WO2017094852A1 - Composition pour application externe - Google Patents

Composition pour application externe Download PDF

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Publication number
WO2017094852A1
WO2017094852A1 PCT/JP2016/085762 JP2016085762W WO2017094852A1 WO 2017094852 A1 WO2017094852 A1 WO 2017094852A1 JP 2016085762 W JP2016085762 W JP 2016085762W WO 2017094852 A1 WO2017094852 A1 WO 2017094852A1
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Prior art keywords
composition
acid
component
skin
group
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PCT/JP2016/085762
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English (en)
Japanese (ja)
Inventor
奈々 原矢
博治 石井
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味の素株式会社
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Publication of WO2017094852A1 publication Critical patent/WO2017094852A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—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
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • 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
    • A61K8/67—Vitamins
    • 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

Definitions

  • the present invention is selected from the group consisting of (A) a specific acylproline or a salt thereof, and (B) an amino acid and a derivative thereof (excluding the above (A)), a vitamin and a derivative thereof, and a vitamin-like substance. It is related with the composition which contains at least 1 sort (s) and is excellent in skin permeability.
  • Amino acids, vitamins, vitamin-like substances, etc. are widely used in skin drugs, quasi-drugs, cosmetics, etc., but these are difficult to penetrate the stratum corneum (ie, difficult to penetrate the skin), so the effect Therefore, various studies have been made on methods for promoting the penetration of amino acids into the skin.
  • Patent Document 1 it has been reported that diisopropyl adipate can promote the penetration of taurine into the skin.
  • the compound when the compound is incorporated in an actual formulation system, the skin permeation promoting effect may not be exhibited, and the effect is not satisfactory.
  • many other materials that can promote skin permeation have been reported. For example, organic acids such as lactic acid have been reported (Patent Document 2).
  • acylproline decanoyl proline can be used as a moisturizer (Patent Document 3), dodecanoyl proline can be used as a slimming agent and solubilizer (Patent Documents 4 and 5), cocoylproline can be used as a fragrance, It has been reported that it can be used as a solubilizer of essential oil (Patent Document 6). However, it has not been reported so far that acylproline has an effect of promoting skin penetration.
  • the present invention has been made in view of the above circumstances, and the problem to be solved is an amino acid and a derivative thereof, a vitamin and a derivative thereof, and a composition excellent in the permeability of a vitamin-like substance to the skin,
  • an object is to provide a composition capable of exerting or improving the effects and activities of amino acids and derivatives thereof, vitamins and derivatives thereof, and vitamin-like substances by being excellent in permeability to the skin.
  • the present inventors have found that a specific acylproline can promote penetration of amino acids and derivatives thereof, vitamins and derivatives thereof, and vitamin-like substances into the skin. It was.
  • the present inventors surprisingly made a specific acylproline coexist with at least one selected from the group consisting of amino acids and derivatives thereof, vitamins and derivatives thereof, and vitamin-like substances, It has been found that the low temperature stability of acylproline can be improved.
  • the inventors of the present invention have completed the present invention by further research based on these findings. That is, the present invention is as follows.
  • acyl group represented by R 1 —CO— represents an acyl group derived from a fatty acid having 2 to 23 carbon atoms
  • B an amino acid and a derivative thereof
  • (B) is an amino acid, taurine, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester, N-acetylcysteine, alanylglutamine, glycylglycine, glutamyllysine, pyriyl [1] or [2] which is at least one selected from the group consisting of doxylserine, niacinamide, panthenol, pantothenyl ethyl ether, ascorbic acid, L-ascorbic acid 2-glucoside, inositol, carnosine and ectoine The composition as described.
  • any of [1] to [6] wherein the weight ratio (A: B) of the content of (A) to the content of (B) in the composition is 1: 0.002 to 2000 A composition according to any one of the above.
  • acyl group represented by R 1 —CO— represents an acyl group derived from a fatty acid having 2 to 23 carbon atoms.
  • (B) Promote at least one skin permeation selected from the group consisting of amino acids and derivatives thereof (excluding (A) above), vitamins and derivatives thereof, and vitamin-like substances, [12 ] The skin penetration enhancer of description.
  • (B) is an amino acid, taurine, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester, N-acetylcysteine, alanylglutamine, glycylglycine, glutamyllysine, pyriyl [13] or [14], which is at least one selected from the group consisting of doxylserine, niacinamide, panthenol, pantothenyl ethyl ether, ascorbic acid, L-ascorbic acid 2-glucoside, inositol, carnosine and ectoine The skin penetration enhancer described.
  • (B) is an amino acid, taurine, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester, N-acetylcysteine, alanylglutamine, glycylglycine, glutamyllysine, pyriyl [16] or [17], which is at least one selected from the group consisting of doxylserine, niacinamide, panthenol, pantothenyl ethyl ether, ascorbic acid, L-ascorbic acid 2-glucoside, inositol, carnosine and ectoine Use of description.
  • the composition excellent in the permeability to the skin of an amino acid and its derivative (s), a vitamin and its derivative (s), and a vitamin-like substance is provided.
  • the composition of the present invention can exert or improve the effects and activities thereof by being excellent in the penetration of amino acids and derivatives thereof, vitamins and derivatives thereof, and vitamin-like substances into the skin.
