FR2924601A1 - Composition, useful for depigmenting and/or bleaching of human skin, body hair or hair and to prepare dermatological composition, comprises hydroquinone diphosphate compound in a medium - Google Patents
Composition, useful for depigmenting and/or bleaching of human skin, body hair or hair and to prepare dermatological composition, comprises hydroquinone diphosphate compound in a medium Download PDFInfo
- Publication number
- FR2924601A1 FR2924601A1 FR0759640A FR0759640A FR2924601A1 FR 2924601 A1 FR2924601 A1 FR 2924601A1 FR 0759640 A FR0759640 A FR 0759640A FR 0759640 A FR0759640 A FR 0759640A FR 2924601 A1 FR2924601 A1 FR 2924601A1
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- compound
- alkyl group
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- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229940096998 ursolic acid Drugs 0.000 description 1
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/093—Polyol derivatives esterified at least twice by phosphoric acid groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/08—Preparations for bleaching the hair
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- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
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Abstract
Description
La présente invention concerne une composition cosmétique pour dépigmenter et/ou blanchir la peau comprenant un diphosphate d'hydroquinone ainsi que certains composés nouveaux . The present invention relates to a cosmetic composition for depigmenting and / or bleaching the skin comprising a hydroquinone diphosphate as well as certain new compounds.
La couleur de la peau humaine est fonction de différents facteurs et notamment des saisons de l'année, de la race et du sexe; elle est principalement déterminée par la nature et la concentration de mélanine produite par les mélanocytes. Les mélanocytes sont les cellules spécialisées qui, par l'intermédiaire d'organelles par- ticuliers, les mélanosomes, synthétisent la mélanine. En outre, à différentes périodes de leur vie, certaines personnes voient apparaître sur la peau et plus spécialement sur les mains, des taches plus foncées et/ou plus colorées, conférant à la peau une hétérogénéité. Ces taches sont dues aussi à une concentration importante de mélanine dans les kératinocytes situés à la surface de la peau. The color of human skin is a function of various factors including seasons of the year, race and sex; it is mainly determined by the nature and concentration of melanin produced by melanocytes. Melanocytes are the specialized cells that, through the use of particular organelles, melanosomes, synthesize melanin. In addition, at different periods of their life, some people see on the skin and especially on the hands, darker spots and / or more colorful, giving the skin a heterogeneity. These spots are also due to a high concentration of melanin in keratinocytes located on the surface of the skin.
L'utilisation de substances dépigmentantes topiques inoffensives présentant une bonne efficacité est tout particulièrement recherchée en vue de traiter les hyperpigmentations régionales par hyperactivité mélanocytaire telles que les mélasmas idiopathiques, survenant lors de la grossesse ("masque de grossesse" ou chloas- ma) ou d'une contraception oestro-progestative, les hyperpigmentations localisées par hyperactivité et prolifération mélanocytaire bénigne, telles que les taches pigmentaires séniles dites lentigo actiniques, les hyperpigmentations accidentelles, éventuellement dues à la photosensibilisation ou à la cicatrisation post-lésionnelle, ainsi que certaines leucodermies, telles que le vitiligo. Pour ces dernières (les ci- catrisations pouvant aboutir à une cicatrice donnant à la peau un aspect plus blanc), à défaut de pouvoir repigmenter la peau lésée, on achève de dépigmenter les zones de peau normale résiduelle pour donner à l'ensemble de la peau une teinte blanche homogène. The use of harmless topical depigmenting substances with good efficacy is particularly sought for the treatment of regional hyperpigmentations by melanocytic hyperactivity such as idiopathic melasmas, occurring during pregnancy ("pregnancy mask" or chloasma) or oestro-progestative contraception, hyperpigmentations localized by hyperactivity and benign melanocyte proliferation, such as senile pigmentary spots known as actinic lentigo, accidental hyperpigmentations, possibly due to photosensitization or post-injury wound healing, as well as certain leukoderma, such as than vitiligo. For the latter (the cicatrizations may result in a scar giving the skin a whiter appearance), failing to repigment the damaged skin, it is necessary to depigment the areas of residual normal skin to give the whole of the skin. skin a uniform white hue.
Le mécanisme de formation de la pigmentation de la peau, c'est-à-dire de la formation de la mélanine est particulièrement complexe et fait intervenir schématiquement les principales étapes suivantes : Tvrosine ---> Dopa ---> Dopaquinone ---> Dopachrome ---> Mélanine 35 La tyrosinase (monophénol dihydroxyl phénylalanine : oxygen oxydo-reductase EC 1.14.18.1) est l'enzyme essentielle intervenant dans cette suite de réactions. Elle catalyse notamment la réaction de transformation de la tyrosine en Dopa (dihydroxyphénylalanine) grâce à son activité hydroxylase et la réaction de transfor- 40 mation de la Dopa en dopaquinone grâce à son activité oxydase. Cette tyrosinase n'agit que lorsqu'elle est à l'état de maturation sous l'action de certains facteurs biologiques. The mechanism of formation of skin pigmentation, that is to say the formation of melanin is particularly complex and involves schematically the following main steps: Trevosine ---> Dopa ---> Dopaquinone --- > Dopachrome ---> Melanine Tyrosinase (monophenol dihydroxyl phenylalanine: oxygen oxido-reductase EC 1.14.18.1) is the essential enzyme involved in this series of reactions. It catalyzes, in particular, the conversion reaction of tyrosine to Dopa (dihydroxyphenylalanine) by virtue of its hydroxylase activity and the reaction of transformation of Dopa into dopaquinone by virtue of its oxidase activity. This tyrosinase only acts when it is maturing under the influence of certain biological factors.
Une substance est reconnue comme dépigmentante si elle agit directement sur la vitalité des mélanocytes épidermiques où se déroule la mélanogénèse, et/ou si elle interfère avec une des étapes de la biosynthèse de la mélanine soit en inhi- bant une des enzymes impliquées dans la mélanogénèse, soit en s'intercalant comme analogue structural d'un des composés chimiques de la chaîne de synthèse de la mélanine, chaîne qui peut alors être bloquée et ainsi assurer la dépigmentation. A substance is recognized as depigmenting if it acts directly on the vitality of the melanogenetic melanocyte melanocytes, and / or if it interferes with one of the stages of melanin biosynthesis by inhibiting one of the enzymes involved in melanogenesis. or by interposing itself as a structural analogue of one of the chemical compounds of the melanin synthesis chain, which chain can then be blocked and thus ensure depigmentation.
