PT100441A - Pirrolidinonas, seu processo de preparacao, composicoes farmaceuticas que as contem e uso - Google Patents
Pirrolidinonas, seu processo de preparacao, composicoes farmaceuticas que as contem e uso Download PDFInfo
- Publication number
- PT100441A PT100441A PT100441A PT10044192A PT100441A PT 100441 A PT100441 A PT 100441A PT 100441 A PT100441 A PT 100441A PT 10044192 A PT10044192 A PT 10044192A PT 100441 A PT100441 A PT 100441A
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- Prior art keywords
- formula
- cyclopentyloxy
- methoxyphenyl
- substituted
- mmol
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 227
- -1 2-imidazolyl Chemical group 0.000 claims description 119
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 46
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 42
- 102000003390 tumor necrosis factor Human genes 0.000 claims description 41
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 34
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
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- 230000009467 reduction Effects 0.000 claims description 10
- 229910004013 NO 2 Inorganic materials 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
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- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
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- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 6
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- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 235000019000 fluorine Nutrition 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
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- ZRSVIQCPYIYIKX-UHFFFAOYSA-N methyl 4-[[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidin-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(=O)CC(C=2C=C(OC3CCCC3)C(OC)=CC=2)C1 ZRSVIQCPYIYIKX-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- AFFCCLBPSQWROV-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-1-[(2,4-diaminophenyl)methyl]pyrrolidin-2-one Chemical compound COC1=CC=C(C2CC(=O)N(CC=3C(=CC(N)=CC=3)N)C2)C=C1OC1CCCC1 AFFCCLBPSQWROV-UHFFFAOYSA-N 0.000 claims description 3
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- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
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- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- GMTVBECLHDYSRJ-UHFFFAOYSA-N n-[3-acetamido-4-[[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidin-1-yl]methyl]phenyl]acetamide Chemical compound COC1=CC=C(C2CC(=O)N(CC=3C(=CC(NC(C)=O)=CC=3)NC(C)=O)C2)C=C1OC1CCCC1 GMTVBECLHDYSRJ-UHFFFAOYSA-N 0.000 claims description 2
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- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- LFSZLTUNAORFFB-UHFFFAOYSA-N n-[2-[[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidin-1-yl]methyl]-5-nitrophenyl]acetamide Chemical compound COC1=CC=C(C2CC(=O)N(CC=3C(=CC(=CC=3)[N+]([O-])=O)NC(C)=O)C2)C=C1OC1CCCC1 LFSZLTUNAORFFB-UHFFFAOYSA-N 0.000 description 1
- SYTHZEZMUMAGHJ-UHFFFAOYSA-N n-[4-[[4-(3,4-dimethoxyphenyl)-2-oxopyrrolidin-1-yl]methyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C1CC(=O)N(CC=2C=CC(NC(C)=O)=CC=2)C1 SYTHZEZMUMAGHJ-UHFFFAOYSA-N 0.000 description 1
- XPOHHUOICIXCRE-UHFFFAOYSA-N n-[4-[[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidin-1-yl]methyl]-3-nitrophenyl]acetamide Chemical compound COC1=CC=C(C2CC(=O)N(CC=3C(=CC(NC(C)=O)=CC=3)[N+]([O-])=O)C2)C=C1OC1CCCC1 XPOHHUOICIXCRE-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- 238000002953 preparative HPLC Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69462491A | 1991-05-02 | 1991-05-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT100441A true PT100441A (pt) | 1993-09-30 |
Family
ID=24789624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT100441A PT100441A (pt) | 1991-05-02 | 1992-04-30 | Pirrolidinonas, seu processo de preparacao, composicoes farmaceuticas que as contem e uso |
Country Status (10)
Families Citing this family (129)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9311281D0 (en) * | 1993-06-01 | 1993-07-21 | Rhone Poulenc Rorer Ltd | Novel composition of matter |
| US5698711A (en) | 1991-01-28 | 1997-12-16 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic- or heteroatom-containing linking group |
| GB9212673D0 (en) * | 1992-06-15 | 1992-07-29 | Celltech Ltd | Chemical compounds |
| US5679696A (en) * | 1992-07-28 | 1997-10-21 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic-or heteroatom-containing linking group |
| GB9222253D0 (en) * | 1992-10-23 | 1992-12-09 | Celltech Ltd | Chemical compounds |
| CA2400368A1 (en) | 1992-12-02 | 1994-06-09 | Allen J. Duplantier | Catechol diethers as selective pde iv inhibitors |
| US5814651A (en) * | 1992-12-02 | 1998-09-29 | Pfizer Inc. | Catechol diethers as selective PDEIV inhibitors |
