COSMETIC COMPOSITION INCLUDING HYDROPHILIC ANTIOXIDANTS AND THIOPYRIDINONE COMPOUNDS
Combining Thiopyridinone-type compounds with hydrophilic antioxidants stabilizes both, addressing the formulation challenges of Vitamin C in cosmetic compositions for effective skin treatment.
Patent Information
- Application Number
- FR2022011489
- Authority / Receiving Office
- FR · FR
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2022-11-04
- Publication Date
- 2026-01-02
- Estimated Expiration
- 2042-11-04
AI Technical Summary
Vitamin C, a potent antioxidant, is unstable and difficult to formulate and deliver effectively to the skin, posing challenges in cosmetic compositions for treating photoaging and hyperpigmentation.
A combination of Thiopyridinone-type compounds and hydrophilic antioxidants is used to enhance the stability of both components, forming a co-stabilizing effect in cosmetic compositions.
The combination improves the stability of Thiopyridinone-type compounds and hydrophilic antioxidants, enabling effective delivery and treatment of skin issues such as brown spots and uneven skin texture.
Abstract
Description
Title of the invention: COSMETIC COMPOSITION COMPRISING HYDROPHILIC ANTIOXIDANTS AND THIOPYRIDINONE COMPOUNDS FIELD OF INVENTION
[0001] This disclosure relates to cosmetic compositions comprising a combination of ascorbic acid and its derivatives with Thiopyridinone type compounds. CONTEXT OF THE INVENTION
[0002] Vitamin C is a potent antioxidant that can be used topically in dermatology to treat and prevent changes associated with photoaging, hyperpigmentation, etc. Vitamin C is very unstable and difficult to formulate and deliver to the dermis. Research is underway to develop stable compositions that deliver large amounts of ascorbic acid to the skin. DISCLOSURE SUMMARY
[0003] The present disclosure relates to cosmetic compositions which are unique compared to conventional cosmetic compositions because they contain an association of two molecules, Thiopyridinone (I) or (I1) type compounds and hydrophilic antioxidants, which exhibit a co-stabilizing effect.
[0004] The inventors discovered that the combination of Thiopyridinone-type compounds and hydrophilic antioxidants improves the stability of both.
[0005] Cosmetic compositions generally include:
[0006] i) at least one compound selected from the compounds of formula (I) and a tautomer of formula (T) below; and their optical, racemate, and / or solvated isomers such as hydrates, alone or in mixtures:
[0007] Formulas (I) and (I') in which:
[0008] -Ri denotes a radical chosen from:
[0009] a) a hydrogen atom;
[0010] b) a linear saturated alkyl group in C1-C10 or in C3-C10-ramified form optionally substituted by one or more groups, which may be identical or different, selected from:
[0011] i)-O-R3
[0012] ii)-S-R3;
[0013] - R 2 denotes a radical chosen from:
[0014] a) a hydrogen atom;
[0015] b) a hydrocarbon group saturated with linear CrCi2 or branched C3-Ci2 or cyclic C3-C8, optionally substituted by one or more groups, which may be identical or different, selected from:
[0016] i) -O-R3
[0017] ii) -S-R3
[0018] iii) -C(O)-O-R3 ;
[0019] iv) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in Ci-C8;
[0020] c) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more CrC8 alkoxy radicals
[0021] -R3 designates a radical chosen from:
[0022] a) a hydrogen atom;
[0023] b) a linear saturated alkyl group in Ci-Cio or branched in C3-CiO;
[0024] ii) one or more hydrophilic antioxidants.
[0025] The inventors have discovered in an astonishing and unexpected way that when thiopyridinone-type compounds and one or more hydrophilic ascorbic antioxidants are present in the composition in sufficient quantities, the association has produced a costability of the thiopyridinone-type compounds and the one or more hydrophilic antioxidants.
[0026] In some embodiments, one or more hydrophilic antioxidants are generally present in the cosmetic composition in an amount of approximately 0.1 to approximately 20% by weight, relative to the total weight of the cosmetic composition. In some cases, the amount of hydrophilic antioxidants is greater than 5% by weight, for example, from approximately 6% to approximately 15% by weight, from approximately 8% to approximately 15% by weight, from approximately 9% to approximately 15% by weight, or from approximately 10% to approximately 15% by weight, relative to the total weight of the composition. In one embodiment, one or more hydrophilic antioxidants are present from approximately 1% to approximately 15% by weight, relative to the total weight of the cosmetic composition. In one embodiment, one or more Hydrophilic antioxidants are preferably chosen from ascorbic acid and its derivatives.
[0027] In some embodiments, compound i) is generally present in cosmetic compositions in an amount of approximately 0.01 to approximately 10% by weight, relative to the total weight of the cosmetic composition. In some cases, compound i) is present in an amount of approximately 0.1 to approximately 5% by weight, relative to the total weight of the cosmetic composition. In some embodiments, compound i) is generally present in cosmetic compositions in an amount of approximately 0.5 to approximately 3% by weight, relative to the total weight of the cosmetic composition.
[0028] In some embodiments, cosmetic compositions may include one or more fatty compounds.
[0029] In one or more embodiments, the cosmetic compositions may include one or more polymers.
[0030] In some embodiments, cosmetic compositions may include one or more emulsifiers.
[0031] In one or more embodiments, the cosmetic composition may have a pH between about 4.5 and about 6.5, preferably from about 5 to about 6.
[0032] In some embodiments, the cosmetically acceptable vector 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 vectors.
