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WO2023245463A1 - A stabilized composition comprising a thiopyridinone compound and chelating agent - Google Patents

A stabilized composition comprising a thiopyridinone compound and chelating agent Download PDF

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Publication number
WO2023245463A1
WO2023245463A1 PCT/CN2022/100265 CN2022100265W WO2023245463A1 WO 2023245463 A1 WO2023245463 A1 WO 2023245463A1 CN 2022100265 W CN2022100265 W CN 2022100265W WO 2023245463 A1 WO2023245463 A1 WO 2023245463A1
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Prior art keywords
alkyl group
formula
branched
linear
group
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PCT/CN2022/100265
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French (fr)
Inventor
Huiqin CHEN
Xiaomin WENG
Shan Wu
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LOreal SA
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LOreal SA
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Priority to PCT/CN2022/100265 priority Critical patent/WO2023245463A1/en
Priority to FR2207326A priority patent/FR3137834B1/en
Priority to PCT/JP2023/023442 priority patent/WO2023249121A1/en
Priority to US18/875,814 priority patent/US20250381115A1/en
Priority to CN202380060558.6A priority patent/CN119730829A/en
Priority to EP23738925.9A priority patent/EP4543404A1/en
Publication of WO2023245463A1 publication Critical patent/WO2023245463A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • 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

Definitions

  • the present invention relates to a specific composition comprising a thiopyridinone compound and a chelating agent, which is useful for caring for keratin materials, and in particular the skin.
  • Brightening of the skin is always high interest of the consumers, especially those who have a dark or dull skin tone.
  • some people see the appearance on their skin, and more in particular on the hands, of darker and/or more colored spots, which give the skin heterogeneity. These spots are in particular due to a high concentration of melanin in the keratinocytes located at the surface of the skin.
  • 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.
  • thiopyridinone compound tends to be destabilized in a composition over time, in particular when the composition including the thiopyridinone compound is maintained for a relatively long period of time under elevated temperature. There is therefore a need for a composition comprising thiopyridinone with increased stability.
  • composition comprising the components of: A) a compound of formula (I) or (I’) , which can be deemed as a thiopyridinone compound, or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture; and B) a specific chelating agent solves these problems.
  • R 1 denotes a radical chosen from:
  • R 2 denotes a radical chosen from:
  • R 3 denotes a radical chosen from:
  • 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 ofR 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 ofR 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 -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; 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.
  • radical R 2 Another variant for radical R 2 is that the said alkyl group being substituted by one group iv) especially substituted by one phenyl group.
  • 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.
  • 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;
  • the 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.
  • 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;
  • 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 HCl, 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
  • the acceptable solvates of the compounds described in the present invention 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 “keratin material” is the skin.
  • skin we intend all the body skin.
  • the keratin material is the face, or the neck, especially the face.
  • a numeric range is defined with a lower and an upper limit when needed, such as one or more lower limits and one or more upper limits are given to form a range optionally along with one or more preferred ranges.
  • a given range can be defined by selecting a lower limit and an upper limit that define the boundaries of the given range. All ranges defined in this manner are inclusive and combinable, that is, any lower limit can be combined with any upper limit to form a range, as long as the lower and upper limits are provided to modify the same subject. For example, when ranges of 60-110 and 80-120 are listed for a specific subject, it is to be understood that ranges 60-120 and 80-110 are also contemplated and encompassed. Further, if the lower limits listed are 1 and 2 and the upper limits are listed as 3, 4 and 5, the following ranges are all predictable and within the scope of the present disclosure: 1-3, 1-4, 1-5, 2-3, 2-4 and 2-5.
  • the present invention provides a composition comprising the components of: A) a compound of formula (I) or (I’) , and B) a specific chelating agent.
  • composition according to the invention comprises a compound of formula (I) or (I’) below 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, as component A) :
  • R 1 denotes a radical chosen from:
  • R 2 denotes a radical chosen from:
  • R 3 denotes a radical chosen from:
  • 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 ofR 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 ofR 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 -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; 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.
