EP2293788A2 - Nouvelles compositions dépigmentantes sous forme d'une composition anhydre sans vaseline et sans élastomère comprenant un dérivé phénolique solubilisé et un rétinoïde - Google Patents

Nouvelles compositions dépigmentantes sous forme d'une composition anhydre sans vaseline et sans élastomère comprenant un dérivé phénolique solubilisé et un rétinoïde

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Publication number
EP2293788A2
EP2293788A2 EP09769516A EP09769516A EP2293788A2 EP 2293788 A2 EP2293788 A2 EP 2293788A2 EP 09769516 A EP09769516 A EP 09769516A EP 09769516 A EP09769516 A EP 09769516A EP 2293788 A2 EP2293788 A2 EP 2293788A2
Authority
EP
European Patent Office
Prior art keywords
composition
composition according
retinoid
oil
hydroquinone
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.)
Withdrawn
Application number
EP09769516A
Other languages
German (de)
English (en)
French (fr)
Inventor
Claire Mallard
Karine Nadau-Fourcade
Fabienne Louis
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.)
Galderma Research and Development SNC
Original Assignee
Galderma Research and Development SNC
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Filing date
Publication date
Application filed by Galderma Research and Development SNC filed Critical Galderma Research and Development SNC
Publication of EP2293788A2 publication Critical patent/EP2293788A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/203—Retinoic acids ; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin

Definitions

  • Novel depigmenting compositions in the form of an anhydrous composition without vaseline and without elastomer comprising a solubilized phenolic derivative and a retinoid.
  • the present invention relates to a novel cosmetic or pharmaceutical depigmenting composition in the form of an anhydrous ointment not containing petroleum jelly and without elastomer, in particular for topical application, comprising, as pharmaceutical active ingredients, a solubilized phenolic derivative and a retinoid.
  • phenolic derivatives and more particularly polyphenols remain, for decades, among the most effective active.
  • the therapeutic use of these agents results from the observation of skin depigmentation in workers in the rubber industry where some of these products are used as antioxidants. Since then, numerous studies have only confirmed their efficacy alone or in combination with other depigmenting agents [Jorge L. Sanchez, M.D. and Miguel Vazquez, M. International Journal of Dermatology Jan.-Feb 1982 vol 21 p55 58]. They thus appear as virtually inescapable assets in the treatment of hyperpigmentation and are therefore present in many commercial products.
  • hydroquinone is the most used pharmaceutical active ingredients.
  • Hydroquinone has been the subject of various patent applications, and in particular US Pat. No. 3,856,934, in which hydroquinone is in combination with retinoic acid and a corticosteroid as depigmenting composition.
  • Rucinol or lucinol, or 4-butyl-resorcinol is a phenol derivative pharmaceutical active agent, polyphenol type marketed as agent for lightening brown spots related to pigmentation disorders (product Iklen ®).
  • hydroquinone, the rucinol or their salts or its derivatives are solubilized in the aqueous phase of the preparation.
  • reducing agents are used to combat this degradation, in particular sulfites, which are almost unavoidable.
  • these antioxidants have a number of disadvantages such as skin irritation problems, odor in the formulations or destabilization of the formula related to a loss of viscosity.
  • Hydroquinone because of its high concentration of irritating effect can cause post-inflammatory hypermelanosis and ochronosis phenomena.
  • hydroquinone Treatment with hydroquinone may be accompanied by irritation that may lead to post-inflammatory hyperpigmentation.
  • the incidence of irritation depends on the hydroquinone concentration. The latter is quite important for the 10% concentrations and strongly decreases for the 5% preparations and would be practically nil at the 2% concentration ["The chemical depigmenting agents" JP. Ortonne Ann. Dermatol. Venerol. 1986, 13: 733-736].
  • the galenic chosen can therefore play a leading role in minimizing these effects.
  • the phenolic derivative pharmaceuticals and in particular hydroquinone or rucinol in solubilized form should be formulated in a formulation to avoid the presence of sulfites and / or to suppress or limit the use of antioxidants.
  • anhydrous composition without petroleum jelly and without elastomer has a sufficiently high viscosity.
