WO2020112590A1 - Extrait de centella asiatica solubilisé - Google Patents

Extrait de centella asiatica solubilisé Download PDF

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Publication number
WO2020112590A1
WO2020112590A1 PCT/US2019/062917 US2019062917W WO2020112590A1 WO 2020112590 A1 WO2020112590 A1 WO 2020112590A1 US 2019062917 W US2019062917 W US 2019062917W WO 2020112590 A1 WO2020112590 A1 WO 2020112590A1
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radical
formula
weight
hydrogen atom
compound
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PCT/US2019/062917
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English (en)
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Paul CHING
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Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic
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Publication of WO2020112590A1 publication Critical patent/WO2020112590A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • 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

Definitions

  • the present invention relates to compositions comprising polysorbates as solubilizing agents of hydrophobic compounds coming from Centella asiatica’s extracts into an aqueous medium, to cosmetic compositions for topical use comprising such compositions, and to methods for preventing the signs of aging of the skin, the scalp or the mucous membranes comprising a step of administering to a subject in need thereof an effective amount of the said composition or the said cosmetic composition.
  • Centella asiatica extracts have been widely described in the literature and more particularly titrated extract of Centella asiatica (known and commercialized under the trade name of TECA by the company SERDEX) [1] [2]
  • Such titrated extract of Centella asiatica contains asiaticoside, madecassic acid and asiatic acid as main coponents. These materials play a very important role in regulating normalization of skin connective tissues, especially fibroblasts and glycosaminoglycans, induce keratinocytes, and promote rapid and healthy growth of tissue components.
  • Such titrated extract of Centella asiatica (TECA) is used in the preparation of antiaging cosmetic preparation but it exhibits a very low solubility in water and therefore is very difficult for the preparation of water based cosmetic formulation.
  • US Patent application published under the number US2006106206A discloses method of extraction which makes it possible to obtain a mixture of madecassoside, of asiaticoside and of a molecule that has been called terminoloside, said mixture being more than 75 wt percent pure relative to the total weight of the mixture, and to obtain a mixture of madecassoside and of terminoloside, obtained more than 95 wt percent pure relative to the total weight of the mixture.
  • US2006106206A discloses an extract of Centella asiatica comprising a mixture of madecassoside, of terminoloside and, where appropriate, of asiaticoside.
  • US Patent application published under the number US2006106206A also discloses that the mixture of madecassoside and of terminoloside extracted from the parts of Centella asiatica that are above ground can be used in a drug for regulating inflammatory mechanisms.
  • the formulation of solution and emulsion comprising TECA may also comprise solvent, solubilizer and emulsifier, for example water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 ,3- butyleneglycol, oils, in particular cottonseed oil, groundnut oil, maize germ oil, olive oil, castor oil and sesame seed oil, glycerol fatty esters, polyethylene glycol and fatty acid esters of sorbitan or mixtures of these ingredients (US20081B1974 A2, paragraph [0079]).
  • solvent solubilizer and emulsifier
  • solubilizer and emulsifier for example water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 ,3- butylene
  • suspension may comprise liquid diluents, for example water, ethanol or propylene glycol, suspending agents, for example ethoxylated isosteary alcohols, polyoxyethylene sorbitol esters and poly oxyethylene sorbitan esters, micocrystalline cellulose, aluminum metahydroxide, bentonite, agar and tragacanth or mixtures of these ingredients (US2008181974A2, paragraph [0080]).
  • liquid diluents for example water, ethanol or propylene glycol
  • suspending agents for example ethoxylated isosteary alcohols, polyoxyethylene sorbitol esters and poly oxyethylene sorbitan esters, micocrystalline cellulose, aluminum metahydroxide, bentonite, agar and tragacanth or mixtures of these ingredients
  • Dong et al. discloses the use of a solvent mixture comprising dipropylene glycol, ethanol and purified water, whereas Polysorbates, and more particularly Polysorbate 80, are described as a surfactant to form the W1/0/ W2 emulsion and not as a solubilizing agent of TECA in water.
