IL91377A - Derivatives of botinylamine glycolate - Google Patents

Derivatives of botinylamine glycolate

Info

Publication number: IL91377A
Authority: IL; Israel
Prior art keywords: calcd; butynyl; cyclohexyl; elemental analysis; found
Prior art date: 1988-09-14

Application number

IL9137789A

Other languages

English (en)

Hebrew (he)

Other versions

IL91377A0 (en

Original Assignee

Nippon Shinyaku Co Ltd

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.)

1988-09-14

Filing date

1989-08-22

Publication date

1996-09-12

1989-08-22 Application filed by Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd

1990-04-29 Publication of IL91377A0 publication Critical patent/IL91377A0/xx

1996-09-12 Publication of IL91377A publication Critical patent/IL91377A/en

Links

AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 64
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
-1 methoxy, ethoxy Chemical group 0.000 description 58
238000000921 elemental analysis Methods 0.000 description 43
239000000243 solution Substances 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 21
238000001816 cooling Methods 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 16
229960005434 oxybutynin Drugs 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
238000012360 testing method Methods 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
230000001078 anti-cholinergic effect Effects 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
239000002904 solvent Substances 0.000 description 12
238000000034 method Methods 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
229940079593 drug Drugs 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000008602 contraction Effects 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000003756 stirring Methods 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
230000003042 antagnostic effect Effects 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
239000000499 gel Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
239000007818 Grignard reagent Substances 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
241000283973 Oryctolagus cuniculus Species 0.000 description 5
229930040373 Paraformaldehyde Natural products 0.000 description 5
241000700159 Rattus Species 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
150000004795 grignard reagents Chemical class 0.000 description 5
210000003205 muscle Anatomy 0.000 description 5
229920002866 paraformaldehyde Polymers 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
206010036018 Pollakiuria Diseases 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 4
229960004484 carbachol Drugs 0.000 description 4
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
229940045803 cuprous chloride Drugs 0.000 description 4
229910001873 dinitrogen Inorganic materials 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
238000006683 Mannich reaction Methods 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
239000011575 calcium Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000005457 ice water Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000012453 sprague-dawley rat model Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
206010020853 Hypertonic bladder Diseases 0.000 description 2
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 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
206010046543 Urinary incontinence Diseases 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
230000002213 calciumantagonistic effect Effects 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
150000002642 lithium compounds Chemical class 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000001020 rhythmical effect Effects 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
235000001508 sulfur Nutrition 0.000 description 2
229960005349 sulfur Drugs 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
GZLPSKJLMBWYQN-UHFFFAOYSA-N 2-benzyl-1-[(4-tert-butylphenyl)methyl]benzimidazole Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C2=CC=CC=C2N=C1CC1=CC=CC=C1 GZLPSKJLMBWYQN-UHFFFAOYSA-N 0.000 description 1
AKBJJHWIZAPTJW-UHFFFAOYSA-N 2-hydroxyacetic acid;hydrochloride Chemical compound Cl.OCC(O)=O AKBJJHWIZAPTJW-UHFFFAOYSA-N 0.000 description 1
OJFZLBZJMQCWFP-UHFFFAOYSA-N 4-(piperidin-1-ylmethyl)isoindole-1,3-dione Chemical compound O=C1NC(=O)C2=C1C=CC=C2CN1CCCCC1 OJFZLBZJMQCWFP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
DBAMUTGXJAWDEA-UHFFFAOYSA-N Butynol Chemical compound CCC#CO DBAMUTGXJAWDEA-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
MDZNDSNSMSDIBM-UHFFFAOYSA-N Cl.C=1C=CC=CC=1C(O)(C(=O)OC(C)(C)C#CCN(CC)CC)C1=CC=CC=C1 Chemical compound Cl.C=1C=CC=CC=1C(O)(C(=O)OC(C)(C)C#CCN(CC)CC)C1=CC=CC=C1 MDZNDSNSMSDIBM-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
208000008967 Enuresis Diseases 0.000 description 1
206010021639 Incontinence Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000000693 Neurogenic Urinary Bladder Diseases 0.000 description 1
206010029279 Neurogenic bladder Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
201000003146 cystitis Diseases 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229960000855 flavoxate Drugs 0.000 description 1
SPIUTQOUKAMGCX-UHFFFAOYSA-N flavoxate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCN1CCCCC1 SPIUTQOUKAMGCX-UHFFFAOYSA-N 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
NXYVAWJECZFWOE-UHFFFAOYSA-N n-formyl-n-prop-2-ynylbenzamide Chemical compound C#CCN(C=O)C(=O)C1=CC=CC=C1 NXYVAWJECZFWOE-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
UISARWKNNNHPGI-UHFFFAOYSA-N terodiline Chemical compound C=1C=CC=CC=1C(CC(C)NC(C)(C)C)C1=CC=CC=C1 UISARWKNNNHPGI-UHFFFAOYSA-N 0.000 description 1
229960005383 terodiline Drugs 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
230000035922 thirst Effects 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- 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
- C07D295/08—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 singly bound oxygen or sulfur atoms
- C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/20—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/24—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of 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
- C07C235/02—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
- C07C235/34—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 atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- 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
- C07D295/12—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 singly or doubly bound nitrogen atoms
- C07D295/125—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic 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
- C07D333/24—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring 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
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