  • radical R 2 Another variant for radical R 2 is that the said alkyl group being substituted by one group iv) especially substituted by one phenyl group.
  • 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.
  • the compounds of formula (I) and tautomer (I’) 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:
  • R 2 denotes a radical chosen from:
  • a phenyl group optionally substituted with one or more hydroxyls and/or with one or more C 1 -C 4 alkoxy radicals such as methoxy;
  • R 3 denotes a radical chosen from:
  • the compounds of formula (I) and tautomer (I’) or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture; have the following meanings:
  • R 1 denotes a radical chosen from:
  • R 2 denotes a radical chosen from:
  • R 3 denotes a radical chosen from:
  • the compounds of formula (I) and tautomer (I’) or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture; have the following meanings:
  • R 1 is a hydrogen atom
  • R 2 denotes a radical chosen from:
  • 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 (O) -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:
  • 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 followiing compounds are preferably used and their tautomer or their salts, their optical isomers, racemates, and/or solvattes such as hydrates and the thereof, alone or as a mixture:
  • the compound according to the present invention is the following:
  • the compound 20, N- [ (2-thioxo-1, 2-dihydropyridin-3-yl) carbonyl] glycine may also be nominated as 3-carboxymethylaminocarbonyl-2-thiopyridinone, is a typical representative of the useful thiopyridinone compounds according to the present invention.
  • the compound (I) , (I’) , (II) and/or (II’) may be present in an amount ranging for example from 0.01%to 10%by weight, preferably from 0.1%to 5%by weight, in particular from 0.5%to 3%by weight, relative to the total weight of the composition.
  • the composition may comprise a chelating agent.
  • chelating agents are defined and described in particular in the article "Chelating agents” Kirk Othmer Encyclopedia of Chemical Technology, Vol. 5 pp. 708-739, published in 2003.
  • a chelating agent is specific succinic acid derivatives, such as ethylenediamine disuccinic acid (EDDS) , and a salt thereof.
  • EDDS ethylenediamine disuccinic acid
  • These agents are particularly useful for reducing the electrostatic bonding associated with substantial presence of water in the intermediate makeup and/or care composition according to the invention.
  • the chelating agent can be present in the composition from 0.001%to 1%by weight, preferably from 0.01%to 0.5%by weight, relative to the total weight of the composition according to the present invention.
  • composition according to the present invention can comprise a surfactant, e.g., a nonionic surfactant, or a mixture thereof.
  • a surfactant e.g., a nonionic surfactant, or a mixture thereof.
  • Examples of the useful nonionic surfactants may comprise esters of polyols and of fatty acids with a saturated or unsaturated chain containing, and the oxyalkylenated derivatives thereof, i.e. derivatives containing oxyethylenated and/or oxypropylenated units, such as the glyceryl esters, and the oxyalkylenated derivatives thereof; the polyethylene glycol esters, and the oxyalkylenated derivatives thereof; the sorbitol esters, and the oxyalkylenated derivatives thereof; the sugar (sucrose, glucose or alkylglucose) esters, and the oxyalkylenated derivatives thereof; fatty alcohol ethers; the sugar ethers, and mixtures thereof.
  • esters of polyols and of fatty acids with a saturated or unsaturated chain containing i.e. derivatives containing oxyethylenated and/or oxypropylenated units, such as the
  • Glyceryl esters of fatty acids that may especially be mentioned include glyceryl stearate (glyceryl monostearate, distearate and/or tristearate) .
  • Polyethylene glycol esters of fatty acids that may especially be mentioned include polyethylene glycol 40 OE monostearate.
  • the nonionic surfactant may be present in the composition according to the present invention in an amount from 0.1%to 15%by weight, such as from 0.15%to 10%by weight, relative to the total 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, more 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, more 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; or polyols containing more than two hydroxyl functions, in particular C3-C6 polyols, such as glycerol; polyol ethers, alone or as a mixture.
  • 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 may comprise (3) at least one pH adjusting agent (pH adjuster) .
  • pH adjuster may be used in combination.
  • 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.
  • mineral (inorganic) acids such as hydrochloric acid, sulfuric acid, phosphoric acid
  • 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:
  • 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.
