KR960700244A - 항 염증성 3-아실-2-옥스인돌-1-카복스아미드의 약물 전구체(prodrugs of antinflammatory 3-acyl-2-oxindole-1-carboxamides) - Google Patents
항 염증성 3-아실-2-옥스인돌-1-카복스아미드의 약물 전구체(prodrugs of antinflammatory 3-acyl-2-oxindole-1-carboxamides)Info
- Publication number
- KR960700244A KR960700244A KR1019950703074A KR19950703074A KR960700244A KR 960700244 A KR960700244 A KR 960700244A KR 1019950703074 A KR1019950703074 A KR 1019950703074A KR 19950703074 A KR19950703074 A KR 19950703074A KR 960700244 A KR960700244 A KR 960700244A
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- Prior art keywords
- alkyl
- compound
- optionally substituted
- cycloalkyl
- phenyl
- Prior art date
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- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract 4
- 229940002612 prodrug Drugs 0.000 title 1
- 239000000651 prodrug Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract 5
- 150000002367 halogens Chemical class 0.000 claims abstract 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- 230000000202 analgesic effect Effects 0.000 claims 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000005414 inactive ingredient Substances 0.000 claims 1
- 150000003951 lactams Chemical group 0.000 claims 1
- 125000000686 lactone group Chemical group 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical group C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 150000003018 phosphorus compounds Chemical group 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 150000003235 pyrrolidines Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- 230000001760 anti-analgesic effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
본 발명은 R10,R11,R12및 R13이 수소, 알킬 또는 할로겐이고, R이 메틸렌옥시알카노일, 메틸렌옥시알케노일 또는 알케노일인 하기 일반식(Ⅰ)의 항염증성 및 진통성 옥스인돌 약물 전구체에 관한 것이다:
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (37)
- 하기 일반식(Ⅰ)의 화합물:
-
- 상기식에서, R은
-
-
- 또는
-
