WO2007031883A2 - Composition contenant au moins un derive d'acide naphtoique et au moins un compose de type polymere de polyurethane ou des derives de ce compose, procedes de fabrication et utilisations de cette composition - Google Patents

Composition contenant au moins un derive d'acide naphtoique et au moins un compose de type polymere de polyurethane ou des derives de ce compose, procedes de fabrication et utilisations de cette composition Download PDF

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Publication number
WO2007031883A2
WO2007031883A2 PCT/IB2006/003852 IB2006003852W WO2007031883A2 WO 2007031883 A2 WO2007031883 A2 WO 2007031883A2 IB 2006003852 W IB2006003852 W IB 2006003852W WO 2007031883 A2 WO2007031883 A2 WO 2007031883A2
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WIPO (PCT)
Prior art keywords
naphthoic acid
composition according
acne
composition
acid derivative
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PCT/IB2006/003852
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English (en)
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WO2007031883A3 (fr
Inventor
Claire Mallard
Eve Ferrara
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Galderma Research & Development
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Publication date
Priority claimed from FR0509493A external-priority patent/FR2890861B1/fr
Priority to KR1020087006011A priority Critical patent/KR101358490B1/ko
Priority to JP2008530661A priority patent/JP5074401B2/ja
Priority to EP06831837A priority patent/EP1933827A2/fr
Priority to BRPI0617045A priority patent/BRPI0617045B8/pt
Priority to MX2008003422A priority patent/MX2008003422A/es
Application filed by Galderma Research & Development filed Critical Galderma Research & Development
Priority to AU2006290364A priority patent/AU2006290364B2/en
Priority to CA002622468A priority patent/CA2622468A1/fr
Publication of WO2007031883A2 publication Critical patent/WO2007031883A2/fr
Publication of WO2007031883A3 publication Critical patent/WO2007031883A3/fr
Priority to US12/076,169 priority patent/US7998467B2/en
Priority to US13/171,872 priority patent/US8435502B2/en
Priority to US13/889,163 priority patent/US8709392B2/en

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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
    • A61K31/185—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
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • 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
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • 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
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • 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
    • A61P17/08—Antiseborrheics
    • 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
    • A61P17/10—Anti-acne agents
    • 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
    • A61P17/12—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
    • 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
    • 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

Definitions

  • the present invention relates to compositions for topical application, to processes for preparing such compositions and to their uses as cosmetic or pharmaceutical products, the said compositions being intended in particular for treating acne.
  • Acne is a common multi-factor pathology that attacks skin rich in sebaceous glands (face, shoulder area, arms and intertriginal areas) . It is the most commonly occurring form of dermatosis. The following five pathogenic factors play a determining role in the formation of acne:
  • acne there are several forms of acne, the common factor of all being attack of the pilosebaceous follicles. Mention may be made especially of acne conglobata, cheloid acne of the nape of the neck, medication- related acne, recurrent miliary acne, necrotic acne, neonatal acne, premenstrual acne, occupational acne, acne rosacea, senile acne, solar acne and simple acne.
  • Simple acne also known as polymorphic juvenile acne, is the most common. It comprises four stages, but passage through all the stages is not obligatory:
  • stage 1 corresponds to comedonic acne characterized by a large number of open and/or closed comedones and of microcysts;
  • stage 2 or papulopustular acne, is of mild to moderate seriousness. It is characterized by the presence of open and/or closed comedones, microcysts, but also red papules and pustules. It mainly affects the face and leaves few scars;
  • stage 3 or papulocomedonic acne, is more serious and extends to the back, the chest and the shoulders. It is accompanied by a larger number of scars ;
  • stage 4 or nodulocystic acne, is accompanied by many scars. It presents nodules and also painful voluminous crimson pustules.
  • acne may be treated with active agents such as anti-seborrhoeic agents and anti-infectious agents, for example benzoyl peroxide (especially the product Eclaran® sold by the company Pierre Fabre) , with retinoids such as tretinoin
  • active agents such as anti-seborrhoeic agents and anti-infectious agents, for example benzoyl peroxide (especially the product Eclaran® sold by the company Pierre Fabre)
  • retinoids such as tretinoin
  • Naphthoic acid derivatives such as, especially, 6- [3- (1-adamantyl) -4-methoxyphenyl] -2- naphthoic acid, which is commonly known as adapalene (the product Differine® sold by the company Galderma) , are widely described and acknowledged as active principles that are just as effective as tretinoin for the treatment of acne.
