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GB1268243A - 0,2,4,5,-tetrahydro-3h,3-benzazepines - Google Patents

0,2,4,5,-tetrahydro-3h,3-benzazepines

Info

Publication number
GB1268243A
GB1268243A GB1284469A GB1284469A GB1268243A GB 1268243 A GB1268243 A GB 1268243A GB 1284469 A GB1284469 A GB 1284469A GB 1284469 A GB1284469 A GB 1284469A GB 1268243 A GB1268243 A GB 1268243A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
phenyl
lower alkyl
alkyl
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1284469A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
US Filter Wallace and Tiernan Inc
Original Assignee
Wallace and Tiernan Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wallace and Tiernan Inc filed Critical Wallace and Tiernan Inc
Publication of GB1268243A publication Critical patent/GB1268243A/en
Expired legal-status Critical Current

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,268,243. Benzazepine derivatives. WALLACE & TIERNAN Inc. 11 March, 1969 [11 March, 1968], No. 12844/69. Heading C2C. Novel compounds I or the pharmaceutically acceptable addition salts thereof, wherein R is H, lower alkyl, dialkylaminoalkyl; lower alkenyl containing 3-6 carbon atoms; aryl-C 3 -C 6 alkenyl; cycloalkyl-alkyl; aryl-cylcoalkyl-alkyl; propargyl; aryl-lower alkyl, the aryl group selected from phenyl, tolyl, nitrophenyl, aminophenyl, acylaminophenyl, methoxyphenyl, hydroxyphenyl, methylaminophenyl, ethylaminophenyl, or dimethylaminophenyl; a lower alkyl ester of hydroxyalkyl; a heterocyclic group, an alkyl group substituted by a heterocyclic ring (unsubstituted or substituted with one or more phenyl, hydroxyl or acyl groups), 2-phthalimidoethyl- (the phenyl moiety unsubstituted or substituted in any of the remaining positons with NH 2 , OH, OCH 3 , halogen, alkyl); 2-(2- isoindolinyl)-ethyl- (the phenyl moiety unsubstituted or substituted in any of the remaining positions with NH 2 , OH, OCH 3 , halogen, alkyl); 2 - [4 - benzyl - 1 - piperazinyl] - ethyl- (the phenyl moiety unsubstituted or substituted in the o, m, or p-position with NH 2 , OH, OCH 3 ); 2 - (4 - phenyl - 1 - piperazinyl) - ethyl- (the phenyl moiety unsubstituted or substituted in the o, m, p-position with NH 2 , OH, OCH 3 , halogen, alkyl); 2-[4-(o-methylbenzyl)-1-piperazinyl]-ethyl- (the phenyl moiety unsubstituted or substituted in the o, m, or p-position with NH 2 , OH, OCH 3 , halogen, alkyl); R<SP>1</SP> is hydrogen and R<SP>2</SP> is hydrogen, lower alkyl, phenyl or phenyl-lower alkyl, or R<SP>1</SP> and R<SP>2</SP> are lower alkyl; R<SP>3</SP> is hydrogen or lower alkyl; R<SP>4</SP> and R<SP>5</SP> are hydrogen, lower alkoxy, CH 3 OCH 2 O-, hydroxy, pyridine carboxylic acid ester of hydroxy group, amino, lower alkyl, halogen or nitro; R<SP>6</SP> and R<SP>7</SP> are hydrogen, lower alkyl, phenyl or phenylalkyl; R<SP>8</SP> is hydrogen, lower alkyl, phenyl or phenylalkyl; provided that when R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>5</SP>, R<SP>6</SP>, R<SP>7</SP> and R<SP>8</SP> are hydrogen and R is allyl, dialkylaminoalkyl or unsubstituted heterocyclylalkyl, R<SP>4</SP> is hydroxyl; provided that at least one of R<SP>1</SP>, R<SP>2</SP>,R<SP>3</SP>, R<SP>4</SP>, R<SP>5</SP>, R<SP>6</SP>, R<SP>7</SP> and R<SP>8</SP> is other than hydrogen when R is either hydrogen, lower alkyl, allyl or phenyl-lower alkyl; and that neither R<SP>4</SP> nor R<SP>5</SP> is 6-chloro when R, R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>6</SP>, R<SP>7</SP> and R<SP>8</SP> are hydrogen and provided that when R<SP>4</SP> and R<SP>5</SP> are methoxy R is not hydrogen or methyl, are prepared by processes similar to those exemplified in the following sequences The intermediates shown in the above sequences may be isolated. Pharmaceutical compositions comprise the novel compounds above in conjunction with suitable carriers and/or diluents and have analgesic properties and ability to antagonize the action of strong narcotic analgesics. In addition some of the novel compounds exhibit antihistaminic and anticholinergic activity.
GB1284469A 1968-03-11 1969-03-11 0,2,4,5,-tetrahydro-3h,3-benzazepines Expired GB1268243A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US71189768A 1968-03-11 1968-03-11