- 이고, x는 0 또는 1이고; A는 C1-C7알킬 또는 C3-C7사이클로알킬로부터 독립적으로 선택된 2개 이하의 치환제에 의해 선택적으로 치환된 C1-C5알킬렌 또는 C2-C6알케닐쇄이거나; 또는 (CH2)nO(CH2)m(여기서, 메틸렌 그룹은 C1-C7알킬 또는 C3-C7사이클로알킬로부터 독립적으로 선택된 2개 이하의 치환체에 의해 선택적으로 치환될 수 있다)이거나; 또는 2개 이하의 C1-C3알킬에 의해 선택적으로 치환된 C3-C7사이클로알킬 또는 사이클로알케닐 그룹이거나; 또는 O,S 또는 NR6결합을 함유하는 4원 내지 7원 헤테로-지환족그룹이거나; 또는 C1-C3알킬, C1-C3알킬옥시, 할로겐 또는 CF3중에서 독립적으로 선택된 2개 이하의 치환체에 의해 선택적으로 치환된 페닐렌 그룹이고; B는 C2-C6알케닐 페닐, 2,3 또는 4-피리딜, 2,3 또는 4-피페리디닐, 2 또는 3-피롤리디닐, -OCH2CO2R1또는 -OCH2CONR2R3이고; R1은 H, C1-C8알킬, C3-C7사이클로알킬, 페닐(C1-C4)알킬, (CH2)p-CO2R2, (CH2)nCONR2R3또는 (CH2)pSi(CH3)2이거나; 또는 R1은 A와 함께, C1-C3알킬 그룹으로 선택적으로 치환된 5,6 또는 7원 락톤고리를 형성할 수 있고, R2및 R3는 독립적으로 H, C1-C7알킬, C3-C7사이클로알킬, 페닐-(C1-C4)알킬이거나; 또는 R2및 R3는 결합된 질소와 함께, 2개 이하의 C1-C3알킬 그룹으로 선택적으로 치환된 피롤리딘, 피페리딘, 모플린 또는 호모피페리딘 그룹을 의미하거나: 또는 R2또는 R3는 A와 함께 2개 이하의 C1-C3알킬그룹으로 선택적으로 치환된 5,6 또는 7원 락탐고리를 형성할 수 있고; R4및 R5는 독립적으로 H, C1-C7알킬, C3-C7사이클로알킬, 페닐-(C1-C4)알킬, (CH2)pCO2R2, (CH2)pCONR2R3, (CH2)pNR7R8, (CH2)pOR6또는 (CH2)pSR6이거나; 또는 R4및 R5는 함께, 2개 이하의 C1-C3알킬 그룹으로 선택적으로 치환된 C3-C7사이클로알킬 고리를 의미하고; R6는 H,C1-C6알킬; (CH)pCOOR2; 2개 이하의 C1-C6알킬 그룹으로 선택적으로 치환된 C3-C7사이클로알킬; C1-C3알킬, C1-C3알킬옥시, 할로겐 또는 CF3중에서 독립적으로 선택된 2개 이하의 치환체로 페닐 고리에서 선택적으로 치환된 페닐-(C1-C4)알킬; COR2;CONR2R3; 또는 C1-C3알킬, C1-C3알킬-옥시, 할로겐 또는 CF3중에서 독립적으로 선택된 2개 이하의 치환체로 선택적으로 치환된 페닐 그룹이거나; 또는 R6는 R4및 결합된 산소와 함께, 2개 이하의 C1-C3알킬 그룹으로 선택적으로 치환된 옥세탄, 테트라하이드로푸란, 테트라하이드로피란 또는 옥세판 고리를 의미하고; R7및 R8은 독립적으로 H, C1-C6알킬, C3-C7사이클로알킬, 페닐-(C1-C4)알킬, COR2, COOR2이거나; 또는 C1-C6알킬, C3-C7사이클로알킬, 페닐(C1-C4)알킬, C3-C7분지된 알킬중에서 독립적으로 선택된 2개 이하의 치환체로 선택적으로 치환된 C2-C7알카노일 또는 C4-C8사이클로알카노일이거나; 또는 R7및 R8은 결합된 질소와 함께, C1-C6알킬, C3-C7사이클로알킬, C3-C7분지된 알킬 또는 옥소중에서 독립적으로 선택된 2개 이하의 치환체로 선택적으로 치환된 피롤리딘, 피페리딘 또는 호모피페리딘 그룹을 의미하고; R9는 H 또는 메틸이고; R10,R11,R12및 R13은 독립적으로, C1-C4알킬 및 할로겐중에서 선택되고; m 및 n은 독립적으로 0,1 또는 2(여기서, m 또는 n은 1이상이어야 한다)이고; p는 1 내지 3이며; 단, R이 일반식(Ⅱ)의 구조이고, x가 결합인 경우, A는 반드시 C2-C6알킬렌 이외의 그룹이어야 한다.
- 제1항에 있어서, R10및 R11중 하나가 5-플루오로이고, 다른 하나가 6-클로로인 화합물.
- 제2항에 있어서, R이 하기 일반식인 화합물:
-
- 제3항에 있어서, x가 0인 화합물.
- 제4항에 있어서, A가 C2-C6알케닐 쇄이고, R1이 수소인 화합물.
- 제5항에 있어서, R12및 R13이 수소인 화합물.
- 제6항에 있어서, x가 1인 화합물.
- 제7항에 있어서, A가 C1-C6알킬렌인 화합물.
- 제8항에 있어서, R1이 벤질인 화합물.
- 제2항에 있어서, R이
-
- 이고, x가 1인 화합물.
- 제10항에 있어서, R4,R9,R12및 R15이 수소이고, R5가 수소, 메틸 또는 에틸이고, R6가 수소, 메틸, 벤질 또는 CH2COOR3인 화합물.
- 제2항에 있어서, R이
-
- 이고, x가 1인 화합물.
- 제12항에 있어서, R4,R9,R7,R8,R12및 R13이 수소이고, R5가 (CH2)pNR7R8, 메틸 또는 벤질인 화합물.
- 제12항에 있어서, R7이 COR2인 화합물.
- 제2항에 있어서, R이
-
- 이고, x는 0 또는 1인 화합물.
- 제15항에 있어서, B가 2 또는 3-피롤리딘인 화합물.
- 제2항에 있어서, R이
-
- 인 화합물.
