GB889766A - Improvements in steroids and the synthesis thereof - Google Patents

Abstract

The invention comprises steroid compounds of the general formula <FORM:0889766/IV (b)/1> wherein the 1,2- and 6,7-positions are saturated or double bonded, R represents hydrogen and R1 represents a b -hydroxy group or together R and R1 represent a keto group, X and X1 each represent hydrogen or a halogen, at least one being hydrogen, Y and Y1 each represent hydrogen or a methyl group, Z represents a divalent hydrocarbon radical of less than 10 carbon atoms, M represents hydrogen on a cation which forms a water-soluble salt, and wherein P and Q each represent hydrogen or an alkyl group containing less than 8 carbon atoms, a monocyclic aromatic group, a monocyclic aralkyl group in which the alkyl portion contains less than 8 carbon atoms, a monocyclic heterocyclic group, or a monocyclic heterocyclicalkyl group in which the alkyl portion contains less than 8 carbon atoms, or together P and Q represent an alkylene group, and the preparation thereof by reacting the corresponding free 21-hydroxy compound with an anhydride or acyl halide of a dicarboxylic acid of the formula HOOC-Z-COOH, and, if desired, neutralising the resulting acid derivatives by treatment with a base to form a water-soluble salt. The reaction with the dicarboxylic acid derivative may be carried out in the presence of an organic base, e.g. pyridine, advantageously at an elevated temperature. A large number of suitable 21-hydroxy-steroid reactants for the above process are detailed. Suitable specific hydrocarbon dicarboxylic acid reactants are oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, maleic, fumaric, citraconic and phthalic acids. The water soluble salts may be derived from ammonium hydroxide, alkali metal hydroxides, alkaline-earth metal hydroxides, dialkylamines and heterocyclic amines such as pyridine. A number of detailed examples are given. Specification 889,765 is referred to.