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US 7,592,478 B2Granted
Ligand antagonists of RAR receptors and pharmaceutical/cosmetic applications thereof
AssigneeGalderma Research & Development
InventorsPhilippe Diaz, Catherine Raffin, Thibaud Biadatti
Life of this patent
Estimating the term…
Abstract
Novel ligand antagonists of the RAR receptors have the following structural formula (I): in which A is a CH2, CHOH, C═O or C═N—OH radical or a sulfur or selenium atom; B is a radical selected from among those of formulae (a) to (f): and Ar is a radical selected from among those of formulae (g) to (i):
Claims37
A compound having the following structural formula (I):
- in which A is a CH2 radical;
- B is a radical selected from among those of formulae (a) to (f):
- Ar is a radical selected from among those of formulae (g) to (i):
- wherein R3 is as defined below;
- R1 is a radical —OH, —OR4, —NHR5 or NR5R6, wherein R4, R5 and R6 are as defined below;
- R2 is a hydrogen, fluorine, chlorine or bromine atom, a linear or branched alkyl radical having 1 to 5 carbon atoms, a CF3, OR7, SR7, NHR8, NR8R9, 2-naphthyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiophenyl, CH2OR10 or CH2NR11R12 radical or a phenyl radical which is unsubstituted or substituted with at least one fluorine atom or with a methyl, ethyl, isopropyl, tert-butyl or CF3 radical, wherein R7, R8, R9, R10, R11 and R12 are as defined below;
- R3 is a hydrogen, fluorine or chlorine atom or a radical OH, OR13, CF3 or NR14R15, wherein R13, R14 and R15 are as defined below;
- R4 is a linear or branched alkyl radical having 1 to 4 carbon atoms;
- R5 is a hydrogen atom, an OH group or a linear or branched alkyl radical having 1 to 4 carbon atoms;
- R6 is a linear or branched alkyl radical having 1 to 4 carbon atoms;
- R7 is a hydrogen atom, a linear or branched alkyl radical having 1 to 6 carbon atoms, a radical CH2OR16 or a benzyl radical which is unsubstituted or substituted with at least one halogen atom, or with a methyl, ethyl, isopropyl, tert-butyl or CF3 radical, wherein R16 is as defined below;
- R8, R9, R11, R12, R14 and R15, which may be identical or different, are each a hydrogen atom, a linear or branched alkyl radical having 1 to 4 carbon atoms, (C═O)—R17 or (C═O)—OR17, wherein R17 is as defined below;
- R10 is a linear or branched alkyl radical having 1 to 4 carbon atoms or a benzyl or phenyl radical optionally substituted by one halogen atom, or by one alkyl radical having 1 to 3 carbon atoms;
- R13 is a methyl, ethyl or acetyl radical;
- R16 is a methyl, ethyl or CH2CH2OCH3 radical;
- R17 is a hydrogen atom or a linear or branched alkyl radical having 1 to 4 carbon atoms;
- and the stereoisomers and optical or geometrical isomers or mixtures thereof, and the salts obtained with a pharmaceutically acceptable acid or base.
14 more elements
Dependencies are inferred from the claim text.