GB795454A - Steroid compounds - Google Patents

Abstract

The invention comprises 3 - ethylenedioxy-11,20 - diketo - 16,17 - oxido - 21 - acyloxy-D 5-pregnenes of the general formula: <FORM:0795454/IV (b)/1> wherein R represents an acyloxy group, and the preparation thereof by reacting a 3-ethylene-dioxy - 11,20 - diketo - 21 - acyloxy - D 5,16-pregnadiene with hydrogen peroxide in the presence of an inorganic base, and by reacting an ester of 3-ethylene-dioxy-11,20-diketo-16,17-oxido - 21 - oxalyl - D 5 - pregnene with iodine in the presence of a base to produce a 3-ethylenedioxy - 11,20 - diketo - 16,17 - oxido - 21-iodo - D 5 - pregnene and reacting this compound with a salt of a carboxylic acid. The latter process may be modified in that the ester of 3 - ethylenedioxy - 11,20 - diketo - 16,17-oxido - 21 - oxalyl - D 5 - pregnene is prepared by the method claimed in Specification 795,453. In the reaction with hydrogen peroxide, the inorganic base may be an alkali metal hydroxide, carbonate or bicarbonate such as potassium hydroxide, carbonate or bicarbonate or sodium hydroxide or carbonate, the reaction solvent may be methanol, ethanol, propanol or butanol, and the reaction may be carried out at room temperature. In the reaction with iodine in the presence of a base, it is preferable to use methanolic sodium methoxide as the base although other alcohols and alkali metal alkoxides may be used. The salt of a carboxylic acid is preferably sodium benzoate or a salt of an alkanoic acid, e.g. sodium acetate or propionate or potassium acetate. In the example 3 - ethylenedioxy - 11,20 - diketo - 16,17-oxido - 21 - acetoxy - D 5 - pregnene and the intermediate compound 3-ethylenedioxy-11,20-diketo - 16,17 - oxido - 21 - iodo - D 5 - pregnene are prepared.