Les substances les plus utilisées en tant que dépigmentants sont plus particulièrement l'hydroquinone et ses dérivés, en particulier ses éthers tels que le monométhyléther et le monoéthyléther d'hydroquinone. Ces composés, bien qu'ils pré-sentent une efficacité certaine, ne sont malheureusement pas exempts d'effets secondaires du fait de leur toxicité, ce qui peut rendre leur emploi délicat, voire dangereux. Cette toxicité provient de ce qu'ils interviennent sur des mécanismes fondamentaux de la mélanogénèse en tuant des cellules qui risquent alors de perturber leur environnement biologique et qui par conséquent obligent la peau à les évacuer en produisant des toxines. The substances most used as depigmenting agents are more particularly hydroquinone and its derivatives, in particular its ethers such as monomethyl ether and hydroquinone monoethyl ether. These compounds, although they have a certain effectiveness, are unfortunately not free of side effects because of their toxicity, which can make their use difficult, even dangerous. This toxicity comes from the fact that they interfere with the fundamental mechanisms of melanogenesis by killing cells that may then disturb their biological environment and therefore force the skin to evacuate them by producing toxins.
Ainsi, l'hydroquinone est un composé particulièrement irritant et cytotoxique pour le mélanocyte, dont le remplacement, total ou partiel a été envisagé par de nombreux auteurs. Thus, hydroquinone is a particularly irritating and cytotoxic compound for the melanocyte, whose replacement, total or partial has been considered by many authors.
On a ainsi cherché des substances qui n'interviennent pas dans le mécanisme de la mélanogénèse mais qui agissent en amont sur la tyrosinase en empêchant son activation et sont de ce fait beaucoup moins toxiques. On utilise couramment comme inhibiteur de l'activation de la tyrosinase l'acide kojique qui complexe le cuivre présent dans le site actif de cette enzyme. Malheureusement, ce composé est instable en solution, ce qui complique quelque peu la fabrication de la campo- sition. We have thus looked for substances that do not intervene in the mechanism of melanogenesis but act upstream on tyrosinase by preventing its activation and are therefore much less toxic. The kojic acid which complexes copper present in the active site of this enzyme is commonly used as an inhibitor of tyrosinase activation. Unfortunately, this compound is unstable in solution, which somewhat complicates the manufacture of the camp.
Il subsiste le besoin d'un nouvel agent blanchissant de la peau humaine à action aussi efficace que ceux connus, mais n'ayant pas leurs inconvénients, c'est-à-dire qui soit non irritant, non toxique et/ou non allergisant pour la peau, tout en étant stable dans une composition, ou bien alternativement qui possède une action renforcée de façon à pouvoir être utilisé en quantité plus faible, ce qui diminue considérablement les effets secondaires observés. A cet égard la Demanderesse a de manière surprenante et inattendue découvert que certains composés d'hydroquinone présentaient une bonne activité dépigmen- tante, même à faible concentration, sans faire preuve de cytotoxicité. 5 De façon plus précise, l'invention a donc pour objet une composition, notamment destinée à destinée à dépigmenter et/ou blanchir la peau comprenant, dans un milieu physiologiquement acceptable, au moins un composé de formule (I) sui- vante : There remains the need for a new whitening agent for human skin with action as effective as those known, but not having their disadvantages, that is to say which is non-irritating, non-toxic and / or non-allergenic to the skin, while being stable in a composition, or alternatively which has a reinforced action so that it can be used in a smaller quantity, which considerably reduces the observed side effects. In this regard, it has surprisingly and unexpectedly been found that certain hydroquinone compounds exhibit good depigmenting activity, even at low concentrations, without exhibiting cytotoxicity. More specifically, the subject of the invention is therefore a composition, in particular intended to depigment and / or whiten the skin, comprising, in a physiologically acceptable medium, at least one compound of formula (I) below:
OR R1 R2 OR' (I) dans laquelle : OR R1 R2 OR '(I) wherein:
10 R et R' désignent un groupement phosphate ; R1 et R2 désignent, indépendamment l'un de l'autre, un atome d'hydrogène ou un groupe alkyle linéaire en C1 û C6 ou ramifié en C3-06, éventuellement substitué par un groupement -000R' ou ûCONR'R" , R' et R" désignant, indépendamment l'un de l'autre, un atome d'hydrogène ou un groupe alkyle en C1-C4 ; 15 ainsi que leurs sels cosmétiquement acceptables, leurs solvates tels que les hydrates et leurs isomères optiques et géométriques. R and R 'denote a phosphate group; R1 and R2 denote, independently of each other, a hydrogen atom or a C1-C6 or branched C3-C6 linear alkyl group, optionally substituted with a -000R 'or a -CONR'R "group; and R "denoting, independently of one another, a hydrogen atom or a C1-C4 alkyl group; As well as their cosmetically acceptable salts, their solvates such as hydrates and their optical and geometrical isomers.
Les composés de formule (I) selon l'invention permettent de dépigmenter et/ou 20 d'éclaircir efficacement la peau d'êtres humains. Ils sont notamment destinés à être appliqués sur la peau d'individus présentant des taches de pigmentation brunâtres, des taches de sénescence, ou sur la peau d'individus désirant combattre l'apparition d'une couleur brunâtre provenant de la mélanogénèse, par exemple à la suite d'une exposition aux rayonnements ultra-violet. 25 L'invention a donc également pour objet un procédé cosmétique de dépigmentation et/ou de blanchiment de la peau humaine comprenant l'application sur la peau d'une composition telle que décrite précédemment. Le procédé convient notamment pour éliminer les taches pigmentaires brunâtres et/ou les 30 taches de sénescence, et/ou pour éclaircir la peau brunie. The compounds of formula (I) according to the invention make it possible to depigment and / or effectively lighten the skin of human beings. They are intended to be applied to the skin of individuals with brownish pigmentation spots, senescence spots, or on the skin of individuals wishing to combat the appearance of a brownish color from melanogenesis, for example to following exposure to ultraviolet radiation. The invention therefore also relates to a cosmetic process for depigmenting and / or bleaching human skin comprising applying to the skin a composition as described above. The method is particularly suitable for removing brownish pigment spots and / or senescence spots, and / or for lightening burnished skin.
