GB1319785A - Hexahydroazepines - Google Patents

Abstract

1319785 Hexahydro-1N-azepines JOHN WYETH & BRO Ltd 19 April 1971 [6 Feb 1970] 5804/70 Addition to 1285025 Heading C2C Novel optical isomers of hexahydro-1H- azepines of the general formula wherein R<SP>1</SP> is H, lower alkyl, benzyl or lower alkanoyl, R<SP>2</SP> is lower alkyl, R<SP>3</SP> is H, lower alkyl, lower alkenyl, lower alkynyl, cyclopropylmethyl, lower alkanoyl, lower alkoxycarbonyl, formyl, phenacyl or phenethyl both of which may be substituted on the benzene ring, #- benzoylethyl which may be substituted on the benzene ring (the term lower means a radical containing up to 6 carbon atoms) and the preparation thereof and of acid addition and quaternary salts thereof by resolving a racemic compound of the above formula, or a racemic precursor therefor, by a standard method and, if necessary, converting an obtained optically active isomer to the desired compound by a method known per se such as, when R<SP>1</SP> and R<SP>3</SP> are both H, alkylation, acylation, formylation and reduction or, when R<SP>1</SP> or R<SP>3</SP> is other than the group desired, alkylation, acylation, hydrolysis, hydrogenolysis, formylation or reduction. The preparations of (+) - and (-) - 1-cyclopropylcarbonyl - 3 - ethyl - 3 - (m - hydroxyphenyl)-hexahydro-1H-azepine are also described. Pharmaceutical compositions useful as analgesics contain the above novel optical isomers and a solid, liquid or cream-like carrier and may be in the form of a tablet, capsule or solution. Suitable excipients are starch, milk, sugar or injectable liquids which may also contain saline or glucose.