  • compositions currently available on the market, or as described in the application US2006 / 0120979 and allowing the formulation of active principles sensitive to water, while ensuring a good chemical stability are generally ointment-type compositions made up mainly of petroleum jelly or, in more recent formulations of a large part of elastomer.
  • the use of petrolatum is not satisfactory for the following reasons: after application, certain compositions comprising petroleum jelly are perceived as sticky and greasy, and are brighter; moreover, the preparation of compositions in the form of ointments based on petroleum jelly requires particular compounds and conditions. Indeed, vaseline is solid at room temperature, and has a melting point of greater than 40 ° C.
  • elastomer in a relatively large amount makes it possible to give a certain viscosity to anhydrous formulations (patent US2006 / 0120979) without the disadvantages of petroleum jelly.
  • elastomer in the present invention, its use is not satisfactory for the following reasons: the high proportion of elastomer present in these formulations prevents the incorporation of sufficient quantities of oily and waxy compounds having the advantage of conferring the preparation the desired emollient properties.
  • One of the aims of the present invention is to provide an anhydrous pharmaceutical composition without vaseline and without elastomer, intended for topical application, which has a viscosity equivalent to that of ointments containing vaseline, which is easy to prepare, which ensures good chemical stability of the actives and in which certain volatile compounds can be used.
  • the composition according to the invention has in particular these advantages thanks to its preparation process.
  • the invention therefore also relates to the particularly advantageous method of preparation of such a composition, wherein the step of incorporating the active ingredients is carried out at room temperature.
  • the desired viscosity of the composition according to the invention is obtained, in particular by means of the choice of the fatty substances used.
  • Another object of the present invention is to provide an anhydrous pharmaceutical composition without vaseline and without elastomer for topical application having a prolonged stability, allowing optimized release of the active ingredients while being very well tolerated.
  • the present invention thus relates to a novel stable composition in the form of an anhydrous composition containing no petrolatum and without elastomer, especially for topical application, comprising, as pharmaceutical active ingredients, a phenol derivative of the solubilized polyphenol type and a retinoid.
  • the anhydrous composition according to the present invention also has both excellent stability and safety.
  • elastomer polyorganosiloxane elastomer.
  • anhydrous composition is meant a composition comprising a quantity of water less than or equal to 5% by weight relative to the total weight of the composition.
  • the composition does not contain water.
  • stable composition is meant a chemically and physically stable composition.
  • chemical stability it is meant in particular that no degradation of the active substance is observed over time and at temperatures of between 4 and 40 ° C.
  • physical stability it is meant in particular that the compositions do not exhibit a fall in viscosity over time and at temperatures between 4 and 40 ° C.
  • the object of the present invention is thus an anhydrous pharmaceutical composition, characterized in that it comprises: a. at least one first phenolic derivative pharmaceutical active agent, b. at least one second retinoid-type pharmaceutical active agent, c. glyceryl behenate, its derivatives or mixtures thereof, d. at least one solvent of the phenolic derivative, said composition containing neither petroleum jelly nor polyorganosiloxane elastomer.
  • the anhydrous composition according to the invention may be in the various known galenic forms which the person skilled in the art will adapt to the particular use of the composition.
  • compositions according to the invention are preferably formulated for topical application.
  • topical means an external application on the skin or mucous membranes.
  • compositions according to the invention may be in any of the galenical forms normally used for topical administration.
  • the compositions as described in the pharmacopoeias USP32-NF27 - Chap ⁇ 1 151> - Pharmaceutical Dosage Forms
  • the compositions according to the invention can therefore be in liquid, semi-solid, pasty or solid form and, more particularly, in the form of ointments, oily solutions, optionally biphasic lotion-type dispersions, serum, anhydrous or lipophilic gels, powders, soaked swabs, syndets, wipes, sprays, foams, sticks, shampoos, compresses, washing bases, emulsions of liquid or semi-liquid consistency of the oil type in glycol or glycol in oil, a microemulsion, suspensions or semi-liquid or solid emulsion
  • the anhydrous composition according to the invention is preferably an ointment.
  • Ointment according to the invention means a particular composition as defined in the American or European pharmacopoeia mentioned above.
