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WO2018001571A1 - Composition de soin de la peau et méthode associée - Google Patents

Composition de soin de la peau et méthode associée Download PDF

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Publication number
WO2018001571A1
WO2018001571A1 PCT/EP2017/025183 EP2017025183W WO2018001571A1 WO 2018001571 A1 WO2018001571 A1 WO 2018001571A1 EP 2017025183 W EP2017025183 W EP 2017025183W WO 2018001571 A1 WO2018001571 A1 WO 2018001571A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
compound
skin
hydroxyl groups
ascorbic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2017/025183
Other languages
English (en)
Inventor
Aneshkumar Dineshchandra SITARAM
Jake Thomas HICKS
Paul James Tomlinson
Michael David Bell
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.)
Boots Co PLC
Original Assignee
Boots Co PLC
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 Boots Co PLC filed Critical Boots Co PLC
Publication of WO2018001571A1 publication Critical patent/WO2018001571A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • 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
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • 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

Definitions

  • the disclosed technology relates to a composition
  • a composition comprising: a cosmetically acceptable medium, an O-substituted ascorbic acid or derivative thereof; and a compound having two or more hydroxyl groups, wherein the compound has a molar mass of at least 150 g/mol and increases transglutaminase K expression in epidermal keratinocytes.
  • the disclosed technology further relates to the use and method of improving skin firmness, or reduced skin sagging with the composition.
  • Ageing is a multifactorial phenomenon.
  • the ageing phenomenon may be due to one or more of genetic predispositions (known as chronological or intrinsic ageing) and one's physiological reaction to environmental stresses (sometimes referred to as actinic or extrinsic ageing).
  • Actinic ageing appears to be skin specific and is defined as the effect of the external environment on the skin's biological response.
  • the skin response to actinic ageing which may be caused by sun and pollution exposure, as well as smoking, is typically associated with a lack of normal hydration, apparition of telangiectasia (spider veins), sagging of the skin, and/or reduced firmness of the skin. With sagging or reduced firmness the appearance of fine lines and wrinkles occurs.
  • the sagging or reduced skin firmness may be explained by the fact that the elastic fibres of the dermal extracellular matrix, forming the support and conferring elasticity and strength to the skin are destroyed and become rare with age.
  • one of the pathways to influence ageing involves the epidermal enzyme transglutaminase, a key driver of terminal keratinocyte differentiation and the development of the comified envelope.
  • the comified envelope allows the epidermis to maintain a healthy and strong skin barrier, and its production.
  • Transglutaminase, and its production is influenced by epidermal calcium concentration.
  • the decollete is generally believed to have the thinnest skin on the body, and has the fewest oil glands.
  • Face and neck skin similarly differ as neck skin is thinner than facial skin, and it has fewer oil glands than facial skin.
  • compositions disclosed relate to treating signs of ageing of facial skin.
  • the applications include:
  • the disclosed technology may be used to decrease or prevent at least one of the following: forming wrinkles or fine lines, skin sagging, or hyperpigmentation (such as solar lentigines), or increasing skin firmness or skin laxity.
  • the skin may include one or more of the face, neck and decollete.
  • the skin may include two or more (or all three) of the face, neck and decollete.
  • the disclosed technology relates to a composition having efficacy to increase the synthesis of transglutaminase-K (TGK); and that is believed to be beneficial for the appearance of healthy skin.
  • TTK transglutaminase-K
  • the transitional term "comprising,” which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, un-recited elements or method steps.
  • the term also encompass, as alternative embodiments, the phrases “consisting essentially of and “consisting of, where “consisting of excludes any element or step not specified and “consisting essentially of permits the inclusion of additional un-recited elements or steps that do not materially affect the basic, essential and novel characteristics of the composition, method or use under consideration.
  • treat rates are on a weight basis relative to the total composition disclosed herein.
  • the disclosed technology relates to a composition
  • a composition comprising: a cosmetically acceptable medium, an O-substituted ascorbic acid or derivative thereof; and a compound having two or more hydroxyl groups, wherein the compound has a molar mass of at least 150 g/mol.
  • the disclosed technology relates to a composition
  • a composition comprising: a cosmetically acceptable medium, an O-substituted ascorbic acid or derivative thereof; and a compound having two or more hydroxyl groups, wherein the compound has a molar mass of at least 150 g/mol and increases transglutaminase K expression in epidermal keratinocytes.
  • the disclosed technology relates to a composition is in the form of a cream, lotion or serum.
  • the disclosed technology relates to a composition comprising: a cosmetically acceptable medium, an O-substituted ascorbic acid or derivative thereof; and a compound having two or more hydroxyl groups, wherein the compound has a molar mass of at least 150 g/mol, wherein the cosmetically acceptable medium comprises an aqueous phase present at up to 95 wt %, or up to 90 wt % (for example 10 to 95 wt %, or 40 to 90 wt %) of the composition.
  • the disclosed technology relate to the cosmetic use of a composition disclosed herein (for example a skin care composition).
