EP2125118A2 - Gel creme comprenant au moins un retinoide et du péroxyde de benzoyle - Google Patents

Gel creme comprenant au moins un retinoide et du péroxyde de benzoyle

Info

Publication number
EP2125118A2
EP2125118A2 EP07872022A EP07872022A EP2125118A2 EP 2125118 A2 EP2125118 A2 EP 2125118A2 EP 07872022 A EP07872022 A EP 07872022A EP 07872022 A EP07872022 A EP 07872022A EP 2125118 A2 EP2125118 A2 EP 2125118A2
Authority
EP
European Patent Office
Prior art keywords
composition according
benzoyl peroxide
agents
phase
retinoid
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Withdrawn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
EP07872022A
Other languages
German (de)
English (en)
French (fr)
Inventor
Claire Mallard
Fabienne Louis
Emmanuelle At
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
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38268854&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP2125118(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Galderma Research and Development SNC filed Critical Galderma Research and Development SNC
Priority to EP12153666.8A priority Critical patent/EP2460562B1/fr
Priority to EP15194565.6A priority patent/EP3025763B1/fr
Publication of EP2125118A2 publication Critical patent/EP2125118A2/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Withdrawn legal-status Critical Current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
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/327—Peroxy compounds, e.g. hydroperoxides, peroxides, peroxyacids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • 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
    • A61K8/38—Percompounds, e.g. peracids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
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    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
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    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
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    • A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61Q19/008—Preparations for oily 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/008—Preparations for oily hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
    • 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

  • the invention relates to a gel-cream composition
  • a gel-cream composition comprising, in a physiologically acceptable medium, at least one retinoid and dispersed benzoyl peroxide.
  • benzoyl peroxide is related to its decomposition when it is brought into contact with the skin. Indeed, it is the oxidizing properties of the free radicals produced during this decomposition that lead to the desired effect. Also, in order to maintain benzoyl peroxide optimal efficiency, it is important to prevent its decomposition before use, ie during storage. But benzoyl peroxide is an unstable chemical compound that makes it difficult to formulate in finished products.
  • the degradation times of benzoyl peroxide in PEG 400 are respectively 1, 4, 29 and 53 days at 40 ° C. Such degradation does not allow the preparation of a product for sale.
  • benzoyl peroxide is more stable in water and propylene glycol when it is in suspension (ie in dispersed form), since it is not degraded after 90 days of storage in these solvents. .
  • this type of formulation is not completely satisfactory insofar as there is always a deterioration of benzoyl peroxide in the finished product.
  • a stability study of two retinoids was carried out by combining two commercial products, one containing a retinoid (tretinoin or adapalene) and the second containing benzoyl peroxide (B. Martin et al., Br.J.Dermatol. (1998) 139, (suppl.52), 8-11).
  • the presence of the formulation based on benzoyl peroxide causes a very rapid degradation of retinoids sensitive to oxidation: it is measured that 50% of tretinoin degrades in 2 hours, and 95% in 24 hours. In the composition in which the retinoid is adapalene, no degradation of adapalene was measured for 24 hours.
  • This study confirms that benzoyl peroxide degrades and degrades oxidation-sensitive retinoids over time by progressively releasing benzoic acid into finished products.
  • the cream gel formulation of benzoyl peroxide and a retinoid can be advantageous for topical treatments, such as acne, because while providing the emollient, it avoids including leaving a touch too greasy on the skin. skin.
  • Such a composition is a cream gel which comprises: dispersed benzoyl peroxide, in particular in free or encapsulated form, at least one retinoid, at least one lipophilic compound constituting the fatty phase, and at least one pH-independent gelling agent having good physical stability, i.e. having no drop in viscosity over time and at temperatures between 4 and 40 ° C, and maintaining good chemical stability of the two active agents (benzoyl peroxide and retinoid), that is to say that no degradation of the active agents is observed over time and at temperatures between 4 and 40 °.
  • compositions of the present invention may be in any of the galenical forms normally used for topical application, and especially in the form of cream-like cream of semi-liquid consistency of the cream-type solid-consistency milk type, obtained by dispersion of a fatty phase. in an aqueous phase (O / W).
