NO309323B1 - Indolderivater, anvendelse derav og farmasöytisk preparat - Google Patents
Indolderivater, anvendelse derav og farmasöytisk preparat Download PDFInfo
- Publication number
- NO309323B1 NO309323B1 NO974043A NO974043A NO309323B1 NO 309323 B1 NO309323 B1 NO 309323B1 NO 974043 A NO974043 A NO 974043A NO 974043 A NO974043 A NO 974043A NO 309323 B1 NO309323 B1 NO 309323B1
- Authority
- NO
- Norway
- Prior art keywords
- solution
- stirred
- indole
- dichloro
- ethenyl
- Prior art date
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 150000002475 indoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 174
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- -1 methoxy, 3-pyridyl Chemical group 0.000 claims description 26
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
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- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 230000003042 antagnostic effect Effects 0.000 claims description 3
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- 230000002461 excitatory amino acid Effects 0.000 claims description 3
- 239000003257 excitatory amino acid Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
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- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
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- 239000000543 intermediate Substances 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
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- 239000000203 mixture Substances 0.000 description 18
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 17
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 17
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 17
- 238000000034 method Methods 0.000 description 17
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- 125000006239 protecting group Chemical group 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
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- 239000003480 eluent Substances 0.000 description 7
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- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 6
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
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- 230000004770 neurodegeneration Effects 0.000 description 5
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 5
- 230000003389 potentiating effect Effects 0.000 description 5
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- 229920002554 vinyl polymer Polymers 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9504361.8A GB9504361D0 (en) | 1995-03-04 | 1995-03-04 | Heterocyclic compounds |
| PCT/EP1996/000840 WO1996027588A1 (fr) | 1995-03-04 | 1996-03-01 | Derives de l'indole utilises comme antagonistes d'acides amines excitateurs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO974043D0 NO974043D0 (no) | 1997-09-03 |
| NO974043L NO974043L (no) | 1997-11-03 |
| NO309323B1 true NO309323B1 (no) | 2001-01-15 |
Family
ID=10770638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO974043A NO309323B1 (no) | 1995-03-04 | 1997-09-03 | Indolderivater, anvendelse derav og farmasöytisk preparat |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5919811A (fr) |
| EP (1) | EP0813524A1 (fr) |
| JP (1) | JPH11501041A (fr) |
| KR (1) | KR19980702735A (fr) |
| CN (1) | CN1182417A (fr) |
| AR (1) | AR002711A1 (fr) |
| AU (1) | AU708291B2 (fr) |
| BR (1) | BR9607346A (fr) |
| CA (1) | CA2214583A1 (fr) |
| CO (1) | CO4700452A1 (fr) |
| CZ (1) | CZ277997A3 (fr) |
| EA (1) | EA000308B1 (fr) |
| GB (1) | GB9504361D0 (fr) |
| HU (1) | HUP9801838A3 (fr) |
| IL (1) | IL117331A (fr) |
| MX (1) | MX9706605A (fr) |
| NO (1) | NO309323B1 (fr) |
| NZ (1) | NZ303200A (fr) |
| PE (1) | PE62396A1 (fr) |
| PL (1) | PL322084A1 (fr) |
| TW (1) | TW438773B (fr) |
| WO (1) | WO1996027588A1 (fr) |
| ZA (1) | ZA961697B (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5886191A (en) * | 1997-08-18 | 1999-03-23 | Dupont Pharmaceuticals Company | Amidinoindoles, amidinoazoles, and analogs thereof |
| GB9902455D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| PL373484A1 (en) * | 2001-12-10 | 2005-09-05 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| GB0205176D0 (en) * | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| WO2004064730A2 (fr) * | 2003-01-14 | 2004-08-05 | Cytokinetics, Inc. | Composes, compositions et procedes |
| MXPA06014495A (es) * | 2004-06-17 | 2007-03-01 | Cytokinetics Inc | Compuestos, composiciones y metodos. |
| US7176222B2 (en) | 2004-07-27 | 2007-02-13 | Cytokinetics, Inc. | Syntheses of ureas |
