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
-
- 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 (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB929208492A GB9208492D0 (en) | 1992-04-16 | 1992-04-16 | Heterocyclic compounds |
GB9208492 | 1992-04-16 |
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) | US5373018A (el) |
EP (1) | EP0568136A1 (el) |
JP (2) | JPH07505407A (el) |
KR (1) | KR100264114B1 (el) |
CN (1) | CN1042331C (el) |
AP (1) | AP480A (el) |
AT (1) | AT403917B (el) |
AU (1) | AU666927B2 (el) |
BE (1) | BE1006343A5 (el) |
BG (1) | BG62136B1 (el) |
BR (1) | BR1100323A (el) |
CA (3) | CA2094075A1 (el) |
CH (1) | CH685630A5 (el) |
CY (1) | CY2038B1 (el) |
CZ (1) | CZ285799B6 (el) |
DK (1) | DK169890B1 (el) |
ES (1) | ES2105924B1 (el) |
FI (1) | FI106198B (el) |
FR (1) | FR2690919B1 (el) |
GB (2) | GB9208492D0 (el) |
GE (1) | GEP19991704B (el) |
GR (1) | GR1001619B (el) |
HK (1) | HK95797A (el) |
HU (2) | HU217964B (el) |
IL (1) | IL105412A (el) |
IS (1) | IS3994A (el) |
IT (1) | IT1265325B1 (el) |
LU (1) | LU88248A1 (el) |
MX (1) | MX9302195A (el) |
MY (1) | MY112232A (el) |
NO (1) | NO301879B1 (el) |
NZ (1) | NZ247413A (el) |
OA (1) | OA10103A (el) |
PL (1) | PL176451B1 (el) |
RO (1) | RO113242B1 (el) |
RU (1) | RU2129544C1 (el) |
SE (1) | SE504336C2 (el) |
SK (1) | SK281941B6 (el) |
TW (1) | TW224457B (el) |
WO (1) | WO1993021153A1 (el) |
ZA (1) | ZA932642B (el) |
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 |
ATE151750T1 (de) * | 1993-05-27 | 1997-05-15 | Merrell Pharma Inc | 3-(indol-3-yl) propensäurderivate, die als nmda- antagonisten nützlich sind |
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 (el) * | 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 |
BR9712144A (pt) * | 1996-09-30 | 1999-08-31 | Hoechst Marion Roussel Inc | Novos antagonistas de nmda (d- aspartato de n-metila). |
US5922752A (en) * | 1997-06-11 | 1999-07-13 | Hoechst Marion Roussell, Inc. | NMDA (n-methyl-d-aspartate) antagonists |
AU749623B2 (en) * | 1998-03-26 | 2002-06-27 | Astellas Pharma Inc. | Sustained release preparations |
WO2003039540A2 (en) * | 2001-11-09 | 2003-05-15 | Sepracor Inc. | D-amino acid oxidase inhibitors for learning and memory |
JP2005518371A (ja) * | 2001-12-10 | 2005-06-23 | アムジエン・インコーポレーテツド | バニロイド受容体リガンド及び治療に於けるこれらの使用 |
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 |
US7671072B2 (en) * | 2003-11-26 | 2010-03-02 | Pfizer Inc. | Aminopyrazole derivatives as GSK-3 inhibitors |
KR20060128976A (ko) * | 2003-12-29 | 2006-12-14 | 세프라코 아이엔시. | 피롤 및 피라졸 디에이에이오 억제제 |
US20060002999A1 (en) * | 2004-06-17 | 2006-01-05 | Forest Laboratories, Inc. | Immediate release formulations of 1-aminocyclohexane compounds, memantine and neramexane |
CN101553217A (zh) | 2005-07-06 | 2009-10-07 | 塞普拉科公司 | 艾司佐匹克隆与反式4-(3,4-二氯苯基)-1,2,3,4-四氢-n-甲基-1-萘胺或反式4-(3,4-二氯苯基)-1,2,3,4-四氢-1-萘胺的组合以及治疗绝经期和心境障碍、焦虑症和认知障碍的方法 |
US8053603B2 (en) | 2006-01-06 | 2011-11-08 | Sunovion Pharmaceuticals Inc. | Tetralone-based monoamine reuptake inhibitors |
CA2636324C (en) | 2006-01-06 | 2012-03-20 | Sepracor Inc. | Cycloalkylamines as monoamine reuptake inhibitors |
CA2648121C (en) | 2006-03-31 | 2013-08-06 | 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 |
JP2010516697A (ja) * | 2007-01-18 | 2010-05-20 | セプラコール インク. | D−アミノ酸オキシダーゼ阻害剤 |
US7902252B2 (en) * | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
KR101581289B1 (ko) | 2007-05-31 | 2015-12-31 | 세프라코 아이엔시. | 모노아민 재흡수 억제제로서 페닐 치환된 시클로알킬아민 |