  • a fatty phase obtained by dispersion of a fatty phase. in an aqueous phase (O / W).
  • composition according to the invention may in particular comprise, in addition to at least one retinoid, benzoyl peroxide, a fatty phase and at least one pH-independent gelling agent, one or more of the following ingredients: a) one or more wetting agents, b) a or several chelating agents, c) an aqueous phase, d) one or more additives.
  • the Applicant has also surprisingly discovered that a perfect dispersion of the active ingredients could be obtained by following a particular preparation process.
  • This preparation process makes it possible to obtain an optimum particle size distribution and a homogeneous dispersion of the two active ingredients in the composition, while guaranteeing the physical stability of the product.
  • the invention thus relates to a composition in the form of a gel-cream comprising, in a physiologically acceptable medium, at least one retinoid and dispersed benzoyl peroxide.
  • composition according to the invention is preferably in the form of an aqueous cream gel.
  • the gel-cream is characterized by the presence of aqueous phase gelling agents and a fatty phase.
  • emulsifier s which differentiates gel-creams from emulsions.
  • Emulsifiers are amphiphilic compounds which have a hydrophobic part having an affinity for the oil and a hydrophilic part having an affinity for water thus creating a link between the two phases. Ionic or nonionic emulsifiers thus stabilize O / W emulsions by adsorbing at the interface and forming lamellar layers of liquid crystals.
  • composition according to the invention is physically and chemically stable.
  • physiologically acceptable medium a medium compatible with topical application to the skin, superficial body growths and / or mucous membranes.
  • composition according to the invention contains at least one retinoid.
  • Retinoid means any compound binding to the RAR and / or RXR receptors.
  • retinoid, retinoic acid, tretinoin, tazarotene and those described in the following patents or patent applications may be cited as examples: US 4,666,941, US 4,581,380, EP 0 210 929 and EP 0 232. 199, EP 0 260 162, 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.
  • EP 0 934 295 EP 0 915 823, EP 0 882 033, EP 0 850 909, EP 0 879 814, EP 0 952 974, EP 0 905 18, EP 0 947 496, WO98 / 56783, WO 99/10322. , WO99 / 50239, WO99 / 65872.
  • the compounds derived from the family of benzonaphthalene retinoids as described in the patent application EP 0 199 636 are also included in the invention.
  • the naphthoic acid derivatives will be chosen, and in particular: 6- (3-methylphenyl) -2-naphthoic acid and its methyl ester, 6- (4-tert-butylphenyl) -2-naphthoic acid and its ester methyl, 6- (3-tert-butylphenyl) -2-naphthoic acid and its methyl ester, 6- (3,4-dimethoxyphenyl) -2-naphthoic acid and its methyl ester, 6- (p- (1-adamantylthio) phenyl) -2-naphthoic acid and its methyl ester,
  • adapalene and its salts will be preferred.
  • salts of adapalene means 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-methyl - glucamine.
  • salts of adapalene salts formed with fatty amines such as dioctylamine and stearylamine.
  • fatty amines such as dioctylamine and stearylamine.
  • the amount of the two active agents, benzoyl peroxide and retinoid, in the composition according to the invention will depend on the chosen combination and therefore particularly the retinoid considered and the quality of the desired treatment.
  • the preferred retinoid concentrations are between 0.0001 and 20% by weight relative to the total weight of the composition.
  • the composition according to the invention comprises between 0.001 and 5% and advantageously between 0.01 and 1% by weight of adapalene relative to the total weight of the composition, preferably between 0.01 and 0.5. %, preferably between 0.1 and 0.4% by weight of adapalene, more preferably 0.3% by weight of adapalene.
  • Benzoyl peroxide may also be used in the free form or in encapsulated form, for example in adsorbed form, or absorbed in any porous support. It may be, for example, benzoyl peroxide encapsulated in a polymeric system consisting of porous microspheres, for example micro-sponges sold under the name Microsponges P009A Benzoyl peroxide by the company Amcol.
  • the composition according to the invention advantageously comprises between 0.0001 and 20% by weight of benzoyl peroxide and between 0.0001 and 20% by weight of retinoid relative to the total weight of the composition, and preferably, respectively, between 0.025 and 10% by weight of benzoyl peroxide and between 0.001 and 10% by weight of retinoid relative to the total weight of the composition.
