WO2023249912A1 - Composition cosmétique comprenant des antioxydants hydrophiles et des composés de thiopyridinone - Google Patents

Composition cosmétique comprenant des antioxydants hydrophiles et des composés de thiopyridinone Download PDF

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Publication number
WO2023249912A1
WO2023249912A1 PCT/US2023/025678 US2023025678W WO2023249912A1 WO 2023249912 A1 WO2023249912 A1 WO 2023249912A1 US 2023025678 W US2023025678 W US 2023025678W WO 2023249912 A1 WO2023249912 A1 WO 2023249912A1
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Prior art keywords
alkyl group
branched
formula
linear
composition according
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PCT/US2023/025678
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English (en)
Inventor
Nicholas David STEBBINS
David Chan
Wenyan Xu
Lixuan KE
Rui Huang
Jun Wu
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L'oreal
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Priority claimed from US17/844,939 external-priority patent/US20230404884A1/en
Priority claimed from PCT/CN2022/100256 external-priority patent/WO2023245459A1/fr
Priority claimed from FR2211489A external-priority patent/FR3141623A1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2023249912A1 publication Critical patent/WO2023249912A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the present disclosure relates to cosmetic compositions comprising a combination of hydrophilic antioxidants and its derivatives with compounds of Thiopyridinone type.
  • thiopyridinone compounds exhibit good depigmenting activity, even at low concentration, see for example WO2012080075 and WO2017/102349.
  • the thiopyridinone compound can show strong depigmenting or brightening effects by reducing the production of melanin.
  • Vitamin C is a potent antioxidant that can be used topically in dermatology to treat and prevent changes associated with photoageing, hyperpigmentation, etc. Vitimin C is very unstable and difficult to formulate and deliver into the dermis. Research has been ongoing to develop stable compositions that deliver high amounts of ascorbic acid to the skin.
  • the present disclosure relates to cosmetic compositions that are unique in comparison to conventional cosmetic compositions because they contain an association of two molecules, compounds of Thiopyridinone type (I) or (I') and hydrophilic antioxidants, that show stabilization of the hydrophilic antioxidants as well as a co- stabilization effect
  • the inventors have discovered that combining compounds of Thiopyridinone type and hydrophilic antioxidants improves the stability of both.
  • the cosmetic compositions typically include: i) at least one compound selected from compounds of formula (I) and tautomer of formula (I') herein below; and their optical isomers, racemates, and/or solvates such as hydrates, alone or as a mixture :
  • R 1 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 10 or branched C 3 -C 10 alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 ii) -S-R 3 ;
  • R 2 denotes a radical chosen from: a) a hydrogen atom; b) a saturated hydrocarbonated group linear C 1 -C 12 or branched C 3 - C 12 or cyclic C 3 -C 8 , optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 ii) -S-R 3 iii) -C(O)-O-R 3 ; iv) a C 5 -C 12 aryl group optionally substituted with one or more hydroxyls and/or with one or more C 1 -C 8 alkoxy radicals; c) a C 5 -C 12 aryl group optionally substituted with one or more hydroxyls and/or with one or more C 1 -C 8 alkoxy radicals
  • R 3 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 10 or branched C 3 -C 10 alkyl group; one or more hydrophilic antioxidants.
  • the inventors surprisingly and unexpectedly discovered that when compounds of thiopyridinone type and one or more ascorbic hydrophilic antioxidants are present in the composition in amounts sufficient, the association produced a co-stability of the compounds of thiopyridinone type and the one or more hydrophilic antioxidants.
  • the combination between compounds of thiopyridinone type and ascorbic acid or a stabilized derivative thereof can not only achieve the depigmenting or brightening effect desired, but also promote the antioxidizing effect.
  • the one or more hydrophilic antioxidants is typically present in the cosmetic composition in an amount of from about 0.1 to about 20 wt.%, based on the total weight of the cosmetic composition.
  • the amount of hydrophilic antioxidants is higher than 5 wt.%, for example from about 6 wt.% to about 15 wt.%, from about 8 wt.% to about 15 wt.%, from about 9 wt.% to about 15 wt.%, or from about 10 wt.% to about 15 wt.%, based on the total weight of the composition.
  • the one or more hydrophilic antioxidants is present from about 1 to about 15 wt.%, based on the total weight of the cosmetic composition.
  • the one or more hydrophilic antioxidants is preferably chosen from acid ascorbic and its derivatives.
  • the compound i) is typically present in the cosmetic compositions in an amount of from about 0.01 to about 10 wt.%, based on the total weight of the cosmetic composition. In some cases, the amount of compound i) is present in an amount of from about 0.1 to about 5 wt.%, based on the total weight of the cosmetic composition. In some embodiments, the compound i) is typically present in the cosmetic compositions in an amount of from about 0.5 to about 3 wt.%, based on the total weight of the cosmetic composition
  • the cosmetic compositions may include one or more fatty compounds.