  • the European patent application published under the number EP 2428200 A2 relates to compositions to be used for the solubilization of hydrophobic substances in water, particularly in the solubilization of hydrophobic active agents that are of use in the field of cosmetics or pharmaceuticals.
  • Oil-soluble actives based upon a triterpenoid structure include natural extracts (for example from Centella asiatica, such as TECA, are described in EP 2428200 A2 as among the hydrophobic active agents difficult to solubilize in water and water phases.
  • EP 2428200 A2 discloses a solution for overcoming the problem of solubilizing hydrophobic active agents in water and water phases by providing a composition comprising a lipid and a surfactant which has an HLB number of less than 20, is an ether or ester surfactant or is an ionic surfactant.
  • EP 2428200 A2 The European patent application published under the number EP 2428200 A2 expressly discloses that a surfactant according to the invention is Polysorbate 20 (EP 2428200 A2, paragraphs [0100], [0122]) and that Polysorbate 80 is not a suitable surfactant for the invention (EP 2428200 A2, paragraphs [0278]
  • the Applicant has a found a new solubilization method to obtain a solution comprising a mixture of madecassoside, asiaticoside and a terminoloside.
  • a subject of the invention is a composition (C 1 ) for topical use comprising for 100% of its weight:
  • - R1 represents the hydrogen atom, a methyl radical (-CH 3 ), an ethyl radical (-C 2 H 5 ), a propyl radical (-C 3 H 7 ), an iso-propyl radical(-C 3 H 7 ) , a butyl radical (C 4 H 9 ), or an hydroxyl radical (-OH), and
  • - R2 represents the hydrogen atom, a methyl radical (-CH 3 ), an ethyl radical (-C 2 H 5 ), a propyl radical (-C 3 H 7 ), an iso-propyl radical(-C 3 H 7 ) , a butyl radical (C 4 H 9 ), or an hydroxyl radical (-OH), and
  • - R3 represents the hydrogen atom, a methyl radical (-CH3), an ethyl radical (-C 2 H 5 ), a propyl radical (-C 3 H 7 ), an iso-propyl radical(-C 3 H 7 ) , a butyl radical (C 4 H 9 ), or an hydroxyl radical (-OH), and
  • R4 represents the hydrogen atom, a methyl radical(-CH 3 ), or a glucosyl- glucosyl-rhamnosyl radical
  • Z 1 , Z2 and Z3, which may be identical or different, represent the hydrogen atom or the radical (R 1 C 0);
  • the weight ratio (Ra) between the at least compound of formula (I) and the at least compound of formula (II) is greater or equal to 0.02 and inferior or equal to 0.13.
  • composition (C 1 ) according to the invention is used by application to the skin, the hair, the scalp or the mucous membranes, whether it is a direct application or an indirect application, when for example the composition (C 1 ) according to the invention is incorporated into a support intended to be brought into contact with the skin (paper, wipe, textile, transdermal device, etc.).
  • the topical composition (C 1 ) according to the invention may be packaged in a bottle, and also in pressurized form in an aerosol device or in a device of "pump-action bottle” type, in a device equipped with a perforated wall, for example a grid, or in a device equipped with a ball applicator (termed “roll-on”).