[0033] In some embodiments, cosmetic compositions may include:
[0034] i) from about 0.01% to about 10% by weight of at least one compound selected from the compounds of formula (I) and the tautomer of formula (!') below; and their optical, racemate, and / or solvated isomers such as hydrates, alone or in mixtures: OO M 01 (I'
[0035] Formulas (I) and (I') in which:
[0036] -Ri designates a radical chosen from:
[0037] a) a hydrogen atom;
[0038] b) a linear saturated alkyl group in C1-C10 or in C3-C10-ramified optionally substituted by one or more groups, which may be identical or different, chosen from:
[0039] i) -O-R3
[0040] ii)-S-R3;
[0041] - R 2 designates a radical chosen from:
[0042] a) a hydrogen atom;
[0043] b) a hydrocarbon group saturated with linear CrCi2 or branched C3-Ci2 or cyclic C3-C8, optionally substituted by one or more groups, which may be identical or different, selected from:
[0044] i) -O-R3
[0045] ii) -S-R3
[0046] iii) -C(O)-O-R3 ;
[0047] iv) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in Ci-C8;
[0048] c) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more CrC8 alkoxy radicals
[0049] -R3 designates a radical chosen from:
[0050] a) a hydrogen atom;
[0051] b) a linear saturated alkyl group in Ci-Cio or branched in C3-CiO;
[0052] i) from about 0.1 to about 20% by weight of one or more ascorbic acids and its derivatives; and
[0053] ii) a suitable cosmetic vector;
[0054] wherein i) a thiopyridinone-type compound and ii) one or more ascorbic acids and its derivatives are present in the composition in sufficient quantities to produce stability of i) and ii); and
[0055] in which the percentages by weight are based on the total weight of the cosmetic composition.
[0056] This disclosure relates to methods for co-stabilizing thiopyridinone (I) or (I1) type compounds and hydrophilic antioxidants when both are present in the composition in sufficient quantities to produce stability of the thiopyridinone type compound and the hydrophilic antioxidants. Cosmetic compositions are useful for treating skin, for example, the skin of a human face and neck. Thus, this disclosure relates to methods for treating skin, including the application of the cosmetic composition of this disclosure to the skin. Cosmetic compositions are also useful in processes
[0057]
[0058]
[0059]
[0060]
[0061]
[0062]
[0063] for treating brown spots and uneven skin texture. The aforementioned procedures may be non-therapeutic. These and other aspects of the invention are described in more detail in the detailed description of the invention. This disclosure describes exemplary embodiments according to general inventive concepts and is not intended to limit the scope of the invention in any way. Indeed, the invention as described in the specification is broader than, and not limited by, the exemplary embodiments presented herein, and the terms used herein have their full ordinary meaning. DETAILED DESCRIPTION OF THE DISCLOSURE This disclosure relates to cosmetic compositions typically comprising at least one compound corresponding to the following formula (I) or (!'), referred to as "thiopyridinone type compound". This disclosure proposes unique cosmetic compositions compared to conventional cosmetic compositions because they contain an association of two molecules, a thiopyridinone (I) or (P) type compound and hydrophilic antioxidants which exhibit a co-stabilizing effect. The inventors discovered that combining the two molecules improves the stability of both. The cosmetic compositions in this disclosure typically include: (i) at least one compound selected from the compounds of formula (I) and the tautomer of formula (!') below; and their optical, racemate, and / or solvated isomers such as hydrates, alone or in mixtures:
[0064]
[0065]
[0066]
[0067]
[0068] Formulas (I) and (I') in which: -Ri designates a radical chosen from: a) a hydrogen atom; b) a linear saturated alkyl group in Ci-CiO or in C3-Cioramified optionally substituted by one or more groups, which may be identical or different, chosen from: i) -O-R3
[0069] ii)-S-R3;
[0070] - R 2 designates a radical chosen from:
[0071] a) a hydrogen atom;
[0072] b) a hydrocarbon group saturated with linear CrCi2 or branched C3-Ci2 or cyclic C3-C8, optionally substituted by one or more groups, which may be identical or different, selected from:
[0073] i) -O-R3
[0074] ii) -S-R3
[0075] iii) -C(O)-O-R3 ;
[0076] iv) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in CrC8;
[0077] c) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more CrC8 alkoxy radicals
[0078] -R3 designates a radical chosen from:
[0079] a) a hydrogen atom;
[0080] b) a linear saturated alkyl group in Ci-Cio or branched in C3-CiO;
[0081] ii) one or more ascorbic acids and its derivatives.
[0082] The applicants have formulated a new association of a thiopyridinone-type compound with one or more hydrophilic antioxidants which demonstrates an unexpected costability of the thiopyridinone-type compound and the one or more hydrophilic antioxidants.
[0083] Cosmetic formulations comprising the new combination which are suitable for local application to the skin include compositions in the form of lotion, serum, gel, milk, mousse, liquid foundation or cream.
[0084] A cosmetically acceptable carrier system suitable according to the disclosure may be selected from any of the following: oil-in-water emulsions, water-in-oil emulsions, silicone-in-water emulsions, dispersions, micellar waters, biphasic compositions, foams and alcohol-based. Thiopyridinone-type compounds
[0085] For the purposes of this disclosure, and unless otherwise indicated: • A “linear CrCi2 or branched C3-Ci2 saturated hydrocarbon group” is equivalent to a “linear or branched (C3-Ci2) alkyl group” which corresponds to a linear C1-C12 saturated hydrocarbon group or a C3-Ci2 branched hydrocarbon group, and preferably a linear Ci-Ci0 or branched C3-Ci0 hydrocarbon group, more preferably a linear Ci-C6 or branched C3-C6 hydrocarbon group; preferably, the linear or branched groups may be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl.
[0086] More preferably, the linear or branched saturated alkyl groups can be chosen from the methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, pentyl, hexyl, heptyl and octyl groups, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl. • a saturated C3-C8 hydrocarbon cyclic group is a mono- or bicyclic cycloalkyl group containing 3 to 8 carbon atoms, in particular a monocyclic C5-C7 cycloalkyl group such as the cyclohexyl group, • an "alkoxy radical" is an alkyl-oxy radical for which the alkyl radical is a linear or branched hydrocarbon radical in Ci-Ci6 and preferably in CrC8; • when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above; • an “aryl” group represents a carbon-based group, monocyclic or bicyclic, fused or not, comprising from 5 to 12 carbon atoms, preferably from 6 to 10 carbon atoms, and in which at least one ring is aromatic; preferably, the aryl radical is a phenyl, biphenyl, naphthyl group, 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 are included in the defined range.