  • benzoyl peroxide is preferably used at concentrations ranging from 2 to 10% by weight and more preferably from 2.5 to 5% by weight relative to total weight of the composition.
  • the retinoid is used in this type of composition at concentrations generally ranging from 0.01 to 1% by weight relative to the total weight of the composition.
  • the particle size of the retinoid and of benzoyl peroxide is such that at least 80% by number of the particles, and preferably at least 90% by number of the particles, have a diameter of less than 25 ⁇ m and at least 99% in number of particles have a diameter less than 100 microns.
  • the cream gel according to the invention comprises one or more gelling agents and / or suspending agents and / or independent pH gelling agents.
  • independent pH gelling agent is meant a gelling agent capable of conferring a sufficient viscosity on the composition to maintain the retinoid and the benzoyl peroxide in suspension, even under the influence of a pH variation due to the release of benzoic acid by the benzoyl peroxide.
  • gelling agents and / or suspending agents and / or pH-independent gelling agents that can be used in the compositions according to the invention
  • Acrylates / C10-30 Alkyl Acrylate Crosspolymer sold under the name of Pemulen TR-1 or Pemulen TR-2 by the company Noveon
  • the so-called non-electrolyte sensitive carbomers sold under the name, of Ultrez 20®, Carbopol 1382 or Carbopol ETD2020NF® sold by the company Noveon
  • the polysaccharides with, by way of nonlimiting examples, xanthan gum such as Xantural180® sold by Kelco, guar gum, chitosans and carrageenans, in particular divided into four major families: K, ⁇ , ⁇ , ⁇ such that Viscarin® and Gelcarin® marketed by IMCD, cellulose and its derivatives such as hydroxypropyl methylcellulose, in particular the product sold under the name Methocel E
  • the preferred gelling agents are derived from the family of polyacrylamides such as Simulgel 600PHA or Sepigel 305; so-called non-electrolyte sensitive carbomers such as Carbopol ETD2020 NF; polysaccharides such as xanthan gum; cellulose derivatives such as hydroxypropylmethylcellulose or hydroxyethylcellulose; silicate magnesium aluminum alone or as a mixture.
  • the gelling agent or suspending agent as described above may be used at preferential concentrations ranging from 0.001 to 15% and, more preferably, from 0.1 to 5%.
  • chelating agents that may be mentioned as non-limiting examples are ethylene diamine tetraacetic acid (EDTA), diethylene triamine pentaacetic acid (DTPA) and ethylene diamine di (O-hydroxyphenyl acetic acid) (EDDHA). ), hydroxy-2-ethylene diamine triacetic acid (HEDTA), ethyldiamine-di (O-hydroxy-p-methyl phenyl) acetic acid (EDDHMA) and ethylene diamine-di (5-carboxy-2) acid -hydroxyphenyl) acetic acid (EDDCHA).
  • EDTA ethylene diamine tetraacetic acid
  • DTPA diethylene triamine pentaacetic acid
  • EDDHA ethylene diamine di (O-hydroxyphenyl acetic acid)
  • HEDTA hydroxy-2-ethylene diamine triacetic acid
  • EDDHMA ethyldiamine-di (O-hydroxy-p-methyl phenyl) acetic acid
  • EDTA ethylene diamine tetraacetic acid
  • concentrations of chelating agent may range from 0% to 1.5%, preferably from 0.05% to 0.5% by weight relative to the total weight of the composition.
  • compositions of the invention may comprise one or more wetting agents. at concentrations of 0 to 20%, preferably 0 to 10% by weight relative to the total weight of the composition.
  • these ingredients are at concentrations ranging from 0.001 to 20%, preferably from 0.1% to 10%, preferably from 0.1% to 7% of wetting agent (s). ) and more preferably still ranging from 2 to 7% by weight relative to the total weight of the composition.
  • They must be non-solubilizing actives at the percentage used, do not cause harmful exothermic reactions for benzoyl peroxide, help the good dispersion of the assets and have anti-foaming properties.
  • Wetting power is the tendency of a liquid to spread over a surface.
  • they are wetting agents that may have an HLB (Hydrophilic)
  • Lipophilic Balance from 7 to 16.