IL9137789A 1988-09-14 1989-08-22 Derivatives of botinylamine glycolate IL91377A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP23127288		1988-09-14

Publications (2)

Publication Number	Publication Date
IL91377A0 IL91377A0 (en)	1990-04-29
IL91377A true IL91377A (en)	1996-09-12

Family

ID=16921002

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9137789A IL91377A (en)	1988-09-14	1989-08-22	Derivatives of botinylamine glycolate

Country Status (13)

Country	Link
US (1)	US5036098B1 (de)
EP (1)	EP0359311B1 (de)
KR (1)	KR0154325B1 (de)
CN (1)	CN1038410C (de)
BE (1)	BE1003256A5 (de)
CA (1)	CA1317943C (de)
CH (1)	CH680440A5 (de)
DE (1)	DE68927657T2 (de)
ES (1)	ES2016060A6 (de)
FR (1)	FR2639044B1 (de)
GB (2)	GB8919320D0 (de)
HU (2)	HUT58045A (de)
IL (1)	IL91377A (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5066680A (en) *	1989-02-14	1991-11-19	Fujisawa Pharmaceutical Co., Ltd.	Novel substituted-acetamide compound and a process for the preparation thereof
US5192779A (en) *	1989-02-14	1993-03-09	Fujisawa Pharmaceutical Co., Ltd.	Substituted-acetamide compound and a process for the preparation thereof
US6207852B1 (en) *	1996-07-01	2001-03-27	Bridge Pharma, Inc.	Smooth muscle spasmolytic agents, compositions and methods of use thereof
US6541479B1 (en)	1997-12-02	2003-04-01	Massachusetts College Of Pharmacy	Calcium channel blockers
US6013830A (en) *	1998-03-30	2000-01-11	Sepracor Inc.	Asymmetric grignard synthesis with cyclic 1,2 aminoalcohols
US6140529A (en) *	1998-10-22	2000-10-31	Sepracor Inc.	Synthesis of optically active cyclohexylphenylglycolate esters
ES2315425T3 (es) *	2001-10-26	2009-04-01	PHARMACIA & UPJOHN COMPANY LLC	Compuestos de amonio cuaternario y su uso como agentes antimuscarinicos.
TW200300079A (en) *	2001-11-05	2003-05-16	Upjohn Co	Antimuscarinic aerosol
TW200412945A (en) *	2002-10-25	2004-08-01	Upjohn Co	Quaternary ammonium compounds
US6878730B2 (en) *	2002-10-29	2005-04-12	Pharmacia & Upjohn	Quaternary ammonium compounds
CA2503654A1 (en) *	2002-10-29	2004-05-13	Pharmacia & Upjohn Company Llc	Quinuclidinium derivatives as antimuscarinic agents
US7887431B2 (en) *	2008-05-16	2011-02-15	Taylor Made Golf Company, Inc.	Golf club
US20040242569A1 (en) *	2003-04-15	2004-12-02	Pfizer Inc.	Quatemary ammonium compounds
WO2004091597A2 (en) *	2003-04-15	2004-10-28	Pharmacia & Upjohn Company Llc	Method of treating irritable bowel syndrome (ibs)
WO2011137054A1 (en)	2010-04-30	2011-11-03	Merck Sharp & Dohme Corp.	Novel beta 3 adrenergic receptor agonists

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL122610C (de) *	1959-02-18
NL124473C (de) *	1960-07-26
JPH0755904B2 (ja) *	1986-05-14	1995-06-14	小玉株式会社	膀胱疾患治療剤
US5066680A (en) *	1989-02-14	1991-11-19	Fujisawa Pharmaceutical Co., Ltd.	Novel substituted-acetamide compound and a process for the preparation thereof

1989
- 1989-08-22 IL IL9137789A patent/IL91377A/en not_active IP Right Cessation
- 1989-08-25 GB GB898919320A patent/GB8919320D0/en active Pending
- 1989-08-30 CN CN89106930A patent/CN1038410C/zh not_active Expired - Fee Related
- 1989-09-05 DE DE68927657T patent/DE68927657T2/de not_active Expired - Fee Related
- 1989-09-05 EP EP89202235A patent/EP0359311B1/de not_active Expired - Lifetime
- 1989-09-12 KR KR1019890013217A patent/KR0154325B1/ko not_active IP Right Cessation
- 1989-09-12 ES ES8903097A patent/ES2016060A6/es not_active Expired - Fee Related
- 1989-09-13 GB GB8920766A patent/GB2222828B/en not_active Expired - Fee Related
- 1989-09-13 HU HU894825A patent/HUT58045A/hu unknown
- 1989-09-13 CH CH3344/89A patent/CH680440A5/fr not_active IP Right Cessation
- 1989-09-13 CA CA000611310A patent/CA1317943C/en not_active Expired - Fee Related
- 1989-09-14 US US90/002826A patent/US5036098B1/en not_active Expired - Lifetime
- 1989-09-14 FR FR898912032A patent/FR2639044B1/fr not_active Expired - Fee Related
- 1989-09-14 BE BE8900977A patent/BE1003256A5/fr not_active IP Right Cessation
1995
- 1995-06-07 HU HU95P/P00170P patent/HU211134A9/hu unknown

