WO2001019323A1 - Inhibiteurs de l'activite tyrosinase et cosmetiques - Google Patents

Inhibiteurs de l'activite tyrosinase et cosmetiques Download PDF

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Publication number
WO2001019323A1
WO2001019323A1 PCT/JP1999/005014 JP9905014W WO0119323A1 WO 2001019323 A1 WO2001019323 A1 WO 2001019323A1 JP 9905014 W JP9905014 W JP 9905014W WO 0119323 A1 WO0119323 A1 WO 0119323A1
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WO
WIPO (PCT)
Prior art keywords
weight
tyrosinase activity
parts
group
cosmetic
Prior art date
Application number
PCT/JP1999/005014
Other languages
English (en)
Japanese (ja)
Inventor
Kokki Sakai
Ryuichiro Kondo
Kuniyoshi Shimizu
Hiroaki Sato
Original Assignee
Kansai Koso Co., Ltd.
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
Priority to JP10063167A priority Critical patent/JPH11255637A/ja
Application filed by Kansai Koso Co., Ltd. filed Critical Kansai Koso Co., Ltd.
Priority to PCT/JP1999/005014 priority patent/WO2001019323A1/fr
Priority to AU56507/99A priority patent/AU5650799A/en
Publication of WO2001019323A1 publication Critical patent/WO2001019323A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • the present invention relates to a tyrosinase activity inhibitor that can be used as an active ingredient for preventing or healing skin spots and freckles, and as a whitening cosmetic, and various cosmetics using the inhibitor.
  • vitamins, hydroquinone, kojic acid, thiol-based compounds, and various animal and plant extracts are known as substances that inhibit melanin production by inhibiting tyrosinase activity.
  • cosmetics incorporating these have been developed and commercialized.
  • An object of the present invention is to strongly increase tyrosinase activity involved in melanin production.
  • An object of the present invention is to provide a tyrosinase activity inhibitor that can be used for cosmetics that inhibits, prevents or cures spots and sopacas, and has a whitening effect.
  • Another object of the present invention is to provide a cosmetic that can suppress melanin production by suppressing tyrosinase activity, prevent or cure spots and freckles, and provide a whitening effect.
  • the present inventors have focused on a flavonoid compound having a 4-substituted resorcinol skeleton in order to solve the above problems. And a flavonoid compound having a 4-substituted resorcinol skeleton, having this skeleton and having a carbonyl group, an azo group or a chlorine element at a position indicated by an arrow in the following formulas (1) to (9).
  • the present invention was completed by finding that a flavonoid compound having a specific structure, which does not have an excellent tyrosinase inhibitory activity, was obtained.
  • R is the same or different and represents a hydroxyl group, a carbonyl group, an alkyl group having 1 to 9 carbon atoms, an alkenyl group or an alkoxy group, and n is an integer of 0 to 3.
  • a tyrosinase activity inhibitor comprising at least one compound selected from the group consisting of the flavonoid compounds represented by the formulas (1) to (9).
  • a cosmetic comprising the tyrosinase activity inhibitor.
  • tyrosinase activity inhibitor for producing a cosmetic or a whitening cosmetic.
  • the tyrosinase activity inhibitor of the present invention comprises, as an active ingredient, one compound selected from the group consisting of the flavonoid compounds represented by the formulas (1) to (9) or a mixture of two or more compounds. Contained. Further, in addition to these flavonoid compounds, a compound having a known tyrosinase activity inhibiting ability may be contained, if desired.
  • Such a flavonoid compound can be easily designed and synthesized within a range of a substituent by a known method.
  • the preparation of the flavonoid compounds represented by the formulas (1) to (9) can be carried out, for example, by subjecting flavonoids or isoflavonides obtained by extraction from nature to nitration and amination by a conventional method. It can be easily obtained by a method of adding a hydroxyl group through the method.
