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WO2011096330A1 - Agent améliorant la pigmentation - Google Patents

Agent améliorant la pigmentation Download PDF

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Publication number
WO2011096330A1
WO2011096330A1 PCT/JP2011/051696 JP2011051696W WO2011096330A1 WO 2011096330 A1 WO2011096330 A1 WO 2011096330A1 JP 2011051696 W JP2011051696 W JP 2011051696W WO 2011096330 A1 WO2011096330 A1 WO 2011096330A1
Authority
WO
WIPO (PCT)
Prior art keywords
pigmentation
skin
improving agent
external preparation
general formula
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2011/051696
Other languages
English (en)
Japanese (ja)
Inventor
優子 斉藤
千尋 近藤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pola Orbis Holdings Inc
Original Assignee
Pola Chemical Industries Inc
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 Pola Chemical Industries Inc filed Critical Pola Chemical Industries Inc
Priority to JP2011552748A priority Critical patent/JPWO2011096330A1/ja
Publication of WO2011096330A1 publication Critical patent/WO2011096330A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/221—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
    • 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

Definitions

  • the present invention relates to a novel pigmentation-improving agent and a skin external preparation suitable for cosmetics, and specifically comprises a compound represented by the following general formula (1) and / or a pharmacologically acceptable salt thereof.
  • the present invention relates to a pigmentation-improving agent and a skin external preparation containing the pigmentation-improving agent.
  • the term cosmetic is defined as including quasi drugs. (Wherein R 1 represents a linear or branched alkyl group having 1 to 6 carbon atoms, and R 2 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.)
  • Pigmentation, blemishes, liver spots, senile pigment spots, etc. after sunburn in the skin are a state in which melanin production is remarkably enhanced by activation of pigment cells (melanocytes) present in the skin.
  • Ingredients that have the action of preventing or improving the occurrence and deterioration of skin pigment troubles include compounds having a whitening action (whitening agents) such as ascorbic acids, hydrogen peroxide, colloidal sulfur, glutathione, hydroquinone, and catechol. It is well known (for example, see Non-Patent Document 1 and Non-Patent Document 2). And skin external preparations containing these active ingredients are widely used.
  • whitening agents various mechanisms of action of compounds known as whitening agents have been reported, including tyrosinase enzyme inhibition, tyrosinase-related proteolysis, and inhibition of melanin transport by suppressing dendrite elongation in melanocytes.
  • target molecules for each mechanism of action.
  • a small organic molecule that interacts appropriately with each target molecule is useful.
  • the structural characteristics of small organic molecules that interact appropriately with each target molecule are different for each target molecule, it is important to optimize the chemical structure in order to maximize the pharmacological effects of the small organic molecules.
  • the current whitening agent research targets compounds that have high efficacy and selectivity against existing target molecules, as well as compounds that simultaneously act on multiple whitening mechanisms, as well as new It spreads to compounds that have a mechanism of action.
  • Amino acids are a general term for organic compounds having both amino and carboxyl functional groups in their molecules.
  • ⁇ -amino acids are actively used as protein structural units for expressing various functions in living bodies. Research has been done.
  • Various physiological activities have been reported for ⁇ -amino acids such as cysteine, arginine, valine, threonine, serine and glycine existing in living bodies, and peptide derivatives containing ⁇ -amino acids as constituent elements.
  • the physiological activities of ⁇ -amino acids and derivatives thereof include anti-aging action (see, for example, Patent Document 1), moisturizing action (for example, see Patent Document 2), whitening action (for example, Patent Document) even in the cosmetic field alone.
  • amino acids and derivatives thereof are not only effective, but also have excellent solubility, separation and water solubility, and high safety can be expected. Therefore, their incorporation into cosmetics and the like has been actively studied.
  • physiological activities such as anti-aging, moisturizing or whitening action of the ⁇ -amino acid and its derivatives are not sufficiently feasible, and research on ⁇ -amino acids and their derivatives that enhance the physiological activity continues. It has been broken.
