Use of 6β-fluoro-7α-halogenocorticoids as topical anti-inflammatories and pharmaceutical formulations useful therefor

Claim 1

The method of treating an inflammatory condition in a warm-blooded animal responsive to treatment with anti-inflammatory agents, which comprises applying topically to the inflamed area, a non-toxic, anti-inflammatory-effective amount of a 6β-fluoro-7α-halogeno-1,4-pregnadiene of the following formula I together with a non-toxic, pharmaceutically acceptable carrier: ##STR3## wherein A is hydrogen, or when Y is (H,β--OH), then A is also chlorine, bromine or methyl; B is hydrogen, or taken together with Q is 14α,17α-alkylidenedioxy; X is a member selected from the group consisting of hydrogen, fluorine and chlorine; Y is (H,β--OH), (H,β--OCOH), or when X is chlorine then Y is also (H,β--fluorine) or (H,β-chlorine); Z is halogen; Q is OV wherein V is hydrogen or an acyl radical of a hydrocarboncarboxylic acid having up to 8 carbon atoms; W is a member selected from the group consisting of (H,H), (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 and retinoic acid; ═CHT wherein T is a member selected from the group consisting of hydrogen, lower alkyl, fluorine and chlorine; and W together with Q is 16α,17α-lower alkylidenedioxy, 16α,17α-cycloalkylidenedioxy or 16α,17α-alkylorthoalkanoate; and M is a member selected from the group consisting of chlorine and fluorine provided Q is other than hydroxy, and OV 2 wherein V 2 is hydrogen or an acyl radical of an acid selected from the group consisting of a hydrocarboncarboxylic acid having up to 12 carbon atoms, a hydrocarbonsulfonic acid having up to 12 carbon atoms; retinoic acid, and phosphoric acid and mono and di-alkali and alkaline earth metal salts thereof; and OV 2 together with OV is a member selected from the group consisting of alkylidenedioxy and alkylorthoalkanoate.

Claim 2

The method of treating an inflammatory condition in a warm-blooded animal responsive to treatment with anti-inflammatory agents, which comprises applying topically to the inflamed area, a non-toxic, anti-inflammatory-effective amount of a 6β-fluoro-7α-halogeno-1,4-pregnadiene of the following formula I together with a non-toxic, pharmaceutically acceptable carrier: ##STR3## wherein A is hydrogen, or when Y is (H,β--OH), then A is also chlorine, bromine or methyl; B is hydrogen, or taken together with Q is 14α,17α-alkylidenedioxy; X is a member selected from the group consisting of hydrogen, fluorine and chlorine; Y is (H,β--OH), (H,β--OCOH), or when X is chlorine then Y is also (H,β--fluorine) or (H,β-chlorine); Z is halogen; Q is OV wherein V is hydrogen or an acyl radical of a hydrocarboncarboxylic acid having up to 8 carbon atoms; W is a member selected from the group consisting of (H,H), (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 and retinoic acid; ═CHT wherein T is a member selected from the group consisting of hydrogen, lower alkyl, fluorine and chlorine; and W together with Q is 16α,17α-lower alkylidenedioxy, 16α,17α-cycloalkylidenedioxy or 16α,17α-alkylorthoalkanoate; and M is a member selected from the group consisting of chlorine and fluorine provided Q is other than hydroxy, and OV 2 wherein V 2 is hydrogen or an acyl radical of an acid selected from the group consisting of a hydrocarboncarboxylic acid having up to 12 carbon atoms, a hydrocarbonsulfonic acid having up to 12 carbon atoms; retinoic acid, and phosphoric acid and mono and di-alkali and alkaline earth metal salts thereof; and OV 2 together with OV is a member selected from the group consisting of alkylidenedioxy and alkylorthoalkanoate.

Claim 4

The method according to claims 1 or 2 wherein V is an acyl radical of an unsubstituted hydrocarboncarboxylic acid having up to 8 carbon atoms or of benzoic acid substituted by a halogen or a methoxy group.

Claim 5

The method according to claims 1 or 2 wherein W is (H, CH 3 ).

Claim 9

The method of claims 6 or 7 when Z is chlorine or bromine.

Claim 10

The method of claims 6 or 7 when said 16-methyl derivative is a 16β-methyl derivative of formula II wherein Z is chlorine or bromine.

Claim 11

The method of claims 6 or 7 when said 16-methyl derivative is a 16β-methyl of formula II wherein Z is chlorine or bromine and V is propionyl.