Novel enol esters of steroids, compositions containing such compounds, processes for their preparation and methods of treatment therewith

Claim 1

Novel compound having the general formula St--R wherein R is ##STR7## where R 1 is a β- or γ-halogensubstituted alkyl group having 2 to 4 carbon atoms, the halogen being chlorine or bromine; where R 2 is selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, and halogen; where A is a straight hydrogen chain having at most 4 carbon atoms and being saturated or containing one double bond, at most 2 hydrogen atoms of A being replaced by lower alkyl and at most one of the hydrogen atoms situated at the carbon atom adjacent to a ##STR8## being replaced by a group selected from the group consisting of amino and lower alkanoylamino; where X is selected from the group consisting of --O-- and --S--; where k and m are independently selected from the group consisting of zero and one, k always being one when m is one; wherein St is the radical of a steroid having a cyclopentanophenanthrene carbon-carbon skeleton containing up to a maximum of 40 carbon atoms, inclusive of substituents, said radical including the carbon-carbon skeleton of a steroid nucleus which is an unsaturated gonane nucleus having up to a maximum of three double bonds, said steroid radical being attached to R at the 3-position thereof, said position wherein said steroid is attached to R always being situated at the end of an olefinic bond of said gonane nucleus, said position being identified according to steroid nomenclature, selected from such compounds wherein said radical, St, of a steroid as defined above, has a carbon-carbon skeleton selected from the group consisting of: the carbon-carbon skeletons of estra-3,5-diene, estra-3,5(10)-diene, 5α-androst-2-ene, 5α-androst-3-ene, androsta-3,5-diene, pregna-3,5-diene, pregna-1,3,5-triene, and pregna-3,5,7-triene, and such compounds wherein a hydroxyl group connected to a non-olefinic carbon atom of the steroid skeleton of St, that is a non-enolic hydroxyl group, is esterified with an acid selected from the group consisting of alkane monocarboxylic acids having at most ten carbon atoms, alkane dicarboxylic acids having at most four carbon atoms, aromatic carboxylic acids having at most ten carbon atoms, and inorganic polybasic acids, and wherein one or more of the remaining free acid group or groups of any such polybasic acid is in the free form, in the form of a salt thereof with a pharmaceutically acceptable cation, or etherified with an alcohol selected from the group consisting of aliphatic and cycloaliphatic alcohols having at most six carbon atoms.