GB855716A - Long-acting steroid compounds - Google Patents

Abstract

The invention comprises the following steriod hydrazones: <FORM:0855716/IV(b)/1> <FORM:0855716/IV(b)/2> <FORM:0855716/IV(b)/3> <FORM:0855716/IV(b)/4> <FORM:0855716/IV(b)/5> wherein R is a radical of the formula: <FORM:0855716/IV(b)/6> (in which R2 is hydrogen or phenyl, R3 is hydrogen or hydroxyl, R1 is an acyl radical of an aliphatic or cycloaliphatic hydrocarbon monocarboxylic acid of 2 to 10 carbon atoms or benzoyl, R4 is hydrogen or methyl, R5 is hydrogen, methyl, ethyl or alkynyl of 2 to 6 carbon atoms, R6 is hydrogen, methyl or ethyl, R7 is alkynyl of 2 to 6 carbon atoms, W is C=O or CHOH, X is CH2, C=O or CHOH, Y is hydrogen or halogen and Z is CH2 or CHOH) and the preparation thereof by reacting the corresponding ketosteroids with the appropriate hydrazide, preferably in an inert solvent. Advantageously a catalytic amount of an organic acid, e.g. acetic, is added to the reaction mixture, or the reaction may be performed in pure acetic acid without any inert solvent. Examples describe the preparation of benzilic, mandelic, phenylacetic and diphenylacetic acid hydrazones of esters of testosterone, 19-nor-testosterone, estrone, 17a -ethynyl-testosterone and 17a -hydroxy-progesterone, and further extensive lists of suitable starting materials and final products are given. A list of suitable esterifying acids, including alkyl, cycloalkyl and cycloalkyl-alkyl carboxylic acids, is also provided. Specification 738,230 is referred to.ALSO:Injection solutions comprising 3-benzilic acid hydrazone - testosterone - 17 - enanthate, testosterone - 17 - enanthate, 17 - benzilic acid hydrazone - estrone - 3 - enanthate and estrone-3-enanthate, each in corn oil, are described. Specification 738,230 is referred to.