  • a subject of the invention is a composition (C 1 ) as defined above, characterized in that it comprises for 100% of its weight:
  • composition (C 2 ) comprising for 100% by weight of
  • R1 represents the hydrogen atom
  • R2 represents the methyl radical
  • R3 represents the hydrogen atom
  • R4 represents the radical Glucosyl- glucosyl-rhamnosyl, and which can be representing by the formula (la)
  • R1 represents the hydroxyl radical (-OH)
  • R2 represents the methyl radical
  • R3 represents the hydrogen atom
  • R4 represents the radical Glucosyl- glucosyl-rhamnosyl, and which can be representing by the formula (lb)
  • R1 represents the hydroxyl radical (-OH)
  • R2 represents the hydrogen atom
  • R3 represents the methyl radical
  • R4 represents the radical Glucosyl-glucosyl-rhamnosyl, and which can be representing by the formula
  • R1 represents the hydrogen atom
  • R2 represents the methyl radical
  • R3 represents the hydrogen atom
  • R4 represents the hydrogen atom and which can be representing by the formula (Id):
  • R1 represents the hydroxyl radical (-OH)
  • R2 represents the methyl radical
  • R3 represents the hydrogen atom
  • R4 represents the hydrogen atom and which can be representing by the formula (le)
  • composition (C 1 ) as defined above, characterized in that composition (C 2 ) comprises for 100% of its weight:
  • composition (C 1 ) as defined above, characterized in that composition (C 2 ) comprises for 100% of its weight: 30% to 50% by weight of the compound of formula (la)
  • a second object of the present invention is the use of a composition represented by formula (II):
  • solubilizing agent in an aqueous composition of at least one compound of formula (I)
  • R1 represents the hydrogen atom, a methyl radical (-CH 3 ), an ethyl radical (-C 2 H 5 ), a propyl radical (-C 3 H 7 ), an iso-propyl radical(-C 3 H 7 ) , a butyl radical (C 4 H 9 ), or an hydroxyl radical (-OH)
  • R2 represents the hydrogen atom, a methyl radical (-CH 3 ), an ethyl radical (-C 2 H 5 ), a propyl radical (-C 3 H 7 ), an iso-propyl radical(-C 3 H 7 ) , a butyl radical (C 4 H 9 ), or an hydroxyl radical (-OH)
  • R2 represents the hydrogen atom, a methyl radical (-CH 3 ), an ethyl radical (-C 2 H 5 ), a propyl radical (-C 3 H 7 ), an iso-propyl radical(-C 3 H 7 ) , a butyl radical
  • R3 represents the hydrogen atom, a methyl radical (-CH3), an ethyl radical (-C 2 H 5 ), a propyl radical (-C 3 H 7 ), an iso-propyl radical(-C 3 H 7 ) , a butyl radical (C 4 H 9 ), or an hydroxyl radical (-OH), and
  • R4 represents the hydrogen atom, a methyl radical(-CH 3 ), or a glucosyl-glucosyl- rhamnosyl radical.
  • a subject of the invention is the use of a composition represented by formula (II) as defined above, characterized in that the at least one compound of formula (I) is a composition (C2) comprising for 100% of its weight: bi) 20% to 80% by weight of at least one compound selected among the members of the group consisting in the compounds of formula (I) for which:
  • R1 represents the hydrogen atom
  • R2 represents the methyl radical
  • R3 represents the hydrogen atom
  • R4 represents the radical Glucosyl- glucosyl-rhamnosyl, and which can be representing by the formula (la)
  • R1 represents the hydroxyl radical (-OH)
  • R2 represents the methyl radical
  • R3 represents the hydrogen atom
  • R4 represents the radical Glucosyl- glucosyl-rhamnosyl, and which can be representing by the formula (lb)
  • R1 represents the hydroxyl radical (-OH)
  • R2 represents the hydrogen atom
  • R3 represents the methyl radical
  • R4 represents the radical Glucosyl-glucosyl-rhamnosyl, and which can be representing by the formula
  • R1 represents the hydrogen atom
  • R2 represents the methyl radical
  • R3 represents the hydrogen atom
  • R4 represents the hydrogen atom and which can be representing by the formula (Id):
  • R1 represents the hydroxyl radical (-OH)
  • R2 represents the methyl radical
  • R3 represents the hydrogen atom
  • R4 represents the hydrogen atom and which can be representing by the formula (le)
  • a subject of the invention is the use of at least one compound of formula (I) which is a composition (C2) comprising for 100% of its weight:
  • a subject of the invention is the use of at least one compound of formula (I) which is a composition (C2) comprising for 100% of its weight:
  • the composition (C 1 ) according to the invention is prepared by mixing its constituents, with mechanical stirring, at a stirring speed of between 50 revolutions/minute and 500 revolutions/minute, more particularly between 50 revolutions/minute and 100 revolutions/minute, at a temperature of between 20 degrees centigrade and 85 degrees centigrade, more particularly between 20 degrees centigrade and 60 degrees centigrade, and even more particularly between 20 degrees centigrade and 45 degrees centigrade
  • composition (C 2 ) according to the invention can be prepared by mixing its constituents, with mechanical stirring, at a stirring speed of between 50 revolutions/minute and 500 revolutions/minute, more particularly between 50 revolutions/minute and 100 revolutions/minute, at a temperature of between 20 degrees centigrade and 85degrees centigrade, more particularly between 20 degrees centigrade and 60 degrees centigrade, and even more particularly between 20 degrees centigrade and 45 degrees centigrade
  • composition (C 2 ) according to the invention can also be prepared by extraction of Centella asiatica’s parts that are above ground, and adjusted by incorporation of water and/or of compound of formula (II).