L'invention a encore pour objet l'utilisation cosmétique d'un composé de formule (I) tel que décrit précédemment comme agent blanchissant et/ou dépigmentant de la peau, notamment pour éliminer les taches pigmentaires, les taches de sénes- 35 cence et/ou en tant qu'agents anti-brunissement. The subject of the invention is also the cosmetic use of a compound of formula (I) as described above as a bleaching and / or depigmenting agent for the skin, in particular for eliminating pigment spots, senescence spots and or as anti-browning agents.
L'invention a aussi pour objet l'utilisation d'un composé de formule (I) tel décrit précédemment pour la fabrication d'une composition dermatologique destinée à dé-pigmenter et/ou blanchir la peau. The invention also relates to the use of a compound of formula (I) as described above for the manufacture of a dermatological composition for de-pigmenting and / or bleaching the skin.
Parmi les composés de formule (I), le sel tétrasodique de 1,6-0-diphosphate d'hydroquinone a pour registry number RN : 857469-10-4 et est décrit dans l'article Experiments on the mechanism of action of tetrasodium 2-methyl-1,4-naphtoquinone diphosphate as a nitotic inhibitor and radiosensitizer, using the technique of tissue culture , Mitchell, J.S. ; Simons-Reuss, I. ; British Journal of cancer (1952), 6, p 317-38. Among the compounds of formula (I), the tetrasodium salt of hydroquinone-1,6-diphosphate has the registry number RN: 857469-10-4 and is described in the article Experiments on the mechanism of action of tetrasodium 2 methyl-1,4-naphthoquinone diphosphate as a nitotic inhibitor and radiosensitizer, using the technique of tissue culture, Mitchell, JS; Simons-Reuss, I.; British Journal of Cancer (1952), 6, p 317-38.
Le 1,6-0-diphosphate d'hydroquinone (RN : 75805-16-2) est décrit dans les de-mandes US-A-2005/100976 et US-A-2004/0265922. Hydroquinone-1,6-diphosphate (RN: 75805-16-2) is described in US-A-2005/100976 and US-A-2004/0265922.
L'invention a donc aussi pour objet les composés de formule (l') correspondant aux composés de formule (I) décrits précédemment à l'exclusion de ceux pour lesquels R1 = R2 = H. The subject of the invention is therefore also the compounds of formula (I ') corresponding to the compounds of formula (I) described above with the exception of those for which R1 = R2 = H.
Le terme alkyle, dans le cadre de la présente invention, signifie une chaîne hydro- carbonée saturée. Parmi les groupes alkyle convenant à la mise en oeuvre de l'invention, on peut notamment citer les groupes méthyle, éthyle, isopropyle, n-propyle, n-butyle, t-butyle, isobutyle, sec-butyle , pentyle, n-hexyle, cyclopropyle, cyclopentyle, cyclohexyle. Parmi les groupements alkyle préférés, on peut citer les groupements les groupe- ments méthyle, éthyle, iso-propyle, tert-butyle, et préférentiellement un groupe-ment éthyle. The term alkyl, in the context of the present invention, means a saturated hydrocarbon chain. Among the alkyl groups which are suitable for the implementation of the invention, mention may especially be made of methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec-butyl, pentyl and n-hexyl groups. cyclopropyl, cyclopentyl, cyclohexyl. Among the preferred alkyl groups, mention may be made of the groups methyl, ethyl, iso-propyl and tert-butyl groups, and preferably an ethyl group.
Les sels acceptables pour l'usage non thérapeutique des composés décrits dans la présente invention comprennent des sels non toxiques conventionnels desdits composés tels que ceux formés à partir d' une base minérale, telle que LiOH, NaOH, KOH, Ca(OH)2, NH4OH, Mg(OH)2 ou Zn(OH)2; ou d'une base organique telle qu'une alkylamine primaire, secondaire ou tertiaire, par exemple la triéthylamine ou la butylamine. Cette alkylamine primaire, secondaire ou tertiaire peut comporter un ou plusieurs atomes d'azote et/ou d'oxygène et peut donc comporter par exemple une ou plusieurs fonctions alcool; on peut notamment citer l'amino-2-méthyl-2-propanol, la triéthanolamine, la diméthylamino-2-propanol, le 2-amino-2-(hydroxyméthyl)-1,3-propanediol. On peut encore citer la lysine ou la 3-(di méthylamino)propylamine. Salts acceptable for non-therapeutic use of the compounds described in the present invention include conventional non-toxic salts of said compounds such as those formed from a mineral base, such as LiOH, NaOH, KOH, Ca (OH) 2, NH4OH, Mg (OH) 2 or Zn (OH) 2; or an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and / or oxygen atoms and may therefore comprise, for example, one or more alcohol functions; mention may especially be made of 2-amino-methyl-2-propanol, triethanolamine, dimethylamino-2-propanol and 2-amino-2- (hydroxymethyl) -1,3-propanediol. We can also mention lysine or 3- (di methylamino) propylamine.
Les solvates acceptables pour l'usage non thérapeutique des composés décrits dans la présente invention comprennent des solvates conventionnels tels que ceux formés lors de la dernière étape de préparation desdits composés du fait de la présence de solvants. A titre d'exemple, on peut citer les solvates dus à la présence d'eau ou d'alcools linéaires ou ramifiés comme l'éthanol ou l'isopropanol. The solvates acceptable for the non-therapeutic use of the compounds described in the present invention include conventional solvates such as those formed in the last step of preparing said compounds due to the presence of solvents. By way of example, mention may be made of solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.
