Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/075—Ethers or acetals
  • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
• • 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
  • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
  • A61K8/347—Phenols
• • 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
  • 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
  • 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
  • A61P17/16—Emollients or protectives, e.g. against radiation
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• • 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
  • 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
  • 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

Definitions

• Hydroalcoholic depigmenting gel comprising Mequinol and Padapalene
• the invention relates to a depigmenting composition for cosmetic or pharmaceutical application comprising, in a physiologically acceptable medium, mequinol (4-hydoxyanisole), adapalene (6- [3- (1-adamantyl) -4-methoxyphenyl) Naphthhanoic), especially in dispersed form, in the form of a hydroalcoholic gel or cream-gel.
• phenolic derivatives such as mequinol and its derivatives remain for decades among the most effective assets.
• the phenol derivatives are known for their sensitivity to oxidation and heat resulting in rapid browning of the formulations, sometimes up to their phase shift.
• adapalene is very slightly soluble in water, it is necessary to disperse it in the form composition and thus the possible sedimentation of this active product is the major problem encountered when it must be included in a formulation.
• the difficulty lies in obtaining a formulation both sufficiently fluid, having a certain viscosity to keep the product in suspension and not flow, and containing adapalene in suspension.
• the suspension of adapalene is successful thanks to the gel or gel-hydroalcoholic form and the use of carbomer gels and wetting surfactants to overcome sedimentation problems.
• sulphite salts are conventionally used to reduce the problem of browning formulations. However, they can alter the viscosity of the electrolyte sensitive formulations.
• the sulphite salts are known to break the carbomer gels, which results in a drop in the viscosity of the gelling agents and, as a result, sedimentation of the active agents.
• a topical pharmaceutical composition containing mequinol and adapalene whose formulation is physically stable (without phase separation and without a significant drop in viscosity) and chemically (without modifying the stability of the active ingredients. ) and which optimizes the penetration of adapalene and mequinol into the skin.
• the gel or gel-hydroalcoholic cream by its composition and in particular by the presence of 2 to 10% alcohol, guarantees both the stability of the composition and its components and the safety of that -this.
• the stability monitoring of the formulations presented in the examples below shows that the combination of the active compounds with the sulphite salts and in particular sodium metabisulfite and sodium sulphite, EDTA and alcohol (ethanol ) significantly decreases the browning of the mequinol.
• sulphite salts and in particular sodium metabisulfite and sodium sulphite, EDTA and alcohol (ethanol ) significantly decreases the browning of the mequinol.
• EDTA sodium metabisulfite and sodium sulphite
• alcohol ethanol
• the gelling agent (s) chosen, alone or in combination, must have the following properties:
• the stability of the active phase of the compositions according to the invention explains in particular the effectiveness of the product.
• the Applicant has also developed a method of manufacturing the composition according to the invention.
• the invention therefore relates to a depigmenting composition
• a depigmenting composition comprising, in a physiologically acceptable medium, mequinol and adapalene, characterized in that it is a gel or a hydroalcoholic cream gel.
• Physiologically acceptable medium means a medium compatible with the skin, mucous membranes and / or integuments.
• depigmenting composition any composition comprising at least one active agent having a depigmenting activity of the skin. This activity reduces the already existing pigmentation of the skin.
• hydroalcoholic gel is meant an aqueous gel containing alcohol, water and at least one gelling agent.
• hydroalcoholic gel-cream an aqueous gel containing an aqueous phase, a small proportion (from 0 to 20% and preferably 10%) of fatty phase, and alcohol, said aqueous phase containing a gelling agent that can form a network trapping oily droplets and keeping them in suspension.
• the gel-cream hydroalcoholic is a formulation that combines the benefits of a gel (ease of application, quick release of the asset, freshness on application) to those of a cream (comfort of the skin due to the low proportion of fat phase, no dry skin).
• composition according to the invention preferably contains from 2 to 10% of alcohol and preferably 5%.
• alcohols mention may be made, without limitation, of ethanol, isopropanol and butanol. Ethanol is particularly preferred.
• composition according to the invention also comprises a chelating agent, a wetting surfactant and one or more gelling agents.