[0087] The salts of compounds of formula (I), (I'), (II) or (II1) as defined below include conventional non-toxic salts of said compounds, such as those formed from an organic or inorganic acid or an organic or inorganic base.
[0088] Examples of salts of compounds of formula (I), (I'), (II) or (II') include:
[0089] the salts obtained by adding 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;
[0090] 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 therefore include, for example, one or more alcohol groups; examples include 2-amino-2-methylpropanol and ethanolamine. triethanolamine, 2-dimethylaminopropanol, 2-amino-2-(hydroxymethyl)-1,3-propanediol, 3-(dimethylamino)propylamine.
[0091] Other examples include amino acid salts, for instance lysine, arginine, guanidine, glutamic acid, and aspartic acid. Advantageously, the salts of compounds of formula (I) or (II) (when they include a carboxy group) can be selected from alkali or alkaline earth metal salts such as sodium, potassium, calcium, or magnesium salts and ammonium salts. • A "salt of an organic or inorganic acid" is more particularly chosen from among the salts chosen from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, 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-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid H3PO4; xiii) acetic acid CH3C(O)OH; xiv) triflic acid CF3SO3H; and xv) tetrafluoroboric acid HBF4; • Acceptable solvates of the compounds described in this disclosure include conventional solvates such as those formed during the preparation of said compounds due to the presence of solvents. Examples include solvates due to the presence of water or linear or branched alcohols, such as ethanol or isopropanol. • Optical isomers include, in particular, enantiomers and diastereomers.
[0092] The compounds used according to this disclosure therefore correspond to the formula (I) or the tautomer (I') below or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture.
[0093] Formulas (I) and (F) in which:
[0094] Ri designates a radical chosen from:
[0095] a) a hydrogen atom;
[0096] b) a linear saturated alkyl group in C1-C10 or C3-C10-ramified form optionally substituted by one or more groups, which may be identical or different, selected from:
[0097] i) -O-R3
[0098] ii)-S-R3;
[0099] R2 denotes a radical chosen from:
[0100] a) a hydrogen atom;
[0101] b) a hydrocarbon group saturated with linear C-Ci2 or branched C3-Ci2 or cyclic C3-C8, optionally substituted by one or more groups, which may be identical or different, selected from:
[0102] i) -O-R3
[0103] ii) -S-R3
[0104] iii) -C(O)-O-R3 ;
[0105] iv) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in CrC8;
[0106] c) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyl groups and / or by one or more CrC8 alkoxy radicals
[0107] R3 designates a radical chosen from:
[0108] a) a hydrogen atom;
[0109] b) a linear saturated alkyl group in Ci-Cio or branched in C3-CiO;
[0110] Compound (I1) is the tautomeric form of compound (I) when a tautomeric equilibrium exists according to the following scheme:
[0111] According to one embodiment of the disclosure, Ri represents a hydrogen atom.
[0112] According to another embodiment of the disclosure, Ri represents a linear (Ci-CiO) or branched (C3-CiO) alkyl group, in particular a linear or branched (Ci-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferentially ethyl. In particular, said alkyl group of Rin' is not substituted.
[0113] According to one embodiment of the disclosure, R2 represents a hydrogen atom.
[0114] According to another embodiment of the disclosure, R2 represents a linear (Ci-Cio) or branched (C3-C10) alkyl group, in particular a linear or branched (Ci-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group of R2 not being substituted.
[0115] According to another embodiment of the disclosure, R2 represents a linear (C1-C10) or branched (C3-C10) alkyl group, in particular a linear or branched (C1-C6) alkyl group, such as methyl, ethyl, n-pentyl, n-nonyl, isobutyl, more preferably methyl or ethyl; said alkyl group being substituted by one or more groups selected from i), ii), iii) and iv) as defined herein above. Preferably, said alkyl group is substituted by one or more groups selected from i), ii) and iii), more preferably by one or more groups selected from i) and iii), preferably substituted by a group iii) as a carboxy.
[0116] Another variant for the radical R2 is that said alkyl group is substituted by a group iv) in particular substituted by a phenyl group.
[0117] According to another embodiment of the disclosure, R2 represents a cycloalkyl group (in C3-C8), preferably a cycloalkyl group (in C5-C7) such as cyclohexyl.
[0118] According to another embodiment of the disclosure, R2 represents a C5-Ci2 aryl group optionally substituted by one or more hydroxyls and / or by one or more CrC8 alkoxy radicals, preferably a phenyl group in particular unsubstituted.
[0119] According to one embodiment, R3 represents a hydrogen atom.
[0120] According to another embodiment, R3 represents a saturated linear C1-C10 or branched C3-C10 alkyl group; in particular a linear (Ci-C6) alkyl group or a branched (C3-C6) alkyl group, preferably a (C1-C4) alkyl group such as the methyl group.