  • Adapalene also has the advantage of causing fewer side effects, such as phenomena of irritation, dryness of the skin or intolerance, than the other active agents described above, which makes it a product of choice.
  • compositions for increasing the topical penetration of certain active agents by including, in compositions, compounds of polyurethane polymer type or derivatives thereof (patent EP 0 299 758) .
  • the product Avita®, sold by the company Bertek Pharmaceuticals Inc., is an example thereof. It especially contains 0.025% by weight, relative to the total weight of the composition, of tretinoin dissolved in compositions of cream or gel type and containing polyurethane polymers
  • the patent application US2002/01555180 describes a composition comprising as active principle an Extract of Saw Palmetto Berries (SPBE) , and in which adapalene is used as an agent for improving the penetration of the active principle SPBE into the follicles and the sebaceous gland.
  • SPBE Saw Palmetto Berries
  • polyurethane polymers which are known to increase the topical penetration of only certain dissolved active agents (absence of crystals of these active agents when observed by microscope) , can also promote the topical penetration of insoluble compounds, dispersed or suspended in pharmaceutical compositions, especially such as naphthoic acid derivatives .
  • a problem that the invention proposes to solve is that of preparing stable compositions that are less irritant than those of the prior art, comprising at least one naphthoic acid derivative in dispersed form and at least one compound of polyurethane polymer type or derivatives thereof, and also a process for preparing such a composition; the said composition needing to promote the topical penetration of the active principle in dispersed form.
  • a first subject of the invention is a composition for topical application, comprising, in a physiologically acceptable medium, at least one naphthoic acid derivative and at least one compound of polyurethane polymer type or derivatives thereof, the said naphthoic acid derivative being in dispersed form in the said composition, the said composition not comprising any extract of saw palmetto berries.
  • active agent in dispersed form means an active principle in the form of solid particles, suspended in a given vehicle. Such particles are especially greater than 10 ⁇ m in size.
  • a second subject of the invention is a process for preparing a composition for topical application, characterized in that it comprises the step of mixing a physiologically acceptable vehicle comprising at least one naphthoic acid derivative with at least one compound of polyurethane polymer type or derivatives thereof, the said naphthoic acid derivative being in a form dispersed in the said composition.
  • physiologically acceptable vehicle means a vehicle that is compatible with the skin, mucous membranes and/or the integuments.
  • a third subject of the invention is the use of a composition as described above for the preparation of a pharmaceutical composition for treating and/or preventing dermatological complaints associated with a keratinization disorder that has a bearing on cell differentiation and proliferation, especially for treating comedonic acne, simple acne, papulocomedonic acne, nodulocystic acne, polymorphic acne, acne rosacea, acne conglobata, senile acne, and secondary acnes such as solar acne, medication-related acne or occupational acne.
  • a composition comprises, in a physiologically acceptable medium, at least one naphthoic acid derivative and at least one compound of polyurethane polymer type or derivatives thereof, the said naphthoic acid derivative being in a form dispersed in the said composition, it shows good chemical stability, high anti-comedolytic efficacy and also good tolerance.
  • FIGS. 1 to 4 show the results of a study aimed at comparing the irritant power of a reference gel containing 0.1% adapalene with that of three 0.1% adapalene formulations in gel form comprising a polyurethane polymer at various concentrations, and also placebos thereof, on the skin of BALB/c mouse ear after repeated topical applications for
  • Figures 5 to 8 show the results of a study aimed at evaluating the comedolytic activity of a reference gel containing 0.1% adapalene and of two 0.1% adapalene formulations in gel form with a polyurethane polymer at various concentrations, and also placebos thereof, on dorsal skin of RHINO FVB/N RJ-hr rh mice (Rhino) after repeated topical applications for 18 days.
  • composition according to the invention comprises at least one naphthoic acid derivative and at least one compound of polyurethane polymer type or derivatives thereof .
  • Naphthoic acid is a compound of formula:
  • naphthoic acid derivative means the compounds of formula (I) :
  • R represents a hydrogen atom, a hydroxyl radical, a branched or unbranched alkyl radical containing from 1 to 4 carbon atoms, an alkoxy radical containing from 1 to 10 carbon atoms or a substituted or unsubstituted cycloaliphatic radical.
  • linear or branched alkyl radical containing from 1 to 4 carbon atoms preferably means methyl, ethyl, propyl and butyl radicals.