  • the cosmetic compositions may include one or more polymers.
  • the cosmetic compositions may include one or more emulsifiers.
  • the cosmetic composition may have a pH ranging from about 4.5 to about 6.5, preferably from about 5 to about 6.
  • the cosmetically acceptable carrier system is selected from oil-in-water emulsions, water -in-oil emulsions, silicone in water emulsions, dispersions, micellar waters, biphasic compositions, foams, and alcohol-based carriers.
  • the cosmetic compositions may include: i) from about 0.01 to about 10 wt.% of at least one compound selected from compounds of formula (I) and tautomer of formula (I') herein below; and their optical isomers, racemates, and/or solvates such as hydrates, alone or as a mixture :
  • R 1 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 10 or branched C 3 -C 10 alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 ii) -S-R 3 ;
  • R 2 denotes a radical chosen from: a) a hydrogen atom; b) a saturated hydrocarbonated group linear C 1 -C 12 or branched C 3 - C 12 or cyclic C 3 -C 8 , optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 ii) -S-R 3 iii) -C(O)-O-R 3 ; iv) a C 5 -C 12 aryl group optionally substituted with one or more hydroxyls and/or with one or more C 1 -C 8 alkoxy radicals; c) a C 5 -C 12 aryl group optionally substituted with one or more hydroxyls and/or with one or more C 1 -C 8 alkoxy radicals
  • R 3 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 10 or branched C 3 -C 10 alkyl group; ii) from about 0.1 to about 20 wt.% of one or more ascorbic acid and its derivatives; and iii) a cosmetic suitable carrier; wherein the i) compound of thiopyridininone type and the ii) one or more ascorbic acid and its derivatives are present in the composition in amounts sufficient to produce stability of i) and ii); and wherein the weight percentages are based on the total weight of the cosmetic composition.
  • the instant disclosure relates to methods for co-stabilizing compound of thiopyridinone type (I) or (I') and hydrophilic antioxidants when both are present in the composition in amount sufficient to produce stability of compound of thiopyridinone type and hydrophilic antioxidants.
  • the cosmetic compositions are useful for treating skin, for examples, the skin of the face and neck of a human.
  • the instant disclosure relates to methods of treating the skin comprising application of the cosmetic composition of the instant disclosure to the skin.
  • the cosmetic compositions are additionally useful in methods for treating dark spots, and uneven skin texture. The aforementioned methods may be non-therapeutic.
  • compositions typically including at least one compound corresponding to the following formula (I) or (I'), referred to as “compound of thiopyridinone type”.
  • the present disclosure provides cosmetic compositions that are unique in comparison to conventional cosmetic compositions because they contain an association of two molecules, compound of thiopyridinone type (I) or (I') and hydrophilic antioxidants, that show a co-stabilization effect.
  • the inventors have discovered that combining the two molecules improves the stability of both.
  • compositions of the instant disclosure typically include: i) at least one compound selected from compounds of formula (I) and tautomer of formula (I') herein below; and their optical isomers, racemates, and/or solvates such as hydrates, alone or as a mixture :
  • R 1 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 10 or branched C 3 -C 10 alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 ii) -S-R 3 ; - R 2 denotes a radical chosen from: a) a hydrogen atom; b) a saturated hydrocarbonated group linear C 1 -C 12 or branched C 3 - C 12 or cyclic C 3 -C 8 , optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 ii) -S-R 3 iii) -C(O)-O-R 3 ; iv) a C 5 -C 12 aryl group optionally substituted with one or more hydroxyls and/or with one or more C 1 -C 8 alkoxy radicals;
  • R 3 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 10 or branched C 3 -C 10 alkyl group; ii) one or more ascorbic acid and its derivatives.
  • Applicants formulated a novel association of compound of thiopyridinone type with one or more hydrophilic antioxidants that demonstrates an unexpected co-stability of compound of thiopyridinone type and the one or more hydrophilic antioxidants.
  • the Novel association of compound of thiopyridinone type with one or more hydrophilic antioxidants also promote the antioxidizing effect.
  • compositions comprising the novel association that are appropriate for topical application to the skin include compositions in the form of a lotion, serum, gel, milk, foam, liquid foundation or cream.
  • a suitable cosmetically acceptable carrier system may be selected from any one of oil-in-water emulsions, water -in-oil emulsions, silicone in water emulsions, dispersions, micellar waters, biphasic compositions, foams, and alcohol based.
  • a "saturated hydrocarbonated group linear C 1 -C 12 or branched C 3 -C 12” is equivalent to a "linear (C 1 -C 12 )alkyl or branched (C 3 -C 12 )alkyl group” which correspond to a saturated C 1 -C 12 linear or branched C 3 -C 12 hydrocarbon based group, and preferably C 1 -C 10 linear or C 3 -C 10 branched hydrocarbon based group, more preferably C 1 -C 6 linear or C 3 -C 6 branched hydrocarbon-based;
  • the linear or branched groups may be chosen from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl.