  • a skin penetration enhancer preferably an amino acid and a derivative thereof, a vitamin and a derivative thereof, and a skin penetration enhancer of a vitamin-like substance
  • composition of the present invention comprises (A) an acylproline represented by the general formula (I) or a salt thereof
  • acyl group represented by R 1 —CO— represents an acyl group derived from a fatty acid having 2 to 23 carbon atoms
  • B an amino acid and a derivative thereof (provided that (A) And at least one selected from the group consisting of vitamins and derivatives thereof, and vitamin-like substances.
  • Component (A) of the present invention is an acylproline represented by the general formula (I) or a salt thereof.
  • an acyl group represented by R 1 —CO— represents an acyl group derived from a fatty acid having 2 to 23 carbon atoms
  • R 1 —CO— is an acyl group derived from a fatty acid having 2 to 23 carbon atoms, that is, an acyl residue of the fatty acid.
  • Examples thereof include an acetyl group, an isopropanoyl group, Propanoyl, butanoyl, isobutanoyl, sec-butanoyl, tert-butanoyl, pentanoyl, sec-pentanoyl, tert-pentanoyl, isopentanoyl, hexanoyl, heptanoyl, octanoyl, 2-ethylhexa
  • Examples include noyl group, tert-octanoyl group, nonanoyl group, isononanoyl group, decanoyl group, isodecanoyl group, undecanoyl group, lauroyl group, undecylenoyl group, myristoyl group, palmitoyl group, stearoyl group, behenoyl group and oleoyl group.
  • the long-chain acyl group represented by R 1 —CO— is an acyl group derived from an acid having a single composition, as well as a natural mixture such as coconut oil fatty acid, castor oil fatty acid, olive oil fatty acid, and palm oil fatty acid. It may be an acyl group derived from a fatty acid or a fatty acid obtained by synthesis (including a branched fatty acid). One of these may be used, or two or more selected from the above group may be mixed and used.
  • the acyl group represented by R 1 —CO— represents an acyl group derived from a fatty acid having 2 to 23 carbon atoms, and the number of carbon atoms of the fatty acid is preferably 4 or more, more preferably 6 or more. More preferably, it is 8 or more, particularly preferably 10 or more.
  • the number of carbon atoms of the fatty acid is preferably 20 or less, more preferably 18 or less, and particularly preferably 14 or less.
  • the acyl group represented by R 1 —CO— is preferably an acyl group derived from a fatty acid having 4 to 18 carbon atoms, and is an acyl group derived from a fatty acid having 6 to 16 carbon atoms. Is more preferably an acyl group derived from a fatty acid having 8 to 14 carbon atoms, particularly preferably an acyl group derived from a fatty acid having 10 to 14 carbon atoms, and a decanoyl group or myristoyl group. The group is most preferred.
  • fatty acids may be saturated or unsaturated, that is, the acyl group represented by R 1 —CO— is either an acyl group derived from a saturated fatty acid or an acyl group derived from an unsaturated fatty acid. However, it is preferably an acyl group derived from a saturated fatty acid. Accordingly, R 1 represents a hydrocarbon group having 1 to 22 carbon atoms. As the “hydrocarbon group” for R 1 , a chain hydrocarbon group (for example, an alkyl group and an alkynyl group) is preferable, and any linear or branched one can be used.
  • R 1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1,2-dimethylpropyl, -Ethylpropyl group, hexyl group, isohexyl group, 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, octyl group, nonyl group, decyl Group, undecyl group, tridecyl group, tetradecyl group, pentadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group, eicosyl group, henicosyl group, heneicosyl
  • the number of carbon atoms of R 1 is preferably 3 or more, more preferably 5 or more, further preferably 7 or more, particularly preferably 9 or more, and the number of carbon atoms is preferably 19 or less. More preferably, it is 17 or less, More preferably, it is 15 or less.
  • the number of carbon atoms of R 1 is preferably 3 to 17, more preferably 5 to 15, further preferably 7 to 13, and particularly preferably 9 to 13.
  • Examples of the salt of acylproline represented by the general formula (I) include pharmacologically acceptable salts, such as alkali metal salts such as lithium salts, sodium salts, potassium salts; calcium salts, magnesium salts, etc. Examples include alkaline earth metal salts; ammonium salts; and basic organic salts. Of these, from the viewpoint of solubility, sodium salts, potassium salts, and ammonium salts are preferable, sodium salts and potassium salts are more preferable, and sodium salts are still more preferable.
  • acylproline represented by the general formula (I) may be any of hydrate, non-hydrate, solvate and solvate.
  • the production method of component (A) is not particularly limited, and can be easily produced by combining known methods. Specifically, proline and acid chloride can be produced by the Schotten-Baumann method by simultaneously dropping acid chloride and a base such as sodium hydroxide.
  • the proline used for the production of the component (A) may be any of L-form, D-form and a mixture thereof, preferably L-form.
  • composition of the present invention may contain at least one acylproline represented by the general formula (I) or a salt thereof as the component (A), but is represented by two or more general formulas (I).
  • An acylproline or a salt thereof may be contained.
