NO750278L - - Google Patents

Info

Publication number: NO750278L
Authority: NO; Norway
Prior art keywords: diphenylthiazole; reacted; formula; hydrochloride; production
Prior art date: 1974-01-31

Application number

NO750278A

Other languages

English (en)

Norwegian (no)

Inventor

E Marchetti

Original Assignee

Serono Lab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-01-31

Filing date

1975-01-30

Publication date

1975-08-25

1975-01-30 Application filed by Serono Lab filed Critical Serono Lab

1975-08-25 Publication of NO750278L publication Critical patent/NO750278L/no

Links

150000001875 compounds Chemical class 0.000 claims description 34
238000000034 method Methods 0.000 claims description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
-1 2-substituted 4,5-diphenylthiazole Chemical class 0.000 claims description 20
PULFWRQSLZZQGJ-UHFFFAOYSA-N 2-chloro-4,5-diphenyl-1,3-thiazole Chemical compound S1C(Cl)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PULFWRQSLZZQGJ-UHFFFAOYSA-N 0.000 claims description 18
238000004519 manufacturing process Methods 0.000 claims description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
BGTVICKPWACXLR-UHFFFAOYSA-N 4,5-diphenyl-1,3-thiazole Chemical compound S1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 BGTVICKPWACXLR-UHFFFAOYSA-N 0.000 claims description 3
125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
GAAGQBXBMOGSPR-UHFFFAOYSA-N n-methyl-4,5-diphenyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GAAGQBXBMOGSPR-UHFFFAOYSA-N 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical class C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 claims description 2
IXXVSAPHIXSNHH-UHFFFAOYSA-N 4,5-diphenyl-2-pyrrolidin-1-yl-1,3-thiazole Chemical compound C1CCCN1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 IXXVSAPHIXSNHH-UHFFFAOYSA-N 0.000 claims description 2
JJPLCRUFHNUBHR-UHFFFAOYSA-N 4,5-diphenyl-n-propan-2-yl-1,3-thiazol-2-amine Chemical compound S1C(NC(C)C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JJPLCRUFHNUBHR-UHFFFAOYSA-N 0.000 claims description 2
XUSCWHCNMRYDGV-UHFFFAOYSA-N 4-(4,5-diphenyl-1,3-thiazol-2-yl)morpholine Chemical compound C1COCCN1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 XUSCWHCNMRYDGV-UHFFFAOYSA-N 0.000 claims description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
239000012458 free base Substances 0.000 claims 5
125000002252 acyl group Chemical group 0.000 claims 2
MIECVJDZXBUVSN-UHFFFAOYSA-N 2,4-diphenyl-1,3-thiazole Chemical compound C=1SC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 MIECVJDZXBUVSN-UHFFFAOYSA-N 0.000 claims 1
KQVYPDUPFZBISW-UHFFFAOYSA-N 4,5-diphenyl-2-(piperidin-1-ylmethyl)-1,3-thiazole Chemical compound N1(CCCCC1)CC=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 KQVYPDUPFZBISW-UHFFFAOYSA-N 0.000 claims 1
RJBSUZMZEIBOBU-UHFFFAOYSA-N 4,5-diphenyl-2-(pyrrolidin-1-ylmethyl)-1,3-thiazole Chemical compound N1(CCCC1)CC=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 RJBSUZMZEIBOBU-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
238000004458 analytical method Methods 0.000 description 14
239000000203 mixture Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000003208 petroleum Substances 0.000 description 10
238000001816 cooling Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000007363 ring formation reaction Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
241000700159 Rattus Species 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
SHSWPTQNISABOU-UHFFFAOYSA-N 2-(chloromethyl)-4,5-diphenyl-1,3-thiazole Chemical compound S1C(CCl)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 SHSWPTQNISABOU-UHFFFAOYSA-N 0.000 description 3
AGOQHOLPBJSUFA-UHFFFAOYSA-N 2-chloro-n-(2-oxo-1,2-diphenylethyl)acetamide Chemical compound C=1C=CC=CC=1C(NC(=O)CCl)C(=O)C1=CC=CC=C1 AGOQHOLPBJSUFA-UHFFFAOYSA-N 0.000 description 3
102000008186 Collagen Human genes 0.000 description 3
108010035532 Collagen Proteins 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
238000004220 aggregation Methods 0.000 description 3
230000002776 aggregation Effects 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229920001436 collagen Polymers 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000243 solution Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
BJWMECHWZAAHRV-UHFFFAOYSA-N Cl.O1CCN(CC1)CC=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound Cl.O1CCN(CC1)CC=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 BJWMECHWZAAHRV-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
230000004931 aggregating effect Effects 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
230000002744 anti-aggregatory effect Effects 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000000871 hypocholesterolemic effect Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
YFMYADHUNDCRKI-UHFFFAOYSA-N 2-bromo-4,5-diphenyl-1,3-thiazole Chemical compound S1C(Br)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 YFMYADHUNDCRKI-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
VPJJDOXTJPFLHM-UHFFFAOYSA-N 4,5-diphenyl-2-(pyrrolidin-1-ylmethyl)-1,3-thiazole hydrochloride Chemical compound Cl.N1(CCCC1)CC=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 VPJJDOXTJPFLHM-UHFFFAOYSA-N 0.000 description 1
SVNXMNUJNYYERN-UHFFFAOYSA-N 4,5-diphenyl-3h-1,3-thiazol-2-one Chemical compound S1C(=O)NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 SVNXMNUJNYYERN-UHFFFAOYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
239000002126 C01EB10 - Adenosine Substances 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
RTISZPAJVMJCJM-UHFFFAOYSA-N Cl.C(C)(C)NCC=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound Cl.C(C)(C)NCC=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 RTISZPAJVMJCJM-UHFFFAOYSA-N 0.000 description 1
RXGFEHPMAKKCTA-UHFFFAOYSA-N Cl.N1(CCCCC1)CC=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound Cl.N1(CCCCC1)CC=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 RXGFEHPMAKKCTA-UHFFFAOYSA-N 0.000 description 1
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
208000032843 Hemorrhage Diseases 0.000 description 1
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 1
ISCMGFNYVGNDJY-UHFFFAOYSA-N N,N-diethyl-4,5-diphenyl-1,3-thiazol-2-amine Chemical compound C(C)N(C=1SC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1)CC ISCMGFNYVGNDJY-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229960005305 adenosine Drugs 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
RMKNCYHVESPYFD-UHFFFAOYSA-N decan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCC[NH3+] RMKNCYHVESPYFD-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
230000000260 hypercholesteremic effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
QNWYADJKZRRWKT-UHFFFAOYSA-N potassium;sulfo cyanate Chemical compound [K].OS(=O)(=O)OC#N QNWYADJKZRRWKT-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 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
239000007787 solid Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1