Dans la structure de formule (I) ou (l'), le groupe R1 est de préférence en position 5 ortho par rapport au groupe ûOR. In the structure of formula (I) or (I '), the group R 1 is preferably in the 5-position ortho to the group OR.
Un aspect avantageux de l'invention concerne les composés de formule (I) pour lesquels : R1 = R2 = H , ou 10 R1 = H et R2 désigne un groupe alkyle linéaire en C1 û C6 ou ramifié en C3-06, éventuellement substitué par un groupement -0O0R' ou ûCONR'R" , R' et R" désignant, indépendamment l'un de l'autre, un atome d'hydrogène ou un groupe alkyle en C1-C4 . An advantageous aspect of the invention relates to the compounds of formula (I) in which: R 1 = R 2 = H, or R 1 = H and R 2 denotes a linear C 1 -C 6 or branched C 3 -C 6 alkyl group, optionally substituted with a group -COOR 'or -CONR'R ", R' and R" denoting, independently of one another, a hydrogen atom or a C1-C4 alkyl group.
15 Un autre aspect particulier de l'invention concerne les composés de formule (I) pour lesquels : R1 = R2 = H , ou R1 = H et R2 désigne un groupe alkyle linéaire en C1 û C6 substitué par un groupement ûCOO-CH2CH3 ; R2 étant de préférence le groupe -CH2-COO-CH2CH3. 20 Les composés de formule (I') préférés sont ceux pour lesquels : Another particular aspect of the invention relates to the compounds of formula (I) wherein: R 1 = R 2 = H, or R 1 = H and R 2 denotes a linear C 1 -C 6 alkyl group substituted with a group -COO-CH 2 CH 3; R2 being preferably -CH2-COO-CH2CH3. Preferred compounds of formula (I ') are those for which:
R1 = H et R2 désigne un groupe alkyle linéaire en C1 û C6 ou ramifié en C3-06, éventuellement substitué par un groupement -0O0R' ou ûCONR'R" , R' et R" 25 désignant, indépendamment l'un de l'autre, un atome d'hydrogène ou un groupe alkyle en C1-C4 . R 1 = H and R 2 denotes a linear C 1 -C 6 or branched C 3 -C 6 alkyl group, optionally substituted with a group -OORR 'or -CONR'R ", R' and R" denoting, independently of one of the another, a hydrogen atom or a C1-C4 alkyl group.
Les composés de formule (I') particulièrement préférés sont ceux pour lesquels : R1 = H et R2 désigne un groupe alkyle linéaire en C1 û C6 substitué par un grau-30 pement ûCOOCH2CH3 ; R2 étant de préférence le groupe -CH2-COO-CH2CH3. The compounds of formula (I ') which are particularly preferred are those for which: R 1 = H and R 2 denotes a linear C 1 -C 6 alkyl group substituted with a degree of addition of COOCH 2 CH 3; R2 being preferably -CH2-COO-CH2CH3.
Les composés de formule (I) et (I') plus particulièrement préférés sont les suivants : The compounds of formula (I) and (I ') more particularly preferred are the following:
35 - le 1,6-0-diphosphate d'hydroquinone (composé 1) ou ses sels comme son sel de sodium :5 0 HO\ // P / OH O 0, ,0 HO' OH - le diphosphate d'homogentisate d'éthyle ou ses sels comme son sel de sodium (composé 2) : O , -~ O PùO O O O De façon générale, les composés de formule (I) peuvent être préparés par réaction d'un composé de formule (Il) Hydroquinone 1,6-o-diphosphate (compound 1) or its salts such as its sodium salt: homogentisate diphosphate (OH); In general, the compounds of formula (I) can be prepared by reacting a compound of formula (II) with ethyl or its salts, such as its sodium salt (compound 2): ## STR2 ##
OH R2 OH (Il) R1 et R2 ayant la significations décrites précédemment pour les composés de formule (I), Wherein R1 and R2 have the meaning previously described for the compounds of formula (I),
20 avec de l'oxychlorure de phosphore (POC13), en présence d'une base comme la pyridine, éventuellement dans un milieu solvant inerte tel que le tétrahydrofurane. 10 15 Comme base, on peut également utiliser une base minérale telle que la soude, la potasse, le bicarbonate de sodium ou de potassium, le carbonate de sodium ou de potassium. With phosphorus oxychloride (POCl 3) in the presence of a base such as pyridine, optionally in an inert solvent medium such as tetrahydrofuran. As a base, it is also possible to use a mineral base such as sodium hydroxide, potassium hydroxide, sodium or potassium bicarbonate, sodium carbonate or potassium carbonate.
La réaction peut être effectuée à une température allant de 0 °C à 60 °C. The reaction can be carried out at a temperature ranging from 0 ° C to 60 ° C.
Après réaction, le sel de sodium peut être formé dans le méthanol avec une solution aqueuse d'hydroxyde de sodium. After reaction, the sodium salt can be formed in methanol with an aqueous solution of sodium hydroxide.
Les composés de formule (Il) pour lesquels R2 désigne un groupe alkyle linéaire en C1 ù C6 ou ramifié en C3-C6, substitué par un groupement ùCOOR' avec R' désignant un groupe alkyle en C1-C4 ; ou ûCONR'R" , R' et R" désignant, indépendamment l'un de l'autre, un atome d'hydrogène ou un groupe alkyle en C1-C4 ; peuvent être obtenus, de façon connue, par estérification ou amidification de l'acide carboxylique correspondant. Compounds of formula (II) wherein R 2 denotes a linear C 1 -C 6 or branched C 3 -C 6 alkyl group, substituted with a group -COR 'with R' denoting a C 1 -C 4 alkyl group; or -CONR'R ", R 'and R" denoting, independently of one another, a hydrogen atom or a C1-C4 alkyl group; can be obtained, in known manner, by esterification or amidification of the corresponding carboxylic acid.
