FI106198B - Menetelmä terapeuttisesti käyttökelpoisten 3-substituoitujen 2-karboksi-indolijohdannaisten valmistamiseksi - Google Patents
Menetelmä terapeuttisesti käyttökelpoisten 3-substituoitujen 2-karboksi-indolijohdannaisten valmistamiseksi Download PDFInfo
- Publication number
- FI106198B FI106198B FI944800A FI944800A FI106198B FI 106198 B FI106198 B FI 106198B FI 944800 A FI944800 A FI 944800A FI 944800 A FI944800 A FI 944800A FI 106198 B FI106198 B FI 106198B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- ethenyl
- indole
- carboxylic acid
- Prior art date
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- -1 3-substituted 2-carboxyindole Chemical class 0.000 title claims description 58
- 238000000034 method Methods 0.000 title claims description 33
- 238000002360 preparation method Methods 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 145
- 150000003839 salts Chemical class 0.000 claims description 35
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- XLMJSBMZZPMBBS-BQYQJAHWSA-N 4,6-dichloro-3-[(e)-3-(4-ethoxyanilino)-3-oxoprop-1-enyl]-1h-indole-2-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1NC(=O)\C=C\C1=C(C(O)=O)NC2=CC(Cl)=CC(Cl)=C12 XLMJSBMZZPMBBS-BQYQJAHWSA-N 0.000 claims description 2
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- 229960003750 ethyl chloride Drugs 0.000 description 1
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- 229940117360 ethyl pyruvate Drugs 0.000 description 1
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- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000001259 mesencephalon Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- OHKAPCLENKAVMN-UHFFFAOYSA-N methyl 3-(3-anilino-3-oxoprop-1-ynyl)-4,6-dichloro-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(Cl)=CC(Cl)=C2C=1C#CC(=O)NC1=CC=CC=C1 OHKAPCLENKAVMN-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
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- 235000010981 methylcellulose Nutrition 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 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
- 229940127240 opiate Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
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- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- YNWSXIWHOSSPCO-UHFFFAOYSA-N rhodium(2+) Chemical compound [Rh+2] YNWSXIWHOSSPCO-UHFFFAOYSA-N 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
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- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- MRAZYSAHIPFJGX-UHFFFAOYSA-N trimethyl(1h-pyrazol-5-yl)silane Chemical compound C[Si](C)(C)C1=CC=NN1 MRAZYSAHIPFJGX-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9208492 | 1992-04-16 | ||
| GB929208492A GB9208492D0 (en) | 1992-04-16 | 1992-04-16 | Heterocyclic compounds |
| EP9300938 | 1993-04-15 | ||
| PCT/EP1993/000938 WO1993021153A1 (en) | 1992-04-16 | 1993-04-15 | Indole-2-carboxylic acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI944800L FI944800L (fi) | 1994-10-12 |
| FI944800A0 FI944800A0 (fi) | 1994-10-12 |
| FI106198B true FI106198B (fi) | 2000-12-15 |
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| FI944800A FI106198B (fi) | 1992-04-16 | 1994-10-12 | Menetelmä terapeuttisesti käyttökelpoisten 3-substituoitujen 2-karboksi-indolijohdannaisten valmistamiseksi |
