Patent GB-1268243-A (GB)
Title: 0,2,4,5,-tetrahydro-3h,3-benzazepines
IPC: C07D223/16
Filed: 1969-03-11
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.