  • Another object of the present invention is a cosmetic composition (C3) for topical use comprising at least a cosmetically acceptable excipient (E) and an effective amount of composition (C1) as defined here above.
  • the expression "cosmetically acceptable" used in the definition of the cosmetic formulation such as described above means that said formulation comprises any substance or preparation that is intended to come into contact with various parts of the human body (epidermis, hair and capillary system, nails, lips and genitals) or with the teeth or with mouth mucous membranes, exclusively and mainly with the aim of cleaning them, perfuming them, modifying the appearance and/or modifying body odors and/or protecting them or to keep them in good condition.
  • the cosmetic composition (C 3 ) for topical use according to the invention generally comprises cosmetically acceptable excipient (E) normally used in the field of formulations for topical use, which are in particular cosmetic, dermocosmetic, pharmaceutical or dermopharmaceutical, such as foaming and/or detergent surfactants, thickening and/or gelling surfactants, thickeners and/or gelling agents, stabilizers, film-forming compounds, solvents and cosolvents, hydrotropic agents, plasticizers, emulsifiers and coemulsifiers, opacifiers, nacreous agents, overfatting agents, sequestering agents, chelating agents, oils, waxes, sunscreens, mineral fillers or pigments, particles which provide a visual effect or which are intended for encapsulating active agents, texturing agents, optical brighteners, and insect repellents.
  • cosmetically acceptable excipient (E) normally used in the field of formulations for topical use, which are in particular cosmetic, dermocosmetic, pharmaceutical or dermo
  • foaming and/or detergent surfactants optionally present in the cosmetic composition (C 3 ) for topical use according to the invention, mention may be made of anionic, cationic, amphoteric or nonionic foaming and/or detergent surfactants.
  • anionic foaming and/or detergent surfactants that can be used in the cosmetic composition (C 3 ) for topical use according to the invention, mention may be made of alkali metal salts, alkaline earth metal salts, ammonium salts, amine salts or amino alcohol salts of alkyl ether sulfates, alkyl sulfates, alkylamido ether sulfates, alkylarylpolyether sulfates, monoglyceride sulfates, alpha-olefin sulfonates, paraffin sulfonates, alkyl phosphates, alkyl ether phosphates, alkyl sulfonates, alkylamide sulfonates, alkylaryl sulfonates, alkyl carboxylates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl, al
  • amphoteric foaming and/or detergent surfactants that can be used in the cosmetic composition (C 3 ) for topical use according to the invention, mention may be made of alkyl betaines, alkylamido betaines, sultaines, alkylamidoalkyl sulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates.
  • cationic foaming and/or detergent surfactants that can be used in the cosmetic composition (C 3 ) for topical use according to the invention, mention may particularly be made of quaternary ammonium derivatives.
  • nonionic foaming and/or detergent surfactants that can be used in the cosmetic composition (C 3 ) for topical use according to the invention
  • alkyl polyglycosides comprising a linear or branched, and saturated or unsaturated aliphatic radical, comprising from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside, dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1 ,12-dodecanediyl polyglucoside; ethoxylated derivatives of hydrogenated castor oil, such as the product sold under the I NCI name "Peg-40 hydrogenated castor oil"; coconut amides; or N- alkylamines.