Also Published As

Publication number	Publication date
US5036098B1 (en)	1993-11-02
FR2639044B1 (fr)	1993-08-06
ES2016060A6 (es)	1990-10-01
EP0359311A3 (de)	1991-07-03
DE68927657T2 (de)	1997-07-03
IL91377A0 (en)	1990-04-29
KR900004728A (ko)	1990-04-12
EP0359311B1 (de)	1997-01-15
GB2222828B (en)	1992-04-29
US5036098A (en)	1991-07-30
BE1003256A5 (fr)	1992-02-11
HUT58045A (en)	1992-01-28
CN1038410C (zh)	1998-05-20
CA1317943C (en)	1993-05-18
CH680440A5 (de)	1992-08-31
DE68927657D1 (de)	1997-02-27
FR2639044A1 (fr)	1990-05-18
GB8920766D0 (en)	1989-10-25
CN1041582A (zh)	1990-04-25
GB8919320D0 (en)	1989-10-11
KR0154325B1 (ko)	1998-12-01
EP0359311A2 (de)	1990-03-21
GB2222828A (en)	1990-03-21
HU211134A9 (en)	1995-10-30

Legal Events

Date	Code	Title
1997-02-18	FF	Patent granted
1997-06-10	KB	Patent renewed
2000-01-31	KB	Patent renewed
2003-10-31	KB	Patent renewed
2008-06-05	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
KR910002892B1 (ko)	1991-05-09	술포늄 화합물의 제조방법
IL91377A (en)	1996-09-12	Derivatives of botinylamine glycolate
AU2006224853B2 (en)	2011-08-18	Trifluoromethylbenzamide derivatives and therapeutic uses thereof
CA2015473C (en)	1998-04-14	Triphenylmethane derivatives
IE58608B1 (en)	1993-10-20	Piperazine derivatives
GB2098988A (en)	1982-12-01	1,2-diamino-cyclobutene-3,4-dione derivatives
KR0171569B1 (ko)	1999-05-01	신규 디아민 화합물 및 이를 함유하는 뇌보호제
US4510139A (en)	1985-04-09	Substituted aminobenzamides and their use as agents which inhibit lipoxygenase activity
IE54896B1 (en)	1990-03-14	Pyrrolacetic amides having antiinflammatory activity
US4935419A (en)	1990-06-19	Novel 1-piperazinecarboxamide derivatives
EP0306827B1 (de)	1991-09-04	Amidverbindungen, Verfahren zu ihrer Herstellung und Zusammensetzung zur Aktivierung gastromotorischer Funktionen
KR19980703476A (ko)	1998-11-05	피롤리딘일 하이드록삼산 화합물 및 그의 제조 방법
CA1167446A (en)	1984-05-15	2-¬4-(diphenylmethylene)-1-piperidinyl\|-acetic acids and their amides
US3632587A (en)	1972-01-04	Piperazino methyl isatinylidine 3 acetates
Rajak et al.	2008	Synthesis and Local Anesthetic Activity of Some Novel N‐[5‐(4‐Substituted) phenyl‐1, 3, 4‐oxadiazol‐2‐yl]‐2‐(Substituted)‐Acetamides
BG63336B1 (bg)	2001-10-31	Нови производни на хидроксамови киселини, фармацевтични състави на тяхна основа и метод за получаването им
US3972994A (en)	1976-08-03	Disubstituted azabicycloalkanes
CA1094070A (en)	1981-01-20	1-phenyl-piperazine derivatives
RU2142453C1 (ru)	1999-12-10	ПРОИЗВОДНЫЕ 1-[ω-(3,4-ДИГИДРО-2-НАФТАЛИНИЛ)АЛКИЛ]ЦИКЛИЧЕСКОГО АМИНА И СОДЕРЖАЩАЯ ИХ ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ
US3857945A (en)	1974-12-31	Pharmaceutical compositions containing piperazine derivatives in the treatment of pain
CA2038417A1 (en)	1991-10-12	Piperidine compounds, method for preparation thereof, and a pharmaceutical composition comprising the same
EP0034752B1 (de)	1983-06-08	Phenoxyalkanderivat und Verfahren zu dessen Herstellung
US3701786A (en)	1972-10-31	Dibenzofuranyl-aminoalcohols
US5837717A (en)	1998-11-17	Hydroxamic acid anesthetic compounds
EP0150073A1 (de)	1985-07-31	3,4-Disubstituierte-1,2,5-Oxadiazole mit Histamin H2-Rezeptor-Antagonisten-Aktivität