WO2013081146A1 - Produit cosmétique antirides - Google Patents

Produit cosmétique antirides Download PDF

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Publication number
WO2013081146A1
WO2013081146A1 PCT/JP2012/081191 JP2012081191W WO2013081146A1 WO 2013081146 A1 WO2013081146 A1 WO 2013081146A1 JP 2012081191 W JP2012081191 W JP 2012081191W WO 2013081146 A1 WO2013081146 A1 WO 2013081146A1
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Prior art keywords
group
salt
alkyl group
derivative
cysteine derivative
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PCT/JP2012/081191
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English (en)
Japanese (ja)
Inventor
瀧野　嘉延
冬美恵 大倉
愼二 黒田
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味の素株式会社
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Priority to JP2013547254A priority Critical patent/JP5994789B2/ja
Publication of WO2013081146A1 publication Critical patent/WO2013081146A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • 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
    • 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
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/606—Nucleosides; Nucleotides; Nucleic acids
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products 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
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/58—Metal complex; Coordination compounds
    • 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists

Definitions

  • the present invention relates to a cosmetic useful for preventing wrinkles containing a specific cysteine derivative.
  • a major cause of wrinkles and sagging associated with skin aging is thought to be related to a decrease in the amount of collagen in the dermis.
  • Collagen amount is an important factor constituting the softness and tension of the skin.
  • it is important to inhibit collagenase activity induced by UV irradiation, suppress collagen degradation, and promote collagen production.
  • substances that promote collagen production they are not always satisfactory in terms of stability, safety and wrinkle prevention effect.
  • Patent Document 1 describes that a cysteine derivative obtained by esterifying L-2-methylthiazolidine-2,4-dicarboxylic acid or a salt thereof is useful as a whitening agent.
  • Patent Document 2 describes that 2-methylthiazolidine-2,4-dicarboxylic acid or a derivative thereof has a whitening action.
  • these derivatives have not been put into practical use because they are easily decomposed and are not sufficiently stable.
  • the specific cysteine derivative of the present invention is not described, and the wrinkle prevention effect is not described.
  • the present invention is as follows.
  • the cysteine derivative or a salt thereof is N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester, And the cosmetic according to [1] or [2] above, which is one or more selected from salts thereof.
  • the component (B) is one or more selected from retinoic acid, retinol, vitamin E, pyrrolidone carboxylic acid zinc salt and milk-derived peptide.
  • the cysteine derivative or a salt thereof is N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester or a salt thereof, and (B) the component is vitamin A or a derivative thereof
  • (A) The cysteine derivative or a salt thereof is N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester,
  • the collagen production promoter according to [8] or [9] above which is one or more selected from salts thereof.
  • the cysteine derivative or a salt thereof is N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester or a salt thereof, and (B) the component is a pyrrolidone carboxylic acid zinc salt
  • the collagen production promoter according to any one of [13].
  • a pharmaceutical external preparation containing [16] (B) The topical medicine according to the above [15], further comprising one or more selected from vitamin A or a derivative thereof, vitamin E or a derivative thereof, zinc salt, ubiquinone, peptide, amino acid and nucleic acid Agent.
  • a cysteine derivative represented by the general formula (I) or a salt thereof as an anti-wrinkle cosmetic [Where: X and Y are each independently OR 1 , NHR 2 (wherein R 1 and R 2 each independently represents a hydrogen atom or a C 1-22 alkyl group); Z represents a hydrogen atom or a C 1-22 alkyl group; W represents a C 1-22 alkyl group, a C 1-22 alkoxy group or a C 1-22 alkylamino group. ] Use of.
  • a collagen production promoter having high stability and safety can be provided, and as a result, a cosmetic having an excellent anti-wrinkle effect and the like can be provided.
  • the present invention is a cosmetic containing (A) a specific cysteine derivative or a salt thereof, and optionally (B) a specific collagen production promoting compound. Moreover, this invention is a collagen production promoter containing (A) and optionally (B), and this is applicable as cosmetics (including quasi-drugs), medicines and the like.