  • the disclosed technology relates to a method of decreasing or preventing at least one of the following: forming wrinkles or fine lines, skin sagging, or hyperpigmentation (such as solar lentigines), or increasing skin firmness or skin laxity comprising topically applying to skin the composition disclosed herein.
  • the skin may include one or more of the face, neck and decollete. In one embodiment the skin may include two of the face, neck and decollete. In one embodiment the skin may include the face, neck and decollete.
  • the disclosed technology relates to the use of the composition disclosed herein to decrease or prevent at least one of the following forming wrinkles or fine lines, skin sagging, or hyperpigmentation (such as solar lentigines), or to increase skin firmness or skin laxity of skin.
  • the method/use disclosed herein is capable of increasing/promoting the activity of transglutaminase by topically applying to decollete skin and optionally the face and/or neck skin the composition disclosed herein.
  • Skin may be a mammalian skin such as human skin.
  • the O-substituted ascorbic acid or derivative thereof may be an 0-alk(en)yl ascorbic acid or derivative thereof.
  • alk(en)yl is intended to mean alkyl or alkenyl (preferably alkyl).
  • the alk(en)yl may be acyclic or cyclic, for example acyclic.
  • the acyclic group may be linear or branched, for example linear.
  • the O-substituted ascorbic acid or derivative thereof may be an O- alkyl ascorbic acid, or derivative thereof.
  • O-substituted ascorbic acid or derivative thereof is known in the art, and described in EP Patent application EP2722043 Al, and US 2014/0155633 (both Lin et al, Applicant Corum).
  • O-substituted ascorbic acid or derivative thereof may be represented by the formula:
  • R 1 and R 2 groups may independently be H, C 1 -20 alkyl, C3-20 cycloalkyl, C 1 - 20 alkoxy, C2-20 acyl, C6-20 aryl, CI -20 heterocyclic aromatic, CI -20 heterocyclic non- aromatic, or C3-20 cycloalkenyl, with the proviso that both R 1 and R 2 cannot be H (i.e. with the proviso that the O-substituted ascorbic acid cannot be ascorbic acid in its unsubstituted form).
  • the O-substituted ascorbic acid or derivative thereof may have a substituted group that may be hydrocarbon in nature i.e., composed on carbon and hydrogen.
  • R 1 and R 2 groups may independently be H, CI -20 alkyl, C3-20 cycloalkyl, C6-20 aryl, or C3-20 cycloalkenyl with the proviso that both Rl and R2 cannot be H.
  • the O-substituted ascorbic acid may be 3 -alkyl ascorbic acid, or mixtures thereof.
  • the alkyl group may be a CI -20, or Cl-10, or C2-8, or C2-4.
  • the O-substituted ascorbic acid may be 3 -ethyl ascorbic acid.
  • the O-substituted ascorbic acid may be present at 0.001 to 5 wt %, or 0.01 to 3 wt %, or 0.1 to 2 wt % of the composition.
  • a compound having two or more hydroxyl groups, a molar mass of at least 150 g/mol and that increases TGK expression in epidermal keratinocytes when combined with an O-substituted ascorbic acid or derivative thereof as described above, provides improved firmness, reduces photodamage and reduces uneven skin tone after topical application to the face, neck and decollete.
  • Determining whether a compound having two or more hydroxyl groups and a molar mass of at least 150 g/mol is capable of increasing TGK expression in epidermal keratinocytes can be directly and positively verified by a person skilled in the art through, for example, a standard anti-TGK ELISA assay as described in Study 1. ELISA assays are so readily carried out that such analysis would not be considered to be a form of undue experimentation.
  • composition disclosed herein comprises a compound having two or more hydroxyl groups, wherein the compound has a molar mass of at least 150 g/mol, or at least 160 g/mol (herein referred to as "the compound").
  • the molar mas may be 150 to 2000 g /mol, or 160 to 1000 g/mol, or 160 to 700 g/mol, or 200 to 500 g/mol.
  • the compound may have 2 to 150, or 2 to 30, or 2 to 10, or 2 to 3, or 2 hydroxyl groups.
  • the compound may be ionic, or non-ionic.
  • the compound may be aromatic, or non-aromatic.
  • the compound may be a hydroxymethionine or one of its salts and / or derivatives.
  • a hydroxymethionine salt may include a metal salt, such as calcium, or magnesium salt of 2-hydroxymethionine.
  • the metal salt may be a calcium salt of 2-hydroxymethionine (for example with a molar mass of about 338.4 g/mol).
  • the calcium salt comprises two hydroxyl groups due to the presence of one hydroxyl per anion of the salt (since there are two moles of 2-hydroxymethionine per one mole of calcium cations).
  • the hydroxymethionine salt may be described in more detail in EP2209460.
  • EP2209460 describes a composition comprising a mixture of homotaurine and a hydroxymethionine, or one of its salts and / or derivatives (for example the calcium salt).
  • the compound may be an aromatic compound such a polyphenol.
  • the compound may be derived from an extract of a plant.
  • the extract of a plant may be a polyphenol.