  • the content of the component (A) in the composition of the present invention is usually 0.001% by weight or more with respect to the total amount of the composition of the present invention, from the viewpoint of the touch at the time of application, particularly the permeation into the skin, Preferably it is 0.005 weight% or more, More preferably, it is 0.01 weight% or more, Most preferably, it is 0.02 weight% or more. Further, the content is usually 5% by weight or less with respect to the total amount of the composition of the present invention, and preferably 2% by weight or less, more preferably 1.5% or less, from the viewpoint of further suppressing generation of a specific odor. % By weight or less, particularly preferably 1% by weight or less.
  • Component (B) of the present invention is at least one selected from the group consisting of amino acids and derivatives thereof (excluding component (A)), vitamins and derivatives thereof, and vitamin-like substances.
  • amino acid refers to an organic compound having both an amino group and a carboxy group in the molecule, and is a concept including both amino acids constituting a protein and amino acids not constituting a protein.
  • amino acids constituting proteins include aliphatic amino acids (glycine, alanine), branched chain amino acids (valine, leucine, isoleucine), hydroxy amino acids (serine, threonine), sulfur-containing amino acids (cysteine, methionine), amide type Neutral amino acids such as amino acids (asparagine, glutamine), imino acids (proline), aromatic amino acids (phenylalanine, tyrosine, tryptophan); acidic amino acids such as aspartic acid and glutamic acid; and basic amino acids such as lysine, arginine and histidine It is done.
  • amino acids that do not constitute a protein include tranexamic acid, 3,4-dihydroxyphenylalanine, theanine, ⁇ -aminobutyric acid, ⁇ -alanine, sarcosine, citrulline, ornithine, and ⁇ -aminocaproic acid.
  • amino acid any of L-form, D-form and DL-form can be used, preferably L-form and DL-form, and more preferably L-form.
  • an “amino acid derivative” means a compound in which a part of an amino acid is modified (eg, acetylation, esterification, etc.) or a compound in which a part of an amino acid is bound to another compound. It is a concept that includes dipeptides, tripeptides, oligopeptides, and the like in which amino acids are linked by peptide bonds.
  • amino acid derivatives include N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester, N-acetylcysteine, alanylglutamine, glycylglycine, glutamyllysine, carnosine, ectoine, Anserine, alanyl ornithine, glycyltyrosine, valylglycine, lysylornithine, ornitylthreonine, threonylornithine, prolylhistamine, sodium pyrrolidonecarboxylate (PCA-Na), PCA (pyrrolidonecarboxylic acid) arginine, PCA lysine, PCA Histidine, PCA carnitine, taurine, thiotaurine, hypotaurine, pyridoxylserine, phosphoserine, glutathione, ⁇ -amino- ⁇
  • vitamins examples include fat-soluble vitamins such as vitamin A, vitamin D, vitamin E, and vitamin K; and vitamin B 1 , vitamin B 2 , vitamin B 6 , vitamin B 12 , ascorbic acid (vitamin C), folic acid, Examples thereof include water-soluble vitamins such as nicotinic acid, niacinamide, pantothenic acid, and biotin.
  • the “vitamin derivative” refers to a compound in which a part of the vitamin is modified or a compound in which a part of the vitamin is bound to another compound.
  • Specific examples thereof include L-ascorbic acid 2-glucoside ( AA-2G), panthenol, pantothenyl ethyl ether, hydroquinone and the like.
  • vitamin-like substance refers to a compound having a physiological action similar to that of a vitamin, which can be biosynthesized in the body unlike vitamins. Specific examples thereof include inositol, choline, ⁇ Examples include lipoic acid, ubiquinone, pangamic acid, carnitine and the like.
  • Amino acids and derivatives thereof, vitamins and derivatives thereof, and vitamin-like substances may all be in the form of salts.
  • “amino acids and derivatives thereof, vitamins and derivatives thereof, and vitamin-like substances” It is a concept including the salt.
  • the salt is preferably a physiologically acceptable salt, and examples thereof include a salt with an inorganic base, a salt with an inorganic acid, and a salt with an organic acid.
  • the salt with an inorganic base include a salt with an alkali metal such as sodium, potassium and lithium, a salt with an alkaline earth metal such as calcium and magnesium, and an ammonium salt.
  • Examples of the salt with an inorganic acid include salts with hydrohalic acid (hydrochloric acid, hydrobromic acid, hydroiodic acid, etc.), sulfuric acid, nitric acid, phosphoric acid and the like.
  • Examples of the salt with an organic acid include salts with formic acid, acetic acid, propionic acid, oxalic acid, succinic acid, maleic acid, fumaric acid, citric acid and the like.
  • Component (B) may be any of those extracted and purified from naturally occurring animals and plants, or those obtained by chemical synthesis, fermentation, enzyme, or genetic recombination. Commercial products may also be used.
  • the component (B) preferably has a skin permeability coefficient of 3 ⁇ 10 ⁇ 6 cm / s or less, more preferably 8 ⁇ 10 ⁇ 7 cm / s or less, in that the effect of the present invention is more remarkably exhibited. More preferred are those having a density of 8 ⁇ 10 ⁇ 8 cm / s or less, and most preferred are those having a density of 3 ⁇ 10 ⁇ 8 cm / s or less. The lower the skin permeability coefficient, the less likely it is to penetrate the skin, and it is measured by a permeability test using Franz cells.
