NO300497B1 - Analogifremgangsmåte for fremstilling av terapeutisk aktive benzazepin-forbindelser - Google Patents
Analogifremgangsmåte for fremstilling av terapeutisk aktive benzazepin-forbindelser Download PDFInfo
- Publication number
- NO300497B1 NO300497B1 NO923413A NO923413A NO300497B1 NO 300497 B1 NO300497 B1 NO 300497B1 NO 923413 A NO923413 A NO 923413A NO 923413 A NO923413 A NO 923413A NO 300497 B1 NO300497 B1 NO 300497B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- hydroxy
- benz
- azepine
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 4
- 150000008038 benzoazepines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
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- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- -1 alkyl enol ether Chemical class 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 6
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 208000033300 perinatal asphyxia Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- 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
- A61P25/28—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
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919100028A GB9100028D0 (en) | 1991-01-02 | 1991-01-02 | Compounds |
| PCT/GB1991/002326 WO1992011854A1 (en) | 1991-01-02 | 1991-12-30 | Therapeutic benzazepine compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO923413L NO923413L (no) | 1992-09-01 |
| NO923413D0 NO923413D0 (no) | 1992-09-01 |
| NO300497B1 true NO300497B1 (no) | 1997-06-09 |
Family
ID=10687882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO923413A NO300497B1 (no) | 1991-01-02 | 1992-09-01 | Analogifremgangsmåte for fremstilling av terapeutisk aktive benzazepin-forbindelser |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US5254683A (es) |
| EP (1) | EP0517876B1 (es) |
| JP (1) | JP3034604B2 (es) |
| KR (1) | KR100229049B1 (es) |
| AT (1) | ATE144423T1 (es) |
| AU (1) | AU650086B2 (es) |
| CA (1) | CA2058593A1 (es) |
| CZ (1) | CZ299292A3 (es) |
| DE (1) | DE69122858T2 (es) |
| DK (1) | DK0517876T3 (es) |
| ES (1) | ES2093246T3 (es) |
| FI (1) | FI104071B1 (es) |
| GB (2) | GB9100028D0 (es) |
| GR (1) | GR3021440T3 (es) |
| HU (2) | HU212269B (es) |
| IE (1) | IE920009A1 (es) |
| IL (1) | IL100484A (es) |
| NO (1) | NO300497B1 (es) |
| NZ (1) | NZ241197A (es) |
| PL (1) | PL166481B1 (es) |
| WO (1) | WO1992011854A1 (es) |
| ZA (1) | ZA9223B (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9100028D0 (en) * | 1991-01-02 | 1991-02-20 | Ici Plc | Compounds |
| GB9212308D0 (en) * | 1992-06-10 | 1992-07-22 | Ici Plc | Therapeutic compositions |
| ATE404201T1 (de) * | 1992-06-22 | 2008-08-15 | Univ California | Glycinrezeptorantagonisten und ihre verwendung |
| CA2115792C (en) | 1993-03-05 | 2005-11-01 | David J. Mayer | Method for the treatment of pain |
| US5834479A (en) * | 1993-03-05 | 1998-11-10 | Mayer; David J. | Method and composition for alleviating pain |
| GB9311948D0 (en) * | 1993-06-10 | 1993-07-28 | Zeneca Ltd | Substituted nitrogen heterocycles |
| US5801168A (en) * | 1994-06-09 | 1998-09-01 | Zeneca Limited | Substituted nitrogen heterocycles |
| US5476933A (en) * | 1994-11-16 | 1995-12-19 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Azepine synthesis via a diels-alder reaction |
| FR2796552A1 (fr) * | 1999-07-21 | 2001-01-26 | Centre Nat Rech Scient | Nouvelle utilisation de derives de la beta-naphtoquinone et de leurs sels pour la fabrication de medicaments exercant un effet inhibiteur sur la liberation de glutamate dans le cerveau |