  • the FDA thus defines the ointment as a semi-solid composition comprising, as a carrier, less than 20% water and volatile compounds and more than 50% hydrocarbons, waxes, or polyol. In some cases, when volatile levels are important such compositions may be called creams (American Food and Drug Administration (FDA) decision tree).
  • FDA American Food and Drug Administration
  • the American Pharmacopoeia defines an ointment as a product whose base is a vehicle that can belong to the following 4 classes: hydrocarbon base or absorbent base or water-washable base or water-soluble base.
  • the ointment as defined in the American Pharmacopoeia is of the hydrocarbon base type.
  • the European Pharmacopoeia defines ointment as a single-phase composition in which liquids or solids can be dispersed.
  • the ointment according to the invention is a thick composition at room temperature, which comprises between 80 and 98% by weight relative to the total weight of the composition of hydrophobic compounds distinct from petroleum jelly.
  • Such compounds are chosen in particular from liquid oils alone or as a mixture, said oils, which may be volatile or nonvolatile hydrocarbons, esters, vegetable oils and / or silicone oils, which may be gelled by solid-phase lipophilic compounds such as waxes, butters, fatty acid esters; .
  • a flow threshold measurement may be performed to characterize the finished product.
  • a HAAKE rheometer of type VT550 with a measurement mobile SVDIN was used.
  • the rheograms are produced at 25 ° C and imposed speed from 0 to 100 s "1.
  • the viscosity values are given to the shear values of 4 s" 1, 20s “1 100s” 1 ( ⁇ ).
  • flow threshold ⁇ 0 expressed in Pascal
  • ⁇ 0 expressed in Pascal is meant the force required (minimum shear stress) to overcome Van der Waals cohesive forces and cause flow.
  • ambient temperature means a temperature between 20 and 30 ° C.
  • the anhydrous nature of the ointment containing no petrolatum or elastomer according to the invention makes it possible to avoid the instability of the phenol derivative, in particular its oxidation in an aqueous medium.
  • the use of sulphite type antioxidants essential for the stabilization of hydroquinone in an aqueous medium is therefore no longer necessary. Therefore, in a preferred embodiment according to the invention, the composition does not contain sulfites and contains an amount of antioxidants strictly less than 0.3% by weight relative to the total weight of the composition, preferably less than 0.2%.
  • antioxidants that can be used according to the invention are preferably antioxidants such as vitamin E and its derivatives, such as DL alpha Tocopherol or Roche tocopherol acetate; vitamin C and its derivatives, such as Roche's Ascorbyl Palmitate, butylhydroxytoluene sold under the name Nipanox BHT by Clariant.
  • vitamin E and its derivatives such as DL alpha Tocopherol or Roche tocopherol acetate
  • vitamin C and its derivatives such as Roche's Ascorbyl Palmitate, butylhydroxytoluene sold under the name Nipanox BHT by Clariant.
  • the anhydrous ointment according to the invention comprises: at least one first solubilized phenolic derivative pharmaceutical active ingredient, at least one first retinoid-type pharmaceutical active ingredient, glyceryl behenate and / or derivatives and / or their mixtures, optionally, at least one additional lipophilic thickener or gelling agent, at least one solvent of the phenolic derivative, optionally at least one solvent or dispersant of the retinoid, and optionally at least one fatty substance or oil.
  • the anhydrous composition according to the invention contains substantially no petrolatum, ie comprises at most 1% by weight of petrolatum relative to the total weight of the composition.
  • rucinol salts is intended especially to mean salts formed with a pharmaceutically acceptable base, in particular a mineral base such as sodium hydroxide, potassium hydroxide and aqueous ammonia, or an organic base such as lysine, arginine, N-methyl- glucamine, but also the salts formed with fatty amines such as dioctylamine, aminomethyl propanol and stearylamine.
  • a pharmaceutically acceptable base such as sodium hydroxide, potassium hydroxide and aqueous ammonia
  • organic base such as lysine, arginine, N-methyl- glucamine, but also the salts formed with fatty amines such as dioctylamine, aminomethyl propanol and stearylamine.
  • hydroquinone or rucinol is used.
  • the amount of pharmaceutical active ingredient of the phenol derivative type is from 0.01 to 10% by weight relative to the total weight of the composition, preferably from 0.05 to 6% by weight and more particularly from 0.1 to 10% by weight. 5% by weight.
