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US 7,452,878 B2Granted
Biaromatic compounds which activate PPARγ type receptors and cosmetic/pharmaceutical compositions comprised thereof
AssigneeGalderma Research & Development
InventorsLaurence Clary, Claire Bouix-Peter, Michel Rivier, Pascal Collette, Andre Jomard
Life of this patent
Estimating the term…
Abstract
Novel biaromatic compounds having the structural formula (I) below: are formulated into pharmaceutical compositions suited for administration in human or veterinary medicine (in dermatology, and also in the fields of cardiovascular diseases, immune diseases and/or diseases associated with lipid metabolism), or, alternatively, into cosmetic compositions.
Claims15
A biaromatic compound having the structural formula (I):
- in which:
- R is a hydrogen atom;
- R1 is a
- R2 is a
- wherein R9 is as defined below;
- R3 is a hydrogen atom;
- R4 is an alkyl radical having from 1 to 12 carbon atoms;
- R5 is a hydrogen atom, an alkyl radical having from 1 to 12 carbon atoms, an alkoxy radical having from 1 to 7 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical, a heterocyclic radical or a group (CO)s(Z)tR7, wherein Z, R7, s and t are as defined below;
- s and t have the values 0, 1 or 2;
- Z is an oxygen, nitrogen or sulfur atom;
- R7 is a hydrogen atom, an alkyl radical having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical or a heterocyclic radical;
- R9 is a radical O—(CH2)v—R10, a hydroxyl radical, an alkoxy radical having from 1 to 7 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical, a heterocyclic radical, or the radical:
- wherein R10, R′ and R″ are as defined below;
- R′ is a hydrogen atom, an alkyl radical having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical or a heterocyclic radical or a hydroxyl radical;
- R″ is a hydrogen atom, an alkyl radical having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, optionally substituted with one or more halogen atoms, a heteroaryl radical, a heterocyclic radical or a radical (CH2)v—R10, wherein R10 and v are as defined below;
- R10 is an aryl, aralkyl or heteroaryl radical, a heterocyclic radical, the radical NH—CO—R11, the radical NH—CO—O—R11, the radical N—R11R12 or the radical CH—R11R12;
- v has the values 1, 2 or 3;
- R11 is a hydrogen atom, an alkyl radical having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical or a heterocyclic radical;
- R12 is a hydrogen atom or an alkyl radical having from 1 to 3 carbon atoms;
- A is a radical having the following structure:
- —(CH2)z—(N—R13)y—(CO)x-(D)w—
- wherein D, w, x, y, z and R13 are as defined below;
- D is an oxygen or sulfur atom, a radical —NR14 or a CH2 radical;
- R14 is as defined below;
- x, y and z, which may be identical or different, have the values 0 or 1;
- w has a value from 0 to 6 with the proviso that w is equal to 0 or 1 when D is oxygen, and
- R13 and R14 are each a hydrogen atom or an alkyl radical having from 1 to 12 carbon atoms;
- R15 is a hydrogen atom;
- but other than the compounds of formula (II) below:
- in which:
- R3=OMe and R′3=R″3=H;
- R3=OMe, R′3=OMe and R″3=H;
- and
- R3=H and R′3=R″3=OMe;
- also other than the compounds of formula (III) below:
- in which:
- z=1 and x=0;
- and
- z=0 and x=1;
- and also other than the compounds of formula (IV) below:
- in which:
- p=1, X is an oxygen atom, R5 is a benzyl radical and R4 is a 2-benzimidazole or 4-pyridine radical;
- p=1, X is an oxygen atom, R5 is an ethyl radical and R4 is a 2-pyridine, 3-pyridine, 4-pyridine or methyl radical;
- p=1, X is an oxygen atom, R4 is a propyl radical and R5 is an ethyl, CH2-isopropyl, CH2-tert-butyl, cyclopentyl, 4-methoxyphenyl or benzyl radical;
- p=1, X is an NH radical, R4 is a propyl radical and R5 is a hydrogen atom or a benzyl radical;
- p=1, X is an NH radical, and R4 and R5 are each a cyclohexyl radical;
- and
- p=0, R4 is an ethyl radical and R5 is a 4-methoxyphenyl radical.
45 more elements
Dependencies are inferred from the claim text.