Aromatic polyenic compounds and pharmaceutical/cosmetic compositions comprised thereof
AssigneeCentre International de Recherches Dermatologiques Galderma
InventorsJean-Michel Bernardon, Philippe Nedoncelle
Life of this patent
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Abstract
Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): ##STR1## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
Claims24
An aromatic polenic compound having the structural formula (I):
- ##STR4## in which R.sub.1 is a --CH.sub.3 radical, a radical --CH.sub.2 --O--R.sub.9, a radical --CH.sub.2 --O--CO--R.sub.10, or a radical --CO--R.sub.11, wherein R.sub.9, R.sub.10, and R.sub.11 are as defined below;
- R.sub.2 is a hydrogen atom or a lower alkyl radical having 1 to 6 carbon atoms;
- R.sub.3 is a hydrogen atom or a lower alkyl radical having 1 to 6 carbon atoms;
- R.sub.5 is a hydrogen atom or a lower alkyl radical having 1 to 6 carbon atoms;
- R.sub.7 and R.sub.8 independently are each (i) a hydrogen atom, (ii) a linear or branched alkyl radical having from 1 to 20 carbon atoms, (iii) a cycloaliphatic radical selected from the group consisting of 1-methylcyclohexyl and 1-adamantyl, (iv) a radical --O--CH.sub.2 --O--CH.sub.2 --CH.sub.2 --O--CH.sub.3, (v) a radical --O--R.sub.13, or (vi) a radical --S(O).sub.n R.sub.13, wherein R.sub.13 and n are as defined below, R.sub.4 and R.sub.6 together form, with the carbon atoms from which they depend and with the adjacent benzene ring, a naphthalene ring, and at least one of R.sub.7 and R.sub.8 has the above definition (ii) or (iii);
- R.sub.9 is a hydrogen atom or a lower alkyl radical having 1 to 6 carbon atoms;
- R.sub.10 is a lower alkyl radical having 1 to 6 carbon atoms;
- R.sub.11 is (a) a hydrogen atom, (b) a lower alkyl radical having 1 to 6 carbon atoms, (c) a radical of formula:
- ##STR5## in which R' and R" independently are each a hydrogen atom, a lower alkyl radical having 1 to 6 carbon atoms, a mono- or polyhydroxyalkyl radical respectively having 2 to 3 carbon atoms or 3 to 6 carbon atoms containing 2 to 5 hydroxyl groups, or an optionally substituted phenyl radical which if substituted, is substituted with at least one halogen atom, hydroxyl or nitro group, or (d) a radical --OR.sub.12, wherein R.sub.12 is a hydrogen atom, a linear or branched alkyl radical having from 1 to 20 carbon atoms, an alkenyl radical having 2 to 5 carbon atoms and at least one site of ethylenic unsaturation, a mono- or poly-hydroxyalkyl radical respectively having 2 to 3 carbon atoms or 3 to 6 carbon atoms and 2 to 5 hydroxyl groups, or an optionally substituted phenyl or radical benzyl or pheneyl radical wherein, if substituted, are substituted by at least one halogen atom, hydroxyl or nitro functional group;
- R.sub.13 is a hydrogen atom or a linear or branched alkyl radical having from 1 to 20 carbon atoms;
- and n is an integer equal to 0, 1 or 2;
- or a pharmaceutically/cosmetically acceptable salt or optical or geometric isomer thereof.
An aromatic polyenic compound selected from the group consisting of trans-7-3-(1-adamantyl)-4-hydroxyphenyl!-3,7-dimethyl-2,4,6-heptatrienoic acid;
- ethyl trans-7-3-(1-adamantyl)-4-methoxyphenyl!-3,7-dimethyl-2,4,6-heptatrienoat e;
- trans-7--3-(1-adamantyl)-4-methoxyphenyl!-3,7-dimethyl-2,4,6-heptatrienoi c acid;
- (2Z,4E,6E)-7-3-(1-adamantyl)-4-methoxyphenyl!-3,7-dimethyl-2,4,6-heptatri enoic acid;
- trans-5--7-(1-adamantyl)-6-methoxyethoxymethoxy-2-naphthyl!-3-methyl-2,4, -pentadienoic acid;
- trans-5--7-(1-adamantyl)-6-hydroxy-2-naphthyl!-3-methyl-2,4-pentadienoic acid;
- trans-5--7-(1-adamantyl)-6-methoxy-2-naphthyl!-3-methyl-2,4-pentadienoic acid;
- trans-5--7-(1-adamantyl)-6-propyloxy-2-naphthyl!-3-methyl-2,4-pentadienoi c acid;
- trans-7-3-(1-methylcyclohexyl)-4-hydroxy-phenyl!-3,7-dimethyl!-2,4,6-hept atrienoic acid;
- (2Z,4E,6E)-7-3-(1-methylcyclohexyl)-4-methoxyphenyl!-3,7-dimethyl-2,4,6-h eptatrienoic acid;
- trans-7-3-(1-adamantyl)-4-isopropyloxy-phenyl!-3,7-dimethyl-2,4,6-heptatr ienoic acid;
- trans-7-3-(1-adamantyl)-4-methoxyethoxymethoxyphenyl!-3,7-dimethyl-2,4,6- heptatrienoic acid;
- trans-7-3-(1-adamantyl)-4-methoxyphenyl!-7-methyl-2,4,6-heptatrienoic acid;
- trans-7-3-(1-adamantyl)-4-methoxyphenyl!-3,7-dimethyl-2,4,6-heptatrien-1- ol;
- trans-7-3-(1-adamantyl)-4-methoxyphenyl!-3,7-dimethyl-2,4,6-heptatrien-1- al;
- trans-N-ethyl-7-3-(1-adamantyl)-4-methoxy-phenyl!-3,7-dimethyl-2,4,6-hept atrienecarboxamide;
- trans-N-4-hydroxyphenyl-7-3-(1-adamantyl)-4-methoxyphenyl!-3,7-dimethyl-2 ,4,6-heptatrienecarboxamide;
- trans-7-(3-tert-butyl-4-methoxyethoxymethoxy-phenyl)-3,7-dimethyl-2,4,6-he ptatrienoic acid;
- ethyl trans-7-(3-tert-butyl-4-hydroxyphenyl)-3,7-dimethyl-2,4,6-heptatrienoate;
- ethyl trans-7-(3-tert-butyl-4-methoxyphenyl)-3,7-dimethyl-2,4,6-heptatrienoate;
- and ethyl trans-7-4-(1-adamantyl)-3-methoxyphenyl!-3,7-dimethyl-2,4,6-heptatrienoat e.
Dependencies are inferred from the claim text.