Classifications

- 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen 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
- 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO750278A 1974-01-31 1975-01-30 NO750278L (es)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH137774A CH587836A5 (es)	1974-01-31	1974-01-31

Publications (1)

Publication Number	Publication Date
NO750278L true NO750278L (es)	1975-08-25

Family

ID=4208998

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO750278A NO750278L (es)	1974-01-31	1975-01-30

Country Status (15)

Country	Link
JP (1)	JPS50121269A (es)
AT (1)	AT339898B (es)
BE (1)	BE825097A (es)
CA (1)	CA1036600A (es)
CH (1)	CH587836A5 (es)
DE (1)	DE2503436A1 (es)
DK (1)	DK33175A (es)
ES (1)	ES434151A1 (es)
FR (1)	FR2259603B1 (es)
GB (1)	GB1490771A (es)
IL (1)	IL46476A (es)
NL (1)	NL7501086A (es)
NO (1)	NO750278L (es)
SE (1)	SE7501010L (es)
ZA (1)	ZA75494B (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4168315A (en) *	1977-09-28	1979-09-18	The Upjohn Company	Dianisyl thiazole compound, compositions and method of antithrombotic treatment
JPH0753666B2 (ja) *	1987-09-14	1995-06-07	久光製薬株式会社	置換ジフェニルチアゾール誘導体からなる抗炎症剤
CA2012716A1 (en) *	1989-03-22	1990-09-22	Akito Tanaka	Thiazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same
ATE194338T1 (de) *	1991-03-07	2000-07-15	Hisamitsu Pharmaceutical Co	Diphenylthiazolderivate mit antiinflammatorischer aktivität
CA2515119A1 (en)	2003-02-07	2004-08-19	Daiichi Pharmaceutical Co., Ltd.	Pyrazole derivative
WO2009041447A1 (ja)	2007-09-28	2009-04-02	Takeda Pharmaceutical Company Limited	５員複素環化合物