  • Poloxamers and more particularly Synperonic PE / L44 and / or Synperonic PE / L62 sold by Uniqema glycols such as propylene glycol, dipropylene glycol, propylene glycol dipelargonate, lauroglycol, ethoxydiglycol, sorbitan esters such as POE (20) sorbitan monooleate, sold under the name Tween 80 by Uniqema and POE (20) sorbitan monostearate sold under the name " Tween 60 "by Uniqema
  • fatty alcohol ethers such as Ceteareth-20 sold under the name Eumulgin B2 by Cognis
  • glycerol esters such as glycerol monostearate sold under the name" Cutina " GMS "by Cognis
  • Polyoxyethylene (21) stearyl ether sold under the name Brij 721 by Uniqema Polyoxyethylene (21) stearyl ether
  • wetting agents use is preferably made of wetting agents that may preferentially present an HLB of 10 to 14, without this list being limiting, compounds of the Poloxamers family and more particularly Synperonic PE / L44 and / or Synperonic PE / L62 or glycols such as propylene glycol, dipropylene glycol, propylene glycol dipelargonate, lauroglycol, ethoxydiglycol.
  • Particularly preferred wetting agents are propylene glycol or Synperonic PE / L44 (Polyethylene-polypropylene glycol; Polyoxyethylene-Polyoxypropylene Block Copolymer).
  • the gel-cream comprising benzoyl peroxide and a retinoid comprises at least water, at least one gelling agent and / or suspending agent and / or pH-independent gelling agents and may also include one or more wetting agents.
  • composition according to the invention also comprises a fatty phase.
  • This fatty phase may comprise lipophilic compounds alone or as a mixture, for example vegetable, mineral, animal or synthetic oils, silicone oils, and mixtures thereof.
  • mineral oil there may be mentioned, for example, paraffin oils of different viscosities such as Primol 352®, Marcol 82®, Marcol 152® sold by the company Esso.
  • sweet almond oil there may be mentioned sweet almond oil, palm oil, soybean oil, sesame oil, sunflower oil.
  • animal oil mention may be made of lanolin, squalene, fish oil, mink oil with the derivative squalane sold under the name Cosbiol® by Laserson.
  • an ester such as cetearyl isononanoate, such as the product sold under the name Cetiol SN PH® by Cognis France, and isopropyl palmitate, as the product sold under the name Crodamol IPP® by the company Croda company, diisopropyl adipate sold under the name Crodamol DA by the company Croda, caprylic / capric triglyceride such as Miglyol 812® sold by the company HuIs / Univar.
  • dimethicones such as the products sold under the name Q7-9120 silicone fluid with a viscosity of between 20 ° C. and 125 ° C., or the product sold under the name ST-Cyclomethicone 5NF® by the Dow Corning company.
  • 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.
  • composition according to the invention synthetic oils and silicone oils and more particularly Marcol 152® and ST-Cyclomethicone NF® are preferred.
  • the aqueous phase of the cream gel according to the invention may comprise water.
  • This water may in particular be a floral water such as cornflower water, or a natural thermal or mineral water, for example chosen from Vittel water, the waters of the Vichy basin, Uriage water, Roche Posay water, Avène water or Aix les Bains water.
  • Said aqueous phase may be present in a content of between 10 and 90% by weight relative to the total weight of the composition, preferably between 20 and 80% by weight.
  • the composition may furthermore comprise any additive usually used in the cosmetic or pharmaceutical field, such as a benzoyl peroxide stabilizer (for example sodium docusate, C14-16 sodium olefin sulphonate), base neutralizing agents or common mineral or organic acids (for example, the triethanolamine, 10% sodium hydroxide solution, citric acid / sodium citrate buffer, succinic acid / sodium succinate buffer), antioxidants, sunscreens, preservatives, fillers, electrolytes, humectants and / or emollients , dyes, perfumes, essential oils, cosmetic active ingredients, moisturizers, vitamins, essential fatty acids, sphingolipids, self-tanning compounds such as DHA, soothing and protective agents for the skin such as allantoin .
  • a benzoyl peroxide stabilizer for example sodium docusate, C14-16 sodium olefin sulphonate
  • base neutralizing agents or common mineral or organic acids for example, the triethanolamine, 10% sodium hydroxide
  • 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.
