Corticosteroid 17-alkyl carbonate 21-[0]-carboxylic and carbonic esters, and pharmaceuticals containing these compounds

US5608093A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Ulrich Stache
• Hans G. Alpermann · Bocholt, DE
• Walter D urckheimer · Hattersheim, DE
• Manfred Bohn · Hofheim, DE

Key dates

• Filing date: Aug 25, 1994
• Grant date: Mar 4, 1997
• Expiry date: Aug 25, 2014

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J43/003
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Corticoid 17-alkyl carbonate 21-carboxylic and carbonic esters of the formula I ##STR1## are described in which A is CHOH and CHCl, CH.sub.2, C.dbd.O or 9(11) double bond; Y is H, F or Cl; Z is H, F or CH.sub.3 ; R(1) is aryl or hetaryl; n and m are zero or 1; R(2) is alkyl or --(CH.sub.2).sub.2 --OCH.sub.3 ; R(3) is H or methyl. They are obtained by reacting a compound of the formula II, ##STR2## in which R(5) is OH, with an activated carboxylic acid of the formula III, EQU R(6)--CO--(O).sub.n --(X)--R(1) III. The compounds I have a very strong local and topical antiinflammatory action and exhibit a very good ratio of local to systemic antiinflammatory effects, which ratio is often markedly superior to that of analogous corticoid 17-alkyl carbonate 21-esters which do not carry any aryl or heteraryl group in the 21-ester radical.