  • the extract may be chosen from one or more of:
  • Centella asiatica commercially available as CentevitaTM
  • Cistus incanus (commercially available as RetorcylTM), or
  • the compound may be an isoflavone such as genistein (commercially available as Lipobelle Soyaglycone from Mibelle). Genistein may have chemical name 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one.
  • the isoflavone may be described in more detail in US2008/0299092, US2012/0195948, and US2014/0072619.
  • the compound is non-aromatic.
  • the compound maybe glyceryl glucoside.
  • Glyceryl glucoside has six hydroxyl groups.
  • the compound may be present in the composition in an amount ranging from 0.0001 wt % to 10 wt %, or 0.0003 wt % to 5 wt %, or 0.003 wt % to 3.5 wt % of the composition. In one embodiment the compound may be present at 0.1 wt % to 4 wt %, or 1 wt % to 3.5 wt % of the composition.
  • the compound is selected from the list consisting of a salt and/or derivative of hydroxymethionine (preferably a calcium salt of hydroxymethionine), genestein, a Centella asiatica extract, a Cistus incanus extract, a Polygonum bistorta extract and a Myrothamnus flabellifolia extract.
  • hydroxymethionine preferably a calcium salt of hydroxymethionine
  • genestein preferably a calcium salt of hydroxymethionine
  • Centella asiatica extract preferably a Centella asiatica extract
  • Cistus incanus extract a Polygonum bistorta extract
  • Myrothamnus flabellifolia extract preferably a calcium salt of hydroxymethionine
  • composition disclosed herein may optionally further comprise other ingredients.
  • the other ingredients include Hibiscus, a peptide, a matrix metalloproteinase inhibitor (MMPi), a whitening agent, a skin conditioning agent, a salicylic acid compound, a sunscreen agent, preservatives thickeners, viscosity modifying agents, and/or gelling agents sequestering agents, a wax, diluents, carriers, propellants perfumes, or pH adjusting agents.
  • MMPi matrix metalloproteinase inhibitor
  • a whitening agent e.g., a whitening agent
  • a skin conditioning agent e.g., a salicylic acid compound
  • sunscreen agent e.g., preservatives thickeners, viscosity modifying agents, and/or gelling agents sequestering agents, a wax, diluents, carriers, propellants perfumes, or pH adjusting agents.
  • the composition disclosed herein further comprises one or more of
  • Hibiscus a peptide, an MMPi and a whitening agent.
  • the Hibiscus may be Hibiscus sabdariffa, Hibiscus rosa sinensis or Hibiscus Abelmoschus. All three Hibiscus plants are known to form extracts used in cosmetic compositions.
  • the Hibiscus may be in the form of an extract.
  • Peptides are defined as compounds comprising an uninterrupted sequence of amino acids. For example the peptides are of natural origin. A dipeptide comprises an uninterrupted sequence of two amino acids.
  • Amino acids, as employed herein, include and encompass all of the naturally occurring amino acids, either in D or L configuration. Amino acids are commonly indicated with reference to the conventional three letter code and the sequence is read from left to right.
  • composition of the disclosed technology may comprise a dipeptide chosen from acetyl dipeptide 1 cetyl ester, acetyl dipeptide 3 aminohexanoate, azelaoyl bisdipeptide 10, coumaroyl dipeptide 3, dicetyl dipeptide 9, dipeptide diamino butyroyl benzylamide diacetate, dipeptide 1, dipeptide 10, dipeptide 11, dipeptide 12, dipeptide 15, dipeptide 16, dipeptide 17, dipeptide 18, dipeptide 19, dipeptide 2, dipeptide 20, dipeptide 3, dipeptide 4, dipeptide 5, dipeptide 6, dipeptide 7, dipeptide 8, dipeptide 8 HCL, dipeptide 9, hexanoyl dipeptide 3 norleucine acetate, methyl undecylenoyl dipeptide 16, nicotinoyl dipeptide 22, nicotinoyl dipeptide 23, nicotinoyl dipeptide 24, nicotinoyl dipeptide
  • the composition of the disclosed technology may comprise a tripeptide, or mixtures thereof.
  • the tripeptide may be naturally occurring or of synthetic origin. Suitable tripeptide compounds include tripeptide 1, 2, 3, 4, 5, 6, 7, 8, 9, 10,11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28 ,29, 30, 31, 32, 33, 34, 35, 36 ,37, 38, 39, 40, 41, 42, 43, 44, 45, 46, derivatives thereof, and mixtures thereof.
  • the tripeptide comprise one or more His-based tripeptides.
  • compositions of the disclosed technology may further comprise a tetrapeptide.
  • the tetrapeptide may be one or more rigin-based tetrapeptides, one or more ALAMCAT- tetrapeptides or mixtures thereof.
  • the tetrapeptide may be naturally occurring or of synthetic origin. Suitable tetrapeptides for use in the present composition include those chosen from tetrapeptide 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 34, 35, derivatives thereof and mixtures thereof.