  • Examples of the amine compounds of formula (III) that may be mentioned 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
  • 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.
  • amino acids that may be used in the present invention, mention may be made especially of aspartic acid, glutamic acid, alanine, argiinine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.
  • amino acids are basic amino acids comprising an additional amine function optionally included in a ring or in an ureido function.
  • Such basic amino acids may preferably be chosen from those corresponding to formula (IV) below:
  • 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 (3) 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 (3) 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 (3) 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 (3) 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.
  • 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.
  • 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, preservatives, fragrances, fillers, pH adjusters, 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, preservatives, fragrances, fillers, pH adjusters, 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.
  • composition according to the invention is preferably in the form of an aqueous gel.
  • the composition comprises hydrophilic gelling agents.
  • 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 skin, to brighten the skin.
  • 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.
  • compositions according to the invention are given by way of illustration and without limitation.
  • the compounds are indicated in chemical name or INCI name.
  • compositions/formulas described below are expressed in %by weight, relative to the total weight of each composition/formula, unless otherwise indicated.
  • Compound 20 is synthesized as disclosed in example 2 of patent EP3 390 363.
  • compositions of Ex. 1-Ex. 2 were prepared, from the ingredients indicated in the table 1 below (in which the contents were indicated in%by weight of materials with regard to the total weight of the composition) :
  • compositions were prepared by the steps of, taking Ex. 1 as an example:

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Abstract

Provided is a composition comprising A) a thiopyridinone compound; and B) a chelating agent selected from succinic acid derivatives, such as ethylenediamine disuccinic acid, and a salt thereof.

Description

A STABILIZED COMPOSITION COMPRISING A THIOPYRIDINONE COMPOUND AND CHELATING AGENT TECHNICAL FIELD
The present invention relates to a specific composition comprising a thiopyridinone compound and a chelating agent, which is useful for caring for keratin materials, and in particular the skin.
BACKGROUND
Brightening of the skin is always high interest of the consumers, especially those who have a dark or dull skin tone. Unfortunately, at various periods of their life, some people see the appearance on their skin, and more in particular on the hands, of darker and/or more colored spots, which give the skin heterogeneity. These spots are in particular due to a high concentration of melanin in the keratinocytes located at the surface of the skin.
It is known that certain 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.
However, it has been discovered that a thiopyridinone compound tends to be destabilized in a composition over time, in particular when the composition including the thiopyridinone compound is maintained for a relatively long period of time under elevated temperature. There is therefore a need for a composition comprising thiopyridinone with increased stability.
SUMMARY OF THE INVENTION
The inventors have unexpectedly discovered that a composition comprising the components of: A) a compound of formula (I) or (I’) , which can be deemed as a thiopyridinone compound, or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture; and B) a specific chelating agent solves these problems.
Figure PCTCN2022100265-appb-000001
In which Formulas (I) and (I’) :
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 2denotes 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;
The compound (I’) is the tautomer form of the compound (I) when a tautomeric equilibrium exists according to the following scheme:
Figure PCTCN2022100265-appb-000002
According to one embodiment of the invention R 1 represents one hydrogen atom.
According to another embodiment of the invention 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. Particularly the said alkyl group ofR 1 is not substituted.
According to one embodiment of the invention R 2 represents one hydrogen atom.
According to another embodiment of the invention 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 ofR 2being not substituted.
According to another embodiment of the invention 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; the said alkyl group being substituted by one or more groups selected from i) , ii) , iii) and iv) as defined herein before. Preferably 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.
Another variant for radical R 2 is that the said alkyl group being substituted by one group iv) especially substituted by one phenyl group.
According to another embodiment of the invention R 2 represents a (C 3-C 8) cycloalkyl group, preferably a (C 5-C 7) cycloalkyl group such cyclohexyl.
According to another embodiment of the invention 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.
According to an embodiment R 3 represents a hydrogen atom.
According to another embodiment 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.
EMBODIMENTS OF INVENTION
Throughout the description, including the claims, the term "comprising a" should be understood as being synonymous with "comprising at least one" , unless otherwise mentioned. Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .
For the purposes of the present invention, and unless otherwise indicated:
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; Preferentially, 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.
More preferentially, 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;
■ when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined hereinabove;
■ 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;
■ the term "at least one" is equivalent to the term "one or more" ; and
■ the term "inclusive" for a range of concentrations means that the limits of that range  are included in the defined range.
The 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.
As 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.
Mention may also be made of the salts of amino acids, for instance lysine, arginine, guanidine, glutamic acid and aspartic acid. Advantageously, the salts of the compounds of formula (I) or (II) (when it comprises a carboxy group) may be chosen from alkali metal or alkaline-earth metal salts such as sodium, potassium, calcium or magnesium salts and ammonium salts.
■ as "organic or inorganic acid salt" is more particularly chosen from salts chosen from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H 2SO 4, iv) alkylsulfonic acids: Alk-S (O)  2OH such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S (O)  2OH 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 phenoxysulfinic acid; xii) phosphoric acid H 3PO 4; xiii) acetic acid CH 3C (O) OH; xiv) triflic acid CF 3SO 3H; and xv) tetrafluoroboric acid HBF 4;
■ The acceptable solvates of the compounds described in the present invention 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.
■ The optical isomers are in particular, the enantiomers and the diastereoisomers.
Preferably, the “keratin material” according to the present invention is the skin. By “skin” , we intend all the body skin. Still preferably, the keratin material is the face, or the neck, especially the face.
In the application, unless specifically mentioned otherwise, amounts, contents, parts and percentages are expressed on a weight basis.
In the application, a numeric range is defined with a lower and an upper limit when needed, such as one or more lower limits and one or more upper limits are given to form a range optionally along with one or more preferred ranges. A given range can be defined by selecting a lower limit and an upper limit that define the boundaries of the given range. All ranges defined in this manner are inclusive and combinable, that is, any lower limit can be combined with any upper limit to form a range, as long as the lower and upper limits are provided to modify the same subject. For example, when ranges of 60-110 and 80-120 are listed for a specific subject, it is to be understood that ranges 60-120 and 80-110 are also contemplated and encompassed. Further, if the lower limits listed are 1 and 2 and the upper limits are listed as 3, 4 and 5, the following ranges are all predictable and within the scope of the present disclosure: 1-3, 1-4, 1-5, 2-3, 2-4 and 2-5.
Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of components and/or reaction conditions are to be understood as being modified in all instances by the term "about" , with conventionally known meaning in the art, e.g., within 10%of the indicated number (such as "about 10%" means 9%-11 %and "about 2%" means 1.8%-2.2%) .
The present invention provides a composition comprising the components of: A) a compound of formula (I) or (I’) , and B) a specific chelating agent.
Component A)
The composition according to the invention comprises a compound of formula (I) or (I’) below 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, as component A) :
Figure PCTCN2022100265-appb-000003
In which Formulas (I) and (I’) :
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;
The compound (I’) is the tautomer form of the compound (I) when a tautomeric equilibrium exists according to the following scheme:
Figure PCTCN2022100265-appb-000004
According to one embodiment of the invention R 1 represents one hydrogen atom.
According to another embodiment of the invention 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. Particularly the said alkyl group ofR 1 is not substituted.
According to one embodiment of the invention R 2 represents one hydrogen atom.
According to another embodiment of the invention 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 ofR 2being not substituted.
According to another embodiment of the invention 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; the said alkyl group being substituted by one or more groups selected from i) , ii) , iii) and iv) as defined herein before. Preferably 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.
Another variant for radical R 2 is that the said alkyl group being substituted by one group iv) especially substituted by one phenyl group.
According to another embodiment of the invention R 2 represents a (C 3-C 8) cycloalkyl group, preferably a (C 5-C 7) cycloalkyl group such cyclohexyl.
According to another embodiment of the invention 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.
According to an embodiment R 3 represents a hydrogen atom.
According to another embodiment 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.