Un autre objet de l'invention concerne une composition comprenant, dans un mi-lieu physiologiquement acceptable, au moins un composé de formule (I) telle que définie ci-dessus. En particulier la composition est adaptée à une application tapi- que sur la peau. Le milieu physiologiquement acceptable sera préférentiellement un milieu cosmétiquement ou dermatologiquement acceptable, c'est-à-dire sans odeur, couleur ou aspect désagréable, et qui ne génère pas de picotement, tiraillement ou rougeur inacceptable pour l'utilisateur. Another subject of the invention relates to a composition comprising, in a physiologically acceptable medium, at least one compound of formula (I) as defined above. In particular, the composition is suitable for application to the skin. The physiologically acceptable medium will preferably be a cosmetically or dermatologically acceptable medium, that is to say without odor, color or unpleasant appearance, and which does not generate tingling, tightness or redness unacceptable to the user.
Par milieu physiologiquement acceptable, on comprend un milieu compatible avec les matières kératiniques d'êtres humains comme la peau, les muqueuses, les ongles, le cuir chevelu et/ou les cheveux. By physiologically acceptable medium, an environment compatible with keratin materials of human beings such as the skin, the mucous membranes, the nails, the scalp and / or the hair is understood.
La composition selon l'invention peut être destinée à une application cosmétique ou pharmaceutique, particulièrement dermatologique. De préférence la composition selon l'invention est destinée à une application cosmétique. The composition according to the invention may be intended for a cosmetic or pharmaceutical application, particularly dermatological. Preferably the composition according to the invention is intended for a cosmetic application.
La quantité de composés de formule (I) utilisable dans le cadre de l'invention dé-pend bien évidemment de l'effet recherché. The quantity of compounds of formula (I) that can be used in the context of the invention obviously depends on the desired effect.
A titre d'exemple, cette quantité peut aller par exemple de 0,001% à 10% en poids, de préférence de 0,01% à 5% en poids, notamment de 0,1 à 2% en poids, par rapport au poids total de la composition. By way of example, this amount may range, for example, from 0.001% to 10% by weight, preferably from 0.01% to 5% by weight, in particular from 0.1% to 2% by weight, relative to the total weight of the composition.
La composition peut alors comprendre tous les constituants usuellement employés dans l'application envisagée. On peut notamment citer l'eau, les solvants, les huiles d'origine minérale, animale et/ou végétale, les cires, les pigments, les charges, les tensioactifs, les actifs cos-métiques ou dermatologiques, les filtres UV, les polymères, les gélifiants, les conservateurs, les parfums. The composition may then comprise all the constituents usually employed in the intended application. It may especially be mentioned water, solvents, oils of mineral, animal and / or vegetable origin, waxes, pigments, fillers, surfactants, cosmetic or dermatological agents, UV filters, polymers , gelling agents, preservatives, perfumes.
Bien entendu l'homme du métier veillera à choisir ce ou ces éventuels composés complémentaires, et/ou leur quantité, de manière telle que les propriétés avantageuses des composés selon l'invention ne soient pas, ou substantiellement pas, altérées par l'adjonction envisagée. Of course, those skilled in the art will take care to choose this or these optional additional compounds, and / or their quantity, in such a way that the advantageous properties of the compounds according to the invention are not, or not substantially, impaired by the addition envisaged. .
La composition selon l'invention peut se présenter sous toutes les formes galéni- ques normalement utilisées dans les domaines cosmétique et dermatologique; elle peut être notamment sous forme d'une solution aqueuse, hydroalcoolique, éventuellement gélifiée, d'une dispersion du type lotion éventuellement biphasée, d'une émulsion huile-dans-eau ou eau-dans-huile ou multiple, d'un gel aqueux, d'une dispersion d'huile dans une phase aqueuse à l'aide de sphérules, ces sphérules pouvant être des nanoparticules polymériques telles que les nanosphères et les nanocapsules ou, mieux, des vésicules lipidiques de type ionique et/ou non-ionique. The composition according to the invention may be in any galenical form normally used in the cosmetic and dermatological fields; it may especially be in the form of an aqueous solution, hydroalcoholic, optionally gelled, a dispersion of the lotion type possibly two-phase, an oil-in-water or water-in-oil or multiple emulsion, an aqueous gel , an oil dispersion in an aqueous phase using spherules, these spherules may be polymeric nanoparticles such as nanospheres and nanocapsules or, better, lipid vesicles of ionic and / or nonionic type.
Lorsque la composition de l'invention est une émulsion, la proportion de la phase grasse peut aller de 5 à 80 % en poids, et de préférence de 5 à 50 % en poids par rapport au poids total de la composition. Les huiles, les émulsionnants et les éventuels coémulsionnants utilisés dans la composition sous forme d'émulsion sont choisis parmi ceux classiquement utilisés dans le domaine considéré. L'émulsionnant et le coémulsionnant sont présents, dans la composition, en une proportion pouvant aller de 0,3 à 30 % en poids, et de préférence de 0,5 à 20 % en poids par rapport au poids total de la composition. When the composition of the invention is an emulsion, the proportion of the fatty phase can range from 5 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition. The oils, emulsifiers and optional coemulsifiers used in the composition in emulsion form are chosen from those conventionally used in the field under consideration. The emulsifier and the coemulsifier are present in the composition in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% by weight relative to the total weight of the composition.
Cette composition peut être plus ou moins fluide et avoir l'aspect d'une crème blanche ou colorée, d'une pommade, d'un lait, d'une lotion, d'un sérum, d'une pâte, d'une mousse. Elle peut éventuellement être appliquée sur la peau sous forme d'aérosol. Elle peut également se présenter sous forme solide, et par exemple sous forme de stick. Elle peut être utilisée comme produit de soin et/ou comme produit de maquillage. This composition may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a mousse . It can optionally be applied to the skin in the form of an aerosol. It can also be in solid form, and for example in the form of a stick. It can be used as a care product and / or as a makeup product.
