7.alpha.-Halogeno-3,20-dioxo-1,4-pregnadienes, methods for their manufacture, their use as anti-inflammatory agents, and pharmaceutical formulations useful therefor

A 3,20-dioxo-7-halogeno-1,4-pregnadiene of the following formula:

• ##STR10## wherein A is hydrogen, and provided Y is (H,.beta.OH), chlorine, fluorine or methyl;
• B is hydrogen or, together with Q, is a 14.alpha.,17.alpha.-alkylideneoxy derivative;
• X is a member selected from the group consisting of hydrogen having an atomic weight less than 100;
• Y is a member selected from the group consisting of (H,H) provided X is hydrogen, oxygen, (H,.beta.OH), (H,.beta.OCOH);
• and (H,.beta.-halogen) provided X is chlorine or bromine, said .beta.-halogen having an atomic weight of less than 100 and being at least as electronegative as X;
• Z is fluorine, chlorine, bromine and iodine;
• Q is a member selected from the group consisting of hydrogen provided W is a member selected from the group consisting of (H,H) and (H, lower akyl);
• chlorine;
• bromine;
• and OV wherein V is a member selected from the group consisting of hydrogen and an acyl radical of a hydrocarboncarboxylic acid having up to 12 carbon atoms or of benzoic acid substituted by a halogen or methoxy group;
• W is a member selected from the group consisting of (H,H);
• (H, lower alkyl);
• (H,.alpha.-OV.sub.1) wherein V.sub.1 is a member selected from the group consisting of hydrogen and an acyl radical of an acid selected from the group consisting of a hydrocarbonacarboxylic acid having up to 12 carbon atoms, benzoic acid substituted by a halogen or methoxy group, retinoic acid, and isonicotinic acid;
• .dbd.CHT wherein T is a member selected from the group consisting of hydrogen, lower alkyl, fluorine and chlorine, and
• W and Q taken together is a member selected from the group consisting of 16.alpha.,17.alpha.-lower alkylidenedioxy;
• 16.alpha.,17.alpha.-cycloalkylidenedioxy;
• the grouping ##STR11## wherein R is lower alkyl;
• and the grouping ##STR12## wherein R.sub.1 is lower alkyl or phenyl;
• M is a member selected from the group consisting of --OR.sub.2 when Q is O-acyl, R.sub.2 being lower alkyl or halogeno lower alkyl;
• --CHO, acetals, hemiacetals and acylals thereof;
• --COOR.sub.3 wherein R.sub.3 is an alkyl having up to 12 carbon atoms;
• --CH.sub.2 G wherein G is a member selected from the group consisting of hydrogen, halogen having an atomic weight of less than 100, OV.sub.2 wherein V.sub.2 is a member selected from the group consisting of hydrogen and 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, phosphoric acid and mono- and dialkali, and alkaline earth metals salts thereof;
• and OV.sub.2 together with OV is a member selected from the group consisting of alkylidene dioxy and alkylorthoalkanoate;
• when W is hydrogen, the D-homo analogs thereof.