GB835514A - 2-methyl-1, 4-pregnadienes - Google Patents

Abstract

The invention comprises 2-methyl-1,4-pregnadienes of the general formula <FORM:0835514/IV (b)/1> wherein R represents hydrogen or an alkanoyl radical containing up to 6 carbons and X represents the divalent radical >CHOH or >CO. The compounds may be prepared by treating the corresponding 4-pregnene compounds in which R is an alkanoyl radical with a mild oxidizing agent such as selenium dioxide, and then, if desired, replacing R by hydrogen. In the examples, 11b -16a ,17a ,21 - tetrahydroxy-2 - methyl - 1,4 - pregnadiene - 3,20 - dione and the corresponding 16a ,21-diacetoxy compound, and 16a ,21 - diacetoxy - 17a - hydroxy - 2 - methyl - 1,4 - pregnadiene - 3,11,20 - trione are prepared. 2a -Methyl-4-pregnenes of the general formula <FORM:0835514/IV (b)/2> wherein R represents an alkanoyl radical containing up to 6 carbon atoms, are prepared by reacting the required 21-alkoxyloxy-20-ethylenedioxy - 16a ,17a - dihydroxy - 4 - pregnene-3-ones with diethyl oxalate in the presence of an alkali metal alkoxide to form the alkali metal enolate of the corresponding 2-ethoxy-oxalyl-4-pregnenes, treating these compounds with the methyl halide to form the corresponding 2a - methyl - 2 - ethoxyoxalyl - 4 - pregnenes, alkaline hydrolysing these compounds to form the corresponding 2a -methyl-4-pregnenes, and removing the 20-ethylenedioxy radical from these pregnenes by acid hydrolysis. Specification 824,351 is referred to.ALSO:A therapeutic composition suitable for injection, internal use, or topical application contains as the active ingredient a 2-methyl-1,4-pregnadiene of the general formula <FORM:0835514/VI/1> wherein R represents a hydrogen atom or an alkanoyl radical having up to 6 carbon atoms and X represents the divalent radical ¦CHOH or ¦CO. Thus the composition may be in the form of a tablet, pill, capsule, powder, ointment, cream, suspension or solution.