  • Component (B) has at least one action selected from the group consisting of a moisturizing action, whitening action, anti-aging action, cell activation action, anti-glycation action, antioxidant action, anti-inflammatory action, hair growth action, and blood circulation promoting action. It is preferable to have it.
  • Component (B) is preferably an amino acid, taurine, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester, N-acetylcysteine, alanylglutamine, from the viewpoint of action or versatility.
  • Glycylglycine glutamyllysine, pyridoxylserine, niacinamide, panthenol, pantothenyl ethyl ether, ascorbic acid, L-ascorbic acid 2-glucoside, inositol, carnosine, ectoine, more preferably tyrosine, arginine, histidine, Lysine, valine, tryptophan, threonine, serine, glutamine, aspartic acid, glutamic acid, glycine, alanine, leucine, isoleucine, cysteine, methionine, taurine, tranexamic acid, 3,4-dihydroxyfe Lualanine, N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester, N-acetylcysteine, alanylglutamine, glycylglycine, glutamylly
  • composition of the present invention may contain the above component (B) singly or in combination of two or more, but preferably contains two or more.
  • the content of the component (B) in the composition of the present invention is usually 0.001% by weight or more with respect to the total amount of the composition of the present invention, and preferably 0.01% by weight or more from the viewpoint of effects. More preferably, it is 0.1% by weight or more, and particularly preferably 0.3% by weight or more.
  • the content is usually 10% by weight or less with respect to the total amount of the composition of the present invention, preferably 7% by weight or less, more preferably 5.5% by weight or less from the viewpoint of stability. Particularly preferably, it is 5% by weight or less.
  • the “content of component (B)” means the content of one component (B) when the component (B) contained in the composition of the present invention is only one. This means that when there are two or more components (B) contained in the composition of the present invention, it means the total content of all the components (B) contained.
  • the weight ratio (A: B) of the content of the component (A) and the content of the component (B) in the composition of the present invention is preferably from the viewpoint that the effects of the present invention are efficiently exhibited. Is 1: 0.002 to 2000, more preferably 1: 0.02 to 1000, still more preferably 1: 0.1 to 500, and particularly preferably 1: 0.5 to 100.
  • composition of the present invention may contain (C) a polyhydric alcohol in addition to the components (A) and (B) from the viewpoints of feel and stability after application and after application.
  • polyhydric alcohol examples include glycerin, ethylene glycol, 1,3-butylene glycol, 1,3-propanediol, propylene glycol, isoprene glycol, dipropylene glycol, 1,2-hexanediol, 1,2-octanediol. And sorbitol. From the viewpoints of environmental consideration and moist feeling, glycerin, 1,3-butylene glycol, 1,3-propanediol, dipropylene glycol, 1,2-hexanediol, 1,2-octanediol, and sorbitol are preferable.
  • the content of the component (C) in the composition of the present invention is usually 0.1% by weight or more with respect to the total amount of the composition of the present invention, and preferably 0.3% by weight from the viewpoint of feel during application. Or more, more preferably 0.5% by weight or more, and particularly preferably 1% by weight or more.
  • the content is usually 20% by weight or less, and is preferably 15% by weight or less, more preferably 10% by weight or less, and particularly preferably 7% by weight or less from the viewpoint of feel during coating.
  • composition of the present invention may contain (D) a water-soluble polymer in addition to the above components (A) and (B) from the viewpoint of feel during application and after application.
  • the water-soluble polymer may be a synthetic polymer, but is preferably obtained from a natural product.
  • Specific examples of water-soluble polymers include guar gum, locust bin gum, quince seed, carrageenan, galactan, gum arabic, tragacanth gum, pectin, mannan, starch, xanthan gum, dextran, succinoglucan, curdlan, hyaluronic acid, sodium hyaluronate , Gelatin, casein, albumin, collagen, methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, methyl hydroxypropyl cellulose, soluble starch, carboxymethyl starch, methyl starch, propylene glycol alginate, alginate, polyvinyl alcohol, polyvinyl pyrrolidone, polyvinyl methyl Ether, carboxyvinyl polymer, sodium polyacrylate, Li oxide, ethylene oxide-propylene oxide copo
  • the content of the component (D) in the composition of the present invention is usually 0.001% by weight or more with respect to the total amount of the composition of the present invention, and preferably 0.01% by weight from the viewpoint of feel during application. Or more, more preferably 0.05% by weight or more, particularly preferably 0.07% by weight or more, and most preferably 0.1% by weight or more.
  • the content is usually 5% by weight or less, and preferably 2% by weight or less, more preferably 1.5% by weight or less, and particularly preferably 1% by weight or less, from the viewpoint of feel during application. Yes, and most preferably 0.7% by weight or less.
  • composition of the present invention is not particularly limited, and examples thereof include liquid, emulsion, paste, gel, solid, and powder.
  • the pH of the composition of the present invention is usually 3.5 to 8.5, and preferably 4 to 8 from the viewpoint of irritation and stability of the component (A) in the composition.
  • the method for producing the composition of the present invention is not particularly limited, and can be produced by a method commonly used in the cosmetics field or the pharmaceutical field or a method analogous thereto.
