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WO2001066105A1 - Procede et composition pour eclaircir la peau - Google Patents

Procede et composition pour eclaircir la peau Download PDF

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Publication number
WO2001066105A1
WO2001066105A1 PCT/US2001/007182 US0107182W WO0166105A1 WO 2001066105 A1 WO2001066105 A1 WO 2001066105A1 US 0107182 W US0107182 W US 0107182W WO 0166105 A1 WO0166105 A1 WO 0166105A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
composition
hydroxy
derivatives
present
Prior art date
Application number
PCT/US2001/007182
Other languages
English (en)
Inventor
John E. Kuleza
Original Assignee
Young Pharmaceuticals, 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 Young Pharmaceuticals, Inc. filed Critical Young Pharmaceuticals, Inc.
Priority to AU2001245474A priority Critical patent/AU2001245474A1/en
Publication of WO2001066105A1 publication Critical patent/WO2001066105A1/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
    • A61Q19/02—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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C

Definitions

  • This invention relates to a method and composition for lightening skin color.
  • Melanin is a pigment found in the skin which plays a key role in protecting the body from ultraviolet radiation. Melanin is produced in the form of granules called melanosomes within a type of cell called a melanocyte. Melanosomes are transferred to a layer of keratin-producing cells near the outer surface of the skin known as keratinocytes. The greater the number of melanosomes transferred to keratmocytes, the darker the skin appears. Occasionally alterations occur in this process whereby excessive darkening of the skin is observed.
  • hyperpigmentation can be associated with freckles, senile lentigo, lentigines, pregnancy, melasma, chloasma, post- inflammatory hyperpigmentation, sunburn, phototoxic reactions, and other conditions. While not usually life-threatening, hyperpigmentation is viewed as cosmetically undesirable and psychologically debilitating.
  • the only treatment approved for lightening the skin in the United States is topical application of 1,4 benzenediol, also known as hydroquinone, which acts by reducing the number of melanosomes produced by melanocytes. Hydroquinone is sold in concentrations up to 2% without prescription, and in concentrations of 3-4% by prescription.
  • Hydroquinone preparations can cause side effects ranging from skin redness, burning and sensitization to paradoxical effects such as skin darkening.
  • There is a need for new treatments for hyperpigmentation which are at least as effective as hydroquinone but are hydroquinone-free.
  • a method for lightening the skin comprises applying to hyperpigmented areas of the skin a composition which includes: (1) Kojic acid and/or derivatives thereof, (2) an anti-oxidant and (3) a hydroxy acid and/or derivatives thereof.
  • a composition for lightening the skin is also provided which includes: (1) Kojic acid and/or derivatives thereof, (2) an anti-oxidant and (3) a hydroxy acid and/or derivatives thereof.
  • Kojic acid is a well known and commercially-available compound. Dermally-available derivatives of Kojic acid may also be used, such as Kojic dipalmitate. A dermally-available derivative of Kojic acid is a compound that makes Kojic acid or a biologically active form of Kojic acid available in the skin.
  • Kojic acid and/or derivatives thereof may be employed in the composition in the range of about 1 to 25% w/w, and preferably between 2 and 10% w/w.
  • Anti-oxidants for use in the invention may include ascorbic acid (vitamin C) and/or derivatives thereof, especially Magnesium ascorbal phosphate; tocopherol (vitamin E), Tocopherol acetate, other esters thereof; butylated hydroxy benzoic acids and their salts; 6-hydroxy-2,5,7,8 tetramethylchroman-2- carboxylic acid (commercially available under the trademark TROLOX); gallic acid and its alkyl esters, especially propyl gallate; uric acid and its salts and alkyl esters; sorbic acid and its salts, the ascorbyl esters of fatty acids; amines, such as N,N-diethylhydroxylamine and amino-guanidine; sulfhydryl compounds, such as glutathione and N-acetyl cysteine; and dihydroxy fumaric acid and its salts.
  • ascorbic acid vitamin C
  • vitamin E tocopherol
  • acetate other esters thereof
  • anti-oxidants may be used alone or in combination.
  • the anti-oxidant component may be employed in the composition in a concentration sufficient to exhibit anti- oxidant activity in vivo; for example, in the case of ascorbic acid or magnesium ascorbyl phosphate, concentration range of about 1 to 25% should be employed, preferably between 5 and 10% w/w.
  • Hydroxy acids for use in the invention encompass the general class of organic compounds containing at least one hydroxy group and at least one carboxyl group, wherein at least one hydroxyl group is located on the alpha- or beta-carbon atom.
  • the hydroxy acid will have a single hydroxyl group (other than that associated with a carboxyl moiety), on the alpha-carbon atom, and may contain one, two or three carboxyl groups.