  • the saturated linear or branched alkyl groups may be chosen from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl and octyl, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl.
  • a saturated hydrocarbonated cyclic C 3 -C 8 group is a mono or bicyclic cycloalkyl group containing from 3 to 8 carbon atoms especially is a monocyclic cycloalkyl group in C5 to C7 such as cyclohexyl group,
  • an "alkoxy radical” is an alkyl-oxy radical for which the alkyl radical is a linear or branched C 1 -C 16 and preferentially C 1 -C 8 hydrocarbon-based radical;
  • an "aryl” group represents a fused or non-fused monocyclic or bicyclic carbon- based group comprising from 5 to 12 carbon atoms, preferably from 6 to 10 carbon atoms, and in which at least one ring is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, more preferably a phenyl group ;
  • salts of the compounds of formula (I), (I ), (II) or (II’) as defined herein after comprise the conventional non-toxic salts of said compounds, such as those formed from organic or inorganic acid or from organic or inorganic base.
  • salts of the compounds of formula (I), (I'), (II) or (II’) mention may be made of : the salts obtained by addition of the compound of formula (I) or (II) to :
  • a mineral base such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonate or hydrogen carbonate for example; or an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functions; mention may be made in particular of 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1 ,3-propanediol and 3- (dimethylamino)propylamine.
  • salts of amino acids for instance lysine, arginine, guanidine, glutamic acid and aspartic acid.
  • the salts of the compounds of formula (I) or (II) may be chosen from alkali metal or alkaline-earth metal salts such as sodium, potassium, calcium or magnesium salts and ammonium salts.
  • organic or inorganic acid salt' is more particularly chosen from salts chosen from a salt derived from i) hydrochloric acid HCI, ii) hydrobromic acid HBr, iii) sulfuric acid H 2 SO 4 , iv) alkylsulfonic acids: Alk-S(O) 2 OH such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(O) 2 OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-O-S(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phen
  • the acceptable solvates of the compounds described in the instant disclosure comprise conventional solvates such as those formed during the preparation of said compounds owing to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.
  • optical isomers are in particular, the enantiomers and the diastereoisomers.
  • the compounds used according to the instant disclosure therefore correspond to formula (I) or tautomer (I') below or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture.
  • R 1 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 10 or branched C 3 -C 10 alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 ii) -S-R 3 ; R 2 denotes a radical chosen from: a) a hydrogen atom; b) a saturated hydrocarbonated group linear C 1 -C 12 or branched C 3 -C 12 or cyclic C 3 - C 8 , optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 ii) -S-R 3 iii) -C(O)-O-R 3 ; iv) a C 5 -C 12 aryl group optionally substituted with one or more hydroxyls and/or with one or more C 1 .
  • R 3 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 10 or branched C 3 -C 10 alkyl group;
  • the compound (I') is the tautomer form of the compound (I) when a tautomeric equilibrium exists according to the following scheme:
  • R 1 represents one hydrogen atom.
  • R 1 represents a linear (C 1 -C 10 )alkyl group or branched (C 3 -C 10 )alkyl group, especially a linear (C 1 -C 6 )alkyl group or branched (C 3 -C 6 )alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably ethyl.
  • the said alkyl group of R 1 is not substituted.
  • R 2 represents one hydrogen atom.
  • R 2 represents a linear (C 1 -C 10 )alkyl group or branched (C 3 -C 10 )alkyl group, especially a linear (C 1 -C 6 )alkyl group or branched (C 3 -C 6 )alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl group ; the said alkyl group of R 2 being not substituted.
  • R 2 represents a linear (C 1 -C 10 )alkyl group or branched (C 3 -C 10 )alkyl group, especially a linear (C 1 -Cs)alkyl group or branched (C 3 -C 6 )alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; the said alkyl group being substituted by one or more groups selected from i), ii), iii) and iv) as defined herein before.
  • the said alkyl group being substituted by one or two groups selected from i), ii) and iii), more preferably by one or two groups selected from i) and iii), better substituted by one group iii) as carboxy.
  • R 2 represents a (C 3 -C 8 )cycloalkyl group, preferably a (C 5 -C 7 )cycloalkyl group such cyclohexyl.
  • R 2 represents C 5 -C 12 aryl group optionally substituted with one or more hydroxyls and/or with one or more C 1 -C 8 alkoxy radicals, preferably a phenyl group particularly not substituted.
  • R 3 represents a hydrogen atom.
  • R 3 represents a saturated linear C 1 -C 10 or branched C 3 -C 10 alkyl group; particularly a linear (C 1 -C 6 )alkyl group or a branched ( C 3 -C 6 )alkyl group, preferably (C 1 -C 4 )alkyl group such as methyl group.