| JP4989830B2 (ja) * | 1999-07-21 | 2012-08-01 | サーントゥル ナシオナル ドゥ ラ ルシェルシュ シャーンティフィク | 脳によるグルタミン酸塩の放出に対して抑制効果を示す薬剤を製造するためのベータ−ナフトキノン誘導体の使用 |
| JPWO2016199789A1 (ja) * | 2015-06-08 | 2018-03-29 | 国立大学法人名古屋大学 | トリフルオロメチル置換セミスクアレートの製造方法、トリフルオロメチル置換セミスクアレートを起点とするトリフルオロメチル化合物の製造方法及びトリフルオロメチル基含有化合物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1340334A (en) * | 1970-07-06 | 1973-12-12 | Rees A H | Synthesis of benzazetropolones and hence of kynurenic acids |
| GB2103614B (en) * | 1981-08-11 | 1984-11-21 | Ciba Geigy Ag | Benzazepin-2-ones |
| US4410520A (en) * | 1981-11-09 | 1983-10-18 | Ciba-Geigy Corporation | 3-Amino-[1]-benzazepin-2-one-1-alkanoic acids |
| US4473575A (en) * | 1982-07-19 | 1984-09-25 | Ciba-Geigy Corporation | 3-Amino-(1)-benzazepin-2-one-1-alkanoic acids |
| US4575503A (en) * | 1983-02-10 | 1986-03-11 | Ciba-Geigy Corporation | 3-Amino-[1]-benzazepin-2-one-1-alkanoic acids |
| US4477446A (en) * | 1983-07-01 | 1984-10-16 | Usv Pharmaceutical Corporation | 1-Benzazepines and their pharmaceutical uses |
| DE3416695A1 (de) * | 1984-05-05 | 1985-11-07 | Bayer Ag, 5090 Leverkusen | Amidinohydrazone von tetralin-, chromon-, thiochromon- und tretrahydrochinolin-derivaten, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| EP0450097B1 (en) * | 1989-10-20 | 1996-04-24 | Otsuka Pharmaceutical Co., Ltd. | Benzoheterocyclic compounds |
| GB9100028D0 (en) * | 1991-01-02 | 1991-02-20 | Ici Plc | Compounds |
| ATE404201T1 (de) * | 1992-06-22 | 2008-08-15 | Univ California | Glycinrezeptorantagonisten und ihre verwendung |
-
1991
- 1991-01-02 GB GB919100028A patent/GB9100028D0/en active Pending
- 1991-12-24 IL IL10048491A patent/IL100484A/xx not_active IP Right Cessation
- 1991-12-30 CA CA002058593A patent/CA2058593A1/en not_active Abandoned
- 1991-12-30 HU HU9202618A patent/HU212269B/hu unknown
- 1991-12-30 AT AT92901758T patent/ATE144423T1/de not_active IP Right Cessation
- 1991-12-30 DE DE69122858T patent/DE69122858T2/de not_active Expired - Fee Related
- 1991-12-30 KR KR1019920702119A patent/KR100229049B1/ko not_active IP Right Cessation
- 1991-12-30 JP JP04502158A patent/JP3034604B2/ja not_active Expired - Fee Related
- 1991-12-30 DK DK92901758.0T patent/DK0517876T3/da active
- 1991-12-30 AU AU91340/91A patent/AU650086B2/en not_active Ceased
- 1991-12-30 GB GB9127498A patent/GB2251616B/en not_active Expired - Fee Related
- 1991-12-30 PL PL91295932A patent/PL166481B1/pl unknown
- 1991-12-30 ES ES92901758T patent/ES2093246T3/es not_active Expired - Lifetime
- 1991-12-30 WO PCT/GB1991/002326 patent/WO1992011854A1/en active IP Right Grant
- 1991-12-30 EP EP92901758A patent/EP0517876B1/en not_active Expired - Lifetime
- 1991-12-31 US US07/816,327 patent/US5254683A/en not_active Expired - Fee Related
-
1992
- 1992-01-02 IE IE000992A patent/IE920009A1/en not_active IP Right Cessation
- 1992-01-02 ZA ZA9223A patent/ZA9223B/xx unknown
- 1992-01-06 NZ NZ241197A patent/NZ241197A/en unknown
- 1992-08-20 FI FI923759A patent/FI104071B1/fi active
- 1992-09-01 NO NO923413A patent/NO300497B1/no not_active IP Right Cessation
- 1992-09-30 CZ CS922992A patent/CZ299292A3/cs unknown
-
1993
- 1993-07-23 US US08/096,795 patent/US5446039A/en not_active Expired - Lifetime
-
1995
- 1995-05-01 US US08/431,809 patent/US5541319A/en not_active Expired - Fee Related
- 1995-06-26 HU HU95P/P00441P patent/HU211466A9/hu unknown
-
1996
- 1996-10-24 GR GR960402536T patent/GR3021440T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN JUNE 2002 |