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New biphenyl compounds are peroxisome proliferation activated receptor agonists used for e.g. regulating and/or restoring skin lipid metabolism and treating precancerous skin lesions, acne and eczema
New biphenyl compounds are peroxisome proliferation activated receptor agonists used for e.g. regulating and/or restoring skin lipid metabolism and treating precancerous skin lesions, acne and eczema
Biphenyl compounds (I) are new. Biphenyl compounds of formula (I), their optical and geometric isomers and salts when R1 contains a carboxylic acid functional group, are new. R1 = CH2-CH(R6)-C(O)-R5 or a group of formula (i); R2, R3 = NO2 or amino (both optionally substituted by 1-6C alkyl), H, 1-6C alkyl, aryl, halo, OR7 or polyether; X = CH2-N(R8)-CO, N(R8)-CO-N(R9), N(R8)-CO-CH2 or N(R8)-CH2-CO; R4 = T, pyrrolyl, pyrazinyl, naphthyl, biphenyl, indolyl, indenyl, benzothienyl, benzofuryl, benzothiazolyl or quinolyl (all optionally substituted by at least one R11 and/or R12), (CH2)n-(CO)qR13, adamantyl, diphenylmethyl, diphenylethyl, diphenylpropyl, diphenylbutyl, cyclopropylmethyl, cyclopentylethyl, 2-benzimidazolyl-ethyl, cyclohexylmethyl, phenoxyphenyl, 9H-fluorenyl, benzyloxyphenyl, 4-heptyloxyphenyl, 4-(6-methyl-2-benzothiazolyl)phenyl or (CH2)n-O-R13; T = phenyl, benzyl, phenethyl, thienyl, furyl or pyridyl (all substituted by R10); R5 = OH or 1-9C alkoxy; R6 = 1-6C alkyl, OR14 or SR14; R7 = H, 1-6C alkyl, aryl or aralkyl; R8, R9 = H or 1-6C alkyl; R10 = S(O)mR15, (CH2)p-COR16 or O-R17; R11, R12 = H, CF3, 1-12C alkyl, 1-9C alkoxy, polyether, NO2, OH (optionally protected by acetyl or benzoyl), amino (optionally substituted by 1-12C alkyl, CONH-R24, acetyl or benzoyl), S(O)mR15, (CH2)p-COR16 or OR17; n = 1-9; q = 0 or 1; R13 = OR18, N(R19)(R20), aralkyl, aryl or heteroaryl; m, p = 0-2; R14 = 1-12C alkyl, CF3, aryl or aralkyl; R15 = 1-12C alkyl, aryl or aralkyl; R16 = 1-12C alkyl, OR21, N(R22)(R23), aryl or aralkyl; R17 = aryl or aralkyl; R18-R23 = H or 1-12C alkyl, or R19 + R20 and R22 + R23 = heterocyclyl, and R24 = phenyl, diphenylmethyl, diphenylpropyl, diphenylbutyl, biphenylyl, phenoxyphenyl, 9H-fluorenyl, 4-benzyloxyphenyl, 4-heptyloxyphenyl or 4-(6-methyl-2-benzothiazolyl)phenyl. Independent claims are also included for: (1) a composition (C) which comprises at least one (I) formulated into a carrier, and (2) a cosmetic composition which comprises at least one (I) formulated into a carrier.
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