• the composition according to the invention also contains one or more of the following ingredients: a) a carbomer; b) one or more other gelling agents; c) an antioxidant; d) an oily phase; e) a humectant / emollient agent; f) an anti-irritant agent; g) a pH neutralizing agent; h) a preservative.
• the hydroalcoholic gel or cream-gel according to the present invention comprises a carbomer and one or more other gelling agents or said carbomer and one or more other carbomers; Indeed, as mentioned above, these compounds provide a viscosity suitable for the composition, while maintaining the adapalene in suspension.
• carbomer 1382 sold under the name Carbopol 1382 by the company BF Goodrich or acrylate / C10-C30 alkyl acrylate crosspolymer, sold under the name of Pemulen TR1 by the company BF Goodrich, xanthan gum such as Keltrol T sold by Kelco, carbopol 980, carbopol 981, carbopol Ultrez 10, carbopol EDT 2020, carbopol 974, hydroxypropylcellulose such as that the product sold under the name of Natrosol HHX 250 by the company Aqualon, and Acrylamide / Sodium Acryloyldimethyltaurate Copolymer and Isohexadecane and polysorbate 80 sold under the name Simulgel 600 by the company Seppic.
• carbomer 1382 sold under the name Carbopol 1382 by the company BF Goodrich or acrylate / C10-C30 alkyl acrylate crosspolymer, sold under the name of Pemulen TR1 by the company BF
• gelling agents mention may preferably be made of the combination of carbomer / acrylate / C10-C30 alkyl acrylate crosspolymer with xanthan gum and hydroxyethyl cellulose or the carbomer 1382 combination with xanthan gum and carbomer 981.
• antioxidants mention may be made, by way of non-limiting examples, of ascorbic acid and its salts, tocopherols and sulphite salts, such as sodium metabisulphite and sodium sulphite.
• the oily phase of the composition according to the invention may comprise, for example, vegetable, mineral, animal or synthetic oils, silicone oils, and mixtures thereof.
• paraffin oils of different viscosities such as Primol 352, Marcol 82, Marcol 152 sold by Esso.
• sweet almond oil there may be mentioned sweet almond oil, palm oil, soybean oil, sesame oil, sunflower oil.
• animal oil there may be mentioned lanolin, squalene, fish oil, mink oil.
• esters such as cetearyl isononanoate, such as the product sold under the name Cetiol SN by Cognis France, diisopropyl adipate, such as the product sold under the name Ceraphyl 230 by the company ISF, palmitate.
• isopropyl as the product sold under the name Crodamol IPP by the company Croda
• caprylic capric triglyceride such as Miglyol 812 sold by the company HuIs / Lambert River.
• silicone oil mention may be made of a dimethicone such as the product sold under the name of Dow Corning 200 fluid, a cyclomethicone such as the product sold under the name Dow Corning 244 fluid by Dow Corning or the product sold under the name Mirasil CM5 by SACI-CFPA.
• solid fatty substances such as natural or synthetic waxes.
• those skilled in the art will adapt the heating temperature of the preparation depending on the presence or absence of these solids.
• paraffin oils and more particularly Marcol 152 are preferred.
• the composition according to the invention advantageously comprises one or more wetting surfactants in concentrations of 0.01 to 10% and preferably of 0.1 to 5%.
• they are surfactants having a HLB (Hydrophilic Lipophilic Balance) of 7 to 9, or else nonionic surfactants of the polyoxyethylenated and / or polyoxypropylenated copolymer type.
• the compounds of the Poloxamers family and more particularly Poloxamer 124 and Poloxamer 182.
• the most preferred wetting surfactant is Poloxamer 124.
• chelating agents include ethylenediamine tetraacetic acid (EDTA), calcium disodium edetate, sodium edetate, disodium edetate and preferentially disodium edetate and EDTA.
• the composition may furthermore comprise additives conventionally used in the cosmetic or pharmaceutical field, such as a neutralizing agent, a humectant and / or co-solvent, an emollient, a soothing agent, a preservative, a pH-correcting agent. or their mixtures.
• additives may be present in the composition in a proportion of 0.001 to 20% by weight relative to the total weight of the composition.
• humectants / emollients examples include glycerin, sorbitol, propylene glycol.
• Anti-irritants and / or “soothing” agents may also be added in the formulations, such as strontium nitrate, shea butter, the potassium salt of 18 beta-glycyrrhetinic acid, dipotassium glycyrrhizate acid, tea tree oil, enoxolone, alpha-tocopherol acetate, allantoin, talc.
