1395, 1316, 1274, 1162, 1090/cm. tQ]D = +12,9° (CHC13, C=l,05, 21,5 °C) .
Č. Ia-137
CDC13 300 MHz
0,97 | - 2,04 | {14H, m), 2,27 (1H, m), 2,31 | . (2H, t, J=7,2 | ! Hz) , |
3,07 | (1H, m) | , 3,70 (3H, s), 5,15 - 5,30 | (3H, m), 7,48 | - 7,68 |
(5H, m) , 7,96 - 8,02 (2H, m).
IČ (CHC13): 3382, 3030, 2952, 2878, 1725, 1446, 1329, 1154, 1098/cm.
- 138 -
[a]D = -12,1° (CHC13, C=l,03, 22,0 °G). | |
Č. la-138 | |
CDC13 300 MHz | |
0,95 - 2,04 (14H, m) , | 2,25 (ÍH, m), 2,35 (2H, t, J=7,2 Hz), |
3,08 (ÍH, m), 5,15 - ! | 5,34 (2H, m) , 5,41 (ÍH, d, J=6,6 Hz), |
7,48 - 7,68 (5H, τη) , 7,98 - 8,03 (2Η, τη).
IČ (CHC13): 3370, 3242, 3022, 2950, 2870, 1707, 1445, 1408, 1329, 1154, 1099/cm.
[a]D = -0,6° (CHC13, c=l,06, 21,5 °C).
[a]365 = +30,7° (CHC13, C=l,06, 21,5 °C) .
Č. la-139
CDC13 300 MHz
0,92 - 2,19 (14H, m), 2,27 - 2,34 (3H, m), 3,26 (ÍH, m), 3,65 (3H, s), 4,28 (2H, s) , 4,37 (ÍH, d, J=7,4 Hz), 5,34 - 5,50 (2H, m), 7,37 - 7,62 (9H, m).
IČ (CHC13): 3389, 3294, 3028, 3015, 2954, 2877, 1730, 1600, 1488, 1325, 1151, 1129/cm.
[a]D = -24,8° (CHC13, c=1,01, 24,0 °C).
Č. la-140
CDC13 300 MHz
0,92 - 2,22 (15H, m) , 2,34 (2H, t, J=7,l Hz) , 3,24 (ÍH, m) ,
4,29 (2H, S)
7,36 - 7,62
IČ (CHC13):
1708, 1601, [θ'] j-j = -24,6
, 4,81 (ÍH, d, J=7,4 Hz), 5,32 - 5,52 (2H, m), |
(9H, m) . |
3510, 3388, 3251, 3031, 3015, 2956, 2877, 2668, |
1488, 1318, 1151, 1129/cm. |
° (CHC13, c=l,02, 25,0 °C) . |
Č. la-141
CDC13 300 MHz
0,92 - 2,19 (15H, m), 2,32 (2H, t, J=7,2 Hz), 3,26 (1H, m),
3,65 (3H, s), 4,31 (2H, s), 4,48 (ÍH, d, 0=7,4 Hz), 5,33 5,49 (2H, m) , 7,42 - 7,80 (8H, m) .
IČ (CHC13): 3388, 3285, 3018, 2955, 2877, 2225, 1730, 1597,
ΦΦΦΦ φφ Φ· φ φφ ·· ··· · · ·· ····
139 •« φφφ · φ φ φφφ φ φ ΦΦΦΦ φφφ φφφ
1479, 1320, 1152, 1129/cm.
[α]D = -20,1° (CHC13, c=0,96, 25,0 °C) .
Č. la-142
CDC13 300 MHz
0,92 - 2,22 (15H, m) , 2,35 (2H, t, J-6,8 Hz), 3,25 (1H, τη) ,
4,32 (2H,
7,43 - 7,80 IČ (CHC13): 2225, 1708, I^D
s), 4,86 (1H, (8H, m) .
3512, 3388,
1597, 1479,
-19,3° (CHCI d, J=7,4 Hz), 5,33 - 5,53 (2H, m) ,
3258,
1319, 3, c=l,O9,
3031,
1151,
23,0
3023, 3014, 2956, 2877, 1128/cm.
°C) .
Č la-143
CDC13 300 MHz
1,00 - 1,93 (14H, m), 2,17 (ÍH, m), 2,27 (2H, t, J=7,2 Hz),
3,07 (1H, m), 5,17 - 5,22 (2H, m), 5,36 (1H, d, J=6,9 Hz),
7,77 (1H, d, J=9,0 Hz), 8,11 - 8,17 (2H, m), 8,36 (1H, dd, J-2,1 a 9,0 Hz), 8,51 (1H, d, J=l,8 Hz), 8,65 (1H, d, J=2,l Hz.
IČ (CHC13): 3382, 3266, 3026, 2954, 2874, 1708, 1632, 1585, 1528, 1458, 1419, 1345, 1153/cm.
[a]D = +7,6° (CHC13, c=l,04, 22,0 °C) .
Č. la-144
CDC13 300 MHz
0,95 - 1,90 (14H, m) , 2,17 (1H, m), 2,25 (2H, t, J=7,5 Hz),
3,02 | (1H, m),5,09 | (1H, | d, J=6,6 Hz), 5,15 - 5,21 | (2H, | m) , | |||
6,72 | (1H, d, J=8,4 | Hz) , | 6,85 | (1H, s), 7,54 (1H, | d, | J=8 | ,4 | Hz |
7,72 | (1H, d, J=9,0 | Hz) , | 7,83 | (1H, dd, J=l,8 a 9 | ,0 | Hz ) , | 8, | 32 |
(1Ή, | d, J=l, 8 Hz) . | |||||||
IČ (CHC13): 3380, | 3260, | 3022, | 2948, 2868, 2352, | 1709, | 1636, | |||
1460, | 1425, 1313, | 1291, | 1265, | 1148, 1130/cm. | ||||
[a]D | = +12,9° (CHC13, C | =1,02, | 22,5 °C). |
Č. ia-145
CDC13 300 MHz
- 140
0,97 - 1,90 | (14H, m) , 2, | 15 (1H, m), 2,27 | (2H, t | , J=6,9 Hz), |
3,02 (1H, m) | , 3,08 (6H, | s), 5,12 (1H, d, | J=6,3 | Hz), 5,19 - |
5,25 (2H, m) | , 6,78 - 6,8 | 14 (2H, m) , 7,53 | (1H, d, | J=8,7 Hz), |
7,76 - 7,83 | (2H, m), 8,3 | 0 (1H, d, J=l,8 | Hz) . | |
IČ (CHG13): | 3272, 3030, | 2950, 2874, 1708 | , 1635, | 1601, 1511, |
1457, 1425, | 1357, 1328, | 1151, 1124/cm. |
[a]D = +6,3° (CHC13, C=l,04, 23,0 °C) .
Č. la-146
CDC13 300 MHz
0,95 - 2,00 (14H, m), 2,16 (1H, m) , 2,29 (2H, t, J=7,2 Hz),
3,05 (1H, m), 4,10 (3H, J=6,9 Hz), 7,67 - 7,74 Hz), 8,11 (1H, S), 8,61 IČ (CHC13): 3260, 3020, 1470, 1455, 1349, 1311, 1022/cm.
[a]D = +7,8° (CHC13, c=1,00, 23,0 °C).
5,13 - 5,28 (2H, m) ,
m) , 8,08 (1H, d, J=l, 8 Hz)
2868, 1708,
1149,
S) , (2H, (1H,
2948,
1238, 1174,
1639,
1120,
1606,
1079, (1H, d,
9,0
1528,
1060,
C. la-147
CDC1·
CDC13 300 MHz
0,92 - 1,92 (14H, m), 2,17 (1H, m), 2,25 (2H, t,
3,01 (1H, m), 3,97 (3H, s) , 5,10 - | 5,27 (5H, m), 6,92 (1H, | |||
S), 7,29 (1H, s), 7,52 | (1H, d, J=8, | 7 Hz) , | 7,82 | (1H, dd, J=2,l |
a 8,7 Hz), 8,33 (1H, d, | J :-2,1 Hz) . | |||
IČ (CHG13): 3380, 3264, | 3002, 2950, | 2868, | 1708, | 1634, 1476, |
1452, 1426, 1317, 1264, | 1218, 1169, | 1147, | 1115, | 1068, |
1031/cm. | ||||
[a]D = +5,6° (CHC13, c= | 1,02, 23,0 ° | C) . |
Č. la-148
CDC13 300 MHz
0,90 - 1,98 (14H, m), 2,15 (1H, m), 2,28 (2H, t, J=6,9 Hz),
2,91 (6H, s), 3,03 (1H, m) , 4,01 (3H, s), 5,15 - 5,26 (3H,
m) , 7,18 (1H, s), 7,38 (1H, s) , 7,59 (1H, d, J=8,7 Hz), 7,87 (TH, dd, J=2,l a 8,7 Hz), 8,40 (1H, d, J=2,l Hz).
9
9
1709, 1632, 1602, 1495, 1473,
1121/cm.
23,0 °C).
- 141 IČ (CHC13): 3384, 3266, 2956, 1458, 1430, 1317, 1231, 1148, [a]D = +11,2° (CHC13, C=l,01,
Č. la-149
CDC13 300 MHz
0,99 - 1,90 (14H, m) , 2,17 (1H, m), 2,28 (2H, t, J=7,2 Hz),
3,00 (1H, m), 5,13
5,19 (2H, m), 5,43 (1H, d, J-6,0 Hz),
7,02 (1H, dd,
J=2,4 a 9,0 Hz), 7,38
7,41 (2H, m), 7,58 (1H, d, J=8,7 Hz), 7,96 (1H, dd, J=l,8 a 8,7 Hz), 8,45 (1H, d, J=l,8 Hz).
IČ (CHC13): 3270, 3020, 2948, 2868, 1709, 1601, 1478, 1448 1419, 1315, 1147, 1120/cm.
[a]D = -11,4° {CHC13, c=l,01, 23,0 °C) .
Č. la-150
CDC13 300 MHz
0,97 - 1,88 (14H, mj, 2,12 - 2,31 (3H, m), 2,38 (3H, s), 3,01 (1H, m), 5,14 - 5,19 (2H, m), 5,36 (1H, d, J=6,6 Hz), 7,24 (1H, dd, J=2,4 a 9,0 Hz), 7,59 (1H, d, J=6,3 Hz), 7,66 (1H, d, J=8,7 Hz), 7,72 (1H, d, J±=2,4 Hz) , 8,01 (1H, dd, J=l,8 a
8,7 Hz), 8,49 (1H, d, J=l,8 Hz).
IČ (CHC13): 3470, 3374, 3260, 3018, 2950, 2868, 1709, 1474, 1412, 1370, 1319, 1266, 1162, 1145, 1118/cm.
[a]D = +4,9° (CHC13, c-1,00, 24,0 °G).
Č. la-151
CDC13 300 MHz
0,97 - 1,89 (14H, m), 2,17 (1H, m), 2,25 (2H, t, J=7,2 Hz),
3,03 (1H, m) , 3,92 (3H, s), 5,15 - 5,20 (2H, m), 5,32 (1H, d, J=6,6 Hz), 7,11 {1H, dd, J=2,4 a 9,3 Hz), 7,45 (1H, d, J=2,4 Hz), 7,50 (1H, d, J=9,3 Hz), 7,62 (1H, d, J=8,7 Hz), 7,97 (1H, dd, J=2,l a 8,7 Hz), 8,50 (1H, d, J=2,l Hz).
IČ (CHC13): 3260, 3018, 2948, 1708, 1483, 1454, 1432, 1314, 1287, 1268, 1188, 1169, 1147/cm.
[a]D = +4,9° (CHC13, C=l,01, 23,5 °C) .
- 142
Č. la-152
CDC13 300 MHz
0,98 - 2,04 (14H, m), 2,15 {1H, m), 2,30 (2H, t, J-6,6 Hz),
3,04 (1H, m) , 5,17 - 5,29 (3H, m) , 7,41 (1H, dd, J=l,5 a 8,1
Hz), 7,64 - 7,68 (2H, m) , 7,92 (1H, d, J=8,4 Hz), 8,00 (1H, dd, J=l,8 a 8,4 Hz), 8,49 (1H, d, J=l,8 Hz).
IČ (CHC13): 3266, 3028, 2952, 2872, 1707, 1629, 1591, 1456, 1416, 1318, 1275, 1150/cm.
[θ’] D = +3,2° (CHC13, c=l,04, 23,0 °C) .
Č. la-153
CDC13 300 MHz
0,97 - 1,88 (14H, m), 2,16 (1H, m) , 2,26 (2H, t, J=7,2 Hz), 3,03 (1H, m) , 4,64 -4,65 (2H, m) , 5,16 - 5,50 (5H, tn) , 6,13 1H, m) , 7,14 (1H, dd, J=2,7 a 9,0 Hz), 7,46 - 7,52 (2H, m) , 7,63 (1H, d, J=8,7 Hz), 7,97 (1H, dd, J=l,8 a 8,7 Hz), 8,49 (1H, d, J=l,8 Hz).
IČ (CHC13): 3374, 3260, 3020, 2948, 2868, 1708, 1599, 1478, 1446, 1414, 1314, 1284, 1268, 1184, 1148, 1120/cm.
[cdD = +5,3° (CHC13, 0=1,00, 23,0 °C) .
C. la-154
CDC13 300 MHz
0,99 - 2,00 (15H, m) , 2,26 (2H, 4,07 (3H, s) , 5,23 - 5,27 (2H, 7,20 (1H, s), 7,36 - 7,48 (2H, - 7,93 (1H, m) , 8,52 (1H, s) . IČ (CHC13): 3362, 3257, 3020, 1579, 1488, 1457, 1437, 1413, 1104/cm.
[Qf] D - +19,4° (CHC13, 0=1,01, teplota tání 88 až 90 °C.
t, J=7,2 Hz), 3,03 (ÍH, m) , m), 5,36 (1H, d, J=7,2 Hz), m) , 7,55 - 7,58 (1H, m), 7,91
2948, 2868, 1708, 1637, 1602, 1345, 1318, 1301, 1276, 1182,
25,0 °C) .
Č. la-155
CDC13 300 MHz * ·
- 143
0,92 - 2,02 (14H, m) , 2,15 (1H, m) , 2,31 (2H, t, J=7,2 Hz), 3,01 (1H, m) , 4,10 (2H, š), 5,10 (1H, d, J=6,6 Hz), 5,18 -
5,35 (2H, m), 7,04 - 7,26 (5H, m), 7,67 - 7,76 (2H, m) .
IČ (CHC13): 3266, 3028, 2952, 2952, 2872, 1708, 1599, 1574, 1478, 1457, 1418, 1301, 1258, 1147, 1124, 1101, 1080/cm. [α]365 = +33,4° (CHC13, c=l,00, 23,0 °C).
Č. la-156
CDC13 300 MHz
0,91 - 2,21 (15H, m) , 2,33 (2H, t, J=6,9 Hz), 3,01 (1H, m) , 5,11 (1H, d, J=6,6 Hz), 5,27 - 5,35 (2H, m), 6,85 - 6,96 (5H, τη) , 7,35 (1H, d, J=2,l Hz), 7,42 (1Ή, dd, J=2,l a 8,7 Hz).
IČ (CHC13): 3384, 3263, 2957, 1708, 1587, 1489, 1462, 1416, 1290, 1222, 1151, 1123/cm.
[a]D = +6,4° (CHC13, C=l,00, 23,0 °C).
Č. la-157
0,97 - 1,91 (14H, m), 2,18 (1H, m) , 2,26 (2H, t, J=6,9 Hz), 3,04 (1H, m), 5,18 - 5,26 (3H, m), 7,52 - 7,56 (2H, m), 7,88 - 8,00 (3H, m) , 8,25 (1H, m), 8,69 (1H, m).
IČ (CHC13): 3382, 3268, 2952, 2874, 1707, 1457, 1425, 1409, 1318, 1152/cm.
[a]D = +4,4° (GHC13, c=l,02, 22,0 °C).
Č. la-158
CDC13 300 MHz
1,02 - 1,97 (14H, m), 2,20 (1H, m), 2,29 (2H, t, J=7,2 Hz), 3,06 (1H, m), 5,19 - 5,24 (2H, m) , 5,58 (1H, d, J=6,6 Hz), 7,62 (1H, m) , 7,72 (1H, m) , 7,86 - 7,91 (2H, m) , 7,96 (lil, d, J=7,8 Hz), 8,04 (1H, dd, J=l,5 a 8,1 Hz), 8,34 (1Ή, d, J=l,2 Hz ) .
IČ (CHC13): 3490, 3260, 3020, 2950, 2870, 1707, 1456, 1399, 1312, 1165/cm.
[a]D = -8,3° (CHC13, C=1,00, 23,0 °C).
144
Č. la-159
CDC13 300 MHz
0,92
m) , 3,90 (3H, s),
7,97 (1H, dd, J=l,8 a 7,5 Hz)
- 1,88 (14H, m), 2,13 (1H, m), 2,24 (2H, m), 3,02
3,90 (3H, s), 5,12 - 5,26 (3H, m) , 7,29 - 7,58 (4H, , 8,13 (1H, d, J=7,5 Hz), (1H,
m) ,
8,64
(1H, d, J=l,8 Hz) . |
IČ (CHC13) : 3382, 3266, 3018, 2956, 1708, 1629, 1594, 1476, |
1467, 1325, 1245, 1227, 1158, 1146/cm. |
[<xlD = +14,6° (CHC13, c-1,00, 22,0 °C) . |
Č. la-160 |
CDC13 300 MHz |
0,93 - 1,88 (14H, m) , 2,18 - 2,24 (3Ή, m) , 3,00 (1H, m), 5,08 |
7,33 (1H, m),
8,10
- 5,21 (3H, m), 7,28
7,90 (1H, dd, J=l,5 a 7,8 Hz), 8,64 (2H, m) .
IČ (CHC13): 3465, 3380, 3275, 3020, 1604, 1495, 1473, 1457, 1328, 1240, [a]D - +8,2° (CHC13, c=1,01, 22,0 °C).
7,47 (1H, ď
2957,
1222,
2876,
1156,
1708, 1627,
1149/cm.
Č. la-161
CDC13 300 MHz
0,98 - 1,88 (14H, m)
3,05 <1H,
7,40 (1H, dd, J=l,5
8,12 (1H,
IČ (CHG13): 3478, 3266, 3028, 1323, 1196, 1148/cm.
[a]D - +21,9° (CHC13, c=1,01,
2,17 (1H, m), /
5,16 - 5,20 (2H, m)
7,55 (1H, m) , 7,63
Hz), 8,01 (1H, m)
2,24 , 5,35 (1H, d,
8,06 (2H, t,
1H, d, (1H,
2952,
23,0
2874, 1708,
1454, 1417,
Č.
la-162
CDC13 300 MHz
0,96 - 1,98 (14H, m), 2,02
3,05 (1H, m) , 4,10 (3H, s) ,
J.=7,2 Hz), 7,35 - 7,42 (1H, (1H, m),
5,14 - 5,25 (2H,
m) , 7,51
J=7,2 Hz),
5,41 (1H, d,
m), 7,94 2,25 (2H, t,
m) ,
7,64 (3H,
- 145 • · · ♦
8,00 (1H, m), 8,16 (1H, s).
IČ (CHC13): 3368, 3274, 3028,
1465, 1452, 1438, 1413, 1315,
2952, 2874,
1708, 1633, 1583,
1151, 1103, 1053, 1024/cm.
[O!]d =+15,1® (CHG13, c=1,01, 23,0 °C) teplota tání 108 až 110 °C.
Č. la-163 dg-DMSO 300 MHz
0,97 | - 1,84 (14H, m), | 1,92 (1H, m) | , 2,04 | : (2H, t, | J=7,5 Hz), |
2,90 | (1H, m), 5,08 - | 5,23 (2H, m) , | 7,32 | (1H, s), | 7,38 - 7,61 |
(2H, | m) , 7,62 (1H, s) | , 7,68 - 7,71 | (1H, | m), 7,92 | (1H, s), |
8,14 | - 8,17 (1H, m), | 10,7 (1H, s) , | 11,9 | (1H, s) . | |
IČ (KBr): 3350, 3295, | 2952, 2874, | 1707, | 1636, 1601, 1466, |
1431, 1389, 1315, 1251, 1174, 1146, 1106/cm. íalD = -25,3® (CHC13, c=l,01, 25,0 ®C). teplota tání 159 až 162 °C.
Č. la-164
CDC13 300 MHz
0,98 | - 1,96 | (17H, m) , 2,05 (1H, m), 2,25 (2H, t, J=7,2 Hz), | |||
3,07 | (1H, m) | , 4,32 (2H, | q, J= | 7,2 Hz), 5,19 - 5,23 (2H, | mj , |
5,31 | (1H, d, | J=7,8 Hz), | 7,38 | (TH, m) , 7,41 - 7,62 (3H, | m) , |
7,95 | (TH, m) | , 8,15 (1H, | S) . | ||
IČ (CHC13): | 3360, 3018, | 2946, | 2870, 1709, 1633, 1457, | 1445, | |
1425, | 1394, | 1314, 1176, | 1152, | 1105/cm. | |
[a)D | = +12,7 | ® (CHC13, c | =1,02, | 25,0 °C). | |
teplota tání | 108 až 109 | °C. |
Č. la-165
CDC13 300 MHz
0,95 - 1,98 (15H, m) , 2,26 (2H, t, J=7,5 Hz) , 3,04 (1H, m) , 4,15 (3H, s), 5,20 - 5,26 (2H, m), 5,34 (TH, d, J=6,9 Hz), 7,41 - 7,47 (1H, m), 7,65 - 7,68 (2H, m), 7,89 - 7,92 (TH, m), 8,32 (1H, s).
IČ (CHC13): 3366, 3087, 3022, 2957, 1708, 1632, 1538, 1463, 1408, 1364, 1346, 1308, 1227, 1212, 1205, 1167/cm.
• · • · • · · • · · • · · · · • · · ·· ·· • ·
146 • · [a]D = +19,6° (CHC13, c=1,01, 25,0 °C) .
Č. la-166
2,02 (15H, m),
S), 5,21 s) , dd, (3H, (1H, (1H,
CDC13 300 MHz
0,97
4,14
7, 64
8,47
IČ (CHC13): 3373,
1415, 1345, 1221, [a]D = +14,4° (CHC13,
2,27 (2H, t, .
5,27 (2H, m) ,
7,72 (III, dd, J-0,6 a
J=2,4 a 9,0 Hz), 8,94 2957, 1708, 1639, 1184, 1155/cm.
c-0,50, 25,0
J=6,9 Hz),
5,47 (1H, .9,0 Hz), (1H, dd,
1587,
3,07 (1H, m), d, J=6,9 Hz),
8,25 (1H, s),
J=0,6 a 2,4 Hz)
1428, l
1528, 1467,
Č. la-167
CDC13 300 MHz
0,92 - 2,0 (14H, m), 2,15 (1H, m),
3,04 (1H, m), 3,97 (2H, s) , (2H, m), 7,55 - 7,63 (1H, m), d, J=0,3 HZ) .
IČ (CHC13): 3260, 3020, 2948, 1172, 1144, 1101, 1071/cm.
[a]D = +18,2° (CHC13,
5,15 7,80 c=l,04,
2868,
22,0
1707, 1451, 1413, 1319,
Č.
la-168
CDC13 300 MHz
0,90 - 1,88 (14H, m),
3,00 (1H, m), 5,00 7,25 - 7,30 (1H, m) , a 8,1 Hz), 8,08 IČ (CHC13): 3466, 1458, [a] D
2,16 (1H, m),
5,19 (2H, m) ,
7,48 - 7,50 (2H, m) ,
8,14 (3H, m), 8,93 (1H, 3380, 3276, 3016,
1324, 1241, 1150/cm.
+18,0° (CHC13, c=l,00, 22,0
2,25 (2H, t,
5,35 (1H, d,
7,73 s) .
1708,
J=6,9 Hz),
J=6,6 Hz), (1H, dd, J=l,5
C. la-169
CDC13 300 MHz
0,87 - 1,86 (14H, m), 2,15 (1H, m) ,
2,98 (1H, m) , 3,89 (3H, s) , 5,00 2957, (2H, t,
1630, 1495,
J=6,9 Hz),
5,27 (ÍH, d,
2,25
5,22 (2H, m) ,
147
J=6,9 Jž), 6,88 (1H, dd, | J=2, | 1 a 8,4 Hz) , | 6,94 | (1H, d, J=2,1 |
Hz), 7,69 (1H, dd, J=l,5 | i a 7, | 8 Hz), 7,92 | - 8,01 | (3H, m) , 8,83 |
(1H, s). | ||||
IČ (CHC13): 3465, 3378, | 3276, | 3022, 2957, | 1708, | 1630, 1609, |
1459, 1433, 1314, 1281, | 1229, | 1151/cm. |
[tt]D =+19,3° (CHC13, C=l,01, 21,0 °C).
Č. la-170
CDC13 300 MHz
0,88 -2,25 (17H, m), 3,04 (1H, m), 3,84 (3H, s), 3,95 (3H, s) , 5,06 - 5,26 (3Ή, m) , 6,87 - 6,93 (2H, m) , 7,69 (1H, dd, J=l,6 a 8,2 Hz), 7,93 - 9,05 (3H, m).
IČ (CHC13): 3026, 2957, 1708, 1630, 1601, 1460, 1331, 1243, 1224, 1152/cm.
[cdD = +17,2° (CHC13, 0=1,00, 22,0 °C) .
Č. la-171
CDC13 300 MHz
0,95 - 2,00 (14H, m), 2,16 - 2,32 (3H, m), 2,66 (3H, s), 3,14 (1H, m), 3,68 (3H, s), 5,09 (1H, d, J=6,8 Hz), 5,10 - 5,28 (2H, m), 7,45 (1H, dd, J=l,8 & 8,6 Hz), 7,75 - 7,84 (2H, m). IČ (CHC13): 3374, 3018, 2946, 2868, 1725, 1585, 1513, 1436, 1340, 1278, 1153, 1112/cm.
[Of] D = -14,7° (CHC13, c=l,07, 25,0 °C) .
Č. la-172
CDC13 300 MHz
0,97 - 2,02 (14H, m) , 2,23 (1H, m), 2,28 (2H, t, J=7,2 Hz),
2,66 (3H, s), 3,14 (1H, m) , 5,12 - 5,22 (2H, m), 5,41 (1H, d, J=7,2 Hz), 7,45 (1H, dd, J=2,l & 8,7 Hz), 7,76 (1H, d, J=8,7 Hz), 7,78 (1H, d, J=2,l Hz).
IČ (CHC13): 3372, 3250, 3022, 2950, 2868, 1707, 1514, 1419, 1336, 1279, 1154, 1112/cm.
[o?]D = -4,1° (CHC13, c=l,08, 26,0 °C) .
teplota tání 141 až 143 °C.
····
- 148 Č. la-173
CDCI3 300 MHz
1,15 -2,42 (17H, m), 2,91 (ÍH, m), 5,15 (1H, d, J=4,2 Hz),
5,25 - 5,40 (2H, m), 7,85 (ÍH, t, J=7,2 Hz), 8,00 (ÍH, t, J=8,l Hz), 8,15 - 8,20 (2H, m), 8,67 (ÍH, d, J=8,l Hz), 8,73 (ÍH, d, J=8,l Hz), 8,83 (1H, s), 9,43 (1H, s).
IČ (KBr): 3422, 3269, 3046, 2952, 2871, 1711, 1617, 1447,
1333, 1243, 1161, 1146/cm.
[θ'] D = -41,0° (CHjOH, c=l, 01, 23,0 °C) .
Č. la-174
CDC13 + dg-DMSO 300 MHz
1,00 -1,92 (14H, m), 2,20 (2H, t, J=6,6 Hz), 2,35 (1H, m),
2,92 (ÍH, m), 5,05 - 5,22 (2H, m), 6,63 (ÍH, d, J=5,4 Hz),
7,77 - 7,92 (3H, m), 8,31 (ÍH, dd, J=l,8 a 8,7 Hz), 8,59 (ÍH, d, J=8,7 Hz), 8,73 (ÍH, d, J=8,7 Hz), 9,01 (ÍH, s) , 9,55 (1H, d, J=l,8 Hz).
IČ (KBr): 3433, 3252, 2952, 2871, 1696, 1578, 1423, 1335, 1308, 1219, 1185, 1160, 1106/cm.
[a]D = -19,3° (DMSO, c=0,50, 23,0 °C.
Č. la-175
CDC13 300 MHz
0,96 - 1,87 (14H, m), 2,20 - 2,25 (3H, m) , 2,95 (ÍH, m), 3,66 (3H, s), 4,74 (ÍH, d, J=6,6 Hz) , 5,10 - 5,12 (2H, m) , 6,88
(ÍH, d, J=l,2 Hz), 7,37 | - 7,50 (3H, m), 7 | ,56 (ÍH, dd, | J=8,7, | ||
1,5 Hz), 7,68 - 7,77 (3H | [, m) , | 8,06 | (1H, s | ), 9,44 (ÍH, | dd, |
J=l,2 Hz). | |||||
IČ (CHČ13): 3462, 3374, | 3026, | 3006, | 2952, | 2872, 1274, | 1610, |
1580, 1484, 1452, 1358, | 1309, | 1147. | |||
[a]D = +16,4° (CHC13, C= | 1,05, | 26,0 | °C) . | ||
teplota tání 130 až 132 | °C. |
Č. la-176
CDC13 + CD3OD 300 MHz
1,00 - 2,02 (14H, m), 2,22 (ÍH, m), 2,29 (2H, t, J=6,9 Hz),
149
2,88 | (1H, m), 5,16 - | 5,26 (2H, m) | , 6,87 | (1H, | S) , 7,28 - 7,57 |
(4H, | τη) , 7,69 (1H, d, | J=8,4 Hz), | 7,75 - | 7,78 | (2H, m), 7,99 |
(1H, | s) . | ||||
IČ (KBr): 3254, 2944, | 1704, 1484, | 1453, | 1358, | 1305, 1147. | |
lalD | = +13,0° (CH3OH, | C=l,02, 24, | 0 °G) . | ||
teplota tání 160 až 161 °C. |
Č. la-177
CDC13 300 MHz
0,96 - 1,88 (14H, m), 1,88 - 2,26 (3H, m) , 2,94 (1H, m) , 3,67 (3H, s), 3,87 (3H, s), 4,67 (1H, šs), 5,08 - 5,14 (2H, m),
6,77 (1H, d, J=l,5 Hz), 6,99 - 7,02 (2H, m), 7,53 - 7,57 (1H, m), 7,65 - 7,70 (3H, m), 8,00 (1H, s) , 9,27 (1H, šs) .
