WO1998042308A1 - Agents de prevention du vieillissement de la peau - Google Patents

Agents de prevention du vieillissement de la peau Download PDF

Info

Publication number
WO1998042308A1
WO1998042308A1 PCT/JP1998/001143 JP9801143W WO9842308A1 WO 1998042308 A1 WO1998042308 A1 WO 1998042308A1 JP 9801143 W JP9801143 W JP 9801143W WO 9842308 A1 WO9842308 A1 WO 9842308A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
agent
skin aging
skin
preventing
Prior art date
Application number
PCT/JP1998/001143
Other languages
English (en)
Japanese (ja)
Inventor
Naoko Tsuji
Shigeru Moriwaki
Genji Imokawa
Yasuto Suzuki
Yoshinori Nishizawa
Original Assignee
Kao Corporation
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 claimed from JP7169897A external-priority patent/JPH10265359A/ja
Priority claimed from JP07170097A external-priority patent/JP3688846B2/ja
Application filed by Kao Corporation filed Critical Kao Corporation
Publication of WO1998042308A1 publication Critical patent/WO1998042308A1/fr

Links

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
    • A61Q19/08—Anti-ageing preparations
    • 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
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur

Definitions

  • the present invention relates to a preventive agent for skin aging, and more particularly to a preventive agent for skin aging which can prevent or improve appearance changes such as wrinkles and sagging caused by skin aging.
  • an object of the present invention is to provide a drug or cosmetic which can prevent or improve symptoms caused by skin aging represented by wrinkles. Disclosure of the invention
  • the present inventors have proposed specific phosphonic acid derivatives (Japanese Patent Application Laid-Open No. 5-165898) which have heretofore been known as a therapeutic agent for hypertension, a therapeutic agent for heart and cerebral circulatory diseases, a therapeutic agent for renal diseases and the like. Attention was paid to a specific mercaptopropionamide derivative known as a collagenase inhibitor (Japanese Patent Application Laid-Open No. 57-244354). And surprisingly these It has been found that compounds and salts thereof can prevent and improve symptoms caused by skin aging represented by wrinkles. Further, they have found that an inhibitor of metal-dependent elastin-degrading enzyme is effective in preventing wrinkle formation, and that the mercaptopropionamide derivative and its salt effectively inhibit the metal-dependent elastin-degrading enzyme. Completed.
  • R 1 , R 2 and R 3 represent a hydrogen atom, a hydrocarbon group which may have a substituent or a sugar residue which may have a substituent
  • R 4 represents a hydrogen atom or an acyl group
  • R 5 represents a hydrogen atom or a hydrocarbon group which may have a substituent
  • R 6 represents a hydrogen atom, a carboxyl group, an alkoxycarbonyl group
  • n represents a number of 1 to 20
  • the present invention also provides a metal-dependent elastin-degrading enzyme inhibitor containing the mercaptopropionamide derivative or a salt thereof as an active ingredient, and a wrinkle-preventing agent containing the metal-dependent elastin-degrading enzyme inhibitor as an active ingredient. It is. BEST MODE FOR CARRYING OUT THE INVENTION
  • the hydrocarbon group which may have a substituent represented by R 1 , R 2 , R 3 , R 5 and R 6 is a saturated hydrocarbon group or an unsaturated hydrocarbon group.
  • Any of a hydrogen group may be used, and examples thereof include an alkyl group, an alkenyl group, an alkynyl group, a cyclic alkyl group, a cyclic alkenyl group, an aromatic hydrocarbon group, and an aralkyl group.
  • These hydrocarbon groups preferably have 1 to 24 carbon atoms, particularly preferably 1 to 18 carbon atoms.
  • an alkyl group, a cyclic alkyl group, an aromatic hydrocarbon group or an aralkyl group is preferred.
  • the alkyl group is preferably a linear or branched alkyl group having 1 to 12 carbon atoms, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isoamyl group, tert-amyl group, n-hexyl group, n-octyl group, n-decyl group, n-dodecyl group and the like.
  • the cyclic alkyl group is preferably a 5- to 7-membered alicyclic alkyl group, and examples thereof include a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • the aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 14 carbon atoms, such as a phenyl group and a naphthyl group.
  • Examples of the group which can be substituted for these hydrocarbon groups include a halogen atom, a hydroxyl group, an alkoxyl group, an acyl group, an amino group which may be protected, and a heterocyclic group.
  • the halogen atom includes a chlorine atom, a bromine atom, an iodine atom and the like.
  • the alkoxyl group is preferably an alkoxyl group having 1 to 12 carbon atoms, such as a methoxy group, an ethoxy group, and an isopropoxy group.
  • the sacyl group has the carbon number
  • An alkanol group of 1 to 12 is preferable, and examples thereof include an acetyl group, a propionyl group, and a butyryl group.
  • Examples of the amino group which may be protected include an amino group, an acylamino group, an alkylamino group and a dialkylamino group.
  • the heterocyclic group is preferably a 5- to 14-membered monocyclic or condensed ring group having 1 to 3 nitrogen atoms, oxygen atoms and / or sulfur atoms as hetero atoms, such as a pyridyl group, a pyridazinyl group, and a furyl group. Phenyl, thienyl, indolyl, thiazolyl, imidabryl, benzofuryl, benzochenyl and the like.
  • the sugar residues represented by R 1 , R 2 and R 3 include a monosaccharide residue or an oligosaccharide residue.
  • Examples of the group that can be substituted for these sugar residues include an alkyl group, an acyl group, and an aralkyl group.
  • the alkyl group, the acyl group, and the aralkyl group are the same as those described above.
  • the acyl group represented by R 4 and R 6 includes an alkanoyl group and an arylcarbonyl group.
  • the alkanoyl group is preferably an alkanoyl group having 1 to 12 carbon atoms, and examples thereof include an acetyl group, a propionyl group and a petyryl group.
  • the arylcarbonyl group is preferably an arylcarbonyl group having 7 to 15 carbon atoms, and examples thereof include a benzoyl group, a substituted benzoyl group, a naphthylcarbonyl group, and a substituted naphthylcarbonyl group.
  • the group substituted with a benzoyl group or a naphthylcarbonyl group includes an alkyl group, an alkoxy group, a halogen group, an amino group, a hydroxy group, and a alkanoyloxy group.