  • R 1 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 6 or branched C 3 -C 6 alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 ii) -S-R 3 ; preferably optionally substituted with one or more groups i)
  • R 2 denotes a radical chosen from: a) a hydrogen atom; b) a saturated hydrocarbonated group linear C 1 -C 10 or branched C 3 -C 10 or cyclic C 3 - C 8 such as C5 -06 , optionally substituted with one or more groups, which may be identical or different, chosen from: i)
  • R 1 denotes a radical chosen from: a) a hydrogen atom; b) a saturated linear C 1 -C 4 or branched C 3 -C 4 alkyl group optionally substituted with one or more groups, which may be identical or different, chosen from i) -OR 3 , more preferably not substituted;
  • R 2 denotes a radical chosen from: a) a hydrogen atom; b) a saturated hydrocarbonated group linear C 1 -C 10 or branched C 3 -C 10 or cyclic C 3 -C 8 as C5 -C6 , optionally substituted with one or more groups, which may be identical or different, chosen from: i) -O-R 3 iii) -C(O)-O-R
  • R 1 is a hydrogen atom
  • R 2 denotes a radical chosen from: a) a hydrogen atom
  • R 2 is even more preferably a saturated hydrocarbonated group linear C 1 -C 4 or branched C 3 -C 4 substituted with one group iii) -C(0)-OR 3 .
  • compounds of formula (I) and tautomer (I ' ) are selected among compounds of formula (II) and also the tautomers thereof, the salts thereof, the solvates thereof and the optical isomers thereof, and the racemates thereof, alone or as a mixture :
  • Formula (I) and (I') Wherein R1 and R3 have the same meaning than for compounds of formula (I) and (I') and X denotes an alkylene radical -(CH 2 ) n - with n being an integer ranging inclusively from 1 to 10, preferably ranging from 1 to 6, more preferably ranging from 1 to 4, such as 1 , preferably R 3 represents a hydrogen atom.
  • the following compounds are preferably used and their tautomer or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture:
  • the following compounds are more particularly preferred: More preferably, among these compounds, the following compounds are more particularly preferred:
  • composition used according to the disclosure comprises at least one compound of formulae (I) and/or (II) as described above, in a physiologically acceptable medium.
  • the compound (I), (I'), (II) and/or (II’) may be present in the composition used according to the disclosure in an amount which may be between 0.01% and 10% by weight, preferably between 0.1 % and 5% by weight, in particular from 0.5% to 3% by weight, relative to the total weight of the composition.
  • the cosmetic compositions include ascorbic acid and its derivatives.
  • composition according to the disclosure includes ascorbic acid or one of its derivatives, in a maximum content of 20% by weight relative to the total weight of composition.
  • Ascorbic acid within the meaning of the disclosure preferably corresponds to L- ascorbic acid, or vitamin C. Its structure is formula (A):
  • ascorbyl glucoside is meant the condensation product of glucose, in the form D, that is to say in the form of glucopyrannose ⁇ or ⁇ or furannosis ⁇ or ⁇ , or in the form L, with the ascorbic acid, preferably in the form L.
  • ascorbyl glucoside is le 2-O- ⁇ -D-glucopyranoside of L-ascorbic acid, in particular available from the company HAYAS HI BARA.
  • the composition according to the invention comprises vitamin C or a stabilized derivative thereof, selected from the group consisting of ascorbic acid, erythorbic acid, sodium ascorbate/erythorbate, tetrahexyl decyl ascorbate/erythorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, glucosamine ascorbate, and ascorbyl acetate.
  • vitamin C selected from the group consisting of ascorbic acid, erythorbic acid, sodium ascorbate/erythorbate, tetrahexyl decyl ascorbate/erythorbate, ascorbyl palmitate, magnesium ascorbyl phosphate, ascorbyl glucoside, glucosamine ascorbate, and ascorbyl acetate.
  • composition according to the invention comprises ascorbic acid, preferably L-ascorbic acid.
  • the composition preferably comprises from 0.1% to 20 wt. % of ascorbic acid or one of its derivatives, based to the total weight of the composition, preferably from 1 % to 15 wt.% based to the total weight of the composition.
  • the total amount of ascorbic acid and its derivatives may be present from about 0.1 , 0.5, 1 , 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5 to about 9.5, 10,
  • the component ii) may also comprise one or more additional antioxidant different from vitamin C or derivatives thereof, which may be cinnamic acid or a derivative thereof, e.g., a phenylpropanoid.
  • Phenylpropanoids include: cinnamic acid, caffeic acid, ferulic acid, trans-ferulic acid (including its antioxidant pharmacore 2,6-dihydroxy acetophenome), 5-hydroxyferic acid, sinapic acid, Coumarin, coniferyl alcohol, sinapyl alcohol, eugenol, Chavicol, baicalein, P-coumaric acid and sinapinic acid. Without limiting the mode of action of the present invention, phenylpropanoids can neutralize free radicals.