IČ (CHC13): 3426, 3376, 3006, 2952, 1724, 1610, 1495, 1438, 1357, 1308, 1282, 1249, 1177, 1147/cm.
[a]D = +18,1° (CHC13, c=l,02, 22,0 ”C).
Č. la-178
CDC13 + CD3OD 300 MHz
0,96 - 1,91 (14H, m) , 2,19 (1H, m), 2,27 (2H, t, J=6,0 Hz), 2,85 (1H, m) , 3,87 (3H, s), 5,16 - 5,23 (2H, m) , 6,99 - 7,02 (2H, m) , 7,41 (1H, m) , 7,64 - 7,73 (3Ή, m) , 7,92 (1H, τη).
IČ (CHC13): 3366, 3261, 3004, 2954, 2873, 1705, 1611, 1496,
1458, | 1438, 1304, 1286, 1253, | 1180, | 1149, | 1128/cm. | ||
[«]D | = +14,6° (CHC13, c=l,02, | 22,0 | °C) . | |||
Č. la | -179 | |||||
cdgi3 | + CD30D 300 MHz | |||||
0,96 | - 1,87 (14H, m), 2,15 - | 2,23 ( | 3H, m) , | 2,93 | (1H, m) , | 3,85 |
(3H, | S), 5,10 - 5,16 (2H, m) , | 6,90 | - 6,93 | (2H, | m) , 7 , 50 | (1H, |
m) , 7 | ,60 - 7,65 (3H, m), 7,91 | (1H, | d, J=0, | 9 Hz) | • | |
IČ (CHC13): 3369, 3270, 2950, | 2873, | 1719, | 1612, | 1498, 1456, | ||
1440, | 1359, 1306, 1269, 1219, | 1146, | 1127/cm. |
[a]D = +18,1° (ch3oh, c=i,oq, 22,0 °c).
150
Č. la-180
CDC13 + CD3OD 300 MHz
1,03 - 1,86 (14H, m) , 2,08 - 2,17 (3H, m), 2,91 (IH, m), 5,06 - 5,10 (2H, m), 6,76 (IH, m), 6,86 - 6,90 (2H, m), 7,48 (1H, m), 7,61 - 7,69 (3H, m) , 7,89 (IH, m).
IČ (CHC13): 3360, 3259, 2954, 2873, 1706, 1612, 1497, 1457, 1360, 1306, 1272, 1230, 1176, 1148, 1126/cm.
[a]D = +20,3° (CH3OH, 0=1,00, 22,0 °C).
Č. la-181
IČ (CHC13): 3380, 3260, 3020, 2946, 2868, 1708, 1466, 1388, 1328, 1149/cm.
[a]D = +32,9° (CHC13, c=l,07, 22,0 °C).
Č. la-182
CDC13 300 MHz
0,94 - 1,90 (14H, m), 2,25 (2H, t, J=7,5 Hz), 2,30 (IH, m),
2,98 | (IH, τη) , 3,70 | (3H, | s), 4,83 (IH, d, J | =6,6 | Hz), 5,13 - |
5,16 | (2H, m) , 6,95 | (IH, | d, J=l,5 Hz), 7,11 | - 7, | 23 (2H, m) , |
7,43 | (IH, d, J=8,l | Hz) , | 7,65 (IH, d, J=8,l | HZ) , | 7,79 - 7,93 |
(4H, | m) , 9,08 (IH, | š) · | |||
IČ (CHC13): 3458, | 3372, | 3020, 3002, 2946, : | 2868, | 1719, 1598, | |
1452, | 1422, 1321, | 1300, | 1157/cm. |
[tt]D = -6,6° (CHC13, c=1,00).
teplota tání 150 až 151 °C.
Č. la-183
CDC13 300 MHz
0,95 - 1,94 (14H, m), 2,26 (IH, m), 2,28 (2H, t, J=7,5 Hz),
3,00 (IH, m) , 5,16 - 5,19 (2H, τη) , 5,32 (IH, d, J=7,2 Hz),
6,93 (IH, d, J=l,2 Hz), 7,13 (IH, m), 7,22 (IH, dd, J=7,8, ···· ·· • ·
- 151 -
6,6 Hz), 7,42 (1H, d, J=7,8 Hz), 7,63 (1H, d, j=7,8 Hz), 7,76 (2H, d, J=8,4 Hz), 7,90 (2H, d, J=8,4 Hz), 8,95 (1H, š).
IČ (CHC13): 3458, 3374, 3260, 3020, 3002, 2948, 2868, 1708, 1598, 1452, 1422, 1301, 1156/cm.
[a]D = +17,9° (CHC13, c=l,01, 22,0 °C).
Č. la-184
CDC13 200 MHz
0,92 - 2,00 (14H, m), 2,20 (1H, m), 2,34 (2H, t, J=6,8 Hz), 3,05 (1Ή, m), 5,20 - 5,36 (3H, m) , 7,39 - 7,44 (2H, m) , 7,61 - 7,66 (1H, m), 7,80 - 7,84 (1H, m), 8,05 (2H, d, J=8,6 Hz), 8,40 (2H, d, J=8,6 Hz).
IČ (CHC13): 3384, 3271, 3019, 2958, 1709, 1615, 1599, 1551, 1453, 1405, 1344, 1326, 1243, 1163/cm.
[cd D * +18,5° (CHC13, C=l,00, 21,0 °C) .
Č. la-185
CDC13 300 MHz
0,89 - 2,20 (15H, m)
2,26 (2H, dt, J=2,l a 7,2 Hz), 2,99
5,08 (1H, d,
J=6,3 Hz),
5,09
5,24 (2H, m), 6,90 (1H, d, J=l,2 Hz), 7,32 - 7,48 (4H, m) , 7,64 - 7,72 (3H, m),
8,20 (1H, d, J=l,2 Hz), 9,00 (1H, s).
IČ (CHC13): 3464, 3375, 3275,
1449, 1356, 1322, 1219, 1147,
3022, 2956, 1707, 1605, 1490,
1131/cm.
[a]D = +21,6° (CHC13, c=l,01, 23,0 °C).
Č. la-186
CDC13 300 MHz
1.36 - 2,24 (14H, m), 2,31 (2H, t, J=7,4 Hz), 2,49 (1H, šs),
3.37 (1H, m) , 3,67 (3H, s), 5, 38 - 5,50 (2H, m), 7,40 - 7,68 (9H, m).
IČ (CHC13): 3375, 1727, 1602, 1435, 1362, 1221, 1207, 1168, 1045/cm.
Č. la-187
CDC13 300 MHz ···· ·♦ • · • · ·
- 152
1,10 - 2,25 (14H, m), 2,36 (2H, t, J=7,2Hz), 2,47 (ÍH, m),
3,37 (1H, m), 5,35 - 5,54 (2H, m), 5,62 (1H, d, J=7,2 Hz), 7,39 - 7,70 (9H, m).
IČ (CHC13): 3674, 3496, 3376, 3234, 3012, 2952, 2880, 2650, 1725 (sh) , 1709, 1602, 1485, 1420, 1360, 1167/cm.
[a]D = +32° (CHC13, c=l,69).
Č. la-188
CDC13 200 MHz
0,86 - 1,92 (14H, m), 2,22 m) , 3,67 (3H, s), 3,93 (3H,
- 5,20 (2H, m), 7,02 7,39 (1H, d, J=7,8 Hz), IČ (CHC13): 3385, 3286, 1617, 1598, 1567, 1507, [a]D = -29,4°
2,36
4,81 (1H, (2H, m) ,
7,89
3019,
1269,
25,0 °C).
(3H, m) ,
s) ,
7,05
7,79
3029,
1311, (CHC13, c=l,01,
7,31 (IH, d, J=8,6 Hz) (3H, m) .
3015, 2954, 2877, 1718, 1153/cm.
Č. la-189 [a}D = -7,7° (CHC13, c=l,00, 24,0 °C)
Č. la-190 [a]D = -17,3° (CHC13, c=l,00, 24,0 °C).
Č. la-191
CDC13 300 MHz
0,95 - 2,20 (14H, m), 2,30 (1H, m) , 2,36 (2H, d, J=6,9 Hz),
3,21 (1H, m), 4,25 (2H, s), 5,07 (1H, d, J=7,8 Hz), 5,35 5,48 (2H, m) , 7,25 (1H, dd, J=l,8 a 8,1 Hz), 7,32 - 7,35 (2H, m) , 7,59 (1H, d, J=8,l Hz), 7,94 (1H, s), 8,14 (1H, d, J=2,7 Hz), 8,23 (1H, dd, J=2,7 a 8,7 Hz).
IČ (CHC13): 3386, 3026, 3015, 2957, 2877, 2633, 1702, 1617, 1573, 1530, 1348, 1123/cm.
[a]D = -6,1° (ČHC13, c=l,01, 25,0 °C).
Č. la-192
CDC13 300 MHz ···· ·
- 153
0,92 - 2,20 (14H, m) , 2,13 (3H, τη) , 3,23 (1H, m) , 3,64 (3H, s) , 3,94 (3H, s), 4,22 (2H, s), 4,36 (1Ή, d, J=7,8 Hz), 5,37 - 5,42 (2H, m) , 7,16 - 7,42 (6H, m), 7,53 (1H, d, J=8,4 Hz),
7,94 (1H, s) .
IČ (CHC13): 3389, 3022, 3013, 2953, 2877, 1716, 1616, 1560, 1485, 1340, 1326, 1124/cm.
[a]D = -15,2° (CHC13, c=1,01, 25,0 °C).
Č. la-193
CDC1- | ( 300 MHz | ||||
0,92 | - 2,20 | (14H, m), 2,25 | (1H, m), 2,35 | (2H, t, J=7,2 Hz), | |
3,17 | (1H, | m) | , 4,22 (2H, s) | , 4,91 (1H, d, | J=7,5 Hz), 5,37 - |
5,42 | (2H, | m) | , 7,13 - 7,43 | (6H, m), 7,60 | (1H, d, J=8,lHz), |
8,05 | (1H, | s) |
IČ (CHC13): 3511, 3387, 3029, 3020, 3011, 2957, 2877, 2651, 1698, 1614, 1560, 1505, 1320, 1280, 1252, 1126/cm.
[a]D = -0,9° (CHC13, c=l,00, 25,0 °C).
Č. lb-1
CDC13 300 MHz
0,98 - 1,56 (15H, m) , 1,85 - 1,90 (5H, m), 2,23 (1H, m), 3,05 (1H, m), 3,66 (3H, s), 4,77 (1H, d, J=6,0 Hz), 5,08 - 5,28 (2H, m) , 7,46 (3H, m) , 7,38 - 7,54 (2H, d, J=7,5 Hz), 7,72 (2H, d, J=8,4 Hz), 7,93 (2H, d, J=8,4 Hz).
IČ (CHC13): 3384, 3028, 2952, 2876, 1719, 1595, 1391, 1322,
1155/cm.
íof]436 = +</θ— +6/θ (CHC13, c=l,00, 23,0 °C) .
teplota tání 96 až 98 °C.
Č. lb-2
CDC13 300 MHz
0,98 - 1,52 (15H, m), 1,85 - 1,90 (5H, m), 2,17 (1H, m), 3,00 (1H, m), 3,67 (3H, s), 4,05 (2H, s), 4,83 (1H, d, J=6,0 Hz), 5,05 - 5,23 (2H, m), 7,14 (2H, d, J=7,2 Hz), 7,17 - 7,32 (5H, m) , 7,78 (2H, d, J=8,4 Hz).
IČ (CHC13): 3384, 3026, 2952, 2874, 1719, 1595, 1453, 1407,
154
1320, 1180/cm.
[tt]D = +2,5° (CHC13, c=1,02, 24,0 °C).
Č. lb-3
CDC13 300 MHz
0,96 - 2,05 (20H, m), 2,07 (1H, m), 3,07 (1H, m), 4,04 (2H,
s), 5,21 - 5,35 (2H, m), 5,55 (1H, d, J=6,9 Hz), 7,14 (2H, d, J=6,6 Hz), 7,20 - 7,32 (5H, m), 7,78 (2H, d, J=8,l Hz).
IČ (CHC13): 3250, 3022, 2950, 1699, 1596, 1495, 1453, 1405, 1318, 1153/cm.
[a]D = +17,1° (CHC13, c=1,O1, 25,0 °C).
teplota tání 129 až 131 °C.
Č. lb-4
CDC13 200 MHz
0,90 - 2,10 (15H, m), 1,19 (3H, s), 1,20 (3H, s), 3,11 (1H,
m), 5,24 - 5,32 (2H, m), 5,70 (1H, d, J=6,6 Hz), 7,38 - 7,68 (4H, m), 7,96 - 8,04 (2H, m), 8,53 (1H, d, J=l,4 Hz).
IČ (CHC13): 3384, 3246, 2958, 1701, 1632, 1595, 1468, 1445, 1322, 1216, 1202, 1190, 1155, 1122/cm.
[d]D = +10,8° (CHC13, C=0,51, 23,0 °C).
Č. lb-5
1,02 - 2,10 (15H, m), 1,16 (6H, S), 3,02 (1H, m), 4,09 (3H,
s), 5,23 - 5,28 (2H, m), 5,76 1H, d, J=7,2 Hz), 7,36 - 7,63 (4H, m), 7,97 (1H, d, J=7,8 Hz), 8,16 (1H, s) .
IČ (CHC13): 3369, 2959, 1702, 1635, 1585, 1468, 1454, 1441, 1415, 1318, 1222, 1189, 1170, 1154/cm.
[a]D = +9,9° (CHC13, c=1,00, 23,0 °C).
Č. 1C-1
CDC13 300 MHz
1,10 - 2,02 (14H, m), 2,27 (2H, t, J=7,5 Hz), 2,50 (1H, m),
2,89 (3H, S), 3,31 (1H, m), 3,64 (3H, S), 5,16 - 5,30 (2H,
m) , 7,34 - 7,42 (3H, m) , 7,50 - 7,59 (2H, m), 7,62 - 7,68 (2H, m), 7,76 - 7,82 (2H, m).
···· ··
2212, 1727, 1596,
1495, 1437,
- 155 IČ (CHC13): 3020, 2946, 2868, 1156, 1135, 1084/cm.
[a]D = -16,1° (CHC13, c=1,05 teplota táni 100 až 102 °C.
1339,
25,0 °C).
C. lc-2
CDC13 300 MHz
1,10 - 2,05 (14H, m), 2,23 (2H, t, J=7,5 Hz), 2,91 (3H, s), 3,35 (ÍH, m) , 3,62 (3H, s), m), 7,50 - 7,60 (3H, m), 7,90 - 8,08 (6H, IČ (CHC13): 3016, 2946, 2868, 1728, 1437, 1086/cm.
(a]D = -32,5° (CHC13, c=l,00, 25,0
2,53 (ÍH, m), 5,02 - 5,30 (2H, m) .
1398, 1340, 1160,
C. 1C-3
- 2,05 (14H, m), 2,13 {2H, t, (3H, s), 3,27 (ÍH, m) , 4,90 m), 7,53 - 7,61 (2H, m) , 7,71 (2H, m) .
J=7,2 Hz), 2,47 (ÍH, m) ,
5,30 (2H, m) , 7,37 - 7,44
7,81 7
7,77 (2H, m),
CD30D 300 MHz
1,15
2,91 (3H,
7,87
IČ (KBr): 3412, 2999, 2951, 2871, 2217, 1560, 1399, 1159, 1137, 1103, 1084.
[a]D = -8,6° (CH3OH,
C=l,03, 23,0
1243,
Č. ld-1
CDC13 300 MHz
1,00 - 2,16 (15H, m),
3,33 (3H, s), 5,23 9,02
3268,
1089/cm.
c=0,53, 22,0
- 8,10 (6H, IČ (CHC13): 1337, 1162,
m) ,
3382,
1120, +40,0° (CHC13,
2,36 (2H, t,
5,43 (3H, m) , (ÍH, ŠS) .
3028, 2954,
J=7,2 Hz),
7,51
3,17
7,59 (3H, (ÍH, m) ,
m), 7,91 [«] D
2874,
1715, 1442,. 1400,
Č. ld-2
CDC13 300 MHz
1,03 - 2,30 (17H, m) , 3,03 (ÍH, m),
4,03 (2H, s) , 5,26 (2H, • · • ·
156
m), 5,84 (1H, š), 5,25 - 5,29 (1H, d, J=6,6 Hz), 6,03 (1H,
Š), 7,14 (2H, d, J=8,l Hz), 7,26 - 7,31 (5H, m) , 7,80 (2H, d, J=8,1 Hz).
IČ (CHC13): 3376, 3002, 2946, 1669, 1595, 1492, 1454, 1406, 1318, 1154/cm.
[cdD = +4,3° (CHC13, C=l,00, 23,0 °C) .
Č. ld-3
CDC13 300 MHz
0,96 - 2, | 17 (17H, m), 2,33 (2H, t, J=6,9 Hz), 3,01 | (1H | , m) , | |||
4,04 (2H, | s) | , 5, 10 (1H, | d, J=6,6 Hz), 5,z | ’1 - 5,26 | (2H, | m) , |
7,14 (2H, | d, | J=8,7 Hz), | 7,16 - 7,32 (5H, | m) , 7,78 | (2H, | d, |
J=8,4 Hz) | ||||||
ič (chci3 | ) : | 3260, 3020, | 2946, 1711, 1596, | 1492, 1457, | 1407, |
1318, 1154/cm.
[ff]D = +9,3° (CHC13, C=l,09, 25,0 °C).
Č. ld-4
CDC13 300 MHz
0,95 - 2,14 (15H, m), 2,34 (2H, t, J=7,2 Hz), 3,09 (1H, m),
3,30 | (3H, | s) , | 4, | 04 | (2H, | S) | , 5,19 | (1H, d, | J=7,2 Hz), 5,22 - |
5,39 | (2H, | m) , | 7, | 10 | - 7, | 35 | (7H, m) | , 7,81 | (2H, d, J=8,1 Hz), |
9,10 | (1H, | X X ss) |
IČ (CHC13): 3382, 3260, 3028, 2952, 2874, 2670, 1713, 1595, 1492, 1450, 1405, 1338, 1160, 1120, 1092/cm.
[a]D = +22,2° (CHC13, c=l,07, 22,0 °C).
Č. ld-5
CDC13 300 MHz
1,00 - 2,10 (14H, m), 2,30 - 2,39 (3H, m), 3,15 (1H, m), 3,35 (3H, S), 5,18 - 5,40 (3H, m), 7,41 (1H, dt, J-0,9 a 7,8 Hz), 7,50 - 7,69 (3H, m), 7,88 - 8,15 (2H, m), 8,60 (1H, d, J=l,5 Hz) , 9,06 (ÍH, S) .
IČ (CHC13): 3382, 3268, 3028, 2954, 2874, 1714, 1442, 1402, 1338, 1188, 1155, 1121, 1072.
[cdD = +15,3° (CHC13, C=l,00, 22,0 °C) .
157
Č. le-1
CDC13 300 MHz
1,19 - 2,45 | (19H, | m), 2,58 (1H, m), 5,63 | (1H, d, | J=3, ( | ) Hz) , | ||
7,42 - 7,65 | (4H, | m) , 7, | 94-8, | 03 (2H, m), | 8,49 - | 8,50 | (1H, |
m) . | |||||||
IČ (CHC13): | 32 93, | 3024, | 1710, | 1595, 1584, | 1467, | 1445, | 1410, |
1324, 1222, | 1213, | 1206, | 1190, | 1160/cm. |
°C) .
23,0 [a]D = -41,1° (CHC13, c=1,01,
Č. ie-2
CDC13 300 MHz
1,10 - 2,25 (19H, m), 2,94 (1H, m) , d, J=7,2 Hz), 7,39 (1H,
J=7,5 Hz), 8,13 (1H, s)
IČ (CHC13): 3367, 3025,
1454, 1440, 1415, 1342,
m) , 7,50
4,12
7,62 (3H, m), (3H, s), 5,53 (1H,
7,96 (1H, d,
2955,
1317, [a]D = +1,2° (CHC13, c=1,OO,
1634, 1600, 1584, 1468,
1189, 1157/cm.
25,0 °C).
1711,
1222,
C. lf-1
CDC13 300 MHz
1,08 - 2,47 (19H, m), 2 | ,56 (1H, m), | 3,52 | (2H, t, | J=6,6 Hz), | |
5,59 {1H, d, J=2,4 Hz), | 7,40 | - 7,66 | (4H, | m), 7,95 - 8,04 (2H, | |
m) , 8,50 (1H, d, J=l,8 | Hz) . | ||||
IČ (CHC13): 3624, 3383, | 3295, | 2950, | 2877, | 1705, | 1595, 1584, |
1468, 1445, 1405, 1347, | 1337, | 1324, | 1224, | 1190, | 1160/cm. |
[a]D = -54,1° (CHC13, c | =1,01, | 23,0 ° | C) . | ||
Č. lf-2 | |||||
CDC13 300 MHz | |||||
1,08 - 2,24 (19H, m) , 2,94 (1H, m), | 3,53 | (2H, t, | J-6,3 Hz), | ||
4,13 (3H, s), 5,47 (1H, | d, J= | 6,6 Hz) | , 7,36 - 7,63 (4H, m), | ||
7,96 (1H, d, J=6,3 Hz), | 8,14 | (1H, s) | . | ||
IČ (CHC13): 3625, 3368, | 3025, | 3013, | 2949, | 2877, | 1710, 1634, |
1600, 1584, 1468, 1454, | 1440, | 1415, | 1342, | 1317, | 1322, 1220, |
1189, 1157/cm.
• ·
158 [α] D = -5,6° (CHC13, c=1,00, 25,0 °C) .
č. ig-i
CDC13 200 MHz
1,17 - 2,34 (15H, | m) , 3, | 22 (1H, m) , | 5,10 - 5,16 | (2H, | m), 5,45 | |
(1H, d, J-7,0 Hz) | , 7,35 | - 7,6< | 5 (4H, | m) , 7,95 - | 8,01 | (2H, m) , |
8,51 (1H, d, J=2, | 0 Hz) . | |||||
IČ (CHC13): 3383, | 3275, | 2959, | 1707, | 1595, 1584, | 1468 | , 1445, |
1425, 1319, 1269, | 1248, | 1190, | 1149, | 1123/cm. | ||
= +64,3° (CHC13, C= | =1,01, | 23,0 | °C) . |
Č. lg-2
CDC13 300 MHz
1,10 - 2,15 | (13H, | m) , 2,36 (2H | ., t, J=7,2 Hz) | , 3 | ,21 | (1H, m) |
4,09 (3H, s) | , 5,10 - 5,22 (2H, | m), 5,43 (1H, | d, | J= | 7,8 Hz), | |
7,36 - 7,62 | (4H, | m), 7,96 (1H, | d, J=7,8Hz), | 8,12 | (1H, s) . | |
IČ (CHC13): | 3366, | 2959, 1708, | 1635, 1600, 1585, | 1467, 1454 | ||
1440, 1415, | 1345, | 1318, 1233, | 1189, 1152/cm. | |||
[a]D = +103, | 1° (CHC13, c=1,01, | 23,0 °C) . |
Č. lh-1
CDC13 300 MHz
0,90 - 1,60 (17H, m), 1,83 (1H, m), 2,11 (1H, m) , 2,22 (2H, t, <1=7,2 Hz), 3,07 (1H, m), 5,11 (lfí, d, J=7,2 Hz), 7,38 7,47 (1H, m), 7,50 - 7,60 (1H, m) , 7,60 - 7,72 (2H, m) ,
7,88 - 8,12 (2H, m) , 8,54 (1H, d, J=0,9 Hz).
IČ (CHC13): 3382, 3274, 2926, 1707, 1464, 1442, 1318, 1266, 1188, 1153, 1121, 1105, 1071, 1019/cm.
[a]D = -2,8° (CHC13, c=1,01, 23,0 °C).
Č. li-l [<x] 365 = +50'9° (CHC13, c=1,01, 24,0 °G) .
Č. li-2
CDC13 300 MHz
0,98 - 1,70 (11H, m), 1,80 - 2,00 (5H, m), 2,19 (1H, m), 3,03 • · • ·
159
(1H, m) , 3,64 (2H, t, J=6,6Hz), 4,05 (2H, s), 4,69 (TH, d, J=6,6 Hz), 5,15 (1H, m), 5,25 (1H, m), 7,16 (2H, d, J-7,2 Hz), 7,27 - 7,32 (5H, m), 7,77 (2H, d, J=8,4Hz).
IČ (CHC13): 3376, 3004, 2946, 2316, 1596, 1492, 1453, 1407, 1318, 1154/cm.
[Q!]d = +3,5° (CHC13, 0=1,00, 22,0 °C) .
teplota tání 80,5 až 82,0 °C.
Č. lj-1 [a]436 = -7,5 + 0,5° (CHC13, č=1,05, 22,0 °C).
Č. lj-2 [0ř]D = -9,7 | ± 0,5° | (CHC13, | c-1,06, | 22,0 | °C) . |
Č. lj-3 [a] D = +15,0 teplota tání | + 0»5° 101 až | (chci3, 108 °C. | c=l,06, | 24,5 | °C) . |
Č. lj-4 [ú = -28,0 teplota tání | + 0,6° 159 až | <chci3, 161 °C. | c=l,06, | 24,0 | °C) . |
Č. lj-5 [a]D = -12,5 teplota tání | + 0,5° 99 až | (CHC13, 101 °c. | c=l,04, | 23,0 | °C) . |
Č. lj-6 CDC13 300 MHz 0,90 - 2,03 (14H, m | ), 2,20 | (1H, m) , | 2,30 | (2H, t, J=7,3 Hz), |
3,00 (1H, m), 3,68 (3H, s), 4,76 (1H, d, J=6,8 Hz), 5,13 5,35 (2H, m), 7,01 - 7,08 (4H, m) , 7,19 - 7,26 (1H, m), 7,37 - 7,46 (2H, m), 7,80 - 7,84 (2H, m).
IČ (CHC13): 3382, 3280, 3080, 3016, 2952, 2900, 1727, 1582, 1486, 1432, 1322, 1150/cm.
[tf]D = -31,0° (CHC13, c-1,05, 26,0 °C) .
• · • ·
- 160 Č. lj-7
CDC13 300 MHz
0,91 - 2,09 (14H, m), 2,15 {1H, m) , 2,35 (2H, t, J=7,5 Hz),
3,01 (1H, m), 5,17 (1H, d, J=6,8 Hz), 5,21 - 5,34 (2H, m), 7,01 - 7,08 (4H, m), 7,15 - 7,27 (1H, m), 7,37 - 7,43 (2H, m), 7,80 - 7,85 (2H, m).
IČ (CHC13): 3474, 3386, 3270, 3024, 2958, 2900, 2675, 1711, 1584, 1488, 1420, 1323, 1298, 1150/cm.
[ce]D = -13,4° (CHC13, 0=1,01, 26,0 °C) .
Č. lj-8
CDC13 300 MHz
0,95 - 2,14 (13H, m), 2,30 (2H, t, J=7,5 Hz), 2,36 (1H, m),
2,84 (1H, m), 2,91 (1J=4,8 Hz), 3,66 (3H, s), 5,33 - 5,52 (2H, m), 6,82 - 6,87 (1H, m), 6,93 - 7,00 (2H, m), 7,09 -
7,15 (4H, m) , 7,28 - 7,36 (2H, m), 7,54 - 7,59 (1H, m).
IČ (CHC13): 3350, 3010, 2950, 2880, 1728, 1603, 1582, 1489, 1461, 1438, 1360, 1160/cm.
[cdD = +75,1° (CHC13, 0=1,13, 26,0 °C) .
Č. lj-9
CDC13 300 MHz
0,95 - 2,03 (14H, m), 2,20 (1H, m) , 2,29 (2H, t, J=7,5 Hz),
3,06 (1H, m), 3,68 (3H, s), 4,98 (1H, d, J=7,4 Hz), 5,14 5,34 (2H, m), 7,46 - 7,54 (2H, m), 7,60 - 7,68 (1H, m), 7,75 - 7,80 (2H, m), 7,88 - 7,92 (2H, m), 7,99 - 8,03 (2H, m).
IČ (CHC13): 3384, 3280, 3020, 2960, 2888, 1727, 1662, 1600, 1316, 1273, 1163/cm.
[tt]D = -41,0° (CHC13, 0=1,17, 26,0 °C).
lj-10
CDC13 + CD3OD 300 MHz
0,94 - 2,08 (14H, m) , 2,21 (1H, m), 2,34 (2H, t, J=6,2 Hz),
3,04 (1H, m), 5,21 - 5,35 (2H, m), 5,40 (1H, m), 7,49 - 7,58 (2H, m), 7,64 -7,68 (1H, m), 7, 79 - 8,06 (6H, m).
IČ (CHC13): 3475, 3370, 3250, 3018, 2956, 2976, 2650, 1709,
161
1662, 1595, 1445, 1420, 1395, 1317, 1274, 1163/cm, [a]D = -17,1° (CHC13, c=1,13, 25,0 °C).
Č. lj-11
CDC13 300 MHz
1,06 - 1,98 (14H, m), 2,24 - 2,29 (3H, m), 3,13 (IH, m), 3,66 (3H, s), 5,10 - 5,24 (2H, m) , 5,40 (IH, d, J=6,3 Hz), 7,39 7,49 (3H, m) , 7,59 - 7,64 (3H, m), 7,80 - 7,83 (2H, m), 8,08 - 8,11 (IH, m).
IČ (CHC13): 3302, 3012, 2948, 2905, 1727, 1661, 1593, 1435, 1332, 1312, 1287, 1271, 1165/cm.
[ff]D = +15,6° (CHC13, c=1,03, 26,0 °C).
Č. lj-12
CDC13 300 MHz
1,08 - 1,98 (14H, m), 2,23 (IH, m), 2,33 (2H, t, J=7,5Hz),
3,16 (IH, m) , 5,18 - 5,26 (2H, m) , 5,39 - 5,45 (IH, τη), 7,39
- 7,49 (3H, m) , 7,60 - 7,64 (3H, m) , 7,80 - 7,83 (2H, m), 8,09 - 8,12 (IH, m).