  • the cysteine derivative of the present invention is a cysteine derivative represented by the general formula (I) or a salt thereof.
  • X and Y are each independently OR 1 , NHR 2 (wherein R 1 and R 2 each independently represents a hydrogen atom or a C 1-22 alkyl group); Z represents a hydrogen atom or a C 1-22 alkyl group; W represents a C 1-22 alkyl group, a C 1-22 alkoxy group or a C 1-22 alkylamino group. ]
  • C 1-22 alkyl group means a linear or branched hydrocarbon group having 1 to 22 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a propyl group, a butyl group, Isobutyl, sec-butyl, tert-butyl, pentyl, sec-pentyl, tert-pentyl, isopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, tert-octyl, nonyl , Isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, tridecyl group, isotridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, isohexadecc
  • C 1-16 alkyl group examples include methyl group, ethyl group, isopropyl group, propyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, sec-pentyl group, tert-pentyl group.
  • C 1-6 alkyl group examples include methyl group, ethyl group, isopropyl group, propyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, sec-pentyl group, tert-pentyl group. Group, isopentyl group, hexyl group and the like.
  • C 1-22 alkoxy group means a hydroxyl group substituted with the above “C 1-22 alkyl group” and includes, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, tridecyloxy group, tetradecyloxy group, pentadecyloxy group Hexadecyloxy group, heptadecyloxy group, octadecyloxy group, nonadecyloxy group, eicosyloxy group, heneicosyloxy group, docosyloxy group and the like.
  • C 1-6 alkoxy group examples include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, tert-butoxy group, pentyloxy group, hexyloxy group and the like.
  • the “C 1-22 alkylamino group” means an amino group substituted with the above “C 1-22 alkyl group” and includes, for example, a methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, butyl Amino group, isobutylamino group, tert-butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, nonylamino group, decylamino group, undecylamino group, dodecylamino group, tridecylamino group, tetra Examples include decylamino group, pentadecylamino group, hexadecylamino group, heptadecylamino group, octadecylamino group, nonadecylamino group, ei
  • C 1-6 alkylamino group examples include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, tert-butylamino group, pentylamino group, and hexylamino group. Can be mentioned.
  • Halogen atom includes chlorine atom, bromine atom, fluorine atom and iodine atom.
  • X and Y are each independently OR 1 , NHR 2 (wherein R 1 and R 2 each independently represents a hydrogen atom or a C 1-22 alkyl group).
  • the “C 1-22 alkyl group” represented by R 1 or R 2 is preferably a C 1-6 alkyl group, more preferably a methyl group, an ethyl group or an isopropyl group, still more preferably an ethyl group. is there.
  • X is preferably OR 1 (wherein R 1 is as defined above); more preferably OR 1 ′ (wherein R 1 ′ is a hydrogen atom or a C 1-6 alkyl group (preferably Represents a methyl group, an ethyl group, or an isopropyl group); and more preferably a hydroxyl group, a methoxy group, an ethoxy group, or an isopropoxy group, and even more preferably a hydroxyl group or a methoxy group.
  • Y is preferably OR 1 (wherein R 1 is as defined above), more preferably OR 1 ′ (wherein R 1 ′ is as defined above), More preferred is a hydroxyl group, a methoxy group, an ethoxy group or an isopropoxy group, and even more preferred is a hydroxyl group or a methoxy group.
  • Z represents a hydrogen atom or a C 1-22 alkyl group.
  • the “C 1-22 alkyl group” represented by Z is preferably a C 1-6 alkyl group, more preferably a methyl group.
  • Z is preferably a hydrogen atom or a C 1-6 alkyl group, more preferably a hydrogen atom or a methyl group.
  • W represents a C 1-22 alkyl group, a C 1-22 alkoxy group or a C 1-22 alkylamino group.
