GB801793A - Improvements in or relating to steroid compounds - Google Patents

Abstract

The invention comprises 6-hydroxy-3:5-cyclo-pregnan-20-one of the formula <FORM:0801793/IV (b)/1> and the preparation thereof by heating a pregnenolone arylsulphonate or methyl pregnenolone sulphate with an alkali metal salt of a weak organic acid, water and a water soluble organic liquid, e.g. acetone, methyl ethyl ketone or dioxan, by heating pregnenolone sulphate, methyl pregnenolone sulphate or an alkali metal salt of pregnenolone sulphate with a neutral, slightly acid or slightly alkaline aqueous buffer solution, or by heating a pregnenolone aryl sulphonate or methyl pregnenolone sulphate with a mixture of an aliphatic carboxylic acid having from 1 to 5 carbon atoms and an alkali metal salt of the corresponding acid and hydrolysing the resulting 6-acyloxy-3 : 5-cyclopregnan-20-one. Suitable alkali metal salt of weak organic acids are potassium formate and acetate, sodium tartrate, glycolate and citrate, and lithium acetate. Suitable pregnenolone aryl sulphonates are benzene- and toluene-p-sulphonates. The alkali metal pregnenolone sulphate is preferably potassium pregnenolone sulphate. A number of detailed examples are given. Starting compounds. Pregnenolones of the general formula <FORM:0801793/IV (b)/2> wherein R represents an aryl, methyl or hydroxy group or the group OX, where X represents an alkali metal, may be prepared by the methods outlined for the following specific compounds: (a) pregnenolone benzenesulphonate and toluene p-sulphonate are prepared by treating pregnenolone with benzene sulphonyl chloride and toluene-p-sulphonyl chloride respectively; (b) potassium pregnenolone sulphate is prepared by reaction pregnenolone and pyridine-sulphur trioxide in the presence of pyridine and benzene, and the resulting pyridinium pregnenolone sulphate is treated with potassium chloride.ALSO:A pharmaceutical preparation comprises 6-hydroxy - 3 : 5 - cyclopregnan - 20 - one of the formula <FORM:0801793/VI/1> in admixture with a solid carrier or as a suspension or solution in a liquid carrier. In the examples, tablets are prepared containing lactone, maize starch, tragacanth, magnesium stearate and 6-hydroxy-3 : 5-cyclopregnan-20-one, and injectable solutions are prepared containing 6 - hydroxy - 3 : 5 - cyclopregnan - 20 - one with sodium carboxymethyl cellulose, polyoxyethylene sorbitan mono-oleate, methyl and n-propyl-p-hydroxybenzoate and water, and with benzyl and ethyl alcohol and ethyl oleate.