Preferably, the compounds of formula (I) and tautomer (I’) or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture;
have the following meanings:
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 2denotes 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-C6, optionally substituted with one or more groups, which may be identical or different, chosen from:
i) -O-R 3
ii) -SR- 3
iii) -C (O) -O-R 3;
iv) a phenyl group optionally substituted with one or more hydroxyls and/or with one or more C 1-C 4 alkoxy radicals such as methoxy;
preferably substituted with one or more groups selected from i) and iii) , preferably iii) such as carboxy
R 3 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
Preferentially, the compounds of formula (I) and tautomer (I’) or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture; have the following meanings:
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 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 4 alkoxy radicals;
R 3 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 such as methyl or ethyl.
Preferentially, the compounds of formula (I) and tautomer (I’) or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture; have the following meanings:
R 1 is a hydrogen atom; and
R 2 denotes a radical chosen from:
a) a hydrogen atom;
b) a saturated hydrocarbonated group linear C 1-C 5 or branched C 3-C 5 or cyclic C 3-C 8 as C5-C6, substituted with one or more groups, which may be identical or different, chosen from v) -C (O) -O-R 3, preferably substituted with one group iii) -C (O) -O-R 3;
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 (O) -OR 3.
According to another preferred embodiment, 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:
Figure PCTCN2022100265-appb-000005
Formula (II) and (II’) 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.
Among the compounds of formula (I) , the followiing compounds are preferably used and their tautomer or their salts, their optical isomers, racemates, and/or solvattes such as hydrates and the thereof, alone or as a mixture:
Figure PCTCN2022100265-appb-000006
Figure PCTCN2022100265-appb-000007
Figure PCTCN2022100265-appb-000008
Figure PCTCN2022100265-appb-000009
Among these compounds, the following compounds are more particularly preferred:
Figure PCTCN2022100265-appb-000010
Figure PCTCN2022100265-appb-000011
Figure PCTCN2022100265-appb-000012
Figure PCTCN2022100265-appb-000013
More preferably, among these compounds, the following compounds are more particularly preferred:
Figure PCTCN2022100265-appb-000014
Figure PCTCN2022100265-appb-000015
Even more preferably, among these compounds, the following compounds are more particularly preferred:
Figure PCTCN2022100265-appb-000016
Figure PCTCN2022100265-appb-000017
In a most preferred embodiment, the compound according to the present invention is the following:
Figure PCTCN2022100265-appb-000018
All compounds can be obtained by chemical method known by man skilled in the art, from commercially available reagents. For example, the synthetic method disclosed in the European patent application EP3 390 363 can be used.
The compound 20, N- [ (2-thioxo-1, 2-dihydropyridin-3-yl) carbonyl] glycine, may also be nominated as 3-carboxymethylaminocarbonyl-2-thiopyridinone, is a typical representative of the useful thiopyridinone compounds according to the present invention.
The compound (I) , (I’) , (II) and/or (II’) may be present in an amount ranging for example from 0.01%to 10%by weight, preferably from 0.1%to 5%by weight, in particular from 0.5%to 3%by weight, relative to the total weight of the composition.
Component B) , chelating agents
According to an embodiment of the present invention, the composition may comprise a chelating agent. Such chelating agents are defined and described in particular in the article "Chelating agents" Kirk Othmer Encyclopedia of Chemical Technology, Vol.  5 pp. 708-739, published in 2003.
The examples of a chelating agent is specific succinic acid derivatives, such as ethylenediamine disuccinic acid (EDDS) , and a salt thereof.
These agents are particularly useful for reducing the electrostatic bonding associated with substantial presence of water in the intermediate makeup and/or care composition according to the invention.
According to the present invention, the chelating agent can be present in the composition from 0.001%to 1%by weight, preferably from 0.01%to 0.5%by weight, relative to the total weight of the composition according to the present invention.
Surfactant
The composition according to the present invention can comprise a surfactant, e.g., a nonionic surfactant, or a mixture thereof.