  • preservatives examples include benzalkonium chloride, bronopol, chlorhexidine, chlorocresol and its derivatives, ethyl alcohol, phenethyl alcohol, phenoxyethanol, potassium sorbate, diazolidinylurea, chloride and the like.
  • humectants and / or emollients examples include glycerine, sorbitol, sugars (for example glucose, lactose), PEGs (for example Lutrol E400), urea, amino acids (for example serine, citrulline, alanine).
  • the invention also relates to a pharmaceutical or cosmetic composition in gel-cream form comprising, in a physiologically acceptable medium and compatible with the topical application to the skin, the integuments or the mucous membranes, the ingredients (expressed as a percentage by weight ) selected from:
  • a retinoid from 0.001 to 5%, preferably from 0.01% to 0.5% of a retinoid and preferably a derivative of naphthoic acid;
  • preserving agents from 0% to 3%, preferably from 0.05% to 1% of preserving agents; from 0% to 20%, preferably 2% to 15% of humectants and / or emollients;
  • the present invention also relates to the composition as described above as a medicament.
  • the invention also relates to the use of the novel composition as described above in cosmetics and dermatology.
  • compositions of the invention are particularly suitable in the following therapeutic areas:
  • a keratinization disorder with an inflammatory and / or immunoallergic component and in particular all forms of psoriasis whether cutaneous, mucous or ungual, and even psoriatic arthritis, or atopic skin, such as eczema or respiratory atopy or gingival hypertrophy;
  • the compounds can also be used in certain inflammatory conditions not having a keratinization disorder such as folliculitis, 4) to treat all dermal or epidermal proliferations whether benign or malignant, whether or not of origin viral such as warts vulgar, flat warts, molluscum contagiosum, and verruciform epidermodysplasia, oral or florid papillomatosis and proliferations that can be induced by ultraviolet rays, particularly in the case of actinic keratoses,
  • compositions according to the invention are particularly suitable for the treatment, in a preventive or curative manner, of acne vulgaris.
  • An object of the invention also relates to the preparation of a pharmaceutical composition intended for the prevention and / or treatment of dermatological affections linked to disorders of differentiation and / or cell proliferation and / or keratinization, preferably acne vulgaris.
  • compositions according to the invention also find application in body and hair hygiene.
  • the present invention thus also relates to the cosmetic use of a composition according to the invention for the treatment of acne-prone skin, to regrow the hair or to prevent it from falling, to combat the oily appearance of the skin or hair, in protection against the harmful aspects of the sun, or to prevent and / or fight against photo-induced or chronological aging.
  • compositions according to the invention are administered topically.
  • the invention also relates to a method for preparing a composition as described above.
  • a method for preparing a composition as described above is characterized in that it comprises a step of mixing a physiologically acceptable medium with at least one derivative of naphthoic acid and at least benzoyl peroxide.
  • composition according to the invention is thus carried out according to the following main process:
  • a gelling agent neutralizing agent is introduced into the gel-cream obtained in h) or i);
  • composition according to the invention is thus carried out according to the following alternative method:
  • Steps a) and b) are grouped so as to obtain step a') which corresponds to the mixture of at least one retinoid, benzoyl peroxide with water and at least one wetting agent, until 'in perfect dispersion, in order to obtain the unique active phase;
  • Steps c), d), f), g), h), i), j) of the main process remain unchanged. Step e) is deleted.
