WO2010024204A1 - Agent de diminution de ride - Google Patents

Agent de diminution de ride Download PDF

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Publication number
WO2010024204A1
WO2010024204A1 PCT/JP2009/064666 JP2009064666W WO2010024204A1 WO 2010024204 A1 WO2010024204 A1 WO 2010024204A1 JP 2009064666 W JP2009064666 W JP 2009064666W WO 2010024204 A1 WO2010024204 A1 WO 2010024204A1
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WO
WIPO (PCT)
Prior art keywords
pro
wrinkle
present
group
val
Prior art date
Application number
PCT/JP2009/064666
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English (en)
Japanese (ja)
Inventor
誠 常長
祐輔 原
和毅 木暮
Original Assignee
株式会社資生堂
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社資生堂 filed Critical 株式会社資生堂
Publication of WO2010024204A1 publication Critical patent/WO2010024204A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/92—Oral administration

Definitions

  • the present invention relates to a safe wrinkle preventing / improving agent having an effect of suppressing wrinkle generation and improving wrinkles. More particularly, the present invention relates to a wrinkle prevention / improving agent having a wrinkle prevention / improvement effect to prevent / improve wrinkles due to aging or photoaging.
  • compositions intended to resist skin aging such as wrinkles are conventionally known.
  • Val-Pro-Pro, Ile-Pro-Pro, and salts thereof according to the present invention are known substances, and are used for hair restoration / hair growth agents (Patent Document 1), for dullness prevention / treatment agents (Patent Document 2). ), And Val-Pro-Pro is known for its anti-stress effect and use as a functional food (Patent Document 4).
  • Patent Document 1 hair restoration / hair growth agents
  • Patent Document 2 for dullness prevention / treatment agents
  • Val-Pro-Pro is known for its anti-stress effect and use as a functional food
  • it is novel to have the wrinkle improving effect of the present invention.
  • the copper complex of Ala-His-Lys is known as a use for treating excess dye (Patent Document 3), it is novel to have the effect of the present invention.
  • JP 2002-284647 A JP 2002-284668 A JP 2005-511650 A Japanese Patent Application Laid-Open No. 11-100348
  • the present invention has been made in view of the above circumstances, and its purpose is to provide a safe wrinkle prevention / improving agent having an excellent wrinkle prevention / improvement effect such as prevention / improvement of wrinkles due to aging or photoaging. It is in.
  • Val-Pro-Pro As a result of intensive studies to solve the above problems, the present inventors have found that Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, and derivatives and / or salts thereof. It has been found that it is a highly safe compound that exhibits excellent wrinkle prevention and improvement effects such as preventing and improving fine lines caused by drying, and more specifically preventing and improving wrinkles caused by photoaging. It came to complete.
  • the present invention provides a wrinkle prevention / improving agent.
  • the wrinkle prevention / improving agent of the present invention is one or two selected from the group consisting of Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, and derivatives and / or salts thereof. Contains more than one type of compound.
  • the present invention provides an oral wrinkle preventing / ameliorating agent.
  • the oral wrinkle preventing / ameliorating agent of the present invention is one kind selected from the group consisting of Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, and derivatives and / or salts thereof. Contains two or more compounds.
  • the present invention provides an injection.
  • the injection of the present invention is one or more selected from the group consisting of Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, and derivatives and / or salts thereof. Contains compounds.
  • the injection of the present invention may further contain a biocompatible gel.
  • the biocompatible gel may be hyaluronic acid and / or collagen.
  • an amino acid when an amino acid is represented, it is represented by a conventional three-letter code such as Val or Pro, and unless otherwise specified, represents an L-form amino acid.
  • an amino acid refers to any compound in which an amino group and a carboxyl group are bonded via at least one carbon atom and can be polymerized by a peptide bond.
  • the amino acid residue which comprises a peptide is shown by the said usual 3 letter notation, and is represented by connecting with a hyphen.
  • Val-Pro means a dipeptide in which the carboxyl group of L-valine and the amino group of L-proline are peptide-bonded.
  • the derivatives means Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, its side chain, the amino group of the N-terminal amino acid, or the C-terminal amino acid. Or a covalent bond to any of the atomic groups.
  • Any of the atomic groups includes a protecting group such as an N-phenylacetyl group or a 4,4′-dimethoxytrityl (DMT) group, and a biopolymer such as a protein, peptide, sugar, lipid, nucleic acid, or the like.
  • Synthetic polymers such as polystyrene, polyethylene, polyvinyl, and polyester, and functional groups such as ester groups, but are not limited thereto.
  • the ester group may include, for example, methyl ester, ethyl ester, other aliphatic esters, or aromatic esters.
  • salt includes acid salts, metal salts, amine salts and the like.
  • the acid salt may include hydrochloride, sulfate, phosphate, lactate, and the like.
  • the metal salt may include an alkali metal salt, an alkaline earth metal salt, and the like.