  • the composition comprises, as a second pharmaceutical active ingredient, a retinoid.
  • Retinoid means any compound binding to receptors (retinoic acid receptors (RARs) and / or retinoic X receptors (RXRs)) as well as their precursors and derivatives.
  • RARs retinoic acid receptors
  • RXRs retinoic X receptors
  • the retinoids that can be used in the context of the invention include in particular all-trans retinoic acid or tretinoin, 13-cis-retinoic acid or isotretinoin, acitretin, arotinoic acid, retinol, tazarotene, retinaldehyde, etretinate and the compounds protected in patent applications EP 0 199 636, US 4,666,941, US 4,581,380, EP 0 210 929, EP 0 232 199, EP 0 260 162 and EP 0 292 348, EP 0 325 540, EP 0 359 621, EP 0 409 728, EP 0 409 740, EP 0 552 282, EP 0 584 191, EP 0 514 264, EP 0 514 269, EP 0 661 260, EP 0 661 258, EP 0 658 553, EP 0 679 628, EP 0 679 631, EP 0 679
  • adapalene and its salts are preferred, and 3 "-tert-butyl-4 '- (2-hydroxyethoxy) -4" -pyrrolidin-1-yl- [1, 1'; 3 ', 1 "] terphenyl-4-carboxylic acid.
  • Suitable salts of adapalene are in particular salts formed with a pharmaceutically acceptable base, in particular mineral bases such as sodium hydroxide, potassium hydroxide and aqueous ammonia or organic bases such as lysine, arginine, N- methylglucamine, and salts formed with fatty amines such as dioctylamine and stearylamine.
  • retinoid precursors are meant their immediate biological precursors or substrates, as well as their chemical precursors.
  • Derivatives of retinoids include both their metabolic derivatives and their chemical derivatives.
  • the composition comprises an amount of retinoid agent of between 0.0001 and 1% by weight relative to the total weight of the composition, preferably between 0.001 and 0.5%, even more preferably between 0.01 and 0.3%. in weight.
  • the composition according to the invention comprises glyceryl behenate, its derivatives or their mixtures.
  • Derivatives of glyceryl behenate include but are not limited to glyceryl monobhenate, glyceryl dibenenate, tribehenin.
  • the composition according to the invention preferably comprises, in a preferred manner, the mixture of glyceryl dibenenate, tribehenin and glyceryl behenate. Such a mixture is especially marketed under the name Compritol 888 by Gattefossé.
  • glyceryl behenate is understood to mean glyceryl behenate, its derivatives or their mixtures.
  • Glyceryl behenate is an oily phase thickener.
  • the glyceryl behenate is en masse in time and makes it possible to prepare a hydrophobic composition whose final viscosity is obtained only after a certain time.
  • the constituents and the process are indeed chosen so as to impart fluidity to the composition at the end of immediate manufacture, facilitating the homogenization of the various constituents, but a final viscosity sought for about 24 hours following the manufacturing.
  • the composition comprises from 1 to 40%, preferably from 5 to 30%, and even more preferably from 10 to 25% by weight relative to the total weight of the composition of glyceryl behenate.
  • composition according to the invention may also comprise at least one lipophilic gelling agent, or else called additional lipophilic thickener.
  • a gelling agent or additional lipophilic thickener provides a better physical stability to the composition, in particular when the latter is subjected to accelerated conditions of stability (ICH criteria) at around 40 ° C.
  • these compounds are used in the present invention as "viscosity adjusters": in particular, by choosing them judiciously, they ensure the stability of the composition at 40 ° C. This therefore gives a better stability to the compositions obtained.
  • Additional lipophilic thickeners or gelling agents according to the invention are compounds which are distinct from glyceryl behenate, chosen in particular from waxes, fatty alcohols, hydrogenated oils and fatty acid esters.
  • wax is generally meant a lipophilic compound, solid at room temperature (25 ° C.), with a reversible solid / liquid state change, having a melting point of greater than or equal to 30 ° C. and up to at 200 0 C and in particular up to 120 0 C.
  • waxes that can be used mention may be made of carnauba wax, microcrystalline waxes, beeswax, marketed under the name White Cerabeil by Barlocher, or wax of candelilla.