  • glycine derivatives belonging to ⁇ -amino acids betaine-type amphoteric surfactant activity or semipolar surfactant activity (see, for example, Patent Document 4 and Patent Document 5) can be applied to N-acyl and N-long chain alkylglycine derivatives. ) And the like, and is blended as a surfactant in cosmetics, cleaning agents, hair styling agents, toothpastes, and the like.
  • whitening action for example, refer to Patent Document 6
  • N-alkylglycine derivative especially N-methylglycine (sarcosine), wrinkle improving action ( For example, see Patent Document 7), and no whitening effect is known at all.
  • JP 2004-115438 A Japanese Patent Laid-Open No. 2002-087928 Japanese Patent Laid-Open No. 05-301811 JP 2002-322491 A JP 2001-261431 A JP 2004-315384 A WO2007 / 013662 pamphlet
  • the present invention has been made under such circumstances, and provides a pigmentation-improving agent having a novel mother nucleus, which is excellent in pigmentation-improving action, and a skin external preparation containing the pigmentation-improving agent.
  • the task is to do.
  • a pigmentation-improving agent comprising a compound represented by the following general formula (1) and / or a pharmacologically acceptable salt thereof. (Wherein R 1 represents a linear or branched alkyl group having 1 to 6 carbon atoms, and R 2 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.)
  • the compound represented by the general formula (1) is a compound represented by the following general formula (2) and / or a pharmacologically acceptable salt thereof, ⁇ 1>
  • the pigmentation-improving agent described in 1. In the formula, R 3 represents a linear or branched alkyl group having 1 to 6 carbon atoms.
  • ⁇ 3> The pigmentation-improving agent according to ⁇ 2>, wherein the compound represented by the general formula (2) is N-methylglycine and / or a pharmacologically acceptable salt thereof. .
  • a skin external preparation comprising the pigmentation-improving agent according to any one of ⁇ 1> to ⁇ 3>.
  • ⁇ 5> The external skin preparation according to ⁇ 4>, wherein the pigmentation-improving agent is contained in an amount of 0.0001% by mass to 20% by mass with respect to the total amount of the external skin preparation.
  • ⁇ 6> The external preparation for skin according to ⁇ 4> or ⁇ 5>, which is a cosmetic (including quasi-drugs).
  • ⁇ 7> The external preparation for skin according to any one of ⁇ 4> to ⁇ 6>, which is in the form of a water-in-oil emulsifier.
  • ⁇ 8> The external preparation for skin according to any one of ⁇ 4> to ⁇ 7>, which is for whitening.
  • a method for improving skin pigmentation wherein the compound represented by the following general formula (1) and / or a pharmacologically acceptable salt thereof is administered to a site where pigmentation improvement is necessary.
  • a method characterized by that. wherein R 1 represents a linear or branched alkyl group having 1 to 6 carbon atoms, and R 2 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.
  • the pigmentation-improving agent of the present invention comprises the compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof.
  • the pigmentation-improving agent of the present invention has the effect of preventing pigmentation in addition to the effect of thinning and eliminating the pigmentation that has already been formed, and the compound having the effect of preventing pigmentation. It is included in the pigmentation improving agent of the invention. That is, the pigmentation-improving agent of the present invention is a compound that is contained in the general formula (1) and has an action of preventing or improving pigmentation.
  • the pigmentation-improving action in the present invention can be determined, for example, based on whether or not it has a pigmentation-inhibiting action in “Evaluation of pigmentation-inhibiting action by ultraviolet irradiation using colored guinea pigs” described in Examples below.
  • having a pigmentation inhibitory action means that the evaluation substance administration group has a pigmentation inhibitory action compared with the control group (solvent control group). . It is preferable that the pigmentation inhibitor of the present invention has a statistically significant difference in the pigmentation inhibitory action of the evaluation substance administration group as compared with the control group.
