GB899219A - Steroid compounds - Google Patents

Abstract

The invention comprises steroid compounds of the general formula <FORM:0899219/IV (b)/1> wherein X represents hydrogen or bromine or X is not present when there is a 1,2-double bond, Y represents hydrogen when X represents bromine or is not present, chlorine when X represents hydrogen or bromine, or Y is not present when there is a 6,7 double bond and when X represents hydrogen or is not present, and R represents hydrogen or the acyl residue of a carboxylic acid containing not more than 9 carbon atoms; and processes for the preparation of: 2a -bromo-4-hydroxy(or acyloxy)-17a -methyltestosterone or 2a - bromo - 6 - chloro - 4 - hydroxy (or acyloxy) - 17a - methyl - testosterone by brominating the corresponding 4-hydroxy-(or acyloxy) - 17a - methyl - testosterone with bromine or with N-bromosiccinimide in an organic halogenated solvent such as carbon tetrachloride, chloroform, methylene chloride or acetic acid; 2a -bromo-6b -chloro-4-hydroxy (or acyloxy)-17a -methyl-testosterone or 6b -chloro-4-hydroxy (or acyloxy)-17a -methyl-testosterone by chorinating the corresponding 4-hydroxy-(or acyloxy)-17a -methyl-testosterone with chlorine or with N-chlorosuccinimide in an organic halogenated solvent such as carbon tetrachloride chloroform or methylenechloride; 2a -bromo-6a -chloro-4-hydroxy (or acyloxy)-17a -methyl-testosterone- or 6a -chloro-4-hydroxy (or acyloxy)-17a -methyl-testosterone by chlorinating the corresponding 4-hydroxy(or acyloxy)-17a -methyl-testosterone with chlorine or with N-chlorosuccinimide in acetic acid; 1, 2 - dehydro - 4 - hydroxy (or acyloxy) - 17a - methyl-testosterone by treating 2a -bromo-4-hydroxy (or acyloxy) - 17a - methyl - testosterone with lithium bromide and lithium carbonate at 80 DEG C. to 110 DEG C. for 10 to 30 hours or by dehydrogenating 4 - hydroxy (or acyloxy) - 17a - methyl-testosterone with selenium dioxide in t-butanol; 6,7-dehydro-4-hydroxy (or acyloxy)-17a - methyl - testosterone by dehydrogenating 4-hydroxy (or acyloxy)-17a -methyl-testosterone with chloranil in warm toluene or by dehydrochlorinating 6-chloro-4-hydroxy (or acyloxy)-17a -methyl-testosterone; and 1,2 : 6,7-dehydro-4 - hydroxy (or p acyloxy) - 17a - methyl - testosterone by dehydrogenating 1,2-dehydro-4-hydroxy (or acyloxy)-17a -methyl-testosterone with chloranil in warm toluene, by dehydrogenating 6,7-dehydro - 4 - hydroxy (or acyloxy) - 17a - methyl -testosterone with selenium dioxide in t-butanol, or by dehydrohalogenating 2a -bromo-6-chloro-4-hydroxy (or acyloxy)-17a -methyl-testosterone with lithium-bromide, chloride and carbonate in dimethylformamide. In any of the above processes, the product may be treated to hydrolyse a 4-acyloxy group or to acylate a 4-hydroxy group. Therapeutic compositions useful for stimulating anabolism contain as the active ingredient one or more steroids of the above general formula and a solid or liquid diluent. The composition may be in the form of a tablet, powder, pill, elixir or capsule. Specification 848,288 is referred to.