  • the amine salt may include a triethylamine salt, a benzylamine salt, or the like.
  • a wrinkle prevention / improving agent having an excellent wrinkle prevention / improvement effect can be obtained.
  • one or more compounds selected from the group consisting of Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, and derivatives and / or salts thereof are provided. Used.
  • Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys and their derivatives and / or salts according to the present invention can be synthesized by known methods, extracted from animals, plants, microorganisms, etc. -It can be obtained by purification.
  • Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, their derivatives and / or salts related to the present invention are all excellent in preventing and improving wrinkles as will be proved later.
  • one or more compounds selected from the group consisting of Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, and derivatives and / or salts thereof according to the present invention Is added as an active ingredient in the preparation of a wrinkle prevention / improving agent.
  • the wrinkle prevention / improving agent has a very wide application range, and is applied to various fields such as cosmetics, pharmaceutics, foods including quasi-drugs, and preferably used by being blended in a skin external preparation.
  • composition a wrinkle prevention / improving agent (hereinafter simply referred to as “composition”) as a composition containing the above compound, and the composition exhibits excellent effects such as a wrinkle prevention / improving agent.
  • the content is preferably 0.001 to 10.0% by weight, preferably 0.01 to 5.0% by weight in the total amount of the composition. Is more preferable, and 0.1 to 1.0% by weight is most preferable.
  • the wrinkle prevention / improving agent according to the present invention can be produced according to a conventional method.
  • the component constituting the wrinkle prevention / improving agent is selected from the group consisting of Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, and derivatives and / or salts thereof.
  • it is possible to prepare using only one or two or more kinds of compounds it is usually used for skin external preparations such as cosmetics and pharmaceuticals including quasi-drugs as long as the effects of the present invention are not impaired.
  • Other components to be used can be appropriately blended as necessary.
  • oils examples include oils, surfactants, powders, coloring materials, water, alcohols, thickeners, chelating agents, silicones, antioxidants, ultraviolet absorbers, and humectants. , Fragrances, various medicinal ingredients, preservatives, pH adjusters, neutralizers and the like.
  • the wrinkle prevention / improving agent is used in the form of cosmetics, pharmaceutical compositions, etc., and exhibits an excellent wrinkle prevention / improvement effect.
  • it is preferably applied to cosmetics, pharmaceuticals, etc., and is used in a form of an external preparation for skin that is externally applied to the skin.
  • the wrinkle prevention / improving agent of the present invention can be applied to the skin to prevent wrinkle formation and / or reduce or eliminate wrinkles formed.
  • the usage and dosage of the wrinkle prevention / improving agent of the present invention in such a cosmetic method are not particularly limited and are appropriately determined depending on the dosage form and the condition of wrinkles on the skin to be treated. Applicable amount, for example, 1 to 5 times, for example, 0.1 mL to 1 mL per 1 cm 2 , can be directly rubbed into the skin, or the appropriate amount can be soaked in gauze or the like and applied to the skin.
  • the dosage form of the wrinkle prevention / improving agent is not particularly limited as long as it can exert the effects of the present invention.
  • a solution system a solubilization system, an emulsification system, a powder dispersion system, a water-oil two-layer system , Water-oil-powder three-layer system, ointment, gel, aerosol, etc.
  • the wrinkle prevention / improving agent is applied, for example, in the field of cosmetics including quasi-drugs and pharmaceuticals, and the product forms include, for example, ointments, creams, emulsions, lotions, essences, jellies, gels, packs, Arbitrary forms such as a mask and a foundation can be taken.
  • the wrinkle prevention / improving agent is not particularly limited as long as the oral wrinkle prevention / improving agent dosage form exhibits the effects of the present invention. It can be in the form of a drink, a jelly type beverage or the like.
  • the wrinkle prevention / improving agent is useful as an injectable dosage form for cosmetic surgery and the like, and those containing a biocompatible gel are preferably used. If it is used for etc., it will not specifically limit. Among them, it is preferable to contain hyaluronic acid, type I collagen and the like.
  • the present invention will be specifically described with reference to examples and the like, but the technical scope of the present invention is not limited to these examples and the like.
  • the blending amount is expressed as a percentage by weight unless otherwise specified.
  • the total irradiation dose was 4.6 J / cm 2 .
  • the amount of ultraviolet rays used was a value measured with UVRADIOMETER (UVR-305 / 365D (II), Topcon). After the UV irradiation was completed, a photograph of the back of the mouse was taken, and the degree of wrinkle generation was determined by a method in which the method of Bisett et al. (Bissett DL. Evaluation was performed according to the criteria shown in Table 5 below.