IČ (CHC13): 3325, 3022, 2956, 2872, 2680, 1708, 1662, 1603, 1598, 1425, 1340, 1316, 1288, 1271, 1165/cm.
[a]D = +9,7° (CHC13, c=0,52, 25,0 °C).
Č. lj-13
CDC13 300 MHz
0,95 - 2,00 (14H, m) , 2,20 (IH, m), 2,27 (2H, t, J=6,3 Hz),
3,03 (IH, m), 3,67 (3H, s), 4,99 (IH, d, J=6,6 Hz), 5,12 -
5,31 (2H, m) , 7,47 - 7,55 (2H, | m) , | 7,60 - | 7,69 | (2H, m), 7,76 |
- 7,81 (2H, m), 7,96 - 8,05 (IH, m) | , 8,08 | - 8,14 (IH, m) , | ||
8,27 - 8,28 (IH, m) . | ||||
IČ (CHC13): 3674, 3538, 3376, | 3276, | 3012, | 2948, | 2860, 1726, |
1662, 1595, 1440, 1335, 1317, | 1297, | 1274, | 1166, | 1150/cm. |
[a]D = +10,2° (CHC13, c=1,00, | 25, 0 | °C) . |
Č. lj-14
CDC13 300 MHz • ♦ • · · • ·
- 162
0,93 - 2,08 (14H, m), 2,21 (1H, m), 2,32 (2H, t, J=6,3 Hz),
3,00 (1H, m), 5,20 - 5,36 (2H, m), 5,38 (1H, d, J=6,2 Hz),
7,50 - 7,55 (2H, m), 7,63 - 7,71 (2H, m), 7,77 - 7,81 (2H,
m) , 7,99 - 8,04 (1H, m), 8,10 - 8,18 (1H, m) , 8,32 - 8,36 (1H, m).
IČ (CHC13): 3674, 3480, 3374, 3258, 3012, 2950, 2875, 2650, 1709, 1662, 1598, 1418, 1335, 1317, 1274, 1143/cm.
[cdD = +61,0° (CHC13, c=l,19, 25,0 °C) .
Č. lj-15
CDC13 300 MHz
0,90 - 2,00 (14H, m) , 2,19 (1H, m) , 2,30 (2H, t, J=7,3'Hz),
3,01 (1H, m), 3,67 (3H, s), 4,82 (1H, d, J=6,6 Hz), 5,14 5,34 (2H, m), 7,36 - 7,39 (3H, m) , 7,53 - 7,57 (2H, m), 7,62 - 7,66 (2H, m), 7,83 - 7,88 (2H, m) .
IČ (CHC13): 3376, 3276, 3010, 2948, 2868, 2212, 1727, 1597, 1500, 1437, 1325, 1161/cm.
la]D = -7,2° (CHC13, c=l,00, 26,0 °C).
Č. lj-16
CDC13 300 MHz
0,93 - 2,03 (14H, m), 2,15 (1H, m), 2,36 (2H, t, J=7,5 Hz),
3,05 (1H, m), 5,20 - 5,40 (3H, m), 7,36 - 7,39 (3H, m), 7,55 - 7,66 (4H, m) , 7,84 - 7,88 (2H, m) .
IČ (CHC13): 3470, 3376, 3260, 3012, 2950, 2868, 2675, 2212, 1708, 1596, 1503, 1416, 1396, 1322, 1160.
(a]D = -22,4° (CHC13, c=1,00, 26,0 °C) .
Č. lj-17
CDC13 300 MHz
1,00 | - 1,60 | (9H, | m) , 1,79 - 1,89 | (5H, | m) , | 2,17 (1H, | ŠS), 2, | 23 | |
(2H, | t, J=7, | 2 Hz) | , 3,03 | (1H, m) , | 5,10 | - 5, | 23 (2H, m) | , 5,49 | |
(1H, | d, J=6, | 6 Hz) | , 7,40 | (1H, t, ú | 1=7,4 | Hz) , | 7,53 (1H, | t f J-7 | ,2 |
Hz) , | 7,60 - | 7,68 | (2H, m) | , 7,98 - | 8,03 | (2H, | m) , 8,55 | (1H, d, |
J=l,5 Hz).
IČ (CHC13): 3516, 3384, 3270, 2666, 1708, 1632, 1595, 1584,
163
1467, 1445, 1425, 1374, 1345, 1321, 1269, 1248, 1218/cm.
[o?]D = -7,8° (CHC13, C=l,01, 22,0 °C) .
Č. lj-18
CDC13 300 MHz
0,90 - 2,03 (14H, m) , 2,19 (1H, m), 2,30 (2H, t, J=7,5 Hz),
3,00 (1H, m), 3,67 (3H, s), 4,80 (1H, d, J=6,4 Hz), 5,14 -
5,35 (2H, m) | , 6,99 - 7,04 (2H, m), | 7,16 - | 7,22 (2H, m) | , 7,34 |
- 7,49 (4H, | m) , 7,57 - 7,61 (1H, m) | • | ||
IČ (CHC13): | 3376, 3276, 3012, 2948, | 2875, | 1727, 1583, | 1488, |
1471, 1432, | 1330, 1311, 1150/cm. | |||
[a] D = +54, C | (CHC13, c=0,99, 25,0 | GC) . | ||
Č. lj-19 | ||||
CDC13 300 MHz | ||||
0,91 - 2,09 | (14H, m) , 2,15 (1H, m) , | 2,34 | (2H, t, J=7,5 | Hz) , |
3,01 (1H, m), 5,16 (1H, d, J=6,6 Hz), 5,24 - 5,40 (2H, m), 7,01 - 7,08 (2H, m), 7,15 - 7,25 (2H, m), 7,35 - 7,53 (4H, m) , 7,59 - 7,65 (1H, m) .
IČ (CHC13): 3470, 3376, 3260, 3012, 2950, 2875, 2640, 1708, 1583, 1488, 1471, 1430, 1335, 1305, 1149/cm.
[a]D = -21,0° (CHC13, c=1,30, 25,0 °C) .
Č. lj-20
CDC13 300 MHz
1,17 (1H, m), 1,26 - 1,34 (2H, m), 1,54 - 2,24 (11H, m), 2,31 (2H, t, J=7,4 Hz), 2,48 (1H, šs) , 3,37 (1H, m), 3,67 (3H, s) , 5,35 - 5,50 (2H, m), 7,39 - 7,68 (9H, m).
IČ (CHC13): 3377, 1727, 1601, 1435, 1362, 1168/cm.
Č. lj-21
CDC13 300 MHz
1,10 - 2,25 (14H, m), 2,36 (2H, t, J=7,2 Hz), 2,47 (ÍH, m) ,
2,89 (1H, m), 5,35 - 5,53 (2H, m), 5,63 (1H, d, J=7,2Hz),
7,40 - 7,71 (9H, m).
IČ (CHC13): 3674, 3496, 3374, 3234, 3010, 2952, 2870, 2640,
- 164 • ·· · ··
1730 (Sh), 1710, 1605 | , 1485, | 1425, | 1360, 1167/cm. | |
[0?]D = -43,0° (CHC13, | G=l,01 | , 25,0 | °C) . | |
Č. lj-22 | ||||
CDC13 300 MHz | ||||
0,98 - 1,95 (14H, m), | 2,25 - | 2,31 | (3H, m), 2,95 (1H, | m) , 5,19 |
- 5,30 (2H, m), 5,33 | (1H, d, | J=3,9 | Hz), 6,58 (1H, d, | J-7,5 |
Hz), 6,80 (1H, t, J=7,5 Hz), 6,99 - 7,05 (1H, m), 7,44 - 7,53 (6H, m), 7,60 - 7,73 (9H, m), 7,94 - 7,73 (3H, m), 8,23 8,26 (2H, m), 10,66 (1H, s) .
IČ (CHC13): 3475, 3372, 3260, 3008, 2952, 2868, 2722, 1725,
1710 (Sh), 1663, 1590, 15711525, 1448, 1437, 1345, 1314, 1161, 1112/cm.
[®]D = +12,9° (CHC13, c=0,12, 23,0 °C).
Č. lj-23
CDC13 300 MHz 0,94 - 1,94 (14H, m), (3H, s), 5,09 (1Ή, d, | 2,23 - 2,30 (3H, m), 2,98 (1H, m), 3,68 J=6,2 Hz), 5,15 - 5,28 (2H, m), 7,14 - |
7,22 (1H, τη) , 7,34 - 7,42 (2H, m) , 7,68 - 7,73 (2H, m) , 7,89 - 8,03 (4H, m), 8,51 (1H, s) .
IČ (CHC13): 3372, 3275, 1724, 1673, 1599, 1438, 1320,
1161/cm.
[Oř] D = +17,0° (CHC13, C=1,38, 25,0 °C) .
Č. lj-24
CDC13 + CD30D 300 MHz
0,96 - 2,05 (14H, m), 2,25 - 2,34 (3H, m), 2,92 (1H, m) , 5,16
- 5,34 (2H, m), 7,14 - 7,22 (1H, m), 7,29 - 7,42 (2H, m),
7,70 (2H, d, J=7,6Hz), 7,92 - 8,05 (4H, m).
IČ (CHC13): 3616, 3426, 3375, 3010, 2950, 2828, 2645, 1708, 1672, 1599, 1439, 1323, 1161/cm.
[a]D = +21,0° (ČH30H, c=1,00, 22,0 °C).
Č. lj-25
CDC13 300 MHz • · • ·
- 165
1,03 (1H, m) , 1,18 - 2,01 (13H, m) , 2,20 (1H, šs) , 2,27 (2H, t, J=7,4 Hz), 3,08 (1H, τη) , 3,66 (3H, s) , 5,11 (1H, d, J=6,6 Hz), 5,14 - 5,34 (2H, m) , 7,54 - 7,62 (3H, m), 8,04 - 8,32 (6H, m) .
IČ (CHC13) : 3384, 3278, 1726, 1605, 1484, 1448, 1331, 1161/cm.
Č. lj-26
CDC13 + CD3OD 300 MHz
1,03 - 2,10 (14H, m) , 2,22 (1H, m), 2,31 (2H, t, J=7,5 Hz), 2,98 (1H, m), 5,23 - 5,38 (2H, m), 7,55 - 7,66 (3H, m), 8,05 - 8,08 (2H, m) , 8,14 - 8,18 (2H, m) , 8,28 - 8,31 (2H, m) .
IČ (Nujol): 3260, 2720, 2660, 1711, 1545, 1460, 1317,
1163/cm.
[odD = +15,8° (CH3OH, C«l,01, 22,0 °C) .
Č. lj-27 [a]D = +16,7° (CHC13, c=l,00, 23,0 °C).
Č. lj-28
CDC13 300 MHz
1,01 (1H, m), 1,14 - 1,29 (2H, m), 1,46 - 2,19 (11H, m), 2,33 (2H, t, J=7,2 Hz), 2,41 (1H, šs), 3,18 - 3,21 (5H, m), 3,68 (3H, s) , 3,73 - 3,76 (4H, m), 4,37 (1H, d, J=7,2 Hz), 5,35 5,45 (2H, m).
IČ (CHC13): 3392, 1727, 1435, 1335, 1148/cm.
[cdD = +10,7° (CHC13, c=l,39, 26,0 °C) .
Č. lj-29
CDC13 300 MHz
1,00 (1H, m), 1,20 - 1,29 (2H, mj, 1,48 - 2,25 (12H, m), 2,37 (2H, t, J=7,2 Hz), 3,17 - 3,22 (5H, m), 3,74 - 3,79 (4H, m), 4,79 (1H, d, J=7,8 Hz), 5,34 - 5,54 (2H, m).
IČ (CHC13): 3470, 3390, 3270, 2675, 1709, 1455, 1420, 1315, 1147/cm.
[a]D = +16,8° (CHC13, C=l,42, 26,0 °C).
166
Č. lk-1 [ce]D = -25,4° (CHCly, c=l,08, 23,0 °C) .
Č. lk-2
CDC13 200 MHz
1,07 - 2,28 (14H, m), 2,32 (2H, t, J=7,4 Hz), 2,63 (1H, m),
3,63 (3H, s), 3,93 (1H, m), 5,30 - 5,52 (2H, m), 6,35 (1H, d, J=7,0 Hz), 7,48 - 7,60 (3H, m), 7,88 - 8,02 (6H, m).
IČ (CHC13): 3438, 3002, 2946, 2868, 1727, 1652, 1514, 1485, 1363, 1310, 1245, 1154/cm.
[a]D = -80,4° (CHC13, C=1,O1, 24,0 °C) ,
Č. lk-3
CDC13 200 MHz
1,10 - 2,26 (14H, m), 2,37 (2H, t, J=7,2 Hz), 2,60 (1H, m) ,
3,93 (1H, m), 5,30 - 5,50 (2H, m), 6,33 (1H, d, J=7,5 Hz), 7,48 - 7,58 (3H, m), 7,88 - 7,99 (6H, m).
IČ (CHC13)3446, 3004, 2952, 2874, 1709, 1652, 1515, 1485, 1305, 1153/cm.
[ce]D - -96,4° (CHC13, C=l,05, 23,0 °C) .
Č. lk-4
CDC13 300 MHz
1,05 - 2,17 (14H, m) , 2,38 (2H, t, J=7,2 Hz), 2,52 (1H, m) ,
3,81 (1H, m), 5,33 - 5,50 (2H, m), 6,08 (1H, d, J=7,6 Hz), 7,39 - 7,53 (3H, m), 7,57 - 7,62 (6H, m).
IČ (CHC13): 3420, 3250, 3008, 2948, 2870, 2660, 2208, 1735 (Sh), 1705, 1640, 1500/cm.
[a]D = -21,9 + 0,6° (CHC13, c=l,02, 22,0 °C).
Č. lk-5
CDC13 300 MHz
1,05 - 2,14 (14H, m), 2,38 (2H, t, J=7,2 Hz), 2,51 (1H, m) ,
3,81 (1H, m), 5,34 -5,46 (2H, m) , 6,07 (1H, d, J=7,6 Hz),
7,33 - 7,56 (5Ή, m) .
• φ φ φ
- 167
IČ (CHC13): 3422, 3250, 3010, 2950, 2876, 2664, 2558, 2210,
1735 (Sh), 1645, 1502, 1441, 1410, 1307, 1276/cm.
[a]D = -63,6 +1,9° (CHC13, c=0,56, 22,0 °C).
Č. lk-6
CDC13 300 MHz
1,04 - 2,24 (14H, m), 2,36 (2H, t, J=7,5 Hz), 2,58 (ÍH, m),
3,88 (1H, τη), 5,30 - 5,43 (2H, m) , 6,21 (ÍH, d, J=7,2 Hz),
7,41 - 7,49 (3H, m) , 7,73 - 7,77 (2H, ta) .
IČ (CHC13): 3447, 3011, 2955, 1708, 1653, 1603, 1578, 1515, 1486, 1457, 1312, 1211, 1164/cm.
[cdj-j = -60,3° (CHC13, c=1,00, 23,0 °C) .
Č. lk-7
CDC13 300 MHz
1,04 | - 2,22 (14H, m) , | 2,36 (2H, t, | J=7, | 2) , | 2,57 | (ÍH, m)7 |
(ÍH, | m) , 5,30 - 5,44 | (2H, τη) , 6,17 | (ÍH, | d, | J=8,7 | Hz), 6, |
7,40 (7H, m), 7,73 (2H, d, J=7,5 Hz).
IČ (CHC13): 3449, 3013, 2955, 1739, 1708, 1651, 1609, 1588, 1522, 1487, 1243, 1227, 1169/cm.
[a]D = -60,2° (CHC13, c=0,92, 23,0 °C) .
Č. lk-8
CDC13 300 MHz
1,04 - 2,25 (14H, m), 2,34 (2H, t, | J=7,5 | Hz), 2,56 (1H, m) , | |||
3,87 (1H, m) | , 5,30 - 5,44 (2H, | m) , | 6,19 | (ÍH, d, | J-7,5 Hz), |
6,83 - 6,94 | (6H, m), 7,69 (2H, | d, | J=8,7 | Hz) . | |
IČ (CHC13): | 3599, 3455, 3012, | 2955 | , 1711 | , 1644, | 1604, 1577, |
1524, 1507, | 1492, 1290, 1236, | 1197 | , 1170/cm. | ||
[0!]d = -47,7 | ° (CHC13, C=l,01, | 22,0 | °C) . |
Č. lk-9
CDC13 300 MHz
1,04 - 2,20 (14H, m), 2,31 (3H, s), 2,36 (2H, t, J=7,2 Hz),
2,56 (ÍH, m), 3,86 (ÍH, m), 5,30 - 5,43 (2H, τη) , 6,16 (ÍH, d,
J=7,2 Hz), 7,00 - 7,11 (6H, m) , 7,74 (2H, d, J=8,7 Hz).
• · · ·
IČ (CHC13): 3450, 3010, 2955, 1750, 1709, 1651, 1609, 1596,
1523, 1489, 1370, 1247, 1227, 1183/cm.
[a]D = -54,7° (CHC13, c=l,01, 22,0 °C) .
- 168 Č. lk-10
CDC13 300 MHZ
1,04 - 2,22 (14H, m), 2,35 (2H, t, J=7,2 Hz), 2,56 (1H, m),
3,82 (3H, S), 3,86 (1H, m), 5,30 - 5,43 (2H, m), 6,17 (1H, d, J=6,9 Hz), 6,89 - 7,01 (6H, m), 7,70 (2H, d, J-8,7 Hz).
IČ (CHC13): 3023, 2955, 1742, 1708, 1649, 1613, 1602, 1577, 1522, 1507, 1490, 1227, 1210, 1170/cm.
[tt]D = -58,1° (CHC13, c=1,01, 22,0 °G) .
Č. lm-1
CDC13 300 MHz
1,06 - 2,25 (14H, m) , 2,32 (2H, t, J=7,4 Hz), 2,61 (1H, m),
3,63 (3H, S), 3,91 (1H, m), 5,35 - 5,47 (2H, m), 6,24 (1H, d, J=6,9 Hz), 7,35 - 7,38 (3H, m) , 7,53 - 7,60 (4H, m), 7,75 7,78 {2H, Hl) .
IČ (CHC13): 3438, 3008, 2946, 2875, 2212, 1732, 1650, 1605, 1519, 1496/cm.
[a]D = +76° (GHC13, c=1,39, 24,0 °C).
Č. lm-2
CDC13 300 MHz
1,05 - 2,20 (14H, m), 2,36 (2H, t, J=6,2 Hz), 2,59 (1H, m),
3,89 (1H, m), 5,29 - 5,48 (2H, m), 6,26 (1H, d, J-7,0 Hz),
7,26 - 7,38 (3H, m), 7,52 - 7,60 (4H, m), 7,73 - 7,77 (2H, m) .
IČ (CHC13): 3444, 3012, 2952, 2874, 2664, 2214, 1718(sh), 1708, 1649, 1605, 1520, 1498/cm.
[cdD = +81,4° (CHC13, c=l,01, 23,0 °C) .
Č. lm-3
CDC13 300 MHz
1,06 - 2,23 (14H, m), 2,32 (2H, t, J=7,0 Hz), 2,62 (1H, m) , ···· ·· • ·
- 169 3,63 (3H, s), 3,93 (ÍH, m) , 5,30 - 5,50 (2H, m) , 6,28 (1H, d,
J=7,0 Hz), 7,38 - 7,51 (3H, ra) , 7,58 - 7,67 (4H, m), 7,83 7,88 (2H, m) .
IČ (CHC13): 3438, 3008, 2948, 2875, 1783(w), 1727, 1650,
1608, 1580(w), 1523, 1501, 1428/cm.
[a]D = +59° (CHC13, c=1,49, 25,0 °C).
Č. lm-4
CDC13 300 MHz
1,08 - 2,25 (14H, m), 2,36 (2H, t, J=7,4 Hz), 2,59 (ÍH, m) ,
3.91 (ÍH, ra) , 5,28 - 5,48 (3H, m) , 6,29 (ÍH, d, J=7,4Hz),
7,38 - 7,50 (3H, ra) , 7,61 - 7,67 (4H, m), 7,81 - 7,86 (2H, m) .
IČ (CHC13): 3436, 3010, 2948, 2868, 1727, 1715(sh), 1649, 1615(w), 1524, 1502, 1482, 1372/cm.
[alD - +72° (CHC13, c=0,98, 25,0 °C).
Č. lm-5
CDC13 300 MHz
1,09 - 2,20 (14H, m), 2,32 (2H, t, J=7,2 Hz), 2,63 (ÍH, m) ,
3,63 (3H, s), 3,92 (1H, m), 5,31 - 5,51 (2H, ra), 6,35 (ÍH, d, J=7,0 Hz), 7,51 - 7,60 (3H, m) , 7,92 - 7,97 (6H, ra).
IČ (CHC13): 3436, 3008, 2946, 2875, 1727, 1652, 1608(w),
1515, 1484/cm.
[0ř]D = +82° (CHC13, C=0,99, 25,0 °C) .
Č. lm-6
CDC13 300 MHz
1,09 - 2,23 (14H, ra), 2,37 (2H, t, J-7,2 Hz), 2,60 (ÍH, m),
3.92 (ÍH, m) , 5,30 - 5,49 (2H, m) , 6,32 (ÍH, d, J=7,4 Hz), 7,51 - 7,55 (3H, τη) , 7,85 - 7,98 (6H, m) .
IČ (CHC13): 3436, 3010, 2950, 2875, 2670, 1727, 1715(sh), 1650, 1605(w), 1515, 1484/cm.
[a]D = +84° (CHC13, c=l,54, 25,0 °C).
170
Č. lm-7
CDC13 300 MHz
1,03 - 2,18 (14H, m), 2,32 (2H, t, J=7,4Hz), 2,59 (1H, m),
3,64 (3H, s) , 3,89 (1H, m), 5,29 - 5,49 (2H, m), 6,16 (1H, d, J=7,8 Hz), 6,98 - 7,06 (4H, m), 7,14 - 7,20 (1H, m), 7,34 -
7,41 (2H, m), 7,73 - 7,78 (2H, m).
IČ (CHC13): 3438, 3008, 2946, 2868, 1727, 1648, 1610, 1586, 1519, 1485/cm.
[tf]D = +54° (CHC13, c=l,29, 25,0 °C) .
Č. lm-8
CDC13 300 MHz
1,06 - 2,21 (14H, m), 2,36 (2H, t, J=7,5 Hz), 2,58 (1H, m),
3,88 (1H, m), 5,31 - 5,46 (2H, m), 6,17 (1H, d, J=6,9 Hz),
6,99 - 7,05 (4H, m), 7,15 - 7,21 (1H, m) , 7,36 - 7,41 (2H, m) , 7,72 - 7,75 (2H, m) .
IČ (CHCL3): 3436, 3010, 2948, 2868, 2675, 1730(sh), 1709, 1647, 1608, 1586, 1520, 1485/cm.
[tt]D = +56° (CHC13, C=0,97, 25,0 °C).
Č. lm-9
CDC13 300 MHz
1,05 - 2,18 (14H, m), 2,29 - 2,34 (5H, m), 2,59 (1H, m), 3,64 (3H, s), 3,89 (1H, m), 5,32 - 5,46 (2H, m), 6,16 (1H, d, J=7,5 Hz), 7,00 - 7,11 (6H, m), 7,74 - 7,77 (2H, m).
IČ (CHC13): 3440, 3010, 2946, 2868, 1729, 1649, 1595, 1519, 1488/em.
[a]D = +47° (CHC13, c=0,82, 25,0 °C).
Č. lm-10
CDC13 300 MHz
1,04 - 2,20 (14H, m) , 2,31 - 2,39 (5H, m), 2,57 (1H, m), 3,87 (1H, m), 5,28 - 5,47 (2H, m), 6,17 (1H, d, J-7,0 Hz), 6,99 -
7,12 (6H, m), 7,72 - 7,76 (2H, m).
IČ (CHC13): 3674, 3572, 3438, 3010, 2948, 2868, 2826, 1748, 1710, 1648, 1615, 1595, 1520, 1489/cm.
• ·
- 171 - • · · · · ·φ φφφφ • φ φ · · · φ φ ·φ • φ ··· · · φ φφφφ φ * · · · φ · · φφφ • · ·· Φ Φ Φ Φ Φ ΦΦ ΦΦ [a]D = +51° (CHC13, c=0,91, 25,0 °C).
Č. lm-11
CDC13 300 MHz
1,04 - 2,16 (14H, m) , 2,31 (2H, t, J=7,2 Hz), 2,59 (1H, tti) ,
3,63 (3H, S), 3,89 (1H, m), 5,29 - 5,49 (2H, m), 6,24 (1H, d, J-7,4 Hz), 6,54 (1H, s), 6,83 - 6,93 (6H, m), 7,69 - 7,73 (2H, m).
IČ (CHC13) : 3674, 3588, 3438, 3296, 3010, 2946, 2868, 1725, 1646, 1603, 1520, 1504, 1489/cm.
[a]D = +51° (CHC13, c-0,91, 25,0 °C).
Č. lm-12
- 2,21 (14H, m), 2,33 (1H, m) , 5,28 - 5,48 (1H, m), 6,87 - 6,94 šs) .
(2H (2H, (6H, , t,
m) ,
m) ,
J=8,0 Hz),
6,23 (1H, d,
7,66 - 7,71
2,56 (1H, m),
J=8,0 Hz) (2H, m), 9,63
CDC13 300 MHz
1,04
3,87
6,75 (1H,
IČ (CHC13): 3674, 3582, 3436, 1727, 1710(sh), 1643, 1603, [a]D = +30° (CHC13, C=O,97,
3010, 2950,
3275,
1522, 1504, 2490/cm.
25, 0 °C) .
2868, 2675,
Č. lm-13
CDC13 300 MHz
1,01 - 2,18 (14H, m) , 2,31
3,63 (3H, s), 3,82 (3H, s),
m) , 6,14 (1H, d, J=7,0 Hz), (2H, m) .
IČ (CHC13) : 3442, 3402, 3004, 2946, 2868, 1727, 1648, 1600, 1518, 1499/cm.
[a]D = +42° (CHC13, C=l,82, (2H, t, J=7,4 Hz), 2,58 (1H, tn) ,
3,89 (1H, m), 5,29 - 5,48 (2H,
6,88 - 7,02 (6H, m), 7,70 - 7,74
26, 0 °C) .
Č. lm-14 (2H, t, J=7,2 Hz), 2,55 (1H, m),
5,25 - 5,46 (2H, m) , 6,16 (1H, d,
172
J=7,2Hz), 6,88 - 7,02 (6H, m), 7,68 - 7,73 (2H, m).
IČ (CHC13): 3438, 3012, 2948, 2870, 2650, 1730(sh), 1709,
1647, 1615(sh), 1601, 1519, 1492/cm.
[a]D = +64° (CHC13, c=0,70, 25,0 °C).
Č. lm-15
CDC13 300 MHz
1,05 - 2,20 (1.4H, m), 2,29 - 2,36 (5H, m), 2,62 (1H, m), 3,63 (3H, s) , 3,92 (1H, m), 5,30 - 5,50 (2H, m), 6,25 (1H, d, J=7,2 Hz), 7,16 - 7,21 (2H, m) 7,59 - 7,64 (4H, m) , 7,83 7,87 (2H, m) .
IČ (CHC13): 3446, 3010, 2946, 2868, 1745(sh), 1728, 1650, 1615, 1525, 1507, 1486/cm.
[óf]D - +65° (CHC13, c=l,02, 23,0 °C) .
Č. lm-16
CDC13 300 MHz
1,0 - 2,21 (14H, m), 2,34 - 2,40 (5H, m), 2,59 (1H, m), 3,90 (1H, m), 5,29 - 5,48 (2H, m), 6,29 (1H, d, J=7,0Hz), 7,18 (2H, d, J=8,6 Hz), 7,58 - 7,64 (4H, m) , 7,83 (2H, d, J=8,2
Hz) .
IČ (CHC13): 3438, 3012, 2948, 2870, 2622, 1749, 1710, 1649, 1610, 1526, 1508, 1487/cm.
[Of]D = +66° (CHC13, c=i,21, 24,0 °C) .
Č. lm-17
CDC13 300 MHz
1,06 - 2,19 (14H, m), 2,32 (2H, t, J=7,2 Hz), 2,62 (1H, m),
3,63 | (3H, s), 3,93 (1H, | m) , 5,30 - | 5,50 (2H, m), 6,32 | (1H, d, | |
J=7,6 | Hz), 6,41 (1H, s) | , 6,94 | (2H, | d, .1=9,0 Hz), 7,47 | (2H, d, |
J=9,0 | Hz), 7,58 (2H, d, | J-8,6 | Hz) , | 7,81 (2H, d, J=8,6 | Hz ) . |
IČ (CHC13): 3580, 3434, | 3284, | 3010, | 2946, 2868, 1726, | 1646, | |
1606, | 1528, 1490/cm. | ||||
ía]D | = +62,4° (CHC13, C | =1,01, | 23,0 | °C) . |
······ · · · ·· ·· • · · · · ·· · · c ·
173 ♦ · · · · » · · ···· · i · · · ··· 9 9 9
99 99 999 98 86
Č. lm-18
CDC13 + CD3OD 300 MHz
1,11-2,18 (14H, m), 2,32 (2H, t, J=7,4 Hz), 2,59 (1H, m),
5,49 (2H, m), ), 7,47 d, J=8,2
5, 2725,
6,55 (1H, d, (2H, d, J=8,6 Hz),
Hz) .
1696, 1635, 1601,
1531,
1510/cm.
[a]D = +99,5° (CH3OH, c=l,011, 25,0 °C) .
Č. lm-19
CDC13 300 MHz
1,05 - 2,20 (14H, m), 2,32 (2H, t, J=7,4 Hz), 2,61 (1H, m) ,
3,63 (3H, s), 3,86 (3H, s), 3,94 (1H, m) , 5,30 - 5,50 (2H, m), 6,24 (1H, d, J=7,0 Hz), 6,99 (2H, d, J=8,6 Hz), 7,53 -7,63 (4H, m), 7,82 (2H, d, J=8,6 Hz).
IČ (CHC13): 3440, 3006, 2946, 2875, 1726, 1649, 1606, 1527, 1510, 1489/cm.
[O!]d = +68° (CHC13, c=0,88, 26,0 °C) .