  • the heterocyclic group represented by R 6 is preferably a 5- to 14-membered monocyclic or condensed ring group having 1 to 3 nitrogen atoms, oxygen atoms and Z or sulfur atoms as a hetero atom, for example, pyridyl Groups, pyridazinyl group, furylic acid, chenyl group, indolyl group, thiazolyl group, imidazolyl group, benzofuryl group, benzochelyl group, pyrrolidinyl group, piperidinyl group, perforinyl group, and piperazinyl group.
  • Examples of the group that can be substituted for the complex cyclic group include a halogen atom, a hydroxyl group, an alkoxyl group, an acyl group, and an amino group which may be protected. Components of these substituents Examples of the substituent include the same substituents as those described above for the hydrocarbon group for R 5 and R 8 .
  • the alkoxycarbonyl group represented by R 6 includes an alkoxycarbonyl group having 1 to 12 carbon atoms, and specific examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, and a butoxycarbonyl group. . n represents a number of 1 to 20, preferably 1 to 10, and particularly preferably 2.
  • phosphonic acid derivatives (1) include the following compounds.
  • Examples of the salts of the phosphonic acid derivative (1) include sodium salts and alkali salts of potassium salts. Examples thereof include alkaline earth metal salts such as metal salts, calcium salts, and magnesium salts, ammonium salts, and alkylamine salts.
  • the phosphonic acid derivative (1) can also be used as a hydrate.
  • mercaptopropionamide derivative (2) examples include the following compounds.
  • Examples of the salt of the mercaptopropionamide derivative (2) include inorganic acid salts such as hydrochloride and sulfate, and organic acid salts such as acetate.
  • the mercaptopropionamide derivative (2) can also be used as a hydrate.
  • the phosphonic acid derivative (1) or a salt thereof can be produced, for example, by the method described in JP-A-5-105988.
  • mercaptopropionamide derivatives (2) can be produced, for example, by the method described in JP-A-57-243554.
  • the agent for preventing skin aging of the present invention has a preventive or ameliorating effect on morphological changes caused by aging of the skin, such as wrinkles and sagging.
  • the action is excellent.
  • the agent for preventing wrinkle formation of the present invention contains an inhibitor for metal-dependent elastin-degrading enzyme as an active ingredient.
  • the metal-dependent elastin-degrading enzyme inhibitor used in the wrinkle formation preventive agent of the present invention is preferably a metal-dependent elastase inhibitor, particularly a metal-dependent elastase inhibitor derived from dermal fibroblasts.
  • a metal-dependent elastase inhibitor derived from dermal fibroblasts.
  • Such an inhibitor can be prepared, for example, by using an enzyme solution extracted from cultured human fibroblasts with 0.1% Triton X-100Z0.2M Tris-HCl buffer (pH 8.0).
  • Examples of such metal-dependent elastin-degrading enzyme inhibitors include, for example, the above-mentioned phosphonic acid derivative (1), mercaptopropionamide derivative (2), and salts thereof. Among them, mercaptoamide derivatives and salts thereof are particularly preferred.
  • Examples of the dosage form of the preventive agent for preventing skin aging or wrinkle formation of the present invention include an external preparation for the skin and an oral preparation. The external preparation for the skin is preferable.
  • the amount of the phosphonic acid derivative (1), the mercaptopropionamide derivative (1) or a salt thereof when used as an external preparation for skin is not particularly limited, but is 0.0000 to the total composition. It is preferably from 10 to 10% by weight, particularly preferably from 0.001 to 5% by weight.
  • the skin aging preventive agent and the wrinkle preventive agent of the present invention include, in addition to the phosphonic acid derivative (1), the mercaptopropionamide derivative or a salt thereof, and a metal-dependent elastin-degrading enzyme inhibitor, an ultraviolet absorber, an ultraviolet light protector.
  • Ingredients, collagen, moisturizing agents, anti-inflammatory agents, antioxidants and the like can be blended, but it is particularly preferable to blend a UV absorber and a UV absorber.
  • examples of the ultraviolet absorbent include 2-ethylhexyl p-methoxycinnamate, 4-t-butyl-4'-methoxydibenzoylmethane, and the like.
  • examples of the ultraviolet protective agent include titanium oxide and zinc oxide.
  • examples of the humectant include hyaluronic acid and ceramides.
  • examples of the anti-inflammatory agent include allantoin, glycyrrhizin and the like.
  • Specific dosage forms of the skin aging preventive agent of the present invention include creams, ointments, gels, mouth lotions, solutions, tablets, foundations, and the like.
  • Various oils, surfactants, gelling agents, preservatives, antioxidants, solvents, alcohols, A chelating agent, a thickener, a coloring matter, a fragrance, water and the like can be added.
  • the suspension was suspended in 100 / 0.2 ⁇ Tris-HCl buffer ( ⁇ 8.0) and sonicated to obtain an enzyme solution.
  • compound 6 which is known as a neutrophil-derived serine protease elastase inhibitor, inhibits the enzyme derived from human fibroblasts, a metal-dependent elastase. No effect was shown. In contrast, compounds 1, 5, and 2 strongly inhibited metal-dependent elastase.
  • the skin elasticity was measured using Cuteme Ichiichi SES 575 (manufactured by Kleige Kazarik), aspirated at 50 Omb for 3 seconds, released, and then measured displacement for 3 seconds for a total of 6 seconds. Specified. The measurement was performed five times for each sole, and Ue (instantaneous elastic displacement) and Uf (final displacement) values were obtained. The Ue value is an index of elasticity, and the Uf value is an index of flexibility. Table 3 shows the results. Table 3
  • Vitamin E 0.5 Ceramic 5 Fragrance trace pigment
  • the skin aging preventive agent, wrinkle preventive agent and metal-dependent elastin degrading enzyme inhibitor of the present invention can be industrially mass-produced and can be used in the cosmetics industry, etc.
  • the contents described in Japanese Patent Application Nos. 9-171698, 917169, and 917700 are incorporated herein by reference.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