Cette composition peut constituer une crème de nettoyage, de protection, de traitement ou de soin pour le visage, pour les mains, pour les pieds, pour les grands plis anatomiques ou pour le corps (par exemple crèmes de jour, crèmes de nuit, crèmes démaquillantes, crèmes de fond de teint, crèmes anti-solaires); un fond de teint fluide, un lait de démaquillage, un lait corporel de protection ou de soin, un lait anti-solaire; une lotion, gel ou mousse pour le soin de la peau, comme une lotion de nettoyage. This composition may constitute a cream for cleaning, protecting, treating or caring for the face, for the hands, for the feet, for large anatomical folds or for the body (for example, day creams, night creams, creams). make-up removers, foundation creams, sunscreen creams); a fluid foundation, a make-up removal milk, a body care or protection milk, an anti-sun milk; a lotion, gel or mousse for the care of the skin, such as a cleaning lotion.
Dans un aspect avantageux de l'invention, les compositions utilisées peuvent comporter en plus au moins un agent desquamant, et/ou au moins un agent apaisant, et/ou au moins agent photoprotecteur organique et/ou au moins un agent photoprotecteur inorganique. Par "agent desquamant", on entend tout composé capable d'agir : In an advantageous aspect of the invention, the compositions used may further comprise at least one desquamating agent, and / or at least one soothing agent, and / or at least one organic photoprotective agent and / or at least one inorganic photoprotective agent. By "desquamating agent" is meant any compound capable of acting:
- soit directement sur la desquamation en favorisant l'exfoliation, tel que les 13-hydroxyacides, en particulier l'acide salicylique et ses dérivés (dont l'acide n- 10 octanoyl 5-salicylique) ; les a-hydroxyacides, tels que les acides glycolique, citrique, lactique, tartrique, malique ou mandélique ; l'urée ; l'acide gentisique ; les oligofucoses ; l'acide cinnamique ; l'extrait de Saphora japonica ; le resvératrol ; or directly on desquamation by promoting exfoliation, such as 13-hydroxy acids, in particular salicylic acid and its derivatives (including n-octanoyl-5-salicylic acid); α-hydroxy acids, such as glycolic, citric, lactic, tartaric, malic or mandelic acids; urea; gentisic acid; oligofucoses; cinnamic acid; Saphora japonica extract; resveratrol;
- soit sur les enzymes impliquées dans la desquamation ou la dégradation des 15 cornéodesmosomes, les glycosidases, la stratum corneum chymotryptic enzym (SCCE) voire d'autres protéases (trypsine, chymotrypsine-like). On peut citer les agents chélatant des sels minéraux : l'EDTA ; l'acide N-acyl-N,N',N' éthylène diaminetriacétique ; les composés aminosulfoniques et en particulier l'acide (N-2 hydroxyéthylpiperazine-N-2-éthane) sulfonique (HEPES) ; les dérivés de l'acide 2- 20 oxothiazolidine-4-carboxylique (procystéine) ; les dérivés d'acides alpha aminés de type glycine (tels que décrits dans EP-0 852 949, ainsi que le méthyl glycine diacétate de sodium commercialisé par BASF sous la dénomination commerciale TRILON M) ; le miel ; les dérivés de sucre tels que l'O-octanoyl-6-D-maltose et la N-acétyl glucosamine. 25 Comme agents apaisants utilisables dans la composition selon l'invention, on peut citer : les triterpènes pentacycliques et les extraits de plantes (ex : Glycyrrhiza glabra) en contenant comme l'acide 3-glycyrrhétinique et ses sels et/ou ses dérivés (l'acide glycyrrhétinique monoglucuronide, le stearyl glycyrrhetinate, 30 l'acide 3- stéaroyloxy glycyrrhetique), l'acide ursolique et ses sels, l'acide oléanolique et ses sels, l'acide bétulinique et ses sels, un extrait de Paeonia suffruticosa et / ou lactiflora, les sels de l'acide salicylique et en particulier le salicylate de zinc, les phycosaccharides de la société Codif, un extrait de Laminaria saccharina, l'huile de Canola, le bisabolol et les extraits de camomille, 35 l'allantoïne, le Sépivital EPC (diesterphosphorique de vitamine E et C) de Seppic, les huiles insaturées en oméga 3 telles que les huiles de rosier musca, de cassis, d'ecchium, de poisson, des extraits de plancton, la capryloyl glycine, le Seppicalm VG (sodium palmitoylproline et nymphea alba) de Seppic, un extrait du Pygeum, un extrait de Boswellia serrata, un extrait de Centipeda cunnighami, un extrait 40 d'Helianthus annuus, un extrait de Linum usitatissimum, les tocotrienols, les extraits de Cola nitida, le piperonal, un extrait de clou de girofle, un extrait d'Epilobium Angustifolium, l'aloe vera, un extrait de Bacopa moniera, les phytostérols, la cortisone, l'hydrocortisone, l'indométhacine et la beta méthasone.5 Les agents photoprotecteurs organiques sont notamment choisis parmi les anthranilates ; les dérivés cinnamiques ; les dérivés de dibenzoylméthane ; les dérivés salicyliques, les dérivés du camphre ; les dérivés de triazine tels que ceux dé- crits dans les demandes de brevet US 4367390, EP863145, EP517104, EP570838, EP796851, EP775698, EP878469, EP933376, EP507691, EP507692, EP790243, EP944624 ; les dérivés de la benzophénone ; les dérivés de 13,13-diphénylacrylate ; les dérivés de benzotriazole ; les dérivés de benzalmalonate ; les dérivés de benzimidazole ; les imidazolines ; les dérivés bis-benzoazolyle tels que décrits dans les brevets EP669323 et US 2,463,264; les dérivés de l'acide paminobenzoïque (PABA) ; les dérivés de méthylène bis-(hydroxyphényl benzotriazole) tels que décrits dans s les demandes US5,237,071, US5,166,355, GB2303549, DE 197 26 184 et EP893119 ; et les polymères filtres et silicones filtres tels que ceux décrits notamment dans la demande WO-93/04665 ; les dimè- res dérivés d'a-alkylstyrène tels que ceux décrits dans la demande de brevet DE19855649. or on the enzymes involved in desquamation or degradation of corneodesmosomes, glycosidases, stratum corneum chymotryptic enzyme (SCCE) or even other proteases (trypsin, chymotrypsin-like). Mention may be made of the chelating