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US 8,044,082 B2Granted
N-phenylacetamide inhibitors of the enzyme SOAT-1 and pharmaceutical/cosmetic compositions comprised thereof
AssigneeGalderma Research & Development
InventorsThibaud Portal, Laurence Dumais, Jérôme Aubert, Laurent Lamy
Life of this patent
Estimating the term…
Abstract
Novel N-phenylacetamide compounds of formula (I): and cosmetic and pharmaceutical compositions containing same are useful for treating disorders of the sebaceous gland, e.g., acne, or have cosmetic applications.
Claims24
An N-phenylacetamide compound having the following general formula (I):
- in which:
- Y is C(0) or CH2,
- R1 is a (C1-C6)alkyl radical,
- R2 is a hydrogen, chlorine, fluorine or bromine atom, or a (C1-C6)alkyl radical,
- R3 is a hydrogen atom, a (C1-C6)alkyl radical, or a —WNR6R7 radical wherein W is C(O), C(S) or CH2, R6 is a hydrogen atom or a (C1-C6)alkyl radical and R7 is a hydrogen atom, a cycloalkyl radical or a phenyl radical,
- R4 and R′4 are identical and are each a (C1-C6)alkyl radical or else R4 and R′4 are bonded to one another and together form, with the carbon atom from which they depend, a cycloalkyl group,
- R5 is a group selected from among:
- (i) an unsubstituted phenyl radical or a phenyl radical substituted by one to three identical or different substituents selected from among the atoms fluorine, chlorine, iodine or bromine, and the radicals (C1-C6)alkyl, hydroxymethyl, mono-, di- or trifluoromethyl, hydroxyl, phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, (C1-C6)alkoxy, phenoxy, benzyloxy, mono-, di- or trifluoromethoxy,
- (ii) a (C1-C12)alkyl radical, optionally substituted by one or more hydroxyl groups, or fluorine, chlorine, iodine or bromine atoms,
- (iii) a cycloalkyl radical or a -(CH2)m-cycloalkyl radical in which m is equal to 1, 2 or 3,
- (iv) an aralkyl radical —(CH2)n-Ar with n equal to 1, 2 or 3 and Ar is an unsubstituted phenyl radical, unsubstituted naphthyl, or a phenyl radical substituted by one to three identical or different substituents selected from among the atoms fluorine, chlorine, iodine and bromine, and the radicals (C1-C6)alkyl, hydroxymethyl, mono-, di- or trifluoromethyl, hydroxyl, phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl, (C1-C6)alkoxy, phenoxy, benzyloxy, mono-, di- or trifluoromethoxy, and the pharmaceutically acceptable salts, conformers and rotamers thereof.
8 more elements
Dependencies are inferred from the claim text.