Testosterone 5α-reductase inhibitors

Claim 5

The method of claim 2 wherein the compound is administered as a topical preparation containing from 0.001% to 5% of the compound.

Claim 6

The method of claim 2 wherein the compound is administered as a topical preparation containing from 0.005% to 1% of the compound.

Claim 7

The method of claim 2 wherein R 1 is --COOR 2 .

Claim 8

The method of claim 5 wherein n is the integer 0.

Claim 9

The method of claim 6 wherein R 2 is hydrogen.

Claim 10

The method of claim 6 wherein R 2 is methyl.

Claim 11

The method of claim 2 wherein R 1 is --CH 2 OR 5 , and R 5 is hydrogen.

Claim 12

The method of claim 2 wherein R 1 is --CHO.

Claim 13

An anti-acne and anti-seborrheic pharmaceutical composition in the form of an ointment, cream or, paste, for topical administration comprising an anti-acne effective amount of a compound of the formula: ##STR19## wherein n is an integer of from 0 to 4; R 1 is --COOR 2 , --CONR 3 R 4 , --CHO or --CH 2 OR 5 ; R 2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, or benzyl; each of R 3 and R 4 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms; and R 5 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 20 carbon atoms and is straight or branched, benzoyl, phenylalkylcarbonyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched, or cycloalkylcarbonyl wherein the cycloalkyl moiety has from 5 to 10 carbon atoms.

Claim 14

An anti-acne and anti-seborrheic pharmaceutical composition in the form of an ointment, cream or, paste, for topical administration comprising an anti-acne effective amount of a compound of the formula: ##STR19## wherein n is an integer of from 0 to 4; R 1 is --COOR 2 , --CONR 3 R 4 , --CHO or --CH 2 OR 5 ; R 2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, or benzyl; each of R 3 and R 4 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms; and R 5 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 20 carbon atoms and is straight or branched, benzoyl, phenylalkylcarbonyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched, or cycloalkylcarbonyl wherein the cycloalkyl moiety has from 5 to 10 carbon atoms.

Claim 15

A process for preparing a compound of the formula: ##STR20## wherein n is an integer of from 0 to 4 and R 8 is --CONR 10 R 11 or --CH 2 OR 12 wherein each of R 10 and R 11 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms, and R 12 is alkylcarbonyl wherein the alkyl moiety has from 1 to 20 carbon atoms and is straight or branched, benzoyl, phenylalkylcarbonyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched or cycloalkylcarbonyl wherein the cycloalkyl moiety has from 5 to 10 carbon atoms which comprises the steps of when R 8 is --CONR 10 R 11 treating one equivalent of the corresponding acid with one equivalent of a tertiary amine in an ether solvent cooled to -5° to -25° C, adding one equivalent of a mixed anhydride selected from sec-butyl chlorocarbonate or ethyl chlorocarbonate and pivaloyl chloride, stirring the mixture for from 1/2 hour to 2 hours at a temperature of from -5° to -25° C slowly adding with stirring a solution of 2 equivalents of a primary or secondary alkyl amine of the formula --NR 10 R 11 wherein R 10 and R 11 have the meanings defined in claim 1 except both are not hydrogen in an ether, or bubbling ammonia into the reaction mixture and stirring for 1 hour at from -5° to -25° C and for 2 hours at about 25° C afterwhich the reaction mixture is poured into water and the product collected and when R 8 is --CH 2 OR 12 reacting the corresponding alcohol with an acid anhydride of the formula ##STR21## or an acid halide of the formula ##STR22## wherein R 12 has the meaning defined above and halo is chlorine or bromine in the presence of a tertiary amine base for from 1 to 24 hours at a temperature of from about 25° C to 100° C.