  • Hydrogenated oil is understood to mean the oils obtained by catalytic hydrogenation of animal or vegetable oils having linear or branched C 8 -C 32 fatty chains.
  • hydrogenated jojoba oil isomérz jojoba oil such as trans isomerized partially hydrogenated jojoba oil manufactured or marketed by Desert Whale under the trade reference ISO-JOJOBA-50 ® , hydrogenated sunflower oil, hydrogenated castor oil, marketed in particular under the name Cutina HR by
  • hydrogenated coconut oil and hydrogenated lanolin oil preferably, the hydrogenated castor oil will be used.
  • the composition comprises a total amount of glyceryl behenate and optionally additional lipophilic thickeners or gelling agents of between 1 and 40% by weight relative to the total weight of the composition, preferably between 5 and 35%.
  • the composition comprises from 10 to 25% by weight of glyceryl behenate, and from 0 to 30% by weight of additional lipophilic thickener, preferably from 1 to 10%.
  • composition without elastomer according to the invention is meant an anhydrous composition comprising at most 1% by weight of elastomer relative to the total weight of the composition.
  • the ointment according to the invention does not contain an elastomer.
  • elastomer is understood to mean any polyorganosiloxane elastomer, namely any chemically crosslinked siloxane polymer which has viscoelastic properties. Indeed, the desired viscosity of the composition according to the invention is obtained using, in particular, glyceryl behenate and the choice of other fatty substances used.
  • the absence of elastomer within the composition makes it possible, in particular, to introduce more oily compounds thus conferring on the composition the desired emollient properties.
  • the absence of elastomer makes it possible in particular to obtain the effect of the more marked glycenyl behenate, namely, a fluidity of the composition at the end of manufacture and a final viscosity reached about 24 hours after manufacture.
  • the composition also comprises at least one solvent of the phenolic derivative pharmaceutical active ingredient.
  • solvent of the phenolic derivative is meant in particular solvents of alcoholic or glycolic type.
  • composition according to the invention preferentially contains ethanol.
  • glycolic type solvent include for example propylene glycol, ethylene glycol, 1,3-butylene glycol and dipropylene glycol.
  • the solvents of the phenolic derivative of alcoholic or glycolic type that are preferred according to the invention are in particular ethanol and propylene glycol.
  • the solvent of the phenolic derivative pharmaceutical active ingredient is ethanol.
  • the total amount of solvent is between 1 and 80% by weight, preferably between 5 and 50% and more particularly between 10 and 30% by weight, relative to the total weight of the composition.
  • the composition also comprises at least one solvent or dispersant of the retinoid.
  • the solvent or dispersant of the retinoid may be oily, alcoholic or glycolic type.
  • the alcoholic or glycolic solvents may be of the type described above.
  • the oily solvents or dispersants may be of any type known to those skilled in the art, in particular mineral, vegetable oils, esters or triglycerides.
  • the preferred retinoid is adapalene and is therefore present in dispersed form.
  • the preferred dispersant of the adapalene according to the invention is preferably of oily type, and more particularly of triglycerides such as Caprylic / Caprique Triglycerides sold under the name Miglyol 812 N by IMCD or glycolic type, such as propylene glycol.
  • the total amount of solvent or dispersant of the retinoid is between 1 and 80% by weight, and preferably between 1 and 60% by weight, relative to the total weight of the composition.
  • fatty substances or oil selected from the following list:
  • oils such as sweet almond oil sold by Sictia or sesame oil sold by CPF, silicone oils such as cyclomethicone sold under the name ST-Cyclomethicone 5NF by Dow Corning or Dimethicone sold under the name of Q7 9120 silicon fluid by Dow corning,
  • mineral oils such as Marcol 152 or Primol 352 sold by Esso,
  • triglycerides such as Caprylic / Caprique Triglycerides sold under the name Miglyol 812 N by IMCD, or derivatives such as PEG-8 Caprylic Capric Triglycerides sold under the name Labrasol by the company Gattefossé,
  • esters such as the Octyl Dodecyl Myristate sold under the name MOD by Gattefossé, the C12-C15 alkyl benzoate sold under the name Tegosoft TN by Goldschmit or the cetearyl isononanoate sold under the name Cetiol SN PH by Cognis ,
  • guerbet alcohols such as octyldodecanol sold under the name Eutanol G by Cognis,
  • compositions according to the invention When at least one fatty substance or oil is present in the composition, their amount is between 0.05 and 98% by weight, preferably between 1 and 80% by weight.