  • composition of the present invention can be blended in cosmetics or medicines (including quasi drugs), or the composition of the present invention itself can be used as a cosmetic or medicine (including quasi drugs). Also good.
  • the cosmetics include face wash, lotion, emulsion, cream, gel, Skin cosmetics such as serums, packs, masks, etc .; makeup cosmetics such as white powder, foundation, lipstick, teak, eyeliner, mascara, eye shadow, eyebrows; shampoo, rinse, hair conditioner, hair styling agent, hair treatment, Examples include hair cosmetics such as hair mist.
  • the cosmetics may have the effects of the present invention by adding ingredients that may be added to cosmetics. You may mix
  • Specific examples of the components include oil agents, chelating agents, surfactants, powders, sugar alcohols and alkylene oxide adducts thereof, lower alcohols, animal and plant extracts, nucleic acids, enzymes, anti-inflammatory agents, fungicides, preservatives, Antioxidants, ultraviolet absorbers, antiperspirants, pigments, dyes, oxidation dyes, organic and inorganic powders, pH adjusters, pearling agents, wetting agents and the like can be mentioned.
  • oil agent examples include higher alcohols such as cetyl alcohol, isostearyl alcohol, lauryl alcohol, hexadecyl alcohol and octyldodecanol; fatty acids such as isostearic acid, undecylenic acid and oleic acid; myristyl myristate, hexyl laurate and oleic acid Decyl, isopropyl myristate, hexyl decyl dimethyloctanoate, glyceryl monostearate, diethyl phthalate, ethylene glycol monostearate, octyl oxystearate, alkyl benzoate, dilauroyl glutamate (phytosteryl / octyldodecyl), cetyl octoate Esters such as liquid paraffin, polyisobutene, petrolatum, squalane and other hydrocarbons; lanolin, reduced lanolin, carn
  • silicone oils include methylpolysiloxane, highly polymerized methylpolysiloxane, polyoxyethylene / methylpolysiloxane copolymer, polyoxypropylene / methylpolysiloxane copolymer, and poly (oxyethylene, oxypropylene) / methyl.
  • Ether-modified silicone such as polysiloxane copolymer, stearoxymethylpolysiloxane, stearoxytrimethylsilane, methylhydrogenpolysiloxane, decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane, tetrahydrotetramethylcyclotetrasiloxane, methylcyclopoly Cyclic silicones such as siloxane and dodecamethylcyclohexasiloxane; methylphenylpolysiloxane, trimethylsiloxysilicic acid, aminoethylaminopropyl Amino-modified silicone such as siloxane / dimethylsiloxane copolymer, silanol-modified polysiloxane, alkoxy-modified polysiloxane, fatty acid-modified polysiloxane, fluorine-modified polysiloxane, epoxy-modified polys
  • the chelating agent is not particularly limited, but preferably triethylenetetramine, 2-thenoyltrifluoroacetone, thioglycolic acid, tartaric acid, succinic acid, 8-quinolinol, pyridine-2,6-dicarboxylic acid, pyridine, 1, 10-tenanthroline, lactic acid, 8-hydroxyquinoline-5-sulfonic acid, glycine, 2,2'-pyridylethylenediamine, aurintricarboxylic acid, xylenol orange, 5-sulfosalicylic acid, salicylic acid, pyrocatechol-3,5-disulfonate 4,5-dihydroxybenzene-1,3-disulfonic acid, 1,2-diaminocyclohexane-N, N, N ′, N′-tetraacetic acid, citric acid, oxalate, nitrilotriacetic acid, ethylenediamine-N, N
  • the surfactant examples include N-long chain acyl amino acid salts such as N-long chain acyl acidic amino acid salts and N-long chain acyl neutral amino acid salts, N-long chain fatty acid acyl-N-methyl taurine salts, alkyls.
  • Anionic surfactants such as sulfates and their alkylene oxide adducts, fatty acid amide ether sulfates, fatty acid metal salts and weak base salts, sulfosuccinic acid surfactants, alkyl phosphates and their alkylene oxide adducts, alkyl ether carboxylic acids; Ether type surfactants such as glycerin ether and its alkylene oxide adduct, polyoxyethylene polyoxypropylene alkyl ether, ester type surfactants such as glycerin ester and its alkylene oxide adduct, sorbitan ester and its alkylene oxy Ether ester type surfactants such as alkyl adducts, polyoxyalkylene fatty acid esters, glycerin esters, fatty acid polyglycerin esters, sorbitan esters, sucrose fatty acid esters, polyoxyalkylene hydrogenated castor oil and other ester type surfactants
  • the powder examples include resin powders such as nylon beads and silicone beads, nylon powder, metal fatty acid soap, yellow iron oxide, red iron oxide, black iron oxide, chromium oxide, cobalt oxide, carbon black, ultramarine, bitumen, Zinc oxide, titanium oxide, zirconium oxide, silicon oxide, aluminum oxide, cerium oxide, titanium mica, boron nitride, barium sulfate, calcium carbonate, magnesium carbonate, aluminum silicate, magnesium silicate, silicon carbide, dye, lake, sericite, mica , Talc, kaolin, plate-like barium sulfate, butterfly-like barium sulfate, fine particle titanium oxide, fine particle zinc oxide, fine particle iron oxide, acyl lysine, acyl glutamic acid, acyl arginine, acyl glycine, and the like, and further silicone treatment, Fluorine compound Management, silane coupling agent treatment, silane treatment organic titanate process, acylated lysine treatment, fatty acid treatment, metal
  • sugar alcohol and its alkylene oxide adduct examples include mannitol.