- 제1항에서 선택된 항염증 효과량의 화합물을 포유동물에게 투여함을 포함하는, 상기 포유동물의 염증 치료 방법.
- 제1항에서 선택된 진통 효과량의 화합물을 포유동물에게 투여함을 포함하는, 상기 포유동물의 염증 치료 방법.
- 진통 또는 항염증 효과량의 제1항의 화합물 및 약학적으로 허용가능한 불활성 성분을 포함하는 약학 조성물.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/009,188 US5270331A (en) | 1993-01-26 | 1993-01-26 | Prodrugs of antiinflammatory 3-acyl-2-oxindole-1-carboxamides |
| US08/009,188 | 1993-01-26 | ||
| PCT/US1993/009813 WO1994017061A1 (en) | 1993-01-26 | 1993-10-20 | Prodrugs of antiinflammatory 3-acyl-2-oxindole-1-carboxamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR960700244A true KR960700244A (ko) | 1996-01-19 |
| KR0169827B1 KR0169827B1 (en) | 1999-01-15 |
Family
ID=21736103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950703074A KR0169827B1 (en) | 1993-01-26 | 1995-07-26 | Prodrugs of antiinflammatory 3-acyl-2-oxindole-1-carboxamides |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US5270331A (ko) |
| EP (1) | EP0681580B1 (ko) |
| JP (1) | JP2703825B2 (ko) |
| KR (1) | KR0169827B1 (ko) |
| CN (1) | CN1052003C (ko) |
| AP (1) | AP443A (ko) |
| AT (1) | ATE155137T1 (ko) |
| AU (1) | AU678187B2 (ko) |
| BR (1) | BR9307768A (ko) |
| CA (1) | CA2152919C (ko) |
| CZ (1) | CZ281046B6 (ko) |
| DE (1) | DE69312093T2 (ko) |
| DK (1) | DK0681580T3 (ko) |
| EG (1) | EG20302A (ko) |
| ES (1) | ES2104187T3 (ko) |
| FI (1) | FI940365A (ko) |
| GR (1) | GR3024591T3 (ko) |
| HR (1) | HRP940034B1 (ko) |
| HU (1) | HUT69689A (ko) |
| IL (1) | IL108384A (ko) |
| MA (1) | MA23096A1 (ko) |
| MX (1) | MX9400677A (ko) |
| MY (1) | MY138629A (ko) |
| NO (1) | NO952949L (ko) |
| NZ (1) | NZ257278A (ko) |
| OA (1) | OA10563A (ko) |
| PL (1) | PL178857B1 (ko) |
| RU (1) | RU2124514C1 (ko) |
| SI (1) | SI9300567A (ko) |
| SK (1) | SK280929B6 (ko) |
| TW (1) | TW330935B (ko) |
| UA (1) | UA41348C2 (ko) |
| WO (1) | WO1994017061A1 (ko) |
| YU (1) | YU48796B (ko) |
| ZA (1) | ZA94463B (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69305999T2 (de) * | 1993-02-09 | 1997-03-06 | Pfizer Inc., New York, N.Y. | Oxindol 1-[n-(alkoxycarbonyl)]carboxamide und 1-[n-carboxamido]carboxamide als antiinflammatorische wirkstoffe |
| AU7284096A (en) * | 1995-10-09 | 1997-04-30 | Dieter Binder | Heterocyclically-substituted 1-indole carboxamides as cyclo-oxygenase-2 inhibitors |
| BR9908510A (pt) * | 1998-03-06 | 2000-11-21 | Astrazeneca Ab | Uso de um composto, composto, processo para a preparação de um composto, composição farmacêutica, e, processo de tratar um paciente que sofre de, ou em risco de, uma doença micobacteriana |
| EP0984012A3 (en) * | 1998-08-31 | 2001-01-10 | Pfizer Products Inc. | Nitric oxide releasing oxindole prodrugs with analgesic and anti-inflammatory properties |
| AU2002325614A1 (en) * | 2001-08-16 | 2003-03-03 | Pharmacon-Forschung Und Beratung Gmbh | Compounds containing lactic acid elements, method for the production and use thereof as pharmaceutically active substances |
