EP0057401A1 — Aromatic heterocyclic esters of steroids, their preparation and pharmaceutical compositions containing them

USPTO Abstract

Disclosed herein are novel 3,20-dioxo-1,4-pregnadiene-17-01-17-aromatic heterocyclic carboxylates (and the 6-dehydro and 1,2-dihydro derivatives thereof) of general formula I: wherein: A is hydrogen or, provided that Y is (H,βOH), A may also be chloro, fluoro or methyl; X is hydrogen or a halogen atom having an atomic weight less than 100; Y is oxygen, (H,βOH) or, provided that X is hydrogen, Y may also be (H,H) or, provided X is chloro or bromo, Y may also be (H,β-halogen), the β-halogen having an atomic weight less than 100 and being at least as electronegative as X; Z is hydrogen, methyl, chloro or fluoro; Z' is hydrogen or, provided that Z is hydrogen, may also be halogen having an atomic weight of less than 100; V is an acyl radical of a thiophenecarboxylic acid, pyrrolecarboxylic acid or furancarboxylic acid or the methyl- or halogen-substituted derivatives thereof; W is (H,H), (H, lower alkyl) or (H, aOV,) where V, is hydrogen or specified acyl radicals, or W is a methylene or substituted methylene group; and G is hydrogen, a halogen atom having an atomic weight of less than 100 or is -QV 2 where Q is oxygen or sulfur and V 2 is specified acyl radicals. The novel compounds exhibit anti-inflammatory activity and their use for this purpose is disclosed. Also disclosed are methods for the preparation of the novel compounds.