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| GB9304500D0 (en) * | 1993-03-05 | 1993-04-21 | Glaxo Spa | Heterocyclic compounds |
| AU681402B2 (en) * | 1993-05-27 | 1997-08-28 | Aventis Inc. | 3-(indol-3-yl) propenoic acid derivatives and as NMDA antagonists |
| US5519048A (en) * | 1993-05-27 | 1996-05-21 | Merrell Pharmaceuticals Inc. | 3-(indol-3-yl)-propenoic acid derivatives and pharmaceutical compositions thereof |
| GB9319243D0 (en) * | 1993-09-17 | 1993-11-03 | Glaxo Spa | Heterocyclic compounds |
| GB9321221D0 (en) * | 1993-10-14 | 1993-12-01 | Glaxo Spa | Heterocyclic compounds |
| TW280819B (Sortimente) * | 1993-11-17 | 1996-07-11 | Sumitomo Pharma | |
| US5563157B1 (en) | 1994-10-31 | 1999-02-02 | Hoecst Marion Roussel Inc | Heterocycle substituted propenoic acid derivatives and pharmaceutical compositions thereof |
| GB9502695D0 (en) * | 1995-02-11 | 1995-03-29 | Glaxo Spa | Pharmaceutical composition |
| GB9504361D0 (en) * | 1995-03-04 | 1995-04-26 | Glaxo Spa | Heterocyclic compounds |
| WO1998011892A1 (en) * | 1996-09-17 | 1998-03-26 | The Regents Of The University Of California | Positive ampa receptor modulation to enhance brain neurotrophic factor expression |
| AU732997B2 (en) * | 1996-09-30 | 2001-05-03 | Aventis Pharmaceuticals Inc. | NMDA (N-methyl-D-aspartate) antagonists |
| US5922752A (en) * | 1997-06-11 | 1999-07-13 | Hoechst Marion Roussell, Inc. | NMDA (n-methyl-d-aspartate) antagonists |
| ID27825A (id) * | 1998-03-26 | 2001-04-26 | Fujisawa Pharmaceutical Co | Sediaan lepas lambat |
| EP1306378A4 (en) * | 2000-07-31 | 2005-02-09 | Dainippon Pharmaceutical Co | DRUGS AGAINST DEMENTIA CONTAINING 2-ARYL-8-OXODIHYDROPURINE DERIVATIVES AS AN ACTIVE INGREDIENT |
| US20030162825A1 (en) * | 2001-11-09 | 2003-08-28 | Sepracor Inc. | D-amino acid oxidase inhibitors for learning and memory |
| WO2003049702A2 (en) * | 2001-12-10 | 2003-06-19 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| PA8579701A1 (es) * | 2002-08-23 | 2005-05-24 | Pfizer Prod Inc | Profarmaco inhibidor de beta-lactamasa |
| DE10306202A1 (de) * | 2003-02-13 | 2004-08-26 | Grünenthal GmbH | Arzneimittel enthaltend substituierte 2-Aryl-Aminoessigsäure-Verbindungen und/oder substituierte 2-Heteroaryl-Aminoessigsäure-Verbindungen |
| JP2006526612A (ja) * | 2003-06-05 | 2006-11-24 | ファイザー・プロダクツ・インク | ベータ−ラクタマーゼ阻害剤・プロドラッグ |
| RU2247563C1 (ru) * | 2003-06-16 | 2005-03-10 | Пятигорская государственная фармацевтическая академия | Способ получения твердой лекарственной формы, содержащей глюкозамина гидрохлорид |
| ATE473967T1 (de) * | 2003-11-26 | 2010-07-15 | Pfizer Prod Inc | Aminopyrazolderivate als gsk-3-inhibitoren |
| WO2005066135A2 (en) * | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole daao inhibitors |
| RU2281755C2 (ru) * | 2004-04-19 | 2006-08-20 | Пятигорская государственная фармацевтическая академия | Композиция - лекарственная форма противоартрозного средства глюкозамина гидрохлорида для ректального применения |
| US20060002999A1 (en) * | 2004-06-17 | 2006-01-05 | Forest Laboratories, Inc. | Immediate release formulations of 1-aminocyclohexane compounds, memantine and neramexane |
| AU2006264317B2 (en) | 2005-07-06 | 2012-02-23 | Sunovion Pharmaceuticals Inc. | Combinations of eszopiclone and trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders |
