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US 8,283,378 B2Granted
Phenylurea inhibitors of the SOAT-1 enzyme and pharmaceutical/cosmetic compositions comprised thereof
AssigneeGalderma Research & Development
InventorThibaud Portal
Life of this patent
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Abstract
Novel phenylurea 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.
Claims22
A phenylurea compound having the following formula (I):
- in which:
- Y is O or S(O)p,
- p is equal to 0 or 2,
- n is equal to 0, 1 or 2
- R is a hydrogen atom, a (C1-C6)alkyl radical, a —CH2—NR6R7 radical, a —C(O)—NR6R7 radical or a —C(S)—NR6R7 radical, wherein R6 is a hydrogen atom or a (C1-C4)alkyl radical and R7 is a hydrogen atom, a phenyl or a cycloalkyl radical,
- R1 is a hydrogen atom, a (C1-C6)alkyl radical or an atom of chlorine, bromine or fluorine,
- R2 is a (C1-C6)alkyl radical,
- R3 is a hydrogen atom or a (C1-C6)alkyl radical,
- R4 and R′4 are identical and are each a (C1-C6)alkyl radical or alternatively R4 and R′4 are joined together and form, with the carbon atom from which they depend, a cycloalkyl group, an indanyl group, or a saturated heterocyclic group selected from the groups piperidine, tetrahydropyran, pyrrolidine, tetrahydrothiophene, tetrahydrofuran and azetidine, wherein the groups piperidine, pyrrolidine and azetidine are optionally substituted on the nitrogen atom with an R8, —C(O)R8 or —SO2R8 radical, wherein R8 is a (C1-C4)alkyl radical,
- R5 is an unsubstituted phenyl radical or a phenyl radical substituted with one to three substituents, which may be identical or different, selected from the atoms of chlorine, bromine or fluorine, the radicals (C1-C6)alkyl, cycloalkyl, trifluoromethyl, hydroxy, phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, (C1-C6)alkoxy, phenoxy, (C1-C6)alkylthio, trifluoromethoxy, or —NR9R10, wherein R9 and R10, which may be identical or different, represent, each independently, a hydrogen atom or a (C1-C4)alkyl radical, or a pharmaceutically acceptable salt, solvate or hydrate thereof.
7 more elements
Dependencies are inferred from the claim text.