Analgesic and morphine-antagonistic 9-phenyl-6,7-benzomorphans

Details Analgesic and morphine-antagonistic 9-phenyl-6,7-benzomorphans Analgesic and morphine-antagonistic 9-phenyl-6,7-benzomorphans

1979-05-04

1980-11-18

Jiles, Henry R.

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Parasitic organism or component thereof or substance...

546 97, A61K 31445, C07D22126

Patent

active

042345910

ABSTRACT:
The invention is concerned with certain new 6,7-benzomorphan derivatives having pharmacological, in particular analgesic and/or morphine-antagonistic properties, of the formula ##STR1## wherein R.sup.1 is a substituted or unsubstituted phenyl or heteroaryl group; R.sup.2 is a hydrogen or halogen atom, or a hydroxy, alkoxy or acyloxy group; R.sup.3 is an alkyl or alkenyl group; R.sup.4 is a hydrogen atom or a hydroxy, alkoxy or acyloxy group; and R.sup.5 is an alkyl group or, when R.sup.2 is hydrogen in a trans-position to R.sup.3, R.sup.5 is a hydrogen atom or an alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, cycloalkenylalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, or a substituted or unsubstituted phenylalkyl, heteroarylalkyl or heterocycloalkylalkyl group; optical isomers and pharmaceutically acceptable sals thereof.
The preferred compound is the .alpha.-isomer of 2,5-dimethyl- 2'-hydroxy-9-phenyl-6,7-benzomorphan, in particular its (+)-enantiomer.
These compounds are prepared by total synthesis and are not derived from opium alkaloids.

REFERENCES:
patent: 3320265 (1967-05-01), Clarke
patent: 3511846 (1970-05-01), Munch
patent: 3639407 (1972-02-01), Clarke et al.
patent: 3932422 (1976-01-01), Michne
Eddy, N., et al., J. Org. Chem., 22, 1370 (1957).

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