1-Phenyl-3-azabicyclo[3.1.0]hexanes
AssigneeAmerican Cyanamid Company
InventorsWilliam J. Fanshawe, Joseph W. Epstein, Lantz S. Crawley, Corris M. Hofmann, Sidney R. Safir
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Abstract
Substituted 3-azabicyclo[3.1.0]hexanes, acid addition salts, method of use and method of preparation are described. The compounds have anxiolytic and analgesic activity.
Claims29
An optically active compound of the formula:
- ##STR46## wherein the phenyl moiety is mono-substituted from the group consisting of C.sub.1 -C.sub.6 alkoxy, amino, acetamido and hydroxy;
- X is selected from the group consisting of hydrogen, straight chain C.sub.1 -C.sub.8 alkyl, and a moiety of the formula C.sub.n H.sub.2n R.sub.1, wherein n is an integer from 1 to 3 and R.sub.1 is selected from the group consisting of phenyl and p-fluorobenzoyl;
- the racemic mixture thereof;
- the mirror image thereof;
- and the non-toxic pharmaceutically acceptable salts thereof.
The compound 3-[3-(p-Fluorobenzoyl)propyl]-1-phenyl-3-azabicyclo[3.1.0]hexane hydrochloride.
An optically active compound of the formula:
- ##STR47## wherein the phenyl moiety is mono-substituted from the group consisting of C.sub.1 -C.sub.6 alkoxy methyl, X is selected from the group consisting of hydrogen, straight chain C.sub.1 -C.sub.8 alkyl, and a moiety of the formula C.sub.n H.sub.2n R.sub.1, wherein n is an integer from 1 to 3 and R.sub.1 is selected from the group consisting of halophenyl and bis-halophenyl;
- the racemic mixture thereof;
- the mirror image thereof;
- and the non-toxic pharmaceutically acceptable salts thereof.
An optically active compound of the formula:
- ##STR48## wherein the phenyl moiety is mono-substituted from the group consisting of C.sub.1 -C.sub.6 alkoxy, amino, acetamido and hydroxy;
- X is selected from the group consisting of C.sub.3 -C.sub.6 cycloalkylmethyl, C.sub.3 -C.sub.6 alkenyl and C.sub.3 -C.sub.6 alkynyl;
- the racemic mixture thereof;
- the mirror image thereof;
- and the non-toxic pharmaceutically acceptable salts thereof.
The compound 3-(n-hexyl)-(m-hydroxyphenyl)-3-azabicyclo[3.1.0]hexane.
The compound 1-(m-hydroxyphenyl)-3-(n-pentyl)-3-azabicyclo[3.1.0]hexane.
An optically active compound of the formula:
- ##STR49##
The compound 1-(3-bromo-4-methoxyphenyl)-3-azabicyclo[3.1.0]hexane hydrochloride.
Dependencies are inferred from the claim text.