[0121] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture;
[0122] have the following meanings:
[0123] Ri designates a radical chosen from:
[0124] a) a hydrogen atom;
[0125] b) a linear saturated alkyl group in C1-C6 or in C3-C6 branched optionally substituted by one or more groups, which may be identical or different, selected from:
[0126] i) -O-R3
[0127] ii)-S-R3;
[0128] preferably optionally substituted by one or more groups i)
[0129] R2 denotes a radical chosen from:
[0130] a) a hydrogen atom;
[0131] b) a linear saturated hydrocarbon group in C1-C10 or branched in C3-C10 or cyclic in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, selected from:
[0132] i) -O-R3
[0133] ii) -SR-,
[0134] iii) -C(O)-O-R3 ;
[0135] iv) a phenyl group optionally substituted by one or more hydroxyl groups and / or by one or more Ci-C4 alkoxy radicals such as methoxy;
[0136] preferably substituted by one or more groups selected from i) and iii), preferably iii) such as carboxy
[0137] R3 designates a radical chosen from:
[0138] a) a hydrogen atom;
[0139] b) a linear saturated alkyl group in Ci-C6 or branched in C3-C6;
[0140] Preferably, the compounds of formula (I) and the tautomer (!') or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture;
[0141] have the following meanings:
[0142] Ri designates a radical chosen from:
[0143] a) a hydrogen atom;
[0144] b) a linear saturated alkyl group in Ci-C4 or in C3-C4 branched optionally substituted by one or more groups, which may be identical or different, chosen from i) -OR3>plus preferably unsubstituted;
[0145] R2 denotes a radical chosen from:
[0146] a) a hydrogen atom;
[0147] b) a linear saturated hydrocarbon group in C1-C10 or branched in C3-C10 or cyclic in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, selected from:
[0148] i) -O-R3
[0149] iii) -C(O)-O-R3 ;
[0150] iv) an aryl group in C5-Ci2, optionally substituted by one or more hydroxyls and / or by one or more alkoxy radicals in C1-C4;
[0151] R3 denotes a radical chosen from:
[0152] a) a hydrogen atom;
[0153] b) a linear saturated alkyl group in C1-C4 or branched in C3-C4 such as methyl or ethyl.
[0154] Preferably, the compounds of formula (I) and the tautomer (I1) or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture;
[0155] have the following meanings:
[0156] Ri is a hydrogen atom; and
[0157] R2 denotes a radical chosen from:
[0158] a) a hydrogen atom;
[0159] b) a linear saturated hydrocarbon group in C1-C5 or branched in C3-C5 or cyclic in C3-C8 as in C5-C6, optionally substituted by one or more groups, which may be identical or different, selected from v) -C(O)-O-R3, preferably substituted by a iii) -C(O)-O-R3 group;
[0160] R2 is even more preferably a linear saturated hydrocarbon group in C1-C4 or branched in C3-C4 substituted by a group iii) -C(O)-OR3.
[0161] According to another preferred embodiment, the compounds of formula (I) and the tautomer (I1) are selected from the compounds of formula (11) as well as their tautomers, their salts, their solvates and their optical isomers, and their racemates, alone or in mixture: O ... JL .X, 0, y -y- U to, « H 0 - K .x 0. y Y -yy -,¾ Gl} an
[0162] Formulas (I) and (!') in which RI and R3 have the same meaning as for the compounds of formula (I) and (!') and X denotes an alkylene radical -(CH2)n- with n being an integer from 1 to 10 inclusive, preferably from 1 to 6, more preferably from 1 to 4, such that 1, preferably R3 represents a hydrogen atom.
[0163] Preferably, compounds of formula (I), the following compounds are preferably used, and their tautomer or their salts, their optical isomers, racemates, and / or solvates such as hydrates and their derivatives, alone or in mixture: Na. Chemical Structure CAS No. 1 M i HH N-ethyl-?-th=oxo-1,2-dihydropyridine-3-carboxamide 91859-75-5 2 / / Xy X. y N-methylk2-Wioxo-1,2-dihydropyridine-3-carboxamide 91859-74-4 3 .->'A x N-oc^l-24hiaxo-1,2-dthydrop^ndme-3-çarboxa^sde 31859-77-7 4 ,.$x Z .-ZYs -Xy.-> 'x;:- ^-benzyl-2-t^yrcarbox-amidehy ,2 91859-79-9 / / 'v\ K^phén^-2-îhfoxû-1,2-dÈhydropynd^e-3-carboxai^ide 194857-16-1 e j7' 'YY"'"" '! Z'"'' ■4 ^cydohexyl-2-ïhÊGXo-1,2-dihydropyridÎFie-3-caïboxamidte 91859-78-8 7 N-}2-(4- ihoxü-1,2- AIhydropynd^p-3.3- carbokam^de 323-*"J'682 '88 x-** S •;< thioxo-l 2- dihydropyrsd^e-3-carboxamsde 1188927-79-9 9 r--'y ? - ' "' Y: ' ' K v-"' ' ■■■ •.■''■' N^pentyî-2. dihydropyndme-3-carboxamads 330667-57-7 wn -A TT N-nony^2-îhtoxo-1 / 2-dihydropyridiise-3-earboxafrade W31149-44-6 11 0 a^a'^a* | a' xœ As ■■i N-(2-hydroxyé^^^^ ttiioxo-12-dthydropyridme-3~ earboxam^de 12 a AAlZA, Il XV ''■\'z 'À ZM H btN-OwU-mer captcnfcotm amide 13 « '1 À v !\ H ' A N-éthy1-M-(2-hvdroxy^1hyl)-2-thtoxo 1 2-dihydfûpyridtne-3-caib^xamàde 14 ■•< :S> rh - f A ,A, A Av A: ï ï ....... N-(2 3-dihydro-xyprçpÿl)-2-tA <<>1 2-dthydropyrÉdine-3-carboxamsde 15 ee-H il 1 f T '-...... A''" 'A N-(1,3-dihydroxypropan^-yi)-2-4^0X0-12-dihÿdropyrÈdhe-3-carboxamsde 16 <.-.C N-[^2-thsüxo-1 2-dhydsapyHdia-3- K arbpoy(|a in<g; dethyie 17 " Jx X’S. N-{{2:-thiQX0-1,2-dfhydfopyrtdm-3-> OgartQQ>ÜP^(?Yl alaqin^e of ethyle 18 N-«yethyl-N4^ 1,2-dïhydropyridtn-3- of eîhye 19 N-IP-thsc^oV-dthyckopyridîïi-3- of ethyl 20 1; N-[(2-thî0xo-1.2-dihydropyrîdm-3- 21 H ' N^é^lh^24hiôxG-1,2-dihy{lrGpyridtn-3-y 0ç<â&!wiisiy « 22 N,N-bis(2-hydr©xyethyli^24htaxo--1,2-d:ihydrepyndine-3-carboxsmide 23' p