  • lower alcohols examples include ethanol and propanol.
  • composition of the present invention When the composition of the present invention is blended with a medicine (including quasi-drug) or when the composition itself of the present invention is a medicine (including quasi-drug),
  • a medicine including quasi-drug
  • coating agents such as ointments (aqueous ointments, oily ointments, etc.), creams, solutions, emulsions, gels, lotions, liniments, pasta, etc .; poultices, plasters, tapes, patches And the like; sprays such as aerosols and sprays; suppositories and the like.
  • the medicine includes pharmacological In the range which does not inhibit the effect of this invention, you may mix
  • composition of the present invention is preferably for the skin, and is preferably blended with skin cosmetics or dermatological drugs (including quasi-drugs for skin), or the composition of the present invention itself is used for skin cosmetics or It is preferable to use a skin drug (including quasi-drugs for skin).
  • skin is a concept including not only the epidermis of the body (eg, face, head, neck, chest, abdomen, waist, back, buttocks, arms, legs, hands, etc.) but also the mucous membrane.
  • Examples of the application target of the composition of the present invention include mammals (eg, humans, mice, rats, hamsters, rabbits, cats, dogs, cows, sheep, monkeys, etc.), but are not limited thereto. Not a thing.
  • the dose of the composition of the present invention and the number of times of application to the subject can be appropriately adjusted according to the type of the component (B), the form of the composition, the subject to be applied, and the like.
  • composition of the present invention may be stored at a low temperature (usually ⁇ 5 to 10 ° C.) because of its excellent low-temperature stability as shown in the examples described later.
  • the present invention also provides a skin penetration enhancer containing component (A).
  • the component (A) contained in the skin penetration enhancer of the present invention is the same as the component (A) contained in the composition of the present invention, and the preferred embodiment thereof is also the same.
  • the form of the skin penetration enhancer of the present invention is not particularly limited, and examples thereof include liquid, emulsion, paste, gel, solid, and powder.
  • the skin penetration enhancer of the present invention may be the component (A) itself, or the component (A) is formulated using, for example, an excipient, a formulation agent, a solubilizing agent, a suspending agent, etc. It may be obtained by converting.
  • the content of the component (A) in the skin penetration enhancer of the present invention is usually 0.01 to 100% by weight, preferably 0.1 to 99.9% by weight based on the total amount of the skin penetration enhancer of the present invention. %, More preferably 1 to 99% by weight.
  • the method for producing the skin penetration enhancer of the present invention is not particularly limited, and can be produced by a method commonly used in the field of pharmaceutical technology.
  • the skin penetration enhancer of the present invention is preferably used to promote skin penetration of component (B).
  • component (B) whose penetration into the skin is promoted by the skin penetration enhancer of the present invention is the same as the component (B) contained in the composition of the present invention, and its preferred embodiment is also the same.
  • the skin penetration enhancer of the present invention has a weight ratio (A: B) between the amount of the component (A) used and the amount of the component (B) whose penetration into the skin is promoted by the skin penetration enhancer of the present invention.
  • 1 is preferably used in a range of 1: 0.002 to 2000, and is preferably used in a range of 1: 0.02 to 1000 from the viewpoint of stability and the effect of the present invention can be efficiently exhibited. More preferably, it is used more preferably at 1: 0.1 to 500, and particularly preferably used at 1: 0.5 to 100.
  • Triethylamine (159 ml, 1141 mmol) was added to the obtained ethyl acetate solution under argon, acetyl chloride (61 ml, 858 mmol) was slowly added dropwise, and the reaction mixture was heated to reflux for 4 hours to give N-acetyl-2-methylthiazolidine.
  • -2,4-dicarboxylic acid-2-ethyl ester was obtained (the area ratio in the HPLC chart of the product in the reaction solution was confirmed, and the ratio of trans isomer: cis isomer was about 95: 5).
  • water 300 ml was added and the pH was adjusted to 1.0 with HCl.
  • compositions of Examples 1 to 24 and Comparative Examples 1 to 22 were prepared by adjusting the pH using an aqueous sodium hydroxide solution or an aqueous hydrochloric acid solution, and finally adjusting the amount of water.
  • the unit of composition shown in Tables 1 to 7 is% by weight.
  • the skin permeability of the component (B) of the compositions of Examples 1 to 24 and Comparative Examples 1 to 22 was measured using a lateral diffusion cell (average diffusion area: 0.64 cm 2 ) and a Strat-M membrane (25 mm, Merck) as a skin model. Evaluation was performed by an in vitro permeation test using Specifically, after mounting the Strat-M membrane on a horizontal diffusion cell and fixing it, the sample composition was added to the cell on the donor side, and water was added to the cell on the receiver side, each at 37 ° C. ( ⁇ 0.2 ° C.). The sample to be analyzed was obtained by sampling a certain amount from the cell on the receiver side over time. The obtained specimen was quantitatively measured for the component (B) by a liquid chromatograph according to a conventional method to determine the cumulative permeation amount ( ⁇ g / cm 2 ) of the component (B).