Examples of the useful nonionic surfactants may comprise esters of polyols and of fatty acids with a saturated or unsaturated chain containing, and the oxyalkylenated derivatives thereof, i.e. derivatives containing oxyethylenated and/or oxypropylenated units, such as the glyceryl esters, and the oxyalkylenated derivatives thereof; the polyethylene glycol esters, and the oxyalkylenated derivatives thereof; the sorbitol esters, and the oxyalkylenated derivatives thereof; the sugar (sucrose, glucose or alkylglucose) esters, and the oxyalkylenated derivatives thereof; fatty alcohol ethers; the sugar ethers, and mixtures thereof.
Glyceryl esters of fatty acids that may especially be mentioned include glyceryl stearate (glyceryl monostearate, distearate and/or tristearate) .
Polyethylene glycol esters of fatty acids that may especially be mentioned include polyethylene glycol 40 OE monostearate.
Mixtures of these surfactants may also be used.
The nonionic surfactant may be present in the composition according to the present invention in an amount from 0.1%to 15%by weight, such as from 0.15%to 10%by weight, relative to the total weight of the composition.
Medium/solvent
The composition according to the invention can advantageously comprise at least  one medium/solvent, including water and/or organic medium/solvent.
Water
The composition according to the invention may advantageously comprise water in various amounts. For low viscosity applications of the composition, e.g., in form of leave-on lotion, a relatively high amount of water may be used. For example, 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, more preferably from 50%to 90%by weight, or from 60%to 80%by weight, relative to the total weight of the composition.
For high viscosity applications of the composition, e.g., in form of leave-on cream, a relatively lower amount of water may be used. 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, more preferably from 15%to 35%by weight, or from 20%to 30%by weight, relative to the total weight of the composition.
Organic medium/solvent
The 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℃ and at atmospheric pressure) .
Examples of the organic medium/solvents that may be mentioned include linear or branched, and preferably saturated, monoalcohols or diols; or polyols containing more than two hydroxyl functions, in particular C3-C6 polyols, such as glycerol; polyol ethers, alone or as a mixture.
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.
pH Adjusting Agent
The composition according to the present invention may comprise (3) 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.
As the (3) pH adjusting agent, at least one acidifying agent and/or at least one basifying agent (alkaline 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℃ 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. In addition, 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:
Figure PCTCN2022100265-appb-000019
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.
Examples of the amine compounds of formula (III) that may be mentioned include  1,3-diaminopropane, 1, 3-diamino-2-propanol, spermine and spermidine.
The term “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. Among the compounds of this type, mention may be made of monoethanolamine (MEA) , diethanolamine, triethanolamine, monoisopropanolamine, 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.
As amino acids that may be used in the present invention, mention may be made especially of aspartic acid, glutamic acid, alanine, argiinine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.
It may be preferable that the amino acids are basic amino acids comprising an additional amine function optionally included in a ring or in an ureido function.
Such basic amino acids may preferably be chosen from those corresponding to formula (IV) below:
Figure PCTCN2022100265-appb-000020
in which
R represents a group chosen from:
Figure PCTCN2022100265-appb-000021
- (CH 2)  3-NH 2,
- (CH 2)  2-NH 2,
- (CH 2)  2-NH-CO-NH 2, and
Figure PCTCN2022100265-appb-000022
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. As 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. As 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.
In a preferred embodiment of the present invention, 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 (3) 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 (3) 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 (3) 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.
It is preferable that the composition according to the present invention have a pH of 4.5 or more, and more preferably 5 or more.
It is preferable that the composition according to the present invention have a pH of 6.5 or less, and more preferably 6 or less.
It is preferable that the 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.
It may be preferable that at least one buffer or buffering agent also be used, as the (3) 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.
As the buffer, any of commonly known buffers may be used. For example, salts of acids or bases, preferably salts of weak acids or weak bases, may be used. For example, sodium citrate or sodium lactate may be used as the buffer, if citric acid or lactic acid is used as the acidifying agent.
Adjuvants
In a known manner, 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, preservatives, fragrances, fillers, pH adjusters, 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.
These adjuvants and their concentrations must be such that they do not modify the desired property for the composition of the invention.
The composition according to the invention is preferably in the form of an aqueous gel.
In a preferred embodiment according to the invention, the composition comprises hydrophilic gelling agents.