  • useful cinnamic acid derivatives may comprise 2-ethylhexyl methoxycinnamate, isopropyl methoxycinnamate, isoamyl methoxycinnamate, diisopropyl methoxycinnamate, pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate (Tinogard TT), octadecyl di-t-butyl-4-hydroxyhydrocinnamate, caffeic acid, ferulic acid. Caffeic acid and ferulic acid may be preferable, and ferulic acid may be more preferable.
  • composition according to the present invention may comprise at least one pH adjusting agent (pH adjuster). Two or more pH adjusting agents may be used in combination. Thus, a single type of pH adjusting agent or a combination of different types of pH adjusting agents may be used.
  • At least one acidifying agent and/or at least one basifying agent may be used.
  • the acidifying agent may be a monovalent or polyvalent, such as divalent, acid.
  • the acidifying agents can be, for example, mineral (inorganic) acids such as hydrochloric acid, sulfuric acid, phosphoric acid, or organic acids such as carboxylic acids, for instance tartaric acid, citric acid, and lactic acid, as well as sulphonic acids.
  • the basifying agent may be a monovalent or polyvalent, such as divalent, base.
  • the basifying agents may be mineral (inorganic) or organic, or hybrid.
  • the mineral basifying agents may be chosen from aqueous ammonia; alkali metal carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and mixtures thereof.
  • the organic basifying agents may be chosen from organic amines with a pKb at 25°C of less than 12, preferably less than 10, and even more advantageously less than 6. It should be noted that it is the pKb corresponding to the function of highest basicity.
  • the organic amines do not comprise any alkyl or alkenyl fatty chains comprising more than ten carbon atoms.
  • the organic basifying agent may be chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and amine compounds of formula (III) below: in which
  • W represents a C 1 -C 6 divalent alkylene radical optionally substituted with one or more hydroxyl groups or a C 1 -C 6 alkyl radical, and optionally interrupted with one or more heteroatoms such as O and N, and
  • R x , R y , R z , and R t which may be identical or different, represent a hydrogen atom or a C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 aminoalkyl radical.
  • amine compounds of formula (III) examples include 1 ,3- diaminopropane, 1 ,3-diamino-2-propanol, spermine and spermidine.
  • alkanolamine means an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched C 1 -C 8 alkyl groups bearing one or more hydroxyl radicals.
  • Alkanolamines such as monoalkanolamines, dialkanolamines or trialkanolamines comprising one to three identical or different C 1 -C 4 hydroxyalkyl radicals may be suitable for the present invention.
  • monoethanolamine MEA
  • diethanolamine triethanolamine
  • monoisopropanolamine diisopropanolamine
  • diisopropanolamine N-dimethylaminoethanolamine
  • 2-amino- 2-methyl- 1-propanol triisopropanolamine
  • 2-amino-2-methyl-1 ,3-propanediol 3-amino- 1 ,2-propanediol, 3-dimethylamino-1,2-propanediol and tris(hydroxymethylamino)methane.
  • Amino acids that may be used are of natural or synthetic origin, in their L, D or racemic form, and comprise at least one acid function chosen more particularly from carboxylic acid, sulfonic acid, phosphonic acid or phosphoric acid functions.
  • the amino acids may be in neutral or ionic form.
  • Such basic amino acids may preferably be chosen from those corresponding to formula (IV) below; in which
  • R represents a group chosen from:
  • the compounds corresponding to formula (IV) include histidine, lysine, arginine, ornithine and citrulline.
  • the organic basifying agent may be chosen from organic amines of heterocyclic type. Besides histidine that has already been mentioned in the amino acids, mention may in particular be made of pyridine, piperidine, imidazole, triazole, tetrazole and benzimidazole.
  • the organic basifying agent may also be chosen from amino acid dipeptides.
  • amino acid dipeptides that may be used in the present invention, mention may be made especially of carnosine, anserine and baleine.
  • the organic basifying agent may also be chosen from compounds comprising a guanidine function.
  • amines of this type that may be used in the present invention, besides arginine, which has already been mentioned as an amino acid, mention may be made especially of creatine, creatinine, 1 ,1-dimethylguanidine, 1 ,1-diethyl-guanidine, glycocyamine, metformin, agmatine, N-amidinoalanine, 3-guanidino-propionic acid, 4- guanidinobutyric acid and 2-([amino(imino)methyl]amino)ethane-1 -sulfonic acid.
  • the organic basifying agent may be selected from amino acids, preferably basic amino acids, and more preferably arginine, lysine, histidine or mixtures thereof. Even more preferentially, the organic basifying agent may be arginine.
  • Hybrid compounds that may be mentioned include the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid. Guanidine carbonate or monoethanolamine hydrochloride may be used in particular.