Č. lm-20
CDC13 300 MHz
1,09 - 2,20 (1.4H, m), 2,35 (2H, t, J=7,3 Hz), 2,58 (1H, m),
3,85 (3H, S), 3,89 (1H, m), 5,28 - 5,48 (2H, m) , 6,35 (1H, d, J=7,2 Hz), 6,98 (2H, d, J=8,8 Hz), 7,51 - 7,61 (4H, m) , 7,81 (2H, d, J=8,4 Hz), 8,34 (1H, Šs).
IČ (CHC13): 3446, 3012, 2952, 2881, 2640, 1730(sh), 1707, 1647, 1606, 1527, 1510, 1489/cm.
[alD = +83° (CHC13, 0=1,00, 25,0 °C).
Č. lm-21
CDC13 300 MHz
1,05 - 2,14 (14H, m), 2,37 (2H, t, J=7,2 Hz), 2,51 (1H, m) ,
3,81 (1H, m), 5,34 - 5,46 (2H, m) , 6,11 (1H, d, J=7,5 Hz),
7,33 - 7,48 (3H, m) , 7,53 - 7,55 (2H, m) .
IČ (CHC13): 3420, 3250, 3008, 2948, 2870, 2660, 2210, 1735 ·♦··♦· · ♦ · «· ·· • · · · · · · 9 · · · • · · ·· · ··«· ·· ··· « · · ···· v «······ ···
174 (sh) , 1705, 1645, 1503, 1441, 1409/cm.
[a]D = +59,2 + 1,0° (CHC13, c-1,023, 22,0 °G) .
Č. lm-22
CDC13 300 MHz
1,05 - 2,17 (14H, m) , 2,37 (2H, t, J=7,2 Hz), 2,52 (1H, m) ,
3,82 (1H, m), 5,32 - 5,47 (2H, m), 6,20 (1H, d, J=7,6 Hz),
7.38 - 7,53 (3H, m), 7,58 - 7,61 (6H, m), 9,11 (1H, šs). IČ (CHC13): 3420, 3250, 3010, 2984, 2870, 2675, 2208, 1730(sh), 1705, 1640, 1500, 1406/cm.
[tt]D = +57,4 (CHC13, C=l,83, 23,0 °C) .
Č. lm-23
CDC13 300 MHz
1,05 - 2,18 (14H, m), 2,31 (2H, t, J=7,5 Hz), 2,60 (1H, m) ,
3,63 (3H, s) , 3,90 (1H, m) , 5,32 - 5,47 (2H, lil), 6,22 (1H, d, J-6,9 Hz), 7,40 - 7,49 (3H, m) , 7,76 - 7,79 (2H, m).
IČ (CHC13): 3438, 3008, 2946, 2868, 1727, 1651, 1603, 1585, 1512, 1484/cm.
[a]D = +52° (CHC13, C=l,49, 25,0 °C).
Č. lm-24
CDC13 300 MHz
1,05 - 2,21 (14H, m), 2,36 (2H, t, J=7,2 Hz), 2,57 (1H, m) ,
3,89 (1H, m), 5,28 - 5,47 (2H, m) , 6,22 (1H, d, J=7,0Hz),
7.39 - 7,55 (3H, m), 7,73 - 7,79 (2H, m) .
IČ (CHC13): 3676, 3572, 3436, 3010, 2948, 2875, 1730(sh), 1709, 1650, 1600, 1580, 1514, 1484/cm.
[a)D = +57° (CHC13, c=0,97, 26,0 °C).
Č. lm-25
CDC13 300 MHz
1,04 - 2,18 (14H, m) , 2,28 - 2,35 (5H, m), 2,59 (1H, m) , 3,62 (3H, s) , 3,88 (ΙΗ, ΤΠ) , 5,29 - 5,49 (2H, m) , 6,20 (1H, d,
J=7,2Hz), 7,15 (2H, d, J=9,0Hz), 7,80 (2H, d, J=8,8Hz).
IČ (CHC13): 3436, 3010, 2946, 2868, 1752, 1653, 1602, 1519,
175
1491/cm.
[a]D = +53° (CHC13, c=1,63, 25,0 °C).
Č. lm-26
CDC13 300 MHz
1,05 - 2,19 (14H, m) , 2,32 - 2,38 (5H, m) , 2,56 (ÍH, m), 3,88 (ÍH, m), 5,29 - 5,47 (2H, m), 6,25 (ÍH, d, J=7,4 Hz), 7,15 (2H, d, J=9,0 Hz), 7,78 (2H, d, J=8,6 Hz).
IČ (CHC13): 3434, 3016, 3006, 2948, 2880, 2622, 1752,
1730(sh), 1710, 1651, 1605, 1520, 1492/cm.
[a]D = +58° (CHC13, c=3,68, 24,0 °C).
Č. lm-27
CDC13 300 MHz
1,05 - 2,16 (14H, m), 2,30 (2H, t, J=7,5 Hz), 2,57 (ÍH, m),
3,62 (3H, s), 3,87 (ÍH, m), 5,27 - 5,47 (2H, m), 6,32 (ÍH, d, J=7,4 Hz), 6,85 (2H, d, J=8,6 Hz), 7,62 (2H, d, J=8,6 Hz), 8,35 (ÍH, s).
IČ (CHC13): 3580, 3450, 3216, 3010, 2946, 2868, 1726, 1640, 1608, 1584, 1528, 1496/cm.
[a]D = +56,2° (CHC13, c=0,713, 23,0 °C) .
Č. lm-28
CDC13 200 MHz
1,10 - 2,25 (14H, m) , 2,32 (2H, t, J=7,2 Hz), 2,55 (ÍH, šs),
3,82 - 3,93 (ÍH, m), 5,27 - 5,47 (2H, m), 6,25 (ÍH, d, J=7,4 Hz), 6,86 (2H, d, J=8,6 Hz), 7,62 (2H, d, J=8,6 Hz).
IČ (CHC13): 3438, 3242, 2675, 1730(sh), 1708, 1639, 1607, 1585/cm.
Č. lm-29
CDC13 300 MHz
1,05 - 2,18 (14Ή, m) , 2,31 (2H, t, J=7,4 Hz), 2,58 (ÍH, m),
3,64 (3H, s), 3,85 (3H, s), 3,89 (ÍH, m), 5,29 - 5,48 (2H,
m), 6,14 (ÍH, d, J=6,6 Hz), 6,92 (2H, d, J=9,0 Hz), 7,74 (2H, d, J=9,0 Hz) .
- 176
IČ (CHC13): 3445, 3008, 2946, 2868, 1727, 1646, 1606, 1578,
1523, 1493/cm.
[a]D = +53° (CHC13, c=2,03, 24,0 °C).
Č. lm-30
CDC13 300 MHz
1,04 - 2,21 (14H, m), 2,36 (2H, t, J=7,3 Hz), 2,56 (1H, m),
3,85 (3H, s), 3,88 (1H, m), 5,27 - 5,46 (2H, m), 6,15 (1H, d, J=7,2 Hz), 6,92 (2H, d, J=8,6 Hz), 7,73 (2H, d, J=8,6 Hz).
IČ (CHC13): 3440, 3010, 2950, 2870, 2645, 1727, 1710(sh), 1646, 1606, 1575, 1524, 1494/cm.
[a]D = +62° (CHC13, C=l,10, 24,0 °C).
Č. lm-31
CDCL3 + CD3OD 300 MHz
1,16 - 2,20 (14H, m) , 2,31 (2H, t, J=7,2 Hz), 2,59 (1H, m),
3,85 (1H, m) , 5,31 - 5,51 (2H, m) , 7,13 - 7,21 (1H, m) , '7,31
- 7,42 (2H, m), 7,68 - 7,93 (6H, m).
IČ (Nujol): 3344, 3175, 2715, 2675, 1699, 1631, 1566/cm.
[cdD = +67° (CH3OH, c=1,01, 24,0 °C) .
Č. lm-32
CDC13 200 MHz
1,09 - 2,23 (14H, m), 2,33 (2H, t, J=7,l Hz), 2,57 (1H, šs),
3,40 - 3,93 (9H, m), 4,41 (1H, šs), 5,29 - 5,48 (2H, m), 6,44 (1H, d, J=7,4 Hz), 7,43 (2H, d, J=7,4 Hz), 7,43 (2H, d, J=8,2 Hz), 7,80 (2H, d, J=7,8 Hz).
IČ (CHC13): 3434, 3354, 1726, 1720(sh), 1660(sh), 1626/cm.
Č. lm-33
CDČ13 200 MHz
1,14 | - 2,25 | (14Ή, | m) , 2,37 (2H, t, J=7 | 3 Hz), 2 | 1,64 | (1H, Šs), |
3,93 | - 4,01 | (1H, | m), 5,30 - 5,51 (2H, m | ) , , 4Ί | (1Ή, | d, J=7,4 |
Hz) , | 7,63 - | 7,74 | (2H, m), 7,79 (2H, s), | 7,89 - | 7,93 | (TH, m) , |
8,00 | (1Ή, dd, J=2 | ,3, 1,0 Hz), 8,30 (1H, | ď, J=l, | 0 Hz), 8,65 - | ||
8,73 | (2H, m) |
177
IČ (CHC13): 3450, 2675, 1728, 1707, 1649, 1528, 1509/cm.
[a]D = +82,8 ± 1,2° (CHC13, C=l,01, 23,0 °C).
Č. 2a-l [a]D = +69,0° (MeOH, c=l,01, 25,0 °C).
Č. 2a-2
CDC13 300 MHz
0,99 (1H, d, J-10,2 Hz), 1,15 a 1,24 (každý 3H, každý s) ,
1,50 - 2,50 (14H, m), 4,30 (1H, m), 5,35 - 5,52 (2H, m) , 6,32 (1H, d, J--8,7Hz), 7,36 - 7,49 (3H, m), 7,58 - 7,62 (2H, m), 7,66 a 7,80 (každý 2H, každý d, J=8,7 Hz).
IČ (CHC13): 3116, 3014, 2925, 2870, 2663, 1708, 1651, 1610, 1524, 1504, 1484, 1472/cm.
(a]D = +64,1° (MeOH, c=l,02, 25,0 °C).
Č. 2a~3 [aÍD = +76,6° (MeOH, c=l,18, 26,0 °C).
Č. 2a-4
CDC13 300 MHz
0,99 (1H, d, J=10,2 Hz), 1,15 a 1,25 (každý 3H, každý s),
1,64 - 2,51 (14H, m), 4,31 (1H, m), 5,36 - 5,53 (2H, m), 6,33 (1H, d, J=8,4 Hz), 7,50 - 7,56 (3H, m), 7,85 - 7,98 (6H, m) . IČ (CHC13): 3515, 3452, 3014, 2925, 2870, 1740, 1708, 1654,
1517, 1486, 1470/cm.
[alD = +79,5° (MeOH, c=l,18, 22,0 °C).
Č. 2a-5
CD3OD 300 MHz
0,98 (1H, d, J=9,9 Hz), 1,18 a 1,25 (každý 3H, každý s), 1,56 - 1,71 (3H, m), 1,98 - 2,40 (11H, m), 4,17 (1H, m), 5,41 5,52 (2H, m), 7,52 - 7,61 (3H, m), 7,91 - 8,01 (6H, m).
IČ (KBr): 3416, 3063, 2983, 2921, 2869, 1704, 1643, 1566,
1518, 1488, 1408/cm.
[a]D = +62,0° (MeOH, c=l,00, 25, 0 °C) .
178 • ·
v c. | 2 a-6 | |||
[ce] | D = +64,1° (MeOH, | C=l,01, | 25,0 | °C) . |
Č. | 2a-7 | |||
[ce] | D = +65,3° (MeOH, | C=0,99, | 25,0 | °C) . |
Č. | 2a-8 | |||
[ce] | D = +74,0° (MeOH, | 0=1,01, | 25,0 | °C) . |
c. | 2 a-9 | |||
[a] | D = +71,0° (MeOH, | C=l,10, | 25, 0 | °C) . |
Č. | 2a-10 | |||
[a] | D = +74,7° (MeOH, | 0=1,00, | 25,0 | °C) . |
Č. | 2a-ll | |||
[a] | D = +72,1° (MeOH, | C=l,00, | 25,0 | °C) . |
Č. 2a-12 [a]D = +53,1° (CHC13, 0=1,01, 26,0 °C) . teplota tání 155,0 až 156,0 °C.
Č. 2a-14 =
+ 72,5° (MeOH, c=l,07, 25,0 °C) .
Č. 2a-13
CDC13 300 MHz
Oj 98 (1H, d, J=10,2 Hz), 1,18 a 1,25 (každý 3H, každý s),
1,63 - 2,40 (14H, m) , 4,30 (TH, m) , 5,46 - 5,58 (2H, m) , 6,44 (1H, d, J=8,4 Hz), 7,9 a 7,7 (každý 2H, každý d, J=8,7 Hz),
7,54 (1H, s).
IČ (CHC13): 3689, 3378, 3028, 3014, 2924, 1713, 1652, 1602,
1522, 1496/cm.
[a]D = +78,3° (MeOH, c=0,84, 25,0 °C).
teplota tání 205,0 až 206,0 °G.
179
Č. 2a-15
CDCl-j 300 MHz
0,99 (IH, d, J=9,9Hz), 1,14 a 1,24 (každý 3H, každý s), 1,55 - 2,44 (14H, m), 4,27 (IH, m), 5,30 - 5,50 (2H, m), 6,29 (IH, d, J=9,0 Hz), 7,11 a 7,20 (každý IH, každý d, J=16,2 Hz),
7,29 - 7,55 (5H, m), 7,57 a 7,72 (každý 2H, každý d, J=8,7 Hz) .
IČ (CHC13): 3453, 3083, 3022, 3013, 2925, 2870, 1708, 1650, 1607, 1560, 1522, 1496/cm.
[a]D = +72,3° (MeOH, C=1,00, 27,0 °C).
teplota tání 115,0 až 117,0 °C.
Č. 2a-16
CDC13 300 MHz
0,92 (IH, d, J=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,50 - 2,48 (14H, m), 3,62 (3H, S) , 4,29 (IH, m) , 5,30 - 5,50 (2H, m) , 6,20 (IH, d, J-8,7 Hz), 6,59 a 6,68 (každý IH, každé d, J=12,3 Hz), 7,23 (5H, s), 7,29 a 7,59 (každé 2H, každé d, J=8,1 Hz).
IČ (CHC13): 3453, 3024, 3016, 2924, 2870, 1730, 1651, 1607, 1520, 1495/cm.
[tt]D = +56,8° (MeOH, c=l,04, 24,0 °C).
Č. 2a-17
CDC13 300 MHz
0,97 (IH, d, J=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,50 - 2,38 (14H, m) , 4,26 (IH, m) , 5,30 - 5,50 (2H, m), 6,23 (IH, d, J=8,4 Hz), 6,59 a 6,70 (každý 1H, každý d, J=12,3
Hz), 7,23 (5H, s), 7,30 a 7,57 (každý 2H, každý d, J=8,7 Hz).
IČ (CHC13): 3452, 3081, 3019, 3014, 2925, 2870, 2665, 1708,
1650, 1607, 1521, 1495/cm.
[a] = +61,6° (MeOH, c=l,00, 27 °C) .
···· ·· ·· · ·· ·· • · · · · 9 4 4 4 9 4 • 44 4 4 4 4 4 44
4 444 4 4 4 44 4 4 4
4 4 4 4 4 4 4 4 4
180
Č. 2a-18
CDC13 300 MHz
0,97 (1H, d, j=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,50 - 2,50 (14H, m), 3,61 (3H, s), 4,31 (1H, m), 5,35 - 5,51 (2H, m), 6,33 (1H, d, J=8,4 Hz), 7,48 - 7,64 (4H, m), 7,79 7,83 (2H, m), 7,91 (1H, dt, J=l,5 a 7,8 Hz), 8,01 (1H, dt, J=l,5 a 7,8 Hz), 8,13 (1H, t, J=l,5 Hz).
IČ CHC13): 3450, 3026, 3013, 2925, 2870, 1730, 1659, 1600, 1510/cm.
[tt]D = +56,0° (MeOH, c=l,01, 25,0 °C).
Č. 2a-19
CDC13 300 MHZ
0,95 (1H, d, J=9,9 Hz), 1,14 a 1,21 (každý 3H, každý s), 1,53
- 2,60 (14H, m) , 4,25 (ΤΗ, τη) , 5,35 - 5,64 (2H, m) , 7,21 (1H, d, J=7,8 Hz), 7,49 - 7,68 (4H, m), 7,76 - 7,84 (3H, m), 8,25 (1H, m), 8,43 (1H, m) .
IČ (CHC13): 3382, 3196, 3025, 3015, 2925, 2870, 1725, 1652, 1599, 1577, 1521/čm.
[Of] D = +55,9° (MeOH, c=l,00, 25,0 °C) .
Č 2a-20
CDC13 300 MHz
0,98 (1H, d, J=10,2 Hz), 1,13 a 1,24 (každý 3H, každý s),
1,50 - 2,50 (14H, m), 3,62 (3Ή, s), 4,31 (1H, m), 5,35 - 5,51 (2H, m), 6,24 (1H, d, J=8,4 Hz), 7,40 - 7,52 (3H, m), 7,71 7,76 (2H, m) .
IČ (CHC13): 3453, 3025, 3013, 2925, 2870, 1730, 1753, 1579, 1514, 1486/cm.
[θ'] D = +61,2° (MeOH, c=l,04, 25,0 °C) .
Č. 2a-21
CDC13 300 MHz
0,98 (1H, d, J=10,2 Hz), 1,13 a 1,23 (každý 3H, každý s), 1,52
- 2,50 (14H, m), 4,28 (1H, m), 5,34 - 5,51 (2H, m), 6,27 (1H, d, J=8,7 Hz), 7,41 - 7,53 (3H, m), 7,71 - 7,74 (2H, m).
• ··
- 181 -
IČ (CHCI3): 3452, 3063, 3027, 3014, 2925, 2871, 1708, 1652, 1578, 1515, 1486/cm.
[a]D = +62° (MeOH, c=l,01, 27,0 °C) .
Č. 2a-22
Dg-DMSO 300 MHz
0,86 (1H, d, J=9,9 Hz), 1,10 a 1,16 (každý 3H, každý s), 1,42
- 1,52 (3H, m), 1,85 - 2,46 (11H, m), 3,98 (1H, m) , 5,32 5,43 (2H, m) , 7,41 (3H, m) , 7,88 (2H, d, J=6,6 Hz), 8,19 (ÍH, d, J=6,6 Hz).
IČ (KBr): 3367, 3060, 2984, 2922, 2868, 1634, 1563, 1529, 1487/cm.
[a]D = +47,7° (MeÓH, Č=l,00, 25,0 °C).
Č. 2a-23 [a]D = +62,7° (MeOH, c=l,01, 27,0 °C).
Č. 2a-24
CDC13 300 MHz
0,99 (ÍH, d, J=10,2 Hz), 1,14 a 1,25 (každý 3H, každý s),
1,52 | - 2,50 (14H, | m) , 4,31 (1H, | m) , | 5,36 - 5,52 (2H, | m) , 6,34 |
(ÍH, | d, J=8,4 Hz) | , 7,47 - 7,52 | (2H, | m) , 7,59 - 7,64 | (1H, m) , |
7,78 | -7,83 (6H, | m) . | |||
IČ (CHC13): 3449, | 3027, 3013, 2925, | 2869, 1708, 1656 | , 1599, |
1518, 1493/cm.
[a] | D = +63,1° | (MeOH, | c-1,00, | 25,0 | °C) . |
Č. | 2a-25 | ||||
[a] | D = +35,1° | (MeOH, | c=l,00, | 25,0 | °C) . |
Č. | 2a-2 6 | ||||
[cd | D = +35,5° | (MeOH, | C=l,02, | 25,0 | °C) . |
Č. 2a-27
CDC13 300 MHz
0,97 (ÍH, d, J=10,2 Hz), 1,12 a 1,23 (každý 3H, každý s) ,
182
1,52 - 2,50 (14H, m), 3,63 (3H, s) , 4,29 (1H, m), 5,36 - 5,51 (2H, m) , 6,18 (1H, d, J=8,4 Hz), 7,01 a 7,71 (každý 2H, každý d, J=8,7 Hz), 6,98 - 7,05 (2H, m), 7,16 (1H, t, J=7,5 Hz), 7,34 - 7,41 (2H, m).
IČ (CHC13): 3455, 3024, 3016, 2924, 2870, 1730, 1651, 1588, 1520, 1487/Gm.
[ajD = +56,4° (MeOH, c=l,01, 25,0 °C).
Č. 2a-28
CDC13 300 MHz
0,98 (1H, d, J=10,2 Hz), 1,12 a 1,23 (každý 3H, každý s),
1,52 - 2,50 (14H, m), 4,26 (1H, m) , 5,34 -5,51 (2H, m), 6,20 (1H, d, J=9,0 Hz), 7,01 a 7,70 (každý 2H, každý d, J=9,0
Hz), 6,98 - 7,15 (2H, tn) , 7,17 (1H, t, J=7,5 Hz) , 7,34 - 7,40 (2H, m).
IČ (CHC13): 3454. 3031, 3018, 2925, 2870, 1708, 1650, 1588, 1523, 1487/cm.
[ff]D = +56,2° (MeOH, c=l,00, 25,0 °C).
Č. 2a-29 [tt]D = +53,0° (MeOH, C=l,03, 25,0 °C).
Č. 2a-30
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,10 a 1,23 (každý 3H, každý s),
1,52 - 2,50 (14H, m), 4,25 (1H, m), 5,30 - 5,50 (2H, m) , 6,23 (1H, d, J=8,7 Hz), 6,36 (1H, Š), 7,26 - 7,39 (1GH, m), 7,60 a 7,68 (každý 2H, každý d, J=8,4 Hz).
IČ (CHC13): 3451, 3088, 3064, 3029, 3014, 2925, 2869, 1707, 1652, 1522, 1495/cm.
[a]D = +54,2° (MeOH, C=l,00, 25,0 °C).
Č. 2a-31
CDC13 300 MHz
0,98 (1H, d, J=10,2 Hz), 1,14 a 1,24 (každý 3H, každý s),
1,50 - 2,50 (14H, m) , 3,63 (3H, s), 4,31 (1H, m), 5,30 - 5,50
183 (2H, m) , 6,26 (1H, d, J=8,4 Hz), 6,90 (1H, t, J=7,4 Hz), 7,13 (1H, d, J=8,7 Hz), 7,29 (2H, t, J=8,0 Hz), 7,67 - 7,75 (5H, m), 7,82 (1H, S).
IČ (Nujol): 3380, 3244, 1723, 1638, 1601, 1578, 1535, 1495/cm.
[a]D = +73,6° (MeOH, c=0,50 26,0 °C) .
teplota tání 133,0 až 134,0 °C.
2a-32 [a]D = +56,1° (MeOH, c=l,02, 26,0 °C) .
Č. 2a-33
CDC13 300 MHz
0,95 (1H, d, J=10,2 Hz), 1,10 a 1,21 (každý 3H, každý s),
1,50 - 2,50 (14H, m) , 4,25 (1H, m), 5,13 (2H, š), 5,30 - 5,70 (3H, m) , 6,41 (1H, d, J=8,2 Hz), 6,89 (1H, s), 7,09 (1H, s), 7,17 a 7,72 (každý 2H, každý d, J=8,2 Hz), 7,62 (1H, s).
IČ (CHC13): 3450, 3125, 3031, 3013, 2925, 2870, 2467, 1917, 1708, 1654, 1615, 1575, 1523, 1497/cm.
[tt]D = +55,2° (MeOH, c=l,01, 26,0 °C) .
Č. 2a-34 [a]D = +72,9° (MeOH, c=l,03, 25,0 °C) .
Č. 2a-35
CDC13 300 MHz
0,98 (1H, d, J=1O,2 Hz), 1,13 a 1,24 (každý 3H, každý s),
1,52 - 2,48 (14H, m), 4,28 (1H, m) , 5,35 - 5,51 (2H, m), 6,28 (1H, d, J=8,7 Hz), 7,34 - 7,37 (3H, m), 7,52 - 7,55 (2H, m) , 7,58 a 7,71 (každý 2H, každý d, J=8,7 Hz).
IČ (CHC13): 3515, 3452, 3030, 3012, 2925, 2870, 1739, 1708, '1652, 1607, 1555, 1521, 1497/cm.
[cdD = +74,3° (MeOH, C=l,01, 25,0 °C) .
Č. 2a-36 [a]D = +23,4° (MeOH, c=l,07, 25,0 °C).
184
Č. 2a-37
CDC13 300 MHz
0,83 (1H, d, J=10,5 Hz), 0,95 a 1,18 (každý 3H, každý s) ,
1,44 - 2,46 | (14H, | in) , 3,92 (1H, m) , | 5,34 | - 5,52 | (3H, | TO) , 7,26 |
- 7,54 (9H, | m) , 7 | ,62 (1H, s). | ||||
IČ (CHC13): | 3432, | 3310, 3189, 3023, | 3014, | 2924, | 2870 | , 1704, |
1610, 1594, | 1523, | 1487/cm. |
[Oř]D = +25,3° | (MeOH, | c=l,00, | 26, | 0 | ®C) . |
Č. 2a-38 [cdD = +70,9° | (MeOH, | c=l,02, | 25, | 0 | °C) . |
Č. 2a-3 9 [<y]D = +70,6° | (MeOH, | C=l,01, | 25, | 0 | °C) . |
Č. 2a-40 [a]D = +74,7° | (MeOH, | C=l,00, | 25, | 0 | °C) . |
Č. 2a-41 [Oř]D = +72,1® | (MeOH, | e=l,01, | 24, | 0 | °C) . |
Č. 2a-42 [a]D = +69,2® | (MeOH, | c=l,00, | 25, | 0 | ®C) . |
Č. 2a-43 [a]D = +70,8® | (MeOH, | C=l,00, | 25, | 0 | ®C) . |
Č. 2a-44 [a]n = +60,4° | (MeOH, | C=l,00, | 26, | 0 | °C) . |
Č. 2a-45
CDC13 300 MHz
0,97 (1H, d, | J=9,9 Hz), 1,13 a 1,23 | (každý 3H, každý s), | 1,55 | |||||
- | 2,52 (14H, | m) , 4, | 29 (TH, | m), 5,34 | - 5,54 | (2H, m), 6,33 | (1H, | |
d, | J=9,0 Hz) | , 7,10 | (1H, | t, | J=7,4 Hz) | , 7,34 | (2H, t, J=7,4 | Hz) , |
• · * · ·
185 -
7,52 (2H, m), 7,68 a 7,75 (každý 2H, každý d, J=8,4 Hz), 7,80 (1H, s), 8,10 (1H, s) , 10,09 (1H, s).
IČ (CHC13): 3393, 3195, 3093, 3033, 3013, 2925, 2870, 1698, 1656, 1598, 1537, 1498/cm.
[a]D = +59,4° (MeOH, c=l,01, 24,0 °C).
Č. 2a-46 [a]D = +63,5° (MeOH, c=l,00, 25,0 °C).
Č. 2a-47
CDC13 300 MHz
0,97 (1H, d, J=9,9 Hz), 1,12 a 1,23 (každý 3H, každý s), 1,54
- 2,48 (14H, m), 4,29 (1H, m), 5,35 - 5,52 (2H, m) , 6,32 (1H, d, J=8,7 Hz), 7,26 (1H, m), 7,41 (2H, t, J=7,8 Hz), 7,64 (2H, d, J=7,5 Hz), 7,73 a 7,77 (každý 2H, každý d, J=8,4 Hz), 7,95 (1H, S), 9,20 (1H, S), 10,38 (1H, sj.
IČ (CHC13): 3450, 3339, 3003, 2992, 2925, 2870, 1706, 1653, 1596, 1523, 1495/cm.
[a]D = +63,3° (MeOH, c=l,00, 25,0 °C).
Č. 2a-48 [tt]D = +63,8° (MeOH, c=l,00, 24,0 °C).
Č. 2a-49
CDC13 300 MHz
1,00 (1H, d, J=10,5 Hz), 1,17 a 1,26 (každý 3H, každý s),
1,55 - 2,52 (14H, m), 4,34 (1Ή, m), 5,36 - 5,54 (2H, m), 6,35 (1H, d, J=9,0 Hz), 7,50 - 7,62 (3H, m), 7,90 a 8,33 (každý 2H, každý d, J=8,4 Hz), 8,21 (2H, m).
IČ (CHC13): 3451, 3029, 3022, 3016, 2925, 2870, 1708, 1655,
1542, 1508, 1498, 1471, 1459/cm.
[cdD = +63,5° (MeOH, c=l,02, 25,0 GC) .
teplota tání 135,0 až 137 °C.
Č. 2a-50 [a]D = +68,9° (MeOH, c=l,01, 24,0 °C).
186
Č. 2a-51 d6-DMSO 300 MHz
0,87 (1H, d, J=9,9 Hz), 1,10 a 1,17 (každý 3H, každý s), 1,40 - 1,60 (3H, m), 1,90 - 2,40 (11H, m), 3,98 (1H, m), 5,35 5,46 (2H, m), 7,64 (1H, s), 7,65 a 7,91 (každý 2H, každý d, J=8,7 Hz), 8,06 (1H, d, J=6,0 Hz), 9,32 (1H, šs).
IČ (KBr): 3385, 2962, 1734, 1707, 1632, 1529, 1498/cm.
[tt]D = +68,4° | (MeOH, | 0=1,01, | 24,0 | °C). | ||
v c. | 2a-52 | |||||
[a] | D = +76,2° | (MeOH, | C = l, | 01, | 24,0 | °C) . |
Č. | 2a-53 | |||||
[a] | D = +73,9° | (MeOH, | C = l, | 02, | 24, 0 | °C) - |
Č. | 2a-54 | |||||
[a] | D = +68,1° | (MeOH, | C=1, | 00, | 24,0 | GC) . |
Č. | 2a-55 | |||||
[«] | D = +67,8° | (MeOH, | c=l, | 00, | 24 , 0 | °C) . |
č. | 2a-56 | |||||
[a] | D = +65,4° | (MeOH, | C = l, | 03, | 25,0 | °C) . |
Č. | 2a-57 | |||||
[a] | D = +63,4° | (MeOH, | 0=1, | 01, | 24,0 | °C) . |
č. | 2a-58 | |||||
[a] | D = +66,6° | (MeOH, | C = l, | 01, | 24,0 | °C) . |
č. | 2a-59 | |||||
[a] | D = +65,5° | (MeOH, | 0=1, | 00, | 24,0 | °C) . |
č. | 2a-60 | |||||
[a] | D = +60,9° | (MěOH, | c=l, | 02, | 25,0 | °C) . |
187
···· | ·· | 9 | ·· | 99 | ||||
• | • · | • | 9 | 99 | • 9 | 9 | • | |
• | • | • | • · | 9 | 9 9 | ·· | ||
• | • | • · | 9 | 9 | 9 | • 999 | 9 | • |
• · | • | • | 9 | 9 | • | 9 | 9 | • |
Č. 2a-61
CDC13 300 MHz
0,97 (1H, d, J=10,0Hz), 1,10 a 1,22 (každý 3H, každý s), 1,50
- 2,50 (14H, m), 4,26 (ÍH, m) , 5,30 - 5,54 (2H, m), 6,28 (ÍH, d, J=8,6 Hz), 6,60 a 6,82 (každý ÍH, každý d, J=12,4 Hz),
7,12 (2H, d, J=6,0 Hz), 7,25 a 7,62.(každý 2H, každý d, J=8,6
Hz), 8,47 (2H, d, j-6,0 Hz).