Publications (1)

Publication Number Publication Date
GB1268243A true GB1268243A (en) 1972-03-22

Family

ID=24859960

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1284469A Expired GB1268243A (en) 1968-03-11 1969-03-11 0,2,4,5,-tetrahydro-3h,3-benzazepines

Country Status (2)

Country Link
CA (1) CA974989A (en)
GB (1) GB1268243A (en)

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005300A1 (en) * 1978-05-08 1979-11-14 Technobiotic Ltd. Substituted 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines, process for the preparation thereof, and pharmaceutical compositions containing them
EP0007070A1 (en) * 1978-07-07 1980-01-23 Smithkline Beckman Corporation 2,3,4,5-Tetrahydro-1H-3-Benzazepines, process for their production and pharmaceutical compositions having dopamine receptor blocking activity
US4284556A (en) * 1980-01-31 1981-08-18 Smithkline Corporation 7,8-Amino, hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines
EP0044709A1 (en) * 1980-07-17 1982-01-27 Smithkline Beckman Corporation New dopaminergic benzazepines
EP0080779A1 (en) * 1981-11-27 1983-06-08 Smithkline Beckman Corporation 3-Benzazepines as alpha-2 antagonists
EP0103961A1 (en) * 1982-07-29 1984-03-28 Smithkline Beckman Corporation Allyloxy- and allylthio-2,3,4,5-tetrahydro-1H-3-benzazepines
EP0108170A1 (en) * 1982-10-08 1984-05-16 Smithkline Beckman Corporation 3-Benzazepines as alpha-2 antagonists
US4496558A (en) * 1981-11-27 1985-01-29 Smithkline Beckman Corporation Pharmaceutical compositions and methods for producing alpha antagonism
WO1985000808A1 (en) * 1983-08-12 1985-02-28 Schering Corp. Benzazepine derivatives, pharmaceutical compositions containing them and processes for the preparation of such compounds and compositions
GB2170197A (en) * 1985-01-17 1986-07-30 Ici Plc Cyclopropane-containing amine compounds
US4659706A (en) * 1985-12-20 1987-04-21 Smithkline Beckman Corporation Sulfinyl and sulfonyl substituted 3-benzazepines
US4707483A (en) * 1985-12-20 1987-11-17 Smithkline Beckman Corporation 1-phenyl-3-benzazepines and their use for treating gastrointestinal motility disorders
EP0284384A1 (en) * 1987-03-25 1988-09-28 Pfizer Limited Anti-arrhythmic agents
WO1988007526A1 (en) * 1987-03-27 1988-10-06 Schering Corporation Substituted benzazepines, their preparation and pharmaceutical compositions containing them
EP0347672A1 (en) * 1988-06-15 1989-12-27 Novo Nordisk A/S Benzazepine derivatives
EP0383247A1 (en) * 1989-02-14 1990-08-22 Novo Nordisk A/S Benzazepines with antidopaminergic activity
US5015639A (en) * 1987-03-27 1991-05-14 Schering Corporation Substituted benzazepines, their preparation and pharmaceutical compositions containing them
WO2002074746A1 (en) * 2001-03-16 2002-09-26 Yamanouchi Pharmaceutical Co., Ltd. Benzazepine derivatives
EP1411881A4 (en) * 2002-04-12 2004-07-07 Arena Pharm Inc 5HT sb 2C /sb RECEPTOR MODULATORS
JP2007521269A (en) * 2003-06-17 2007-08-02 アリーナ ファーマシューティカルズ， インコーポレイテッド Method for preparing 3-benzazepine
EP2133340A1 (en) 2002-12-20 2009-12-16 Glaxo Group Limited Novel benzazepine derivatives
US7704993B2 (en) 2003-06-17 2010-04-27 Arena Pharmaceuticals, Inc. Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases
US8153621B2 (en) 2004-12-23 2012-04-10 Arena Pharmaceuticals, Inc. 5ht2C receptor modulator compositions
US8168624B2 (en) 2004-12-21 2012-05-01 Arena Pharmaceuticals, Inc. Crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
US8168782B2 (en) 2006-04-03 2012-05-01 Arena Pharmaceuticals, Inc. Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates related thereto
US8299241B2 (en) 2006-12-05 2012-10-30 Arena Pharmaceuticals, Inc. Processes for preparing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates thereof
US8822727B2 (en) 2008-03-04 2014-09-02 Arena Pharmaceuticals, Inc. Processes for the preparation of intermediates related to the 5-HT2C agonist (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
US8952197B2 (en) 2009-06-18 2015-02-10 Arena Pharmaceuticals, Inc. Processes for the preparation of 5-HT2C receptor agonists
US8999970B2 (en) 2010-09-01 2015-04-07 Arena Pharmaceuticals, Inc. Administration of an anti-obesity compound to individuals with renal impairment
US9045431B2 (en) 2010-06-02 2015-06-02 Arena Pharmaceuticals, Inc. Processes for the preparation of 5-HT2C receptor agonists
US9169213B2 (en) 2012-10-09 2015-10-27 Arena Pharmaceuticals, Inc. Method of weight management
US9248133B2 (en) 2010-09-01 2016-02-02 Arena Pharmaceuticals, Inc. Salts of lorcaserin with optically active acids
US9365521B2 (en) 2010-09-01 2016-06-14 Arena Pharmaceuticals, Inc. Non-hygroscopic salts of 5-HT2C agonists
US10226471B2 (en) 2010-09-01 2019-03-12 Arena Pharmaceuticals, Inc. Modified-release dosage forms of 5-HT2C agonists useful for weight management