agents for mineral salts: EDTA; N-acyl-N, N ', N', ethylene diaminetriacetic acid; aminosulfonic compounds and in particular (N-2-hydroxyethylpiperazine-N-2-ethane) sulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid derivatives (procysteine); glycine-type alpha amino acid derivatives (as described in EP-0 852 949, as well as the sodium methyl glycine diacetate marketed by BASF under the trade name TRILON M); honey ; sugar derivatives such as O-octanoyl-6-D-maltose and N-acetyl glucosamine. As calming agents that may be used in the composition according to the invention, mention may be made of: pentacyclic triterpenes and plant extracts (eg Glycyrrhiza glabra) containing them, such as 3-glycyrrhetinic acid and its salts and / or derivatives thereof glycyrrhetinic acid monoglucuronide, stearyl glycyrrhetinate, 3-stearoyloxy glycyrrhetic acid), ursolic acid and its salts, oleanolic acid and its salts, betulinic acid and its salts, an extract of Paeonia suffruticosa and or lactiflora, salts of salicylic acid and in particular zinc salicylate, phycosaccharides from Codif, an extract of Laminaria saccharina, canola oil, bisabolol and chamomile extracts, allantoin, SEPIC SEPIVITAL EPC (diesterphosphoric vitamin E and C), omega 3 unsaturated oils such as rosehip musca, black currant, ecchium, fish, plankton extract, capryloyl glycine, Seppicalm V G (sodium palmitoylproline and nymphea alba) of Seppic, an extract of Pygeum, an extract of Boswellia serrata, an extract of Centipeda cunnighami, an extract of Helianthus annuus, an extract of Linum usitatissimum, tocotrienols, extracts of Cola nitida , piperonal, clove extract, Epilobium Angustifolium extract, aloe vera, Bacopa moniera extract, phytosterols, cortisone, hydrocortisone, indomethacin and beta methasone.5 Agents organic photoprotective agents are especially chosen from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives, camphor derivatives; triazine derivatives such as those described in US Patent Application Nos. 4367390, EP863145, EP517104, EP570838, EP796851, EP775698, EP878469, EP933376, EP507691, EP507692, EP790243, EP944624; benzophenone derivatives; 13,13-diphenylacrylate derivatives; benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imidazolines; bis-benzoazolyl derivatives as described in patents EP669323 and US 2,463,264; paminobenzoic acid derivatives (PABA); methylene bis (hydroxyphenyl benzotriazole) derivatives as described in US5,237,071, US5,166,355, GB2303549, DE 197 26 184 and EP893119; and filter polymers and silicone filters such as those described in particular in the application WO-93/04665; α-alkylstyrene derived dimers such as those described in patent application DE19855649.
Les agents photoprotecteurs inorganiques sont choisis parmi des pigments ou bien encore des nanopigments (taille moyenne des particules primaires: générale- ment entre 5 nm et 100 nm, de préférence entre 10 nm et 50 nm) d'oxydes métalliques enrobés ou non comme par exemple des nanopigments d'oxyde de titane (amorphe ou cristallisé sous forme rutile et/ou anatase), de fer, de zinc, de zirconium ou de cérium qui sont tous des agents photoprotecteurs UV bien connus en soi. Des agents d'enrobage classiques sont par ailleurs l'alumine et/ou le stéarate d'aluminium. De tels nanopigments d'oxydes métalliques, enrobés ou non enrobés, sont en particulier décrits dans les demandes de brevets EP518772 et EP518773. The inorganic photoprotective agents are chosen from pigments or even nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) of coated or uncoated metal oxides, for example nanopigments of titanium oxide (amorphous or crystallized in rutile and / or anatase form), iron, zinc, zirconium or cerium which are all UV photoprotective agents well known per se. Conventional coating agents are, moreover, alumina and / or aluminum stearate. Such nanopigments of metal oxides, coated or uncoated, are in particular described in patent applications EP518772 and EP518773.
Les agents photoprotecteurs sont généralement présents dans la composition selon l'invention dans des proportions allant de 0,1 à 20 % en poids par rapport au poids total de la composition, et de préférence allant de 0,2 à 15 % en poids par rapport au poids total de la composition. The photoprotective agents are generally present in the composition according to the invention in proportions ranging from 0.1 to 20% by weight relative to the total weight of the composition, and preferably ranging from 0.2 to 15% by weight relative to to the total weight of the composition.
Les exemples qui suivent illustrent l'invention sans en limiter la portée. Les composés sont, selon le cas, cités en noms chimiques ou en noms CTFA (Internatio-35 nal Cosmetic Ingredient Dictionary and Handbook). The examples which follow illustrate the invention without limiting its scope. The compounds are, as the case may be, cited in chemical names or CTFA names (International Cosmetic Ingredient Dictionary and Handbook).
Exemple 1 : Mise en évidence de l'activité sur la mélanogénèse. Example 1: Demonstration of the activity on melanogenesis.
40 Un test biologique a mis en évidence l'activité dépigmentante du sel tétrasodique du 1,6-0-diphosphate d'hydroquinone (composé 1) . L'effet modulateur sur la mélanogénèse du composé 1 a été mesuré selon la méthode décrite dans le brevet FR-A-2734825 , ainsi que dans l'article de R.Schmidt, P. Krien et M. Régnier, Anal. Bichem., 235(2), 113-18,1996. Ce test est réalisé sur coculture de kératinocytes et de mélanocytes. A bioassay demonstrated the depigmenting activity of the tetrasodium salt of hydroquinone 1,6-O-diphosphate (compound 1). The modulatory effect on the melanogenesis of compound 1 was measured according to the method described in patent FR-A-2734825, as well as in the article by R. Schmidt, P. Krien and M. Régnier, Anal. Bichem., 235 (2), 113-18,1996. This test is performed on coculture of keratinocytes and melanocytes.
