17-deoxycorticosteroid-21-O!carboxylic esters, processes for their preparation and pharmaceuticals containing these compounds

US5824670A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Ulrich Stache
• Hans G. Alpermann · Bocholt, DE
• Manfred Bohn · Hofheim, DE

Key dates

• Filing date: Sep 18, 1995
• Grant date: Oct 20, 1998
• Expiry date: Sep 18, 2015

Classification

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

Abstract

17-Deoxycorticoid-21-carboxylic 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 and R(2) is H or methyl. They are obtained by reacting a compound of the formula II, ##STR2## in which R(4) is OH, with an activated carboxylic acid of the formula III, EQU R(5)-CO--X-R(1) III. The compounds I possess very strong local and topical antiinflammatory activity and exhibit a very good ratio of local to systemic antiinflammatory effect, which ratio is often clearly superior to that of structurally related corticoid 21-esters which do not carry any aryl or hetaryl group in the 21-ester residue or to that of analogous 17-deoxycorticoids having an unesterified, that is a free, 21-hydroxyl group.