Agents servant à prévenir le vieillissement de la peau, ce qui permet d'empêcher ou d'atténuer les modifications d'aspect provoquées par le vieillissement de la peau, par exemple, l'apparition de rides ou de poches ou le relâchement de la tonicité de la peau. Plus particulièrement, agents servant à prévenir le vieillissement de la peau et contenant des dérivés d'acide phosphonique représentés par la formule suivante (1), dans laquelle R?1, R2 et R3¿ représentent chacun hydrogène, etc.; ou dérivés de mercaptopropionamide représentés par la formule suivante (2) dans laquelle R?4, R5 et R6¿ représentent chacun hydrogène, etc.; ou leurs sels, permettant d'empêcher efficacement l'apparition de rides et le relâchement de la tonicité de la peau qui ne peuvent être suffisamment prévenus au moyen des méthodes classiques.
PCT/JP1998/001143 1997-03-25 1998-03-18 Agents de prevention du vieillissement de la peau WO1998042308A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP7169897A JPH10265359A (ja) 1997-03-25 1997-03-25 しわ形成予防剤
JP9/71698 1997-03-25
JP7169997 1997-03-25
JP9/71700 1997-03-25
JP9/71699 1997-03-25
JP07170097A JP3688846B2 (ja) 1997-03-25 1997-03-25 皮膚老化予防剤

Publications (1)