  • the pH adjusting agent may be present in an amount of 0.01 % by weight or more, preferably 0.05% by weight or more, and more preferably 0.1 % by weight or more, relative to the total weight of the composition.
  • the pH adjusting agent may be present in an amount of 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the pH adjusting agent may be present in an amount ranging from 0.01 % to 15% by weight, preferably from 0.05% to 10% by weight, and more preferably from 0.1% to 5% by weight or less, relative to the total weight of the composition.
  • composition according to the present invention have a pH of 4.5 or more, and more preferably 5 or more.
  • composition according to the present invention have a pH of 6.5 or less, and more preferably 6 or less.
  • composition according to the present invention have a pH of from 4.5 to 6.5, and more preferably from 5 to 6.
  • the pH of the composition means the pH of the aqueous phase of the composition according to the present invention.
  • At least one buffer or buffering agent also be used, as the pH adjusting agent, in combination with the acidifying agent and/or the basifying agent, in order to stabilize the pH of the composition according to the present invention.
  • the buffer any of commonly known buffers may be used.
  • salts of acids or bases preferably salts of weak acids or weak bases, may be used.
  • sodium citrate or sodium lactate may be used as the buffer, if citric acid or lactic acid is used as the acidifying agent.
  • composition according to the present invention may comprise at least on preservative.
  • the preservative useful according to the present invention can be any one conventionally used for cosmetics, in particular for masks.
  • the content of the preservative is 0.01 % to 5% by weight, preferably 0.01 % to 3% by weight, preferably 0.01% to 1% by weight, based on the weight of the composition.
  • composition according to the invention can advantageously comprise at least one medium/solvent, including water and/or organic medium/solvent.
  • the composition according to the invention may advantageously comprise water in various amounts.
  • a relatively high amount of water may be used.
  • water is used in a content of greater than or equal to 40% by weight relative to the total weight of composition.
  • the water content in the low viscosity composition according to the invention preferably ranges from 40% to 99% by weight, or preferably from 50% to 90% by weight, or from 60% to 80% by weight, relative to the total weight of the composition.
  • the high viscosity composition according to the invention advantageously comprises water in a content of less than or equal to 40% by weight relative to the total weight of composition.
  • the water content in the high viscosity composition according to the invention preferably ranges from 10% to 40% by weight, or preferably from 15% to 35% by weight, or from 20% to 30% by weight, relative to the total weight of the composition.
  • composition according to the invention may also comprise one or more organic medium/solvents, preferably water-soluble organic medium/solvents (solubility of greater than or equal to 5% in water at 25°C and at atmospheric pressure).
  • organic medium/solvents preferably water-soluble organic medium/solvents (solubility of greater than or equal to 5% in water at 25°C and at atmospheric pressure).
  • organic medium/solvents examples include linear or branched, and preferably saturated, monoalcohols or diols, comprising 2 to 10 carbon atoms, such as ethanol, (iso)propanol, butanol, hexylene glycol (2-methyl-2,4- pentanediol), neopentyl glycol and 3-methyl-1 ,5-pentanediol, butylene glycol, dipropylene glycol and propylene glycol; aromatic alcohols such as phenylethyl alcohol; polyols containing more than two hydroxyl functions, in particular C3 -C6 polyols, such as glycerol; polyol ethers, for instance ethylene glycol monomethyl, monoethyl and monobutyl ether, propylene glycol or ethers thereof, for instance propylene glycol monomethyl ether; and also diethylene glycol alkyl ethers, especially C1-C4 alkyl
  • the organic medium/solvents when they are present in an amount ranging from 0.1% to 40% by weight, preferably from 1% to 30% by weight, or from 5% to 20% by weight, relative to the total weight of the composition according to the invention.
  • composition according to the present invention can be used for various use, comprising application directly on keratin materials, or use to formulate other cosmetic products, such as body cream and in particular various masks.
  • active agents for improving the condition of the skin in the case of mask, such as moisturizers or agents serving to improve the natural lipid barrier. It is also possible to use enzymes that have activity on the skin.
  • active agents there are agents for drugs, peptides, proteins, detectable labels, contrast reagents, pain-killing, anesthetics, antibacterial agents, anti-yeast agents, antifungal agents, antiviral agents, anti-dermititis agents, anti-pruritic agents, anti-emetics, vascular protectors, agents against motion sickness, anti-irritants, anti-inflammatory agents, immunomodulators, anti- hyperkeratolytic agents, agents for treating dry skin, antiperspirants, anti-psoriatic agents, antidandruff agents, anti-aging agents, antiasthmatic agents and bronchodilators, sunscreen agents, antihistamines, healing agents, corticosteroids, tanning agents, and mixtures thereof.
  • the content of the other active agent in the composition according to the present invention may be adjusted as a function of the intended purpose of the kit.
  • the cosmetic compositions include a cosmetically acceptable carrier system.
