Patent IL-100464-A (IL)
Title: 14b-H, 14- AND 15-EN-11b-ARYL- 4-OESTRENE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
IPC: C07J5/00
Filed: 1991-12-22
Abstract: Compounds having antigestagenic, antiglucocorticoid, and antiandrogenic activity of the formula R4R1R2R3 R13R12R11 X wherein either (Ia) R11 represents a hydrogen atom in the b-configuration substantially pure from a hydrogen atom in the a-configuration and each of R12 and R13 represents a hydrogen atom, or (Ib) R11 represents a hydrogen atom in the b-configuration and R12 and R13 together represent a second bond, or (Ic) R11 and R12 together represent a second bond and R13 represents a hydrogen atom, or (Id) R11 represents a hydrogen atom in the a-configuration and R12 and R13 together represent a second bond, and in (Ia), (Ib), (Ic) or (Id) X represents an oxygen atom, the hydroxyimino grouping LN-OH or two hydrogen atoms, R1 represents a hydrogen atom or a methyl group, R2 represents a hydroxy group, a C1-C10-alkoxy group or a C1-C10-acyloxy group, R3 represents a hydrogen atom; the grouping - (CH2)nCH2Z wherein n is 0, 1, 2, 3, 4 or 5 and Z represents a hydrogen atom, a cyano group or the radical -OR5 in which R5 = H, C1-C10-alkyl or C1-C10-acyl; the grouping - (CH2)mC=C-Y, wherein m is 0, 1 or 2 and Y represents a hydrogen, C1-4 alkyl, fluorine, chlorine, bromine or iodine atom, or a C1-C10 -hydroxyalkyl, C1-C10- alkoxyalkyl or C1-C10 -acyloxyalkyl radical; or the grouping - (CH2)p -CH=CH- (CH2)kCH2R6 wherein p is 0 or 1 and k is 0, 1 or 2 and R6 represents a hydrogen atom, a hydroxy group, a C1-C4-alkoxy radical or a C1-C4-acyloxy radical, wherein in Ia) and Ib) R2 is in the a-configuration and R3 is in the b-configuration and in Ic) and Id) R2 is in the b-configuration and R3 is in the a-configuration, or alternatively R2 and R3 together represent a radical of the formula x(H2C) O17 x(H2C) O17 or OO17 (CH2)x wherein x = 1 or 2, R4 represents a hydrogen atom; a cyano group; a chlorine, fluorine, bromine or iodine atom; a trialkylsilyl group; a trialkylstannyl group; a straight-chain or branched, saturated or unsaturated, C1-C8-alkyl, -acyl or-alkoxy-alkyl radical; an amino group - N R7R8 in which R7 and R8, each independently of the other, represents a hydrogen atom or a C1-C4-alkyl group; a corresponding amine oxide - N+R7O-R8; or the grouping -OR9 or -S(O)iR9 in which i = 0, 1 or 2 and R9 represents a hydrogen atom, a methyl, ethyl, propyl, insopropyl, methoxyphenyl, allyl or 2-dimethyl- aminoethyl group; or R4 represents a heteroraryl radical of the formula ABDER10 in which A represents a nitrogen, oxygen or sulphur atom, -B-D-E- represents the sequence of elements -C-C-C, -N-C-C-or -C-N-C- and R10 represents a hydrogen atom; a cyano group; a chlorine, fluorine, bromine or iodine atom; a trialkylsilyl group; a trialkylstannyl group; a straight- chain or branched, saturated or unsaturated C1-C8-alkyl, -acyl or alkoxyalkyl radical; an amino group - NR7R8 in which R7 and R8, each independently of the other, represents a hydrogen atom or a C1-C4-alkyl group; a corresponding amine oxide R7- N+ O-R8; or the grouping -OR9 or - S(O)iR9 in which i = 0, 1 or 2 and R9 represents a hydrogen atom, a methyl, ethyl, propyl, isopropyl, methoxyphenyl, allyl or 2-dimethyl- aminoethyl group; or R4 represents a heteroraryl radical of the formula R10EDAB in which A represents a nitrogen atom and -B-D-E- represents the sequence of elements -C-C-C, -N-C-C-, -C-N-C- or -C-C-N- and R10 has the meaning already given, or R4 represents a phenyl radical of the formula R10 in which R10 has the meaning already given, and the pharmacologically tolerable addition salts with acids.