  • the skin permeability of the component (B) was evaluated based on the following criterion 1.
  • N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid-2-ethyl ester (N-Ac-CP2Et) used as component (B) in Examples 22 to 24 was not used in combination with component (A)
  • the cumulative permeation amount after 8 hours from the start of the test was determined based on the corresponding composition containing no component (A) (Comparative Example 20).
  • evaluation was performed based on the following criterion 2.
  • the skin permeability of the component (B) of Example 22 was evaluated by comparing the cumulative permeation amount of the component (B) 8 hours after the start of the test with that of Comparative Example 20.
  • compositions containing components (A) and (B) (Examples 22 to 24), compositions containing component (B) and not containing component (A) (comparison) Compared with Examples 20 to 22), the skin permeation promoting action was 10 times or more.
  • compositions of Comparative Examples 23 to 27 were prepared in the same procedure as in Test Example 1.
  • lactic acid or isopropyl adipate which is generally known to have permeation promoting ability, was used as the component (A ′).
  • the unit of composition shown in Table 8 is% by weight.
  • Example 2 (Evaluation of solubility and room temperature stability) The compositions of Example 2 and Comparative Examples 23 to 27 were filled in 50 ml vials immediately after preparation and stored at room temperature for 1 month, and the dissolution conditions immediately after preparation and after storage for 1 month were evaluated according to the following criteria. did.
  • compositions of Example 25 and Comparative Example 28 Each component described in column I of Table 9 was dissolved by heating and stirring, and then the heated component (water) described in column II was added and cooled to around room temperature. Subsequently, after adding each component, the component (A) and the component (B) described in the column III, which was stirred and dissolved in advance, the pH was adjusted after finally stirring and dissolving, and finally the amount of water was adjusted. By adjusting, the compositions of Example 25 and Comparative Example 28 were prepared. The unit of composition shown in Table 9 is% by weight.
  • compositions of Examples 26 to 28 and Comparative Example 29 Compositions of Examples 26 to 28 and Comparative Example 29 were prepared in the same procedure as in Test Example 1 using the components shown in Table 11. The unit of composition shown in Table 11 is% by weight.
  • Test Example 5 (Preparation of compositions of Examples 29 and 30 and Comparative Examples 30 and 31) Among the components shown in Table 12, the components other than citric acid were stirred until they became uniform while heating at 70 ° C., cooled to near room temperature, and then adjusted to pH 5.5 with citric acid. Finally, the compositions of Examples 29 and 30 and Comparative Examples 30 and 31 were prepared by adjusting the amount of water. Each prepared composition was stored at room temperature. The unit of composition shown in Table 12 is% by weight.
  • PRODEW (registered trademark) 500” (manufactured by Ajinomoto Co., Inc.) used as component (B) is PCA-Na, sodium lactate, arginine, aspartic acid, PCA, glycine, alanine, serine, valine, proline, threonine, isoleucine, Contains histidine and phenylalanine.
  • Average point is 4.0 or more ⁇ : Average point is 3.0 or more and less than 4.0 ⁇ : Average point is 2.0 or more and less than 3.0 ⁇ : Average point is less than 2.0
  • Example 29 the composition containing the component (A) and the component (B) (Example 29) contains the component (B) and does not contain the component (A) (Comparative Example 31). It was confirmed that the penetration of the component (B) into the skin was promoted and the effects required for the component (B) (moisturizing effect, etc.) were also improved. In addition, the contact angle of Example 29 was much smaller than that of Comparative Example 31, and actually the feeling of familiarity with the skin in sensory evaluation was also very good.
  • compositions of Examples 31-42 and Comparative Examples 32-43 were prepared in the same procedure as in Test Example 1.
  • the units of composition shown in Tables 13 to 15 are% by weight.
  • Lactic acid Diisopropyl adipate manufactured by Tokyo Chemical Industry Co., Ltd .: Polyoxyethylene hydrogenated castor oil 60 manufactured by Tokyo Chemical Industry Co., Ltd. 60: NIKKOL HCO-60 (manufactured by Nikko Chemicals)
  • DPG DPG-RF (dipropylene glycol) (made by ADEKA)
  • BG 1,3-BG (1,3-butylene glycol) UK (manufactured by Daicel Chemical Industries)
  • Glycerin Concentrated glycerin for cosmetics (manufactured by Sakamoto Kogyo or Kao) Lauroyl glutamate (phytosteryl / octyldodecyl): “ELDEW” PS-203 (Ajinomoto Co., Inc.) Cetyl octanoate: CHE (manufactured by Higher Alcohol Industry)
  • a composition in which penetration of amino acids and derivatives thereof, vitamins and derivatives thereof, and vitamin-like substances into the skin is promoted is provided.
  • the composition of the present invention can exert or improve the effects and activities thereof by being excellent in the penetration of amino acids and derivatives thereof, vitamins and derivatives thereof, and vitamin-like substances into the skin.