  • Rigin-based tetrapeptides of the disclosed technology may be based on the structure Gly-Gln-Pro-Arg (Rigin) and include its analogues and derivatives thereof. Rigin is a typical tetrapeptide.
  • the compositions of the disclosed technology may further comprise a pentapeptide, derivatives of thereof, and mixtures thereof.
  • pentapeptide refers to both the naturally occurring pentapeptide and synthesized pentapeptide. Also useful herein are naturally occurring and commercially available compositions that comprise pentapeptides.
  • Suitable pentapeptides are those chosen from pentapeptide 1, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 25, 26, 28, 29, 30, 31, 33, 34, 35, 36, 38, 39, derivatives thereof and mixtures thereof.
  • the peptide when present in the composition disclosed herein may be present at 0 or 0.01% to 20%, or 0.05% to 15%, or 0.05 to 10 wt % of the composition.
  • Matrix Metalloproteinase Inhibitor The term "matrix metalloproteinase inhibitor” relates to all molecule and/or plant or bacterial extracts having an inhibitory activity on at least one of the matrix metalloproteinases expressed, synthetized, or activated by or in the skin.
  • the family of MMPis is formed of several well-defined groups on the basis of their resemblance regarding structure and substrate specificity (Woessner J. F., Faseb Journal, vol. 5, 1991, 2145).
  • the MMPi may be present at a level of from 0 or 0.01% to 10%, or 0.1% to 5% or
  • composition 0.25% to 2.5%, or 0.5% to 1% by weight of the composition.
  • the composition disclosed herein further comprises a whitening/lightening agent.
  • the composition further comprises the whitening/lightening agent it may be present at 0 or 0.001 to 10 wt %, or 0.01 to 5 wt %, or 0.1 to 2 wt %, or 0.2 to 1 wt % of the composition.
  • the whitening/lightening agent may be present at 0 or 0.001% to 3 wt %, or 0.01 to 2 wt%, or 0.05 to 1 wt %, or 0.1% to 0.5 wt % of the composition.
  • the whitening/lightening may include at least one of the following ingredients:
  • Emblica Mulberry leaf extract, mangostin, Sophora, a flavonoid, hydroxyphenoxy propionic acid and dimethylmethoxy chromanol.
  • the whitening/lightening agent may be a mixture of ingredients chosen from: Emblica and Sophora, optionally in the presence of Mulberry leaf extract.
  • the Mulberry leaf extract may be present.
  • the Emblica may be Emblica officinalis, for example comprising over 40% by weight (for example 50-80 wt %) of Emblicanin A.
  • Emblicanin B Pedunculagin and Punigluconin, and not more than about 1% by weight of flavonoids.
  • the Emblica may be phyllanthus Emblica.
  • the Sophora may be an extract of a small tree, and shrub in the pea family Fabaceae.
  • the Emblica may be phyllanthus Emblica and Sophora is derived from Sophora Angustifolia Root Extract.
  • the flavonoid species is believed to have antioxidant performance, and be an antioxidant plant polyphenolic agent.
  • antioxidant plant polyphenolic agent we mean a plant extract, or derivative thereof, comprising flavonoid species, including flavones, flavonols, flavanones, flavanols, anthrocyanidins and isoflavonoids; phenolic acid species; stilbenes; lignans and mixtures thereof, which provide an antioxidant benefit.
  • Antioxidant benefit is measured using the total antioxidant capacity (TAC) assay described herein. Plants provide a rich source of polyphenolic agents, and are therefore an efficient source of said antioxidants. Similar actives may be prepared synthetically and as such are analogues of said plant polyphenolic agents.
  • Antioxidant polyphenolic agents may include extracts from plants chosen from Mulberry (e.g. Morus alba), Ginseng (e.g. Panax ginseng), Raspberry, Oregano (e.g. Origanum vulgare), Green tea (e.g. green leaves of Camellia sinensis), White tea (e.g. Camellia sinensis), Blueberry extract (e.g. Vaccinium cyanococcus), French maritime pine bark (e.g. Pinus pinaster, sold under the trade name Pycnogenol), Rosemary (e.g.
  • Mulberry e.g. Morus alba
  • Ginseng e.g. Panax ginseng
  • Raspberry Oregano (e.g. Origanum vulgare)
  • Green tea e.g. green leaves of Camellia sinensis
  • White tea e.g. Camellia sinensis
  • Blueberry extract e.g. Vaccinium cyanococcus
  • French maritime pine bark e
  • Rosmarinus officialis Grape, including grape seed (e.g. Vitis vinifera), Fennel (e.g. Foeniculi fructus), Caragana sinica, Marjoram (e.g. Origanum majorana), Crocus (e.g. Crocus sativus), Apple (e.g. Malus domestica), Coffee, Green coffee, Cherry (e.g. Prunus avium), Snow algae (e.g. Chlamydomonas nivalis), Emblica (e.g. Phyllanthus emblica), Gingko (e.g. Gingko biloba), Moringa (e.g. Moringa oleilera), Ginger (e.g.