  • the “C 1-22 alkyl group” represented by W is preferably a C 1-16 alkyl group, more preferably a methyl group, a nonyl group, or a pentadecyl group, and still more preferably a methyl group.
  • the “C 1-22 alkoxy group” represented by W is preferably a C 1-6 alkoxy group, more preferably a tert-butoxy group.
  • the “C 1-22 alkylamino group” represented by W is preferably a C 1-6 alkylamino group.
  • W is preferably a C 1-22 alkyl group or a C 1-22 alkoxy group, more preferably a C 1-16 alkyl group or a C 1-6 alkoxy group, still more preferably a methyl group, a nonyl group, A pentadecyl group and a tert-butoxy group are preferable, and a methyl group and a tert-butoxy group are particularly preferable.
  • cysteine derivative represented by the general formula (I) include N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid, and N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid. Acid-2-ethyl ester is preferred, and N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester is more preferred.
  • Examples of the salt of the cysteine derivative of the present invention include a salt with an inorganic base and a salt with an organic base.
  • Examples of the salt with an inorganic base include sodium salt, potassium salt, calcium salt, magnesium salt, ammonium salt, zinc salt, silver salt and the like.
  • salts with organic bases include methylamine, diethylamine, trimethylamine, triethylamine, ethanolamine, diethanolamine, triethanolamine, ethylenediamine, tris (hydroxymethyl) methylamine, dicyclohexylamine, N, N'-dibenzylethylenediamine, guanidine , Pyridine, picoline, choline, cinchonine, meglumine, salts with amino acids (eg, arginine, lysine, etc.) and the like.
  • each salt can be obtained by reacting the cysteine derivative of the present invention with an inorganic base or an organic base.
  • the cysteine derivative and the salt thereof of the present invention have a collagen production promoting effect, they themselves have a wrinkle preventing effect and can be used as a collagen production promoting agent, a wrinkle preventing agent, and an anti-aging agent.
  • the anti-wrinkle agent referred to in the present invention is a concept including an anti-wrinkle agent and a therapeutic agent.
  • the cysteine derivative and the salt thereof of the present invention have a collagen production promoting effect, when applied to hair and eyelashes, the hair can be given firmness and elasticity by promoting the collagen production of the hair, It can be used as a hair nourishing agent, hair restoring agent, hair quality improving agent.
  • the lower limit when the cysteine derivative or a salt thereof is blended in a cosmetic is not particularly limited as long as the effect is exhibited, but 0.0001% by weight is preferably the lower limit. From the viewpoint that an effective effect can be exhibited, 0.001% by weight is more preferable, 0.01% by weight is further preferable, 0.1% by weight is still more preferable, 0.5% by weight is even more preferable, and 1% by weight. % Is particularly preferred.
  • the weight of the cysteine derivative portion (free body) is in the above range.
  • the upper limit in the case of blending the cysteine derivative or a salt thereof into the cosmetic is not particularly limited as long as the effect is exhibited, but 20% by weight is preferably the upper limit. 18% by weight is more preferred, 16% by weight is still more preferred, 12% by weight is even more preferred, 10% by weight is even more preferred, and 5% by weight is particularly preferred.
  • the weight of the cysteine derivative portion (free body) is in the above range.
  • cysteine derivative (I) is not particularly limited, and is produced by combining known methods. be able to. Specifically, it can be synthesized by the following method, but is not limited thereto.
  • Compound (IV) which is a precursor of cysteine derivative (I), can be synthesized by the following Step 1, and then cysteine derivative (I) can be synthesized by Step 2.
  • Compound (IV) may or may not be purified as necessary.
  • Step 1 Cysteine or a compound represented by general formula (II) obtained by esterification or amidation of cysteine in advance (hereinafter abbreviated as compound (II) and the same applies to compounds represented by other formulas). ) To form a ring by reacting with compound (III) to obtain compound (IV)
  • Compound (IV) can be obtained by reacting compound (II) with compound (III) in water or an alcohol such as methanol or ethanol for 5 to 24 hours.