IČ (CHCI3): 3452, 3027, 3019, 3013, 2925, 2870, 2480, 1708, 1651, 1606, 1520, 1494/cm.
[a]D = +61,6° (MeOH, c=l,01, 25,0 °C).
Č. 2a-62 [a]D = +72° (MeOH, c=0,93, 25,0 °C) .
Č. 2a-63
CDC13 300 MHz
0,99 (ÍH, d, J=10,2 Hz), 1,14 a 1,24 (každý 3H, každý s),
1,50 - 2,50 (14H, m), 4,29 (ÍH, m), 5,36 - 5,55 (2H, m), 6,35 (1H, d, J=9,l Hz), 7,04 a 7,27 (každý ÍH, každý d, J=16,5 Hz), 7,37 (2H, d, J=6,6 Hz), 7,56 a 7,76 (každý 2H, každý d, J-8,4 Hz), 8,57 (2H, d, J=6,6 Hz).
IČ (CHC13); 3452, 3024, 3018, 3014, 2925, 2870, 2470, 1933, 1708, 1652, 1605, 1521, 1496/cm.
[a]D = +69,2° (MeOH, c=l,01, 25,0 ®C).
Č. 2a-64 [O?]D = +56,9° (MeOH, c=l,24, 25,0 °C) .
Č. 2a-65
CDC13 300 MHz
0,98 (ÍH, d, J=10,5 Hz), 1,12 a 1,23 (každý 3H, každý s) ,
1,54 - 2,46 (14H, m) , 4,27 (ÍH, m), 5,23 (2H, s), 5,34 - 5,52 (2H, m), 6,26 (ÍH, d, J=8,4 Hz), 7,32 - 7,45 (5H, m), 7,64 a
7,71 (každý 2H, každý d, J=8,4 Hz), 8,15 (ÍH, s).
IČ (CHC13): 3452, 3088, 3065, 3032, 3013, 2925, 2870, 1708,
188
1653, 1611, 1559, 1522, 1496/cm.
[a]D = +61,0° (MeOH, c=0,91, 25,0 °C) .
Č. 2a-66 [a]D = +76,0° (MeOH, c=l,01, 25,0 °C) .
Č. 2a-67
CDC13 300 MHz
0,98 (ÍH, d, J=10,4 Hz), 1,14 a 1,24 (každý 3H, každý s),
1,54 - 2,46 (14H, m), 4,28 (ÍH, m), 5,32 - 5,53 (2H, m), 6,27 (ÍH, d, J=8,6Hz), 6,92 - 7,31 (každý ÍH, každý d, J=16,4
Hz), 7,02 (ÍH, dd, J=5,8 a 3,6 Hz), 7,12 (ÍH, d, J=3,6 Hz),
7,24 (ÍH, d, J=5,8 Hz), 7,51 a 7,70 (každý 2H, každý d, J=8,4 Hz).
IČ (CHC13): 3453, 3029, 3013, 2925, 2870, 1739, 1650, 1604, 1524, 1515, 1494/cm.
[cdD = +76,2° (MeOH, c=l,00, 24,0 °C).
teplota tání 104,0 až 106,0 °C.
Č. 2a-68 [a]D = +57,7° (MeOH, ¢=1,01, 25,0 °C).
Č- 2a-69
CDC13 300 MHz
0,99 (1H, d, J=10,2 Hz), 1,14 a 1,24 (každý 3H, každý s),
1,54 - 2,48 (14H, m) , 4,28 (ÍH, m), 5,34 - 5,53 (2H, m), 6,29
(ÍH, d, J=9,0 Hz), | 6,54 | - 6,74 | (každý 1H, každý | d, J=12,0 | |
Hz), 7,02 (ÍH, dd, | J=4, | 8 a 3,3 | Hz) , | 6,97 (ÍH, dd, J=3,3 a 1,2 | |
Hz), 7,13 (ÍH, dd, | J=4, | 8 a 1,2 | Hz) , | 7,44 a 7,70 | (každý 2H, |
každý d, J=8,7 Hz) | - | ||||
IČ (CHC13): 3453, | 3025, | 3010, | 2925, | 2870, 1708, | 1650, 1607, |
1559, 1523, 1493/cm.
[cdD = +58,4° (MeOH, c=l,00, 25,0 GC) .
Č. 2a-70
Ia]D = +48,6° (MeOH, c=l,00, 25/0 °C).
189 Č. 23-71
CDC13 300 MHz
0,98 (1H, d, J=10,2 Hz), 1,12 a 1,23 (každý 3H, každý s),
1,52 - 2,46 (14H, m), 2,31 (3H, s), 4,26 (1H, m) , 5,33 - 5,52 (2H, m)., 6,20 (1H, d, J=9,3 Hz), 7,02 - 7,11 (6H, m) , 7,70 (2H, d, J=9,0 Hz).
IČ CHC13): 3460, 3031, 3022, 3011, 2925, 2870, 1750, 1708, 1650, 1608, 1597, 1523, 1490/cm.
[a]D = +48,9° (MeOH, c=l,01, 25,0 °G) .
Č. 2a-72 t«]D = +51,2° (MeOH, c=l,02, 25,0 °C) .
Č. 2a-73
CDC13 300 MHz
0,97 (1H, d, J=9,9 Hz), 1,11 a 1,23 (každý 3H, každý s), 1,54 - 2,48 (14H, m), 4,27 (1H, m), 5,32 - 5,52 (2H, m), 6,24 (1H, d, J=9,0 Hz), 6,83 - 6,94 (6H, m), 7,65 (2H, d, J=9,0 Hz).
IČ (CHC13): 3598, 3451, 3199, 3033, 3012, 2925, 2870, 1708, 1642, 1604, 1524, 1507, 1491/cm.
[a]D = +52,2° (MeOH, c=l,01, 25,0 °C).
Č. 2a-74 [ce]D = +51,5° (MeOH, c=0,92, 25,0 °C) .
Č. 2a-75
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,55 - 2,46 (14H, m), 3,82 (3H, s), 4,25 (1H, m), 5,32 - 5,52 (2H, m), 6,19 (1H, d, J=8,7 Hz), 6,89 - 7,01 (6H, m), 7,65 7,68 (2H, m).
IČ (CHC13): 3450, 3025, 3008, 2925, 2870, 2837, 1741, 1649,
1612, 1521, 1505, 1490/cm.
[a]D = +51,1° (MeOH, c=l,00, 25,0 °C).
190
Č. 2a-76 [a]D = +60,4° (MeOH, c=0,98, 25,0 °C).
Č. 2a-77
CDC13 300 MHz
0,99 (ÍH, d, J=10,5Hz), 1,15 a 1,24 (každý 3H, každý s),
1,54 - 2,48 (14H, m) , 2,34 (3H, s), 4,29 (ÍH, m), 5,32 - 5,54 (2H, m), 6,32 (ÍH, d, J=8,4 Hz), 7,19 a 7,60 (každý 2H, každý d, J=8,4 Hz), 7,63 a 7,79 (každý 2H, každý d, J=8,4 Hz).
IČ (CHC13): 3452, 3027, 3012, 2925, 2870, 1751, 1709, 1651,1611, 1560, 1527, 1509, 1489/cm.
[a]D = +61,2° (MeOH, c=l,00, 25,0 °C).
C. 2 a-78 [α]Ό = +67,4° (MeOH, c=l,01, 25,0 °C).
Č. 2a-79
CDC13 300 MHz
0,99 (ÍH, d, J=10,2 Hz), 1,15 a 1,24 (každý 3H, každý s),
1,54 - 2,54 (14H, τη) , 4,31 (ÍH, m), 5,32 - 5,54 (2H, m) , 6,36 (1H, d, J=8,2 Hz), 6,93 a 7,48 (každý 2H, každý d, J=8,6 Hz), 7,59 a 7,75 (každý 2H, každý d, J=8,4 Hz).
IČ (CHC13): 3593, 3448, 3192, 3030, 3010, 2925, 2870, 1708, 1644, 1608, 1591, 1559, 1530, 1516, 1491/cm.
[a]D = +65,8° (MeOH, c=l,01, 25,0 °C).
Č. 2a-80 [a]D = +66,9° (MeOH, c=l,01, 25,0 °C).
Č. 2a-81
CDC13 300 MHz
0,99 (ÍH, d, J=10,5 Hz), 1,15 a 1,24 (každý 3H, každý s),
1,54 - 2,48 (14H, τη) , 3,86 (3H, s) , 4,29 (ÍH, m) , 5,34 - 5,52 (2H, m), 6,20 (ÍH, d, J=8,7 Hz), 6,99 a 7,55 (každý 2H, každý d, J=9,0 Hz), 7,61 a 7,77 (každý 2H, každý d, J=8,7 Hz).
IČ (CHC13): 3450, 3009, 2925, 2870, 2838, 1740, 1708, 1650, • *
- 191 1608, 1557, 1528, 1512, 1491/cm.
[a]D =+66,2° (MeOH, c=l,01, 25,0 °C).
Č. 2a-82 [a]D = +57,7° (MeOH, c=l,02, 24,0 °C) .
Č. 2a-83
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,12 a 1,23 (každý 3H, každý s),
1,54 - 2,48 (14H, m), 2,33 (3H, s), 4,26 (1H, m), 5,32 - 5,52 (2H, m), 6,25 (1H, d, J=8,7 Hz), 7,16 a 7,75 (každý 2H, každý d, J=8,7 Hz).
IČ (CHC13): 3452, 3030, 3022, 3012, 2925, 2870, 1754, 1709, 1654, 1604, 1585, 1522, 1493/cm.
[a]D = +57,4° (MeOH, c=l,01, 24,0 °C) Č. 2a-84 ía]D = +57,8° (MeOH, c=l,01, 24,0 °C).
Č. 2a-85
CDC13 300 MHz
0,95 (1H, d, J=10,2 Hz), 1,12 a 1,22 (každý 3H, každý s),
1,54 - 2,48 (14H, m) , 4,25 (1H, m), 5,32 - 5,52 (2H, m), 6,28 (1H, d, J=8,7 Hz), 6,87 a 7,57 (každý 2H, každý d, J=9,0 Hz). IČ (CHC13): 3590, 3450, 3166, 3019, 3012, 2925, 2871, 1708, 1637, 1608, 1583, 1531, 1498/cm.
[Of]D = +56,0° (MeOH, c=l,01, 24,0 °C) .
Č. 2a-86 [a)D = +59,3° (MeOH, c=l,01, 22,0 °C).
Č. 2a-87
CDC13 300 MHz
0,98 (1H, d, J=10,0 Hz), 1,13 a 1,23 (každý 3H, každý s),
1,54 - 2,48 (14H, m), 3,85 (3H, s), 4,25 (1H, m), 5,32 - 5,53 (2H, m), 6,19 (1H, d, J=8,8 Hz), 6,93 a 7,69 (každý 2H, každý
- 192 d, J=9,0 Hz).
IČ (CHC13): 3450, 3030, 3017, 3012, 2925, 2870, 2840, 1740, 1708, 1647, 1606, 1575, 1525, 1496/cm.
[a]D = +58,2° (MeOH, c=0,99, 22,0 °C) .
Č. 2a-88 [O!]D = +50,9° (MeOH, c=l,02, 25,0 °C) .
Č. 2a-89
CDC13 300 MHz
0,99 (1H, d, J=10,2Hz), 1,18 a 1,26 (každý 3H, každý s),
1,56 - 2,48 (14H, m) , 4,29 (1H, m), 5,36 - 5,54 (2H, m), 7,03 (1H, d, J=8,7 Hz), 7,21 (1H, s), 7,43 (2H, m) , 7,74 (1H, ddd, J=l,8, 6,9 a 8,7 Hz), 8,22 (1H, dd, J=l,8 a 8,1 Hz).
IČ (CHC13): 3443, 3087, 3023, 3014, 2925, 2870, 1708, 1685, 1658, 1630, 1517, 1466/cm.
[a]D = +57,1° (MeOH, c=l,01, 22,0 °C).
teplota tání 117,0 až 118,0 °C.
Č. 2a-90 [a]D = +54,1° (MeOH, C=l,01, 22,0 °C).
Č. 2a-91
CDC13 300 MHz
0,97 (ÍH, d, J=10,2 Hz), 1,13 a 1,23 (každý 3H, každý s),
1,52 - 2,46 | (14H, m) , 4,24 (1H, m) , | 5,34 - 5,52 | (2H, m), 6,49 | |||
- 6,53 (2H, | m) , 7 | ,11 (1H, dd, | J=0,9 | a 3,6 Hz), ' | 144 | (1H, dd, |
J=0,9 a 1,8 | Hz) . | |||||
IČ (CHC13): | 3437, | 3033, 3022, | 3014, | 2925, 2870, | 1739 | , 1708, |
1655, 1595, | 1520, | 1472/cm. |
[Q!]d = +55,0° (MeOH, C=l,00, 22,0 °C) .
Č. 2a-92 [a]D = +50,3° (MeOH, c=l,00, 22,0 °C).
Č. 2a-93
- 193 CDC13 300 MHz
0,95 (1H, d, J=10,5 Hz), 1,12 a 1,23 (každý 3H, každý s),
1,52 - 2,46 (14H, m), 4,25 (1H, m), 5,34 - 5,52 (2H, m) , 6,12 (1H, d, J=8,7 Hz), 7,07 (1H, dd, J=3,9 a 5,1 Hz), 7,45 - 7,48 (2H, m) .
IČ (CHC13) : 3450, 3023, 3011, 2925, 2870, 1739, 1708, 1645, 1531, 1501, 1471/cm.
ícd D = +49.,10 (MeOH, c=l,02 , 24,0 °C) .
Č. 2a-94 (a]D = +51,5° (MeOH, c=l,00, 24,0 °C) .
Č. 2a-95
CDC13 300 MHz
0,96 (1H, d, J=10,.5 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,52 - 2,46 (14H, m), 4,25 (1H, m), 5,34 - 5,56 (2H, m), 6,14 (1H, d, J=8,7 Hz), 7,34 (2H, d, J=2,0 Hz), 7,85 (1H, t, J=2,0 Hz) .
IČ (CHC13): 3452, 3114, 3030, 3013, 2925, 2870, 1708, 1649, 1535, 1498, 1471/Cín.
[ce]D = +55,5° (MeOH, c=l,00, 25,0 °C).
teplota tání 87,0 až 88,0 °C.
Č. 2a-96
CD3OD 300 MHz
0,94 (1H, d, J=10,2 Hz), 1,13 a 1,22 (každý 3H, každý s),
1,50 - 1,76 (3H, m), 1,94 - 2,39 (11H, m), 4,11 (1H, m) , 5,39
- 5,49 (2H, m), 7,43 - 7,51 (2H, m), 8,05 (1H, m) .
IČ (KBr): 3369, 3084, 2985, 2921, 2868, 1630, 1566, 1538, 1503/cm.
[tt]D = +38,8° (MeOH, c=l,01, 22,0 °C) .
Č-2a-97
CD30D 300 MHz
0,93 (1H, d, J=9,9 Hz), 1,13 a 1,22 (každý 3H, každý s), 1,48
- 1,58 (3H, m), 1,96 - 2,36 (11H, m), 4,10 (1H, m) , 5,35 - 194 -
5,50 (2H, m) , 7,42 - 7,51 (2H, m) , 8,06 (1H, m).
IČ (KBr): 3447, 3087, 2987, 2922, 2868, 1629, 1545, 1501/cm. [a]D = +52,9° (MeOH, c=l,01, 24,0 °C).
Č. 2a-98 [a]D = +53,2° (MeOH, c=l,02, 23,0 °C).
Č. 2a-99
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,12 a 1,22 (každý 3H, každý s),
1,26 - 2,45 (24Ή, m), 4,25 (2H, m), 5,34 - 5,52 (2H, m), 6,18 (1H, d, J=8,7 Hz), 6,91 a 7,66 (každý 2H, každý d, J=9,0 Hz). IČ (CHC13): 3455, 3029, 3019, 2939, 2862, 1738, 1709, 1645,
1605, 1523, 1494/cm. | °C) - | |||
[Cř]D = +51,4° | (MeOH, | C=l,00, | 23,0 | |
Č. 2a-100 [a]D = +49,3° | (MeOH, | c=l,00, | 24,0 | °C) . |
Č. 2a-101 (a]D = +51,3° | (MeOH, | c=l,00, | 24, 0 | °C) . |
Č. 2a-102 [a]D = +48,8° | (MeOH, | C=l,01, | 23,0 | °C) . |
Č. 2a-103
Č. 2a-104 [a]D = +77,0° (MeOH, c=l,02, 23,0 °C).
CDC13 300 MHz
0,94 (1H, d, J=10,2 Hz), 1,12 a 1,22 (každý 3H, každý s) ,
1,52 - 2,46 (14H, m), 2,48 (3H, d, J=0,3 Hz), 4,20 (1H, m) ,
5,32 - 5,54 (2H, m), 6,46 (1H, šs), 7,12 (1H, d, J=9,0 Hz).
IČ (CHC13): 3415, 3144, 3029, 3011, 2926, 2871, 1708, 1671,
1598, 1538, 1456/cm [a]D = +49,6° (MeOH, c=l,01, 23,0 °C).
- 195
Č. 2a-105
CDC13 300 MHz
0,93 (1H, d, J=9,9 Hz), 1,09 a 1,21 (každý 3H, každý s), 1,51 - 2,44 (14H, tn) , 3,90 (6H, s) , 4,20 (1H, m) , 5,38 - 5,50 (2H, m), 5,87 (1H, d, J=9,0 Hz), 6,25 a 7,54 (každý 1H, každý d, J=15,6 HZ), 6,84 (1H, d, J=8,l Hz), 7,03 (1H, d, J=l,8 Hz), 7,09 (1H, dd, J=l,8 a 8,1 Hz).
IČ (CHC13): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.
[a]D = +77,3° (MeOH, | c=l,01, | 23,0 | °C) . |
Č. 2a-106 | |||
[a]D = +67,0° (MeOH, | C=l,00, | 25,0 | °C) . |
Č. 2a-107 | |||
[a]D = +66,6° (MeOH, | c=l,01, | 24,0 | °C) . |
teplota tání 168,0 až | 170,0 | °C. | |
Č. 2a-108 | |||
[a]D = +61,89 (MeOH, | C=l,00, | 22,0 | °C) . |
Č. 2a-109
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,10 a 1,22 (každý 3H, každý s),
1,51 - 2,45 (14H, m) , 4,25 (1H, m) , 5,33 - 5,49 (2H, m), 6,21 (1H, d, J=8,7 Hz), 7,25 a 7,60 (každý 2H, každý d, J=8,7 Hz), 7,33 - 7,41 (5H, s).
IČ (CHC13): 3453, 3062, 3028, 3014, 2925, 2870, 1739, 1708, 1651, 1594, 1557, 1515, 1481/cm.
[a)D ·= +61,0° (MeOH, c=l,01, 22,0 °C) .
Č. 2a-110
CD3OD 300 MHz
0,94 (1H, d, J=9,9 Hz), 1,13 a 1,22 (každý 3H, každý s), 1,54
- 2,37 (14H, m), 4,12 (1H, m), 5,38 - 5,49 (2H, m), 7,25 a
196
7,68 (každý 2H, každý d, J=8,7Hz), 7,41 (5H, s).
IČ (KBr): 3435, 3058, 2986, 2920, 2866, 1635, 1595, 1562, 1521, 1482, 1439, 1411/cm.
[a]D = +47,3° (MeOH, G=l,01, 23,0 GC).
Č. 2a-111 [a]D = +65,6° (MeOH, c=l,01, 24,0 °C).
Č. 2a-112
CDCl^ 300 MHz
0,97 (IH, d, J=10,2 Hz), 1,12 a 1,23 (každý 3H, každý s),
1.51 - 2,46 (14H, m), 4,27 (IH, m), 5,35 - 5,50 (2H, m) , 6,22 (IH, d, J=8,4 Hz), 7,40 a 7,66 (každý 2H, každý d, J=9,0 Hz). IČ (CHC13): 3439, 3028, 3012, 2937, 2871, 1739, 1708, 1661, 1620, 1600, 1513/cm.
[a]D = +65,6° (MeOH, c=l,01, 22,0 °C).
Č. 2a-113 [a]D = +59,6° (MeOH, c=l,OO, 24,0 °C) .
Č. 2a-114
CDC13 300 MHz
0,98 (IH, d, J=10,2 Hz), 1,12 a 1,24 (každý 3H, každý s),
1.52 - 2,46 (14H, m) , 4,29 (IH, m), 5,35 - 5,51 (2H, m) , 6,28 (IH, d, J=8,4 Hz), 7,70 a 7,83 (každý 2H, každý d, J=8,4 Hz). IČ (CHC13): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1798, 1661, 1620, 1600, 1513/cm.
[a]D = +60,6° (MeOH, c=l,01, 22,0 °C) .
Č. 2a-115 [a]D = +59,7° (MeOH, C—0,99, 24,0 °C).
Č. 2a-116
CDC13 300 MHz
0,97 (IH, d, J=10,2 Hz), 1,12 a 1,23 (každý 3H, každý s),
1,52 - 2,46 (14H, m) , 2,39 (3H, s) , 4,27 (IH, m) , 5,33 - 5,51 • · ·
- 197 (2H, m), 6,24 (1H, d, J=9,0Hz), 7,23 a 7,62 (každý 2H, každý d, J=8,4 Hz).
IČ (CHC13): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.
[O!]D = +59,7° (MeOH, c=0,99, 24,0 °C) .
Č. 2a-117 [a]D = +56,7° (MeOH, 0=1,00, 23,0 °C) .
Č. 2a-118
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,53 - 2,44 (14H, m), 4,23 (1H, m), 5,34 - 5,51 (2H, m), 6,02 (2Ή, s), 6,13 (1H, d, J=8,7 Hz), 6,83 (1H, dd, J=l,2 a 7,8 Hz), 7,22 - 7,25 (2H, m) ,
IČ (CHC13): 3453, 3031, 3020, 3012, 2924, 2870, 1740, 1708, 1650, 1619, 1605, 1519, 1504, 1480/cm.
(«]D = +57,2° (MeOH, c=l,02, 23,0 °C).
Č. 2a-119
CDC13 300 MHz
0,96 (1H, d, J=10,5 Hz), 1,07 a 1,23 (každý 3H, každý s),
1,51 - 2,44 (14H, m) , 2,32 (3H, s) , 4,26 (1H, m), 5,37 - 5,52 (2H, m), 6,40 (1H, d, J=9,0Hz), 7,09 (1H, m) , 7,30 (1H, m), 7,46 (1H, τη) , 7,66 (1H, m) .
IČ (CHC13): 3443, 3028, 3012, 2925, 2870, 1766, 1747, 1709, 1657, 1607, 1516, 1479/cm.
[a]D = +53,2° (MeOH, c=0,99, 21,0 OC).'
Č. 2a-120
CDC13 300 MHz
0,98 (1H, d, J=10,2 Hz), 1,14 a 1,24 (každý 3H, každý s),
1,53 - 2,44 (1H, m), 4,30 (1H, m), 5,35 - 5,52 (2H, m), 6,42 (1H, d, J=8,7 Hz), 6,85 (1H, m), 6,99 (1H, dd, J=l,2 a 8,4
Hz), 7,27 (1H, m), 7,39 (1H, m) .
IČ (CHC13): 3463, 3033, 3021, 3014, 2992, 2924, 2870, 1708,
198
1643, 1597, 1523, 1488/cm.
[a]D = +46,3° (MeOH, c=l,01, 21,0 °C) .
Č. 2a-121
CDC13 300 MHz
0,98 (1H, d, J=10,2 Hz), 1,14 a 1,23 (každý 3H, každý s),
1,47 - 2,47 (14H, m), 3,95 (3H, s), 4,31 (1H, m) , 5,32 - 5,50 (2H, m) , 6,98 (1H, dd, J=0,9 a 8,4 Hz), 7,09 (1H, ddd, J=0,9, 7,7 a 8,4 Hz), 7,45 (1H, m) , 8,19 (1H, dd, J=2,1 a 8,1 Hz), 8,32 (1H, d, J=9,0 Hz).
IČ (CHC13): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842, 1736, 1708, 1640, 1600, 1536, 1483, 1470/cm.
[a]D = +38,1° | (MeOH, | c=l,02, 23,0 | °C) . |
Č. 2a-122 | |||
[a] D = +42,3 ° | (MeOH, | c=0,99, 23,0 | °C) . |
Č. 2a-123 [a]D = +38,7° | (MeOH, | c=l,00, 21,0 | °C) . |
Č. 2a-124 | |||
(a)D = +45,0° | (MeOH, | c=l,01, 21,0 | °C) . |
teplota tání | 119,0 až 120,0 °C. | ||
Č. 2a-125 | |||
[ofJD = +49,8° | (MeOH, | C=l,01, 22,0 | °C) . |
Č. 2a-126
CDC13 300 MHz
0,97 (1H, d, J-=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,52 -2,47 (14H, m), 4,26 (1H, m), 5,34 - 5,50 (2H, m), 6,22 (1H, d, J=8,7 Hz), 7,55 - 7,61 (4H, m).
IČ (CHC13): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842,
1736, 1708, 1640, 1600, 1536, 1483, 1470/cm.
[ú]D = +63,0° (MeOH, c=l,01, 23,0 °C).
199
Č. 2a-127
CDC13 300 MHz
0,91 (ÍH, d, J=10,2 Hz), 1,10 a 1,20 (každý 3H, každý s),
1,50 - 2,42 (14H, m) , 4,23 (ÍH, m) , 5,31 - 5,51. (2H, m) , 6,45 (ÍH, d, J=8,4 Hz), 7,01 (ÍH, t, J=7,4 Hz), 7,22 - 7,27 (2H, m), 7,33 - 7,40 (4H, m), 7,53 (2H, d, J=9,0 Hz), 8,30 a 8,48 (každý ÍH, každý s)
IČ (CHC13): 3452, 3028, 3022, 3015, 2925, 2870, 1708, 1654, 1590, 1514, 1478/cm.
[a]D = +59,5° (MeOH, c=l,01, 23,0 °C).
Č. 2a-128 dg-DMSO 300 MHz
0,84 (ÍH, d, J=9,9 HZ), 1,06 a 1,19 (každý 3H, každý s), 1,37 -2,37 (14H, m), 3,79 (ÍH, m), 5,35 - 5,51 (2H, m), 6,08 (1H, d, J=8,7 Hz), 6,85 - 6,90 (ÍH, m), 7,18 - 7,23 (2H, m), 7,35 - 7,38 (2H, m), 8,42 (ÍH, s), 12,00 (ÍH, s).
IČ (Nujol): 3395, 3345, 2925, 2866, 2623, 2506, 1697, 1658, 1638, 1597, 1557/cm.
(alD = +26,0° (MeOH, c=l,01, 23,0 °C).
teplota tání 164,0 až 166,0 °C.
Č. la-129
CDC13 300 MHz
1,01 (ÍH, d, J=10,0 Hz), 1,17 a 1,25 (každý 3H, každý s) ,
1,54 - 2,52 (14H, m), 4,34 (ÍH, m), 5,36 - 5,37 (2H, m), 6,42 (ÍH, d, J=8,6 Hz), 7,51 - 7,60 (2H, m), 7,77 (ÍH, dd, J=l,8 a 8,6 Hz), 7,85 - 7,96 (3H, m), 8,24 (1H, šs).
IČ (CHC13): 3451, 3060, 3028, 3010, 2925, 2870, 1708, 1652, 1629, 1600, 1517, 1502/cm.
[a]D = +68,6° (MeOH, c=l,00, 22,0 °C).
Č. 2a-130
CDC13 300 MHz
1,02 (ÍH, d, J=10,2 Hz), 1,04 a 1,26 (každý 3H, každý s),
1,54 - 2,52 (14H, m), 4,41 (ÍH, m), 5,41 - 5,58 (2H, m), 6,14 ···· ·· ·· · ·· ·· • · · · · ·· ···· ······ · · ·· • 4 ··· · · · ··· · · • 4 4 4 ··· 4··
200 (1H, d, J=9,0 Hz), 7,43 - 7,59 (4H, m), 7,85 - 7,92 (2H, m), 8,27 (1H, dd, J=l,8 a 7,2 Hz).
IČ (CHC13): 3436, 3032, 3010, 2924, 2870, 2664, 1708, 1652, 1512, 1498/cm.
[a]D = +93,9° (MeOH, c=l,00, 22,0 °C).
teplota tání 94,0 až 96,0 °C.
Č. 2a-131 | ||||
[0ř]D = +50,2° | (MeOH, | c=0,95, | 21,0 | °C) . |
Č. 2a-132 [a]D = +10,9° | (MeOH, | c=0,92, | 21, 0 | °C) . |
Č. 2a-133 = +60,4° | (MeOH, | c=l,00, | 21,0 | °C) . |
Č. 2a-134 [a]D = +38,5° | (MeOH, | C=l,01, | 23,0 | °C) . |
Č. 2a-135 [cdD = +52,5° teplota tání | (MeOH, 180,0 až | c=l,01, 182,0 | 23,0 °C. | °C) . |
C. 2a-136 [a]D = +35,3° (MeOH, c=l,02, 23,0 °C) . teplota tání 79,0 až 80,0 °C.
Č. 2a-137
CDC13 300 MHz
0,97 (1H, d, J=10,2Hz), 1,11 a 1,22 (každý 3H, každý s),
1,43 (3H, t, J=6,9 Hz), 1,52 - 2,44 (14H, m), 4,03 (2H, q,
J=6,9Hz), 4,26 (1H, m), 5,33 - 5,50 (2H, m), 6,19 (1H, d,
J=8,7 Hz), 6,88 - 7,00 (6H, m), 7,65 - 7,68 (2H, m).