The compositions according to the invention can be manufactured by known processes, generally used in the cosmetic or dermatological field.
The 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 skin, to brighten the skin.
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.
More particularly, 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.
In a particular embodiment, the composition is suitable for the treatment of darker and/or more coloured spots on the skin.
EXAMPLES
The following examples of compositions according to the invention are given by way of illustration and without limitation. The compounds are indicated in chemical name or INCI name.
The ingredient amounts/concentrations in the compositions/formulas described below are expressed in %by weight, relative to the total weight of each composition/formula, unless otherwise indicated.
Figure PCTCN2022100265-appb-000023
Figure PCTCN2022100265-appb-000024
Compound 20 is synthesized as disclosed in example 2 of patent EP3 390 363.
Example A
The inventive compositions of Ex. 1-Ex. 2, as well as comparative compositions of CE. 1 and CE. 2, were prepared, from the ingredients indicated in the table 1 below (in which the contents were indicated in%by weight of materials with regard to the total weight of the composition) :
Table 1
Figure PCTCN2022100265-appb-000025
Figure PCTCN2022100265-appb-000026
The compositions were prepared by the steps of, taking Ex. 1 as an example:
1) . Heating the surfactant, fatty compounds, and, if used to 75℃, mixing well till all solid melted.
2) . Mixing water, glycol, chelator, and heating to 75℃, mixing well till no lumps.
3) . Transferring oil phase into water phase at 75℃, mixing homogenously for 15mins.
4) . Cooling to 30℃.
5) . Finally adding Compound 20 and Sodium Hydroxide to adjust pH to be 5.7±0.3.
Example B
The inventive compositions of Ex. 1 and CE. 1 prepared in Example A were evaluated for the degradation of Compound 20, by the steps of:
- Exactly weighing 100mg of the inventive and comparative compositions respectively into 10 mL volumetric flasks;
- Adding 2.5 mL of Ultra-pure water into it and tightening the cover, and then shaking it on vortex to make it well dispersed, no obvious agglomeration;
- Filling the methanol up to the line of the volumetric flask, and closing the lid tightly;
- Sonicating the solution 5 minutes and then cooling down to the room temperature;
- Stirring the solution on the magnetic stirring plate 1.5 hours; and
- Filtering the solution with 0.45μGHP filter to get the injection solution; and subsequently:
- First, doing UPLC (Ultra-performance liquid chromatography) analysis on the test compositions to get T0 Compound 20 degradation data; every composition having two parallel samples to be analyzed; where T0 means the time of starting the degradation test;
- Then putting the compositions into 55℃ oven for accelerating aging Test for 2 weeks and 45℃ oven for accelerating aging Test for 1 month or putting the compositions into 45℃ oven for accelerating aging Test for 2 months;
- Finally, doing analysis on the aged compositions; every composition having two parallel samples to be analyzed.
The results were given in Table 2 below.
Table 2
Figure PCTCN2022100265-appb-000027

Claims (12)

  1. A composition comprising the components of:
    A) at least one compound selected from compounds of formula (I) and tautomer of formula (I’) herein below; and their salts, optical isomers, racemates, and/or solvates such as hydrates, alone or as a mixture:
    Figure PCTCN2022100265-appb-100001
    In which Formulas (I) and (I’) :
    - R 1 denotes a radical chosen from:
    a) a hydrogen atom;
    b) a saturated linear C 1-C 10 orbranched 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;
    B) a chelating agent selected from succinic acid derivatives, such as ethylenediamine disuccinic acid, and a salt thereof.
  2. The composition according to claim 1, wherein:
    - R 1 of formula (I) and (I’) represents a hydrogen atom,
    or
    - R 1 of formula (I) and (I’) 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, particularly the said alkyl group of R 1 is not substituted.
  3. The composition according to any one of the preceding claims, wherein:
    - R 2 of formula (I) and (I’) represents a hydrogen atom;
    or
    - R 2 of formula (I) and (I’) 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.
  4. The composition according to claim 1 or 2, wherein:
    - R 2 of formula (I) and (I’) 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; the said alkyl group being substituted by one or more groups selected from i) , ii) , iii) and iv) as defined in claim 1, preferably 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.