  • Magnolia e.g. Magnolioideae virginiana
  • French saffron Edelweiss (e.g. Leontopodium alpinium), White lotus (e.g. Nymphaea alba), Turmeric root, Marshmallow (e.g. Althaea officianlis), Burdock (e.g. Arctium lappa)
  • Bilberry e.g. Vaccinium myrtillus
  • Cranberry e.g. Vaccinium oxycoccus
  • Pomegranate nectar e.g. Punica granatum
  • Sage e.g. Salvia officinalis
  • Thyme e.g. Thymus vulgaris
  • Sunflower e.g.
  • wild carrot e.g. Daucus carota
  • Hop e.g. Humulus lupulus
  • Witch Hazel e.g. Hamamelis
  • Oak e.g. Quercus
  • Camellia e.g. Theacea
  • Red clover e.g. Trito
  • the antioxidant polyphenolic agent may be an extract from a plant chosen from mulberry, ginseng, grape, oregano, grape, sage, sunflower, maritime pine bark, rosemary, marjoram, crocus, firench saffron, wild carrot, hop, coffee, green coffee, witch hazel, oak, camellia, red clover, flax, ginger, magnolia, edelweiss, burdock and mixtures thereof.
  • Active polyphenolic species sourced from the above list of plants include those chosen from apigenin, luteolin, quercetin, kaempferol, naringenin, hesperetin, catechin, gallocatechin, cyaniding, pelargonidin, daidzein, caffeic acid, chlorogenic acid, romsmarinic acid, gallic acid, resveratrol, ferulic acid, epigallocatechin gallate, piceatannol, secoisolariciresinol, isotaxiresinol, Miyabenol c, Luteolin and mixtures thereof.
  • antioxidant plant polyphenolic agents used in the presently disclosed technology are expressed as dry weights of the extract, as understood by a man skilled in the art.
  • the antioxidant plant polyphenolic agent plant extract
  • the antioxidant plant polyphenolic agent may be present at 0.005 to 10 wt, or 0.01 to 7 wt %, or 0.01 to 5 wt % of the composition.
  • the chromane may be chosen from: methyl, di-, tri- and tetra- C1-C6 alkyl, C1-C6 alkoxy chromanol; pentamethyl chromanol, methyl, di, tri and tetra C1-C6 alkyl, C1-C6 alkoxy chromanyl C14-C20 ester and mixtures thereof.
  • the chromane may be chosen dimethyl methoxy chromanol, tetramethyl methoxy chromanol, pentamethyl chromanol, dimethyl methoxy chomanyl palmitate, dialkyl methoxy chomanyl myristate, dimethyl methoxy chromanyl stearate, dimethyl methoxy chomanyl oleate, dimethyl methoxy chomanyl linoleate and mixtures thereof.
  • the chromane may be dimethyl methoxy chromanol (commercially available under the trade name Lipochroman 6 as sold by Lipotec).
  • the composition disclosed herein may optionally comprise a skin conditioning agent.
  • the skin conditioning agents may be chosen from humectants, emollients, moisturisers, or mixtures thereof. Where present, the skin conditioning agent may be present from 0.01 to 20 wt %, or 0.1 to 10 wt %, or 0.5 to 7 wt % of the composition.
  • the skin conditioning agents may be chosen from guanidine, urea, glycolic acid and glycolate salts, salicylic acid, lactic acid and lactate salts, aloe vera, shea butter, polyhydroxy alcohols, such as sorbitol, mannitol, xylitol, erythritol, glycerol, hexanetriol, butanitriol, (di) propylene glycol, butylene glycol, hexylene glycol, polyethylene glycol, sugars (e.g.
  • fructose glucose, xylose, honey, mannose, xylose
  • gluconodeltalactone starches and their derivatives
  • pyrrolidone carboxylic acid, hyaluronic acid and salts thereof
  • lactamide monoethanolamine acetamide monoethanolamine
  • panthenol allantoin and mixtures thereof.
  • the skin conditioning agent may be chosen from glycerine, arabinoglactan, butylene glycol, hyaluronic acid, shea butter, propylene glycol, ethylhexyl glycerine, hyaluronate and mixtures thereof.
  • compositions disclosed herein may optionally comprise a salicylic acid compound, its esters, its salts, or combinations thereof.
  • a salicylic acid compound at 0.0001 to 25 wt %, or 0.001 to 15 wt %, or 0.01 to 10 wt %, or 0.1 to 5 wt %, and or 0.01 to 2 wt% of the composition, of salicylic acid.
  • the salicylic acid compound may be salicylic acid.
  • composition disclosed herein may optionally comprise a sunscreen component.
  • the sunscreen may comprise organic or inorganic sun filters or a combination of the two.
  • Suitable inorganic sunfilters include those chosen from microfme titanium dioxide, and microfme zinc oxide, and mixtures thereof.
