Delta -cholestènes et Delta -stigmastènes et procédé pour leur préparation

The invention comprises steroids of the general formula wherein Y represents an alkyl or alkylene group containing 10 to 12 carbon atoms, R represents an alkyl or hydroxyalkyl group containing 2 to 4 carbon atoms or a corresponding acylated hydroxyalkyl group, and A represents a di (hydroxyalkyl) amino, piperidino, morpholino, thiamorpholino, pyrrolidino, N-methylpiperazino, N-(2-hydroxyethyl)-piperazino, N-(2-haloethyl)-piperazino, di (haloalkyl) amino, phthalimido or isoindolino radical, and the acid addition and quaternary ammonium salts thereof, and the preparation of the said steroids by:- (a) reacting a steroid compound of the formula wherein X represents a halogen, R1 represents an alkyl or hydroxyalkyl radical containing 2 to 4 carbon atoms, and Y has the above significance, with a di (hydroxyalkyl) amine, piperidine, morpholine, thiamorpholine, N-methyl-piperazine, N-(2-hydroxyethyl)-piperazine, isoindoline, alkali metal phthalimide or pyrrolidine, (b) if desired, acylating the hydroxy group of R when the acyl derivatives are desired, (c) if desired, reducing the phthalimido group to an isoindolino group, e.g. with lithium aluminium hydride (d) and, if desired, when A is di (haloalkyl) amino, treating the di (hydroxyalkyl) amino compound of steps (a) or (b) with a halogenating agent, preferably a chlorinating agent, (e) and forming the acid addition and quaternary ammonium salts of said steroids when desired. The invention also comprises steroids of the general formula wherein A represents a di (C1 to C4 alkyl) amino, di (hydroxyalkyl) amino, di (haloalkyl) amino, piperidino, morpholino, pyrrolidino, thiamorpholino, N-methyl-piperazino, N-(2-hydroxyethyl)-piperazino or N-(2-haloethyl) piperazino radical, n is 2, 3 or 4, and Y represents a group of the formula or and acid addition and quaternary salts thereof. The acid addition salt may be a hydrochloride, hydrobromide, thymosulphonate, maleate, succinate or citrate, and the quaternanry salt may be a methiodide, ethiodide, methobromide, or methosulphate. Some of the compounds of the third general formula above may be prepared by the following reaction scheme where n is 2, 3 or 4, Y represents a group of one of the formulae immediately above, X represents a halogen and A has the significance immediately above except that it does not represent a di (haloalkyl) amin