GB846920A - Steroid compounds and their preparation - Google Patents

Abstract

The invention comprises steroid 4,6-dienes of the general formula: <FORM:0846920/IV(b)/1> wherein R represents an alkyl group containing 1 to 9 carbon atoms and R1 represents hydrogen or an acyl group derived from a hydrocarbon carboxylic acid having from 2 to 9 carbon atoms or formic acid, and the preparation thereof by dehydrohalogenating a compound of the general formula: <FORM:0846920/IV(b)/2> wherein R and R1 have the above significance and X represents chlorine or bromine. The above process may be modified in that the starting compounds are prepared by chlorinating or brominating a compound of the general formula: <FORM:0846920/IV(b)/3> wherein R and R1 have the above significance, in the 6-position with an N-chloro-amide or N-bromo-amide respectively, for example, by heating. The dehydrohalogenation may be effected heating with a base including alkali metal by hydroxides and alkoxides and organic amines, e.g. a high boiling liquid tertiary amine such as an alkalated pyridine and quinoline, or mixtures thereof. The esterification of the 17b -hydroxy group may be carried out before the dehydrohalogenation step or on the 4,6-diene product-preferably in the former stage. The examples refer to the preparation of a large number of 6-halo-intermediate compounds and 4, 6-androstardiene products falling within the scope of the above first two general formulae. Steroids of the third general formula above are prepared by dehydrogenating a 17a -alkyl-17b -R 'O-antrostene having a double bond in the 4, 5- or 5, 6- position and a 3-hydroxy or 3-keto group and, if necessary, oxidising the 3-hydroxy group to a 3-keto group. Suitable dehydrogenation agents are bromine, manganese dioxide or benzoquinone or derivatives thereof in the presence of metal alcoholates or phenolates.ALSO:Therapeutic compositions comprise steroid compounds of the general formula: <FORM:0846920/VI/1> wherein R represents an alkyl group containing 1 to 9 carbon atoms and R1 represents hydrogen or an acryl group derived from a hydrocarbon carboxylic acid having 2 to 9 carbon atoms or formic acid, dispersed in an aqueous suspension or dissolved in a therapeutically acceptable oil or oil-water emulsion.