  • Suitable organic sunscreens include those chosen from: a) p-aminobenzoic acids, their esters and derivatives (for example, 2-ethylhexyl p-dimethylaminobenzoate), b) methoxycinnamate esters (for example, 2-ethylhexyl p-methoxycinnamate, 2-ethoxyethyl p- methoxycinnamate or a, p-di- (p-methoxycinnamoyl)-a'- (2ethylhexanoyl)-glycerin, c) benzophenones (for example oxybenzone), d) dibenzoylmethanes such as 4- (tert-butyl)-4'- methoxydibenzoylmethane, e) 2-phenylbenzimidazole-5 sulphonic acid and its salts, f) alkyl- ss, ss-diphenylacrylates
  • sunscreen ingredients include those chosen from homosalate, Ethylhexyl salicylate, Diethylhexylbutamido triazone, Bis-ethylhexyloxyphenol methoxyphenyl triazine, Diethylamino hydroxybenzoyl hexyl benzoate, Butyl methoxydibenzoylmethane, Methylene bis-benzotriazoyl tetramethylbutylphenol, Polysilicone-15 and mixtures thereof.
  • a sunscreening agent may be present from 0 to 10 wt %, or 0.1 to 10 wt % of the composition.
  • compositions disclosed herein may also optionally comprise one or more of the following optional ingredients.
  • Preservatives may be added to the composition such as benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, 2-bromo2-nitropropane-l,3-diol (bronopol, which is available commercially under the trade name Myacide ®, benzyl alcohol, diazolidinyl urea, imidazolidinyl urea, methyl paraben, phenoxyethanol, ethyl paraben, propyl paraben, sodium methyl paraben, sodium dehydroacetate, polyhexamethylenebiguanide hydrochloride, isothiazolone and sodium propyl paraben and mixtures thereof, suitably in an amount of from 0.01 to 10 wt % of the composition.
  • Sequestering agents may be added to the composition, such as ethylenediamine tetraacetic acid and salts thereof, for example in an amount of from 0.005 to 0.5 wt % of the composition.
  • the composition may also include waxes such as cocoa butter suitably in an amount of from 0.1 to 10 wt % of the composition.
  • the composition may also comprise suitable, cosmetically acceptable diluents, carriers and/or propellants such as dimethyl ether.
  • the composition may also include pearlising agents such as stearic monoethanolamide and/or mica, suitably in an amount of from 0.01 to 10 wt % of the composition.
  • Perfumes may be added suitably in an amount of from 0.01 to 2 wt % of the composition, as may water soluble dyes such as tartrazine, suitably in an amount of from a trace amount such as lxl 0 "5 to 0.1 wt % of the composition.
  • the composition may also include pH adjusting agents such as sodium hydroxide, amino methyl propanol, triethanolamine, suitably in an amount of from 0.01 to 10 wt % of the composition.
  • the composition may be buffered by means well known in the art, for example by use of buffer systems comprising succinic acid, citric acid, lactic acid, and acceptable salts thereof, phosphoric acid, mono-or disodium phosphate and sodium carbonate.
  • the composition may have a pH between 3 and 10, between 4 and 8, or between 4.5 and 6.5.
  • composition of the disclosed technology does not contain a ascorbic acid derivative chosen from sodium ascorbyl phosphate, ascorbyl glycoside, L- ascorbic acid, ascorbyl palmitate, retinyl ascorbate, tetrahexyldecyl ascorbate, or magnesium ascorbyl phosphate.
  • a ascorbic acid derivative chosen from sodium ascorbyl phosphate, ascorbyl glycoside, L- ascorbic acid, ascorbyl palmitate, retinyl ascorbate, tetrahexyldecyl ascorbate, or magnesium ascorbyl phosphate.
  • composition of the disclosed technology does not include MMP compounds that comprise one hydroxyaryl or polyhydroxyaryl compound, or cyclic compounds having a cyclic group based upon a compound comprising a pyran, a lactam, or a piperidine constituent.
  • the cosmetically acceptable medium may be water, alcohol, or an oil. In one embodiment the cosmetically acceptable medium may include water and/or an oil.
  • the composition disclosed herein may be in the form of a gel or an emulsion.
  • the emulsion disclosed herein may be a water-in-oil, oil-in-water, or water-in-silicone composition, for example an oil-in-water or water-in-silicone composition, preferably oil-in-water.
  • the emulsion may comprise an oil phase and have an aqueous phase content of 30 to 85 wt %, or 40 to 80 wt %, or 50 to 75 wt % of the composition.
  • the emulsion may comprise an oil phase having 15 to 70 wt %, or 20 to 50 wt %, or 25 to 50 wt % of the composition.
  • the emulsion may be an oil-in- water composition comprising 15 to 70 wt % of an oil phase; and 30 to 85 wt % of an aqueous phase, or comprising 25 to 50 wt % of an oil phase; and 50 to 75 wt % of an aqueous phase.
  • the emulsion may be in the form of a water-in-silicone emulsion, and the water phase may be present at 30 to 85 wt % of an aqueous phase; and silicone present at 15 to 70 wt % of a silicone phase.
  • the emulsion may be in the form of a water-in-silicone emulsion, and the water phase may be present at 60 to 75 wt % of an aqueous phase; and silicone present at 25 to 40 wt % of a silicone phase.