[0164] Among these compounds, the following compounds are particularly preferred: Compound, Compound Structure: chemical CAS Compound. 1 -^z :: : H N-éthvf24hhxG-12-dfhydmpyridsne-3-çarboxamide 91859-75-5 2 y7"""Y N-methy^-24hKïxo-1.2-dIhydropyndine-3-carbopyndine-3-carbopyndïne 494 N-benzyî-2-thioxo-12-di hy dmpÿncfce-3-carboxamide 91859-79-9 6 o 'Y N-cydoh exy^-2-thioxo-12-dihydrapynding-3-carboxamide 91859-78-8 >' M-[2-(4- 24hioxa-1,2-dthÿdropyridîne-3-carboxamide 923632-88-6 9 N-pe^tyl-2-îhioxo-l .2-dfhydrépyridsné-3-carboxamkle 330-H761-57 M424iydroxyédiy1)-2- dfhydropyndine-3-carboxamide 12 : Q NN-^éthy 1 2- mercaptonicsfcamide 14 $ xS N-Ï2.3- dfhydroxypî'opyï)-2- thtoxü-1,2ami-315-dihydropyrboxidine -'■ '' :',■ >■'' ' !•' dihydFpxypropan-2-yl)-2-*hî0XG-1,2-dfhydropyndine-3- ciubcxamide Ethyte VW: dyv' !*H(2-thÎ0xo-1,2-dfhydmpÿiidm-3- V. -aX. . '' of ethyl 19 20 1 i H h NJ(2-th!oxo-12-dfhydropyridsn-3- i N-methyl-N-((24h8Qxo-1,2-dihydrspyridtn-3-vOg.ar^Qnÿ08^cme H [ LI 21 H
[0165] Better still, among these compounds, the following compounds are particularly preferred: Chemical Structure No. CAS No. 1 A CH: H-ethyl2-thioxo-1,2-dihydropyridic acid-3-carboxamide 91853-75-5 9 H-peutyl-2-thioxo-1,2-dihydropyridic acid-3-carboxamide 338667-57-7 16 A to .. ■> .•■■' ^x'y-'' A;'' M-.d M-[(24thioxo-1,2-dihydropyridic acid-3-carboxamide) 18 ■X ..-^, „AX xzx A 'x '' SN - methyl-N-{(24thioxo-1,2-dihydropyridic acid-1 ... ï N4(2-th®xo-1,2-dthÿdnjpyfisfe-3- ethyl 20 ..■'Ax ihh X --^x ■'■ H-[(24hiaxo-1,2-dihydæpynd§n-3-y%a^WllSÈydne N-methYM-[(2-thisxc-1..2^ihydropyrfcfa-3-
[0166]
[0167] Even more preferentially, among these compounds, the following compounds are particularly preferred: No. Structure Chemical Name CA S No. 18 s fVYV 'X. '"'■s N-[(2-thhxe-1,2-dthÿdropyndin-3-yOç^iwilsb'^e 21 û f YYYH N-methylW4(2-îhioxo-1.2-dihydrapy ridin-3-yQç^^nyijgiydne In a most preferred embodiment, the compound according to this disclosure is as follows: -c N-[(2-ihsoxe-1,2-dthydropyridi^-Sy^çjikwil§b'c^e 'v\- 20
[0168] All the compounds can be obtained by a chemical process known to those skilled in the art, using commercially available reagents. For example, the synthesis process disclosed in European patent application EP3 390 363 can be used.
[0169] The composition used according to the disclosure comprises at least one compound of formulas (I) and / or (II) as described above, in a physiologically acceptable medium.
[0170] Compound (I), (I'), (II) and / or (II1) may be present in the composition used according to the disclosure in an amount which may be, 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. Hydrophilic antioxidants
[0171] One or more hydrophilic antioxidants may be selected from the group consisting of polyphenols and their esters; ascorbic acid (vitamin C) and its esters; and their pharmaceutically acceptable salts. The polyphenols are typically catechins; leucoanthocyanidins and flavanones; flavanins, flavones and anthocyanins; flavonols; flavonolignans; and their oligomers. Ascorbic acid and its derivatives
[0172] Cosmetic compositions contain ascorbic acid and its derivatives.
[0173] The composition according to the disclosure comprises ascorbic acid or one of its derivatives, in a maximum content of 20% by weight relative to the total weight of the composition.
[0174] Ascorbic acid as defined in the disclosure preferably corresponds to L-ascorbic acid, or vitamin C. Its structure is of formula (A):
[0175] [A]
[0176] By "ascorbic acid derivative" is preferably meant a compound selected from 5,6-di-O-dimethylsilyl ascorbate (in particular sold by Exsymol under the reference PRO-AA), the potassium salt of DL-alpha-tocopheryl-DL-ascorbyl phosphate also known as potassium ascorbyl tocopheryl phosphate (sold by Senju Pharmaceutical under the reference S EPC), magnesium ascorbyl phosphate, sodium ascorbyl phosphate (sold by Roche under the reference Stay-C 50), disodium ascorbyl sulfate, ascorbyl palmitate, tetrahexadecyl ascorbate, ascorbyl tetraisopalmitate, 3-O-ethyl ascorbic acid, sulfinyl-L-ascorbic acid, glucopyranosyl-L-ascorbic acid and ascorbyl glucoside.
[0177] The term "ascorbyl glucoside" means the condensation product of glucose, in the D form, i.e. in the form of glucopyrannose a or [3 or furannose a or [3, or in the L form, with ascorbic acid, preferably in the L form. Ascorbyl glucoside is the 2-OaD-glucopyranoside of L-ascorbic acid, available in particular from the company HAYASHIBARA.
[0178] Preferably, the composition according to the invention comprises ascorbic acid, preferably L-ascorbic acid.
[0179] The composition preferably comprises from 0.1% to 20% by weight of ascorbic acid or one of its derivatives, relative to the total weight of the composition, preferably from 1% to 15% by weight relative to the total weight of the composition.
[0180] Ascorbic acid and its derivatives may be present in a total quantity of 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, 10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 17.5, 18, 18.5, 19, 19.5 or 20% by weight depending on the total weight of the composition. pH correcting agent
[0181] The composition according to the present invention may comprise at least one pH corrector. Two or more pH correctors may be used in combination. Thus, a single type of pH corrector or a combination of different types of pH correctors may be used.