  • flavonoids or isoflavonoids from nature for example, first, finely crush higher plants with a crusher, immerse them in ether, and keep them at room temperature for 24 hours. Then, after stirring, the mixture was filtered to obtain an ether extract, the solvent was distilled off from the obtained ether extract, silica gel chromatography was performed, and silica gel MP LC treatment was performed twice to obtain each flavonoid compound. And a fraction of an isoflavonide compound. The obtained fraction is analyzed by LC-HRF ABMS (liquid chromatography-high resolution fast atom bombardment mass spectometry) and NMR to purify and isolate the desired flavonoid and isoflavonide.
  • LC-HRF ABMS liquid chromatography-high resolution fast atom bombardment mass spectometry
  • the tyrosinase activity inhibitor of the present invention may contain the above-mentioned active ingredient, and its content is preferably 0.0001% by weight or more.
  • the cosmetic of the present invention contains the tyrosinase activity inhibitor as an essential component. Preferably, it can be used as a whitening cosmetic, a cosmetic for inhibiting or healing Shimizusobacus, which exhibits an inhibitory action on melanin production based on an inhibitory action on tyrosinase activity.
  • the mixing ratio of the tyrosinase activity inhibitor to cosmetics is 0.001% by weight or more, especially 0.0001 to 20% by weight, in terms of the flavonoid compound as an active ingredient, 0.0 001 to 10% by weight is desirable New
  • the cosmetic of the present invention may contain various materials in addition to the tyrosinase activity inhibitor according to the purpose.
  • the desired effect can be synergistically improved by blending a conventionally known whitening agent, anti-wrinkle agent, humectant or a mixture thereof.
  • whitening agent examples include kojic acid, ascorbic acid, hydroquinone, thiol compounds, compounds having a 4-substituted resorcinol skeleton other than the flavonoid compounds and exhibiting a tyrosinase activity inhibitory action, Derivatives, extracts of animals and plants containing these, or mixtures thereof.
  • humectant examples include polyhydric alcohols such as glycerin, propylene glycol, 1,3-butylene glycol, sonoreitol, mannitore, polyethylene glycol, dipropylene glycol, and the like.
  • NMF components such as amino acids, sodium lactate and sodium pyrrolidone carboxylate; hyaluronic acid; collagen; elastin; chondroitin sulfate; fibronectin; ceramides; Examples thereof include water-soluble polymer substances such as chitosan and mixtures thereof.
  • the mixing ratio of the whitening agent, anti-wrinkle agent or humectant is preferably 0.001 to 100 times, more preferably 0.01 to 100 times the active ingredient of the tyrosinase activity inhibitor. A range of 0.05 to 500 times is desirable.
  • the cosmetics of the present invention are generally blended according to the type thereof, for example, fats and oils, surfactants, alcohols, fatty acids, preservatives, bactericides, thickeners, anti-inflammatory agents, antioxidants, Dyes, fragrances, water-soluble polymers, ultraviolet absorbers, chelating agents, pH adjusters, buffers, purified water, or mixtures thereof can also be appropriately blended.
  • thickener examples include sodium alginate, xanthan gum, aluminum silicate, malmo oral seed extract, tragacanth gum, starch, and other natural polymer substances; methylcellulose, soluble starch, hydroxyxetil Semi-synthetic high-molecular substances such as senorellose, canolepoxmethinoresenolylose, soluble starch, and cationized cellulose; synthetic high-molecular substances such as carboxy vinyl polymer and polyvinyl alcohol; and mixtures thereof.
  • preservatives examples include benzoate, sorbate, dihydroacetate, paraoxybenzoate, 2,2,4'-trichloro-2, -hydroxydiphenynooleate, 3,4 , 4'-trichlorocanolenolide, benzalkonium chloride, ethanol or a mixture thereof.
  • antioxidants examples include dibutylhydroxytoluene, butylhydroxyanisole, vitamin E, propyl gallate, and a mixture thereof.
  • Examples of the ultraviolet absorber include 4-methoxybenzophenone, octyldimethyl balaminobenzoate, ethylhexylparamethyxine cinnamate, titanium oxide, kaolin, talc or a mixture thereof. Is mentioned.
  • chelating agent examples include ethylenediaminetetraacetate, potassium phosphate, hexamethalinate, citrate, tartaric acid, dalconic acid, and mixtures thereof.
  • pH adjuster examples include sodium hydroxide, potassium hydrogen phosphate, potassium carbonate, and citric acid.