  • the compound represented by the general formula (1) and / or a pharmacologically acceptable salt thereof has an excellent effect of preventing or improving pigmentation, and is soluble in a hydrophilic or lipophilic medium. It is easy to formulate into a topical skin preparation. Furthermore, since it is excellent in stability and skin retention in the preparation, it exhibits an excellent effect in preventing or improving pigmentation. Also, the pigmentation prevention or amelioration action of such compounds is the inhibition of tyrosinase activity such as tyrosinase enzyme inhibitory action, tyrosinase gene expression inhibitory action, tyrosinase protein expression inhibitory action, tyrosinase-related proteolytic action, etc.
  • tyrosinase activity such as tyrosinase enzyme inhibitory action, tyrosinase gene expression inhibitory action, tyrosinase protein expression inhibitory action, tyrosinase-related proteolytic action, etc.
  • melanin production is suppressed by a new mechanism of action. Therefore, it exhibits an improving action on pigmentation that cannot be improved by glycine or acylglycine.
  • R 1 represents a linear or branched alkyl group having 1 to 6 carbon atoms
  • R 2 represents a hydrogen atom or a linear or branched group having 1 to 4 carbon atoms.
  • R 1 is preferably a linear or branched alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.
  • Specific examples of R 1 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group and the like.
  • R 2 is preferably a hydrogen atom or a methyl group.
  • R 2 include a hydrogen atom, a methyl group, an ethyl group, a propyl group, and a butyl group.
  • R 3 represents a linear or branched alkyl group having 1 to 6 carbon atoms.
  • R 3 represents a linear or branched alkyl group having 1 to 6 carbon atoms.
  • R 3 is preferably a linear or branched alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.
  • Specific examples of R 3 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group and the like.
  • Specific examples of the compound represented by the general formula (2) and / or a pharmacologically acceptable salt thereof include N-methylglycine, N-ethylglycine, N- (n-propyl) glycine, N- (Isopropyl) glycine, N- (n-butyl) glycine, N- (isobutyl) glycine, N- (tert-butyl) glycine, N- (n-pentylglycine), N- (n-hexylglycine) and their Examples thereof include pharmacologically acceptable salts. More preferably, N-methylglycine, N-ethylglycine, and pharmacologically acceptable salts thereof can be used.
  • the compound represented by the general formula (2) and / or a pharmacologically acceptable salt thereof has a particularly excellent pigmentation preventing or improving action. Moreover, it is excellent in solubility in a hydrophilic or lipophilic medium, and can be easily formulated into a skin external preparation or the like. Furthermore, it has excellent stability and skin retention in the preparation, and exhibits excellent effects in preventing or improving pigmentation.
  • Specific examples of the compound represented by the general formula (1) that do not belong to the compound represented by the general formula (2) include N-methylglycine methyl ester, N-methylglycine. Ethyl ester, N-methyl glycine propyl ester, N-methyl glycine butyl ester, N-ethyl glycine methyl ester, N-ethyl glycine ethyl ester, N-ethyl glycine propyl ester, N-ethyl glycine butyl ester, N-propyl glycine methyl Ester, N-propyl glycine ethyl ester, N-propyl glycine propyl ester, N-propyl glycine butyl ester, N-butyl glycine methyl ester, N-butyl glycine ethyl ester, N-butyl glycine propyl ester, N-butyl
  • the compound represented by the general formula (1) or the general formula (2) is a commercially available glycine derivative having a protecting group such as a tert-butoxycarbonyl group (Boc group), for example, anhydrous N, It can be produced by performing an alkylation reaction using sodium hydride and the corresponding alkyl halide in an N-dimethylformamide solvent, and then removing the protective group by a deprotection reaction. Moreover, you may use what is marketed and can also purchase from reagent manufacturers, such as Tokyo Chemical Industry Co., Ltd. Such a compound can be used as it is as a pigmentation-improving agent, but can also be treated with a pharmacologically acceptable acid or base, converted into a salt form, and used as a salt.
