DK169890B1 - 3-Substitueret 2-carboxy-indolderivater, farmaceutisk præparat indeholdende forbindelserne, fremgangsmåde til fremstilling af forbindelserne samt anvendelse af forbindelserne til fremstilling af et lægemiddel - Google Patents
3-Substitueret 2-carboxy-indolderivater, farmaceutisk præparat indeholdende forbindelserne, fremgangsmåde til fremstilling af forbindelserne samt anvendelse af forbindelserne til fremstilling af et lægemiddel Download PDFInfo
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- DK169890B1 DK169890B1 DK043193A DK43193A DK169890B1 DK 169890 B1 DK169890 B1 DK 169890B1 DK 043193 A DK043193 A DK 043193A DK 43193 A DK43193 A DK 43193A DK 169890 B1 DK169890 B1 DK 169890B1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9208492 | 1992-04-16 | ||
GB929208492A GB9208492D0 (en) | 1992-04-16 | 1992-04-16 | Heterocyclic compounds |
Publications (3)
Publication Number | Publication Date |
---|---|
DK43193D0 DK43193D0 (da) | 1993-04-15 |
DK43193A DK43193A (da) | 1993-10-17 |
DK169890B1 true DK169890B1 (da) | 1995-03-27 |
Family
ID=10714220
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK043193A DK169890B1 (da) | 1992-04-16 | 1993-04-15 | 3-Substitueret 2-carboxy-indolderivater, farmaceutisk præparat indeholdende forbindelserne, fremgangsmåde til fremstilling af forbindelserne samt anvendelse af forbindelserne til fremstilling af et lægemiddel |
Country Status (41)
Country | Link |
---|---|
US (4) | US5374648A (ko) |
EP (1) | EP0568136A1 (ko) |
JP (2) | JPH0649027A (ko) |
KR (1) | KR100264114B1 (ko) |
CN (1) | CN1042331C (ko) |
AP (1) | AP480A (ko) |
AT (1) | AT403917B (ko) |
AU (1) | AU666927B2 (ko) |
BE (1) | BE1006343A5 (ko) |
BG (1) | BG62136B1 (ko) |
BR (1) | BR1100323A (ko) |
CA (3) | CA2094073A1 (ko) |
CH (1) | CH685630A5 (ko) |
CY (1) | CY2038B1 (ko) |
CZ (1) | CZ285799B6 (ko) |
DK (1) | DK169890B1 (ko) |
ES (1) | ES2105924B1 (ko) |
FI (1) | FI106198B (ko) |
FR (1) | FR2690919B1 (ko) |
GB (2) | GB9208492D0 (ko) |
GE (1) | GEP19991704B (ko) |
GR (1) | GR1001619B (ko) |
HK (1) | HK95797A (ko) |
HU (2) | HU217964B (ko) |
IL (1) | IL105412A (ko) |
IS (1) | IS3994A (ko) |
IT (1) | IT1265325B1 (ko) |
LU (1) | LU88248A1 (ko) |
MX (1) | MX9302195A (ko) |
MY (1) | MY112232A (ko) |
NO (1) | NO301879B1 (ko) |
NZ (1) | NZ247413A (ko) |
OA (1) | OA10103A (ko) |
PL (1) | PL176451B1 (ko) |
RO (1) | RO113242B1 (ko) |
RU (1) | RU2129544C1 (ko) |
SE (1) | SE504336C2 (ko) |
SK (1) | SK281941B6 (ko) |
TW (1) | TW224457B (ko) |
WO (1) | WO1993021153A1 (ko) |
ZA (1) | ZA932642B (ko) |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9304500D0 (en) * | 1993-03-05 | 1993-04-21 | Glaxo Spa | Heterocyclic compounds |
US5519048A (en) * | 1993-05-27 | 1996-05-21 | Merrell Pharmaceuticals Inc. | 3-(indol-3-yl)-propenoic acid derivatives and pharmaceutical compositions thereof |
EP0701551B1 (en) * | 1993-05-27 | 1997-04-16 | Merrell Pharmaceuticals Inc. | 3-(indol-3-yl) propenoic acid derivatives useful as nmda antagonists |
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 (ko) * | 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 |
US6030968A (en) * | 1996-09-17 | 2000-02-29 | The Regents Of The University Of California | Positive AMPA receptor modulation to enhance brain neurotrophic factor expression |
EP0929521B1 (en) * | 1996-09-30 | 2005-11-09 | 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 |
BRPI9909201B8 (pt) * | 1998-03-26 | 2021-05-25 | Astellas Pharma Inc | formulação de composto de macrolídeo de liberação controlada |
WO2003039540A2 (en) * | 2001-11-09 | 2003-05-15 | Sepracor Inc. | D-amino acid oxidase inhibitors for learning and memory |
CA2468544A1 (en) * | 2001-12-10 | 2003-06-19 | Amgen Inc. | Vanilloid receptor ligands |
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 |
WO2004108733A1 (en) * | 2003-06-05 | 2004-12-16 | Pfizer Products Inc. | Beta-lactamase inhibitor prodrug |
US7671072B2 (en) * | 2003-11-26 | 2010-03-02 | Pfizer Inc. | Aminopyrazole derivatives as GSK-3 inhibitors |
PL380887A1 (pl) * | 2003-12-29 | 2007-04-02 | Sepracor Inc. | Pirolowe i pirazolowe inhibitory DAAO |
US20060002999A1 (en) * | 2004-06-17 | 2006-01-05 | Forest Laboratories, Inc. | Immediate release formulations of 1-aminocyclohexane compounds, memantine and neramexane |
CA2614282A1 (en) | 2005-07-06 | 2007-01-11 | Sepracor 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 |