1974
- 1974-01-31 CH CH137774A patent/CH587836A5/xx not_active IP Right Cessation
1975
- 1975-01-21 IL IL46476A patent/IL46476A/xx unknown
- 1975-01-23 ZA ZA00750494A patent/ZA75494B/xx unknown
- 1975-01-24 GB GB3224/75A patent/GB1490771A/en not_active Expired
- 1975-01-24 AT AT55975A patent/AT339898B/de not_active IP Right Cessation
- 1975-01-25 ES ES434151A patent/ES434151A1/es not_active Expired
- 1975-01-27 CA CA218,709A patent/CA1036600A/en not_active Expired
- 1975-01-28 DE DE19752503436 patent/DE2503436A1/de not_active Ceased
- 1975-01-30 DK DK33175*#A patent/DK33175A/da not_active Application Discontinuation
- 1975-01-30 NL NL7501086A patent/NL7501086A/xx not_active Application Discontinuation
- 1975-01-30 NO NO750278A patent/NO750278L/no unknown
- 1975-01-30 SE SE7501010A patent/SE7501010L/xx unknown
- 1975-01-31 BE BE152985A patent/BE825097A/xx not_active IP Right Cessation
- 1975-01-31 FR FR7503048A patent/FR2259603B1/fr not_active Expired
- 1975-01-31 JP JP50012645A patent/JPS50121269A/ja active Pending

Also Published As

Publication number	Publication date
IL46476A0 (en)	1975-04-25
DE2503436A1 (de)	1975-08-07
ES434151A1 (es)	1976-12-01
ATA55975A (de)	1977-03-15
NL7501086A (nl)	1975-08-04
SE7501010L (es)	1975-08-01
GB1490771A (en)	1977-11-02
CA1036600A (en)	1978-08-15
BE825097A (fr)	1975-07-31
FR2259603A1 (es)	1975-08-29
DK33175A (es)	1975-09-29
AU7747875A (en)	1976-07-22
FR2259603B1 (es)	1978-07-21
IL46476A (en)	1978-12-17
AT339898B (de)	1977-11-10
JPS50121269A (es)	1975-09-23
ZA75494B (en)	1976-01-28
CH587836A5 (es)	1977-05-13

Publication	Publication Date	Title
US3853915A (en)	1974-12-10	9-or 10-halo-4h-benzo{8 4,5{9 cyclo-hepta{8 1,2-b{9 thiophen-4-ones
US3014911A (en)	1961-12-26	Derivatives of dibenzo[a, e]cycloheptatriene
NO152048B (no)	1985-04-15	Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 5h-2,3-benzodiazepinderivater
US3072653A (en)	1963-01-08	5-amino derivatives of 4-thiazolidinones and process therefor
US4559349A (en)	1985-12-17	Carboxamides
US3830803A (en)	1974-08-20	5-loweralkyl-1-phenyl-1,3,4,6-tetrahydro-5h-benz(f)-2,5-oxazocines and 4-ones
US2734904A (en)	1956-02-14	Xcxnhxc-nh
US3120540A (en)	1964-02-04	Bis (polymethyl)-4-piperidinol alkanoates
EP0040860B1 (en)	1984-03-14	Dibenzoxazepine derivative, process for preparing the same and pharmaceutical composition comprising the same
JPH072770A (ja)	1995-01-06	新規な置換インドール類、その製造法及びそのインドール類を含有する製剤組成物
US4213985A (en)	1980-07-22	Novel 5,11-dihydro-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-ones
US3123618A (en)	1964-03-03	Io-dihydroanthkacene-z
NO750278L (es)	1975-08-25
US3227716A (en)	1966-01-04	Therapeutically-active dibenzocycloheptane derivatives
EP0011447B1 (en)	1983-01-05	Blood platelet aggregation inhibitory 1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid derivatives and salts thereof; pharmaceutical compositions thereof; and analogy processes for the manufacture thereof
US4001228A (en)	1977-01-04	2-thiol-4,5-diphenyloxazole s-derivatives
FR2522000A1 (fr)	1983-08-26	Nouvelles thiopyrannopyrimidines, utiles notamment comme agents hypoglycemiants, et leur fabrication
NO128773B (es)	1974-01-07
US2652399A (en)	1953-09-15	Tertiary-aminoalkyl derivatives of coumarilic acids and their preparation
NO128025B (es)	1973-09-17
JPH0131502B2 (es)	1989-06-26
NO152558B (no)	1985-07-08	Analogifremgangsmaate for fremstilling av fysiologisk aktive 1-benzyl-1,2,3,6-tetra-hydropyridinderivater
DK159110B (da)	1990-09-03	4h-benzo(4,5)cyclohepta(1,2-b)thiophenderivater, fremgangsmaade til fremstilling deraf samt farmaceutiske praeparater indeholdende derivaterne
US2694069A (en)	1954-11-09	Basic esters of hydroxy-and alkoxy-substituted phenyloxoalkenoic acids and their salts
US2749346A (en)	1956-06-05	Tetrahydropyridine compounds