Patent ID: 6225328
Filing Date: 2001-05-01
Classification: A61K,A61P,A61Q,C07C,C07D

Abstract:
An adamantyl-substituted retinoid compound having the structural formula (I): ##STR8##in which R.sub.1 is (i) the --CH.sub.3 radical, (ii) the --CH.sub.2 OH radical, (iii) an --O--R.sub.3 radical, or (iv) a --CO--R.sub.4 radical, wherein R.sub.3 and R.sub.4 are as defined below; Ar is a radical of the formula: ##STR9##wherein R.sub.2 is an --(X).sub.n --(CH.sub.2).sub.p --R.sub.6 radical, an --(X).sub.n --(CH.sub.2).sub.q --R.sub.7 radical,a --CH.dbd.CH--(CH.sub.2).sub.s --R.sub.6 radical, or a --CH.dbd.CH--(CH.sub.2).sub.t --R.sub.7 radical, wherein R.sub.6, R.sub.7, X, n, p, q, s and t are as defined below; R.sub.3 is a hydrogen atom, a lower alkyl radical, or a --(CH.sub.2).sub.m --(CO).sub.n --R.sub.8 radical, wherein R.sub.8, m and n are as defined below; R.sub.4 is a hydrogen atom, a lower alkyl radical, a radical of the formula: ##STR10##or an --OR.sub.9 radical, wherein R', R"" and R.sub.9 are as defined below; R.sub.6 is a hydrogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, an alkenyl radical, or an alkynyl radical; R.sub.7 is an aryl radical, a mono- or polyhydroxyalkyl radical in which the hydroxyl moieties are optionally protected in the methoxy or acetoxy or acetonide form, an aminoalkyl radical in which the amine functional group is optionally substituted by one or two lower alkyl radicals, a polyether radical, a --COR.sub.4 radical, a saturated or unsaturated heterocycle, or an aminoaryl radical; R.sub.8 is a lower alkyl radical or a saturated heterocycle; R.sub.9 is 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; X is an oxygen atom or an --S(O).sub.r radical; R' and R"", which may be identical or different, are each a hydrogen atom, a lower alkyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl radical, or an amino acid, peptide or sugar residue, or alternatively, taken together, form a saturated heterocycle, with the proviso that R' and R"" may together form, with the nitrogen atom from which they depend, a saturated heterocycle; m is an integer ranging from 1 to 3, inclusive; n is an integer ranging from 0 to 1, inclusive; p is an integer ranging from 5 to 12, inclusive; q is an integer ranging from 0 to 12, inclusive; r is an integer ranging from 0 to 2, inclusive; s is an integer ranging from 3 to 10, inclusive; t is an integer ranging from 0 to 10, inclusive; or a pharmaceutically acceptable salt or optical or geometric isomer thereof.