  • the cosmetic of the present invention comprises the above-mentioned active ingredient and other components as necessary, By blending them according to the purpose, they can be prepared as pharmaceuticals, quasi-drugs or cosmetics. For example, lotions, emulsions, creams, packs, skin cleansers, haptics, plasters, pastes, ointments, essences, gels, shampoos, rinses, know-how, foundations, lotions , Facial cleansers, sunscreens, treatment oils, hair tonics, hair tonics, bath preparations and the like.
  • components conventionally used for such applications can be appropriately selected and blended.
  • the tyrosinase activity inhibitor of the present invention contains the flavonoid compound as an active ingredient, the tyrosinase activity involved in melanin production can be strongly suppressed.
  • the cosmetic of the present invention contains the tyrosinase activity inhibitor, it suppresses tyrosinase activity to suppress melanin production, and achieves whitening, suppression of spots and freckles, and cure. Can be expected.
  • the active ingredient can be stably incorporated into cosmetics, so that a wide variety of cosmetics can be obtained.
  • tyrosinase activity inhibition test shown below was performed using a flavonoid compound represented by the following formula, in which n of the formula (1) was 0, prepared by a conventional method.
  • IC 5 which was measured using a spectrophotometer 4 7 5 nm absorbance after incubator base one preparative, against the control. I asked. As a result, IC 5. Was 13.2 / zM, which was found to have excellent tyrosinase inhibitory activity.
  • Anthocyanin extracted from nature by a conventional method was slowly added dropwise while cooling a mixture of nitric acid and sulfuric acid in an ice bath.
  • a tyrosinase activity inhibition test was carried out in the same manner as in Example 1 using the obtained 2 ', 4'-dihydroxytosyanine as a sample. As a result, the IC 50 was 2.8 ⁇ M, and it was found to have excellent tyrosinase inhibitory activity.
  • Example 2 4,1-dihydroxyflavan represented by the following formula, in which ⁇ of the above formula (5) was 0, was prepared using flavan extracted from nature by a conventional method.
  • Example 2 4′-dihydroxyisoflavanone represented by the following formula wherein n of the formula (7) is 0 was prepared using isobrabanone extracted from nature by a conventional method. did.
  • stearic acid 3.0 parts by weight of cetyl alcohol, 1.0 parts by weight of stearyl alcohol, 6.5 parts by weight of liquid paraffin, 10.0 parts by weight of cerin, sorbitan mono stearate 1.5 parts by weight, polyoxyethylene monostearate (25 ⁇ . ⁇ .) 3.0 parts by weight and 2 ′, 4 represented by the following formula where ⁇ in the above formula (3) is 0 '-Dihydroxyarrone 1.0 parts by weight was ripened and dissolved.
  • 5.0 parts by weight of 1,3-butylene glycol, 0.1 part by weight of potassium hydroxide and 64.9 parts by weight of purified water were mixed with this solution, and then cooled to prepare a cream. .
  • n in the above formula (4) is 0 0.1 part by weight of 4,1-dihydroxybiflavanone and 0.4 part by weight of 2 ', 4'-dihydroxyflavanone in which n in the above formula (7) is 0 were dissolved by heating.
  • 5.0 parts by weight of 1,3-butylene glycol, 0.1 part by weight of potassium hydroxide, 0.2 parts by weight of arbutin and 65.2 parts by weight of purified water were mixed with this solution. Upon cooling, a cream was prepared.
  • n of the formula (8) is 0, 5.0 parts by weight of polyoxyethylene cetyl ether, 2.0 parts by weight of propylene glycol, 1-medium 0.1 parts by weight of ethanol, 15.0 parts by weight of ethanol and 7.7.4 parts by weight of purified water were stirred until uniform to prepare a lotion.
  • n in the above formula (5) is 0, 2.0 parts by weight of polyoxyethylene hydrogenated castor oil (60 EO), and 15.0 parts by weight of ethanol Parts, 1,3-butylene glycol 4.0 weight And 78.5 parts by weight of purified water were stirred until uniform to prepare a lotion.
  • squalane 8.0 parts by weight of squalane, 2.0 parts by weight of petrolatum, 0.5 parts by weight of beeswax, 0.8 parts by weight of sorbitan sesquiolate, polyoxyethylene oleyl ether (20E.O.) 1.2 Parts by weight and 0.5 parts by weight of 2 ′, 4′-dihydroxyisoflavan in which n in the formula (6) is 0 were dissolved by heating.
  • To the obtained solution were added 0.2 parts by weight of hydroxyxethyl cellulose, 2.0 parts by weight of propylene glycol, 0.1 part by weight of dicalium glycyrrhizinate, and 87.2 parts by weight of purified water. After mixing, the mixture was cooled to prepare an emulsion.