  • Cosmetically acceptable means a carrier that is compatible with any keratinous substrate, and for purposes hereof, includes water and optionally water based solvents subject to any exclusions as disclosed herein.
  • the cosmetic compositions may comprise any constituent normally employed in the topical application and administration envisaged. Mention may in particular be made of water, solvents, polyols, fatty compounds (i.e. described by the International Federation Societies of Cosmetic Chemists, for example, in Cosmetic Raw Material Analysis and Quality, Volume I: Hydrocarbons, Glycerides, Waxes and Other Esters (Redwood Books, 1994), which is incorporated herein by reference in its entirety), pigments, fillers, silicones, surfactants, thickeners, gelling agents, preservatives, chelating agents, and their mixtures in all proportions.
  • the composition used according to the invention may then comprise any adjuvant commonly used in the cosmetics field.
  • the instant disclosure also relates to methods of using the cosmetic compositions described herein.
  • the cosmetic compositions can be used in a method that comprises applying the cosmetic compositions to the skin of humans. In some cases, the composition is applied to the face.
  • the cosmetic composition can be used in methods for depigmenting, lightening and/or bleaching keratin materials, preferably skin, comprising the step of: applying to the keratin substance the composition according to the compositions described herein.
  • the aforementioned methods are non-therapeutic.
  • the cosmetic composition may be applied once per day, twice per day, or more than once or twice per day. In some cases, the composition is applied in the evenings before bed. In other cases, the compositions are applied in the morning. In still other cases, the composition may be applied immediately after washing the skin.
  • the compositions may be used once, or for a series of days, weeks, or months. For example, the compositions may be used daily for a period of 1 , 2, 3, 4, 5, 6, 7, 8 or more weeks, or months.
  • the instant disclosure also relates to non-therapeutic cosmetic process for depigmenting, lightening and/or bleaching keratin materials, preferably skin, comprising the step of applying to the keratin substance the composition according to the compositions described herein.
  • the composition of the present invention may also contain adjuvants which are customary in the cosmetic, pharmaceutical and/or dermatological field depending on the final uses and/or the specific product forms, such as hydrophilic or lipophilic gelling agents, emulsifiers, hydrophilic or lipophilic active agents, fragrances, fillers, odor absorbers and dyes.
  • adjuvants which are customary in the cosmetic, pharmaceutical and/or dermatological field depending on the final uses and/or the specific product forms, such as hydrophilic or lipophilic gelling agents, emulsifiers, hydrophilic or lipophilic active agents, fragrances, fillers, odor absorbers and dyes.
  • the amounts of these various adjuvants are those conventionally used in the field under consideration, and for example from 0.01 % to 20% by weight of the total weight of the composition.
  • compositions according to the invention can be manufactured by known processes, generally used in the cosmetic or dermatological field.
  • composition according to the invention finds its application in a large number of cosmetic treatments for keratin materials such as the skin, the scalp or the mucous membranes (lips), and more particularly the skin, in particular in the care of the face, to brighten the skin.
  • keratin materials such as the skin, the scalp or the mucous membranes (lips), and more particularly the skin, in particular in the care of the face, to brighten the skin.
  • the composition according to the invention may be particularly useful for a mask product
  • the subject of the invention is also a cosmetic process for the care or makeup of keratin materials, comprising the application to the keratin materials of a composition as defined above.
  • the subject of the invention is also a non-therapeutic cosmetic process for the care or makeup of keratin materials, comprising the application to the keratin materials of a composition as defined above.
  • the invention also relates to the cosmetic use of a composition as defined above, for the care or makeup of keratin materials.
  • the subject of the invention is the cosmetic use of a composition as defined above, for the care of the skin, preferably for brightening the skin, and/or reducing or lightening darker and/or more coloured spots on the skin.
  • the composition is suitable for the treatment of darker and/or more coloured spots on the skin.
  • Compound 20 is synthesized as disclosed in example 2 of patent EP3 390 363.
  • Formula bulk was added to a 30 mL aluminum tube that was then crimped and sealed.
  • An initial, freshly made sample (TO) was submitted for Thiopyridone (THP) metering.
  • Samples were placed in temperature-controlled ovens at 25°C and 45°C for a total of 2 months. At 1 month and 2 months at each temperature, samples were removed and submitted for Thiopyridone (THP) metering.
  • the % remaining presented in Table 2 compares the 2 months, 45°C sample to the initial TO sample and is presented as % of THP remaining in sample when compared to TO. Metering is performed via high performance liquid chromatography with a UV detector. The results are presented in Table 2 below.
  • the higher stability lead to a higher overall active concentration when the consumer received and used the product. For example, if the formula contains 10% of Vit C alone and it is unstable, if there is 40% degradation of Vit C, now there will only be 6% Vit C left.
  • Vit C Compound of Thiopyridinone type
  • Vit C barely degrades, the Vit C will still be about 10% Vit C (J.e., 10% Vit C will be more efficacious than 6% Vit C).
