Novel 4-phenylimidazole-2-thione tyrosinase inhibitors and pharmaceutical/cosmetic applications thereof
AssigneeGalderma Research & Development
InventorsJean Guy BOITEAU, Corinne Millois Barbuis, Sandrine TALANO
Life of this patent
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Abstract
Novel 4-phenylimidazole-2-thione tyrosinase inhibiting compounds corresponding to the following general formula (I): formulated into pharmaceutical or cosmetic compositions are useful for the treatment or prevention of pigmentary disorders, or for preventing and/or treating signs of skin aging, and/or for body or hair hygiene.
Claims17
A 4-phenylimidazole-2-thione tyrosinase inhibiting compound of general formula (I):
- in which:
- a) when R2=H, then R1 is:
- a C2-C7 alkyl radical, with the exception of isopropyl, n-propyl and tert-butyl,
- a hydroxymethyl, trifluoromethoxy or difluoromethoxy radical,
- a C3-C7 cycloalkyl radical, with the proviso that one of the carbon atoms of the ring may optionally be replaced by an oxygen or sulfur atom,
- a C4-C9 cycloalkylalkyl radical,
- a morpholinyl, thiomorpholinyl, piperazinyl or N-methylpiperazinyl group,
- a carboxyl substituent,
- a (C1-C4 alkoxy)carbonyl group, or
- a C2-C6 alkoxy radical, with the exception of n-butoxy,
- b) when R1=H, then R2 is:
- a C1-C7 alkyl radical,
- a trifluoromethoxy, difluoromethoxy or cyano radical,
- a C3-C7 cycloalkyl radical, with the proviso that one of the carbon atoms of the ring may optionally be replaced by an oxygen or sulfur atom,
- a C4-C9 cycloalkylalkyl radical,
- a (C1-C4 alkoxy)carbonyl radical,
- a C1-C6 alkoxy radical, with the exception of n-propoxy,
- c) and, when R2 is in the ortho position with respect to R1, then R1 and R2, which may be identical or different, are each a C1-C5 alkyl radical or together form a 5- or 6-sided hydrocarbon ring, in which 1 or 2 carbon atom(s) are optionally replaced by 1 or 2 oxygen atom(s),
- and the salts and tautomeric forms thereof.
A regime or regimen for the treatment and/or prevention of hyperpigmentary disorders, comprising topically applying onto the skin, mucous membranes and/or superficial body growths of an individual in need of such treatment, a thus effective amount of at least one compound of general formula (I):
- in which:
- a) when R2=H, then R1 is:
- a C2-C7 alkyl radical, with the exception of isopropyl, n-propyl and tert-butyl,
- a hydroxymethyl, trifluoromethoxy or difluoromethoxy radical,
- a C3-C7 cycloalkyl radical, with the proviso that one of the carbon atoms of the ring may optionally be replaced by an oxygen or sulfur atom,
- a C4-C9 cycloalkylalkyl radical,
- a morpholinyl, thiomorpholinyl, piperazinyl or N-methylpiperazinyl group,
- a carboxyl substituent,
- a (C1-C4 alkoxy)carbonyl radical or
- a C2-C6 alkoxy radical, with the exception of n-butoxy,
- b) when R1=H, then R2 is:
- a C1-C7 alkyl radical,
- a trifluoromethoxy, difluoromethoxy or cyano radical,
- a C3-C7 cycloalkyl radical, with the proviso that one of the carbon atoms of the ring may optionally be replaced by an oxygen or sulfur atom,
- a C4-C9 cycloalkylalkyl radical,
- a (C1-C4 alkoxy)carbonyl radical,
- a C1-C6 alkoxy radical, with the exception of n-propoxy,
- c) and, when R2 is in the ortho position with respect to R1, then R1 and R2, which may be identical or different, are each a C1-C5 alkyl radical or together form a 5- or 6-sided hydrocarbon ring, with the proviso that 1 or 2 carbon atom(s) are optionally replaced by 1 or 2 oxygen atom(s),
- and the salts and tautomeric forms thereof, formulated into a topically applicable, pharmaceutically/cosmetically acceptable vehicle therefor.
A topically applicable pharmaceutical composition useful for the treatment and/or prevention of hyperpigmentary disorders, comprising at least one compound of general formula (I):
- in which:
- a) when R2=H, then R1 is:
- a C2-C7 alkyl radical, with the exception of isopropyl, n-propyl and tert-butyl,
- a hydroxymethyl, trifluoromethoxy or difluoromethoxy radical,
- a C3-C7 cycloalkyl radical, with the proviso that one of the carbon atoms of the ring may optionally be replaced by an oxygen or sulfur atom,
- a C4-Cg cycloalkylalkyl radical,
- a morpholinyl, thiomorpholinyl, piperazinyl or N-methylpiperazinyl group,
- a carboxyl substituent,
- a (C1-C4 alkoxy)carbonyl radical or
- a C2-C6 alkoxy radical, with the exception of n-butoxy,
- b) when R1=H, then R2 is:
- a C1-C7 alkyl radical,
- a trifluoromethoxy, difluoromethoxy or cyano radical,
- a C3-C7 cycloalkyl radical, with the proviso that one of the carbon atoms of the ring may optionally be replaced by an oxygen or sulfur atom,
- a C4-Cg cycloalkylalkyl radical,
- a (C1-C4 alkoxy)carbonyl radical,
- a C1-C6 alkoxy, with the exception of n-propoxy,
- c) and, when R2 is in the ortho position with respect to R1, then R1 and R2, which may be identical or different, are each a C1-C5 alkyl radical or together form a 5- or 6-sided hydrocarbon ring, with the proviso that 1 or 2 carbon atom(s) are optionally replaced by 1 or 2 oxygen atom(s),
- and the salts and tautomeric forms thereof, formulated into a topically applicable, pharmaceutically acceptable vehicle therefor.
Dependencies are inferred from the claim text.