  • an alcohol such as methanol or ethanol for 5 to 24 hours.
  • cysteine ethyl ester can be obtained, for example, by reacting cysteine in ethyl alcohol in the presence of hydrochloric acid or thionyl chloride at room temperature for about 5 to 24 hours.
  • cysteine amide is a protected cysteine and an amine in the presence of a dehydrating condensing agent such as EDCI ⁇ HCl (1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride), methylene chloride,
  • a dehydrating condensing agent such as EDCI ⁇ HCl (1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride
  • methylene chloride methylene chloride
  • Cysteine derivative (I) can be synthesized by reacting compound (IV) with compound (V) or compound (V ′) in the presence or absence of a solvent and in the presence or absence of a base.
  • the solvent include THF (tetrahydrofuran), ethyl acetate, isopropyl acetate, acetonitrile, acetone, ethanol, methanol, dichloromethane, water, or a mixture thereof, preferably THF, ethyl acetate, isopropyl acetate, acetonitrile, acetone, Dichloromethane, water, or a mixture thereof.
  • the base examples include organic bases such as triethylamine, diisopropylethylamine, pyridine and N-methylmorpholine, and inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate and potassium acetate.
  • organic bases such as triethylamine, diisopropylethylamine, pyridine and N-methylmorpholine
  • inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium acetate and potassium acetate.
  • the amount of compound (V) or compound (V ′) to be used is 1.0 to 5.0 mol, preferably 1.2 to 3.0 mol, per 1 mol of compound (IV).
  • the amount of the base used is 1.0 to 5.0 mol, preferably 1.2 to 4.0 mol, per 1 mol of compound (IV).
  • the reaction temperature is ⁇ 10 to 100 ° C., preferably 0 to 90 ° C.
  • the reaction time is 1 to 48 hours, preferably 3 to 20 hours. Further, this may be converted to other cysteine derivatives (I) by esterification, amidation, hydrolysis or acid anhydride.
  • a collagen production promoting compound When a collagen production promoting compound is combined as the component (B) with the cysteine derivative or salt thereof as the component (A), the wrinkle prevention effect is synergistically increased.
  • component (B) retinoic acid, retinol, tretinoin, retinol acetate, retinol palmitate, retinol propionate, hydrogenated retinol, tocopheryl retinoic acid and hydroxypinacolone retinoic acid, etc .; tocopherol, tocotrienol, linol Vitamin E or its derivatives such as tocopherol acid, tocopherol oleate, tocopherol succinate, tocopherol nicotinate, tocopherol phosphate and tocopherol acetate; pyrrolidone carboxylic acid zinc salt, zinc gluconate, zinc phenolsulfonate, zinc lactate, various Amino acid zinc salts, acylamino
  • One or more selected from vitamin A or a derivative thereof, vitamin E or a derivative thereof, a zinc salt and a peptide are preferable in terms of synergistically obtaining a wrinkle-preventing effect, and retinoic acid, retinol, vitamin E, One or more selected from pyrrolidone carboxylic acid zinc salts and milk-derived peptides are more preferred.
  • the collagen production promoting compound (B) may be used as a mixture of two or more.
  • the lower limit when blending the component (B) in the cosmetic is not particularly limited as long as the effect is exhibited, but 0.0001% by weight is preferably the lower limit. From the viewpoint that an effective effect can be exhibited, 0.001% by weight is more preferable, 0.01% by weight is further preferable, 0.1% by weight is still more preferable, 0.5% by weight is even more preferable, and 1% by weight. % Is particularly preferred.
  • the upper limit when blending the component (B) in the cosmetic is not particularly limited as long as the effect is exhibited, but is preferably 20% by weight. 18% by weight is more preferred, 16% by weight is still more preferred, 12% by weight is even more preferred, 10% by weight is even more preferred, and 5% by weight is particularly preferred.