US20090247644A1 (en) * | 2008-03-28 | 2009-10-01 | Forest Laboratories Holdings Limited | Memantine formulations |
US20100120740A1 (en) * | 2008-08-07 | 2010-05-13 | Sepracor Inc. | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase |
EA201101307A1 (ru) * | 2009-03-10 | 2012-03-30 | Сантен Фармасьютикал Ко., Лтд. | Профилактические или терапевтические средства для расстройств зрительного нерва, содержащие производные 4,6-дихлор-1н-индол-2-карбоновой кислоты или их соли в качестве активных ингредиентов |
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 |
PT3137658T (pt) | 2014-04-30 | 2022-05-05 | Univ Nat Taiwan | Uso de compostos conhecidos como inibidores do d-aminoácido oxidase |
IL307576B1 (en) | 2016-09-14 | 2025-02-01 | Yufeng Jane Tseng | History of new modified benzimidazoles as D-amino acid oxidase (DAAO) inhibitors |
CN110996948A (zh) | 2017-06-12 | 2020-04-10 | 格莱泰施有限责任公司 | 用nmda拮抗剂和d2/5ht2a或选择性5ht2a拮抗剂治疗抑郁症 |
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 |
ES2088011T3 (es) * | 1990-07-16 | 1996-08-01 | Merrell Pharma Inc | Antagonistas de aminoacidos excitadores. |
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 BE BE9300371A patent/BE1006343A5/fr active
- 1993-04-15 US US08/046,947 patent/US5373018A/en not_active Expired - Fee Related
- 1993-04-15 NZ NZ247413A patent/NZ247413A/en unknown
- 1993-04-15 RO RO94-01658A patent/RO113242B1/ro unknown
- 1993-04-15 AU AU36923/93A patent/AU666927B2/en not_active Ceased
- 1993-04-15 GR GR930100154A patent/GR1001619B/el not_active IP Right Cessation
- 1993-04-15 CA CA002094075A patent/CA2094075A1/en not_active Abandoned
- 1993-04-15 CZ CZ942543A patent/CZ285799B6/cs not_active IP Right Cessation
- 1993-04-15 JP JP5517997A patent/JPH07505407A/ja active Pending
- 1993-04-15 DK DK043193A patent/DK169890B1/da active
- 1993-04-15 IT IT93RM000236A patent/IT1265325B1/it active IP Right Grant
- 1993-04-15 CH CH1133/93A patent/CH685630A5/fr 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 RU RU94045915A patent/RU2129544C1/ru active
- 1993-04-15 US US08/047,430 patent/US5374649A/en not_active Expired - Fee Related
- 1993-04-15 SE SE9301241A patent/SE504336C2/sv not_active IP Right Cessation
- 1993-04-15 JP JP5088844A patent/JPH0649027A/ja active Pending
- 1993-04-15 FR FR9304452A patent/FR2690919B1/fr not_active Expired - Fee Related
- 1993-04-15 WO PCT/EP1993/000938 patent/WO1993021153A1/en active IP Right Grant
- 1993-04-15 GB GB9307808A patent/GB2266091B/en not_active Expired - Fee Related
- 1993-04-15 CN CN93105797A patent/CN1042331C/zh not_active Expired - Fee Related
- 1993-04-15 MX MX9302195A patent/MX9302195A/es not_active IP Right Cessation
- 1993-04-15 KR KR1019940703668A patent/KR100264114B1/ko not_active Expired - Fee Related
- 1993-04-15 ES ES09300771A patent/ES2105924B1/es not_active Expired - Lifetime
- 1993-04-15 IS IS3994A patent/IS3994A/is unknown
- 1993-04-15 IL IL105412A patent/IL105412A/en not_active IP Right Cessation
- 1993-04-15 EP EP93201103A patent/EP0568136A1/en not_active Withdrawn
- 1993-04-15 US US08/047,429 patent/US5374648A/en not_active Expired - Fee Related
- 1993-04-15 CA CA002094073A patent/CA2094073A1/en not_active Abandoned
- 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 MY MYPI93000690A patent/MY112232A/en unknown
- 1993-04-15 SK SK1241-94A patent/SK281941B6/sk unknown
- 1993-04-15 CA CA002094076A patent/CA2094076A1/en not_active Abandoned
- 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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