[0182] As a pH correcting agent, at least one acidifying agent and / or at least one basifying agent (alkaline agent) may be used.
[0183] The acidifying agent may be a monovalent or polyvalent acid, such as divalent.
[0184] Acidifying agents may be, for example, mineral (inorganic) acids such as hydrochloric acid, sulfuric acid, phosphoric acid, or organic acids such as carboxylic acids, for example tartaric acid, citric acid and lactic acid, as well as sulfonic acids.
[0185] The alkalizing agent may be a monovalent or polyvalent base, such as divalent. Alkalizing agents may be mineral (inorganic) or organic, or hybrid.
[0186] Mineral alkalizing agents may be selected 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.
[0187] Organic alkalizing agents may be selected from organic amines whose pKb at 25 °C is less than 12, preferably less than 10, and even more advantageously less than 6. It should be noted that this is the pKb corresponding to the highest basicity functional group. Furthermore, the organic amines do not include any alkyl or alkenyl fatty chain comprising more than ten carbon atoms.
[0188] The organic alkalizing agent may be chosen, for example, from the alkanolamines, oxyethylenated and / or oxypropylenated ethylenediamines, amino acids and amine compounds of formula (III) below: hw--
[0189] in which
[0190] W represents a divalent Ci-C6 alkylene radical optionally substituted by one or more hydroxyl groups or a Ci-C6 alkyl radical, and optionally interrupted by one or more heteroatoms such as O and N, and
[0191] Rx, Ry, Rz and Rt, which may be identical or different, represent a hydrogen atom or an alkyl radical in Ci-C6, hydroxyalkyl in Ci-C6, or aminoalkyl in CrC6.
[0192] Examples of amine compounds of formula (III) that may be cited include 1,3-diaminopropane, 1,3-diamino-2-propanol, spermine and spermidine.
[0193] The term "alkanolamine" designates an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or CrC8 branched alkyl groups bearing one or more hydroxyl radicals.
[0194] Alkanolamines such as monoalkanolamines, dialkanolamines or trialkanolamines comprising one to three identical or different C1-C4 hydroxyalkyl radicals may be suitable for the present invention. Examples of such compounds include 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.
[0195] The 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 among the carboxylic acid, sulfonic acid, phosphonic acid or phosphoric acid functions. The amino acids may be in neutral or ionic form.
[0196]
[0197]
[0198]
[0199]
[0200] Examples of amino acids that may be used in the present invention include aspartic acid, glutamic acid, alanine, arginine, omithine, citrulline, asparagine, camitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine. It may be preferable for amino acids to be basic amino acids comprising an additional amine function optionally included in a ring or in a ureido function. Such basic amino acids may preferably be chosen from those corresponding to formula (IV) below: NH (IV) / : £ / R-CH, CHv CO.H in which R represents a group chosen from:
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207] -(CH2)3-NH2, -(CH2)2-NH2, -(CH2)2-NH-CO-NH2, and Compounds corresponding to formula (IV) include histidine, lysine, arginine, ornithine, and citrulline. The organic alkalizing agent can be chosen from among the heterocyclic organic amines. In addition to histidine, which has already been mentioned among the amino acids, the following compounds can be cited in particular: pyridine, piperidine, imidazole, triazole, tetrazole, and benzimidazole. The organic alkalizing agent can also be chosen from amino acid dipeptides. Examples of amino acid dipeptides that can be used in the present invention include carnosine, anserine, and balein. The organic alkalizing agent can also be chosen from compounds containing a guanidine functional group. Amines of this type can be Used in the present invention, besides arginine, which has already been mentioned as an amino acid, include in particular creatine, creatinine, 1,1-dimethylguanidine, 1,1-diethylguanidine, glycocyamine, metformin, agmatine, N-amidinoalanine, 3-guanidinopropionic acid, 4-guanidinobutyric acid and 2-([amino(imino)methyl]amino)ethane-l-sulfonic acid.
[0208] In a preferred embodiment of the present invention, the organic alkalizing agent may be selected from amino acids, preferably basic amino acids, and more preferably arginine, lysine, histidine, or mixtures thereof. Even more preferably, the organic alkalizing agent may be arginine.
[0209] Examples of hybrid compounds that may be cited include salts of the amines mentioned above with acids such as carbonic acid or hydrochloric acid. Guanidine carbonate or monoethanolamine hydrochloride may be used in particular.
[0210] The pH correcting 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.
[0211] The pH correcting 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.
[0212] The pH correcting agent may be present in an amount 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.
[0213] It is preferable that the composition according to the present invention has a pH of 4.5 or more, and more preferably of 5 or more.
[0214] It is preferable that the composition according to the present invention has a pH of 6.5 or less and, even better, of 6 or less.
[0215] It is preferable that the composition according to the present invention has a pH of 4.5 to 6.5 and, even better, of 5 to 6.
[0216] The pH of the composition means the pH of the aqueous phase of the composition according to the present invention.
[0217] It may be preferable that at least one buffer or buffering agent also be used, such as the pH correcting agent, in combination with the acidifying agent and / or the alkalizing agent, in order to stabilize the pH of the composition according to the present invention.
[0218] As a buffer, any commonly known buffer 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 can be used as a buffer if citric acid or lactic acid is used as the acidifying agent. Cosmetically acceptable vector system
[0219] Cosmetic compositions comprise a cosmetically acceptable carrier system. The term “cosmetically acceptable” means a carrier that is compatible with any keratinous substrate and, for the purposes hereof, comprises water and, optionally, water-based solvents, subject to any exclusions as disclosed herein.
[0220] Cosmetic compositions may include any constituent normally used in the intended topical application and administration. This may include, in particular, water, solvents, polyols, compounds (i.e., those described by the International Federation of Cosmetic Chemical Societies, for example in Cosmetic Raw Material Analysis and Quality, Volume I: Hydrocarbons, Glycerides, Waxes and Other Esters (Redwood Books, 1994), pigments, fillers, silicones, surfactants, thickeners, gelling agents, preservatives, chelating agents and mixtures thereof in any proportion.
