GB1043859A - Novel phenanthrene derivatives and a process for the manufacture thereof - Google Patents

Abstract

Novel compounds of the formula <FORM:1043859/C2/1> wherein R represents hydrogen, an alkyl, alkenyl or alkynyl group of up to 5 carbon atoms or an acyl group, and Z is a cyclo alkyl radical which includes a C3-C6 cyclo alkyl ring and contains at least 4C atoms where it partly consists of a cyclopropyl ring or at least 5C atoms where it partly consists of a cyclo butyl ring, are prepared by reacting compounds of the formula <FORM:1043859/C2/2> with an appropriate acid derivative such as a halide, anhydride or ester of a cycloalkane carboxylic acid and reducing the carbonyl group of the resulting morphinan of formula <FORM:1043859/C2/3> to a methylene group. Alternatively, the same compounds may be condensed with a halide of the formula Hal-CH2-Z. The product may be converted into an ether or ester and/or an acid addition salt. The end products may have a morphinan or isomorphinan structure and may be obtained as racemic mixtures or in optically active form of which the (-) forms are preferred. Pharmaceutical compositions having analgesic and antitussive activity and exhibiting an antagonistic action against the side effects of morphine contain as active ingredients compounds of the first above general formula. The compounds may be used in tablets, dragees, suppositories, capsules or in liquid form and may be used for enteral or parenteral application.