  • a protecting group such as a tert-butoxycarbonyl group (Boc group)
  • Boc group tert-butoxycarbonyl group
  • inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, carbonate; maleate, fumarate, oxalate, citrate, lactate, tartrate, methanesulfonate, para Organic acid salts such as toluene sulfonate and benzene sulfonate; alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as calcium salt and magnesium salt; triethylamine salt, triethanolamine salt, ammonium salt, And organic amine salts such as monoethanolamine salt and piperidine salt; basic amino acid salts such as lysine salt and alginate;
  • the pigmentation-improving agent of the present invention thus obtained can be used as an active ingredient of an external preparation for skin because it has an excellent pigmentation-preventing and improving action.
  • the mechanism of action of the pigmentation-improving agent of the present invention is unknown in detail, tyrosinase activity inhibitory action such as tyrosinase enzyme inhibitory action, tyrosinase gene expression inhibitory action, tyrosinase-related proteolytic action, etc.
  • melanin production-suppressing effect by inhibiting melanin transfer by suppressing dendrite elongation in melanocytes, it is estimated that melanin production is suppressed by a new mechanism of action.
  • the total amount of the pigmentation-improving agent of the present invention is 0.0001% by mass to 20% by mass, more preferably 0%, based on the total amount of the external preparation for skin.
  • the content is preferably 0.001 to 10% by mass, more preferably 0.005 to 5% by mass.
  • the pigmentation-improving agent of the present invention and the external preparation for skin containing the pigmentation-improving agent are for preventing or improving pigmentation, and “for preventing or improving pigmentation” is achieved by preventing or improving pigmentation.
  • Applications mainly intended for the purpose, for example, "whitening", “stain improvement”, and the like are included.
  • the external preparation for skin of the present invention contains the pigmentation-improving agent of the present invention.
  • the skin external preparation of the present invention may contain only one type of pigmentation-improving agent of the present invention, or may contain two or more types in combination.
  • the preparation for external use of the skin of the present invention is for prevention or improvement of pigment-related abnormalities such as “for pigmentation prevention or improvement”, “for whitening”, “for spot improvement”, etc. by incorporating the pigmentation improving agent of the present invention. As effective.
  • the skin external preparation of the present invention can contain optional components usually used in skin external preparations in addition to the pigmentation-improving agent that is an essential component.
  • optional ingredients include hydrocarbons such as squalane, petrolatum, microcrystalline wax, esters such as jojoba oil, carnauba wax, octyldodecyl oleate, triglycerides such as olive oil, beef tallow and coconut oil.
  • Fatty acids such as stearic acid, oleic acid, retinoic acid, higher alcohols such as oleyl alcohol, stearyl alcohol, octyldodecanol, anionic surface activity such as sulfosuccinic acid ester and sodium polyoxyethylene alkyl sulfate Agents, amphoteric surfactants such as alkylbetaine salts, cationic surfactants such as dialkylammonium salts, sorbitan fatty acid esters, fatty acid monoglycerides, polyoxyethylene adducts thereof, polyoxyethylene alkyl ethers, polyoxyethylenes
  • Nonionic surfactants such as fatty acid esters, polyhydric alcohols such as polyethylene glycol, glycerin, 1,3-butanediol, thickening / gelling agents, antioxidants, UV absorbers, Coloring agents, preservatives, powders and the like can be contained. Manufacture can be accomplished without difficulty by treating these
  • the pigmentation-improving agent and optional components of the present invention can be processed according to conventional methods to prepare lotions, emulsions, essences, creams, pack cosmetics, cleaning agents, and the like.
  • the external preparation for skin of the present invention can be used in any dosage form that can be adapted to the skin, but since the active ingredient penetrates the skin and exerts its effect, Good dosage forms such as lotion, emulsion, cream and essence are preferred.