[0221] The composition used according to the invention may then include any adjuvant commonly used in the cosmetic field. Usage methods
[0222] This disclosure also relates to processes for using the cosmetic compositions described herein. For example, the cosmetic compositions may be used in a process that includes applying the cosmetic compositions to human skin. In some cases, the composition is applied to the face. Furthermore, the cosmetic composition may be used in processes for depigmenting, lightening, and / or bleaching keratinous materials, preferably of the skin, comprising the step of applying the composition to the keratinous substance according to the compositions described herein. The aforementioned processes are not therapeutic.
[0223] The cosmetic composition may be applied once a day, twice a day, or more than once or twice a day. In some cases, the composition is applied in the evening before bedtime. 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 period 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 weeks or more, or months.
[0224] This disclosure also relates to a non-therapeutic cosmetic process for the depigmentation, lightening and / or bleaching of keratinous materials, preferably skin, comprising the step of applying the composition according to the compositions described herein to the keratinous substance.
[0225] These and other aspects of the invention are described in more detail in the detailed description of the invention.
[0226] This disclosure describes exemplary embodiments according to general inventive concepts and is not intended to limit the scope of the invention in any way. Indeed, the invention as described in the specification is broader than and not limited by the exemplary embodiments presented herein, and the terms used herein have their full ordinary meaning. EXAMPLES
[0227] An implementation of this disclosure is provided by means of the following examples. The following examples are intended to explain certain aspects of the technology without being limited by their nature. Example 1
[0228] Example 1: Synthesis of compound 20
[0229] Compound 20 is synthesized as disclosed in Example 2 of patent EP3 390 363. Example 2 (Inventive compositions)
[0230] Inventive compositions
[0231] [Tables 1] Ingredients INCI US Ex. Invent. 1 Ex. Invent. 2 a Thiopyridine (THP) type compound 0.50 0.50 b Ascorbic acid 10.00 10.00 Fatty compounds Fatty compounds 10 10 Polymers Polymers 1.5 1.5 Emulsifiers Emulsifiers 2.5 2.5 Filler Filler 2.0 2.0 Chelating agent Chelating agent 0.11 0.11 Active compounds Active compounds 1.0 1.0 Plant extract Plant extract 0.50 Preservative Preservative 0.80 0.80 Solvent Solvents 6.21 6.21 pH adjuster pH adjuster 2.20 2.20 QS Water 62.58 62.07 Example 3
[0232] Inventive examples 1 and 2 and several comparative examples were tested for their stability. The stability of the inventive and comparative examples was assessed by following the procedure described below.
[0233] The crude formula was added to a 30 mL aluminum tube, which was then crimped and sealed. A freshly prepared initial sample (T0) was subjected to the thiopyridone (THP) assay. The 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, the samples were removed and subjected to the thiopyridone (THP) assay. The % remaining, shown in Table 2, compares the 2-month sample at 45 °C to the initial sample T0 and is presented as the % of THP remaining in the sample compared to T0. The assay was performed by high-performance liquid chromatography with a UV detector.
[0234]
[0235]
[0236] The results are presented in Table 2 below. Stability Results [Table 2] Vitamine C THP Exe mples Ini tial T1M 25 T1M 45 T2M 25 T2M 45 % r estant Ini tial T1M 25 T1M 45 T2M 25 T2M 45 % r estant Vit C uni que men t Com p. Ex. 1 H, 30 % 9,93 % 9,37 % 9,84 % 8,82 % 78,05 % N / A Com p. Ex. 2 H, 16 % 10, 15 % 9,43 % 9,66 % 9,00 % 80,65 % Com p. Ex. 3 10, 94 % 10, 22 % 9,50 % 9,95 % 9,50 % 86,84 % Com p. Ex. 4 10, 53 % 9,82 % 9,16 % 10 % 8,97 % 85,19 % Com p. Ex. 5 10, 54 % 9,82 % 8,97 % 10, 11 % 8,62 % 81,78 % Com p. Ex. 6 H, 01 % 9,91 % Écl ate men t du tube 10, 36 % Écl ate men t du tube Éclate men t du t ube Vit C + THP Ex. In ventif 1 8,70 % 9,45 % 9,06 % 9,76 % 8,98 % ~ 100 % 0,47 % 0,46 % 0,45 % 0,50 % 0,49 % ~ 100 % Ex. In ventif 2 9,72 % 9,01 % 8,71 % 9,67 % 8,89 % 91,46 % 0,48 % 0,47 % 0,46 % 0,50 % 0,49 % ~ 100 % THP un iqu eme nt Com p. Ex. 7 N / A 0,5 12 % 0,4 93 % 0,4 61 % 0,4 66 % 0,4 18 % 81,64 %
[0237] As shown above, inventive examples 1 and 2, containing both vitamin C and THP (a thiopyridinone-type compound), demonstrated that the chemical stability of THP and vitamin C increased when the two molecules were combined. They exhibited between 91% and 100% stability for both active ingredients. The combination of vitamin C and THP also improved efficacy. The greater stability resulted in a higher overall concentration of the active ingredient when the consumer received and used the product. For example, if the formula contains 10% vitamin C alone and is unstable, if 40% of the vitamin C degrades, only 6% of the vitamin C remains.However, if there is a combination of Vit C and THP (= Thiopyridinone type compound), and the Vit C hardly degrades, the Vit C will still be around 10% Vit C (i.e., 10% Vit C will be more effective than 6% Vit C).
[0238] Comparative examples 1, 2, 3, 4, 5 and 6 containing only vitamin C showed stability between 78% and 86%.
[0239] Comparative example 7 containing only a Thiopyridinone type compound demonstrated that the association of Vit C and THP improved the stability of THP when combined with Vit C than when alone.