Publication Number Publication Date
WO1998042308A1 true WO1998042308A1 (fr) 1998-10-01

Family

ID=27300731

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1998/001143 WO1998042308A1 (fr) 1997-03-25 1998-03-18 Agents de prevention du vieillissement de la peau

Country Status (1)

Country Link
WO (1) WO1998042308A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3026299A1 (fr) * 2014-09-30 2016-04-01 Oreal Procede cosmetique pour attenuer les rides

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5724354A (en) * 1980-05-30 1982-02-08 Squibb & Sons Inc N-substituted mercaptoacylpropionamides
JPH05105698A (ja) * 1991-06-13 1993-04-27 Takeda Chem Ind Ltd ホスホン酸誘導体、その製造法および用途
JPH05168493A (ja) * 1991-11-29 1993-07-02 Sumitomo Chem Co Ltd 緑膿菌エラスターゼに対するモノクローナル抗体
JPH06345636A (ja) * 1993-06-08 1994-12-20 Nonogawa Shoji Kk 化粧料
JPH07309740A (ja) * 1993-12-30 1995-11-28 L'oreal Sa 皮膚の表層と深層とに同時に作用する対老化組成物およびその用途並びに老化処置の方法
JPH08507506A (ja) * 1993-03-05 1996-08-13 グループ・セルベール・ソシエテ・アノニム コラゲナーゼ活性阻害剤とそのような阻害剤を含む化粧品組成
WO1996028008A2 (fr) * 1996-03-19 1996-09-19 Guerlain S.A. Compositions cosmetiques et dermatologiques pour lutter contre le vieillissement de la peau
JPH08283122A (ja) * 1995-04-12 1996-10-29 Kao Corp 皮膚化粧料
JPH0920639A (ja) * 1995-07-07 1997-01-21 Shiseido Co Ltd 抗老化皮膚外用剤、コラーゲン架橋阻害皮膚外用剤及び抗紫外線皮膚外用剤
JPH0940540A (ja) * 1995-07-28 1997-02-10 Noevir Co Ltd 紫外線吸収剤及びこれを配合して成る皮膚外用剤
US5614489A (en) * 1995-05-25 1997-03-25 Mohammadi; Fatemeh Method and composition for treating the skin

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5724354A (en) * 1980-05-30 1982-02-08 Squibb & Sons Inc N-substituted mercaptoacylpropionamides
JPH05105698A (ja) * 1991-06-13 1993-04-27 Takeda Chem Ind Ltd ホスホン酸誘導体、その製造法および用途
JPH05168493A (ja) * 1991-11-29 1993-07-02 Sumitomo Chem Co Ltd 緑膿菌エラスターゼに対するモノクローナル抗体
JPH08507506A (ja) * 1993-03-05 1996-08-13 グループ・セルベール・ソシエテ・アノニム コラゲナーゼ活性阻害剤とそのような阻害剤を含む化粧品組成
JPH06345636A (ja) * 1993-06-08 1994-12-20 Nonogawa Shoji Kk 化粧料
JPH07309740A (ja) * 1993-12-30 1995-11-28 L'oreal Sa 皮膚の表層と深層とに同時に作用する対老化組成物およびその用途並びに老化処置の方法
JPH08283122A (ja) * 1995-04-12 1996-10-29 Kao Corp 皮膚化粧料
US5614489A (en) * 1995-05-25 1997-03-25 Mohammadi; Fatemeh Method and composition for treating the skin
JPH0920639A (ja) * 1995-07-07 1997-01-21 Shiseido Co Ltd 抗老化皮膚外用剤、コラーゲン架橋阻害皮膚外用剤及び抗紫外線皮膚外用剤
JPH0940540A (ja) * 1995-07-28 1997-02-10 Noevir Co Ltd 紫外線吸収剤及びこれを配合して成る皮膚外用剤
WO1996028008A2 (fr) * 1996-03-19 1996-09-19 Guerlain S.A. Compositions cosmetiques et dermatologiques pour lutter contre le vieillissement de la peau