  • composition disclosed herein is in the form of a water-in-silicone composition
  • oil phase may be provided by any suitable silicate, dimethiconols, silicone elastomer and mixtures thereof (for example a silicone elastomer).
  • the silicone oil phase may be formed from an organopolysiloxane.
  • the organopolysiloxane may be chosen from one or more of a polyalkylsiloxane, alkyl substituted dimethicone, cyclomethicone, trimethylsiloxysilicate, dimethiconol, polyalkylaryl siloxane, and mixtures thereof.
  • the polyalkylsiloxane may be for example a cyclomethicone, or dimethicone, for example a dimethicone.
  • a water-in-silicone composition disclosed herein may include an emulsifying crosslinked organopolysiloxane elastomer, a non-emulsifying crosslinked organopolysiloxane elastomer, or a mixture thereof.
  • non-emulsifying as used herein, defines crosslinked organopolysiloxane elastomers from which polyoxyalkylene units are absent.
  • the elastomers may include dimethyl polysiloxanes crosslinked by Si-H sites on a molecularly spherical MQ resin.
  • Emulsifying crosslinked organopolysiloxane elastomers include the crosslinked polymers described in US Patents 5,412,004; 5,837,793; and 5,811,487.
  • the emulsifying elastomer comprised of dimethicone copolyol crosspolymer (and) dimethicone is commercially available from Shin Etsu under the trade name KSG-21.
  • the non-emulsifying elastomers may include dimethicone crosspolymers.
  • dimethicone crosspolymers are supplied by a variety of suppliers including Dow Corning (EL9240).
  • Other dimethicones crosspolymer are available from General Electric (SFE 839), Shin Etsu (KSG-15, 16, 18 [dimethicone/phenyl vinyl dimethicone crosspolymer]), and Grant Industries (GRANSILTM line of elastomers).
  • Cross-linked organopolysiloxane elastomers useful in the composition disclosed herein and processes for making them are further described in US Patents 4,970,252; 5,760,116; and 5,654,362.
  • Commercially available elastomers typical for use herein are Dow Coming's 9040 silicone elastomer blend, Shin Etsu's KSG-21, and mixtures thereof.
  • An oil-in-water or water-in-oil emulsion may comprise an organic oil.
  • the organic oil may be volatile or non-volatile.
  • the organic oil may include a diluent, a solvent, a polyolefm polymer, or an ester oil.
  • ester oil means an oil that is liquid at room temperature (25 °C) comprising at least one ester functional group.
  • the ester oil used herein is chosen, for example, from monoesters.
  • the ester oil may, for example, be chosen from the monoesters of formula R ⁇ OOR 2 wherein R 1 may be selected from linear and branched hydrocarbon-based chains comprising from 4 to 30, or 6 to 24, or 7 to 20 carbon atoms carbon atoms, and R 2 may be chosen from branched hydrocarbon-based chains comprising from 3 to 40 carbon atoms, such as from 10 to 30 carbon atoms and further such as from 16 to 26 carbon atoms.
  • ester oils examples include isodecyl neopentanoate; isocetyl octanoate; isononyl isononanoate, isodecyl isononanoate, tridecyl isononanoate; hexyl laurate, 2-hexyldecyl laurate; isopropyl myristate, isocetyl myristate, isotridecyl myristate, 2- octyldodecyl myristate; isopropyl palmitate, 2-ethylhexyl palmitate, isooctyl palmitate, isocetyl palmitate, isodecyl palmitate, isostearyl palmitate, 2-octyldecyl palmitate; isopropyl isostearate, 2-octyldodecyl stearate, isostearyl isostearate, and 2-
  • the ester oil may be present in the emulsion disclosed herein in an amount ranging, for example, from 0 to 20 wt %, or 0.1 to 15 wt %, or 1 to 10 wt % of the composition.
  • Comparative Example 1 is a composition comprising 0.03 wt % of diospyros.
  • Comparative Example 2 is a composition comprising 0.03 wt % of a commercial product MEIRITAGETM (mixture of Astragalus Membranaceus Root Extract (and) Atractyloides Macrocephala Root Extract (and) Bupleurum Falcatum Root Extract).
  • Comparative Example 3 is a composition comprising 0.001 wt % of an Iris florentina root extract (commercially available as Iris Iso OPTM).
  • Liposome soy isoflavone (commercially available from Mibelle).
  • Example 2 is a composition comprising 0.001 wt % of a calcium salt of hydroxymethionine (commercially available as EssenskinTM ceramide from Sederma; and is a mixture comprising homotaurine and calcium salt of hydroxymethionine).
  • Example 3 is a composition comprising 0.003 wt % of a Centella asiatica extract
  • CentevitaTM Commercially available as CentevitaTM
  • Example 4 is a composition comprising 0.0003 wt % of a Cistus incanus extract (commercially available as RetorcylTM).
  • Example 5 is a composition comprising 0.03 wt % of a Polygonum bistorta extract (commercially available as PerlauraTM).