[0240] Data show that cosmetic compositions according to this disclosure, containing vitamin C and THP (= Thiopyridinone type compound), are surprisingly stable.
[0241] Although the disclosure has been described with reference to described embodiments, it will be understood by those skilled in the art that various modifications can be made and equivalents can be substituted for elements thereof without departing from the scope of the disclosure. Furthermore, numerous modifications can be made to adapt a particular situation or subject matter to the teachings of the disclosure without departing from its essential scope. Therefore, it is intended that the disclosure will not be limited to the particular embodiment disclosed as being the best envisaged means of carrying out that disclosure, but that the disclosure will include all embodiments falling within the scope of the claims.
[0242] The term “INCI” is an abbreviation for International Nomenclature of Cosmetic Ingredients, which is a system of names provided by the International Nomenclature Committee of the Personal Care Products Council to describe the ingredients of personal care products.
[0243] “At least one”, as used herein, means one or more and thus includes individual components as well as mixtures / combinations.
[0244] The term "including" is intended to be inclusive or broad and does not exclude any additional element, process, step, or material not mentioned. The expression "consisting of" excludes any element, step, or material other than those specified and, in the latter case, impurities ordinarily associated with the specified material(s). The expression "consisting essentially of" limits the scope of a claim to the specified elements, steps, or materials and to those that do not materially affect the fundamental and innovative feature(s) of the claimed disclosure. All the materials and processes described herein that embody this disclosure may, in other embodiments, be defined more specifically by any of the transitional terms "including," "consisting essentially of," and "consisting of."
[0245] The terms "free" and "devoid" indicate that no reliably measurable excluded material is present in the composition, typically 0% by weight, relative to the total weight of the composition. The term "essentially free" means that, although it is preferable that no excluded material be present in the composition, it is possible to have very small amounts of the excluded material in the composition of the invention, provided that such amounts do not materially affect the advantageous properties of the composition. In particular, "essentially free" means that the excluded material may be present in the composition in an amount of less than about 0.1% by weight, relative to the total weight of the composition.
[0246] All percentages and ratios are calculated by weight unless otherwise stated. All percentages are calculated relative to the total composition unless otherwise stated. In general, unless expressly stated otherwise herein, "weight" or "quantity" as used herein with respect to the percentage of an ingredient refers to the quantity of raw material comprising the ingredient, the raw material being described herein as comprising less than and up to 100% of the ingredient's activity. Therefore, the percentage by weight of an active ingredient in a composition represents the quantity of raw material containing the active ingredient that is used and may or may not reflect the final percentage of the active ingredient, the final percentage of the active ingredient being dependent on the percentage by weight of the active ingredient in the raw material.
[0247] The terms "percent by weight" and "% by weight" may be used interchangeably and mean the percentage by weight, relative to the total weight of a composition, article, or material, except as may be specified with respect to, for example, a phase or system that is a component of a composition, article, or material. All ranges and quantities stated herein are intended to include subranges and quantities using any disclosed point as a boundary. Thus, a range of "1% to 10%, such as 2% to 8%, such as 3% to 5%" is intended to encompass ranges of "1% to 8%", "1% to 5%", "2% to 10%", and so on. All figures, quantities, ranges, etc., are intended to be modified by the term "approximately," whether or not it is expressly stated. Similarly, a given range of "approximately 1% to 10%" is intended to have its 1% and 10% limits modified by the term "approximately." Furthermore, it is understood that when a quantity of a component is given, it is assumed to mean the quantity of active ingredient, unless expressly stated otherwise.
[0248] Although the numerical ranges and parameters defining the general scope of the disclosure are approximations, unless otherwise indicated, the numerical values presented in the specific examples are reported as accurately as possible. However, every numerical value inherently contains some errors necessarily resulting from the standard deviation observed in their respective test measurements. The following example serves to illustrate embodiments of this disclosure but is not, however, limiting in nature.
Claims
Demands
1. Cosmetic composition including: (i) at least one compound selected from the compounds of formula (I) and the tautomer of formula (!') below; and their salts, optical isomers, racemates, and / or solvates such as hydrates, alone or in mixtures: (I) Formulas (I) and (I') in which: -Ri designates a radical chosen from: a) a hydrogen atom; b) a linear saturated alkyl group in C1-C10 or C3-C10 branched form optionally substituted by one or more groups, which may be identical or different, chosen from: i) -O-R3 ii) -S-R3; - R 2 designates a radical chosen from: a) a hydrogen atom; b) a saturated hydrocarbon group in linear C1-C12 or branched C3-Ci2 or cyclic C3-C8, optionally substituted by one or more groups, which may be identical or different, chosen from: i) -O-R3 ii) -S-R3 iii) -C(O)-O-R3; (iv) an aryl group in C5-C12, optionally substituted by one or more hydroxyl groups and / or by one or more Cr C8 alkoxy radicals; c) an aryl group at C5-C12, optionally substituted by one or more hydroxyl groups and / or by one or more Cr alkoxy radicals -R3 designates a radical chosen from: a) a hydrogen atom; b) a linear saturated alkyl group in Ci-Cio or branched in C3-CiO; and ii) ascorbic acid.
2. Composition according to any one of the preceding claims, wherein ii) ascorbic acid is present from about 0.1 to about 20% by weight, relative to the total weight of the cosmetic composition.
3. Composition according to any one of the preceding claims, wherein ascorbic acid is present from about 1 to about 15% by weight, relative to the total weight of the cosmetic composition.
4. Composition according to any one of the preceding claims, wherein i) the thiopyridinone type compound is present from about 0.01 to about 10% by weight, relative to the total weight of the cosmetic composition.
5. Composition according to any one of the preceding claims, wherein i) the thiopyridinone type compound is present from about 0.1 to about 5% by weight, relative to the total weight of the cosmetic composition.
6. Composition according to any one of the preceding claims, wherein the pH is from about 4.5 to about 6.5, preferably from about 5 to about 6.
7. A skin treatment method comprising applying a cosmetic composition according to claim 1 to the skin.