6-Acyloxy-1,4,6-pregnatrienes, their use as anti-inflammatory agents, methods for their manufacture, and 6-oxo-1,4-pregnadiene intermediates

Claim 1

A 6-acyloxy-3,20-dioxo-1,4,6-pregnatriene of the following formula I: ##STR13## wherein A is hydrogen or, provided Y is (H,βOH), A is chlorine, fluorine or methyl; B is hydrogen or, together with Q, is a 14α,17α-alkylidenedioxy derivative; X is hydrogen, fluorine or chlorine; Y is oxygen, (H,βOH), (H,βOCOH); or (H,β-chlorine) or (H,β-fluorine) provided X is chlorine; Z is hydrocarboncarbonyl, alkoxycarbonyl, thioalkoxycarbonyl, or thioalkoxythiocarbonyl wherein Z has up to 12 carbon atoms; Q is hydrogen provided W is (H, lower alkyl); or OV wherein V is hydrogen or an acyl radical of a hydrocarboncarboxylic acid having up to 12 carbon atoms or an acyl radical of benzoic acid substituted by a halogen or methoxy group or an acyl radical of retinoic acid provided W is other than (H,α-retinoyloxy); W is (H, lower alkyl); (H,α-OV 1 ) wherein V 1 is hydrogen or an acyl radical of an acid selected from the group consisting of a hydrocarboncarboxylic acid having up to 12 carbon atoms, benzoic acid substituted by a halogen or methoxy group, retinoic acid, and isonicotinic acid; ═CHT wherein T is hydrogen, lower alkyl, fluorine or chlorine, and W and Q taken together is a 16α,17α-lower alkylidenedioxy; a 16α,17α-cycloalkylidenedioxy; the grouping ##STR14## wherein R and R 1 are lower alkyl; or the grouping ##STR15## wherein R 2 is lower alkyl or phenyl; M is --OR 3 when Q is O-acyl, R 3 being lower alkyl or halogeno lower alkyl; --CHO, acetals, hemiacetals and acylals thereof; --COOR 4 wherein R 4 is alkyl having up to 12 carbon atoms; --CH 2 G wherein G is halogen having an atomic weight of less than 100 provided Q is not hydrogen, or G is OV 2 wherein V 2 is hydrogen, an acyl radical of an acid selected from the group consisting of a hydrocarboncarboxylic acid having up to 12 carbon atoms, benzoic acid substituted by a halogen or methoxy group, retinoic acid, isonicotinic acid, or phosphoric acid and mono- and dialkali and alkaline earth metal salts thereof; and G together with Q is an alkylidenedioxy or an alkylorthoalkanoate; and the 1,2-dihydro analogs of the foregoing.