IČ (CHC13): 3455, 3031, 3024, 3014, 2988, 2925, 2870, 1741,
1708, 1649, 1602, 1521, 1504, 1490/cm.
[<x]D = +52,0° (MeOH, c=l,01, 23,0 °C).
201 Č. 2a-138
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz)', 1,11 a 1,22 (každý 3H, každý s) ,
1,35 (6H, d, J=6,0 Hz), 1,53 - 2,46 (14H, m), 4,25 (1H, m),
4,51 (1H, m), 5,33 - 5,50 (2H, m), 6,12 (1H, d, J=9,0 Hz),
6,87 - 6,99 (6H, m), 7,65 - 7,68 (2H, m).
IČ (GHC13): 3454, 3031, 3014, 2980, 2925, 2870, 1741, 1708, 1649, 1602, 1522, 1490/cm.
[a]D = +50,0° (MeOH, c=l,05, 22,0 °C),
Č. 2a-139
CDC13 300 MHz
1,00 (1H, d, J=10,2 Hz), 1,16 a 1,24 (každý 3H, každý s),
1,59 - 2,52 (14H, m), 4,31 (1H, m), 5,40 - 5,53 (2H, m), 6,36 (1H, d, J=8,7 Hz), 6,70 (1H, d, J=l,5 Hz), 7,12 (1H, m), 7,30 (1H, m), 7,47 (1H, dd, J=0,6 a 8,1 Hz), 7,61 (1H, d, J=8,4 Hz) .
IČ (CHC13): 3449, 3243, 3029, 3022, 3013, 2925, 2871, 1707, 1631, 1542, 1505/cm.
[a]D = +63,4° (MeOH, c=l,00, 23,0 °C).
teplota tání 178,0 až 179,0 °C.
Č. 2a-141
CDC13 300 MHz
Č. 2a-140
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,18 a 1,23 (každý 3H, každý s),
1,57 - 2,50 (14H, m) , 4,35 (1H, m), 5,32 - 5,55 (2H, m), 6,42 (1H, d, J=8,7 Hz), 6,70 (1H, d, J=l,5 Hz), 7,21 - 7,24 (2H,
m), 7,46 (1H, m), 7,76 (1H, m), 7,86 (1H, d, J=3,0 Hz), 10,20 (1H, s).
IČ CHC13): 3465, 3010, 2924, 1739, 1604, 1546, 1504/cm.
[a]D = +39,4° (MeOH, c=l,01, 22,0 °C).
teplota tání 167,0 až 168,0 °C.
202
0,99 (1H, d, J=10,2 Hz), 1,14 a 1,24 (každý 3Ή, každý s),
1,55 - 2,44 (14Ή, m), 3,84 (3H, s), 4,27 (1H, m), 5,34 - 5,52 (2H, m), 6,28 (1H, d, J=9,0 Hz), 6,91 a 7,47 (každý 2H, každý d, J=9,0 Hz), 6,98 a 7,14 (každý 1H, každý d, J=16,5 Hz),
7,54 a 7,70 (každý 2H, káždý d, J=8,7 Hz).
IČ (CHC13): 3453, 3025, 3015, 2925, 2870, 2839, 1740, 1708, 1649, 1602, 1510, 1493, 1470/cm.
[a]D = +73,4° (MeOH, c=l,02, 22,0 °C) .
teplota tání 155,0 až 157,0 °C.
Č. 2a-142
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,52 - 2,45 (14H, m) , 3,79 (3H, s), 4,27 (1H, m), 5,34 - 5,50 (2H, m), 6,24 (1H, d, J=9,0 Hž), 6,49 a 6,62 (každý 1H, každý d, J=12,3 Hz), 6,77 a 7,16 (každý 2H, každý d, J=8,7 Hz),
7,32 a 7,59 (každý 2H, každý d, J=8,lHz).
IČ (CHC13): 3453, 3025, 3014, 2925, 2870, 2839, 1739, 1708,
1649, 1606, 1510, 1494/cm. [a]D = +60,7° (MeOH, c=0,99, | 22,0 | °C) . | |
Č. 2a-143 | |||
[a]D = +57,3 | ° (MeOH, c=l,01, | 23,0 | °C) . |
Č. 2a-144 | |||
ía]D = +12,2 | ° (MeOH, c=l,00, | 23,0 | °C) . |
teplota tání | 114,0 až 116,0 | °C. |
Č. 2a-145
CDC13 300 MHz
0,95 (1H, d, J=10,2 Hz), 1,10 a 1,21 (každý 3H, každý s),
1,52 - 2,44 (14H, m) , 4,25 (1H, m), 5,33 - 5,49 (2H, m), 6,37 (1H, d, J=8,7 Hz), 7,45 - 7,47 (3H, m), 7,62 - 7,66 (2H, m),
7,69 a 7,80 (každý 2H, každý d, J=7,5 Hz).
IČ (CHC13): 3449, 3058, 3027, 3012, 2925, 2870, 1708, 1655,
1513, 1481, 1043/cm.
·* . ·· • · · · ♦ ·· · · · · • · · · · · · · ·· • · · · · · · · ·«·· · Λ Λ _ ····♦·· ···
- 203 - ** ·· ·· ··· ·· ·· ···· ·· [a]D = +61,0° (MeOH, c=l,01, 23,0 °C).
Č. 2a-146
CDC13, 300 MHz
0,95 (1H, d, J=10,5 Hz), 1,09 a 1,21 (každý 3H, každý s),
1,50 - 2,41 (14H, m), 4,25 (1H, m), 5,33 - 5,49 (2H, m), 6,33 (1H, d, J=8,4 Hz), 7,49 - 7,61 (3H, m), 7,91 - 7,92 (2H, m), 7,82 a 7,97 (každý 2H, každý d, J=8,7 Hz).
IČ (CHC13): 3447, 3029, 3023, 3015, 2925, 2870, 1708, 1660, 1514, 1484, 1321, 1161/cm.
[tt]D = +62,0° (MeOH, c=l,00, 22,0 °C).
Č. 2a-147
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,12 a 1,23 (každý 3H, každý s) ,
1,52 - 2,46 (14H, m), 2,51 (3H, s) , 4,26 (1H, m), 5,34 - 5,51 (2H, m), 6,23 (1H, d, J=8,4 Hz), 7,26 a 7,64 (každý 2H, každý d, J—8,4 Hz).
IČ (CHC13): 3453, 3027, 3015, 2925, 2870, 2665, 1708, 1648, 1596, 1516, 1484/cm.
[a]D = +67,7° | (MeOH, | c=0,82, 22,0 °C) . |
Č. 2a-148 | ||
[cdD = +72,5° | (MeOH, | C=l,01, 25,0 °C) . |
Č. 2a-149 | ||
[a]D = +67,8° | (MeOH, | c=0,98, 25,0 °C). |
Č. 2a-150
CDC13 300 MHz
0,94 (1H, d, J-10,2 Hz) , 1,10 a 1,23 (každý 3H, každý s),
1,52 - 2,50 (14H, m) , 4,22 (1H, m), 5,36 - 5,55 (2H, m), 6,48 (1H, d, J=8,4 Hz), 8,35 (1H, s), 8,90 (IH, s).
IČ (CHC13): 3443, 3374, 3091, 3024, 3012, 2925, 2871, 1709,
1652, 1525, 1494/cm.
[a]D = +58,1° (MeOH, c=l,01, 23,0 °C).
• ·· ·· ·· k · · · • · · ·· « k> ··· · · • · · · Φ·· ·φ ·· ···· ·· ♦ · · · · • · · · · • · · · · φ • · · · · · ·· ♦ · ··
204 teplota tání 120,0 až 122,0 °C.
Č. 2a-151 [a]D = +40,6° (MeOH, c=l,01, 23,0 °C) .
Č. 2a-152
CDC13 300 MHz
0,96 (1H, d, J=10,5 Hz), 1,10 a 1,24 (každý 3H, každý s),
1.50 - 2,50 (14H, m), 2,71 (3H, s), 4,26 (1H, m), 5,37 - 5,51 (2H, m), 6,02 (1H, d, J=9,0 Hz), 8,73 (1H, s) .
IČ (CHC13): 3463, 3435, 3087, 3025, 3014, 2925, 2870, 1708, 1649, 1523, 1503/cm.
[a]D = +54,1° (MeOH, c=l,02, 22,0 °C) .
Č. 2a-153
CDC13 300 MHz
0,95 (1H, d, J=9,9 Hz), 1,11 a 1,23 (každý 3H, každý s), 1,50
- 2,50 (14H, m), 2,50 (3H, s) , 4,26 (1H, m), 5,36 - 5,51 (2H, m), 6,01 (TH, d, J=8,4 Hz), 6,88 (1H, d, J=5,1 Hz), 7,26 (1H, d, J=5,1 Hz) .
IČ (CHC13): 3469, 3431, 3025, 3013, 2925, 2871, 2664, 1708, 1639, 1544, 1505/cm.
[a]D = +35,8° (MeOH, C=l,03, 22,0 °C).
Č. 2a-154
CDC13 300 MHz
0,95 (1H, d, J=9,9 Hz), 1,10 a 1,22 (každý 3H, každý s), 1,52
- 2,46 (14H, m), 2,51 (3H, d, J=l,2 Hz), 4,26 (1H, m), 5,34 -
5.50 (2H, m), 6,00 (1H, d, J=8,4 Hz), 6,73 (1H, dd, J-5,1 a 3,6 Hz), 7,29 (1H, d, J=3,6 Hz).
IČ (CHC13): 3450, 3431, 3026, 3011, 2925, 2869, 1739, 1708,
1639, 1547, 1508/cm.
[a]D = +50,5° (MeOH, c=l,01, 22,0 °C) .
Č. 2a-155
CDC13 300 MHz
205
0,99 (1H, d, J=10,2 Hz), 1,19 a 1,25 (každý 3H, každý s),
1.53 - 2,48 (14H, m) , 4,31 (1H, m), 5,36 - 5,51 (2H, m), 6,79 (1H, d, J-9,3 Hz), 7,29 (1H, ni), 7,41 (1H, m) , 7,48 (1H, s) ,
7,51 (1H, m), 7,66 (1H, d, J=8,l Hz).
IČ (CHC13): 3436, 3029, 3024, 3015, 2925, 2871, 2670, 1708, 1659, 1598, 1510/cm.
(a]D = +69,1° (MeOH, c=l,01, 22,0 °C).
Č. 2a-156
CDC13:CD3OD=10:1300 MHz
0,99 (1H, d, J=9,9 Hz), 1,11 a 1,21 (každý 3H, každý s),1,56
- 2,58 (14H, m), 4,22 (1H, m) , 5,35 - 5,59 (2H, m), 6,83(1H, d, J=8,4 Hz), 7,48 (1H, d, J=8,4 Hz), 7,61 (1H, dd, J=l,5 a
8,4 Hz), 8,09 (1H, d, J=l,5 Hz), 8,12 (1H,S).
IČ (KBr): 3422, 3115, 2985, 2922, 2869, 2609, 1708, 1636, 1578, 1529, 1470/cm.
[a]D = +62,8° (MeOH, c=l,01, 22,0 °C).
Č. 2a-157 [0?]D = +40,0° (MeOH, c=0,95, 22,0 °C).
Č. 2a-158
CDC13 300 MHz
1,00 (1H, d, J=10,5 Hz), 1,17 a 1,24 (každý 3H, každý s),
1.54 - 2,50 (14H, m) , 4,34 (1H, m) , 5,36 - 5,52 (2H, m), 7,80 (1H, d, J=9,0 Hz), 9,30 (1H, s).
IČ (CHC13): 3410, 3122, 3030, 3012, 2925, 2871, 2668, 1709, 1667, 1538, 1466/cm.
[ttJD = +44,9° (MeOH, c=0,99, 22,0 °C).
Č. 2a-159
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,13 a 1,22 (každý 3H, každý s),
1.55 - 2,43 (14H, m) , 3,03 (6H, sj , 4,23 (TH, m) , 5,32 - 5,51 (2H, m) , 6,16 (1H, d, J=8,7 Hz), 6,87 a 7,63 (každý 2H, každý d, J=8,7 Hz) .
206
IČ (CHC13): 3457, 3028, 3006, 2924, 2870, 2654, 1739, 1709, 1637, 1608, 1608, 1534, 1501/cm.
[<y]D = +64,8° (MeOH, c=l,01, 22,0 °C) .
Č. 2a-160 dg-DMSO 300 MHz
0,83 (ÍH, d, J=9,9 Hz), 1,02 a 1,19 (každý 3H, každý s), 1,38 - 1,61 (3H, m), 1,90 - 2,32 (11H, m), 3,90 (ÍH, m), 5,41 5,44 (2H, m), 7,32 (ÍH, dd, J=0,9 a 7,2 Hz), 7,45 - 7,60 (2H, m), 7,77 (1H, dd, J=0,9 a 7,8 Hz), 8,03 (ÍH, d, J=6,9 Hz), 12,40 (ÍH, s).
IČ (Nujol): 3315, 2924, 2856, 2656, 2535, 1737, 1703, 1637, 1598, 1581, 1541/cm.
[<X]D = +78,5° (MeOH, C=l,01, 24,0 °C) .
teplota tání 161,0 - 162,0 °C.
Č. 2a-161 (a]D = +65,3° (MeOH, c=l,00, 22,0 °C).
Č. 2a-162
CDC13 300 MHz
0,99 (ÍH, d, J=10,2 Hz), 1,13 a 1,25 (každý 3H, každý s),
1,53 - 2,45 (14H, m), 4,30 (1Ή, m) , 5,36 - 5,51 (2H, m) , 6,32 (ÍH, d, J=8,4 Hz), 7,88 a 8,28 (každý 2H, každý d, J=9,0 Hz). IČ (CHC13): 3448, 3029, 3016, 2925, 2870, 1708, 1664, 1602, 1527, 1484, 1347/cm.
[α]β = +72,7° (MeOH, c=l,02, 22,0 °C).
Č. 2a-163
CDC13 300 MHz
0,96 (ÍH, d, J=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,55 - 2,51 (14H, τη) , 4,26 (1H, m) , 5,36 - 5,57 (2H, m), 6,68 (1H, d, J-7,8 Hz), 7,41 (ÍH, dd, J=4,8 a 8,1 Hz), 8,20 (1H, d, J=8,lHz), 8,66 (ÍH, d, J=4,8Hz), 9,00 (1H, s)IČ (CHC13): 3448, 3026, 3013, 2925, 2870, 2534, 1709, 1658,
1590, 1515, 1471/cm.
207 [θ']D = +71,3° (MeOH, ¢=1,01, 22,0 °C) .
Č. 2a-164 [cd D = +40,80 (MeOH, c=0,98, 22,0 °C) .
Č. 2a-165
CDC13 300 MHz
0,96 (ÍH, d, J=1O,5 Hz), 1,11 a 1,24 (každý 3H, každý s),
1,55 - 2,52 (14H, m), 4,24 (ÍH, m), 5,37 - 5,57 (2H, m), 6,63 (ÍH, d, J=7,8 Hz), 7,59 a 8,63 (každý 2H, každý d, J=6,0 Hz). IČ (CHC13): 3447, 3346, 3028, 3016, 2925, 2870, 2538, 1941, 1708, 1662, 1556, 1516/cm.
[cdD = +75,4° (MeOH, c=l,01, 22,0 °C) .
Č. 2a-166
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,11 a 1,22 (každý 3H, každý s),
1,51 - 2,44 (14H, m) , 2,95 (6H, s), 4,25 (ÍH, m) , 5,33 - 5,50 (2H, m) , 6,19 (ÍH, d, J=8,7 Hz), 6,77 a 6,97 (každý 2H, každý d, J=8,4 Hz), 6,94 a 7,65 (každý 2H, každý d, J=9,0 Hz).
IČ (CHC13): 3453, 3024, 3016, 2924, 2871, 2806, 1739, 1647, 1612, 1604, 1515, 1490/cm.
[cd D = +53,1° (MeOH, ¢=1,02, 23,0 °C).
teplota tání 104,0 až 105,0 °C.
Č. 2a-167
CDC13 300 MHz
1,01 (1H, d, J=9,9 Hz), 1,19 a 1,26 (každý 3H, každý š), 1,56
- 2,53 (14H, m) , 4,37 (1H, Hl) , 5,35 - 5,55 (2H, m) , 6,47 (ÍH.
d, J=8,4 Hz), 7,61 - 7,71 (2H, m) , 7,79 (2H, s), 7,89 - 7,97 (2H, m), 8,27 (ÍH, d, J=2,1 Hz), 8,66 - 8,73 (2H, m).
IČ (CHC13): 3450, 3024, 3014, 2925, 2870, 2667, 1707, 1650,
1531, 1509/cm.
[cdD = +70,5° (MeOH, c=l,00, 22,0 °C).
• · • ·
- 208 Č. 2a-168
CDC13 300 MHz
1,02 (1H, d, J=10,2 Hz), 1,20 a 1,26 (každý 3H, každý s),
1,56 | - 2,50 (14H, | m) , 4,38 (1H, m), | 5,36 | -5,56 (2H, m), 6,51 | ||
(1H, | d, J=8,4 Hz) | , 7,61 | - 7,93 (7H, | m) , 8 | ,74 (1H, d, | J=8,4 |
Hz) , | 9,15 (1H, s) | - | ||||
IČ (CHC13): 3517, | 3451, | 3060, 3028, | 3011, | 2925, 2870, | 2664, |
1709, 1651, 1519, 1498/cm.
[θ']D = +54,4° (MeOH, c=l,00, 23,0 °C) .
Č. 2a-169
CDCl3300 MHz
0,96 (1H, d, J=10,5 Hz), 1,09 a 1,21 (každý 3H, každý s),
1,50 - 2,44 (14H, m), 3,85 (3H, s), 4,24 (1H, m), 5,32 - 5,48 (2H, m), 6,19 (1H, d, J=8,4 Hz), 6,94 a 7,45 (každý 2H, každý d, J=9,0 Hz), 7,11 a 7,45 (každý 2H, každý d, J=8,7 Hz).
IČ (CHC13): 3516, 3453, 3029, 3009, 2925, 2870, 2840, 2665, 1708, 1650, 1593, 1515, 1493, 1482/cm.
[a]D = +57,8° (MeOH, c=l,00, 23,0 °C).
Č. 2a-170
CDC13 300 MHz
0,98 (1H, d, J=10,2 Hz), 1,15 a 1,24 (každý 3H, každý s) ,
1,52
2,50 (14H, m), 4,28 (1H, m), 5,33
5,54 (2H, m), 6,25 (1H, d, J=8,2 Hz), 7,38
7,44 (2H,
m), 7,74 (1H,
s)
7,81 7,86 (2H, m).
IČ (CHC13): 3517, 3448, 3427, 3024, 3013, 2925, 2870, 2669, 1708, 1650, 1562, 1535, 1500/cm.
[a]D = +61,6° (MeOH, c=l,00, 23,0 °C).
Č. 2a-171
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,11 a 1,22 (každý 3H, každý s),
1,52 - 2,42 (14H, m), 2,48 (3H, s), 4,21 (1H, m), 5,31 - 5,52 (2H, m), 6,06 (1H, d, J=8,2 Hz), 6,97 a 7,59 (každý 1H, každý d, J=l,2 Hz).
- 209 IČ (CHC13): 3452, 3113, 3028, 3007, 2925, 2870, 2669, 1708, 1645, 1554, 1509/cm.
[θ'] D = +52,4° (MeOH, c=l,00, 23,0 °C).
Č. 2a-172
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,09 a 1,28 (každý 3H, každý s),
1,50 - 2,40 (14H, m), 2,69 (3H, s), 4,24 (1H, m), 5,35 - 5,51 (2H, m), 5,96 (1H, d, J=8,7 Hz), 7,03 a 7,07 (každý 1H, každý d, J=5,4 Hz).
IČ (CHC13): 3451, 3031, 3013, 2925, 2870, 2666, 1708, 1647, 1542, 1497/cm.
[a]D = +51,2° (MeOH, c=l,00, 23,0 °C).
Č. 2a-173
CDC13 300 MHz
0,95 (1H, d, J=10,2 Hz), 1,10 a 1,23 (každý 3H, každý s),
1,50 - 2,45 (14H, m) , 4,22 (1H, m) , 5,35 - 5,49 (2H, m), 6,05 (1H, d, J=8,4 Hz), 7,26 a 7,75 (každý 1H, každý d, J=l,5 Hz). IČ (CHC13): 3451, 3011, 3029, 3011, 2925, 2870, 1708, 1652, 1538, 1500/cm.
[a]D = +50,6° (MeOH, c=l,01, 23,0 °C).
Č. 2a-174
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,13 a 1,23 (každý 3H, každý s),
1,52 - 2,50 (14H, m), 4,29 (1H, m), 5,35 - 5,51 (2H, m), 7,02 (1H, d, J=8,4 Hz), 7,32 a 8,16 (každý 1H, každý d, J=3,9 Hz). IČ (CHC13): 3417, 3115, 3023, 3014, 2925, 2870, 1708, 1645, 1530/cm.
[a]D = +48,8° (MeOH, c=l,02, 23,0 °C).
Č. 2a-175
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,14 a 1,23 (každý 3H, každý s),
1,50 - 2,52 (14H, m), 2,52 (3H, s), 4,29 (1H, m), 5,34 - 5,51
210
(2H, m) , 7,78 (1H, d, J=9,0 Hz), 7,24 a 7,52 {každý ÍH, každý d, J=5,4 Hz).
IČ (CHC13): 3329, 3093, 3023, 3015, 2871, 2924, 1708, 1640, 1526/cm.
[a]D = +45,0° (MeOH, c=l,01, 23,0 °C) .
Č. 2a-176
CDG13 300 MHz
0,95 (ÍH, d, J=10,5 Hz), 1,09 a 1,23 (každý 3H, každý s),
1,52 - 2,46 (14H, m) , 2,40 (3H, d, J=0,9 Hz), 4,24 (ÍH, m),
5,35 - 5,51 (2H, m), 6,05 (ÍH, d, J=8,7 Hz), 6,95 (ÍH, m), 7,57 (ÍH, d, J=3,3 Hz).
IČ (CHC13): 3517, 3444, 3103, 3024, 3013, 2926, 2870, 1739,
1708, 1649, 1636, 1597/cm.
[a]D = +54,8° (MeOH, c=l,01, 23,0 °C).
teplota tání 97,0 až 99,0 °C.
Č. 2a-177
CDC13 300 MHz
0,97 (ÍH, d, J=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s) ,
1,52 - 2,45 (14H, m) , 3,93 (3H, s) , 4,27 (ÍH, m), 5,34 - 5,50 (2H, m), 6,35 (1H, d, J=3,3 Hz), 7,80 (ÍH, d, J=8,7 Hz), 8,10 (ÍH, d, J=3,3 Hz).
IČ (CHC13): 3395, 3121, 3031, 3019, 3012, 2925, 2871, 1739,
1709, 1640, 1557, 1533/cm.
(a]D = +22,8° (MeOH, c=l,01, 23,0 °C).
teplota tání 109,0 až 112,0 °C.
Č. la-178
CDC13 300 MHz
0,96 (ÍH, d, J=10,5 Hz), 1,10 a 1,23 (každý 3H, každý s),
1,51 - 2,45 (14H, m), 4,24 (ÍH, m), 5,35 - 5,50 (2H, m), 6,09 (ÍH, d, J=8,4 Hz), 7,17 - 7,31 (6H, m), 7,95 (1H, d, J=l,5 Hz) .
IČ (CHC13): 3510, 3451, 3062, 3031, 3022, 3011, 2925, 2870, 2662, 1708, 1651, 1582, 1535, 1497, 1477/cm.
211 [0ř]D = +47,9° (MeOH, c=l,01, 25,0 °C) .
Č. 2a-179
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,14 a 1,24 (každý 3H, každý s),
1,52 - 2,48 (14H, m), 4,30 (1H, m), 5,36 - 5,52 (2H, m), 6,73 (1H, d, J=9,0 Hz), 6,26 a 7,37 (každý 1H, každý d, J=6,0IIz). IČ (CHC13): 3509, 3429, 3115, 3094, 3025, 3014, 2925, 2871, 26.66, 1708, 1649, 1529, 1510/cm.
[O!]d = +51,0° (MeOH, c=l,02, 25,0 °C) .
Č. 2a-180
CDC13 300 MHz
0,95 (1H, d, J=10,2 Hz), 1,14 a 1,24 (každý 3H, každý s),
1,52 - 2,46 (14H, m) , 3,89 (3H, s), 4,21 (1H, m) , 5,35 - 5,50 (2H, τη), 6,05 (1H, d, J=8,4 Hz), 6,46 a 7,04 (každý 1H, každý d, J=l,8 Hz).
IČ (CHC13): 3516, 3450, 3114, 3031, 3010, 2925, 2871, 1708, 1648, 1546, 1511, 1477/cm.
[O?]D = +49,1° (MeOH, c=l,01, 25,0 °C) .
Č. 2a-181
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,14 a 1,23 (každý 3H, každý s),
1.52 - 2,48 (14H, m) , 2,42 (3H, s) , 4,31 (1H, τη) , 5,34 - 5,52 (2H, m) , 8,07 (1H, d, J=9,3 Hz), 7,27 a 8,17 (každý 1H, každý d, J=3,3 Hz) .
IČ (CHC13): 3510, 3301, 3112, 3023, 3007, 2924, 2871, 2663, 1708, 1636, 1534/cm.
[Oř] D = +41,0° (MeOH, c=0,96, 25,0 °C) .
Č. 2a-182
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1.53 - 2,46 (14H, m), 2,51 (3H, s), 4,21 (1H, m), 5,35 - 5,51 (2H, m) , 6,05 (1H, d, J=8,l Hz), 7,26 a 7,78 (každý 1H, každý
212 d, J=l,8 Hz).
IČ (CHC13): 3509, 3450, 3109, 3024, 3012, 2925, 2870, 2666, 1708, 1650, 1535, 1498, 1471/cm.
[a]D = +52,9° (MeOH, C-0,95, 25,0 °C).
Č. 2a-183
CDC13 300 MHz
0,96 (IH, d, J=10,5 Hz), 1,12 a 1,22 (každý 3H, každý s),
1,52 - 2,46 | (14H, | m) , 4, | 25 (IH, m) , | 5,33 - 5,51 | (2H, m), 6,17 |
(IH, d, J=8, | 7 Hz) | , 7,01 | - 7,05 (3H, | m), 7,14 a | 7,62 (každý |
2H, každý d, | J=8, | 7 Hz), | 7,27 - 7,34 | (2H, m) . | |
IČ (CHC13): | 3428, | 3026, | 3015, 2925, | 2870, 2666, | 1739, 1708, |
1643, 1613, | 1594, | 1526, | 1499/cm. |
[o?lD = +64,8° (MeOH, c=l,02, 23,0 °C) .
Č. 2a-184
CDC13 300 MHz
1,01 (IH, d, J=10,2 Hz), 1,18 a 1,26 (každý 3H, každý s),
1,55 - 2,50 (14H, m), 4,35 (IH, m) , 5,35 - 5,55 (2H, m) , 6,42 (IH, d, J=8,7 Hz), 7,46 -7,52 (2H, m), 7,73 (IH, dd, J=l,8 a 8,4 Hz), 7,83 - 7,89 (2H, m), 8,21 (IH, m) , 8,59 (IH, d, J=l,5 Hz).
IČ (CHClg): 3451, 3031, 3014, 2925, 2870, 2660, 1739, 1708, 1650, 1604, 1513, 1463/cm.
[á]D = +58,3° (MeOH, c=l,OO, 23,0 GC) .
Č. 2a-185
CDC13 300 MHz
1,00 (IH, d, | J=10,2 Hz), 1,18 a 1,25 | (každý 3H, každý s), 1,55 | |||
- 2,50 (14H, | m), 4,34 (IH, m), 5,35 | -5,54 | (2Ή, | m) , 6,36 (IH, | |
d, J=8,7 Hz) | , 7,37 (IH, | t, J=7,4 Hz) | , 7,50 | (IH, | m) , 7,57 - |
7,59 (2H, m) | , 7,79 (IH, | dd, J---1,8a | 8,1 Hz) | , 7, | 99 (IH, d, |
J=7,8 Hz), 8 | ,39 (IH, d, | J=l,8 Hz). | |||
IČ (CHC13): | 3451, 3030, | 3020, 2870, | 2665, 1708, | 1652, 1632, | |
1603, 1586, | 1514, 1469, | 1448/cm. |
[a]D = +59,4° (MeOH, c=l,01, 24,0 GC).
- 213 Č. 2a-186
CDC13 300 MHz
1,00 1,54 | (1H, d, J=10,5 Hz), 1,17 a 1,25 (každý 3H, každý s | ) , , 6,37 | |
-2,50 (14H, m), 4,33 (1H, m), 5,35 - 5,54 | (2H, m) | ||
(TH, | d, J=8,7 Hz), 7,37 (1H, t, J=7,4 Hz), 7,51 | (1H, t, | 3=1, 8 |
Hz) , | 7,56 (1H, m), 7,70 (1H, dd, J=l,2 a 8,4 Hz) | , 7,97 | (3H, |
m) . | |||
IČ (CHC13): 3451, 3030, 3014, 2924, 2870, 2671, | 1739, 1708, | ||
1652, | 1577, 1517, 1488, 1471/cm. |
[a]D = +72,2° (MéOH, c=l,00, 24,0 °C) .
Č. 2a-187
CDC13 300 MHZ
1,00 (1H, d, J=9,8 Hz), 1,18 a 1,25 (každý 3H, každý s), 1,54
- 2,53 (14H, m), 4,07 (3H, s), 4,37 (1H, m), 5,30 - 5,54 (2H, m) , 7,34 (1H, m), 7,47 (1H, s) , 7,47 - 7,60 (2H, m), 7,93 (1H, d, J=7,8 Hz), 8,43 1H, s), 8,49 (1H, d, J=9,0 Hz).
IČ (CHC13): 3397, 3074, 3027, 3020, 3009, 2924, 1738, 1708, 1647, 1633, 1534, 1465, 1453/cm.
[a]D = +43,7° (MeOH, c=l,01, 25,0 °C).
