Benzo F! quinolinones
AssigneeEli Lilly and Company
InventorsJames E. Audia, Kenneth S. Hirsch, Charles D. Jones, David E. Lawhorn, Loretta A. McQuaid, Leland O. Weigel
Life of this patent
Estimating the term…
Abstract
This invention relates to hexa- and octaahydrobenzof!quinolin-3-ones, pharmaceutical formulations containing those compounds and methods of their use as steroid 5.alpha.-reductase inhibitors.
Claims8
A method of treating acne vulgaris in a mammal comprising administering to a mammal in need of treatment from ache vulgaris, an effective amount of a compound of the Formula ##STR22## where:
- R is hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted phen(C.sub.1 -C.sub.4) alkyl;
- Z and Z.sup.1 are independently selected from hydrogen and C.sub.1 -C.sub.4 alkyl or one of Z and Z.sup.1 combines with R.sup.5 to form a carbon-carbon bond;
- Y is hydrogen or methyl or combines with R.sup.1 to form a carbon-carbon bond;
- R.sup.1 is hydrogen or combines with one of Y or R.sup.1 to form a carbon-carbon bond;
- R.sup.2 is hydrogen or C.sup.1 -C.sub.4 alkyl;
- R.sup.3 is hydrogen or combines with R.sup.1 to form a carbon-carbon bond;
- R.sup.4 is hydrogen or combines with R.sup.5 to form a carbon-carbon bond;
- R.sup.5 is hydrogen or combines with one of Z or Z.sup.1 to form a carbon-carbon bond;
- n is 1 or 2;
- X is hydrogen, halogen, NO.sub.2, cyano, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, carboxy, C.sub.1 -C.sub.6 alkoxycarbonyl, amino, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino, amido, C.sub.1 -C.sub.4 alkylamido, C.sub.1 -C.sub.4 dialkylamido, mercapto, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, or a group -A-R.sup.6 where A is C.sub.1 -C.sub.6 alkylene, C.sub.2 -C.sub.6 alkenylene or C.sub.2 -C.sub.6 alkynylene;
- and R.sub.6 is halogen, hydroxy, CF.sub.3, C.sub.1 -C.sub.6 alkoxy, carboxy, C.sub.1 -C.sub.6 alkoxycarbonyl, amino, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino, amido, C.sub.1 -C.sub.4 alkylamido, C.sub.1 -C.sub.4 dialkylamido, C.sub.1 -C.sub.4 alkylsulfonylamino, aminosulfonyl or C.sub.1 -C.sub.4 alkylaminosulfonyl, or a pharmaceutically acceptable salt thereof;
- provided that
- at least one of R.sup.1 and R.sup.5 is hydrogen;
- (b) when R is hydrogen, methyl, ethyl or benzyl, X is other than hydrogen or methoxy;
- and
- (c) when R is methyl, R.sup.2 is other than methyl.
A method of treating acne vulgaris in a mammal comprising administering to a mammal in need of treatment from acne vulgaris, an effective amount of a compound of the Formula ##STR23## where:
- R is hydrogen or C.sub.1 -C.sub.4 alkyl;
- Z and Z.sup.1 are independently hydrogen or methyl;
- Y is hydrogen or methyl, and is in a trans configuration in relation to the 4a position hydrogen;
- R.sup.1, R.sup.3, R.sup.4 and R.sup.5 are hydrogen;
- R.sup.2 is hydrogen or methyl;
- n is 1 or 2;
- X is halogen, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy or -A-R.sup.6 where A is C.sub.1 -C.sub.4 alkylene and R.sup.1 is C.sub.1 -C.sub.4 alkoxycarbonyl;
- or a pharmaceutically acceptable salt thereof;
- provided that
- (b) when R is hydrogen, methyl or ethyl, X is other then hydrogen or methoxy;
- and
- (c) when R is methyl, R.sup.2 is other than methyl.
A method of treating acne vulgaris in a mammal comprising administering to a mammal in need of treatment from ache vulgaris, an effective amount of a compound of the Formula ##STR24## where:
- R is hydrogen or methyl;
- Z and Z.sup.1 are hydrogen or methyl
- Y is hydrogen or methyl, and is in a trans configuration in relation to the 4a position hydrogen;
- R.sup.1, R.sup.3, R.sup.4 and R.sup.5 are hydrogen;
- R.sup.2 is hydrogen or methyl;
- n is 1 or 2;
- X is halogen, CF.sub.3, or C.sub.1 -C.sub.4 alkyl;
- or a pharmaceutically acceptable salt thereof;
- provided that
- (c) when R is methyl, R.sup.2 is other than methyl.
Dependencies are inferred from the claim text.