Cited By (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005300A1 (en) * 1978-05-08 1979-11-14 Technobiotic Ltd. Substituted 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines, process for the preparation thereof, and pharmaceutical compositions containing them
EP0007070A1 (en) * 1978-07-07 1980-01-23 Smithkline Beckman Corporation 2,3,4,5-Tetrahydro-1H-3-Benzazepines, process for their production and pharmaceutical compositions having dopamine receptor blocking activity
EP0080012A1 (en) * 1978-07-07 1983-06-01 Smithkline Beckman Corporation 6-Chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, its acid addition salts and its use as an intermediate
US4284556A (en) * 1980-01-31 1981-08-18 Smithkline Corporation 7,8-Amino, hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines
EP0044709A1 (en) * 1980-07-17 1982-01-27 Smithkline Beckman Corporation New dopaminergic benzazepines
US4496558A (en) * 1981-11-27 1985-01-29 Smithkline Beckman Corporation Pharmaceutical compositions and methods for producing alpha antagonism
EP0080779A1 (en) * 1981-11-27 1983-06-08 Smithkline Beckman Corporation 3-Benzazepines as alpha-2 antagonists
EP0103961A1 (en) * 1982-07-29 1984-03-28 Smithkline Beckman Corporation Allyloxy- and allylthio-2,3,4,5-tetrahydro-1H-3-benzazepines
EP0108170A1 (en) * 1982-10-08 1984-05-16 Smithkline Beckman Corporation 3-Benzazepines as alpha-2 antagonists
WO1985000808A1 (en) * 1983-08-12 1985-02-28 Schering Corp. Benzazepine derivatives, pharmaceutical compositions containing them and processes for the preparation of such compounds and compositions
EP0135767A1 (en) * 1983-08-12 1985-04-03 Schering Corporation Benzazepine derivatives, pharmaceutical compositions containing them and processes for the preparation of such compounds and compositions
GB2170197A (en) * 1985-01-17 1986-07-30 Ici Plc Cyclopropane-containing amine compounds
US4659706A (en) * 1985-12-20 1987-04-21 Smithkline Beckman Corporation Sulfinyl and sulfonyl substituted 3-benzazepines
US4707483A (en) * 1985-12-20 1987-11-17 Smithkline Beckman Corporation 1-phenyl-3-benzazepines and their use for treating gastrointestinal motility disorders
US4891372A (en) * 1987-03-25 1990-01-02 Pfizer Inc. Antiarrhythmic agents, compositions and method of use thereas
EP0284384A1 (en) * 1987-03-25 1988-09-28 Pfizer Limited Anti-arrhythmic agents
WO1988007526A1 (en) * 1987-03-27 1988-10-06 Schering Corporation Substituted benzazepines, their preparation and pharmaceutical compositions containing them
EP0285919A1 (en) * 1987-03-27 1988-10-12 Schering Corporation Substituted benzazepines, their preparation and pharmaceutical compositions containing them
US5015639A (en) * 1987-03-27 1991-05-14 Schering Corporation Substituted benzazepines, their preparation and pharmaceutical compositions containing them
EP0347672A1 (en) * 1988-06-15 1989-12-27 Novo Nordisk A/S Benzazepine derivatives
EP0383247A1 (en) * 1989-02-14 1990-08-22 Novo Nordisk A/S Benzazepines with antidopaminergic activity