• Examples of a pH-neutralizing agent to obtain an adequate pH are an amino base such as triethanolamine, diethanolamine, tromethamine, tromethamol or other bases such as sodium hydroxide.
• Examples of preservatives include benzalkonium chloride, phenoxyethanol, benzyl alcohol, diazolidinyl urea, parabens, or mixtures thereof.
• composition according to the invention advantageously contains no preservative.
• the active agents according to the invention are mequinol (4-hydroxyanisol) and its precursors and / or derivatives and adapalene (6- [3- (1-adamantyl) -4-methoxyphenyl] -2-naphthhanoic acid. ) in particular in dispersed form, and its precursors and / or derivatives to which it is possible to add other agents as explained above.
• dispersed form is meant the distribution of a solid of variable particle size in a liquid medium.
• the amount of active agents in the composition according to the invention will depend on the combination chosen and therefore particularly the quality of the desired treatment.
• the amount of adapalene is between 0.0001 and 20%, preferably between 0.001 and 10%.
• composition of the gel or gel-hydroalcoholic cream type according to the invention offers good skin tolerance. Its spread is advantageously easier than a viscous emulsion and leaves a pleasant feeling of freshness.
• the invention is a depigmenting hydroalcoholic gel or cream-gel comprising one or more of the following ingredients: from 0.01 to 5% of mequinol;
• a preferred composition according to the invention comprises: - 2% mequinol; - 0.10 to 2% of adapalene;
• a particularly preferred composition according to the invention comprises: 2% mequinol; 0.10% of adapalene;
• the present invention also relates to a composition defined as above and containing a chemical or physical sunscreen.
• sunscreens is meant a chemical or physical sunscreen and their mixtures, non-limiting examples that may be mentioned are physical sunscreens such as titanium dioxide, zinc oxide and chemical sunscreens such as octocrylene, ethylhexyl methoxycinnamate, octyl salicylate, avobenzone, oxybenzone, ecamsule, drometrizole trisiloxane.
• Each sunscreen may be added at a concentration ranging from 0.001% to 20% by weight relative to the total weight of the composition and preferably from 0.001% to 5%.
• the present invention also relates to the composition as described above as a medicament.
• the subject of the invention is also a process for the preparation of a hydroalcoholic gel or gel-cream composition comprising in succession the following steps: a) preparing a form phase with water and stirring Rayneri, then pouring the chelant and stir until dissolved; b) heating the mixture of step a) at 60 ° C.
• the check of the native pH of the mixture is made and its possible correction is carried out with a solution of a neutralizing agent.
• the incorporation of the optional additives may be done according to their chemical nature during one of the steps of the preparation process described above.
• a humectant and / or an anti-irritant may optionally be added in step a) at the same time as the chelant.
• a fatty phase obtained by mixing an oil, a surfactant and a preservative heated in a water bath at 60 ° C. is introduced into the form phase obtained at the end of step b).
• Form phase refers to the mixing of a group of ingredients introduced together in a single phase.
• active phase is meant a form phase containing one or more assets.
• the invention also relates to the use of the novel composition as described above in cosmetics and dermatology.
• the invention relates to the use of a composition as described above for the manufacture of a pharmaceutical preparation intended for the treatment and / or prevention of dermatological disorders related to disorders of pigmentation.
• compositions of the invention are particularly suitable for the treatment and / or prevention of dermatological disorders related to disorders of pigmentation such as melasma, chloasma, lentigines, senile lentigo, vitiligo, freckles, post-inflammatory hyperpigmentations due to abrasion, burning, scarring, dermatitis, contact allergy, nevi, hyperpigmentations with genetic determinism, hyperpigmentations of metabolic or medicinal origin, melanomas or any other hyperpigmentary lesions.
• disorders of pigmentation such as melasma, chloasma, lentigines, senile lentigo, vitiligo, freckles, post-inflammatory hyperpigmentations due to abrasion, burning, scarring, dermatitis, contact allergy, nevi, hyperpigmentations with genetic determinism, hyperpigmentations of metabolic or medicinal origin, melanomas or any other hyperpigmentary lesions.