  • the wrinkle evaluation work was individually performed by three measurers, and then a score was determined for the degree of wrinkle generation (hereinafter simply referred to as “score”) through discussion.
  • the following tests were conducted using only hairless mice that formed wrinkles with a score of 7 or higher.
  • the mice were divided into groups of 5 mice so that the average score of each group was the same.
  • Example 1 Val-Pro-Pro formulation, Table 1
  • Example 2 Ile-Pro-Pro formulation, Table 2
  • Comparative Example 1 no drug formulation, Table 4
  • the composition was applied at 100 ⁇ L per time, once a day, 5 days a week, and continuously for 6 weeks.
  • Example 3 Al-His-Lys hydrochloride combination, Table 3
  • Comparative Example 2 no drug combination, Table 4
  • the average value of the degree of wrinkle improvement in the group applied with the composition of Comparative Example 2 was 1.0 point, whereas that in the group applied with the composition of Example 3 was 2.6 points.
  • the application of the composition of Example 3 significantly accelerated wrinkle reduction (Table 7).
  • the risk factor P was less than 0.05.
  • Tables 8 to 20 show preparations for the preparation of wrinkle prevention / amelioration agents according to the present invention, such as external preparations for skin, injections and oral preparations. All of the external preparations for skin had excellent wrinkle prevention and improvement effects.
  • the injection and oral wrinkle prevention / improving agent according to the present invention can also provide wrinkle prevention / improvement effects.
  • Propylene glycol is added to ion-exchanged water, dissolved, heated and maintained at 70 ° C (aqueous phase). The other ingredients were mixed, heated and melted, and kept at 70 ° C. (oil phase). The oil phase was added to the aqueous phase, pre-emulsified, and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well.
  • Propylene glycol was added to ion-exchanged water, dissolved, heated and maintained at 70 ° C (aqueous phase). The other ingredients were mixed, heated and melted, and kept at 70 ° C. (oil phase). The oil phase was added to the aqueous phase, preliminarily emulsified, and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well.
  • phase A A carboxyvinyl polymer was dissolved in a small amount of ion-exchanged water (phase A). Polyethylene glycol 1500 and triethanolamine were added to the remaining ion-exchanged water, dissolved by heating and kept at 70 ° C. (aqueous phase). The other ingredients were mixed, heated and melted, and kept at 70 ° C. (oil phase). The oil phase was added to the aqueous phase for preliminary emulsification, and the A phase was added, and the mixture was uniformly emulsified with a homomixer and cooled to 30 ° C. while stirring well after the emulsification.
  • phase A Polyethylene glycol 1500 and triethanolamine were added to the remaining ion-exchanged water, dissolved by heating and kept at 70 ° C. (aqueous phase). The other ingredients were mixed, heated and melted, and kept at 70 ° C. (oil phase). The oil phase was added to the aqueous phase for preliminary emulsification, and the A phase was
  • the oil phase part was melt
  • the water phase part was dissolved at 70 ° C., the oil phase part was mixed with the water phase part, emulsified with an emulsifier and then cooled to 30 ° C. with a heat exchanger.
  • Carboxyvinyl polymer was uniformly dissolved in ion-exchanged water, while sarcosine and polyoxyethylene (50 mol) oleyl alcohol ether were dissolved in 95% ethanol and added to the aqueous phase. Next, other components were added, and the mixture was neutralized with caustic soda and L-arginine to increase the viscosity.
  • the A phase, the B phase, and the C phase were uniformly dissolved, and the B phase was added to the A phase to solubilize. Subsequently, after adding this to the C phase, it filled and manufactured.
  • Formulation Example 15 Oral preparation 1 g of tripeptide (Ile-Pro-Pro) and 99 g of lactose are mixed well to prepare 100 g of powder.
  • Formulation Example 16 Oral preparation 10 g of tripeptide (Val-Pro-Pro), 350 g of lactose, 360 g of 6% HPC lactose, 65 g of potato starch and 15 g of talc stearate are mixed well and compressed to prepare 1000 tablets. To do.
  • Formulation Example 17 Jelly Beverage 8 g of granulated sugar and 6 g of thickening polysaccharide were mixed in advance, water was added to make the total amount 100 g, and dissolved by heating. After removing the heat, 2 g of Val-Pro-Pro tripeptide, 10 g of isotonic mix, 0.09 g of vitamin mix and 0.3 g of citric acid were added to prepare a jelly beverage by a conventional method.
  • the injection and oral wrinkle prevention / improving agent according to the present invention can also provide wrinkle prevention / improvement effects.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Biochemistry (AREA)
  • Dermatology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La présente invention concerne un agent antiride/de diminution de ride sûr, qui possède un effet global antiride/de diminution de ride tel qu’il permet de prévenir/diminuer les rides dues au vieillissement ou au photo-vieillissement. Ledit agent antiride/de diminution de ride contient un type ou deux types ou davantage de composés sélectionnés dans un groupe comprenant Val-Pro-Pro, Ile-Pro-Pro, Ala-His-Lys, et des dérivés et/ou des sels de ceux-ci.
PCT/JP2009/064666 2008-08-29 2009-08-21 Agent de diminution de ride WO2010024204A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008-221532 2008-08-29
JP2008221532A JP2010053099A (ja) 2008-08-29 2008-08-29 しわ改善剤