US5079243A (en) * 1989-02-14 1992-01-07 Novo Nordisk A/S Benzazepines
WO2002074746A1 (en) * 2001-03-16 2002-09-26 Yamanouchi Pharmaceutical Co., Ltd. Benzazepine derivatives
JP2009001584A (en) * 2002-04-12 2009-01-08 Arena Pharmaceuticals Inc 5ht2c receptor modulator
US8846906B2 (en) 2002-04-12 2014-09-30 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
US6953787B2 (en) 2002-04-12 2005-10-11 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
US8993750B2 (en) 2002-04-12 2015-03-31 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
EP1411881A4 (en) * 2002-04-12 2004-07-07 Arena Pharm Inc 5HT sb 2C /sb RECEPTOR MODULATORS
US7514422B2 (en) 2002-04-12 2009-04-07 Arena Pharmaceuticals, Inc. 5HT2c receptor modulators
CN100486967C (en) * 2002-04-12 2009-05-13 阿伦纳药品公司 5HT2c receptor modulators
EP1557409A1 (en) * 2002-04-12 2005-07-27 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
US8575149B2 (en) 2002-04-12 2013-11-05 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
US8546379B2 (en) 2002-04-12 2013-10-01 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
US8273734B1 (en) 2002-04-12 2012-09-25 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
US8207158B2 (en) 2002-04-12 2012-06-26 Arena Pharmaceuticals, Inc. 5HT2c receptor modulators
JP2012006970A (en) * 2002-04-12 2012-01-12 Arena Pharmaceuticals Inc 5ht2c receptor modulators
US7977329B2 (en) 2002-04-12 2011-07-12 Arena Pharmaceuticals, Inc. 5HT2C receptor modulators
EP2363394A1 (en) * 2002-04-12 2011-09-07 Arena Pharmaceuticals, Inc. 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, its salts, solvates or hydrates and its use for the treatment of CNS disorders
EP2374796A1 (en) * 2002-04-12 2011-10-12 Arena Pharmaceuticals, Inc. 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, its salts, solvates or hydrates and its use for the treatment of CNS disorders
US7799773B2 (en) 2002-12-20 2010-09-21 Glaxo Group Limited Benzazepine derivatives for the treatment of neurological disorders
US7696193B2 (en) 2002-12-20 2010-04-13 Glaxo Group Limited Benzazepine derivatives for the treatment of neurological disorders
EP2186516A1 (en) 2002-12-20 2010-05-19 Glaxo Group Limited Novel benzazepine derivative
US8207331B2 (en) 2002-12-20 2012-06-26 Glaxo Group Limited Benzazepine derivatives for the treatment of neurological disorders
EP2133340A1 (en) 2002-12-20 2009-12-16 Glaxo Group Limited Novel benzazepine derivatives
US7704994B2 (en) 2002-12-20 2010-04-27 Glaxo Group Limited Benzazepine derivatives for the treatment of neurological disorders
JP4920409B2 (en) * 2003-06-17 2012-04-18 アリーナ ファーマシューティカルズ， インコーポレイテッド Method for preparing 3-benzazepine
US9102627B2 (en) 2003-06-17 2015-08-11 Arena Pharmaceuticals, Inc. Processes for preparing 3-benzazepines
JP2007521269A (en) * 2003-06-17 2007-08-02 アリーナ ファーマシューティカルズ， インコーポレイテッド Method for preparing 3-benzazepine
US7704993B2 (en) 2003-06-17 2010-04-27 Arena Pharmaceuticals, Inc. Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases
