GB872210A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Abstract

The invention comprises compounds of the formula: <FORM:0872210/IV (b)/1> wherein R is hydrogen or the acyl radical of a hydrocarbon carboxylic acid of 1-12 carbon atoms, inclusive; R1 is hydroxy or keto; and X is hydrogen, bromine, fluorine or chlorine; and the 1,2-dehydro analogues thereof; compounds having the formulae <FORM:0872210/IV (b)/2> wherein R is hydrogen or the acyl radical of a hydrocarbon carboxylic acid of from 1-12 carbon atoms inclusive, R1 is a hydroxy or a keto group, R11 is hydrogen, lower alkoxy, trifluoromethyl or carbo-lower-alkoxy and M is an alkali metal, and the preparation thereof by converting 11b ,21 - dihydroxy - 6 - methyl - 4,17(20)-pregnadiene-3-one or a 21-ester thereof to a 2-carbonyl derivative, methylating to produce the corresponding 2-methyl-2-carbonyl compound, removing the 2-carbonyl group to produce the 2-methyl compound, esterifying the thus-produced 21-hydroxy compound to produce a 21-esterified compound and oxidatively hydroxylating the D 17(20)-double bond to produce 2,6a - dimethyl hydrocortisone acylate. The 11-hydroxy group may be oxidised e.g. with chromic acid to form an 11-keto group. A D 1-double bond may be introduced by means of a fungus of the genus Septomyxa or selenium dioxide. Illustrative products of the invention are 2,6a -dimethylhydrocortisone, 2,6a - dimethylhydrocortisone, 2,6a -dimethylcortisone, 2,6a -dimethyl-9a -fluorohydrocortisone, 2,6a -dimethyl-9a -fluorocortisone, and the 21-acetates thereof. Specification 829,903 is referred to.ALSO:Pharmaceutical compositions comprise 2,6a -dimethyl - 11b ,17a ,21 - trihydroxy - 4 - pregnene-3,20-dione, the 21-esters thereof, or the 9a -fluoro or 11-keto analogues thereof and a pharmaceutical diluent. They may be employed for injection in suspensions, orally, or topically as ointments, creams, and lotions. Specification 829,903 is referred to.