Topically active steroidal anti-inflammatory agents
AssigneeSRI International
InventorsMitchell A. Avery, Masato Tanabe, Dennis Yasuda, George Detre
Life of this patent
Estimating the term…
Abstract
Introduction of a C-12 substituent and especially a .beta. C-12 substituent into glucocorticoids improves their usefulness as topical antiinflammatories by increasing their topical activity relative to their systemic activity, thus reducing systemic side effects such as adrenal suppression.
Claims14
A topical anti-inflammatory pharmaceutical composition comprising an effective inflamation treating amount of a 12-beta substituted glucocorticoid wherein said substituent is selected from the group consisting of hydroxyl and a hydroxyl with an attached lipophilic group in a pharmaceutically acceptable topical carrier.
A topical anti-inflammatory pharmaceutical composition comprising an effective inflammation treating amount of a 12-beta substituted glucocorticoid wherein said substituent is a group bridging the 12 and 17 carbon atoms and having the formula ##STR9## wherein Y and Z represent hydrogen or lower alkyl.
A glucocorticoid of the structure ##STR10## wherein R.sup.2 is hydrogen, a lower alkyl or forms a double bond between the 1 and 2 carbons;
- R.sup.4 is hydrogen, a lower alkyl or a halogen;
- R.sup.6 is hydrogen, a lower alkyl, a halogen or it can be one leg of a group bridging the 6 and 7 carbons;
- R.sup.7 is hydrogen, a lower alkyl, a halogen, a thio compound or it can be one leg of a group bridging the 6 and 7 carbons;
- R.sup.9 is an alpha group selected from hydrogen and halo;
- R.sup.11 is carboxyl, hydroxyl, or hydrogen;
- R.sup.12 is a beta hydroxyl, beta alkyl, a lower carboxylic acid ester of a beta hydroxyl or a group bridging the 12 and 17 carbon atoms having the formula ##STR11## wherein Y and Z represent hydrogen or lower alkyl;
- R.sup.15 is hydrogen a lower alkyl or a halogen;
- R.sup.16 is hydrogen, an alpha hydroxyl, a lower alkyl, a halogen or is an acetonide or acetal group bridging the 16 and 17 carbons;
- R.sup.17 is hydrogen, a lower alkyl, a halogen or an acetonide or acetal group bridging the 16 and 17 carbons;
- R.sup.20 is a carbonyl, a hydrogen plus a hydroxyl, two hydrogens or a hydrogen plus ketalized hydroxyl;
- and
- R.sup.21 is a hydroxyl, hydrogen, lower alkyl or a halo.
A glucocorticoid of the structure ##STR12## wherein X is fluoro, bromo or chloro.
A glucocorticoid of the structure ##STR13## wherein X is fluoro, chloro or bromo.
A glucocorticoid of the structure ##STR14## wherein R is hydrogen and X is fluoro, chloro or bromo.
Dependencies are inferred from the claim text.