Pour le composé testé, il a été déterminé : la cytotoxicité, en estimant l'incorporation de la leucine, l'activité inhibitrice sur la synthèse de la mélanine, en estimant le rapport de l'incorporation de thiouracile à l'incorporation de leucine, rapporté à 100 % du témoin (le témoin correspond au test réalisé sans composé à testé). Les va-leurs des IC50 (concentration pour laquelle 50 % de la synthèse de la méla- nine est inhibée) ont été déterminées. For the test compound, it was determined: the cytotoxicity, by estimating the incorporation of leucine, the inhibitory activity on melanin synthesis, by estimating the ratio of the incorporation of thiouracil to the incorporation of leucine, reported at 100% of the control (the control corresponds to the test carried out without test compound). The IC50 values (concentration for which 50% of the synthesis of melanin is inhibited) have been determined.
On a également effectué le test avec l'arbutine qui est un composé dépigmentant connu. The test was also performed with arbutin which is a known depigmenting compound.
Les résultats sont rassemblés dans le tableau suivant : Cytotoxicité IC50 ( M) Composé 1 Non 50 Arbutine Non 100 Le composé de l'exemple 1 se montre donc efficace pour inhiber la mélanogé- nèse ; il est par ailleurs plus efficace que l'arbutine. Par ailleurs, pour l'hydroquinone , une cytotoxicité apparait rapidement à des concentrations plus élevées (IC 50 : 30 % à 3 M). The results are summarized in the following table: Cytotoxicity IC 50 (M) Compound 1 No 50 Arbutin No 100 The compound of Example 1 is therefore effective in inhibiting melanogenesis; it is also more effective than arbutin. In addition, for hydroquinone, cytotoxicity appears rapidly at higher concentrations (50% CI: 30% at 3 M).
Exemple 2 : On prépare une crème blanchissante de soin du visage de type émulsion huiledans-eau, comprenant (% en poids) : Example 2: A whitening facial cream of the type emulsion oil-in-water, comprising (% by weight):
sel tétrasodique du 1,6-0-diphosphate d'hydroquinone (composé 1) 0,005% stéarate de glycérol 2% polysorbate 60 (Tween 60 de ICI) 1 1,4% 0,7% 0,4% 12% 12% 0,05% 35 acide stéarique triéthanolamine carbomer fraction liquide du beurre de karité perhydrosqualène antioxydant parfum, conservateur qs eau gsp100% tetrasodium salt of hydroquinone 1,6-0-diphosphate (compound 1) 0.005% glycerol stearate 2% polysorbate 60 (ICI Tween 60) 1 1.4% 0.7% 0.4% 12% 12% 0 , 05% 35 stearic acid triethanolamine carbomer liquid fraction shea butter perhydrosqualene antioxidant perfume, preservative qs water gsp100%
La composition appliquée sur la peau présentant des tâches de pigmentation 5 permet d'atténuer ces tâches. Exemple 3 : On prépare un gel dépigmentant pour la peau comprenant (% en poids) : 10 sel tétrasodique du 1,6-0-diphosphate d'hydroquinone (composé 1) 2% hydroxypropylcellulose (Klucel H de Hercules) 1 The composition applied to the skin with pigmentation spots makes it possible to reduce these tasks. Example 3 A skin depigmenting gel comprising (% by weight) is prepared: tetrasodium salt of hydroquinone 1,6-0-diphosphate (compound 1) 2% hydroxypropylcellulose (Klucel H from Hercules) 1
15 antioxydant 0,05% isopropanol 40% parfum, conservateur qs eau gsp100% 205 Antioxidant 0.05% isopropanol 40% perfume, preservative qs water gsp100% 205
Claims (13)
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FR0759640A FR2924601A1 (en) | 2007-12-07 | 2007-12-07 | Composition, useful for depigmenting and/or bleaching of human skin, body hair or hair and to prepare dermatological composition, comprises hydroquinone diphosphate compound in a medium |
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FR0759640A FR2924601A1 (en) | 2007-12-07 | 2007-12-07 | Composition, useful for depigmenting and/or bleaching of human skin, body hair or hair and to prepare dermatological composition, comprises hydroquinone diphosphate compound in a medium |
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FR0759640A Withdrawn FR2924601A1 (en) | 2007-12-07 | 2007-12-07 | Composition, useful for depigmenting and/or bleaching of human skin, body hair or hair and to prepare dermatological composition, comprises hydroquinone diphosphate compound in a medium |
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB547764A (en) * | 1940-01-10 | 1942-09-10 | Roche Products Ltd | A process for the manufacture of phosphoric acid esters of substituted hydroquinones |
WO1995023780A2 (en) * | 1994-03-04 | 1995-09-08 | The Procter & Gamble Company | Skin lightening compositions |
WO2002083092A1 (en) * | 2001-03-09 | 2002-10-24 | Amorepacific Corporation | Water-in-stable kojic acid derivatives and method for preparing thereof, and whitening cosmetics composition containing the same |
US20040028712A1 (en) * | 2002-08-12 | 2004-02-12 | Shepherd Walter B | Composition containing leukocyte extract for the whitening or lightening of skin |
US20040265922A1 (en) * | 2003-06-24 | 2004-12-30 | Ventana Medical Systems, Inc. | Enzyme-catalyzed metal deposition for the enhanced in situ detection of immunohistochemical epitopes and nucleic acid sequences |
-
2007
- 2007-12-07 FR FR0759640A patent/FR2924601A1/en not_active Withdrawn
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB547764A (en) * | 1940-01-10 | 1942-09-10 | Roche Products Ltd | A process for the manufacture of phosphoric acid esters of substituted hydroquinones |
WO1995023780A2 (en) * | 1994-03-04 | 1995-09-08 | The Procter & Gamble Company | Skin lightening compositions |
WO2002083092A1 (en) * | 2001-03-09 | 2002-10-24 | Amorepacific Corporation | Water-in-stable kojic acid derivatives and method for preparing thereof, and whitening cosmetics composition containing the same |
US20040028712A1 (en) * | 2002-08-12 | 2004-02-12 | Shepherd Walter B | Composition containing leukocyte extract for the whitening or lightening of skin |
US20040265922A1 (en) * | 2003-06-24 | 2004-12-30 | Ventana Medical Systems, Inc. | Enzyme-catalyzed metal deposition for the enhanced in situ detection of immunohistochemical epitopes and nucleic acid sequences |
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