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
ARMENGOL R., ET AL.: "ANTI-ELASTASE ACTIVITY AND REFIRMING PROPERTIES OF A PLANT COMPLEX.", SOFW-JOURNAL SEIFEN, OELE, FETTE, WACHSE., VERLAG FUR CHEMISCHE INDUSTRIE, AUGSBURG., DE, vol. 123., no. 13., 1 January 1997 (1997-01-01), DE, pages 890 + 892 + 894/895., XP002910943, ISSN: 0942-7694 *
BURNS F. R., ET AL.: "INHIBITION OF PSEUDOMONAS AERUGINOSA ELASTASE AND PSEUDOMONAS KERATITIS USING A THIOL-BASED PEPTIDE.", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, AMERICAN SOCIETY FOR MICROBIOLOGY, US, vol. 34., no. 11., 1 November 1990 (1990-11-01), US, pages 2065 - 2069., XP002910945, ISSN: 0066-4804 *
KESSLER E., ET AL.: "IN VITRO INHIBITION OF PSEUDOMONAS AERUGINOSA ELASTASE BY METAL-CHELATING PEPTIDE DERIVATIVES.", INFECTION AND IMMUNITY, AMERICAN SOCIETY FOR MICROBIOLOGY., US, vol. 38., no. 02., 1 November 1982 (1982-11-01), US, pages 716 - 723., XP002910942, ISSN: 0019-9567 *
MEKIDECHE N., ET AL.: "AOSAINE A MARINE ELASTASE INHIBITOR AND SUBSTITUTE OF ELASTIN AGAINST SKIN AGEING.", SOFW-JOURNAL SEIFEN, OELE, FETTE, WACHSE., VERLAG FUR CHEMISCHE INDUSTRIE, AUGSBURG., DE, vol. 120., no. 01., 1 January 1994 (1994-01-01), DE, pages 20 - 22., XP002910944, ISSN: 0942-7694 *
MORIHARA K., ET AL.: "PHOSPHORAMIDON AS AN INHIBITOR OF ELASTASE FROM PSEUDOMONAS AERUGINOSA.", JAPANESE JOURNAL OF EXPERIMENTAL MEDICINE., INSTITUTE OF MEDICAL SCIENCE, TOKYO., JP, vol. 48., no. 01., 1 January 1978 (1978-01-01), JP, pages 81 - 84., XP002910941, ISSN: 0021-5031 *
PONCZ L., ET AL.: "INHIBITION OF THE ELASTASE OF PSEUDOMONAS AERUGINOSA BY NALPHA-PHOSPHORYL DIPEPTIDES AND KINETICS OF SPONTANEOUS HYDROLYSIS OF THE INHIBITORS.", BIOCHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 23., no. 12., 1 January 1984 (1984-01-01), US, pages 2766 - 2772., XP002910940, ISSN: 0006-2960, DOI: 10.1021/bi00307a036 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3026299A1 (fr) * 2014-09-30 2016-04-01 Oreal Procede cosmetique pour attenuer les rides
WO2016050788A1 (fr) * 2014-09-30 2016-04-07 L'oreal Procédé cosmétique pour atténuer les rides

Similar Documents

Publication Publication Date Title
JP4427901B2 (ja) シスチン誘導体の用途
US20060093567A1 (en) Method of inhibiting hair growth
EP3431081B1 (fr) Composition anti-âge
EP2229138B1 (fr) Compositions topiques comprenant des acides aminés non protéogéniques et procédés de traitement de la peau
EP1889642B1 (fr) Compositions cosmétiques associant un dérivé C-glycoside et un dérivé N-acylaminoamide
EP4299077A2 (fr) Compositions et procédés d'amélioration de la peau
CA2391585A1 (fr) Composition cosmetique ou dermatologique comprenant une association entre un compose de la famille des n-acylaminoamides et au moins un inhibiteur de metalloproteinases matricielles
US6056944A (en) Pharmaceutical compositions for oral use including an NSAID and ceramides
JP2006022090A (ja) ピロリドンカルボン酸亜鉛塩から成る炎症抑制剤
US20040191203A1 (en) Cosmetic or dermatological composition comprising n-acylaminoamide derivatives
WO1998042308A1 (fr) Agents de prevention du vieillissement de la peau
JP3898328B2 (ja) 皮膚老化予防剤
JP4340649B2 (ja) しわ形成予防剤
KR20110097576A (ko) 벤즈알데하이드 티오세미카바존 유도체를 함유한 미백용 조성물
WO2021145699A1 (fr) Composition pour le traitement de maladies de la peau, comprenant de la colchicine
JPH10265359A (ja) しわ形成予防剤
JPH05222015A (ja) チアゾール類縁化合物及び皮膚外用剤
US7375085B1 (en) Melanocyte-stimulating hormone inhibitors
JPH10265360A (ja) 皮膚老化予防剤
JP2005206609A (ja) 皮膚老化予防剤
JP2000178163A (ja) 皮膚外用剤
JPH07242542A (ja) 化粧料
JP2001114664A (ja) 化粧料
JP2014172868A (ja) 皮膚光老化の予防又は抑制剤
KR101526592B1 (ko) 피부주름 개선용 조성물

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase