Bi-aromatic compounds comprising an adamantyl group in para-position, pharmaceutical and cosmetic compositions containing them and their utilization

摘要

1-Phenyl-adamantane derivatives of formula (I) and their salts and isomers are new. R1 = Me, (CH2)nOR4, O(CH2)m(CO)nR5, COR6 or COOR7; R2 = H, halo, 1-20C alkyl, OR4 or OCH2OCH2CH2OMe; R3 = (i) Y(CH2)pY(CH2)qR8, (ii) (CH2)p(Y)s(CH2)qR8, (iii) Y(CH2)qR8 or (iv) CH=CH(CH2)rR8; X = one of the following groups, which can be read in both directions: (a) C(O)O; (b) C(O)S; (c) C(O)NR10; (d) C(S)NR10; (e) C(O)CH2W; (f) CH(OH)CH2W; (g) CH(R10)W; (h) CH(OH)C IDENTICAL C; (i) C(O)C IDENTICAL C; (j) -C IDENTICAL C-; (k) C(O)CH=CH; (l) CH(OH)CH=CH; (m) CR10=CH; Ar = (a) p-phenylene substituted by R9, (b) pyridinediyl, (c) 2,6-naphthylene substituted by R9, (d) furandiyl, (e) thiophenediyl or (f) (1-R10)-pyrrolediyl; m = 1-3; n = 0 or 1; p = 1-12; q = 0-12; r = 0-10; s = 0 or 1; t = 0-2; Y = O or SOt; W = O, SOt or NR10; R4 = H, lower alkyl or COR11; R5 = lower alkyl or heterocyclyl; R6 = H, lower alkyl or NR'R"; R', R" = H, lower alkyl, mono- or polyhydroxyalkyl, optionally substituted aryl, or amino acid, peptide or sugar residues; or R'+R" = a heterocycle; R7 = H, 1-20C alkyl, alkenyl, mono- or polyhydroxyalkyl, optionally substituted aryl or aralkyl, or a sugar, aminoacid or peptide residue; R8 = H, 1-20C branched alkyl, a 3-6C cycloaliphatic group, mono- or polyhydroxyalkyl (with OH groups optionally protected as methoxy, acetoxy or acetonide), aryl, alkenyl, alkynyl, COR6, COOR7, aminoalkyl, mono- or di(lower alkyl)aminoalkyl or heterocyclyl; R9 = H, halo, 1-20C alkyl, OR4 or OCH2OCH2CH2OMe; R10 = H or lower alkyl; and R11 = lower alkyl; provided that q = 7-12 when X is (e), R3 is (iii) with Y = O and R8 is H.