• compositions according to the invention also find application in the cosmetic field, in particular for preventing and / or for combating the effects harmful to the sun and / or against photo-induced or chronological aging of the skin and integuments.
• compositions according to the invention also find application in body and hair hygiene.
• the invention also relates to a non-therapeutic cosmetic treatment method for embellishing the skin and / or improving its surface appearance, characterized in that a gel is applied to the skin and / or its integuments. or a hydroalcoholic gel-cream according to the invention comprising mequinol and adapalene, and optionally a sunscreen.
• the gel formulation is prepared according to the following method:
• the physical stability of the gel formulation according to Example 1 is measured for 3 months at room temperature (RT), at 4 0 C to 40 0 C and 55 0 C:
• the correct indication means that the characteristics of the composition measured at 1, 2 or 3 months are consistent with those obtained at TO.
• the chemical stability of the gel formulation according to Example 1 is measured by HPLC over 3 months at RT and at 40 ° C.
• the gel-cream formulation is prepared according to the following method:
• aqueous form phase In the receiving beaker introduce the majority water and place under agitation
• auxiliary beaker weigh the mineral oil, the surfactant and the preservative. Heat in a water bath at 60 ° C. Then incorporate in the aqueous phase a) with sufficient Rayneri stirring. Allow the emulsion to come to room temperature.
• the chemical stability of the gel-cream formulation according to Example 3 is measured by HPLC for 3 months at ambient temperature (RT) and at 40 ° C.
• flow threshold (tau ⁇ ) is meant the force required (minimum shear stress) to overcome Van der Waals cohesive forces and cause flow.
• the flow threshold is equivalent to the value found at 4 s-1.
• Example 5 Other gel-cream formulation
• Example 6 Physical and Chemical Stability of the Gel-Cream Formulation According to Example 5
• the chemical stability of the gel-cream formulation according to Example 5 is measured by HPLC for 2 months at ambient temperature (RT) and at 40 ° C.
• Example 7 Other formulation qel-cream
• the chemical stability of the gel-cream formulation according to Example 7 is measured by HPLC for 1 month at ambient temperature (RT) and at 40 ° C.
• This composition is physically and chemically stable at all temperatures.
• Carbomer (Carbopol 981 NF) 0.20
• Example 10 Stability of the gel-cream formulation according to Example 9
• the physical stability of the gel-cream formulation according to Example 9 is measured for 3 months at room temperature (RT), at 45 ° C. and at 55 ° C.
• This composition is physically stable (pH, viscosity) at all temperatures for 3 months.
• the gel-cream formulation is prepared according to the method described in Example 3.
• the sunscreens are introduced during step b).
• EXAMPLE 12 Measurement of the Depigmenting Activity of the Adapalene and Mequinol Combination in the SKH2 Mouse
• the purpose of the present study is to evaluate the depigmenting activity of a composition comprising either (i) 2% mequinol, (ii) 0.1% adapalene or (iii) the combination of the two (composition according to the invention) on the skin of the SKH2 mouse tail after 4 weeks of topical application. Both gel and gel-cream formulations are also compared.
• the topical application of the two formulations (20 .mu.l) is carried out on the tail of the SKH2 mice divided into two groups (female mice and approximately 9 weeks old) at the rate of one application per day for 5 days during 4 weeks.
• the assessment is made by different clinical observations: once a week, the pigmentation is evaluated with a score on a scale of 0 to 4.
• the distribution of the scores is as follows: 0: natural pigmentation
• FIG. 1 represents the kinetics of skin depigmentation scores of mice as a function of the treatment time for the two formulations with:
• FIG. 2 represents the comparative depigmentation scores of the two formulations with:
• 2% mequinol has a significant depigmenting effect, which is increased when 0.1% of adapalene is applied in combination.
• Adapalene alone at 0.1% has no depigmenting effect since the graph gives a score equal to 0 for the gel formulation and the gel-cream formulation. The same equal score is 0 is also recorded for controls (untreated mice and placebo-treated mice).
• the depigmenting effect is faster and more intense with the gel-cream formulation and in particular in the case of the combination of Mequinol with Adapalene.
• formulations according to the examples of 1, 3, 5, 7 and 9 can be applied 1 or 2 times per day until total depigmentation for the treatment of lentigines, chloasma or melasma.

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