  • these compounds will have a basic structure of lower aliphatic compounds having from two to six carbon atoms.
  • the derivatives of these hydroxy acids most typically will involve derivatives related to carboxyl functionality, i.e., wherein the hydroxy or hydroxyl portion of the carboxyl moiety is substituted by metallic ions (to form salts), alkoxy groupings (to form esters), ammonium ions (to form ammonium salts), as well as other substitution reactions and products leading to formation of corresponding lactones, anhydrides or amides.
  • the derivatives may also include reactions involving the alpha-hydroxyl group, most notably ketone formation, to form corresponding alpha-keto carboxyl acids.
  • hydroxy acids and derivative compounds useful in the present invention are glycolic acid, glucuronic acid, galacturonic acid, gluconic acid, glucoheptonic acid, -hydroxybutyric acid, -hydroxyisobutyric acid, - hydroxyisocaproic acid, -hydroxyisovaleric acid, lactic acid, malic acid, muric acid, citric acid, saccharic acid, tartaric acid, tartronic acid, isocitric acid, dihydroxymaleic acid, dihydroxytartaric acid and dihydroxyfumaric acid.
  • keto acids and keto esters such as pyruvic acid, methyl pyruvate, ethyl pyruvate, isopropyl pyruvate, benzoylformic acid, methyl benzoylformate and ethyl benzoylformate.
  • keto acids and keto esters such as pyruvic acid, methyl pyruvate, ethyl pyruvate, isopropyl pyruvate, benzoylformic acid, methyl benzoylformate and ethyl benzoylformate.
  • keto acids and keto esters such as pyruvic acid, methyl pyruvate, ethyl pyruvate, isopropyl pyruvate, benzoylformic acid, methyl benzoylformate and ethyl benzoylformate.
  • beta hydroxyacid for use in the invention is salicylic acid.
  • the hydroxy acids and related compounds may be employed as free acids or esters, lactones, amides, anhydrides, inorganic metal salts, ammonium salts or salts created by reacting a hydroxy acid with an amino acid. Because of the natural presence of water-soluble acids in human skin, certain salts of these acids may convert, at least partially, to free acid form upon application.
  • the hydroxyacid and/or derivatives thereof should be employed at a concentration of between about 1 and 25% w/w, and preferably between 2.0 and 10%.
  • the three components, together with appropriate carriers or vehicles, can be compounded into dermatologically useful cream, lotion, solution or gel preparations as follows:
  • the cream is prepared by combining the oil-phase ingredients in a mixing container and heating them to 70 degrees C.
  • the water phase ingredients except for the Lactic acid and Magnesium ascorbyl phosphate, are combined and heated to the same temperature.
  • the two phases are then combined and cooled with constant mixing.
  • At approximately 50 degrees the Lactic acid and ascorbate are dissolved.
  • it may be advantageously packaged as a dry powder in a separate container which would accompany ajar of the cream. At time of dispensing or first use, the powder would be incorporated into the cream with a stirring rod where it would dissolve in the water phase.
  • the lotion is prepared by combining the oil-phase ingredients in a mixing container and heating them to 75 degrees C.
  • the water phase ingredients except for the Lactic acid and Magnesium ascorbyl phosphate, are combined and heated to the same temperature.
  • the two phases arc then combined and cooled with constant mixing.
  • the Lactic acid and ascorbate are dissolved.
  • it may be advantageously packaged as a dry powder in a separate container which would accompany a bottle of the lotion. At time of dispensing or first use, the powder would be added to the lotion and shaken where it would dissolve in the water phase.
  • the solution is prepared by combining the alcohol, laureth-4 and squalane and adding the resulting solution slowly with mixing to the aqueous solution of the other ingredients at room temperature.
  • they may be advantageously packaged as a dry blended powder in a separate container which would accompany the bottle of the solution. At time of dispensing or first use, the powder would be added to the solution and shaken where it would dissolve in the hydro-alcoholic solvent carrier.
  • the gel is prepared by combining the alcohol, Salicylic acid, laureth-4 and squalane and adding the resulting solution slowly with mixing to the aqueous solution of the other ingredients at room temperature.
  • the kojic acid, N-Acetyl cysteine and ascorbate may be advantageously packaged as a dry blended powder in a separate container which would accompany the bottle of the solution.
  • the powder would be added to the gel and stirred or shaken where it would dissolve in the hydro-alcohol solvent carrier.
  • the Melanoderm assay is an in vitro model of the human epidermis consisting of well differentiated, cultured human keratinocytes and melanocytyes. This model can be used to evaluate the efficacy, stability and cytotoxicity of skin lightening agents.
  • L-DOPA L- Dihydroxyphenylalanine