Č. 2a-188
CDC13 300 MHz
0,97 (1H, d, J=10,2 Hz), 1,11 a 1,23 (každý 3H, každý s),
1,53 - 2,50 (14H, m) , 4,23 (1H, τη) , 5,37 - 5,50 (2H, m) , 6,10 (1H, d, J=9,0 Hz), 6,20 (1H, m), 6,51 (1H, τη), 6,97 (1H, m), 10,81 ŠS) .
IČ (CHC13) : 3450, 3236, 3112, 3029, 3015, 2925, 2871, 2645, 1701, 1616, 1558, 1516/cm.
[a]D = +50,6° (MeOH, c=l,01, 24,0 °C).
Č. 2a-189
CDC13 300 MHz
0,94 (1H, d, J=9,9 Hz), 1,11 a 1,23 (každý 3H, každý s), 1,50
- 2,46 (14H, τη), 3,93 (3H, s), 4,18 (1H, m), 5,35 - 5,52 (2H,
214
m) , 6,03 (1H, d, J=9,3 Hz), 6,09 (1H, m) , 6,48 (1H, m), 6,73 (1H, m) .
IČ (CHC13) : 3452, 3102, 3028, 3007, 2925, 2871, 2666, 1739, 1708, 1650, 1536, 1499, 1471/cm.
[a]D = +49,8° (MeOH, c=l,01, 23,0 °C).
teplota tání 101,5 až 103,5 °C.
Č. 2a-190
CDC13 300 MHz
0,94 (1H, d, J-10,2Hz), 1,11 a 1,21 (každý 3H, každý s),
1,54 - 2,47 (14H, m) , 4,23 (TH, m), 5,33 - 5,52 (2H, m), 6,06 (1H, d, J=9,0Hz), 6,34 (1H, m) , 6,75 (lfí, m) , 6,36 (1H, m) , 9,71 (1H, šs) .
IČ (CHC13): 3470, 3215, 3030, 3020, 3010, 2925, 2871, 2664, 1709, 1613, 1564, 1510/cm.
[a]D = +43,3° (MeOH, c=l,01, 24,0 °C).
Č. 2a-191
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,11 a 1,22 (každý 3H, každý s),
1,55 - 2,44 (14H, m), 3,66 (3H, S), 4,20 (1H, m) , 5,35 - 5,51 (2H, m), 5,93 (1H, d, J=8,4 Hz), 6,27 (1H, dd, J=l,8 a 2,7 Hz), 6,56 (1H, t, J=2,7 Hz), 7,19 (1H, t, j=l,8 Hz).
IČ (CHC13): 3452, 3031, 3018, 3006, 2925, 2871, 2662, 1736, 1710, 1634, 1609, 1556, 1498/cm.
[of)D = +43,1° (MeOH, C=l,01, 23,0 °C).
Č. 2a-192
CDC13 300 MHz
0,96 (1H, | d, J=10,5 Hz), | 1, 11 | a 1,21 | (každý | 3H, | každý s) , | ||
1,43 (3H, | t, J=7,5 HZ), | 1,54 - | 2,44 | (14H, | m) | , 3 | ,93 | (2H, q, |
J=7,5 Hz), | 4,21 (1H, m), | 5,33 | - 5,51 | (2H, | m) | . 5 | ,94 | (1H, d, |
J=8,4 Hz), | 6,27 (1H, dd, | j=l, 8 | a 2,7 | Hz) , | 6, | 62 | (1H, | t, J=2, |
Hz), 7,26 | (1H, t, J=l,8 | Hz) . | ||||||
IČ (chci3) | : 3630, 3452, | 3032, | 3018, | 3006, | 2925, | 2871, 2661, | ||
1735, 1710, 1633, 1610, | 1555, | 1497/cm. |
- 215 ··«· [a]D = +40,1° (MeOH, c=l,00, 23,0 °C) .
Č. la-193
CDC13 300 MHz
0,95 (1H, d, J=10,2 Hz), 1,10 a 1,22 (každý 3H, každý s),
1,53 - 2,49 (14H, m), 2,58 (3H, s), 4,21 (1H, m) , 5,35 - 5,54 (2H, m), 6,15 (1H, d, J=8,1 Hz), 6,52 (1H, dd, J=l,8 a 3,6 Hz), 7,29 (1H, t, J=3,6 Hz), 7,94 (1H, t, J=l,8 Hz).
IČ (CHC13): 3516, 3450, 3410, 3152, 3027, 3015, 2925, 2871, 2670, 1732, 1648, 1574, 1509/cm.
[cdD = +45,0° (MeOH, C=l,01., 25,0 °C) .
Č. 2a-194
CDC13 300 MHz
0,99 (1H, d, J=10,2Hz), 1,11 a 1,24 (každý 3H, každý s),
1,52 - 2,53 (14H, τη) , 4,34 (1H, m) , 5,33 - 5,57 (2H, m) , 6,21 (1H, d, J=8,6 Hz), 7,35 - 7,50 (2H, m), 7,83 (1H, S), 7,86 (1H, tn) , 8,31 (1H, m) .
IČ (CHC13): 3443, 3067, 3013, 2925, 2870, 2665, 1708, 1651, 1515, 1493/cm.
[a]D = +55,7° (MeOH, c=l,01, 23,0 °C) .
Č. 2a-195
CDC13 300 MHz
1,01 (1H, d, J=10,0 Hz), 1,06 a 1,26 (každý 3H, každý s),
1,50 - 2,64 (14H, τη) , 2,68 (3H, s), 4,40 (1H, m), 5,36 - 5,61 (2H, tn) , 6,02 (1H, d, J=9,4 Hz), 7,30 - 7,42 (2H, m) , 7,73 7,86 (2H, m) .
IČ (CHC13): 3510, 3434, 3062, 3029, 3014, 2924, 2871, 2669, 1708, 1650, 1563, 1539, 1500/cm.
[a]D = +72,4° (MeOH, c=l,00, 23,0 °C).
teplota tání 111,0 až 112,0 °C.
Č. 2a-196
CDC13 300 MHz
0,42 a 1,04 (každý 3H, každý s), 0,80 (1Ή, d, J= 10,0 Hz),
216
1,11 - 2,48 (14H, m), 2,24 (3H, s), 4,02 (1H, m) , 5,23 - 5,44 (2H, m), 5,53 (1H, d, J-8,8 Hz), 7,27 - 7,31 (2Ή, m), 7,42 7,48 (3H, m), 7,93 (1H, s).
IČ (CHC13): 3419, 3114, 3025, 3006, 2924, 2871, 2662, 1737, 1709, 1636, 1540, 1519/cm.
[O?]D = +43,7° (MeOH, c=l,01, 23,0 °C) .
Č. 2a-197
CDC13 300 MHz
0,95 (1H, d, J=10,0 Hz), 1,09 a 1,23 (každý 3H, každý s),
1.54 - 2,46 (18H, m), 2,77 (4H, šs), 4,21 (1H, m), 5,32 -
5.54 (2H, m), 6,02 (1H, d, J=8,6 Hz), 7,43 (1H, s).
IČ (CHC13): 3445, 3ΓΟ1, 3024, 3014, 2928, 2865, 2661, 1739, 1708, 1646, 1550, 1507/cm.
[a]D = +51,9° (MeOH, c=l,01, 23,0 °C) .
Č. 2a-198
CDC13 300 MHz
0,96 (1H, d, J=1O,2 Hz), 1,11 a 1,22 (každý 3H, každý s),
1.50 - 2,44 (14H, m), 4,24 (1H, m), 4,42 (2H, s), 5,35 - 5,49 (2H, m), 6,25 (1H, d, J=8,l Hz), 7,33 (1H, m), 7,43 (1H, dd, J=l,5 a 7,5 Hz), 7,49 (1H, d, J=8,l Hz), 7,60 - 7,63 (1H, m), 7,68 (1H, dd, J=l,8 a 7,8 Hz), 8,02 (lfí, d, J=l,8 Hz), 8,19 (1H, dd, J=l,5 a 8,1 Hz).
IČ (CHC13): 3448, 3030, 3012, 2925, 2870, 1739, 1708, 1671, 1588, 1559, 1514, 1472/cm.
[a]D = +56,9° (MeOH, c=l,01, 24,0 °C).
Č. 2a-199
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,11 a 1,22 (každý 3H, každý s),
1.51 - 2,46 (14H, m), 3,40 (1H, m), 3,76 (1H, m), 4,24 (1H, m), 5,33 - 5,51 (3H, m) , 6,25 (1H, m), 7,16 (1H, m), 7,24 7,33 (2H, m), 7,46 (1H, d, J=7,5 Hz), 7,52 - 7,60 (2H, m) , 7,85 (ÍH, dd, J=l,8 a 4,5 Hz).
IČ (CHC13): 3583, 3447, 3062, 3028, 3013, 2924, 2871, 2663,
217
1708, 1651, 1600, 1557, 1514, 1471/cm.
[a]D = +54,8° (MeOH, C=l,00, 23,0 °C) .
Č. 2a-200
CDC13 300 MHz
0,96 (IH, d, J=10,2 Hz), 1,12 a 1,23 (každý 3H, každý s) ,
1,51 - 2,46 (14H, m), 4,25 (1H, m), 5,34 - 5,51 (2H, m) , 6,25 (1H, d, J=8,4 Hz), 7,02 a 7,10 (každý 1H, každý d, J=12,3 Hz), 7,23 - 7,33 (4H, m), 7,50 (1H, m), 7,64 (1H, dd, J=l,8 a 7,8 Hz), 7,82 (IH, d, J=l,8 Hz).
IČ (CHC13): 3450, 3060, 3025, 3014, 2925, 2871, 2662, 1708, 16.53, 1596, 1542, 1513, 1473/cm.
[a]D = +62,5° (MeOH, c=l,00, 24,0 °C).
Č. 2a-201
CDC13 300 MHz
0,95 (IH, d, J=9,9 Hz), 1,15 a 1,22 (každý 3H, každý s), 1,55 - 2,60 (14H, m), 4,26 (IH, m), 5,35 - 5,63 (2H, m) , 7,14 (1H, d, J=9,9 Hz), 7,34 a 7,40 (každý 1H, každý d, J=12,9 Hz),
7,62 | - 7,73 | (4H, m) , 8,25 - 8,30 (2H, m), 8,72 (1H, d, | J=1,5 | |||
Hz) . | ||||||
IČ (CHC13): | 3443, 3389, | 3297, | 3061, 3030, | 3016, 2925, | 2870, | |
1726, | 1708, | 1652, 1603, | 1521, | 1483, 1472, | 1309/cm. | |
[a]D | = +61, | 1° (MeOH, C= | 1,01, | 23,0 °C). |
Č. 2a-202
CDC13 300 MHz
0,96 (1H, d, J=10,2 Hz), 1,09 a 1,22 (každý 3H, každý s),
1,52 - 2,43 (14H, m), 2,63 (3H, S), 4,25 (IH, m), 5,33 - 5,49 (2H, m) , 6,19 (1H, d, J=8,4 Hz) , 7,10 a 7,58 (každý 2H, každý
d, J=9,0 Hz), 7,21 (1H, | m), 7 | ,30 - 7,32 (2H, m), 7,46 | (IH, d, |
J=7,5 Hz). | |||
IČ (CHC13): 3511, 3453, | 3062, | 3032, 3014, 2925, 2870, | 1739, |
1708, 1650, 1595, 1556, | 1516, | 1482, 1471/cm. | |
[a]D = +60,2° (MeOH, c= | 1,01, | 25,0 °C). |
·«·· ·· «· * · · · · • · · ···· ····
218
9 9 9 9 9 · · ···· ·
9 · · ··· ···
Č. 2a-203
0,96 (ÍH, d, J=10,5 Hz), 1,09 a 1,23 (každý 3H, každý s),
1,52 - 2,43 (14H, m) , 4,23 (1H, m), 5,35 - 5,51 (2H, m), 5,93 (ÍH, d, J=8,7 Hz), 6,56 (ÍH, dd, J=0,9 a 1,8 Hz), 7,43 (ÍH, t, J=l,8 Hz), 7,92 (TH, dd, J=0,9 a 1,8 Hz).
IČ (CHClj): 3517, 3450, 3134, 3031, 3008, 2925, 2870, 2667, 1708, 1656, 1588, 1570, 1514/cm.
[a]D = +46,7° | (MeOH, | c=0,92, | 25,0 | °C) . |
Č. 2b-l Ia]D = +25,6° | (MeOH, | c=l,01, | 23,0 | °C) . |
Č. 2b-2 [«]D = +38,9° | (MeOH, | C=l,01, | 24,0 | °C) . |
Č. 2C-1 [a]D = +60,5° | (MeOH, | C=l,01, | 22,0 | °C) . |
Č. 2c-2 [a]D = +55,8° | (MeOH, | c=0,92, | 22,0 | °C) . |
Č. 2c-3 [a]D = +54,7° | (MeOH, | c=l,01, | 22,0 | °C) . |
Č. 2d-l [Of]D .= -6,2° (MeOH, c=l,00, 21,0 °C) .
Č. 2d-2 [a]D = +15,8° (MeOH, c=0,34, 22,0 °C).
Č. 2d-3 [a]D = +31,6° (MeOH, C=l,01, 22,0 °C).
Č. 2e-l [cdD = -9,4° (MeOH, c=l,00, 22,0 °C) .
• ·
- 219 Č. 2e-2
[Of] | D = -1'80 | (MeOH, | c=l,02, | 23,0 | °C) . |
Č. | 2e-3 | ||||
[a] | D - b, / | (MeOH, | c=l,01, | 23,0 | °G) . |
č. | 2f-l | ||||
[Qf] | D = +6,8° | (MeOH, | C=l,01, | 23,0 | °C) . |
Č. | 2f-2 | ||||
[Of] | - -2 6° D - o | (MeOH, | C = l,00, | 22,0 | °C) . |
v c. | 2f-3 | ||||
[a] | P - 5 | (MeOH, | c=l,01, | 22,0 | °C) . |
Č. | 2g-l | ||||
[Qf] | p = +54,6° | (MeOH, | c=l,Ol, | 24,0 | °C) |
Č. 3a-2
CDC13 300 MHz
0,98 - 2,15 (14H, m) , 2,31 (2H, t, J=7,2 Hz), 2,35 - 2,40 (1H, m), 3,10 - 3,20 (1H, m), 5,00 (1H, d, J=6,9 Hz), 5,30 5,48 (2H, m), 6,75 (1H, d, J=10,2 Hz), 7,38 - 7,52 (6H, m). IČ (CDC13): 3266, 3028, 2954, 2874, 1709, 1620, 1448, 1412, 1318, 1141, 970, 892/cm.
[Qfjp = +23,3 ± 0,6° (CHC13, C=l,05, 24,0 °C) .
Č. 3a-3
CDC13 300 MHz
0,95 - 2,00 (14H, m), 2,20 - 2,29 (3H, m), 3,00 - 3,08 (1H,
m) , 3,66 (3H, s), 5,00 (1H, d, J=6,6 Hz), 5,13 - 5,29 (2H,
m) , 7,38 - 7,52 (3H, m) , 7,59 - 7,65 (2H, m) , 7,69 - 7, 75 (2H, m), 7,92 - 7,98 (2H, m).
IČ (CHG13): 3376, 3018, 2946, 2868, 1727, 1594, 1436, 1395,
1322, 1157, 1095, 890/cm.
[Of] D = +2,3 + 0,4° (CHC13, c=1,03, 22,0 °C) .
220 teplota tání 65 až 66,5 °C.
Č. 3a-4
CDC13 300 MHz
0,93 - 2,05 (14H, m), 2,15 - 2,22 (1H, m), 2,31 (2H, t, J=7,2
Hz), 3,01 - 3,10 (1H, m), 5,18 - 5,31 (3H, m), 7,38 - 7,52 (3H, m) , 7,58 - 7,66 (2H, m) , 7,98 (2H, m).
IČ (CHC13): 3374, 3260, 3020, 1396, 1319, 1156, 1095, 1052, [a]D = + 13,1 ± 0,5° (CHC13, c
7,69 - 7,76 (2H, m), 7,92 2948, 2868, 1708, 1594, 1479,
891/cm.
1,16, 24,0 °C) .
Č. 3a-6
CD30D 300 MHz
1,04 - 1,95 (14H, m), 2,07 (2H, t, J=7,8 Hz), 2,14 - 2,22 (1H, m), 2,94 - 3,00 (1H, m), 5,04 - 5,25 (5H, m) , 7,36 -
7,52 (3H, m), 7,66 - 7,71 (2H, m), 7,78 - 7,85 (2H, m), 7,91 - 7,97 (2H, m).
IČ (KBr): 3421, 3278, 2951, 2872, 1562, 1481, 1409, 1317, 1156, 1097, 1057, 895/cm.
[a]D = -15,3 + 0,5° (CHC13, c=l,06, 23,0 °C).
Č. 3a-ll
CDC13 300 MHz
0,90 - 2,04 (14H, m) , 2,08 - 2,19 (1H, m) , 2,35 (2H, t, J=7,2 Hz), 2,95-3,04 (1H, m), 5,17 - 5,32 (3H, m), 7,56 - 7,63 (2H, m), 7,83 - 7,95 (2H, m).
IČ (CHC13): 3260, 3020, 2948, 2868, 1707, 1569, 1456, 1383, 1325, 1268, 1160, 1088, 1053, 1006, 892/cm.
[tt]D = +8,3 + 0,5° (CHC13, c=l,00, 22,0 °C).
Č. 3a-16
CDC13 300 MHz
0,80 - 1,90 (14H, τη) , 1,98 - 2,04 (1H, m), 2,27 (2H, t, J=7,2
Hz), 2,88 (6H, S), 2,90 - 2,98 (1H, m), 4,88 - 5,00 (2H, m),
5,13 (1H, d, J=7,2Hz), 7,18 (1H, d, J=7,5Hz), 7,48 -7,60 • β • ·
- 221 (2Η, m), 8,25 - 8,33 (2Η, m), 8,53 (1Η, d, J=8,7 Hz).
IČ (CHC13): 3272, 3020, 2946, 2866, 2782, 1708, 1573, 1455, 1407, 1311, 1229, 1160, 1142, 1070, 942, 891/cm.
[a]D = -19,7 ± 0,6° (CHC13, c=l,08, 23,5 °C) . teplota tání 105 až 112 °C.
Č. 3a-31
CDC13 300 MHz
0,80 - 1,85 (14H, m), 2,02 - 2,08 (1H, m), 2,20 (2H, t, J=7,2 Hz), 2,85 - 2,95 (1H, m) , 3,68 (3H, s), 4,80 - 4,92 (2H, m) ,
4,96 (TH, d, J=6,9 Hz), 7,50 - 7,70 (3H, m) , 7,92 - 7,98 (1H, m), 8,07 (1H, d, J=8,4 Hz), 8,29 (1H, d, J=l,5 & 7,5 Hz),
8,65 (1H, d, J=8,7 Hz).
IČ (CHC13): 3374, 3016, 2946, 2868, 1727, 1506, 1435, 1318, 1160, 1133, 1105, 1051, 984, 890/cm.
[ce]D = -39,3 + 0,8° (CHC13, C-1,07, 22,0 °C) .
Č. 3a-32
CDC13 300 MHz
0,80 - 1,90 (4H, m) , 1,95 - 2,05 (ÍH, m), 2,27 (2H, t, J=7,2 Hz) , 2,90 - 2,96 (TH, m) , 4,85 - 5,00 (2H, m) , 5,23 (1H, d, J=6,6 Hz), 7,50 - 7,72 (3Ή, m) , 7,95 (1H, d, J=8,l Hz), 8,07 (1H, d, J=8,4 Hz), 8,29 (1H, dd, J=l,2 & 7,5 Hz), 8,66 (1H, d, J=9,0 Hz).
IČ (CHC13): 3270, 3020, 2948, 2868, 1708, 1455, 1412, 1317, 1159, 1132, 1104, 1079, 1051, 983, 891/cm.
[a]D = -29,2 ± 0,6° (CHC13, c=l,08, 22,0 °C).
Č. 3a-33
CD3OD 300 MHz
0,94 - 1,84 (14H, m) , 1,96 - 2,08 (3H, m) , 2,77 - 2,84 (III,
m) , 4,67 - 4,84 (2H, m) , 7,55 - 7,75 (3H, m), 8,02 (1H, d,
J=7,8 Hz), 8,12 - 8,26 (2H, m) , 8,74 (1H, d, J=8,7 Hz).
IČ (KBr): 3432, 3298, 2951, 2872, 1564, 1412, 1315, 1159,
1134, 1107, 1082, 1058, 986/cm.
[á]D = -79,9 + 1,2° (CH3OH, c=1,00, 23,0 °C) .
- 222 Č. 3a-34
CDC13 300 MHz
0,97 - 1,91 (14H, m) , 2,13 - 3,20 (1H, m), 2,42 (2H, t, J=7,2 Hz), 3,00 - 3,07 (1H, m) , 5,06 - 5,24 (2H, m), 5,33 (1H, d, J=6,9 Hz), 7,57 - 7,68 (2Η, m), 7,82 - 8,00 (4H, m) , 8,45 (1H, d, J=l,2 Hz).
IČ (CHC13): 3260, 3020, 2948, 1708, 1408, 1319, 1154, 1129, 1073, 953, 893/cm.
[o?]D = +20,7 ± 0,6° (CH3OH, C=1,O7, 22,0 °C) .
Č. 3a-35
CD3OD 300 MHz
1,03 - 2,20 (m, 17H) , 2,97 (m, 1Η), 5,02 (m, 2H), 7,64 (m, 2H), 8,00 (m, 4H), 8,43 (s, 1H).
IČ (KBr): 3360, 3285, 1562, 1407, 1316, 1153, 1130, 1075/cm. (cd D = 0 [áÍ365 = +20-9 i °'6° (CH3OH, c=l,04, 23,0 °C).
Č. 3d-l
CDC13 300 MHz
0,93 - 2,55 | (m, 17H), 3,02 (m, 1H), 5,24 | (m, 2H) , | 6,48 | (m, | |
1H), 7,35 - | 7,60 (m, 3H), 7,85 - 8,00 (m, | 2H) . | |||
IČ (Nujol): | 3275, 1548, 1160, 1094, 758, | 719, 689, | 591, | ||
557/cm. | |||||
[a]D = +19,0 | i 0,6° (CH30H, c=l,010, 26,5 | °C) . | |||
Elementární | analýza (C20H26NO4S l/2Ca 1,0 | h2o) | |||
vypočteno: | C, 57,94; H, 6,82; N, 3,38; | Ca, 4,83; | h2o, | 4, | 35 |
nalezeno : | C, 57,80; H, 6,68; N, 3,68; | Ca, 5,06; | h2o, | 4, | 50 |
Č. 3d-6 | |||||
[a]D = -20,7 | ± 0,6° (CHC13, c=1,00, 24,0 | °C) . |
Č. 3d-7 [a]D = -3,2 + 0,4° (CHC13, C=1,O3, 22,0 °C).
teplota tání 65 až 67 °C.
• · · · • · « ·
- 223 -
Č. 3d-8 | (chci3, | C-1,07, | 24,0 | °C) . | ||
[a]D = -14,5 ± | 0,5° | |||||
Č. 3d-9 [oe] ρ = +12,2 teplota tání | + 0,5° 119 až | (ch3oh, 125 °C. | c=l,00, | 23,0 | °C) . | |
Č. 3d-10 [d]D = +39,7 | + | 0,8° | (chci3, | c=l,07, | 22,0 | °C) . |
Č. 3d-ll [°dj) ~ +29,2 | ± | 0,7° | (chci3, | C=1,06, | 22,0 | °C) . |
Č. 3d-12 [odD = +76,4 | + | 1,1° | (ch3oh, | C=l,03, | 24,0 | °C) . |
Č. 3d-14 [tt] j-j = -20,6 | + | 0,6° | (CHC13, | c=l,07, | 22,0 | °C) . |
Č. 3d-15 [α)365 = 28'° ± °'7° (CH30H, c=1,03, 24,5 °C).
Č. 3d-16 [a]D = -8,7 + 0,7° (CHC13, c=l,06, 22,0 °C) .
Č. 3d-17
CDC13 300 MHz
0,80 - 2,15 (m, 24Η) , 2,32 (t, J=7 Hz, 2H), 2,68 (t, J-7 Hz,
2H), 3,02 (m, 1H), 2,15 (m, 24H), 2,32 (t, J=7 Hz, 2H), 3,02 (m, 1H), 5,22 (m, 2H), 5,38 (d, J=7 Hz, 1H), 7,30 (A2B2q-Apart, J=8 Hz, 2H), 7,81 (A2B2q-Bpart, J=8 Hz, 2H),
9,86 (šš, 1H).
ía]D = o ta]365 = ~9'7 ± °'5° <CHC13- 0=1,03, 22,0 °C) .
φ φ
- 224 Č. 3d-24 (0!]d = +19,2 + 0,6° (CHC13, c=1,05, 23,0 °C) .
Č. 3d-26
CD3OD 300 MHz
0,90 - 2,20 (20H, m), 2,88 (1Ή, m) , 3,07 (2H, q, J=7,0 Hz),
5,00 - 5,40 (2H, m) , 7,20 - 7,60 (4H, ttl) , 7,95 (ÍH, m) .
IČ (KBr): 3415, 3254, 1698, 1564, 1314, 1154/cm.
Č. 3d-28
CD3OD 300 MHz
0,90 - 2,20 (20H, m), 2,73 (2H, q, J=7,0 Hz), 2,93 (1H, m), 5,00 - 5,30 (2H, m), 7,40 - 7,50 (2H, m) , 7,60 - 7,77 (2H, m) .
IČ (KBr): 3435, 3280, 1562, 1323, 1304, 1151/cm.
Č. 3d-30
Elementární analýza (C2QH25BrN4OSNa) | ||||
vypočteno: | C, 50,21; H, Na, 4,81 | 5,27; | Br, | 16,70; N, 2,93; S, 6,70; |
nalezeno: | C, 50,22; H, | 5,40; | Br, | 15,57; N, 2,88; S, 6,41; |
Na, 5,10 |
IČ (KBr): 3425, 3280, 3085, 1697, 1570, 1410, 1321, 1165, 1155/cm.
Č. 3e-l
CD3OD 300 MHz
0,71 (ÍH, d, J-10,2 Hz), 1,04 (3H, s) , 1,12 (3H, s), 1,35 2,28 (14H, m), 2,42 (3H, s) , 3,17 - 3,25 (ÍH, m), 5,18 - 5,39 (2H, m) , 7,37 (2H, d, J=8,4 Hz), 7,75 (2H, d, J=8,4 Hz).
IČ (CHC13): 3400, 3289, 2986, 2924, 2870, 1559, 1424, 1322, 1305, 1160, 1095, 1075, 1030/cm.
[a]D = + 25,9 ± 0,7° (CH3OH, c=l,00, 23,0 °C).
Sloučeniny připravené v příkladech shora byly testovány na in vivo a in vitro účinnost podle způsobu • · « ·
225 ···· ·· • · • · popsaném v experimentálních příkladech dále.
Pokus 1 Vazba na receptor PGD2 Materiál a způsob (1) Příprava membránové frakce lidské krevní destičky
Vzorek krve získaný za použití plastické injekční stříkačky obsahující 3,8% roztok citrátu sodného ze žíly zdravého dobrovolníka (dospělý muž nebo žena) se vloží do plastické zkušební zkumavky a jemně se míchá překlápěním. Vzorek se potom odstřeďuje při 1800 otáčkách/min. podobu 10 minut při teplotě místnosti a supernatant obsahující plasmu bohatou na krevní destičky se sebere. Tato plasma se znovu odstřeďuje při 2300 otáčkách/minutu po dobu 22 minut při teplotě místnosti a získají se krevní destičky. Krevní destičky se homogenizují za použití homogenizéru (Ultra-Turrax) a následuje 3x odstředění při 20 000 otáčkách/minutu po dobu 10 minut při teplotě 4 °C a získá se membránová frakce krevních destiček. Po stanovení proteinu se membránová frakce upraví na objem 2 mg/ml a uloží se do mrazáku při -80 °C do použití.
(2) Vazba na receptor PGD2
K reakčnímu roztoku na zkoušku vazby (50 mM Tris/HCl, pH 7,4, 5 mM MgCl2) (0,2 ml) se přidá lidská membránová frakce krevních destiček (0,1 mg) a 5 nM [3H]PGD2 (115ci/mmbl) a nechá se proběhnout reakce při 4 GC po dobu 90 minut. Po skončení reakce se reakční směs filtruje přes skleněný filtrační papír, promyje se několikrát studeným fyziologickým roztokem a měří se radioaktivita zbylá na filtračním papíru. Specifická vazba se -vypočte odečtením nespecifické vazby (vazba v přítomnosti 10 μΜ PGD2) od celkové vazby. Účinnost inhibice vazby každé sloučeniny se vyjádří jako koncentrace požadovaná pro 50% inhibici (IC^q) a která se stanoví zobrazením subsituční křivky vynesením vazebného poměru (%) v přítomnosti každé sloučeniny, kde vazebný poměr v nepřítomnosti testované sloučeniny je 100 %. Výsledky jsou uvedeny v tabulce dále
- 226 -
Sloučenina č. | Účinnost (μΜ) | Sloučenina č. | Účinnost |
3 a-4 | 0,6 | 2a-4 | 0,54 |
la-115 | 8,6 | 2a-17 | 0,12 |
la-28 | 0,045 | 2a-21 | 5.2 |
la-47 | 0,0086 | 2 a-2 8 | 0,046 |
la-100 | 0,56 | 2a-95 | 1,6 |
la-176 | 0,047 | 2a-109 | 0,003 |
la-2 | 0,13 | la-162 | 0,027 |
Pokus 2 Hodnocení antagonistické účinnosti proti receptoru PGD2 za použití lidských krevních destiček
Periferní krev se získá od zdravého dobrovolníka za použití plastické injekční stříkačky do které bylo předem přidáno 1/9 objemu roztoku kyseliny citrónové a dextrózy. Injekční stříkačka se odstředuje při 180 g po 10 minut a získá se supernatant (plasma bohatá na krevní destičky). Tento supernatant se promyje 3x fyziologickým roztokem a počet krevních destiček se stanoví mikrobuněčným sčítačem. Suspenze se upraví na obsah krevních destiček na konečnou koncentraci x 108/ ml a zahřívá se na 37 °C a potom se předběžně zpracuje 3-isobutyl-l-methylxanthinem (0,5 mM) po dobu 5 minut. K suspenzi se přidá testovaná sloučenina zředěná ha různé koncentrace. O 10 minut později se indukuje reakce přidáním 0,1 až 2,0 μΜ PGD2 a o 15 minut později se reakce zastaví přidáním HC1. Krevní destičky se zničí v ultrazvukovém homogenizéru. Po odstředění se stanoví cAMP v supernatantu radiozkouškou. Antagonismus receptoru PDG2 léčiva se stanoví následovně. Inhibiční poměr odpovídající cAMP zvýšenému přidáním PGD2 se stanoví při individuální koncentraci a potom se určí koncentrace léčiva potřebná pro 50% inhibici (IC5q). Výsledky jsou uvedeny v tabulce dále.
