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AU2001243334A1 - Inhibitors of melanocyte tyrosinase as topical skin lighteners - Google Patents

Inhibitors of melanocyte tyrosinase as topical skin lighteners

Info

Publication number
AU2001243334A1
AU2001243334A1 AU2001243334A AU4333401A AU2001243334A1 AU 2001243334 A1 AU2001243334 A1 AU 2001243334A1 AU 2001243334 A AU2001243334 A AU 2001243334A AU 4333401 A AU4333401 A AU 4333401A AU 2001243334 A1 AU2001243334 A1 AU 2001243334A1
Authority
AU
Australia
Prior art keywords
inhibitors
skin
topical skin
compounds
methods
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.)
Abandoned
Application number
AU2001243334A
Inventor
Ernest V. Curto
Thomas P. Dooley
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.)
IntegriDerm Inc
Original Assignee
IntegriDerm 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 IntegriDerm Inc filed Critical IntegriDerm Inc
Publication of AU2001243334A1 publication Critical patent/AU2001243334A1/en
Abandoned legal-status Critical Current

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
    • A61Q19/02—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
    • A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
    • 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
    • A61K31/13—Amines
    • A61K31/145—Amines having sulfur, e.g. thiurams (>N—C(S)—S—C(S)—N< and >N—C(S)—S—S—C(S)—N<), Sulfinylamines (—N=SO), Sulfonylamines (—N=SO2)
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
    • 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
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/428—Thiazoles condensed with carbocyclic rings
    • 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
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Pain & Pain Management (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Methods and formulations are provided to reduce pigmentation in skin, using an array of compounds selected from benzimidazoles, phenylthioureas, phenyltiols, phenylamines, bi- and multicyclic phenols, thiopheneamines, and benzothiamides. The compounds preferably inhibit pigment systhesis in melanocytes through the tyrosinase pathway. The methods can be used for lightening skin, and for treating uneven skin complexions which result from hyperpigmentation-related medical conditions such as melasma, age spots, freckles, ochronosis, and lentigo. The compounds can be used medically or cosmetically.
AU2001243334A 2000-02-29 2001-02-28 Inhibitors of melanocyte tyrosinase as topical skin lighteners Abandoned AU2001243334A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US18561000P 2000-02-29 2000-02-29
US60/185,610 2000-02-29
PCT/US2001/006434 WO2001064206A2 (en) 2000-02-29 2001-02-28 Inhibitors of melanocyte tyrosinase as topical skin lighteners

Publications (1)

Publication Number Publication Date
AU2001243334A1 true AU2001243334A1 (en) 2001-09-12

Family

ID=22681701

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2001243334A Abandoned AU2001243334A1 (en) 2000-02-29 2001-02-28 Inhibitors of melanocyte tyrosinase as topical skin lighteners

Country Status (8)

Country Link
US (5) US20020044914A1 (en)
EP (2) EP1267868B1 (en)
AT (2) ATE481967T1 (en)
AU (1) AU2001243334A1 (en)
CA (1) CA2401336C (en)
DE (2) DE60129420T2 (en)
ES (1) ES2352974T3 (en)
WO (1) WO2001064206A2 (en)

