Bicyclic aromatic compounds and pharmaceutical/cosmetic compositions comprised thereof
View Patent ↗Novel pharmaceutically/cosmetically-active bicyclic aromatic compounds having the structural formula (I): in which Ar 1 is a radical having one of the structural formulae (a)-(c): and Ar 2 , X 1 , R 1 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are as defined in the specification.
1. The bicyclic aromatic compound, which is: 3-(3′,5′-di-tert-butyl-2′-methoxy-3-biphenylyl) acrylic acid; 3-(2′-benzyloxy-3′,5′-di-tert-butyl-6-hydroxy-3-biphenylyl) acrylic acid; 3-(3′-5′-di-tert-butyl-6-hydroxy-2′-pentyloxy-3-biphenylyl) acrylic acid; 3-(3′,5′-di-tert-butyl-6-hydroxy-2′-methoxy-3-biphenylyl) acrylic acid; 3-[3-(3-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxymethoxyphenyl] acrylic acid; 3-[3-(3-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-hydroxyphenyl] acrylic acid; [4-methoxymethoxy-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl) phenyl]propynoic acid; 3-[3-(3-propyloxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxymethoxyphenyl]acrylic acid; 3-[3-(3-pentyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxymethoxyphenyl]acrylic acid; 3-(5′-adamantan-1-yl-4′-methoxy-2′-methyl-3-biphenylyl)acrylic acid; 3-(5′-adamantan-1-yl-6-hydroxy-4′-methoxy-2′-methyl-3-biphenylyl)acrylic acid; 3-(5′-adamantan-1-yl-4′-methoxy-6-methoxymethoxy-2′-methyl-3-biphenylyl)acrylic acid; 3-{4-methoxy-3-[3-(3-methoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{4-methoxy-3-[3-(4-methoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{3-[3-(6-hydroxyhexyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid: 3-{3-[3-(7-hydroxyheptyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid; 3-{3-[3-(5-hydroxypentyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid; 3-{3-[3-(3-hydroxypropyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid; 3-[3-(1-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]acrylic acid; 3-(3′-adamantan-1-yl-4′-hydroxy-3-biphenylyl)acrylic acid; 5-[4-methoxy-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]-3-methylpenta-2,4-dienoic acid; 5-[4-methoxymethoxy-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]-3-methylpenta-2,4-dienoic acid; 5-[4-hydroxy-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]-3-methylpenta-2,4-dienoic acid; 3-{3-[3-(5-tert-butoxycarbonylpentyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid; 3-{3-[3-(7-tert-butoxycarbonylheptyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid; 3-{3-[3-(7-carboxyheptyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid; 3-{3-[3-(5-carboxypentyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid; 3-{3-[3-(5-carbamoylpentyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid; 3-{3-[3-(7-carbamoylheptyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylic acid; 3-{4-methoxy-3-[5,5,8,8-tetramethyl-3-(2-morpholin-4-ylethoxy)-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{4-methoxy-3-[5-5,8,8-tetramethyl-3-(2-piperidin-1-ylethoxy)-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{4-methoxy-3-[3-(2-methoxymethoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{4-methoxy-3-[3-(3-methoxymethoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{4-methoxy-3-[3-(4-methoxymethoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{4-methoxy-3-[3-(3-hydroxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-[4-fluoro-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]acrylic acid; 3-{4-hydroxy-3-[3-(3-methoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{4-hydroxy-3-[3-(4-methoxybenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{4-hydroxy-3-[3-(4-fluorobenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-{4-hydroxy-3-[3-(4-chlorobenzyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]phenyl}acrylic acid; 3-[4-hydroxy-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]acrylic acid; 3-(3′,5′-di-tert-butyl-6-hydroxy-2′-propyloxy-3-biphenylyl)acrylic acid; 3-(3′,5′-di-tert-butyl-6-hydroxy-2′-butyloxy-3-biphenylyl)acrylic acid; 3-(2′-butoxy-3′,5′-di-tert-butyl-6-methoxy-3-biphenylyl)acrylic acid; 3-(3′, 5′-di-tert-butyl-6-methoxy-2′-propoxy-3-biphenylyl)acrylic acid; 3-[4-hydroxy-3-(5,5,8,8-tetramethyl-4-propoxy-5,6,7,8-tetrahydro-2-naphthyl)phenyl]acrylic acid; 3-[3-(3-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl]acrylic acid; ethyl 3-[3-(3-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl]acrylate; 3-methyl-5-[3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]penta-2,4-dienoic acid; 3-[3-(3-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl]prop-2-en-1-ol; 3-[3-(3-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl]propenal; N-ethyl 3-[3-(3-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl]acrylamide; 3-[3-(3-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl]-1-morpholin-4-yl-propenone; N-(4-hydroxyphenyl)-3-[3-(3-benzyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-methoxyphenyl]acrylamide; 5-(5′-adamantan-1-yl-4′-methoxy-2′methyl-3-biphenylyl)-3-methylpenta-2,4-dienoic acid; 5-[4-methoxymethoxy-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]-3-methylpenta-2,4-dienoic acid; 5-[4-hydroxy-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]-3-methylpenta-2,4-dienoic acid; 4-[3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]penta-2,4dienoic acid; 5-(3′,5′-di-tert-butyl-2′-methoxy-3-biphenylyl)-3-methylpenta-2,4-dienoic acid; 5-(3′-5′-di-tert-butyl-2′-propoxy-3biphenylyl)-3-methylpenta-2,4-dienoic acid; 5-(2′-butoxy-3′,5′-di-tert-butyl-3-biphenylyl)-3-methylpenta-2,4-dienoic acid; 5-(2′-butoxy-3′,5′-di-tert-butyl-6-hydroxy-3-biphenylyl)-3-methylpenta-2,4-dienoic acid; 5-(3′,5′-di-tert-butyl-6-hydroxy-2′-propoxy-3-biphenylyl)-3-methylpenta-2,4-dienoic acid; or 5-(3′,5′-di-tert-butyl-6-hydroxy-2′-methoxy-3-biphenylyl)-3-methylpenta-2,4-dienoic acid.