GB878706A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Abstract

The invention comprises compounds having the formula: <FORM:0878706/IV (b)/1> wherein R1 is an alkyl radical containing from 1-6 carbon atoms inclusive or an alkinyl radical of the structure -C=CR3 in which R3 is hydrogen or an alkyl radical of 1-4 carbon atoms, and R2 is hydrogen or the acyl radical of an organic carboxylic acid containing from 1-12 carbon atoms inclusive and processes for the preparation thereof by subjecting the corresponding D 4 compounds to biological or chemical dehydrogenation. Suitable microorganisms are Septomyxa, Corynebacterius, Didymella, Calonectria, Alternaria, Colletotrichum, Cylindrocarpon, Ophiobolus, Fusarium, Listeria, Erysipelothrix, Mycobacterium, Tricothecium, Leptosphaeria, Cucurbitaria and Nocardia. Chemical dehydrogenation may be effected with selenium dioxide. The 6b -compound may be epimerised to the 6a -compound by means of an acid or base. The 21-ester group may be hydrolysed to a 21-OH group which may be reesterified. Illustrative compounds of the invention are 6a -fluoro- 17b -hydroxy- 17a -methyl-1,4-androstadien 3-one and the 17-acetate thereof, 6a -fluoro-17b - hydroxy-17a -ethinyl-1,4-androstadiene-3-one and the 17-acetate thereof, 6a -fluoro-17a -methylestradiol and the 17-acetate thereof, and 6a -fluoro-17a -ethinylestradiol and the 17-acetate thereof. Many other esters are mentioned. Specifications 713,898, 724,094 and 874,214 are referred to.ALSO:Pharmaceutical compositions comprising compounds of the formulae <FORM:0878706/VI/1> <FORM:0878706/VI/2> wherein R1 is an alkyl radical containing from 1-6 carbon atoms inclusive or an alkinyl radical of the structure -C ­ CR3 in which R3 is hydrogen or an alkyl radical of 1-4 carbon atoms, and R2 is hydrogen or the acyl radical of an organic carboxylic acid containing from 1-12 carbon atoms, and a pharmaceutical diluent are administered orally as pills, tablets, syrups or elixirs or as injectable products in liquid forms. Specifications 713,898, 724,094 and 874,214 are referred to.