  • a skin penetration enhancer preferably an amino acid and a derivative thereof, a vitamin and a derivative thereof, and a skin penetration enhancer of a vitamin-like substance

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Abstract

L'objectif de la présente invention est de fournir une composition qui peut présenter une excellente pénétration d'un acide aminé et un dérivé de celui-ci, une vitamine et un dérivé de celle-ci et une substance de type vitamine dans la peau. La présente invention concerne une composition caractérisée en ce qu'elle comprend (A) une acylproline spécifique et (B) au moins un composant choisi dans le groupe constitué d'un acide aminé et un dérivé de celui-ci (à l'exclusion du composant (A)), une vitamine et un dérivé de celle-ci et une substance de type vitamine.
PCT/JP2016/085762 2015-12-02 2016-12-01 Composition pour application externe WO2017094852A1 (fr)

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Publication number Priority date Publication date Assignee Title
WO1987001935A1 (fr) * 1985-10-03 1987-04-09 Rajadhyaksha Vithal J Preparation transdermique et systemique et son procede de realisation
JP2000191426A (ja) * 1998-12-22 2000-07-11 Exploit Des Prod Pour Les Ind Chim Sepc:Soc テクスチャリング剤としてのｎ―アシルアミノ酸化合物の使用法
JP2002506016A (ja) * 1998-03-09 2002-02-26 ソシエテ・デクスプロワタシオン・デ・プロデュイ・プール・レ・アンデュストリー・シミック・セピック リポアミノ酸構造を有する化合物およびスイレン抽出物を含有する相乗作用的組成物
JP2006528935A (ja) * 2003-07-25 2006-12-28 ザ プロクター アンド ギャンブル カンパニー Ｎ−アシルアミノ酸組成物を用いた哺乳類のケラチン組織の調整
JP2009512667A (ja) * 2005-10-19 2009-03-26 ソシエテ・デクスプロワタシオン・デ・プロデュイ・プール・レ・アンデュストリー・シミック・セピック ラウロイルプロリン、およびアンヒドロヘキシトールと脂肪族カルボン酸とのエステルを含む美容用および薬学的組成物。
JP2009114154A (ja) * 2007-11-09 2009-05-28 Kao Corp 化粧方法
JP2009536965A (ja) * 2006-05-15 2009-10-22 ザ プロクター アンド ギャンブル カンパニー 水溶性活性物質の浸透の増強方法
JP2011236179A (ja) * 2010-05-13 2011-11-24 Asahi Kasei Chemicals Corp 浸透促進剤
JP2012097027A (ja) * 2010-11-01 2012-05-24 Saiensurin:Kk 経皮吸収促進性皮膚外用剤
WO2013147328A1 (fr) * 2012-03-30 2013-10-03 味の素株式会社 Composition cosmétique
WO2014007290A1 (fr) * 2012-07-03 2014-01-09 味の素株式会社 Hydratant et produit cosmétique le comprenant
WO2014030746A1 (fr) * 2012-08-24 2014-02-27 味の素株式会社 Dérivé d'acyle dipeptide
WO2016039407A1 (fr) * 2014-09-10 2016-03-17 味の素株式会社 Produit hydratant et produit cosmétique contenant celui-ci

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987001935A1 (fr) * 1985-10-03 1987-04-09 Rajadhyaksha Vithal J Preparation transdermique et systemique et son procede de realisation
JP2002506016A (ja) * 1998-03-09 2002-02-26 ソシエテ・デクスプロワタシオン・デ・プロデュイ・プール・レ・アンデュストリー・シミック・セピック リポアミノ酸構造を有する化合物およびスイレン抽出物を含有する相乗作用的組成物
JP2000191426A (ja) * 1998-12-22 2000-07-11 Exploit Des Prod Pour Les Ind Chim Sepc:Soc テクスチャリング剤としてのｎ―アシルアミノ酸化合物の使用法
JP2006528935A (ja) * 2003-07-25 2006-12-28 ザ プロクター アンド ギャンブル カンパニー Ｎ−アシルアミノ酸組成物を用いた哺乳類のケラチン組織の調整
JP2009512667A (ja) * 2005-10-19 2009-03-26 ソシエテ・デクスプロワタシオン・デ・プロデュイ・プール・レ・アンデュストリー・シミック・セピック ラウロイルプロリン、およびアンヒドロヘキシトールと脂肪族カルボン酸とのエステルを含む美容用および薬学的組成物。
JP2009536965A (ja) * 2006-05-15 2009-10-22 ザ プロクター アンド ギャンブル カンパニー 水溶性活性物質の浸透の増強方法
JP2009114154A (ja) * 2007-11-09 2009-05-28 Kao Corp 化粧方法
JP2011236179A (ja) * 2010-05-13 2011-11-24 Asahi Kasei Chemicals Corp 浸透促進剤
JP2012097027A (ja) * 2010-11-01 2012-05-24 Saiensurin:Kk 経皮吸収促進性皮膚外用剤
WO2013147328A1 (fr) * 2012-03-30 2013-10-03 味の素株式会社 Composition cosmétique
WO2014007290A1 (fr) * 2012-07-03 2014-01-09 味の素株式会社 Hydratant et produit cosmétique le comprenant
WO2014030746A1 (fr) * 2012-08-24 2014-02-27 味の素株式会社 Dérivé d'acyle dipeptide
WO2016039407A1 (fr) * 2014-09-10 2016-03-17 味の素株式会社 Produit hydratant et produit cosmétique contenant celui-ci

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