| CN104276955A (zh) | 2006-01-06 | 2015-01-14 | 赛诺维信制药公司 | 基于四氢萘酮的单胺再摄取抑制剂 |
| NZ569630A (en) * | 2006-01-06 | 2011-09-30 | Sepracor Inc | Cycloalkylamines as monoamine reuptake inhibitors |
| AU2007233041B2 (en) | 2006-03-31 | 2013-05-02 | Sepracor Inc. | Preparation of chiral amides and amines |
| US7884124B2 (en) * | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| US7579370B2 (en) * | 2006-06-30 | 2009-08-25 | Sepracor Inc. | Fused heterocycles |
| US20080082066A1 (en) * | 2006-10-02 | 2008-04-03 | Weyerhaeuser Co. | Crosslinked carboxyalkyl cellulose fibers having non-permanent and temporary crosslinks |
| EP1942104A1 (en) | 2006-12-20 | 2008-07-09 | sanofi-aventis | Heteroarylcyclopropanecarboxamides and their use as pharmaceuticals |
| MX2009007410A (es) * | 2007-01-18 | 2009-09-09 | Sepracor Inc | Inhibidores de d-aminoacido oxidasa. |
| US7902252B2 (en) * | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| WO2008151156A1 (en) | 2007-05-31 | 2008-12-11 | Sepracor Inc. | Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors |
| WO2009151498A2 (en) * | 2008-03-28 | 2009-12-17 | Forest Laboratories Holdings Limited | Memantine formulations |
| WO2010017418A1 (en) * | 2008-08-07 | 2010-02-11 | Sepracor Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
| KR20110126132A (ko) * | 2009-03-10 | 2011-11-22 | 산텐 세이야꾸 가부시키가이샤 | 4,6-디클로로-1η-인돌-2-카르복실산 유도체 또는 이의 염을 유효 성분으로서 함유하는 시신경 장애의 예방 또는 치료제 |
| WO2011017634A2 (en) * | 2009-08-07 | 2011-02-10 | Sepracore Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
| US9737531B2 (en) | 2012-07-12 | 2017-08-22 | Glytech, Llc | Composition and method for treatment of depression and psychosis in humans |
| USRE49340E1 (en) | 2014-04-30 | 2022-12-20 | Yufeng Jane Tseng | Use of known compounds as D-amino acid oxidase inhibitors |
| CA3207747A1 (en) | 2016-09-14 | 2018-03-22 | Yufeng Jane Tseng | Novel substituted benzimidazole derivatives as d-amino acid oxidase (daao) inhibitors |
| WO2018229744A1 (en) | 2017-06-12 | 2018-12-20 | Glytech Llc. | Treatment of depression with nmda antagonists and d2/5ht2a or selective 5ht2a antagonists |
| CN112707874A (zh) * | 2020-12-29 | 2021-04-27 | 广东中科药物研究有限公司 | 一种抗病毒化合物及其制备方法 |
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|---|---|---|---|---|
| US3010971A (en) * | 1960-08-04 | 1961-11-28 | Smith Kline French Lab | Cyclopropylamine derivatives and processes for their preparation |
| DK500285A (da) * | 1984-11-02 | 1986-05-03 | Glaxo Group Ltd | Cephalosporinantibiotika |
| US4960786A (en) * | 1989-04-24 | 1990-10-02 | Merrell Dow Pharmaceuticals Inc. | Excitatory amino acid antagonists |
| PT93943A (pt) * | 1989-05-05 | 1991-02-08 | Searle & Co | Processo para a preparacao de composicoes contendo compostos indole-2-carboxilato para tratamento de perturbacoes do snc |
| DE69118539T2 (de) * | 1990-07-16 | 1996-09-19 | Merrell Dow Pharmaceuticals Inc., Cincinnati, Ohio | Exzitatorische Aminosäureantagonisten |
| US5284862A (en) * | 1991-03-18 | 1994-02-08 | Warner-Lambert Company | Derivatives of 2-carboxyindoles having pharmaceutical activity |
| US5145845A (en) * | 1991-05-14 | 1992-09-08 | Warner-Lambert Co. | Substituted 2-carboxylindoles having pharmaceutical activity |
-
1992
- 1992-04-16 GB GB929208492A patent/GB9208492D0/en active Pending
-
1993
- 1993-04-14 ZA ZA932642A patent/ZA932642B/xx unknown