  • composition according to the invention is carried out by way of example according to the following main process:
  • retinoid and preferably the naphthoic acid derivative are mixed with at least one wetting agent in water until said naphthoic acid derivative is perfectly dispersed in order to obtain the active phase 1;
  • Benzoyl peroxide is mixed with at least one wetting agent in water until it is perfectly dispersed to obtain the active phase 2; c) One or more gelling agents and / or suspending agent and / or pH-independent gelling agent (with the exception of polyacrylamide) and optionally one or more agents are dissolved in water, with stirring, if necessary when hot; chelating agents, one or more preservatives, one or more humectants and / or emollients, one or more stabilizing agents and non-heat-sensitive hydrophilic additives. Stirring and optional heating is maintained until homogeneous to obtain the aqueous phase;
  • At least oils, and possibly solid fats, and preservatives and non-heat-sensitive lipophilic additives are mixed, if necessary hot, to homogeneity in order to obtain the fatty phase;
  • the active phases 1 and 2 are mixed so as to obtain a single active phase
  • the polyacrylamide is introduced to the phase obtained in f);
  • the heat-sensitive additives are added;
  • a gelling agent neutralizing agent is introduced into the cream gel obtained in f) in order to obtain the desired pH
  • composition according to the invention is thus carried out according to the following alternative method:
  • Steps a) and b) are grouped so as to obtain step a') which corresponds to the mixture of at least one retinoid, benzoyl peroxide with water and at least one wetting agent, until 'in perfect dispersion, in order to obtain the unique active phase; Steps c), d), f), g), h), i), j), k) of the main process remain unchanged. Step e) is deleted.
  • the main process for preparing the composition according to the invention comprises the following steps:
  • Step a Preparation of the active phase 1:
  • the active ingredient (adapalene) is weighed, part of the purified water, the wetting agent (s) (propylene glycol type, Synperonic PE / L62, Synperonic PE / L44). They are dispersed with stirring until perfectly dispersed.
  • Step b Preparation of the active phase 2:
  • the active ingredient (benzoyl peroxide)
  • the wetting agents (propylene glycol type, Synperonic PE / L62, Synperonic PE / L44) are weighed. They are dispersed with stirring until perfectly dispersed.
  • Step c Preparation of the aqueous phase
  • the gelling agent (s) Carbopol type, Pemulen TR1, Xantural, Methocel
  • / or suspending agents type Avicel CL-61 1
  • s Carbopol type, Pemulen TR1, Xantural, Methocel
  • suspending agents type Avicel CL-61 1
  • / or pH-independent gelling agents with the exception of Simulgel 600PHA
  • one or more chelating agents EDTA type
  • one or more humectants and / or emollients glycerin type
  • one or more stabilizing agents (docusate type). sodium)
  • preservatives methyl paraben type
  • non-heat-sensitive hydrophilic additives are maintained until perfect homogeneity;
  • Step d Preparation of the fatty phase (optional):
  • the oily compounds isostearic olepal type, Cetiol SN, Crodamol DA, Speziol C18, Miglyol 812, Cosbiol
  • the optional lipophilic additives not heat-sensitive if heating and optionally preservatives (phenoxyethanol type, propyl paraben).
  • the mixture is heated until homogenization and the volatile silicone is introduced if the latter is present in the composition;
  • Step e Mixing of the active phases At a temperature below 40 ° C, the two active phases obtained respectively in a) and b) are mixed, stirring is maintained until perfect homogenization;
  • Step f Introduction of the single active phase into the aqueous phase
  • the single active phase obtained in step e) is introduced into the aqueous phase obtained in step c);
  • Step g (optional): Simulqel 600PHA Addition
  • Simulqel 600PHA is introduced with stirring into the phase obtained in f). Maintain agitation until perfectly dispersed;
  • Step h Addition of the oil or fat phase obtained in d)
  • the unigue constituting fat phase or optionally the fatty phase obtained in step d) is introduced into the mixture obtained in f) or g);
  • Step i (optional): Adding heat-sensitive additives
  • any additives are introduced with stirring.
  • Step j (optional): Neutralization:
  • the gelling agent neutralizing agent triethanolamine type, 10% sodium hydroxide solution, citric acid / sodium citrate buffer, succinic acid / sodium succinate buffer
  • pH buffer is introduced. if necessary, up to the desired pH.
  • the product then takes on a thicker consistency. If necessary, the adjustment to 100% water is performed.
  • the product is homogenized one last time in order to ensure the good dispersion of the active ingredients Adapalene and benzoyl peroxide (microscopic observation revealing a homogeneous dispersion and without aggregates), then the product is conditioned.
  • Step k Correction of the water loss:
  • the loss of water is calculated during the production of the product and the lost water is added with stirring, the stirring is maintained until perfectly homogeneous.