  • Compound 1 and Compound 2 can be synthesized, for example, according to the method described in “Basics and Experiments of Peptide Synthesis” (Maruzen Co., Ltd.). Boc-Gly (Peptide Institute, Inc.) was used as a starting material, dissolved in anhydrous N, N-dimethylformamide (Wako Pure Chemical Industries, Ltd.), sodium hydride and the corresponding alkyl halide (methyl iodide, iodide) After carrying out an alkylation reaction using ethyl, Wako Pure Chemical Industries, Ltd.), a deprotection reaction with an acid such as hydrochloric acid, and further a free base is obtained by ion exchange to obtain the desired compound 1 or compound 2. Can be obtained. Such a compound can also be purchased as a commercially available reagent from a reagent manufacturer such as Tokyo Chemical Industry Co., Ltd. In the examples of the present invention, compounds purchased from Tokyo Chemical Industry Co., Ltd. were used.
  • Example 1 Inhibition of pigmentation by ultraviolet irradiation using colored guinea pig>
  • the back skin of eight colored guinea pigs was removed and shaved with an electric clipper and shaver, and this part was covered with a black cloth with 2 x 2 cm irradiation windows on the left and right, and then the FL20S / E30 lamp was used as the light source.
  • 300 mJ / cm 2 of ultraviolet rays were irradiated. This operation was repeated on the first day, the third day, the fifth day, and the eighth day of the test to induce pigmentation at two test sites.
  • Compound 1 was dissolved in a 70% (v / v) ethanol aqueous solution to 5% (w / v) to prepare a Compound 1-containing ethanol aqueous solution.
  • a 70% (v / v) ethanol aqueous solution was prepared as a control. From the end of the ultraviolet irradiation on the first day of the test, application of the compound 1-containing ethanol aqueous solution and the ethanol aqueous solution was started. Application was performed once a day at a predetermined test site by 30 ⁇ L, and this was continuously carried out every day for 5 weeks (up to the 35th day of the test).
  • Example 2 External preparation for skin of the present invention (Lotion 1), Comparative Examples 1 and 2>
  • a cosmetic (lotion) which is an external preparation for skin of the present invention was prepared. That is, the prescription ingredients were heated to 80 ° C., stirred, dissolved, stirred and cooled to obtain a cosmetic (lotion 1).
  • the obtained lotion 1 was a uniform composition and a very stable preparation.
  • lotion 2 of Comparative Example 1 in which “pigmentation improving agent of the present invention (compound 1)” was replaced with water and arbutin were replaced with “pigmentation improving agent of the present invention (compound 1)”.
  • Lotion 3 of Comparative Example 2 was also prepared.
  • Example 3 External preparation for skin of the present invention (Cream 1)> A water-in-oil cream was prepared according to the formulation shown in Table 3. That is, the ingredients (a) and (b) were each heated to 80 ° C., and (b) was gradually added to the emulsion, emulsified, and the particles were homogenized with a homogenizer, followed by stirring and cooling to obtain a cosmetic (Cream 1). It was. The obtained cream 1 was a very stable preparation without causing separation.
  • Example 4 External preparation for skin of the present invention
  • a cosmetic milky lotion 1 which is a composition for external use of the skin of the present invention was prepared. That is, the ingredients of A, B, and C are heated to 80 ° C., and after neutralizing and adding C to B, the emulsion particles are homogenized with a homomixer. (Emulsion 1) was obtained. The obtained emulsion 1 was a very stable preparation without separation.
  • ⁇ Test Example 2 Inhibition of pigmentation by ultraviolet irradiation of lotions 1 to 3 in humans> Using the skin external preparations of Lotion 1, Lotion 2 (Comparative Example 1) and Lotion 3 (Comparative Example 2), the pigmentation inhibitory effect was examined. A panel of 1.5 cm ⁇ 1.5 cm was divided into two upper and lower tiers on the inner side of the upper arm of the panelists who participated freely. The site provided with the minimum amount of erythema (1 MED) was irradiated once a day for 3 consecutive days. From the end of the ultraviolet irradiation on the first day of the test, 50 ⁇ L of lotion was applied once a day for 35 consecutive days. One of the four sites was an untreated site.