  • Comparative Examples 1, 2, 3, 4, 5 and 6 containing only Vitamin C showed between 78% to 86% stability.
  • Comparative Example 7 containing only compound of Thiopyridinone type demonstrated that the association of Vit C and THP improve the stability of the THP when it is in combination with the Vit C than when it is alone.
  • Example 4 The inventive compositions of Ex.3-Ex.4, as well as comparative compositions of CE.8-CE.11 , are displayed in Table 3 below.

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Abstract

La présente invention concerne des compositions cosmétiques comprenant : (i) des composés de type thiopyridinone ; (ii) un ou plusieurs antioxydants hydrophiles ; et le composé de type thiopyridinone et l'antioxydant ou les antioxydants hydrophiles étant présents et stables.
PCT/US2023/025678 2022-06-21 2023-06-19 Composition cosmétique comprenant des antioxydants hydrophiles et des composés de thiopyridinone WO2023249912A1 (fr)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US17/844,939 2022-06-21
US17/844,939 US20230404884A1 (en) 2022-06-21 2022-06-21 Cosmetic composition comprising hydrophilic antioxidants and thiopyridinone compounds
CNPCT/CN2022/100256 2022-06-21
PCT/CN2022/100256 WO2023245459A1 (fr) 2022-06-21 2022-06-21 Composition antioxydante comprenant un composé thiopyridinone
FRFR2207483 2022-07-21
FR2207483A FR3136662A1 (fr) 2022-06-21 2022-07-21 Composition antioxydante comprenant un composé thiopyridinone
FR2211489 2022-11-04
FR2211489A FR3141623A1 (fr) 2022-11-04 2022-11-04 Composition cosmétique comprenant des antioxydants hydrophiles et des composés de thiopyridinone

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2545355A1 (fr) * 1983-04-25 1984-11-09 Kao Corp Inhibiteur de melanine, a base d'un derive d'acide cinnamique
DE10013167A1 (de) * 2000-03-17 2001-09-20 Volkhard Jenning Verwndung eines Schutzsystems zur Stabilisierung von Ascorbinsäure in kosmetischen und pharmazeutischen Zubereitungen
EP1430883A1 (fr) * 2002-12-18 2004-06-23 L'oreal Utilisation cosmétique de dérivés de l'acide ascorbique comme agents blanchissants de la peau ou des cheveux
WO2012080075A1 (fr) 2010-12-14 2012-06-21 L'oreal Procédé de dépigmentation de matières kératiniques au moyen de composés de thiopyridinone
WO2017102349A1 (fr) 2015-12-18 2017-06-22 L'oreal Procédé de dépigmentation de matières kératiniques au moyen de composés de thiopyridinone
KR102222697B1 (ko) * 2019-05-02 2021-03-04 (주)리즈케이 아스코르빈산 함유 화장료 조성물 및 이를 포함하는 화장품
US20210228467A1 (en) * 2018-10-18 2021-07-29 Baek Clinical Inc. High-Potency Vitamin C Topical Formulations
WO2022138471A1 (fr) * 2020-12-22 2022-06-30 L'oreal Stabilisation d'un composé thiopyridinone et réduction du jaunissement d'une composition le comprenant

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2545355A1 (fr) * 1983-04-25 1984-11-09 Kao Corp Inhibiteur de melanine, a base d'un derive d'acide cinnamique
DE10013167A1 (de) * 2000-03-17 2001-09-20 Volkhard Jenning Verwndung eines Schutzsystems zur Stabilisierung von Ascorbinsäure in kosmetischen und pharmazeutischen Zubereitungen
EP1430883A1 (fr) * 2002-12-18 2004-06-23 L'oreal Utilisation cosmétique de dérivés de l'acide ascorbique comme agents blanchissants de la peau ou des cheveux
WO2012080075A1 (fr) 2010-12-14 2012-06-21 L'oreal Procédé de dépigmentation de matières kératiniques au moyen de composés de thiopyridinone
WO2017102349A1 (fr) 2015-12-18 2017-06-22 L'oreal Procédé de dépigmentation de matières kératiniques au moyen de composés de thiopyridinone
EP3390363A1 (fr) 2015-12-18 2018-10-24 L'oreal Procédé de dépigmentation de matières kératiniques au moyen de composés de thiopyridinone
US20210228467A1 (en) * 2018-10-18 2021-07-29 Baek Clinical Inc. High-Potency Vitamin C Topical Formulations
KR102222697B1 (ko) * 2019-05-02 2021-03-04 (주)리즈케이 아스코르빈산 함유 화장료 조성물 및 이를 포함하는 화장품
WO2022138471A1 (fr) * 2020-12-22 2022-06-30 L'oreal Stabilisation d'un composé thiopyridinone et réduction du jaunissement d'une composition le comprenant

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