  • alkoxy radical containing from 1 to 10 carbon atoms preferably means methoxy, ethoxy, propoxy, butoxy, hexyloxy and decyloxy radicals.
  • cycloaliphatic radical preferably means monocyclic or polycyclic radicals such as the 1-methyl- cyclohexyl radical or the 1-adamantyl radical.
  • the abovementioned naphthoic acid derivatives are generally in a form dispersed in the composition according to the invention.
  • the insoluble naphthoic acid derivatives are thus uniformly distributed in the composition according to the invention.
  • the naphthoic acid derivatives are used at concentrations of less than or equal to 10% by weight relative to the total weight of the composition, and preferably between 0.001% and 10% by weight relative to the total weight of the composition, preferentially between 0.01% and 5%, more preferentially between 0.05% and 2% and most preferentially from 0.1% to 0.3% by weight relative to the total weight of the composition.
  • concentrations less than or equal to 10% by weight relative to the total weight of the composition, and preferably between 0.001% and 10% by weight relative to the total weight of the composition, preferentially between 0.01% and 5%, more preferentially between 0.05% and 2% and most preferentially from 0.1% to 0.3% by weight relative to the total weight of the composition.
  • the naphthoic acid derivative used in the compositions according to the invention is adapalene.
  • the adapalene concentration used in the composition according to the invention is then between 0.01% and 0.5%, and preferentially equal to 0.03%, more preferentially between 0.1% and 0.3% and in particular at a concentration of 0.1% and at a concentration of 0.3%.
  • the naphthoic acid derivative (s) is (are) the only active principle (s) present in the composition according to the invention.
  • adapalene is the only active principle of the composition.
  • composition according to the invention also comprises compounds of polyurethane polymer type or derivatives thereof.
  • polyurethane polymers means polyalkylene glycols as described in patent EP 0 299 758, and sold by the company Bertek Pharmaceuticals Inc.
  • the polyurethane polymers according to the invention have unique properties that give them advantageous properties for applications in cosmetics and pharmaceuticals. Specifically, polyurethane polymers significantly influence the deposition of certain agents onto and into the skin, by virtue of their high molecular weight. Moreover, polyurethane polymers preferentially remain in the upper layers of the skin.
  • polyurethane polymers that may be included in the compositions according to the invention, mention may be made of the polyurethane polymers of general formula:
  • R is CH3 or H; n is an integer chosen such that the polyurethane polymer has a molecular mass at least equal to 1000, and n is advantageously between 5 and 55; and m is a number between 1 and 6 inclusive.
  • polyurethane polymers that may be included in the compositions according to the invention, mention may be made of polyolprepolymer-2
  • PP-2 polyolprepolymer-14
  • PP-14 polyolprepolymer-14
  • polyolprepolymer-14 PP-14
  • poly [oxy (methyl-1, 2-ethanediyl) ] polymer with 1, 1 ' -methylenebis [4-isocyanatocyclo- hexane]
  • polyolpre ⁇ olymer-15 PP-15
  • poly (oxy-1, 2-ethanediyl) ⁇ -hydro- ⁇ -hydroxy-, polymer with 1,1' -methylenebis [4-isocyanatocyclohexane]
  • polyolprepolymer-2 (PP-2) will advantageously be chosen.
  • the compounds of polyurethane polymer type or derivatives thereof are used at concentrations of less than or equal to 20% and preferably between 0.5% and 20% by weight, more preferentially between 1% and 10% by weight and in particular 1%, 3%, 7% or 10% by weight relative to the total weight of the composition, and preferentially at a concentration lower than or equal to 7%.
  • concentrations of polyurethane polymers advantageously make it possible to reduce the toxicity and the general irritation of the composition according to the invention.
  • polyurethane polymers in the composition according to the invention which are deposited in the stratum corneum, allows the formation of a reservoir in the upper part of the skin. This reservoir allows the naphthoic acid derivatives to be released gradually into the deeper layers of the epidermis.
  • the polyurethane polymers contained in the compositions according to the invention have anti-irritant and moisturizing properties that may be particularly advantageous in the case of adapalene formulations. The reason for this is that naphthoic acid derivatives may be irritant and have a dehydrating action on the skin. It is thus advantageous to reduce the irritation induced in order to be able to increase the doses.