| CN101628842A (zh) * | 2009-08-27 | 2010-01-20 | 中国人民解放军防化指挥工程学院 | 烷氧羰基甲氧基作为羧基保护基 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4556672A (en) * | 1984-03-19 | 1985-12-03 | Pfizer Inc. | 3-Substituted 2-oxindole-1-carboxamides as analgesic and anti-inflammatory agents |
| EP0365194B1 (en) * | 1988-10-18 | 1995-08-02 | Pfizer Inc. | Prodrugs of antiinflammatory 3-acyl-2-oxindole-1-carboxamides |
| HU208421B (en) * | 1988-10-18 | 1993-10-28 | Pfizer | Process for producing starting materials for producing 3-acyl-2-oxindol-carboxamides ofantiphlogistic activity |
-
1993
- 1993-01-26 US US08/009,188 patent/US5270331A/en not_active Expired - Lifetime
- 1993-10-13 TW TW082108483A patent/TW330935B/zh active
- 1993-10-20 WO PCT/US1993/009813 patent/WO1994017061A1/en active IP Right Grant
- 1993-10-20 RU RU95117091A patent/RU2124514C1/ru not_active IP Right Cessation
- 1993-10-20 DK DK93923879.6T patent/DK0681580T3/da active
- 1993-10-20 NZ NZ257278A patent/NZ257278A/en unknown
- 1993-10-20 AT AT93923879T patent/ATE155137T1/de not_active IP Right Cessation
- 1993-10-20 SK SK912-95A patent/SK280929B6/sk unknown
- 1993-10-20 CA CA002152919A patent/CA2152919C/en not_active Expired - Fee Related
- 1993-10-20 BR BR9307768A patent/BR9307768A/pt not_active Application Discontinuation
- 1993-10-20 CZ CZ951819A patent/CZ281046B6/cs not_active IP Right Cessation
- 1993-10-20 ES ES93923879T patent/ES2104187T3/es not_active Expired - Lifetime
- 1993-10-20 UA UA95073512A patent/UA41348C2/uk unknown
- 1993-10-20 AU AU53598/94A patent/AU678187B2/en not_active Ceased
- 1993-10-20 JP JP6511478A patent/JP2703825B2/ja not_active Expired - Fee Related
- 1993-10-20 EP EP93923879A patent/EP0681580B1/en not_active Expired - Lifetime
- 1993-10-20 PL PL93309989A patent/PL178857B1/pl not_active IP Right Cessation
- 1993-10-20 DE DE69312093T patent/DE69312093T2/de not_active Expired - Fee Related
- 1993-10-21 AP APAP/P/1993/000583A patent/AP443A/en active
- 1993-10-28 SI SI9300567A patent/SI9300567A/sl not_active IP Right Cessation
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1994
- 1994-01-16 EG EG2694A patent/EG20302A/xx active
- 1994-01-18 MY MYPI94000137A patent/MY138629A/en unknown
- 1994-01-20 IL IL10838494A patent/IL108384A/en not_active IP Right Cessation
- 1994-01-21 HR HR940034A patent/HRP940034B1/xx not_active IP Right Cessation
- 1994-01-24 ZA ZA94463A patent/ZA94463B/xx unknown
- 1994-01-25 HU HU9400209A patent/HUT69689A/hu unknown
- 1994-01-25 MX MX9400677A patent/MX9400677A/es not_active IP Right Cessation
- 1994-01-25 YU YU2994A patent/YU48796B/sh unknown
- 1994-01-25 CN CN94100697A patent/CN1052003C/zh not_active Expired - Fee Related
- 1994-01-25 FI FI940365A patent/FI940365A/fi not_active Application Discontinuation
- 1994-01-25 MA MA23402A patent/MA23096A1/fr unknown
-
1995
- 1995-07-25 NO NO952949A patent/NO952949L/no unknown
- 1995-07-25 OA OA60692A patent/OA10563A/en unknown
- 1995-07-26 KR KR1019950703074A patent/KR0169827B1/ko not_active IP Right Cessation
-
1997
- 1997-09-02 GR GR970402235T patent/GR3024591T3/el unknown
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