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  • 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)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un procédé pour éclaircir la peau, selon lequel on applique sur des zones hyperpigmentées de la peau une composition comprenant : (1) de l'acide kojique ou des dérivés de cet acide, (2) un antioxydant et (3) un hydroxyacide ou des dérivés de cet hydroxyacide. L'invention concerne également une composition servant à éclaircir la peau, qui comprend : (1) de l'acide kojique ou des dérivés de cet acide, (2) un antioxydant et (3) un hydroxyacide ou des dérivés de cet hydroxyacide.
PCT/US2001/007182 2000-03-07 2001-03-07 Procede et composition pour eclaircir la peau WO2001066105A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001245474A AU2001245474A1 (en) 2000-03-07 2001-03-07 Method and composition for lightening the skin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US18752000P 2000-03-07 2000-03-07
US60/187,520 2000-03-07

Publications (1)

Publication Number Publication Date
WO2001066105A1 true WO2001066105A1 (fr) 2001-09-13

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ID=22689316

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/007182 WO2001066105A1 (fr) 2000-03-07 2001-03-07 Procede et composition pour eclaircir la peau

Country Status (2)

Country Link
AU (1) AU2001245474A1 (fr)
WO (1) WO2001066105A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002026206A1 (fr) * 2000-09-29 2002-04-04 Beiersdorf Ag Preparations cosmetiques et dermatologiques contenant de l'aminoguanidine
DE102010051689A1 (de) 2010-11-17 2012-05-24 Merck Patent Gmbh Dihydroxyfumarsäure-Derivate und deren Verwendung zur Hautaufhellung
US20130156710A1 (en) * 2010-05-25 2013-06-20 Symrise Ag Cyclohexyl carbamate compounds as skin and/or hair lightening actives
GB2497985A (en) * 2011-12-28 2013-07-03 Pangaea Lab Ltd Stable kojic acid composition to lighten the skin
CN110785395A (zh) * 2017-06-26 2020-02-11 巴斯夫欧洲公司 羟基酸的烷氧基化

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999036053A1 (fr) * 1998-01-16 1999-07-22 Color Access, Inc. Compositions de blanchiment stabilisees et leur procede de preparation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999036053A1 (fr) * 1998-01-16 1999-07-22 Color Access, Inc. Compositions de blanchiment stabilisees et leur procede de preparation

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002026206A1 (fr) * 2000-09-29 2002-04-04 Beiersdorf Ag Preparations cosmetiques et dermatologiques contenant de l'aminoguanidine
US20130156710A1 (en) * 2010-05-25 2013-06-20 Symrise Ag Cyclohexyl carbamate compounds as skin and/or hair lightening actives
US9072676B2 (en) * 2010-05-25 2015-07-07 Symrise Ag Cyclohexyl carbamate compounds as skin and/or hair lightening actives
DE102010051689A1 (de) 2010-11-17 2012-05-24 Merck Patent Gmbh Dihydroxyfumarsäure-Derivate und deren Verwendung zur Hautaufhellung
WO2012065680A2 (fr) 2010-11-17 2012-05-24 Merck Patent Gmbh Dérivés d'acide dihydroxyfumarique et leur utilisation pour l'éclaircissement de la peau
WO2012065680A3 (fr) * 2010-11-17 2013-06-27 Merck Patent Gmbh Dérivés d'acide dihydroxyfumarique et leur utilisation pour l'éclaircissement de la peau
CN103269677A (zh) * 2010-11-17 2013-08-28 默克专利股份有限公司 二羟基富马酸衍生物及其用于使皮肤增白的用途
JP2013542964A (ja) * 2010-11-17 2013-11-28 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング ジヒドロキシフマル酸誘導体および皮膚美白のためのその使用
GB2497985A (en) * 2011-12-28 2013-07-03 Pangaea Lab Ltd Stable kojic acid composition to lighten the skin
GB2497985B (en) * 2011-12-28 2014-03-12 Pangaea Lab Ltd A composition to stabilise kojic acid
AU2012268879B2 (en) * 2011-12-28 2015-08-06 Medik8 Limited A Composition to Stabilise Kojic Acid
CN110785395A (zh) * 2017-06-26 2020-02-11 巴斯夫欧洲公司 羟基酸的烷氧基化

Also Published As

Publication number Publication date
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