  • erythema (1 MED)
  • the skin lightness (L * value) of each test site was measured with a color difference meter (CR-300, Konica Minolta Co., Ltd.) 24 hours after the completion of 35 times of application, and the L of the treated site relative to the L * value of the untreated site.
  • * Value difference ( ⁇ L * ) value was calculated.
  • the L * value decreases as the degree of pigmentation increases. Therefore, it can be determined that the greater the ⁇ L * value, the better the pigmentation.
  • the results are shown in Table 5. This shows that the cosmetic (lotion 1) which is an external preparation for skin of the present invention has an excellent pigmentation-suppressing effect. This is considered to be due to the pigmentation inhibitory action of Compound 1 contained in Lotion 1.
  • the present invention can be applied to skin external preparations such as whitening cosmetics.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne : un agent améliorant la pigmentation possédant un nouveau noyau mère ; et une préparation externe pour la peau qui contient ledit agent améliorant la pigmentation. L'invention concerne spécifiquement : un agent améliorant la pigmentation comprenant un composé représenté par la formule générale (1) et/ou l'un de ses sels pharmacologiquement acceptables, possédant une excellente activité améliorant la pigmentation ; et une préparation externe pour la peau pouvant être utilisée pour des objectifs visant à blanchir la peau et comprenant ledit agent améliorant la pigmentation. (Dans la formule, R1 représente un groupe alkyle linéaire ou ramifié contenant 1 à 6 atomes de carbone ; R2 représente un atome d'hydrogène ou un groupe alkyle linéaire ou ramifié contenant 1 à 4 atomes de carbone.)
PCT/JP2011/051696 2010-02-02 2011-01-28 Agent améliorant la pigmentation Ceased WO2011096330A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2011552748A JPWO2011096330A1 (ja) 2010-02-02 2011-01-28 色素沈着改善剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010021291 2010-02-02
JP2010-021291 2010-02-02

Publications (1)

Publication Number Publication Date
WO2011096330A1 true WO2011096330A1 (fr) 2011-08-11

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PCT/JP2011/051696 Ceased WO2011096330A1 (fr) 2010-02-02 2011-01-28 Agent améliorant la pigmentation

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TW (1) TW201141529A (fr)
WO (1) WO2011096330A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000063224A (ja) * 1998-08-20 2000-02-29 Kanebo Ltd 化粧料
JP2004315384A (ja) * 2003-04-14 2004-11-11 Kyowa Hakko Kogyo Co Ltd 美白剤
JP2006241102A (ja) * 2005-03-04 2006-09-14 Kanebo Cosmetics Inc Ｓｃｆ遊離抑制剤及び皮膚外用組成物
WO2007013662A1 (fr) * 2005-07-26 2007-02-01 Shiseido Company, Ltd. Agent d’amélioration/de prévention des rides
JP2008088113A (ja) * 2006-10-03 2008-04-17 Ss Pharmaceut Co Ltd 美白組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000063224A (ja) * 1998-08-20 2000-02-29 Kanebo Ltd 化粧料
JP2004315384A (ja) * 2003-04-14 2004-11-11 Kyowa Hakko Kogyo Co Ltd 美白剤
JP2006241102A (ja) * 2005-03-04 2006-09-14 Kanebo Cosmetics Inc Ｓｃｆ遊離抑制剤及び皮膚外用組成物
WO2007013662A1 (fr) * 2005-07-26 2007-02-01 Shiseido Company, Ltd. Agent d’amélioration/de prévention des rides
JP2008088113A (ja) * 2006-10-03 2008-04-17 Ss Pharmaceut Co Ltd 美白組成物

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JPWO2011096330A1 (ja) 2013-06-10
TW201141529A (en) 2011-12-01

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