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US 5,958,382 AGranted
4,4-dihydroxy-5-pyrazolinones and cosmetic/dermatological compositions comprised thereof
AssigneeSociete L'Oreal S.A.
InventorsLaurent Vidal, Gerard Malle, Jean-Claude Garson
Life of this patent
Estimating the term…
Abstract
Novel 4,4-dihydroxy-5-pyrazolinones having the structural formula (I): ##STR1## and cosmetic/dermatological formulations comprised thereof are useful for artificially coloring, e.g., tanning/browning, human skin and/or hair, and are well suited for imparting a healthy appearance to facial skin by enhancing the radiance of the complexion, while at the same time retaining transparency.
Claims16
A 4,4-dihydroxy-5-pyrazolinone compound having the structural formula (I):
- ##STR14## in which R.sub.1 is a hydrogen atom;
- a linear or branched C.sub.1 -C.sub.18 alkyl radical optionally substituted with a hydroxyl (OH), sulfonyl (SO.sub.3 H), carboxyl (COOH), C.sub.2 -C.sub.4 hydroxyalkyl or cyclopentyl radical;
- a cyclohexyl or cyclopentyl radical;
- a radical:
- ##STR15## wherein m is equal to 1, 2 or 3, n is equal to 1, 2 or 3, X is a hydrogen atom or a methyl radical, and Y is a methyl, hydroxyl or linear or branched C.sub.1 -C.sub.5 alkoxy radical;
- a radical --(CH.sub.2).sub.p --OR' wherein R' is a substituted or unsubstituted phenyl or naphthyl radical and p is equal to 1 or 2;
- a radical --(CH.sub.2).sub.q --R" wherein q is equal to 1, 2 or 3 and R" is a phenyl radical which is unsubstituted or substituted with not more than two radicals selected from among methyl, trifluoromethyl, methoxy and sulfonyl radicals, a naphthyl radical, a thienyl radical, a furyl radical, a pyridyl radical or a
- piperidyl radical, a radical:
- ##STR16## a radical:
- ##STR17## or a radical:
- ##STR18## a phenyl radical;
- a phenyl radical substituted with one or two nitro radicals;
- a phenyl radical substituted with a phenyl radical substituted with one or two nitro radicals;
- a phenyl radical substituted with one to five radicals selected from among --COOH, --CH.sub.2 COOH, --Cl, --Br, --F, --OH, --SO.sub.3 H, --CH.sub.2 OH, --OCF.sub.3, --CF.sub.3, --SO.sub.2 CH.sub.3, --SO.sub.2 NH.sub.2, --SO.sub.2 NHC.sub.2 H.sub.5, --SO.sub.2 NHCH.sub.2 CH.sub.2 OH, --CON(CH.sub.3).sub.2, --CON(C.sub.2 H.sub.5).sub.2, --CH.sub.2 N(CH.sub.3).sub.2, --.sub.CH2N (C2H.sub.5).sub.2, --NHCOCH.sub.3, --NHCOC.sub.2 H.sub.5, a C.sub.1 -C.sub.8 alkyl radical or a radical --ZR.sub.3 wherein Z is an oxygen or sulfur atom and R.sub.3 is a hydrogen atom or a linear or branched C.sub.1 -C.sub.18 alkyl radical;
- a naphthyl radical optionally substituted with an --SO.sub.3 H radical;
- a benzyl radical;
- a benzyl radical substituted with a --COOH, --OCH.sub.3 or --SO.sub.3 H radical;
- a pyridyl radical;
- a pyrimidinyl radical;
- a pyrazinyl radical;
- a triazinyl radical;
- a benzotriazolyl radical;
- a benzimidazolyl radical;
- a thienyl radical;
- an imidazolyl radical;
- a thiazolyl radical;
- a 1,2,4-triazolyl radical;
- an indazolyl radical;
- an indolyl radical, a quinolyl radical or an isoquinolyl radical;
- and R.sub.2 is a hydrogen atom;
- a linear or branched C.sub.1 -C.sub.18 alkyl radical optionally substituted with one or more hydroxyl radicals or C.sub.1 -C.sub.4 alkoxy radical;
- or a linear or branched C.sub.3 -C.sub.18 alkenyl radical optionally substituted with one or more hydroxyl radicals or C.sub.1 -C.sub.4 alkoxy radicals;
- a phenyl radical;
- a phenyl radical substituted with a halogen atom, a nitro radical or a trifluoromethyl radical;
- a phenyl radical substituted with not more than three radicals selected from among C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 dialkylamino and C.sub.1 -C.sub.2 alkylthio radicals;
- a benzyl radical;
- a benzyl radical substituted with a halogen atom, a C.sub.1 -C.sub.4 alkyl radical, a C.sub.1 -C.sub.4 alkoxy radical, a trifluoromethyl radical or a C.sub.1 -C.sub.4 dialkylamino radical;
- a radical --(CH.sub.2).sub.r --R.sub.4 wherein r is equal to 1, 2 or 3 and R.sub.4 is selected from among an --SO.sub.3 H radical, a C.sub.1 -C.sub.2 alkylthio radical or a benzylthio radical;
- a methoxycarbonyl or ethoxycarbonyl radical;
- a phenyl radical;
- a C.sub.1 -C.sub.4 alkoxy radical or a phenoxy radical optionally substituted with one or more halogen atoms;
- a C.sub.1 -C.sub.4 alkoxy radical;
- a phenoxy radical optionally substituted with one or more halogen atoms;
- a trifluoromethyl radical;
- an acetamido radical;
- a C.sub.1 -C.sub.4 dialkylamino radical;
- a carboxyl radical;
- a methoxycarbonyl radical;
- an ethoxycarbonyl radical;
- a radical --NH--CO--R.sub.5 wherein R.sub.5 is a linear or branched C.sub.1 -C.sub.18 alkyl radical or a C.sub.3 -C.sub.18 alkenyl radical;
- a thienyl radical;
- a furyl radical;
- a pyridyl radical or a pyrazolyl radical;
- or a halogen atom.
51 more elements
Dependencies are inferred from the claim text.