- 1993-04-15 AT AT0075293A patent/AT403917B/de not_active IP Right Cessation
- 1993-04-15 CZ CZ942543A patent/CZ285799B6/cs not_active IP Right Cessation
- 1993-04-15 SK SK1241-94A patent/SK281941B6/sk unknown
- 1993-04-15 CH CH1133/93A patent/CH685630A5/fr not_active IP Right Cessation
- 1993-04-15 EP EP93201103A patent/EP0568136A1/en not_active Withdrawn
- 1993-04-15 FR FR9304452A patent/FR2690919B1/fr not_active Expired - Fee Related
- 1993-04-15 CA CA002094073A patent/CA2094073A1/en not_active Abandoned
- 1993-04-15 GB GB9307808A patent/GB2266091B/en not_active Expired - Fee Related
- 1993-04-15 DK DK043193A patent/DK169890B1/da active
- 1993-04-15 MX MX9302195A patent/MX9302195A/es not_active IP Right Cessation
- 1993-04-15 CA CA002094076A patent/CA2094076A1/en not_active Abandoned
- 1993-04-15 KR KR1019940703668A patent/KR100264114B1/ko not_active Expired - Fee Related
- 1993-04-15 MY MYPI93000690A patent/MY112232A/en unknown
- 1993-04-15 RO RO94-01658A patent/RO113242B1/ro unknown
- 1993-04-15 NZ NZ247413A patent/NZ247413A/en unknown
- 1993-04-15 BE BE9300371A patent/BE1006343A5/fr active
- 1993-04-15 JP JP5517997A patent/JPH07505407A/ja active Pending
- 1993-04-15 ES ES09300771A patent/ES2105924B1/es not_active Expired - Lifetime
- 1993-04-15 WO PCT/EP1993/000938 patent/WO1993021153A1/en not_active Ceased
- 1993-04-15 IT IT93RM000236A patent/IT1265325B1/it active IP Right Grant
- 1993-04-15 US US08/046,947 patent/US5373018A/en not_active Expired - Fee Related
- 1993-04-15 CN CN93105797A patent/CN1042331C/zh not_active Expired - Fee Related
- 1993-04-15 SE SE9301241A patent/SE504336C2/sv not_active IP Right Cessation
- 1993-04-15 PL PL93305554A patent/PL176451B1/pl unknown
- 1993-04-15 CA CA002094075A patent/CA2094075A1/en not_active Abandoned
- 1993-04-15 US US08/047,430 patent/US5374649A/en not_active Expired - Fee Related
- 1993-04-15 RU RU94045915A patent/RU2129544C1/ru active
- 1993-04-15 JP JP5088844A patent/JPH0649027A/ja active Pending
- 1993-04-15 AU AU36923/93A patent/AU666927B2/en not_active Ceased
- 1993-04-15 IL IL105412A patent/IL105412A/en not_active IP Right Cessation
- 1993-04-15 US US08/047,429 patent/US5374648A/en not_active Expired - Fee Related
- 1993-04-15 GR GR930100154A patent/GR1001619B/el not_active IP Right Cessation
- 1993-04-15 HU HU9402975A patent/HU217964B/hu not_active IP Right Cessation
- 1993-04-15 LU LU88248A patent/LU88248A1/fr unknown
- 1993-04-15 IS IS3994A patent/IS3994A/is unknown
- 1993-04-16 AP APAP/P/1993/000524A patent/AP480A/en active
- 1993-04-16 GE GEAP19932602A patent/GEP19991704B/en unknown
- 1993-05-06 TW TW082103531A patent/TW224457B/zh active
-
1994
- 1994-10-10 OA OA60570A patent/OA10103A/en unknown
- 1994-10-12 FI FI944800A patent/FI106198B/fi active
- 1994-10-14 NO NO943913A patent/NO301879B1/no not_active IP Right Cessation
- 1994-10-14 BG BG99111A patent/BG62136B1/bg unknown
- 1994-12-08 US US08/351,762 patent/US5510367A/en not_active Expired - Fee Related
-
1995
- 1995-06-29 HU HU95P/P00538P patent/HU211826A9/hu unknown
-
1997
- 1997-04-22 BR BR1100323-5A patent/BR1100323A/pt active IP Right Grant
- 1997-06-26 HK HK95797A patent/HK95797A/xx not_active IP Right Cessation
-
1998
- 1998-04-30 CY CY9802038A patent/CY2038B1/xx unknown
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