US8946207B2 (en) 2003-06-17 2015-02-03 Arena Pharmaceuticals, Inc. Processes for preparing 3-benzazepines
US8367657B2 (en) 2003-06-17 2013-02-05 Arena Pharmaceuticals, Inc. Processes for preparing 3-benzazepines
US8404675B2 (en) 2003-06-17 2013-03-26 Arena Pharmaceuticals, Inc. Benzazepine derivatives and methods of prophylaxis or treatment of 5HT2C receptor associated diseases
US8697686B2 (en) 2004-12-21 2014-04-15 Arena Pharmaceuticals, Inc. Crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-thtrahydro-1H-3-benzazepine hydrochloride
US8980881B2 (en) 2004-12-21 2015-03-17 Arena Pharmaceuticals, Inc. Crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
US8168624B2 (en) 2004-12-21 2012-05-01 Arena Pharmaceuticals, Inc. Crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
US8153621B2 (en) 2004-12-23 2012-04-10 Arena Pharmaceuticals, Inc. 5ht2C receptor modulator compositions
US8546378B2 (en) 2004-12-23 2013-10-01 Arena Pharmaceuticals, Inc. 5HT2C receptor modulator compositions and methods of use
US8168782B2 (en) 2006-04-03 2012-05-01 Arena Pharmaceuticals, Inc. Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates related thereto
US8802845B2 (en) 2006-04-03 2014-08-12 Arena Phamaceuticals, Inc. Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates related thereto
US8501935B2 (en) 2006-04-03 2013-08-06 Arena Pharmaceuticals, Inc. Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates related thereto
US8299241B2 (en) 2006-12-05 2012-10-30 Arena Pharmaceuticals, Inc. Processes for preparing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates thereof
US8822727B2 (en) 2008-03-04 2014-09-02 Arena Pharmaceuticals, Inc. Processes for the preparation of intermediates related to the 5-HT2C agonist (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
US8952197B2 (en) 2009-06-18 2015-02-10 Arena Pharmaceuticals, Inc. Processes for the preparation of 5-HT2C receptor agonists
US9045431B2 (en) 2010-06-02 2015-06-02 Arena Pharmaceuticals, Inc. Processes for the preparation of 5-HT2C receptor agonists
US8999970B2 (en) 2010-09-01 2015-04-07 Arena Pharmaceuticals, Inc. Administration of an anti-obesity compound to individuals with renal impairment
US9248133B2 (en) 2010-09-01 2016-02-02 Arena Pharmaceuticals, Inc. Salts of lorcaserin with optically active acids
US9365521B2 (en) 2010-09-01 2016-06-14 Arena Pharmaceuticals, Inc. Non-hygroscopic salts of 5-HT2C agonists
US9770455B2 (en) 2010-09-01 2017-09-26 Arena Pharmaceuticals, Inc. Administration of an anti-obesity compound to individuals with renal impairment
US10226471B2 (en) 2010-09-01 2019-03-12 Arena Pharmaceuticals, Inc. Modified-release dosage forms of 5-HT2C agonists useful for weight management
US10463676B2 (en) 2010-09-01 2019-11-05 Arena Pharmaceuticals, Inc. Modified-release dosage forms of 5-HT2C agonists useful for weight management
US9169213B2 (en) 2012-10-09 2015-10-27 Arena Pharmaceuticals, Inc. Method of weight management

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