| TW263495B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1992-12-23 | 1995-11-21 | Celltech Ltd | |
| GB9226830D0 (en) * | 1992-12-23 | 1993-02-17 | Celltech Ltd | Chemical compounds |
| US5622977A (en) * | 1992-12-23 | 1997-04-22 | Celltech Therapeutics Limited | Tri-substituted (aryl or heteroaryl) derivatives and pharmaceutical compositions containing the same |
| GB9304919D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| GB9304920D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| ATE275951T1 (de) * | 1993-06-18 | 2004-10-15 | Smithkline Beecham Corp | Verfahren zur identifizierung eines pde iv hemmers |
| DE69430747T2 (de) | 1993-07-28 | 2003-03-06 | Aventis Pharma Ltd., West Malling | Verbindungen als pde iv und tnf inhibitoren |
| US5665754A (en) * | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
| ES2139754T3 (es) * | 1993-11-26 | 2000-02-16 | Pfizer | 3-fenil-2-isoxazolinas como agentes antiinflamatorios. |
| CZ283564B6 (cs) * | 1993-11-26 | 1998-05-13 | Pfizer Inc. | 3-Aryl-2-isoxazolin-5-hydroxamové kyseliny a farmaceutické prostředky na jejich bázi |
| ATE260911T1 (de) * | 1993-12-22 | 2004-03-15 | Celltech R&D Ltd | Trisubstituierte phenyl-derivate, verfahren zu deren herstellung und deren verwendung als phosphodiesterase (typ iv) hemmstoffe |
| GB9326173D0 (en) * | 1993-12-22 | 1994-02-23 | Celltech Ltd | Chemical compounds and process |
| CA2143143A1 (en) * | 1994-03-08 | 1995-09-09 | Toshihiko Tanaka | 3-phenylpyrrolidine derivatives |
| EP0749307A1 (en) * | 1994-03-09 | 1996-12-27 | Pfizer Inc. | Isoxazoline compounds as 5-lipoxygenase inhibitors |
| DK0749428T3 (da) * | 1994-03-09 | 1998-11-16 | Pfizer | Isooxazolinforbindelser som inhibitorer af TNF-frigivelse |
| US5672622A (en) * | 1994-04-21 | 1997-09-30 | Berlex Laboratories, Inc. | Treatment of multiple sclerosis |
| EP0758233B1 (en) * | 1994-04-21 | 2003-12-03 | Schering Aktiengesellschaft | Pde iv inhibitors for treating multiple sclerosis |
| EP1380291A1 (en) * | 1994-04-21 | 2004-01-14 | Schering Aktiengesellschaft | PDE IV inhibitors for treating multiple sclerosis |
| US6060501A (en) * | 1994-06-02 | 2000-05-09 | Schering Aktiengesellschaft | Combined treatment of multiple sclerosis |
| US5998428A (en) * | 1995-05-31 | 1999-12-07 | Smithkline Beecham Corporation | Compounds and methods for treating PDE IV-related diseases |
| US6245774B1 (en) | 1994-06-21 | 2001-06-12 | Celltech Therapeutics Limited | Tri-substituted phenyl or pyridine derivatives |
| US5786354A (en) * | 1994-06-21 | 1998-07-28 | Celltech Therapeutics, Limited | Tri-substituted phenyl derivatives and processes for their preparation |
| GB9412573D0 (en) * | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9412571D0 (en) | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
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|---|---|---|---|---|
| GB1350582A (en) * | 1970-07-24 | 1974-04-18 | Ucb Sa | Cerivatives of 2-pyrrolidinone |
| JPS4916872A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-04-21 | 1974-02-14 | ||
| JPS5238227B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-06-14 | 1977-09-28 | ||
| JPS5232064B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-06-14 | 1977-08-19 | ||
| JPS5182258A (ja) * | 1974-04-25 | 1976-07-19 | Yoshitomi Pharmaceutical | Pirorijinonjudotaino seizoho |
| US4476311A (en) * | 1980-03-12 | 1984-10-09 | The Purdue Frederick Company | Analgesic 4-carboxy-pyrrolidin-2-one compound |
| DE3823299A1 (de) * | 1988-07-07 | 1990-01-11 | Schering Ag | Substituierte phenyl-pyrrolidin-2-one, -oxazolidin-2-one und -imidazolidin-2-one, ihre herstellung sowie verwendung in arzneimitteln |
-
1992
- 1992-04-30 PT PT100441A patent/PT100441A/pt not_active Application Discontinuation
- 1992-05-01 JP JP4511481A patent/JPH06507405A/ja active Pending
- 1992-05-01 EP EP92911583A patent/EP0584208A1/en not_active Withdrawn
- 1992-05-01 WO PCT/US1992/003613 patent/WO1992019594A1/en not_active Application Discontinuation
- 1992-05-01 CA CA002102106A patent/CA2102106A1/en not_active Abandoned
- 1992-05-01 CN CN92104385A patent/CN1067244A/zh active Pending
- 1992-05-01 AU AU19170/92A patent/AU1917092A/en not_active Abandoned
- 1992-05-04 ZA ZA923210A patent/ZA923210B/xx unknown
- 1992-05-04 MX MX9202090A patent/MX9202090A/es unknown
- 1992-07-01 IE IE137692A patent/IE921376A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2102106A1 (en) | 1992-11-03 |
| ZA923210B (en) | 1993-03-31 |
| AU1917092A (en) | 1992-12-21 |
| IE921376A1 (en) | 1992-11-04 |
| WO1992019594A1 (en) | 1992-11-12 |
| JPH06507405A (ja) | 1994-08-25 |
| MX9202090A (es) | 1992-11-01 |
| CN1067244A (zh) | 1992-12-23 |
| EP0584208A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-03-23 |
| EP0584208A1 (en) | 1994-03-02 |
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