| US7538223B2 (en) * | 2005-08-04 | 2009-05-26 | Cytokinetics, Inc. | Compounds, compositions and methods |
| US7825120B2 (en) * | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| ES2419007T3 (es) | 2005-12-15 | 2013-08-19 | Cytokinetics, Inc. | Ciertas entidades químicas, composiciones y procedimientos |
| US20070208000A1 (en) * | 2005-12-15 | 2007-09-06 | Morgan Bradley P | Certain chemical entities, compositions and methods |
| WO2007075377A2 (fr) * | 2005-12-15 | 2007-07-05 | Cytokinetics, Inc. | Entites chimiques, compositions et procedes |
| EP1959962A2 (fr) * | 2005-12-16 | 2008-08-27 | Cytokinetics, Inc. | Entites chimiques, compositions et methodes |
| JP5178526B2 (ja) * | 2005-12-19 | 2013-04-10 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
| WO2009035927A2 (fr) * | 2007-09-13 | 2009-03-19 | Arete Therapeutics, Inc. | Inhibiteurs de l'époxyde hydrolase soluble |
| PE20091101A1 (es) | 2007-12-18 | 2009-07-26 | Pharminox Ltd | AMIDAS DE ACIDO 3-SUBSTITUIDO-4-OXO-3,4-DIHIDRO-IMIDAZO[5,1-d] [1,2,3,5-TETRACINA-8-CARBOXILICO Y SU EMPLEO |
| ES2583006T3 (es) | 2009-06-23 | 2016-09-16 | Pharminox Limited | Compuestos de 3-sustituido-8-sustituido-3H-imidazo[5,1-d][1,2,3,5-tetrazin-4-ona y su uso |
| WO2011107726A1 (fr) | 2010-03-01 | 2011-09-09 | Pharminox Ltd | Procédés et intermédiaires pour effectuer la synthèse de 4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tétrazines |
| WO2012085501A1 (fr) | 2010-12-20 | 2012-06-28 | Pharminox Limited | Composés 8-sulfo-imidazotétrazin-4-one et leur utilisation en tant que médicament anticancéreux |
| TW202128630A (zh) | 2019-11-11 | 2021-08-01 | 荷蘭商卡普三世責任有限公司 | 工業規模上用於生產ε-己內醯胺及硫酸銨之方法及設備 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5145845A (en) * | 1991-05-14 | 1992-09-08 | Warner-Lambert Co. | Substituted 2-carboxylindoles having pharmaceutical activity |
| GB9208492D0 (en) * | 1992-04-16 | 1992-06-03 | Glaxo Spa | Heterocyclic compounds |
| 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 |
-
1995
- 1995-03-04 GB GBGB9504361.8A patent/GB9504361D0/en active Pending
-
1996
- 1996-03-01 CZ CZ972779A patent/CZ277997A3/cs unknown
- 1996-03-01 BR BR9607346A patent/BR9607346A/pt unknown
- 1996-03-01 EP EP96905833A patent/EP0813524A1/fr not_active Withdrawn
- 1996-03-01 PE PE1996000145A patent/PE62396A1/es not_active Application Discontinuation
- 1996-03-01 MX MX9706605A patent/MX9706605A/es unknown
- 1996-03-01 JP JP8526590A patent/JPH11501041A/ja active Pending
- 1996-03-01 WO PCT/EP1996/000840 patent/WO1996027588A1/fr not_active Application Discontinuation
- 1996-03-01 KR KR1019970706142A patent/KR19980702735A/ko not_active Application Discontinuation
- 1996-03-01 AR ARP960101610A patent/AR002711A1/es unknown
- 1996-03-01 AU AU49438/96A patent/AU708291B2/en not_active Ceased
- 1996-03-01 CO CO96009937A patent/CO4700452A1/es unknown
- 1996-03-01 CN CN96193467A patent/CN1182417A/zh active Pending
- 1996-03-01 IL IL11733196A patent/IL117331A/xx not_active IP Right Cessation
- 1996-03-01 HU HU9801838A patent/HUP9801838A3/hu unknown
- 1996-03-01 EA EA199700160A patent/EA000308B1/ru not_active IP Right Cessation
- 1996-03-01 ZA ZA9601697A patent/ZA961697B/xx unknown
- 1996-03-01 US US08/894,702 patent/US5919811A/en not_active Expired - Fee Related
- 1996-03-01 PL PL96322084A patent/PL322084A1/xx unknown
- 1996-03-01 NZ NZ303200A patent/NZ303200A/xx unknown
- 1996-03-01 CA CA002214583A patent/CA2214583A1/fr not_active Abandoned
- 1996-03-19 TW TW085103238A patent/TW438773B/zh active
-
1997
- 1997-09-03 NO NO974043A patent/NO309323B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MX9706605A (es) | 1998-02-28 |
| IL117331A0 (en) | 1996-07-23 |
| NO974043L (no) | 1997-11-03 |
| HUP9801838A3 (en) | 2000-04-28 |
| EA000308B1 (ru) | 1999-04-29 |
| CO4700452A1 (es) | 1998-12-29 |
| NO974043D0 (no) | 1997-09-03 |
| HUP9801838A2 (hu) | 1998-12-28 |
| BR9607346A (pt) | 1997-12-30 |
| JPH11501041A (ja) | 1999-01-26 |
| CZ277997A3 (cs) | 1998-06-17 |
| AU708291B2 (en) | 1999-07-29 |
| PE62396A1 (es) | 1997-01-11 |
| EP0813524A1 (fr) | 1997-12-29 |
| NZ303200A (en) | 1999-01-28 |
| AU4943896A (en) | 1996-09-23 |
| AR002711A1 (es) | 1998-04-29 |
| ZA961697B (en) | 1997-10-01 |
| PL322084A1 (en) | 1998-01-05 |
| US5919811A (en) | 1999-07-06 |
| WO1996027588A1 (fr) | 1996-09-12 |
| CA2214583A1 (fr) | 1996-09-12 |
| GB9504361D0 (en) | 1995-04-26 |
| CN1182417A (zh) | 1998-05-20 |
| KR19980702735A (ko) | 1998-08-05 |
| IL117331A (en) | 2000-06-29 |
| TW438773B (en) | 2001-06-07 |
| EA199700160A1 (ru) | 1998-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN SEPTEMBER 2002 |