Retinoic acid esters of steroids of the pregnane series, their use in the treatment of acne and pharmaceutical formulations useful therefor
AssigneeSchering Corporation
InventorsCharles J. Casmer, Richard W. Draper
Life of this patent
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Abstract
Novel retinoic acid esters of anti-inflammatory steroids of the pregnane series are described and their use in the treatment and control of acne vulgaris via the topical or intralesional route. A preferred mode of the invention comprises treating acne by applying topically to the affected area hydrocortisone 21-all-trans-retinoate in concentrations of from about 0.05 to about 0.15 percent. Pharmaceutical formulations and methods for the manufacture of the novel steroidal retinoates are also described.
Claims25
A retinoic acid ester of a steroid of the pregnane series having anti-inflammatory activity and having a 20-ketone and a 3-keto-4-dehydro system or an enol ether thereof or a 3-desoxy-[3,2-c]-pyrazole derivative thereof, and also having a hydroxyl group on at least one of positions 21, 17.alpha. and 16.alpha. with the proviso that on at least one of positions 17.alpha. and 21 there is a hydroxyl group or a hydrolyzable derivative thereof;
- said retinoic acid ester being a member selected from the group consisting of a 21-retinoate, 17.alpha.-retinoate, 16.alpha.-retinoate, 16.alpha.,21-diretinoate and a 17.alpha.,21-diretinoate of said steroid of the pregnane series.
The method of treating and controlling acne which comprises applying either topically or intralesionally to the affected area in a concentration effective for the treatment of acne, a steroidal retinoate ester selected from the group consisting of a 21-retinoate, a 17.alpha.-retinoate, a 16.alpha.-retinoate, a 16.alpha.,21-diretinoate and a 17.alpha.,21-diretinoate ester of a steroid of the pregnane series, said steroid having anti-inflammatory activity and having a 20-ketone and a 3-keto-4-dehydro system or an enol ether thereof or a 3-desoxy-[3,2-c]pyrazole derivative thereof, and also having a hydroxyl group on at least none of positions 21, 17.alpha. and 16.alpha. with the proviso that on at least one of positions 17.alpha. and 21 there is a hydroxyl group or a hydrolyzable derivative thereof,
- together with a non-toxic, pharmaceutically acceptable carrier.
A pharmaceutical composition comprising an anti-acne effective amount of a steroidal retinoate ester selected from the group consisting of a 21-retinoate, a 17.alpha.-retinoate, a 16.alpha.-retinoate, a 16.alpha.,21-diretinoate and a 17.alpha.,21-diretinoate of a steroid of the pregnane series, said steroid having anti-inflammatory activity and having a 20-ketone and a 3-keto-4-dehydro system or an enol ether thereof or a 3-desoxy-[3,2-c]-pyrazole derivative thereof, and also having a hydroxyl group on at least one of positions 21, 17.alpha. and 16.alpha. with the proviso that on at least one of positions 17.alpha. and 21 there is a hydroxyl group or a hydrolyzable derivative thereof,
- together with a non-toxic, pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.