···· ·· ·· · ·* ·· • · · · · ·· ···* • · · 9 9 · ··«· • · 9 9 · « « « · · « · · ···· 9 9 · 9 9 9 ·· ·· ·· ··· 99 99
- 227
Sloučenina č. | Inhibice zvýšení cAMP lidských krevních destiček (IC50)(μΜ) |
3 a-16 | 0,37 |
la-12 | 12,11 |
la~ 28 | 0,30 |
la-47 | 2,09 |
2 a-2 | 0,77 |
2a-4 | 0,94 |
2a-35 | 1,52 |
2a-75 | 0,71 |
Pokus 3 Pokus využívající nazální okluzní model
Pokus používaný pro měření odolnosti nazální dutiny a vyjadřující antinazální okluzi používající morčata je popsán dále.
1% ovalbuminový (OVA) roztok se zpracuje na aerosol v ultrazvukvém zmlžovači. Hartleyovy morčata se sensitizují inhalací dvakrát aerosolem po dobu 10 minut v týdenním intervalu. Sedm dní po sensitizaci se morčata vystaví působení antigenu k vyvolání reakce. Potom se trachea nařízne pod anestézií pentobarbitalem (30 mg/kg intraperitorálně) a kanyly se zavedou do trachey na pulmonární a nazální straně. Kanál zavedený na pulmonární straně se spojí s umělým dýchacím přístrojem který dodává 4 ml vzduchu 60 krát/minutu. Po úpravě spontánního dýchání u morčat pomocí Garaminu (2 mg/kg, intravenózně) se vzduch dodává na nosní stranu umělým dýchacím přístrojem při frekvenci 70 krát/minutu a rychlosti průtoku 4 ml/dávku vzduchu a atmosférický tlak požadovaný pro aeraci se měří použitím elektromechanického převodníku umístěným v přívodu. Měření se použije jako parametr rezistence nazální dutiny. Vystavení antigenu se provádí vytvořením aerosolu z 3% roztoku OVA po dobu 3 minut mezi dýchacím přístrojem a kanylou nazální dutiny. Testovaná sloučenina se injektuje 10 minut před ··· ·
- 228 zavedením antigenu. Nazální rezistence v intervalu O až 30 minut se měří kontinuálně a účinek se vyjádří jako inhibiční poměr k účinku který se získá pro vehikulum užívající AUC po dobu 30 minut (na vertikální ose, rezistence nazální dutiny (cm H2O) a na horizontální ose, čas (0 až 30 minut). Výsledky jsou uvedeny dále.
Sloučenina č.
Inhibiční poměr (%)
Poznámka mg/kg (intravenózně)
la-28 | 44 |
la-98 | 69 |
la-100 | 50 |
la-115 | 66 |
ia-116 | 48 |
ia-120 | 58 |
la-2 | 82 |
la-162 | 80 |
la-176 | 60 |
la-267 | 62 |
2a-4 | 60 |
2a-21 | 52 |
2a-28 | 54 |
2a-95 | 77 |
2a-96 | 77 |
2a-109 | 73 |
2a-110 | 66 |
22a-194 | 79 |
mg/kg (i.v.) mg/kg (p.o.) mg/kg (p.o.)
Formulace 1
Příprava tablet
Tablety, každá obsahující 40 mg aktivní složky se připraví konvenčním způsobem. Složky pro 40 mg tabletu jsou následuj ící:
(+)-(Z)-7-((1R,2S,3S,4S)-3229 benzensulfonamidobicyklo[2.2.1]hept-2-yl]5-heptenoát vápenatý, dihydrát 40,0 mg hydroxypropylcelulóza 3,6 mg stearát hořečnatý 0,4 mg kukuřičný škrob 18,0 mg laktóža 58,0 mg
Celkem 120,0 mg
Formulace 2
Příprava granulí
Složky:
( + )- (Z)-7-((1R,2S,3S,4Š)-3benzensulfonamidobicyklo[2.2.1]hept-2-yl] -
5-heptenoát vápenatý, dihydrát | 100,0 mg |
hydroxypropylcelulóza | 30,0 mg |
karmelóza vápenatá | 30,0 mg |
talek | 10,0 mg |
Poloxamer 188 | 20,0 mg |
krystalická celulóza | 70,0 mg |
kukuřičný škrob | 300,0 mg |
laktóza | 440,0 mg |
Celkem 1000,0 mg
PATBNTSBRVXS
Claims (16)
1. Antagonist PDG2, vyznačující se tím, že jako aktivní složku obsahuje sloučeninu obecného vzorce I uvedený dále nebo její sůl nebo hydrát kde z x1 x2 x3
A je alkylenová skupina, která je případně přerušena heteroatomem nebo fenylenem a obsahuje oxoskupinu a/nebo
X2 je jednoduchá vazba, skupina -N=N~, -N=CH-, -CH=N-, -CH=N-N-, -CH=N-O-,-C=NNHCSNH-, -C=NNHCONH-, -CH=CH-, nenasycenou vazbu;
B je vodík, alkyl, aralkyl nebo acyl;
R je skupina COORlf CH2OR2 nebo CON(R3)(R4);
R4 j e vodík nebo alkyl ,R2 je vodík nebo alkyl ,R3 a R4 jsou nezávisle vodík, alkyl, hydroxyskupina nebo alkylsulfonyl;
X4 je jednoduchá vazba, fenylen, naftylen, thiofendiyl, indoldiyl nebo oxazoldiyl ,231
-CH(OH)-, -C(C1)=C(C1)-, -(CH2)n-, ethinylen, -N(R5)-,
-N(R51)CO-, -N(R52)SO2-, -N(R53)CON(R54)-, -CON(R55)-, -SO2N(R56)-, -Ό-, -S-, -S0-, -S02-, -C0-, oxadiazoldiyl, thiadiazoldiyl, tetrazoldiyl;
X3 je alkyl, alkenyl, alkinyl, aryl, aralkyl, heterocyklická skupina, cykloalkyl, cykloalkenyl, thiazolinylidenmethyl, thiazolidinylidenmethyl, -CH=NRg nebo -N-C (R·?) Rg ;
R5, R52, r52' r53' r54 a r55 znamenají každý vodík nebo alkyl;
Rg je vodík, alkyl, hydoxyskupina, alkoxyskupina, karbamoyloxyskupina, thiokarbamoy1oxyskupina, ureidoskupina nebo thioure idoskupina,·
R7 a Rg znamenají každý nezávisle alkyl, alkoxyskupinu nebo aryl ;
n je 1 nebo 2,Z je skupina -S02- nebo -CO- a m j e 0 nebo 1, kde cyklický subsituent může obsahovat jeden až tři substituenty vybrané ze souboru, který zahrnuje nitroskupinu, alkoxyskupinu, sulfamoylovou skupinu, substituovanou nebo nesubstituovanou aminoskupinu, acylskupinu, acyloxyskupinu, hydroxyskupinu, halogen, alkyl, alkinyl, karboxyskupinu, alkoxykarbonyl, aralkoxykarbonyl, aryloxykarbonyl, mesyloxyskupinu, kyanoskupinu, alkenyloxyskupinu, hydroxyalkyl, trifluormethyl, alkylthioskupinu, skupinu -N=PPh3, oxoskupinu, thiooxoskupinu, hydroxyiminoskupinu, alkoxyiminoskupinu, fenyl a alkylendioxyskupinu.
2. Antagonist PDG2 podle nároku 1, vyznačující se t í m, že jako aktivní složku obsahuje sloučeninu obecného vzorce I, kde
- 232 je m je 0; a kde Z je SO2, obě Χχ a X2 jsou jednoduchá vazba; X je alkyl, fenyl, naftyl, styryl, chinolyl nebo thienyl; a cyklický substituent mezi těmito substituenty obsahuje případně jeden až tři substituenty vybrané ze souboru, který zahrnuje alkoxyskupinu, substituovanou nebo nesubstituovanou aminoskupinu, halogen, alkyl a hydroxyalkyl nebo její sůl nebo hydrát.
3. Antagonist PDG2 podle nároku 1, vyznačuj ící se t í m, že jako aktivní složku obsahuje sloučeninu obecného vzorce I, kde je kde m je 1, obě X-^ a X2 jsou jednoduchá vazba; a X3 je fenyl, případně substituovaný halogenem nebo její sůl nebo hydrát.
4. Antagonist PDG2 podle nároku 1, vyznačující se t í m, že jako aktivní složku zahrnuje sloučeninu obecného vzorce I, kde
233 je kde m jel, Χχ je fenyl, X2 je -CH2- nebo -N=N- a X3 je fenyl nebo její sůl nebo hydrát.
5. Antagonist PDG2 podle nároku 1, který je léčivo pro léčbu nazální okluze.
6. Bicyklická sloučenina obecného vzorce Ia,
B kde A, B, R, Χχ, X2 a X3 jsou jak definováno shora nebo její sůl nebo hydrát s tím, že nejsou zahrnuty ty sloučeniny, kde (1) Χχ a X2 znamenají jednoduchou vazbu a X3 je substituovaný nebo nesubstituovaný fenyl nebo naftyl; a (2) A je 5-heptenylen, R je COOR1 (Κχ je vodík nebo methyl), Xj je 1,4-fenylen, X2 je jednoduchá vazba a X3 je fenyl.
7. Bicyklická sloučenina podle nároku 6, její sůl nebo hydrát, kde X-l a X2 znamenají jednoduchou vazbu, X3 je isoxazolyl, thiadiazolyl, isothiázolyl, morfolyl, indolyl, benzofuryl, dibenzofuryl, dibenzodioxinyl, benzothienyl, dibenzothienyl, karbazolyl, xanthenyl, fenantridinyl, dibenzoxepinyl, dibenzothiepinyl, cinnolyl, chromeny!, benzimidazolyl nebo dihydrobenzothiepinyl a A, B a R mají význam uvedený shora.
8. Bicyklická sloučenina podle nároku 6, její sůl nebo
234 hydrát, kde X3 je jednoduchá vazba, X2 je fenylen, X3 je alkenyl, alkinyl, -CH=NRg nebo -N=C(R7)Rg, a A, B, R, Rg, R7 a Rg mají význam definovaný shora.
9. Bicyklická sloučenina podle nároku 6, její sůl nebo hydrát, kde R je COOR-j,, Χχ je fenylen nebo thiofendiyl, X2 je jednoduchá vazba, -N=N~, -CH-CH-, -CONH-, -NHCO- nebo ethinylen a Xg je fenyl, thiazolinylidenmethyl, thiazolidinylidenmethyl nebo thienyl a A, B, Rj, Rg, R7 a Rg maj í význam uvedený shora.
10. Bicyklická sloučenina obecného vzorce Ib (Ib) kde
A, B, R, X3, X2 a X3 mají význam definovaný shora nebo její súl nebo hydrát, s tím, že nejsou zahrnuty ty sloučeniny, kde Xj a X2 znamenají jednoduchou vazbu a Xg je fenyl a kde X^ je jednoduchá vazba a X2 je -O- a Xg je benzyl.
235
11. Bicyklická sloučenina podle nároku 10, její sůl nebo hydrát, kde a A, B, R, X-p X2 a X3 mají význam uvedený shora.
12. Bicyklická sloučenina podle nároku 11, její sůl nebo hydrát, kde R znamená COOR-p kde R-^ má význam uvedený shora.
13. Sloučenina podle nároku 11, její sůl nebo hydrát, kde X·^ je fenylen nebo thiofendiyl, X2 je jednoduchá vazba, -N=N-, -CH=CH-, ethinylen, -0-, -S-, -C0-, -CON(R55)-, kde R55 má význam definovaný shora, -N (R51) CO-, kde R51 má význam definovaný shora a X3 je fenyl nebo thienyl.
14. Bicyklická sloučenina podle nároku 10, její sůl nebo hydrát, kde
236 a A, B, R, X-p X2, X3 a Z mají význam uvedený shora.
15. Bicyklická sloučenina podle nároku 14, její sůl nebo hydrát, kde B znamená vodík, obě Xj a X2 znamenají jednoduchou vazbu, X3 je thienyl, thiazolyl, thiadiazolyl, isothiazolyl, pyrrolyl, pyridyl, benzofuryl, benzimidazolyl, benzothienyl, dibenzofuryl, dibenzothienyl, chinolyl nebo indolyl.
16. Bicyklická sloučenina podle nároku 15, její sůl nebo hydrát, kde je fenylen, thiofendiyl, indoldiyl nebo oxazoldiyl, X2 je jednoduchá vazba, -N=N~, -CH=CH-, ethinylen, -S- nebo -O- a X3 je aryl nebo heterocyklická skupina.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15457595 | 1995-06-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
CZ401397A3 true CZ401397A3 (cs) | 1998-04-15 |
CZ285870B6 CZ285870B6 (cs) | 1999-11-17 |
Family
ID=15587229
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CZ974013A CZ285870B6 (cs) | 1995-06-21 | 1996-06-19 | Bicyklické aminoderiváty a antagonist PGD2, který je obsahuje |
Country Status (25)
Country | Link |
---|---|
US (3) | US6172113B1 (cs) |
EP (1) | EP0837052B1 (cs) |
JP (1) | JP3195361B2 (cs) |
KR (1) | KR100428601B1 (cs) |
CN (1) | CN1134411C (cs) |
AT (1) | ATE337294T1 (cs) |
AU (1) | AU714312B2 (cs) |
BR (1) | BR9608498B1 (cs) |
CA (1) | CA2225250C (cs) |
CZ (1) | CZ285870B6 (cs) |
DE (1) | DE69636478T2 (cs) |
DK (1) | DK0837052T3 (cs) |
EA (1) | EA000987B1 (cs) |
ES (1) | ES2270438T3 (cs) |
HU (1) | HUP9802678A3 (cs) |
IL (1) | IL122332A0 (cs) |
IS (1) | IS2359B (cs) |
MX (1) | MX9710256A (cs) |
NO (1) | NO975994L (cs) |
NZ (1) | NZ310559A (cs) |
PL (1) | PL185107B1 (cs) |
PT (1) | PT837052E (cs) |
TR (1) | TR199701667T2 (cs) |
TW (1) | TW513422B (cs) |
WO (1) | WO1997000853A1 (cs) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ297324B6 (cs) * | 1996-12-13 | 2006-11-15 | Shionogi & Co., Ltd. | Benzothiofenkarboxamidové deriváty a antagonisty PGD2, které je obsahují |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU5409698A (en) * | 1996-12-12 | 1998-07-03 | Shionogi & Co., Ltd. | Fused heterocyclic benzenecarboxylic acid amide derivatives and pgd2 antagonists containing the same |
WO1998049171A1 (fr) * | 1997-04-28 | 1998-11-05 | Nitto Denko Corporation | Monomere optiquement actif, polymere cristallin liquide et element optique |
WO1999015502A1 (fr) | 1997-09-19 | 1999-04-01 | Shionogi & Co., Ltd. | Composes ayant un squelette [2.2.1]bicyclo |
US6320060B1 (en) * | 1998-03-31 | 2001-11-20 | Shionogi & Co., Ltd. | Process for producing 5-hydroxybenzo[b] thiophene-3-carboxylic acid derivatives |
US6506789B2 (en) * | 1998-06-03 | 2003-01-14 | Shionogi & Co., Ltd. | Methods for the treatment of itching comprising administering PGD2 receptor antagonist |
ATE295183T1 (de) * | 1998-06-03 | 2005-05-15 | Shionogi & Co | Mittel zur linderung von juckreiz, enthaltend pgd2- antagonisten |
AU1179000A (en) * | 1998-11-19 | 2000-06-13 | Shionogi & Co., Ltd. | Preventives and/or remedies for central nervous system diseases containing compounds having TXA2 receptor antagonism and/or TXA2 synthase inhibitory effect |
WO2000053573A1 (fr) * | 1999-03-10 | 2000-09-14 | Shionogi & Co., Ltd. | Compositions medicinales renfermant des composes a squelette [2.2.1] et [3.1.1] bicycliques possedant des proprietes antagonistes vis-a-vis des recepteurs de pgd2/txa¿2? |
EP1207155A4 (en) * | 1999-07-26 | 2005-01-12 | Shionogi & Co | DRUG COMPOSITIONS HAVING AGONIST THROMBOPOIETINE ACTIVITY |
AU6180600A (en) * | 1999-07-29 | 2001-02-19 | Ono Pharmaceutical Co. Ltd. | Sulfonamide derivatives and remedies for allodynia |
MXPA02004985A (es) | 1999-11-26 | 2003-10-14 | Shionogi & Co | Antagonistas del neuropeptido y, y5. |
RU2259998C2 (ru) | 2000-03-09 | 2005-09-10 | Оно Фармасьютикал Ко., Лтд. | Производные индола, способ их получения и их применение |
AU2001240861B2 (en) * | 2000-03-20 | 2006-03-30 | Merck Frosst Canada Ltd | Sulphonamido-substituted bridged bicycloalkyl derivatives |
DE60115411D1 (de) * | 2000-04-12 | 2006-01-05 | Merck Frosst Canada & Co Kirkl | Verfahren und zusammensetzungen zur behandlung von allergischen zuständen mit pgd2 rezeptor antagonisten |
JPWO2001094309A1 (ja) * | 2000-06-02 | 2004-02-05 | 塩野義製薬株式会社 | Pgd2/txa2両受容体拮抗性医薬組成物 |
US6410583B1 (en) * | 2000-07-25 | 2002-06-25 | Merck Frosst Canada & Co. | Cyclopentanoindoles, compositions containing such compounds and methods of treatment |
AU2001278771A1 (en) * | 2000-08-22 | 2002-03-04 | Ono Pharmaceutical Co. Ltd. | Carboxylic acid derivatives, process for producing the same and drugs containingthe same as the active ingredient |
WO2002020462A1 (fr) * | 2000-09-01 | 2002-03-14 | Ono Pharmaceutical Co., Ltd. | Derives d'acide benzoique et medicaments possedant ces derniers comme principe actif |
US7273883B2 (en) | 2000-09-14 | 2007-09-25 | Allergan, Inc. | Prostaglandin EP4 antagonist |
JP4017978B2 (ja) * | 2000-10-17 | 2007-12-05 | 塩野義製薬株式会社 | Pgd2アンタゴニストの製造方法 |
US6933317B2 (en) * | 2000-11-01 | 2005-08-23 | Shionogi & Co. Ltd. | PGD2 receptor antagonistic pharmaceutical compositions |
DE60234812D1 (de) | 2001-01-29 | 2010-02-04 | Shionogi & Co | Arzneipräparat, das als wirkstoff 5-methyl-1-phenyl-2-(1h)-pyridon enthält |
US20030104455A1 (en) * | 2001-11-07 | 2003-06-05 | Millennium Pharmaceuticals, Inc. | Methods and compositions for treating urological disorders using 313, 333, 5464, 18817 or 33524 |
AR038136A1 (es) | 2002-01-24 | 2004-12-29 | Merck Frosst Canada Inc | Cicloalcanindoles con sustitucion con fluor composiciones que contienen estos compuestos y metodos de tratamiento |
WO2004039807A1 (en) | 2002-10-30 | 2004-05-13 | Merck Frosst Canada & Co. | Pyridopyrrolizine and pyridoindolizine derivatives |
KR101197482B1 (ko) | 2004-03-05 | 2012-11-09 | 닛산 가가쿠 고교 가부시키 가이샤 | 이속사졸린 치환 벤즈아미드 화합물 및 유해생물 방제제 |
DK1725553T3 (da) | 2004-03-11 | 2008-08-18 | Actelion Pharmaceuticals Ltd | Tetrahydropyridoindolderivater |
WO2006068162A1 (ja) * | 2004-12-24 | 2006-06-29 | Shionogi & Co., Ltd. | 慢性閉塞性肺疾患の治療剤 |
BRPI0610035A2 (pt) * | 2005-04-21 | 2010-05-18 | Serono Lab | sulfonamidas de pirazina 2,3 substituìdas |
WO2008156573A1 (en) * | 2007-06-12 | 2008-12-24 | Provid Pharmaceuticals, Inc. | Kinase inhibitors, compositions thereof, and methods of use therewith |
US8324385B2 (en) * | 2008-10-30 | 2012-12-04 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
MX2011009423A (es) | 2009-03-09 | 2011-09-28 | Taiho Pharmaceutical Co Ltd | Compuesto de piperazina capaz de inhibir prostaglandina d sintasa. |
JP5731538B2 (ja) | 2009-12-23 | 2015-06-10 | アイアンウッド ファーマシューティカルズ インコーポレイテッド | Crth2モジュレーター |
US20130178475A1 (en) | 2010-03-17 | 2013-07-11 | Ironwood Pharmaceuticals, Inc. | sGC STIMULATORS |
DK2588465T3 (en) | 2010-06-30 | 2017-05-01 | Ironwood Pharmaceuticals Inc | SGC stimulators |
US20130216552A1 (en) | 2010-07-12 | 2013-08-22 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
WO2012009134A1 (en) | 2010-07-12 | 2012-01-19 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
CN107266433A (zh) | 2010-11-09 | 2017-10-20 | 铁木医药有限公司 | sGC刺激剂 |
EP2709609B1 (en) | 2011-05-17 | 2017-10-04 | Shionogi & Co., Ltd. | Heterocyclic compounds |
CA2861804C (en) | 2011-12-27 | 2021-10-26 | Ironwood Pharmaceuticals, Inc. | 2-benzyl,3(pyrimidin-2-yl)substituted pyrazoles useful as sgc stimulators |
WO2014047111A1 (en) | 2012-09-18 | 2014-03-27 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
CA2885645A1 (en) | 2012-09-19 | 2014-03-27 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
CN109369635B (zh) | 2013-03-15 | 2023-06-30 | 赛克里翁治疗有限公司 | 化合物或其药学上可接受的盐及其应用和药物组合物 |
US20160311826A1 (en) | 2013-12-11 | 2016-10-27 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
WO2015106268A1 (en) | 2014-01-13 | 2015-07-16 | Ironwood Pharmaceuticals, Inc. | USE OF sGC STIMULATORS FOR THE TREATMENT OF NEUROMUSCULAR DISORDERS |
EP3194386A2 (en) | 2014-09-17 | 2017-07-26 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
US20170298055A1 (en) | 2014-09-17 | 2017-10-19 | Ironwood Pharmaceuticals, Inc. | sGC STIMULATORS |
US20170291889A1 (en) | 2014-09-17 | 2017-10-12 | Ironwood Pharmaceuticals, Inc. | Pyrazole derivatives as sgc stimulators |
CA2937365C (en) | 2016-03-29 | 2018-09-18 | F. Hoffmann-La Roche Ag | Granulate formulation of 5-methyl-1-phenyl-2-(1h)-pyridone and method of making the same |
US10889577B2 (en) | 2016-07-07 | 2021-01-12 | Cyclerion Therapeutics, Inc. | Solid forms of an sGC stimulator |
CA3029374A1 (en) | 2016-07-07 | 2018-01-11 | Ironwood Pharmaceuticals, Inc. | Phosphorus prodrugs of sgc stimulators |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4837234A (en) | 1981-12-23 | 1989-06-06 | National Research Development Corporation | Prostaglandins |
DE3280020D1 (en) | 1981-12-23 | 1989-12-21 | Nat Res Dev | Prostaglandins |
US4526901A (en) * | 1984-01-26 | 1985-07-02 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted oxamide prostaglandin analogs and their use in treating thrombolytic disease |
JPS6149A (ja) | 1984-06-12 | 1986-01-06 | Ono Pharmaceut Co Ltd | 新規な13―アザ―14―オキソ―TxA2類似化合物およびそれらを有効成分として含有するトロンボキサン起因疾患治療剤 |
CA1278577C (en) * | 1985-11-18 | 1991-01-02 | Tatsuo Tsuri | Bicyclic sulfonamide derivatives |
CA1294974C (en) | 1987-05-08 | 1992-01-28 | Sanji Hagishita | Bicyclic sulfonamide derivatives and process therefor |
EP0312906A3 (en) * | 1987-10-23 | 1990-09-05 | Ono Pharmaceutical Co., Ltd. | Novel sulfonamide derivatives |
JP2565746B2 (ja) * | 1987-10-23 | 1996-12-18 | 小野薬品工業株式会社 | 新規な炭素環系スルホンアミド誘導体 |
JPH0262546A (ja) | 1988-08-30 | 1990-03-02 | Asahi Chem Ind Co Ltd | 改良された光学用感光性樹脂組成物 |
CA2113787A1 (en) * | 1993-01-29 | 1994-07-30 | Nobuyuki Hamanaka | Carbocyclic sulfonamides |
-
1996
- 1996-06-19 EP EP96918841A patent/EP0837052B1/en not_active Expired - Lifetime
- 1996-06-19 TW TW085107425A patent/TW513422B/zh not_active IP Right Cessation
- 1996-06-19 AU AU61370/96A patent/AU714312B2/en not_active Ceased
- 1996-06-19 CZ CZ974013A patent/CZ285870B6/cs not_active IP Right Cessation
- 1996-06-19 AT AT96918841T patent/ATE337294T1/de not_active IP Right Cessation
- 1996-06-19 WO PCT/JP1996/001685 patent/WO1997000853A1/ja active IP Right Grant
- 1996-06-19 PL PL96324115A patent/PL185107B1/pl not_active IP Right Cessation
- 1996-06-19 US US08/973,983 patent/US6172113B1/en not_active Expired - Fee Related
- 1996-06-19 DE DE69636478T patent/DE69636478T2/de not_active Expired - Fee Related
- 1996-06-19 PT PT96918841T patent/PT837052E/pt unknown
- 1996-06-19 MX MX9710256A patent/MX9710256A/es not_active IP Right Cessation
- 1996-06-19 KR KR1019970709573A patent/KR100428601B1/ko not_active IP Right Cessation
- 1996-06-19 TR TR97/01667T patent/TR199701667T2/xx unknown
- 1996-06-19 HU HU9802678A patent/HUP9802678A3/hu unknown
- 1996-06-19 DK DK96918841T patent/DK0837052T3/da active
- 1996-06-19 NZ NZ310559A patent/NZ310559A/xx unknown
- 1996-06-19 CA CA002225250A patent/CA2225250C/en not_active Expired - Fee Related
- 1996-06-19 BR BRPI9608498-7A patent/BR9608498B1/pt not_active IP Right Cessation
- 1996-06-19 ES ES96918841T patent/ES2270438T3/es not_active Expired - Lifetime
- 1996-06-19 CN CNB961963263A patent/CN1134411C/zh not_active Expired - Fee Related
- 1996-06-19 EA EA199800074A patent/EA000987B1/ru not_active IP Right Cessation
- 1996-06-19 JP JP50372497A patent/JP3195361B2/ja not_active Expired - Fee Related
- 1996-06-19 IL IL12233296A patent/IL122332A0/xx not_active IP Right Cessation
-
1997
- 1997-11-28 IS IS4623A patent/IS2359B/is unknown
- 1997-12-19 NO NO975994A patent/NO975994L/no not_active Application Discontinuation
-
2000
- 2000-02-18 US US09/506,608 patent/US6384075B1/en not_active Expired - Fee Related
- 2000-02-18 US US09/506,606 patent/US6498190B1/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ297324B6 (cs) * | 1996-12-13 | 2006-11-15 | Shionogi & Co., Ltd. | Benzothiofenkarboxamidové deriváty a antagonisty PGD2, které je obsahují |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CZ401397A3 (cs) | Bicyklické aminoderiváty a antagonist PGD2, který je obsahuje | |
RU2128644C1 (ru) | Производные антраниловой кислоты или их фармакологически приемлемые соли, промежуточные продукты для их получения и лекарственный препарат на их основе | |
JP5408434B2 (ja) | アミド化合物 | |
EP2489350B1 (en) | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors | |
JP4320089B2 (ja) | フェニルスルファメート誘導体 | |
MXPA05006701A (es) | Moduladores de asma y de inflacion alergica. | |
GB2216517A (en) | 1-(3-aryl-prop-2-enyl)-4-tricyclyl-piperazines | |
JPWO2008123207A1 (ja) | オルニチン誘導体 | |
WO2019011285A1 (zh) | 四氢萘并[1,2-b]呋喃-2(3H)-酮衍生物及其制备与在制药中的应用 | |
EP1016660B1 (en) | Compounds having 2.2.1]bicyclo skeleton | |
JPS609716B2 (ja) | 1,2―ベンズインチアゾリン―3―オン類、それらの製造法および医薬としての使用 | |
CA2081262A1 (en) | Acetylene compounds | |
US20020169157A1 (en) | Selective protein tyrosine phosphatatase inhibitors | |
JP3701878B2 (ja) | ビシクロ環系アミノ誘導体およびそれを含有するpgd2拮抗剤 | |
JP2001525398A (ja) | 選択的β3アドレナリン作動性アゴニスト | |
FI77246C (fi) | Foerfarande foer framstaellning av antiallergiska 4h-furo/3,2-b/indoler. | |
JPS61268680A (ja) | 新規なイソオキサゾール誘導体 | |
US4831055A (en) | Benzoic acid derivatives | |
CN113620890B (en) | Benzoquinoxalinone compound and synthesis method and application thereof | |
PT643045E (pt) | Derivados de quinoleina como antagonistas de leucotrienos | |
US5312825A (en) | S-(2-thenoyl)-thiolactic acid derivative having pharmacological activity | |
CN113620890A (zh) | 苯并喹喔啉酮化合物及其合成方法和用途 | |
JPS6391354A (ja) | 新規なカルボン酸誘導体 | |
JPS63159359A (ja) | 安息香酸誘導体 | |
PT92291A (pt) | Processo para a producao de derivados substituidos de alilamina e de composicoes farmaceuticas que os contem |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
IF00 | In force as of 2000-06-30 in czech republic | ||
MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20090619 |