ES2594156T3 (es) | 2006-01-06 | 2016-12-16 | Sunovion Pharmaceuticals Inc. | Cicloalquilaminas como inhibidores de la recaptación de monoaminas |
JP5438975B2 (ja) | 2006-01-06 | 2014-03-12 | サノビオン ファーマシューティカルズ インク | テトラロン系モノアミン再取り込み阻害剤 |
WO2007115185A2 (en) | 2006-03-31 | 2007-10-11 | Sepracor Inc. | Preparation of chiral amides and amines |
US7579370B2 (en) * | 2006-06-30 | 2009-08-25 | Sepracor Inc. | Fused heterocycles |
US7884124B2 (en) * | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
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 |
US7902252B2 (en) * | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
WO2008089453A2 (en) | 2007-01-18 | 2008-07-24 | Sepracor Inc. | Inhibitors of d-amino acid oxidase |
NZ580429A (en) | 2007-05-31 | 2012-04-27 | Sepracor Inc | Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors |
US20090247644A1 (en) * | 2008-03-28 | 2009-10-01 | 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 |
CA2755118A1 (en) * | 2009-03-10 | 2010-09-16 | Santen Pharmaceutical Co., Ltd. | Preventive or therapeutic agents for optic nerve disorders comprising 4,6-dichloro-1h-indole-2-carboxylic acid derivatives or salts thereof as active ingredients |
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 |
CN112773798B (zh) | 2014-04-30 | 2024-03-29 | 宇凤·简·曾 | 作为d-氨基酸氧化酶抑制剂的已知化合物的用途 |
CA3036250C (en) | 2016-09-14 | 2023-09-26 | Yufeng Jane Tseng | Novel substituted benzimidazole derivatives as d-amino acid oxidase (daao) inhibitors |
KR102609676B1 (ko) | 2017-06-12 | 2023-12-05 | 글리테크 엘엘씨. | Nmda 길항제 및 d2/5ht2a 또는 선택적 5ht2a 길항제를 이용한 우울증의 치료 |
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 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
JP3058688B2 (ja) * | 1990-07-16 | 2000-07-04 | メレルダウファーマスーティカルズ インコーポレイテッド | 興奮性アミノ酸拮抗剤 |
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 ES ES09300771A patent/ES2105924B1/es not_active Expired - Lifetime
- 1993-04-15 JP JP5088844A patent/JPH0649027A/ja active Pending
- 1993-04-15 SK SK1241-94A patent/SK281941B6/sk unknown
- 1993-04-15 FR FR9304452A patent/FR2690919B1/fr not_active Expired - Fee Related
- 1993-04-15 RU RU94045915A patent/RU2129544C1/ru active
- 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 NZ NZ247413A patent/NZ247413A/en unknown
- 1993-04-15 CZ CZ942543A patent/CZ285799B6/cs not_active IP Right Cessation
- 1993-04-15 LU LU88248A patent/LU88248A1/fr unknown
- 1993-04-15 CA CA002094075A patent/CA2094075A1/en not_active Abandoned
- 1993-04-15 HU HU9402975A patent/HU217964B/hu not_active IP Right Cessation
- 1993-04-15 JP JP5517997A patent/JPH07505407A/ja active Pending
- 1993-04-15 IS IS3994A patent/IS3994A/is unknown
- 1993-04-15 CH CH1133/93A patent/CH685630A5/fr not_active IP Right Cessation
- 1993-04-15 US US08/047,429 patent/US5374648A/en not_active Expired - Fee Related
- 1993-04-15 AU AU36923/93A patent/AU666927B2/en not_active Ceased
- 1993-04-15 RO RO94-01658A patent/RO113242B1/ro unknown
- 1993-04-15 GR GR930100154A patent/GR1001619B/el not_active IP Right Cessation
- 1993-04-15 IL IL105412A patent/IL105412A/en not_active IP Right Cessation
- 1993-04-15 AT AT0075293A patent/AT403917B/de not_active IP Right Cessation
- 1993-04-15 PL PL93305554A patent/PL176451B1/pl unknown
- 1993-04-15 MX MX9302195A patent/MX9302195A/es not_active IP Right Cessation
- 1993-04-15 DK DK043193A patent/DK169890B1/da active
- 1993-04-15 US US08/046,947 patent/US5373018A/en not_active Expired - Fee Related
- 1993-04-15 CA CA002094076A patent/CA2094076A1/en not_active Abandoned
- 1993-04-15 MY MYPI93000690A patent/MY112232A/en unknown
- 1993-04-15 IT IT93RM000236A patent/IT1265325B1/it active IP Right Grant
- 1993-04-15 WO PCT/EP1993/000938 patent/WO1993021153A1/en active IP Right Grant
- 1993-04-15 KR KR1019940703668A patent/KR100264114B1/ko not_active IP Right Cessation
- 1993-04-15 BE BE9300371A patent/BE1006343A5/fr active
- 1993-04-15 CN CN93105797A patent/CN1042331C/zh not_active Expired - Fee Related
- 1993-04-15 EP EP93201103A patent/EP0568136A1/en not_active Withdrawn
- 1993-04-15 SE SE9301241A patent/SE504336C2/sv not_active IP Right Cessation
- 1993-04-15 US US08/047,430 patent/US5374649A/en not_active Expired - Fee Related
- 1993-04-16 GE GEAP19932602A patent/GEP19991704B/en unknown
- 1993-04-16 AP APAP/P/1993/000524A patent/AP480A/en active
- 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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