  • (A) / (B) 1/20 to 100,000 / 1 (g / G), preferably 1/10 to 10000/1 (g / g), more preferably 1/2 to 5000/1 (g / g), and even more preferably 3/1 to 5000/1 (g / g).
  • the above ratio is calculated based on the weight of the cysteine derivative portion (free body).
  • the form of the cosmetic of the present invention is not particularly limited, and can take any form such as liquid, paste, gel, solid, and powder.
  • oil components for example, oil components, surfactants, amino acid derivatives, lower alcohols, higher alcohols, polyhydric alcohols, sugar alcohols and alkylene oxide adducts thereof, water-soluble polymers, gelling agents, whitening agents, bactericides and antibacterial agents, Anti-inflammatory agent, analgesic agent, antifungal agent, keratin softening release agent, skin colorant, hormone agent, UV absorber, hair restorer, antiperspirant and astringent active ingredient, sweat deodorant, vasodilator, herbal medicine, pH adjustment Agents, sequestering agents, viscosity modifiers, pearlizing agents, natural fragrances, synthetic fragrances, dyes, pigments, preservatives, emulsifiers, fats and waxes, silicone compounds, perfume oils and the like.
  • N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid N-acetyl-cysteinylpyruvic acid; hereinafter sometimes abbreviated as N-Ac-CP
  • N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester obtained by the same procedure as in Synthesis Example 1 was dissolved in a mixed solvent of methanol (120 ml) and water (120 ml), and 2N NaOH was added. (182.4 ml) was added. The reaction was heated with stirring at 100 ° C. for 4 hours and at 80 ° C. overnight under an argon atmosphere. After allowing the reaction solution to cool to room temperature, AMBERLITE IR120B H AG (about 250 g) was added to adjust the pH of the solution to 1 to 2.
  • the medium was collected, and the amount of water-soluble collagen in the medium was quantified by ELISA.
  • ELISA TAKARA, Procollagen Type I-C-peptide (PIP) EIA Kit was used.
  • the calculated value of the control was defined as 100%
  • the calculated value 3 days after the addition of each sample at a predetermined concentration was defined as relative%
  • the water-soluble collagen production rate of each sample was calculated.
  • a sample containing 0.1% dimethyl sulfoxide dissolved and added in dimethyl sulfoxide was used as a control (no sample added).
  • the microplate reader used in this collagen production rate measurement test is MULTISKAN FC, manufactured by Thermo Fisher Scientific.
  • Collagen production rate is 130% or more.
  • ⁇ Collagen production rate is 120% or more and less than 130%.
  • ⁇ Collagen production rate is 110% or more and less than 120%.
  • ⁇ Collagen production rate is 100% or more and less than 110%.
  • X Collagen production rate is less than 100%.
  • XX Theoretical value-actual measured value is 10% or more.
  • ⁇ : Theoretical value-measured value is 5% or more and less than 10%.
  • ⁇ : Theoretical value-measured value is 0% or more and less than 5%.
  • ⁇ : Theoretical value-actual value is -5% or more and less than 0%.
  • ⁇ : Theoretical value-actual value is less than -5%.
  • the cosmetics of the present invention will be exemplified. All of these cosmetics have high stability and safety, and are excellent in the effect of preventing wrinkles or imparting firmness and firmness to hair.
  • BG 1,3-butylene glycol
  • PG propylene glycol
  • DPG dipropylene glycol
  • PEG polyethylene glycol
  • the cysteine derivative of the present invention or a salt thereof has high stability and safety and has an excellent anti-wrinkle effect. As a result, it has become possible to provide a cosmetic that is more effective than conventional wrinkle-preventing cosmetics and is less likely to cause skin problems.
  • the collagen production promoter of the present invention promotes collagen production and is effective, for example, for preventing wrinkles and preventing and treating wrinkles.