  • thickening and/or gelling surfactants optionally present in the cosmetic composition (C 3 ) for topical use according to the invention
  • alkoxylated alkyl polyglucoside fatty esters for instance ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate sold respectively under the names GlucamateTM LT and GlumateTM DOE120; alkoxylated fatty esters such as PEG 150 pentaerythrytyl tetrastearate sold under the name CrothixTM DS53, PEG 55 propylene glycol oleate sold under the name AntilTM 141 ; fatty-chain polyalkylene glycol carbamates, for instance PPG-14 laureth isophoryl dicarbamate sold under the name ElfacosTM T211 , or PPG-14 palmeth-60 hexyl dicarbamate sold under the name ElfacosTM GT
  • thickeners and/or gelling agents optionally present in the cosmetic composition (C 3 ) for topical use according to the invention
  • the linear or branched or crosslinked polymers of polyelectrolyte type optionally present in the topical composition according to the invention may be in the form of a solution, an aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, or a powder.
  • the linear or branched or crosslinked polymers of polyelectrolyte type optionally present in the topical composition according to the invention can be selected from the products sold under the names SimulgelTM EG, SimulgelTMEPG, SepigelTM 305, SimulgelTM 600, SimulgelTM NS, SimulgelTM INS 100, SimulgelTM FL, SimulgelTM A, SimulgelTM SMS 88, SepinovTMEMT 10, SepiplusTM400, SepiplusTM265, SepiplusTMS, AristoflexTMAVC, AristoflexTMAVS, NovemerTM EC-1 , FlocareTMET 25, FlocareTMET 75, FlocareTMET 26, FlocareTMET 30, FlocareTMET 58, FlocareTMPSD 30, ViscolamTMAT 64, ViscolamTMAT 100.
  • thickeners and/or gelling agents optionally present in the cosmetic composition (C 3 ) for topical use according to the invention
  • thickeners and/or gelling agents optionally present in the cosmetic composition (C 3 ) for topical use according to the invention
  • monosaccharide derivatives such as sulfated galactans and more particularly carrageenans and agar, uronans and more particularly algins, alginates and pectins, heteropolymers of monosaccharides and of uronic acids and more particularly xanthan gum, gellan gum, exudates of gum Arabic and of karaya gum, and glucosaminog
  • the cosmetic composition (C 3 ) for topical use according to the invention can also comprise at least one polysaccharide chosen from the group consisting of a galactomannan, gum Arabic and xanthan gum, the weight ratio between said polysaccharide and the anionic polyelectrolyte according to the invention is greater than or equal to 1 /3 and less than or equal to 3/1 , more particularly or equal to 1 12 and less than or equal to 3/2.
  • the combination of the polysaccharide, as defined above, and of the anionic polyelectrolyte according to the invention makes it possible to obtain topical compositions according to the invention which are in the form of salt-rich emulsions, retaining a high viscosity and a uniform appearance after a prolonged storage period.
  • Such topical compositions according to the invention can comprise, for 100 percent of their weight, from 0.1 percent to 25 percent by weight of at least one salt and can have a dynamic viscosity measured at 20 degrees centigrade, by means of a Brookfield viscometer, of greater than or equal to 30 000 mPa.s and less than or equal to 200 000 mPa.s.
  • thickeners and/or gelling agents optionally present in the cosmetic composition (C3) for topical use according to the invention mention may be made of cellulose, cellulose derivatives such as methylcellulose, ethyl-cellulose or hydroxypropyl cellulose, silicates, starch, hydrophilic starch derivatives, and polyurethanes.
  • stabilizers optionally present in the cosmetic composition (C 3 ) for topical use according to the invention mention may be made, for example, of microcrystalline waxes, and more particularly ozokerite, inorganic salts such as sodium chloride or magnesium chloride, and silicone polymers such as polysiloxane polyalkyl polyether copolymers.
  • solvents optionally present in the cosmetic composition (C 3 ) for topical use according to the invention mention may be made of water, organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1 ,3-propanediol, 1 ,2-propanediol, hexylene glycol, diethylene glycol, xylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol, isopropanol or butanol, and mixtures of water and said organic solvents.
  • organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1 ,3-propanediol, 1 ,2-propanediol, hexylene glycol, diethylene glycol, xylitol,
  • spring or mineral waters having a mineralization of at least 300 mg/I, in particular Avene water, Vittel water, waters from the Vichy basin, Uriage water, Roche Posay water, Bourboule water, Enghien-les-bains water, Saint- Gervais-les bains water, Neris-les-bains water, Allevard-les-bains water, Digne water, Maizieres water, Neyrac-les-bains water, Lons le Saunier water, Rochefort water, Saint Christau water, Fumades water and Tercis- les-bains water.
  • hydrotropic agents optionally present in the cosmetic composition (C 3 ) for topical use according to the invention, mention may be made of the xylene sulfonates, cumene sulfonates, hexylpolyglucoside, 2-ethylhexylpolyglucoside and n- heptylpolyglucoside.
  • emulsifying surfactants optionally present in the cosmetic composition (C3) for topical use according to the invention, mention may be made of nonionic surfactants, anionic surfactants and cationic surfactants.
  • nonionic emulsifying surfactants optionally present in the cosmetic composition (C3) for topical use according to the invention
  • fatty acid esters of sorbitol for instance the products sold under the names MontaneTM40, MontaneTM60, MontaneTM70, MontaneTM80 and MontaneTM85
  • compositions comprising glyceryl stearate and stearic acid ethoxylated at between 5 mol and 150 mol of ethylene oxide, for instance the composition comprising stearic acid ethoxylated at 135 mol of ethylene oxide and glyceryl stearate sold under the name SimulsolTM 165
  • mannitan esters ethoxylated mannitan esters
  • sucrose esters methylglucoside esters
  • alkyl polyglycosides comprising a linear or branched and saturated or unsaturated aliphatic radical, comprising from 14 to 36 carbon atoms, such as tetradec
  • cationic emulsifier surfactants optionally present in the cosmetic composition (C 3 ) for topical use according to the invention, mention may be made of amine oxides, quatemium-82 and the surfactants described in patent application WO 96/00719 and mainly those in which the fatty chain comprises at least 16 carbon atoms.
  • opacifiers and/or nacreous agents optionally present in the cosmetic composition (C 3 ) for topical use according to the invention, mention may be made of sodium palmitate, sodium stearate, sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, and fatty alcohols comprising from 12 to 22 carbon atoms.
  • N-acylated derivatives of amino acids such as the lauroyl lysine sold under the name AminohopeTMLL, the octenyl starch succinate sold under the name DryfloTM, the myristyl polyglucoside sold under the name MontanovTM 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite and mica.
  • deodorants optionally present in the cosmetic composition (C 3 ) for topical use according to the invention, mention may be made, for example, of alkali metal silicates, zinc salts such as zinc sulfate, zinc gluconate, zinc chloride or zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glyceryl caprate, glyceryl caprylate, polyglyceryl caprate; 1 ,2- decanediol; 1 ,3- propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metal zeolites; TriclosanTM; aluminum bromohydrate, aluminum chlorohydrates, aluminum chloride, aluminum sulfate, aluminum zirconium chlorohydrates, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pen
  • oils optionally present in the cosmetic composition (C 3 ) for topical use according to the invention mention may be made of mineral oils such as paraffin, liquid petroleum jelly, isoparaffins or white mineral oils; oils of animal origin, such as squalene or squalane; vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheatgerm oil, com germ oil, soybean oil, cottonseed oil, alfafa oil, poppyseed oil, pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, safflower oil, candlenut oil, passion flower oil, hazelnut oil, palm oil, shea butter, apricot kernel oil, beauty leaf oil, sysymbrium oil, avocado oil, calendula oil, oils derived from flowers or from vegetables, ethoxylated vegetable oils; synthetic oils, for instance fatty acid esters such as butyl my
  • oils is intended to mean, in the present application, compounds and/or mixtures of compounds which are insoluble in water and which have a liquid aspect at a temperature of 25 degrees centigrade
  • waxes is intended to mean, in the present application, compounds and/or mixtures of compounds which are insoluble in water and which have a solid aspect at a temperature greater than or equal to 45 degrees centigrade.