  • Example 6 is a composition comprising 0.001 wt % of a Myrothamnus flabellifolia extract (commercially available as MyramazeTM).
  • Example 7 is a composition comprising 0.001 wt % of a Glyceryl Glucoside.
  • the in vitro procedure uses a cell culture derived from human epidermal keratinocytes that have been cultured at 37 °C in 5 % carbon dioxide.
  • the culture medium is Keratinocyte-SFM supplemented with epidermal growth factor (0.25 ng/ml), pituitary extract (25 ⁇ g/ml, and gentamycin (25 ⁇ g/ml).
  • the culture assay medium is Keratinocyte-SFM supplemented with gentamycin (25 ⁇ g/ml).
  • the cell culture is then analysed for TGK expression.
  • the cells are seeded in 96-well plates and cultured for 24 hours in the culture medium.
  • the cells are then labelled using a primary antibody.
  • the primary antibody are then revealed using corresponding appropriate fluorescent secondary antibodies, and the cell nuclei are coloured using Hoescht solution 33258 (bis-benzimide) in parallel.
  • the primary antibody is anti -transglutaminase K (NOVUS Biologicals, refNB 100- 1844), and the secondary antibody is GAR-ELEXA 488 (Molecular Probes, ref Al 1008).
  • the fluorescence is measured by images (10 photos/well) using an INCell analyserTM1000 (from GE Healthcare).
  • the labelling is quantified by the measurement of fluorescence intensity normalised to the total number of cells (Integration of numerical data with the Developer Toolbox 1.5, GE Healthcare software).
  • the procedure measures changes in amount of transglutaminase.
  • the results obtained are presented below. Typically better results are obtained for examples having a higher percentage change in transglutaminase (TGK). The results obtained are:
  • Example 8 is an oil-in-water emulsion composition comprising approximately 50.3 wt % water, 4.1 wt % glycerine, 10 wt % dimethicone+dimethicone crosspolymer, 4.5 wt % hibiscus extract, 0.5 wt % hydrolysed rice protein, 3 wt % of Liposome soy isoflavone (commercially available from Mibelle), and 0.5 wt % of 3-ethyl ascorbic acid.
  • Example 9 is an oil-in-water emulsion composition comprising approximately 50.8 wt % water, 4.1 wt % glycerine, 10 wt % dimethicone+dimethicone crosspolymer, 4.5 wt % hibiscus extract, 0.5 wt % hydrolysed rice protein, 2.5 wt % of Essenskin ceramide (commercially available from Sederma and is a mixture of homotaurine and calcium salt of hydroxymethionine), and 0.5 wt % of 3-ethyl ascorbic acid.
  • Each example is prepared by blending and mixing oil phase ingredients and aqueous phase ingredients separately at a temperature of about 70 °C to ensure that all ingredients are solubilised in either water or oil. Once solubilised the oil phase and aqueous phase are blended at a temperature of about 70 °C until a homogenous emulsion composition is formed. Each example is then allowed to cool to ambient temperature.
  • EX8 and EX9 are evaluated by an 8 week in vivo split face/neck/decollete double blinded randomised controlled design on women aged 45 - 60 years old presenting with mild to advanced signs of ageing. Each example is applied twice a day over the designated randomised half side of the face, neck and decollete.
  • Anti-ageing efficacy is evaluated by the clinical grading of numerous facial features including crows-feet wrinkles, firmness, evenness of skin tone, photodamage, peri-oral wrinkles and forehead wrinkles.
  • composition of the disclosed technology has improved firmness, reduces photodamage, and reduces uneven skin tone of face, neck and decollete.

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Abstract

La technologie selon l'invention concerne une composition comprenant: un support cosmétiquement acceptable, un acide ascorbique O-substitué ou un dérivé de celui-ci; et un composé ayant deux groupes hydroxyle ou plus, le composé ayant une masse molaire d'au moins 150 g/mol et augmentant l'expression de la transglutaminase K dans des kératinocytes épidermiques. La technologie selon l'invention concerne également l'utilisation de la composition et une méthode d'amélioration de la fermeté de la peau, ou de réduction de l'affaissement cutané grâce à la composition.
PCT/EP2017/025183 2016-06-30 2017-06-27 Composition de soin de la peau et méthode associée Ceased WO2018001571A1 (fr)

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CN111154768A (zh) * 2020-01-16 2020-05-15 四川农业大学 一种密罗木基因MfbHLH15及其应用

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CN111118023A (zh) * 2020-01-16 2020-05-08 四川农业大学 一种密罗木基因MfbHLH38及其应用
CN111154768A (zh) * 2020-01-16 2020-05-15 四川农业大学 一种密罗木基因MfbHLH15及其应用
CN111154768B (zh) * 2020-01-16 2021-03-30 四川农业大学 一种密罗木基因MfbHLH15及其应用
CN111118023B (zh) * 2020-01-16 2021-03-30 四川农业大学 一种密罗木基因MfbHLH38及其应用

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