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US 2006/0148862 A1Published application
Novel compounds that modulate PPARy type receptors and cosmetic/pharmaceutical compositions comprised thereof
AssigneeGalderma Research & Development, S.N.C.
InventorsLaurence Clary, Etienne Thoreau, Michel Rivier, Jerome Aubert, Laurent Chantalat, Johannes Voegel
Life of this patent
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Abstract
Novel compounds having the general formula (I) below: are useful in a wide variety of applications 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 are formulated into cosmetic compositions.
Claims22
A compound having the following structural formula (I):
- in which:
- R1 is a radical of formula (a) or (b) below:
- R3 and R4 are as defined below;
- R2 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 or a radical of formula (CH2)m(NR5)n(C(O,N))pR6;
- R5, R6, m, n and p are as defined below;
- R3 is a radical selected from among the following formulae:
- R7, R8, V, W and Y are as defined below;
- R4 is an alkyl radical having from 1 to 12 carbon atoms, a radical OR9 or a radical SR9 or NHR9;
- R5 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, with the proviso that when Y is an nitrogen atom, then formula (e) is not substituted by a radical R7;
- R6 and R8, which may be identical or different, are each:
- a radical O—(CH2)v—R10,
- a hydroxyl radical, an alkyl radical having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical, a heterocyclic radical,
- a radical
- or a radical NR′(CH2)vR10;
- R10, R′, R″ and v are as defined below;
- R9 is an alkyl radical having from 1 to 12 carbon atoms, or a radical selected from among those of the following formulae:
- (h) α-amino acid N-protected with standard amine-protecting groups;
- R11, Q and p are as defined below;
- m has the values 0, 1 or 2;
- n and p have the values 0 or 1;
- Q is an oxygen or sulfur atom or NR5;
- V is an oxygen, a nitrogen or sulfur atom;
- W is a nitrogen atom or a radical C—R5;
- Y is a nitrogen atom or a carbon atom;
- Z is an oxygen, nitrogen or sulfur atom;
- v has the values 1, 2 or 3;
- R10 is an alkyl radical having from 1 to 12 carbon atoms, an aryl, aralkyl, heteroaryl or heterocyclic radical, a radical NH—CO—R12, a radical NH—CO—O—R12 or C—R12R13 or a radical N—R12R13, wherein R12 and R13 are as defined below;
- R′ is a hydrogen atom, an alkyl radical having from 1 to 12 carbon atoms, a heteroaryl radical or a heterocyclic 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 halogens, a heteroaryl radical, a heterocyclic radical, a radical (CH2)v—R10, or a radical NHR10 or NR10R10;
- R11 is a hydrogen atom, an alkyl radical having from 1 to 12 carbon atoms, an aryl radical, an aralkyl radical, a heteroaryl radical, a heterocyclic radical or a radical (CO)s(Z)tR10 with s and t having the values 0, 1 or 2;
- R12 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;
- R13 is a hydrogen atom or an alkyl radical having from 1 to 12 carbon atoms;
- X is a radical having the following structure:
- —(CH2)z—NR14—C(T)-(D)w-
- wherein D, z, T and R14 are as defined below;
- T is an oxygen or sulfur atom;
- D is an oxygen or sulfur atom, a radical —NR15 or a radical CH2, wherein R15 is as defined below;
- z has the values 0 or 1;
- w has the values from 0 to 6;
- and
- R14 and R15 are each a hydrogen atom or an alkyl radical having from 1 to 12 carbon atoms,
- Ar1 and Ar2, which may be identical or different, are each an optionally substituted aromatic radical of one of the formulae:
- wherein A is an S or O atom or a radical N—R13, with the proviso that, when Ar1 or Ar2 is a phenyl radical, then Ar2 or Ar1 is necessarily a heteroaryl radical,
- and the optical and geometrical isomers and also the salts thereof.
41 more elements
Dependencies are inferred from the claim text.