  • the composition according to the invention may also comprise at least one surfactant, and / or at least one binder.
  • the surfactants used are preferably nonionic surfactants, used for example, but not exclusively, to facilitate the incorporation of certain constituents such as glycols into the oily phase of the composition.
  • glyceryl and optionally polyethylene glycol esters such as the mixture of glyceryl stearate and PEG-100 stearate, sold under the name Arlacel 165 by Uniqema, the mixture glyceryl stearate and PEG-75 stearate, sold under the name Gelot 64 by Gattefossé, glyceryl stearate sold under the name Cutina GMSV by Cognis; emulsifying waxes, such as the self-emulsifying wax sold under the name of Polawax NF by Croda, or the PEG-8 beeswax sold under the name of Apifil by Gattefossé; polysorbate 80 sold under the name Tween 80 by Uni
  • the composition may also comprise at least one binder.
  • binders that can be used are magnesium stearate sold by Brenntag, corn starch sold by Roquette, talc sold by WCD, cholesterol sold by Croda or silica sold by Degussa.
  • the binders can be used in an amount of between 1 and 30% by weight, preferably between 1 and 20% by weight.
  • composition according to the invention may also contain additives between 0 and 20%, preferably between 0 and 10% by weight relative to the total weight of the composition, additives that the man of the art will choose according to the desired effect.
  • additives for example, taken alone or in combination:
  • vitamins such as vitamin PP or niacinamide
  • soothing and / or anti-irritant agents such as the PPG-12 / SMDI copolymer sold by Bertek pharmaceuticals under the trade name Polyolprepolymer-2 or glycyrrhetinic acid or its derivatives, for example Enoxolone sold by Cognis, or hyaluronic acid,
  • moisturizing or humectant agents for example, sugars and derivatives, glycols, glycerin, sorbitol,
  • preservatives such as paraben methyl sold under the name Nipagin M by Clariant, propyl paraben sold under the name Nipasol by Clariant, or phenoxyethanol sold under the name phenoxetol by Clariant,
  • acids or bases such as citric acid, sodium citrate, triethanolamine, aminomethylpropanol, sodium hydroxide, diisopropanolamine,
  • composition according to the invention comprises, by weight relative to the total weight:
  • composition according to the invention comprises, by weight relative to the total weight:
  • composition according to the invention comprises, by weight relative to the total weight: 0.01 to 5% of hydroquinone or of rucinol,
  • the invention also relates to the use of the composition thus obtained as a medicament.
  • the composition can be used to prepare a medicament for the treatment and prevention of hyperpigmentary disorders such as melasma, chloasma, lentigines, senile lentigo, vitiligo, freckles, post-inflammatory hyperpigmentations.
  • hyperpigmentary disorders such as melasma, chloasma, lentigines, senile lentigo, vitiligo, freckles, post-inflammatory hyperpigmentations.
  • hyperpigmentary disorders such as melasma, chloasma, lentigines, senile lentigo, vitiligo, freckles, post-inflammatory hyperpigmentations.
  • the subject of the invention is also the use of the composition in the cosmetic field.
  • compositions according to the invention also find application in the cosmetics field, in particular in the protection against the harmful aspects of the sun, for preventing and / or for combating photoinduced or chronological aging of the skin and superficial body growths.
  • the invention also relates to a non-therapeutic cosmetic treatment method for beautifying the skin and / or improving its surface appearance, characterized in that a composition comprising adapalene and at least one depigmenting agent is applied to the skin and / or its integuments.
  • the subject of the present invention is also a process for the preparation of the compositions according to the invention.
  • Such a method allows in particular the maintenance of the compounds in the fluid state at the end of manufacture.
  • One of the essential characteristics of the process for preparing the compositions according to the invention is the incorporation of the active phase at ambient temperature, that is to say that the final step of mixing the phases is carried out at room temperature.
