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
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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.
Claims18
A biaromatic compound having the structural formula (I):
- in which:
- R1 is an alkyl radical having from 1 to 12 carbon atoms, or a radical selected from among those of formulae a)-c):
- b) —(CH2)m—(CO)n—(X)p—(CH2)q—R5 or
- c) an α-amino acid N-protected with an amine-protecting group,
- wherein R5, X, m, n, p and q are as defined below;
- R2 is a radical of formula(a)
- wherein R7 is as defined below;
- R3 is a hydrogen atom, a halogen atom, an alkyl radical having from 1 to 12 carbon atoms, a hydroxyl radical, an alkoxy radical having from 1 to 7 carbon atoms, an aralkoxy radical, an aryloxy radical, a polyether radical, a nitro radical, an amino radical optionally substituted with one or more alkyl radicals having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical or a heterocyclic radical;
- R4 is an alkyl radical having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical, a heterocyclic radical, a 9-fluorenylmethyl radical, a radical —(CH2)a—N—R12)b—(CO)c—R6 or a radical —(CH2)a—(N—R12)b—(CNR15)c—R6, wherein R6, R12, R15, a, b and c are as defined below;
- 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 aralkoxy radical, an aryloxy radical, an aryl radical, an aralkyl radical, a heteroaryl radical, a heterocyclic radical or a group (CO)s(Z)tR6, wherein Z, R6, s and t are as defined below;
- a, b, c, m, n, p, q, s and t have the values 0, 1 or 2;
- X is an oxygen atom, a sulfur atom or NR6, wherein R6 is as defined below;
- Z is an oxygen atom, a nitrogen atom or a sulfur atom;
- R6 and R7, which may be identical or different, are each 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;
- R15 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;
- R10 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;
- R14 is a halogen atom;
- A is a radical having the following structure:
- —(CH2)z—(N—R12)y—(CO)x—(D)w or —(CH2)z—(N—R12)y—(CS)x-(D)w,
- wherein D, w, x, y, z and R12 are as defined below;
- D is an oxygen atom, a sulfur atom, a radical —NR13 or a CH2 radical;
- wherein w, x, y, z and R13 are as defined below;
- w, x, y and z, which may be identical or different, have the values 0 or 1, with the proviso that the sum x+y+z+w is greater than 2, and when x=0 then y or w=0;
- R12 and R13 are each a hydrogen atom or an alkyl radical having from 1 to 12 carbon atoms, and the optical isomers and salts and mixtures thereof.
A cosmetic composition useful for body and/or hair hygiene, comprising a thus effective amount of a biaromatic compound having the structural formula (I):
- in which:
- R1 is an alkyl radical having from 1 to 12 carbon atoms, or a radical selected from among those of formulae a)-c):
- b) —(CH2)m—(CO)n—(X)p—(CH2)q—R5 or
- c) an α-amino acid N-protected with an amine-protecting group,
- wherein R5, X, m, n, p and q are as defined below;
- R2 is a radical of formula(a)
- wherein R7 is as defined below;
- R3 is a hydrogen atom, a halogen atom, an alkyl radical having from 1 to 12 carbon atoms, a hydroxyl radical, an alkoxy radical having from 1 to 7 carbon atoms, an aralkoxy radical, an aryloxy radical, a polyether radical, a nitro radical, an amino radical optionally substituted with one or more alkyl radicals having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical or a heterocyclic radical;
- R4 is an alkyl radical having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical, a heterocyclic radical, a 9-fluorenylmethyl radical, a radical —(CH2)a—(N—R12)b—(CO)c—R6 or a radical —(CH2)a—(N—R12)b—(CNR15)c—R6, wherein R6, R12, R15, a, b and c are as defined below;
- 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 aralkoxy radical, an aryloxy radical, an aryl radical, an aralkyl radical, a heteroaryl radical, a heterocyclic radical or a group (CO)s(Z)tR6, wherein Z, R6, s and t are as defined below;
- a, b, c, m, n, p, q, s and t have the values 0, 1 or 2;
- X is an oxygen atom, a sulfur atom or NR6, wherein R6 is as defined below;
- Z is an oxygen atom, a nitrogen atom or a sulfur atom;
- R6 and R7, which may be identical or different, are each 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;
- R15 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;
- R10 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;
- R14 is a halogen atom;
- A is a radical having the following structure:
- —(CH2)z—(N—R12)y—(CO)x-(D)w or —(CH2)z—(N—R12)y—(CS)x—(D)w,
- wherein D, w, x, y, z and R12 are as defined below;
- D is an oxygen atom, a sulfur atom, a radical —NR13 or a CH2 radical;
- wherein w, x, y, z and R13 are as defined below;
- w, x, y and z, which may be identical or different, have the values 0 or 1, with the proviso that the sum x+y+z+w is greater than 2, and when x=0, then y or w=0;
- R12 and R13 are each a hydrogen atom or an alkyl radical having from 1 to 12 carbon atoms, and the optical isomers and salts and mixtures thereof,
- formulated into a cosmetically acceptable support therefor.
Dependencies are inferred from the claim text.