Patent IL-119640-A (IL)
Title: Aromatic compounds bearing 3-(1-adamantyl) phenyl groups and pharmaceutical and cosmetic compositions containing them
IPC: A61K8/00
Filed: 1996-11-18
Abstract: Bicyclic aromatic compunds, of the formula 2142 כ" ה באלול התשס" א - September 13, 2001 in which: R1 represents (i) the -CH3 radical; (ii) the radical -(CH2)n-O-R4; (iii) the radical -O- (CH2)m - (CO)n-R5; (iv) the radical -CO-R6; (v) the radical -CO-O-R7; the values m and n, as well as the various radicals R4 to R7, having the meaning given below, R2 represents a hydrogen or halogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, a radical -OR4 or an -O-CH2-O-CH2-CH2-O-CH3 radical, R3 represents: (i) a radical -Y- (CH2)p-Y- (CH2)q-R8; (ii) a radical -(CH2)p-Y - (CH2)q-R8; (iii) a radical -Y- (CH2)q-R8; (iv) a radical -CH=CH- (CH2)r-R8; (v) a radical - (CH2)q-R8; the values p, q and r and the radicals Y and R8 having the meaning given below, X represents the linkages of formulae (a) - (k) below which may be read in both directions: Ar represents a radical chosen from the radicals of the formulae 2143 כ" ה באלול התשס" א - September 13, 2001 it being understood in all of the above text that: m is an integer equal to 1, 2 or 3 n is an integer equal to 0 or 1 p is an integer between 1 and 12 inclusive q is an integer between 0 and 12 inclusive r is an integer between 0 and 10 inclusive t is an integer equal to 0, 1 or 2 Y represents an oxygen atom or a radical S(O)t W represents an oxygen atom, a radical S(O)t or a radical N-R10; R4 represents a hdyrogen atom, a lower alkyl radical or a radical -CO-R11; R5 represents a lower alkyl or a heterocycle; R6 represents a hydrogen atom, a lower alkyl radical or a radical of the formula in which R' and R" represent a hydrogen atom, a lower alkyl radical, a mono- or polyhrdroxyalkyl radical, an optionally substituted aryl radical or an amino acid or peptide or sugar residue, or alternatively, taken together, form a heterocycle, R7 represents a hydrogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, an alkenyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl or aralkyl radical or a sugar residue or an amino acid or peptide residue, R8, which may be identical or different, represents a hydrogen atom, a branched alkyl radical having from 1 to 20 carbon atoms, a C3-C6 cycloaliphatic radical, a monohydroxyalkyl radical or a polyhydroxyalkyl radical in which the hydroxyls are optionally protected in methoxy or acetoxy or acetonide form, an aryl radical, an alkynyl radical, a radical CO-R6, a radical -CO-O-R7, an amino alkyl radical whose amine function is optionally substituted with one or two lower alkyl groups, a heterocycle, R7 having the meaning given above, R9, which may be identical or different, represents a hydrogen or halogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, a radical -OR4 or an -O-CH2-O-CH2-CH2-O-CH3 radical, R10, which may be ideentical or different, represents a hydrogen atom or a lower alkyl radical, R11 represents a lower alkyl radical given that when: X represents the linkage of formula (a), (b), (c), (g), (h), (j) or (k), then R3 is other than the radical of formula (iii), (iv) or (v) in which R8 is a hydrogen atom, X represents the linkage of formula (a), then R3 is other than radical (iii), X represents the linkage of formula (b) and R3 represents the radical of formula (iii) in which Y represents a sulphur atom, then R8 is other than an aryl radical, X represents the linkage of formula (g), (h), (j) or (k) and R3 represents the radical of formula (v), then R8 is other than a monohydroxyalkyl or polyhydroxyalkyl radical, or a C3-C6 cycloaliphatic radical, as well as the salts thereof and the optical and geometrical isomers thereof. They have retinoic acid activity and some are retinoic acid receptor antagonists. 2144 כ" ה באלול התשס" א - September 13, 2001