Publications (1)

Publication Number Publication Date
WO2010024204A1 true WO2010024204A1 (fr) 2010-03-04

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PCT/JP2009/064666 WO2010024204A1 (fr) 2008-08-29 2009-08-21 Agent de diminution de ride

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JP (1) JP2010053099A (fr)
WO (1) WO2010024204A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9067972B2 (en) 2008-12-15 2015-06-30 Calpis Co., Ltd. Skin aging-inhibiting peptide

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09278659A (ja) * 1996-02-09 1997-10-28 Taisho Pharmaceut Co Ltd 口唇用外用剤
JPH1149628A (ja) * 1997-07-31 1999-02-23 Shiseido Co Ltd しわ改善用化粧料
JP2002128651A (ja) * 2000-10-25 2002-05-09 Kose Corp 光老化抑制剤およびそれを含有することを特徴とする皮膚外用剤
JP2002284668A (ja) * 2001-03-26 2002-10-03 Cosmo Products Kk クスミの予防・治療剤
JP2005511650A (ja) * 2001-10-05 2005-04-28 プロサイト コーポレイション 皮膚の色素過剰症の処置法
JP2005220085A (ja) * 2004-02-06 2005-08-18 Kose Corp 老化防止剤、並びにそれを用いた皮膚外用剤及び細胞賦活方法
JP2006265253A (ja) * 2005-03-24 2006-10-05 Neutrogena Corp シリコーン中水型エマルション組成物
JP2007515381A (ja) * 2003-11-17 2007-06-14 セダーマ テトラペプチドとトリペプチドの混合物を含む組成物
JP2007530488A (ja) * 2004-03-26 2007-11-01 ディーエスエム アイピー アセッツ ビー．ブイ． 化粧品用途のためのアリールアルキル酸のアミノ酸およびペプチド共役体

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09278659A (ja) * 1996-02-09 1997-10-28 Taisho Pharmaceut Co Ltd 口唇用外用剤
JPH1149628A (ja) * 1997-07-31 1999-02-23 Shiseido Co Ltd しわ改善用化粧料
JP2002128651A (ja) * 2000-10-25 2002-05-09 Kose Corp 光老化抑制剤およびそれを含有することを特徴とする皮膚外用剤
JP2002284668A (ja) * 2001-03-26 2002-10-03 Cosmo Products Kk クスミの予防・治療剤
JP2005511650A (ja) * 2001-10-05 2005-04-28 プロサイト コーポレイション 皮膚の色素過剰症の処置法
JP2007515381A (ja) * 2003-11-17 2007-06-14 セダーマ テトラペプチドとトリペプチドの混合物を含む組成物
JP2005220085A (ja) * 2004-02-06 2005-08-18 Kose Corp 老化防止剤、並びにそれを用いた皮膚外用剤及び細胞賦活方法
JP2007530488A (ja) * 2004-03-26 2007-11-01 ディーエスエム アイピー アセッツ ビー．ブイ． 化粧品用途のためのアリールアルキル酸のアミノ酸およびペプチド共役体
JP2006265253A (ja) * 2005-03-24 2006-10-05 Neutrogena Corp シリコーン中水型エマルション組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9067972B2 (en) 2008-12-15 2015-06-30 Calpis Co., Ltd. Skin aging-inhibiting peptide

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