  • antioxidants that may be present within the cosmetic composition (C3) for topical use according to the invention, mention may be made of EDTA and salts thereof, citric acid, tartaric acid, oxalic acid, BHA (butyl hydroxyanisole), BHT (butyl hydroxytoluene), tocopherol derivatives such as tocopheryl acetate, mixtures of antioxidant compounds such as DissolvineTM GL 47S sold by the company Akzo Nobel under the I NCI name: Tetrasodium glutamate diacetate.
  • sunscreens that may be present within the cosmetic composition (C3) for topical use according to the invention, mention may be made of all those featured in the cosmetic directive 76/768/EEC amended annex VII.
  • organic sunscreens that may be present within the cosmetic composition (C 3 ) for topical use according to the invention, mention may be made of the family of benzoic acid derivatives for instance para-aminobenzoic acids (PABA), especially monoglyceryl esters of PABA, ethyl esters of N,N-propoxy PABA, ethyl esters of N,N-diethoxy PABA, ethyl esters of N,N-dimethyl PABA, methyl esters of N,N-dimethyl PABA and butyl esters of N,N-dimethyl PABA; the family of anthranilic acid derivatives, for instance homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives, for instance amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate and p-isopropanolphenyl salicy
  • mineral sunscreens also known as “mineral sunblocks", which may be that may be present within the cosmetic composition (C 3 ) for topical use according to the invention, mention may be made of titanium oxides, zinc oxides, cerium oxide, zirconium oxide, yellow, red or black iron oxides, and chromium oxides.
  • mineral sunblocks may or may not be micronized, may or may not have undergone surface treatments and may be optionally in the form of aqueous or oily pre-dispersions.
  • Another object of the present invention is a method for preventing the signs of aging of the skin, the hair, the scalp or the mucous membranes, comprising a step of administering to a subject in need thereof an effective amount of the composition (C 1 ) as defined above, or an effective amount of the composition (C 3 ) as defined above.
  • the term "effective amount of compound of the composition (C 1 ) as defined previously means, per 100 percent of the mass of said cosmetic formulation for topical use, the amount between 0.1 percent and 5 percent by mass, more particularly between 0.1 percent and 3 percent by mass and even more particularly between 0.5 percent and 2 percent by mass of composition (C 1 ).
  • the term "effective amount of compound of the composition (C 3 ) as defined previously means the amount between 10 grams and 1 gram for a body lotion, or the amount between 1 gram and 0.1 gram for a face lotion, during at least 15 days.
  • the term “signs of aging of human skin” means any change in the outer appearance of the skin due to aging, whether these be chrono- biological and/or photo-induced and/or resulting from exposure to environmental stresses (atmospheric pollution, contact with hazardous substances), such as wrinkles and fine lines, impairment of the micro-relief, lack of elasticity and/or tonicity of the skin, lack of density and/or firmness of human skin or the lips, but also any internal modification of the skin that is not automatically reflected by a modified outer appearance, such as any internal degradation of the skin consecutive to exposure to ultraviolet rays.
  • Another object of the present invention is a method for preventing the unattractive effects related to skin and/or scalp inflammation, and treating tingling and / or itching and / or redness and / or skin discomfort and / or tightness of the skin characterized in that it comprises at least one step a1) of application onto the surface of the skin to be treated, of an effective amount of a composition for topical use (C3) comprising at least one cosmetically acceptable excipient (E) and a composition (C1), as defined above.
  • a composition for topical use C3 comprising at least one cosmetically acceptable excipient (E) and a composition (C1), as defined above.
  • Another object of the present invention is a pharmaceutical composition (C 3 ) for topical use comprising at least a pharmaceutical acceptable excipient (E) and an effective amount of composition (C 1 ) as defined above for its use in a therapeutic method.
  • a subject of the invention is a pharmaceutical composition (C3) for topical use as defined above characterized in that the said therapeutic method is intended for the treatment of autoimmune diseases, chronic inflammatory diseases, atopic inflammatory diseases, bowel diseases, wound healing.
  • TECA used for the purposes of this evaluation comprises for 100% of its weight:
  • the temperature is regulated at 85 degrees centigrade with a magnetized magnetic bar stirring at a speed of 80 revolutions/min for a period of 30 minutes. At the end of this period, the visual appearance obtained is noted at To, D7, M1 , M3 and 3 F/T cycles at -5C/+40C.
  • Polysorbate 80 as a solubilizing agent allows to solubilize the TECA in amount of 0.1 %, 0.5% and 1% in water, whereas it is not possible to solubilize the 0.1 % of TECA with the same amounts (1 %, 3%) of Polysorbate 20 and Polysorbate 60.
  • Other known solubilizers do not allow to obtain the solubilization performances obtained with Polysorbate 80 to solubilize TECA in water.
  • TECA Asiaticoside (and) Madecassic Acid (and) Asiatic Acid
  • Centella asiatica provides wound healing improvement and collagen synthesis stimulation, antibacterial effect, microcirculation activation and cellulite reduction.
  • MontanovTM202 (INCI Name: arachidyl alcohol, behenyl alcohol and arachidyl glucoside) is a self-emulsifiable composition, such as those described in EP 0 977 626, sold by Seppic.
  • EmogreenTML19 (INCI Name: C15-19 Alkane) is a composition used as emollient for the preparation of cosmetic formulation, and commercialized by SEPPIC.
  • DUB 810C (INCI Name: Coco-Caprylate/Caprate) is a composition used as emollient for the preparation of cosmetic formulation, and commercialized by DUBOIS.
  • SepinovTMWEO (INCI Name: Hydroxyethyl Acrylate/Sodium Acryloyldimethyl Taurate Copolymer) used as an emulsifier/stabilizer, and/or thickener for the preparation of cosmetic formulation, and commercialized by SEPPIC.
  • AquaxylTM (INCI Name: Xylitylglucoside (and) Anhydroxylitol (and) Xylitol) is a moisturizing agent for the preparation of cosmetic formulation, and commercialized by SEPPIC.
  • EuxylTM PE9010 (I NCI Name: Phenoxyethanol (and) Ethylhexylglycerin) is a liquid cosmetic preservative commercialized by the company Schülke & Mayr
  • SepimaxTMZen (INCI Name: INCI: Polyacrylate Crosspolymer-6) is a polymeric thickener used for the preparation of cosmetic formulation, and commercialized by SEPPIC.

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Abstract

L'invention concerne des compositions comprenant des polysorbates, en particulier du polysorbate 80, en tant qu'agents permettant la solubilisation en milieu aqueux de composés hydrophobes provenant d'extraits de Centella asiatica. Des compositions cosmétiques destinées à une utilisation topique comprennent de telles compositions. Des méthodes pour prévenir les signes de vieillissement de la peau, du cuir chevelu ou des muqueuses, ou pour prévenir ou traiter des effets liés à une inflammation, des picotements, des démangeaisons, un rougissement, un inconfort et/ou une tension de la peau et/ou du cuir chevelu, comprennent une étape d'administration au patient le nécessitant d'une quantité efficace des compositions. Des compositions pharmaceutiques comprenant les compositions peuvent être utilisées pour traiter des maladies auto-immunes, des maladies inflammatoires chroniques, des maladies inflammatoires atopiques et des maladies intestinales, et pour la cicatrisation des plaies. Les composés hydrophobes comprennent l'asiaticoside, le madécassoside, le terminoloside, l'acide asiatique et l'acide madécassique.
PCT/US2019/062917 2018-11-27 2019-11-25 Extrait de centella asiatica solubilisé WO2020112590A1 (fr)

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Cited By (1)

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CN114732937A (zh) * 2022-05-20 2022-07-12 斯贝福（北京）生物技术有限公司 一种用于动物耳软骨支撑材料的敷料及其制备方法和应用

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114732937A (zh) * 2022-05-20 2022-07-12 斯贝福（北京）生物技术有限公司 一种用于动物耳软骨支撑材料的敷料及其制备方法和应用

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