  • the alternative method for preparing the composition according to the invention comprises the following steps:
  • Step a ' Preparation of the single active phase:
  • Steps a) and b) of the main process are grouped so as to obtain step a ') which corresponds to the mixture of at least one retinoid, benzoyl peroxide with water and at least one wetting agent, until 'in perfect dispersion, in order to obtain the unique active phase;
  • Steps c), d), f), g), h), i), j), k) of the main process remain unchanged. Step e) is deleted.
  • Adapalene is observed in fluorescent light while benzoyl peroxide is observed in polarized light.
  • the characterization of the finished product is completed by a measurement of the flow threshold and viscosity.
  • a HAAKE rheometer of type VT550 with a measurement mobile SVDIN is used for the measurement of the flow threshold.
  • the rheograms are carried out at 25 ° C, at the shear rate of 4 s "1 '20s " 1 and 100s “1 ( ⁇ ) and measuring the shear stress.
  • By flow threshold ( ⁇ expressed in Pascal) means the force required (minimum shear stress) to overcome van der Waals cohesive forces and cause flow The flow threshold is equated with the value found at the shear rate of 4s-1.
  • Brookfield RVDVII + or LVDVII + viscometers are used for viscosity measurement.
  • the range of measurable viscosities with the two types of Brookfield are as follows: RVDVI l +: 10OcP - 40McP
  • Example 1 Cream Gel Formulation Containing 0.1% Adapalene and 2.5% Benzoyl Peroxide
  • Example 3 Fluid Cream Gel Formulation Containing 0.3% Adapalene and 1% Benzoyl Peroxide

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EP07872022A 2006-12-21 2007-12-21 Gel creme comprenant au moins un retinoide et du péroxyde de benzoyle Withdrawn EP2125118A2 (fr)

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EP12153666.8A EP2460562B1 (fr) 2006-12-21 2007-12-21 Gel-crème comprenant au moins un rétinoïde et du péroxyde de benzoyle
EP15194565.6A EP3025763B1 (fr) 2006-12-21 2007-12-21 Gel creme comprenant au moins un retinoide et du peroxyde de benzoyle

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FR0655784A FR2910321B1 (fr) 2006-12-21 2006-12-21 Gel creme comprenant au moins un retinoide et du peroxyde de benzole
PCT/FR2007/052613 WO2008087354A2 (fr) 2006-12-21 2007-12-21 Gel creme comprenant au moins un retinoide et du péroxyde de benzoyle

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EP15194565.6A Division EP3025763B1 (fr) 2006-12-21 2007-12-21 Gel creme comprenant au moins un retinoide et du peroxyde de benzoyle

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EP15194565.6A Active EP3025763B1 (fr) 2006-12-21 2007-12-21 Gel creme comprenant au moins un retinoide et du peroxyde de benzoyle
EP12153666.8A Revoked EP2460562B1 (fr) 2006-12-21 2007-12-21 Gel-crème comprenant au moins un rétinoïde et du péroxyde de benzoyle

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KR101500767B1 (ko) 2015-03-17
EP2460562A1 (fr) 2012-06-06
EP3025763A1 (fr) 2016-06-01
US20180263865A1 (en) 2018-09-20
BRPI0719488B1 (pt) 2015-12-01
JP5548456B2 (ja) 2014-07-16
US10925814B2 (en) 2021-02-23
WO2008087354A2 (fr) 2008-07-24
CA2672432A1 (fr) 2008-07-24
AU2007344298A1 (en) 2008-07-24
KR20090091308A (ko) 2009-08-27
US8957112B2 (en) 2015-02-17
EP2460562B1 (fr) 2016-10-05
FR2910321B1 (fr) 2009-07-10
BRPI0719488A2 (pt) 2014-02-18
US20100166852A1 (en) 2010-07-01
ES2599654T3 (es) 2017-02-02
US20150098918A1 (en) 2015-04-09
US9999577B2 (en) 2018-06-19
CN101610815A (zh) 2009-12-23
EP3025763B1 (fr) 2020-06-10
WO2008087354A3 (fr) 2008-11-13
JP2010513428A (ja) 2010-04-30
AU2007344298B2 (en) 2013-07-11
RU2457823C2 (ru) 2012-08-10
MX2009006452A (es) 2009-08-12
FR2910321A1 (fr) 2008-06-27
RU2009128042A (ru) 2011-01-27

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