  • ambient temperature is meant a temperature of between 20 and 30 ° C.
  • active phase a phase containing at least one active ingredient.
  • non-active phase a phase consisting of any other ingredient different from the active ingredient.
  • the non-active phase is preferably an oily phase containing at least glyceryl behenate, preferably with another oily compound as described above.
  • the process for producing the composition according to the invention is carried out according to Example 1, characterized in that the phases containing the pharmaceutical active ingredients are mixed at room temperature.
  • the mixture of the active and non-active phases at room temperature avoids the volatilization of the solvent (s) and the degradation of the active agents, potentially sensitive to heat, in particular the phenolic derivatives such as hydroquinone or rucinol.
  • the examples of formulations below make it possible to illustrate the compositions according to the invention, without however limiting the scope thereof.
  • the amounts of the constituents are expressed in% by weight relative to the total weight of the composition.
  • phase A Preparation of the fat phase or non-active phase (phase A):
  • phase B Solubilize the retinoid in the appropriate solvent, (phase B)
  • phase B If presence of a retinoid dispersed in the composition, for example adapalene, weigh at this stage, adapalene in an oily liquid, and disperse under high shear (phase B).
  • a retinoid dispersed in the composition for example adapalene
  • the active phase (s) at the base form at room temperature, for the solubilizations in ethanolic or glycolic phase. Incorporate additional phases as needed.
  • the packaging is made at the end of manufacture because the product does not yet have its final viscosity.
  • the physical stability is measured by a macroscopic and microscopic observation of the formulation at ambient temperature, at 4 ° C. and at 40 ° C. after 1 month, 2 months and optionally 3 months and 6 months of storage.
  • the macroscopic observation makes it possible to guarantee the physical integrity of the products and the microscopic observation makes it possible to verify that there is no recrystallization of the solubilized active agent.
  • the chemical stability is measured by assaying the active ingredients by external calibration in HPLC and the results are expressed in% recovery relative to the value obtained at TO or relative to the theoretical title.
  • Macroscopic appearance thick and supple ointment, white
  • Macroscopic appearance Thick and supple ointment, white with light yellow reflections
  • Microscopic aspect Absence of hydroquinone crystals, adapalene dispersion of ⁇ 2.5 ⁇ m at 5 ⁇ m.
  • Macroscopic appearance Thick and supple ointment, white with light yellow reflections
  • Microscopic aspect Absence of hydroquinone crystals, adapalene dispersion of ⁇ 2.5 ⁇ m at 5 ⁇ m. Physical stability:

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  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
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EP09769516A 2008-05-30 2009-06-02 Nouvelles compositions dépigmentantes sous forme d'une composition anhydre sans vaseline et sans élastomère comprenant un dérivé phénolique solubilisé et un rétinoïde Withdrawn EP2293788A2 (fr)

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FR0853567A FR2931661B1 (fr) 2008-05-30 2008-05-30 Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise et un retinoide.
PCT/FR2009/051036 WO2009156675A2 (fr) 2008-05-30 2009-06-02 Nouvelles compositions dépigmentantes sous forme d'une composition anhydre sans vaseline et sans élastomère comprenant un dérivé phénolique solubilisé et un rétinoïde

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AU (1) AU2009264011A1 (ru)
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CN109789066A (zh) * 2016-06-30 2019-05-21 西姆莱斯股份公司 含有间苯二酚衍生物的药物和化妆组合物
US11331254B2 (en) * 2018-09-25 2022-05-17 L'oreal Compositions for providing a protective barrier
US11278479B2 (en) 2018-09-25 2022-03-22 L'oreal Moisturizing anhydrous butter balm composition and method
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AU2009264011A1 (en) 2009-12-30
WO2009156675A2 (fr) 2009-12-30
CN102046161A (zh) 2011-05-04
JP2011521933A (ja) 2011-07-28
FR2931661A1 (fr) 2009-12-04
MX2010012754A (es) 2010-12-21
RU2010154235A (ru) 2012-07-10
KR20110015027A (ko) 2011-02-14
US20110152372A1 (en) 2011-06-23
WO2009156675A3 (fr) 2010-04-08
FR2931661B1 (fr) 2010-07-30

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