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US20030199558A1 (en) * 2001-12-28 2003-10-23 Integriderm, Inc. Hydroxamic acid and its derivatives as inhibitors of melanocyte tyrosinase for topical skin lighteners
FR2845599B1 (en) * 2002-10-11 2005-01-07 Lmd MEDICAMENT COMPRISING A THIOUREE FOR ITS USE AS A DEPIGMENTING
DE10252772A1 (en) * 2002-11-13 2004-05-27 Beiersdorf Ag Cosmetic or dermatological composition used for treating e.g. against skin sensitivity, inflammation, psoriasis, pruritis and dandruff contains diethyl dithiocarbamate
PT1701940E (en) * 2003-12-23 2008-07-30 Lundbeck & Co As H 2-(1h-indolylsulfanyl)-benzyl amine derivatives as ssri
MXPA06013705A (en) 2004-05-28 2007-02-13 Unigen Pharmaceuticals Inc Diarylalkanes as potent inhibitors of binuclear enzymes.
AR052308A1 (en) * 2004-07-16 2007-03-14 Lundbeck & Co As H DERIVATIVES OF 2- (1H-INDOLILSULFANIL) -ARILAMINE AND A PHARMACEUTICAL COMPOSITION CONTAINING THE COMPOUND
FR2877672B1 (en) * 2004-11-10 2007-04-13 Oreal USE OF UTP TO PROMOTE IN VITRO CULTIVATION OF MELANOCYTES, PARTICULARLY HIGHLY PIGMENTED MELANOCYTES
FR2880022B1 (en) * 2004-12-24 2007-08-24 Mayoly Spindler Soc Par Action NOVEL DERIVATIVES OF N-HYDROXY-N'-PHENYLUREE AND N-HYDROXY-N'-PHENYLTHIOUREE AND THEIR USE AS INHIBITORS OF MELANIN SYNTHESIS
DE102005022292A1 (en) * 2005-05-13 2006-11-16 Basf Ag Use of sulfur containing compound, as a peroxide composite, in cosmetic and pharmaceutical agent to treat skin
AR054393A1 (en) * 2005-06-17 2007-06-20 Lundbeck & Co As H DERIVATIVES OF BENZO (B) FURANO AND BENZO (B) THIOPHEN, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USE IN THE MANUFACTURE OF A MEDICINAL PRODUCT FOR THE TREATMENT OF DISEASES MEDIATED BY THE INHIBITION OF THE REINFORCEMENT OF AMINA BOSS NEUTRANTS.
US7629473B2 (en) * 2005-06-17 2009-12-08 H. Lundbeck A/S 2-(1H-indolylsulfanyl)-aryl amine derivatives
FR2890070A1 (en) * 2005-08-31 2007-03-02 Galderma Res & Dev New imidazole compounds are tyrosinase inhibitors useful to treat e.g. melasma, chloasma, lentigines, senile lentigo, and vitiligo, and to prevent and/or treat the signs of ageing
WO2007039821A2 (en) * 2005-08-31 2007-04-12 Galderma Research & Development Novel inhibitors of tyrosinase, their method of preparation and their use in human medicine and in cosmetics
KR100788161B1 (en) 2006-01-06 2007-12-21 (주)아모레퍼시픽 Skin whitening composition containing benzimidazole amine derivative or aminoquinoline derivative
US20080070982A1 (en) * 2006-09-15 2008-03-20 Graham Timmins System and methods of melanoma prevention
EP3542780B1 (en) 2008-07-21 2022-01-19 Unigen, Inc. Series of skin-whitening (lightening) compounds
EP2193779A1 (en) * 2008-12-05 2010-06-09 Cognis IP Management GmbH Skin whitener
RU2011143735A (en) 2009-03-31 2013-05-10 Сисеидо Компани, Лтд. MEANS FOR SKIN WHITENING AND COSMETIC METHOD FOR WHITENING SKIN
KR101246682B1 (en) * 2010-02-23 2013-04-01 충북대학교 산학협력단 Composition for whitening of the skin comprising arylthiourea derivatives
FR2958845B1 (en) * 2010-04-16 2012-06-01 Clc Technologie NEW DEPIGMENTING COMPOSITIONS
WO2011137456A2 (en) * 2010-04-30 2011-11-03 Hampton University Methods and mechanisms involving hyperpigmentation particularly for african american skin
US8293218B2 (en) 2010-07-29 2012-10-23 Conopco, Inc. Skin care compositions comprising substituted monoamines
US8476251B2 (en) * 2010-07-29 2013-07-02 Conopco, Inc. Skin care compositions comprising substituted diamines
KR101976642B1 (en) 2011-03-24 2019-05-09 유니젠, 인크. Compounds and methods for preparation of diarylpropanes
US20130273183A1 (en) * 2012-04-13 2013-10-17 Eastman Chemical Company 2-Pyrimidine Thioesters and Thiocarbonates as Skin Brightening Agents
WO2014164195A1 (en) 2013-03-13 2014-10-09 Avon Products, Inc Tyrosinase inhibitors
US20150174034A1 (en) * 2013-03-13 2015-06-25 Avon Products, Inc. Tyrosinase inhibitors
US9717722B2 (en) 2013-05-13 2017-08-01 New York University Methods and agents for treating tyrosinase-positive albinism
EP3484528B1 (en) 2016-07-18 2020-11-25 Janssen Pharmaceutica NV Tau pet imaging ligands
MX380436B (en) 2016-09-06 2025-03-12 Unilever Ip Holdings B V COMPOUNDS TO REDUCE CELLULAR MELANIN CONTENT.
CN109180587A (en) * 2018-09-20 2019-01-11 五邑大学 A kind of new application of pyrazole analogs
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KR102543627B1 (en) * 2021-01-22 2023-06-20 한국과학기술연구원 Skin whitening composition containing 2,4-Dimethylphenylthiourea
US20240122834A1 (en) 2021-02-12 2024-04-18 Symrise Ag Medicament for prevention and treatment of hyperpigmentation
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JP3545097B2 (en) * 1995-04-19 2004-07-21 御木本製薬株式会社 Skin cosmetics
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FR2770522B1 (en) * 1997-11-04 2000-03-10 Oreal COMPOUNDS COMPRISING AN IMINOPHENOL FRAGMENT AND THEIR USE IN COSMETICS

Also Published As

Publication number Publication date
EP1857109A2 (en) 2007-11-21
WO2001064206A3 (en) 2002-08-29
WO2001064206A2 (en) 2001-09-07
US7718185B2 (en) 2010-05-18
US20090023793A1 (en) 2009-01-22
EP1267868A2 (en) 2003-01-02
EP1267868B1 (en) 2007-07-18
ES2352974T3 (en) 2011-02-24
EP1857109B1 (en) 2010-09-22
US20020044914A1 (en) 2002-04-18
DE60129420T2 (en) 2008-04-03
US20030219393A1 (en) 2003-11-27
EP1857109A3 (en) 2008-03-19
ATE367157T1 (en) 2007-08-15
US20090023792A1 (en) 2009-01-22
US7858105B2 (en) 2010-12-28
CA2401336C (en) 2014-12-23
DE60129420D1 (en) 2007-08-30
DE60143135D1 (en) 2010-11-04
ATE481967T1 (en) 2010-10-15
CA2401336A1 (en) 2001-09-07
US20050152859A1 (en) 2005-07-14

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