Abstract

L'invention concerne des inhibiteurs de l'activité tyrosinase renfermant au moins un composé pouvant être l'un des composés flavonoïdes représentés par les formules (1) à (9). L'invention concerne également des cosmétiques à effet éclaircissant résultant d'une action inhibitrice sur la formation de mélanine, par inhibition de l'activité tyrosinase.
PCT/JP1999/005014 1998-03-13 1999-09-14 Inhibiteurs de l'activite tyrosinase et cosmetiques WO2001019323A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP10063167A JPH11255637A (ja) 1998-03-13 1998-03-13 チロシナーゼ活性阻害剤及び化粧料
PCT/JP1999/005014 WO2001019323A1 (fr) 1998-03-13 1999-09-14 Inhibiteurs de l'activite tyrosinase et cosmetiques
AU56507/99A AU5650799A (en) 1999-09-14 1999-09-14 Tyrosinase activity inhibitors and cosmetics

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10063167A JPH11255637A (ja) 1998-03-13 1998-03-13 チロシナーゼ活性阻害剤及び化粧料
PCT/JP1999/005014 WO2001019323A1 (fr) 1998-03-13 1999-09-14 Inhibiteurs de l'activite tyrosinase et cosmetiques

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WO2001019323A1 true WO2001019323A1 (fr) 2001-03-22

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WO (1) WO2001019323A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003097004A1 (fr) * 2002-05-22 2003-11-27 Korea Research Institute Of Bioscience And Biotechnology Compositions blanchissantes comprenant des composes inhibant la biosynthese de la melanine
WO2007077259A1 (fr) * 2006-01-05 2007-07-12 Symrise Gmbh & Co. Kg Preparations actives synergiques comprenant des derives de diphenylmethane et en outre des composes reduisant l'eclaircissement de la peau et/ou des cheveux et/ou la keratose senile
WO2007077260A1 (fr) * 2006-01-05 2007-07-12 Symrise Gmbh & Co. Kg Formules de faible teneur en huile comprenant des dérivés de diphénylméthane
JP2007291102A (ja) * 2006-04-21 2007-11-08 L'oreal Sa ヒドロキシル化ジフェニルメタン誘導体を含む組成物
FR2939136A1 (fr) * 2008-12-02 2010-06-04 Galderma Res & Dev Nouveaux composes 4-(heterocycloalkyl)-benzene-1,3-diol comme inhibiteurs de la tyrosinase, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique
US9283170B2 (en) 2010-05-18 2016-03-15 Conopco, Inc. Personal care composition
EP3009123A1 (fr) * 2008-12-22 2016-04-20 Pola Chemical Industries Inc. Inhibiteur de production de mélamine
WO2023221665A1 (fr) * 2022-05-17 2023-11-23 帕潘纳(北京)科技有限公司 Composé diphénolique, son procédé de préparation et son utilisation

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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JPH11255637A (ja) * 1998-03-13 1999-09-21 Kansai Kouso Kk チロシナーゼ活性阻害剤及び化粧料
DE10324566A1 (de) * 2003-05-30 2004-12-16 Symrise Gmbh & Co. Kg Verwendung von Diphenylmethan-Derivaten als Tyrosinase-Inhibitoren
JP4593474B2 (ja) * 2003-10-30 2010-12-08 明治製菓株式会社 チロシナーゼ活性阻害剤及び顔面血流改善剤
JP5209848B2 (ja) * 2006-01-12 2013-06-12 ポーラ化成工業株式会社 皮膚外用剤
JP5198732B2 (ja) * 2006-01-12 2013-05-15 ポーラ化成工業株式会社 メラニン生成抑制剤
KR101259565B1 (ko) * 2011-03-29 2013-04-30 건국대학교 산학협력단 참싸리로부터 분리한 타이로시네이즈 저해활성을 가지는 화합물 및 이를 포함하는 약물학적 조성 및 용도

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003097004A1 (fr) * 2002-05-22 2003-11-27 Korea Research Institute Of Bioscience And Biotechnology Compositions blanchissantes comprenant des composes inhibant la biosynthese de la melanine
WO2007077259A1 (fr) * 2006-01-05 2007-07-12 Symrise Gmbh & Co. Kg Preparations actives synergiques comprenant des derives de diphenylmethane et en outre des composes reduisant l'eclaircissement de la peau et/ou des cheveux et/ou la keratose senile
WO2007077260A1 (fr) * 2006-01-05 2007-07-12 Symrise Gmbh & Co. Kg Formules de faible teneur en huile comprenant des dérivés de diphénylméthane
JP2007291102A (ja) * 2006-04-21 2007-11-08 L'oreal Sa ヒドロキシル化ジフェニルメタン誘導体を含む組成物
EP2529735A1 (fr) * 2008-12-02 2012-12-05 Galderma Research & Development Nouveaux composés 4-(héterocycloalkyl)-benzene-1,3-diol comme inhibiteurs de la tyrosinase, leur procédé de préparation et leur utilisation en médecine humaine ainsi qu'en cosmétique
WO2010063773A1 (fr) * 2008-12-02 2010-06-10 Galderma Research & Development Nouveaux composés de 4- (hétérocycloalkyl)benzène-1,3-diol utilisés comme inhibiteurs de la tyrosinase, leur procédé de préparation et leur utilisation en médecine humaine et dans les cosmétiques
CN102238948A (zh) * 2008-12-02 2011-11-09 盖尔德马研究及发展公司 作为酪氨酸酶抑制剂的新颖的4-(杂环烷基)苯-1,3-二酚化合物，其制备方法及其在人类药物及化妆品中的应用
AU2009324080B2 (en) * 2008-12-02 2012-10-04 Galderma Research & Development Novel 4-(heterocycloalkyl)benzene-1,3-diol compounds as tyrosinase inhibitors, process for the preparation thereof and use thereof in human medicine and also in cosmetics
FR2939136A1 (fr) * 2008-12-02 2010-06-04 Galderma Res & Dev Nouveaux composes 4-(heterocycloalkyl)-benzene-1,3-diol comme inhibiteurs de la tyrosinase, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique
US8372879B2 (en) 2008-12-02 2013-02-12 Galderma Research & Development 4-(heterocycloalkyl) benzene-1,3-diol compounds as tyrosinase inhibitors, process for the preparation thereof and use thereof in human medicine and also in cosmetics
RU2482116C2 (ru) * 2008-12-02 2013-05-20 Галдерма Ресерч Энд Девелопмент Новые 4-(гетероциклоалкил)бензол-1,3-диольные соединения в качестве ингибиторов тирозиназ, способ их получения и их применение в лечении человека, а также в косметических средствах
KR101290504B1 (ko) 2008-12-02 2013-07-29 갈데르마 리써어치 앤드 디벨로프먼트 타이로시나아제 억제제로서의 신규 ４-(헤테로시클로알킬)벤젠-１,３-디올 화합물, 이의 제조 방법 및 인간 의약 및 또한 화장품에서의 이의 용도
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