  5. The composition according to claim 1 or 2, wherein
    - R 2 of formula (I) and (I’) represents a (C 3-C 8) cycloalkyl group, preferably a (C 5-C 7) cycloalkyl group such cyclohexyl;
    or
    - R 2 of formula (I) and (I’) represents 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, preferably a phenyl group particularly not substituted.
  6. The composition according to any one of the preceding claims, wherein
    - R 3 of formula (I) and (I’) represents a hydrogen atom;
    or
    - R 3 of formula (I) and (I’) represents a saturated linear C 1-C 10 orbranched 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.
  7. The composition according to any one of the preceding claims, wherein:
    - R 1 of formula (I) and (I’) represents 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 of formula (I) and (I’) represents a radical chosen from:
    - a) a hydrogen atom;
    - b) a saturated hydrocarbonated group linear C 1-C 10 orbranched C 3-C 10 or cyclic C 3-C 8 such as C5-C6, optionally substituted with one or more groups, which may be identical or different, chosen from:
    - i) -O-R 3
    - ii) -SR- 3
    - iii) -C (O) -O-R 3;
    - iv) a phenyl group optionally substituted with one or more hydroxyls and/or with one or more C 1-C 4 alkoxy radicals such as methoxy;
    - preferably substituted with one or more groups selected from i) and iii) , preferably iii) such as carboxy
    - R 3 of formula (I) and (I’) represents a radical chosen from:
    - a) a hydrogen atom;
    - b) a saturated linear C 1-C 6 or branched C 3-C 6 alkyl group;
    - preferentially, the compounds of formula (I) and tautomer (I’) or their salts, their optical isomers, racemates, and/or solvates such as hydrates and the thereof, alone or as a mixture;
    - have the following meanings:
    - R 1 of formula (I) and (I’) represents 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 of formula (I) and (I’) represents 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 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 4 alkoxy radicals;
    - R 3 of formula (I) and (I’) represents a radical chosen from:
    - a) a hydrogen atom;
    - b) a saturated linear C 1-C 4 or branched C 3-C 4 alkyl group such as methyl or ethyl.
  8. The composition according to any one of the preceding claims, wherein
    the compound of formula (I) selected out from the group consisting of the compounds 1 to 24 below and their tautomer or their salts, their optical isomers, racemates, and/or solvates such as hydrates, alone or as a mixture, particularly compounds 1, 2, 4, 6, 7, 9, 11, 12, 14, 15, 
    16, 17, 18, 19, 20, or 21, more particularly 1, 9, 16, 18, 19, 20, or 21, preferably 18, 19, 20, or 10 21, more preferably 20:
    Figure PCTCN2022100265-appb-100002
    Figure PCTCN2022100265-appb-100003
    Figure PCTCN2022100265-appb-100004
    Figure PCTCN2022100265-appb-100005
  9. The composition according to any one of the preceding claims, wherein the compound of formula (I) or (I’) is present in an amount ranging from 0.01%to 10%by weight, preferably from 0.5%to 3%by weight, relative to the total weight of the composition.
  10. The composition according to anyone of the preceding claims, wherein the at least one water soluble chelating agent of the polyvalent metal ion is present in the second composition from 0.001%to 1%by weight, preferably from 0.01%to 0.5%by weight, relative to the total weight of the composition.
  11. Use of a chelating agent selected from succinic acid derivatives, such as ethylenediamine disuccinic acid (EDDS) , and a salt thereof,
    for stabilizing the compound of formula (I) and tautomer of formula (I’) as defined in any one of claims 1 to 8, e.g., for stabilizing the compound 20.
  12. A 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 any one of claims 1 to 10.
PCT/CN2022/100265 2022-06-21 2022-06-21 A stabilized composition comprising a thiopyridinone compound and chelating agent Ceased WO2023245463A1 (en)

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PCT/JP2023/023442 WO2023249121A1 (en) 2022-06-21 2023-06-16 Stabilization of thiopyridinone compound and composition comprising same
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