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  • Toxicology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne un produit cosmétique très stable et totalement inoffensif, caractérisé par un remarquable effet antirides. L'invention concerne, en outre, un agent favorisant de façon particulièrement efficace la production de collagène. Ce produit cosmétique antirides, ou cet agent favorisant la production de collagène, contient un dérivé de cystéine représenté par la formule générale (I), ou un sel de celui-ci [Dans la formule, X et Y représentent indépendamment l'un de l'autre OR1 ou NHR2 (Dans ces formules, R1 et R2 représentent indépendamment l'un de l'autre un atome d'hydrogène ou un groupe alkyle en C1 à C22) ; Z représente un atome d'hydrogène ou un groupe alkyle en C1 à C22 ; et W représente un groupe alkyle en C1 à C22, un groupe alcoxy en C1 à C22 ou un groupe alkylamino en C1 à C22).
PCT/JP2012/081191 2011-11-30 2012-11-30 Produit cosmétique antirides WO2013081146A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2013081192A1 (ja) * 2011-11-30 2015-04-27 味の素株式会社 システイン誘導体および界面活性剤を含有する化粧料
JPWO2013081193A1 (ja) * 2011-11-30 2015-04-27 味の素株式会社 システイン誘導体およびアルコールを含有する化粧料
JPWO2016024599A1 (ja) * 2014-08-11 2017-06-01 サンスター株式会社 毛髪組成物
JP2018188427A (ja) * 2017-04-27 2018-11-29 ライオン株式会社 口腔用組成物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009227660A (ja) * 2008-02-28 2009-10-08 Ajinomoto Co Inc システイン誘導体
JP2010001239A (ja) * 2008-06-19 2010-01-07 Nippon Rikagaku Yakuhin Kk 外用組成物
WO2011149093A1 (fr) * 2010-05-28 2011-12-01 味の素株式会社 Dérivé de cystéine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB811816A (en) * 1954-07-16 1959-04-15 Farmaceutici Italia Heterocyclic hydrazides
FR2816838B1 (fr) * 2000-11-17 2004-12-03 Oreal Utilisation de derives de l'acide 2-oxothiazolidine- 4-carboxylique comme agents prodesquamants

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009227660A (ja) * 2008-02-28 2009-10-08 Ajinomoto Co Inc システイン誘導体
JP2010001239A (ja) * 2008-06-19 2010-01-07 Nippon Rikagaku Yakuhin Kk 外用組成物
WO2011149093A1 (fr) * 2010-05-28 2011-12-01 味の素株式会社 Dérivé de cystéine

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
G. CREMONESI ET AL.: "Asymmetric synthesis of 1,3-thiazolidine-derived spiro-p-lactams via a Staudinger reaction between chiral ketenes and imines", TETRAHEDRON:ASYMMETRY, vol. 16, 2005, pages 3371 - 3379 *
J. P. NALLET ET AL.: "Synthesis of a Series of Hexitol and Aminodeoxyhexitol Mononitrate Derivatives Containing a Sulfur Group and Pharmacological Evaluation on Isolated Rat Aortas", EUR. J. ORG. CHEM., 1998, pages 933 - 943 *
MAXWELL.P.S.: "Reactions of Semimercaptals With Amino Compounds", J. BIOLOGICAL CHEM., vol. 121, 1937, pages 539 - 548 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2013081192A1 (ja) * 2011-11-30 2015-04-27 味の素株式会社 システイン誘導体および界面活性剤を含有する化粧料
JPWO2013081193A1 (ja) * 2011-11-30 2015-04-27 味の素株式会社 システイン誘導体およびアルコールを含有する化粧料
JPWO2016024599A1 (ja) * 2014-08-11 2017-06-01 サンスター株式会社 毛髪組成物
JP2018188427A (ja) * 2017-04-27 2018-11-29 ライオン株式会社 口腔用組成物
JP7064938B2 (ja) 2017-04-27 2022-05-11 ライオン株式会社 口腔用組成物

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