  • compositions of the present invention may be in any galenical form normally used for topical application, especially in the form of aqueous, aqueous-alcoholic or oily dispersions, dispersions of the lotion type, aqueous, anhydrous or lipophilic gels, emulsions of liquid or semi-liquid consistency of the milk type, obtained by dispersing a fatty phase in an aqueous phase (O/W) or vice versa (W/O) , or suspensions or emulsions of soft, semi-liquid or solid consistency of the cream, cream-gel or pomade type, or alternatively microemulsions, microcapsules, microparticles or vesicular dispersions of ionic and/or nonionic type.
  • aqueous, aqueous-alcoholic or oily dispersions dispersions of the lotion type, aqueous, anhydrous or lipophilic gels, emulsions of liquid or semi-liquid consistency of the milk type, obtained by dispersing a fatty
  • compositions according to the invention are in the form of lotions, cream-gels, gels or creams.
  • compositions according to the invention A person skilled in the art will take care to select the excipients constituting the compositions according to the invention as a function of the desired galenical form and such that the advantageous properties of the composition according to the invention are respected.
  • composition according to the invention may also especially comprise one or more of the following ingredients: a) one or more gelling agents or suspending agents, b) one or more chelating agents, c) one or more wetting agents, d) one or more preserving agents.
  • gelling agents or suspending agents that may be included in the compositions according to the invention
  • Preferred gelling agents are the carbomers sold especially under the names Carbopol 974P NF and Carbopol 980 NF.
  • chelating agents include ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTPA), ethylenediaminebis (O-hydroxyphenylacetic acid) (EDBHA), hydroxy-2-ethylenediaminetriacetic acid (HEDTA) , ethyldiaminebis (O-hydroxy-p-methylphenyl) acetic acid
  • EDTA ethylenediaminetetraacetic acid
  • DTPA diethylenetriaminepentaacetic acid
  • EDBHA ethylenediaminebis (O-hydroxyphenylacetic acid)
  • HEDTA hydroxy-2-ethylenediaminetriacetic acid
  • ethyldiaminebis O-hydroxy-p-methylphenyl
  • EDBHMA ethylenediaminebis (5-carboxy-2- hydroxyphenyl) acetic acid
  • EABCHA ethylenediaminebis (5-carboxy-2- hydroxyphenyl) acetic acid
  • a preferred chelating agent that may be mentioned is ethylenediaminetetraacetic acid (EDTA) sold especially under the name Titriplex III®.
  • EDTA ethylenediaminetetraacetic acid
  • Titriplex III® ethylenediaminetetraacetic acid
  • the role of which is to reduce the surface tension and to allow greater spreading of the liquid compounds such as propylene glycol, dipropylene glycol, propylene glycol dipelargonate, lauroglycol and ethoxydiglycol, alone or as a mixture, are preferentially used, without this list being limiting.
  • a preferred wetting agent that may be mentioned is propylene glycol.
  • non-limiting examples include benzoic acid and derivatives thereof with benzyl alcohol, benzalkonium chloride, sodium benzoate, bronopol, chlorhexidine, chlorocresol and derivatives thereof, ethyl alcohol, phenethyl alcohol, phenoxyethanol, potassium sorbate, diazolidinylurea, parabens such as propyl paraben or methyl paraben, taken alone or as mixtures.
  • Preferred preserving agents include parabens and phenoxyethanol or benzalkonium chloride, alone or as a mixture.
  • composition according to the invention may comprise one or more emulsifiers.
  • Surfactant emulsifiers are amphiphilic compounds containing a hydrophobic portion with affinity for oil and a hydrophilic portion with affinity for water, thus creating a bond between the two phases. Ionic or nonionic emulsifiers thus stabilize oil/water emulsions by becoming adsorbed at the interface and by forming lamellar liquid crystal layers.
  • the emulsifying power of nonionic surfactants is closely linked to the polarity of the molecule. This polarity is defined by the HLB (hydrophilic/lipophilic balance ) .
  • a high HLB indicates that the hydrophilic fraction is predominant and, conversely, a low HLB indicates that the lipophilic portion is predominant.
  • HLB values of greater than about 10 correspond to hydrophilic surfactants.
  • Surfactants may be classified, according to their structure, under the generic terms “ionic” (anionic, cationic or amphoteric) or “nonionic”.
  • Nonionic surfactants are surfactants that do not dissociate into ions in water and are thus insensitive to pH variations .
  • Nonionic surfactants are particularly suitable for preparing emulsions of oil-in-water type, which are the subject of the present invention.
  • the emulsifying system of which the emulsion of the invention is composed comprises at least one nonionic surfactant, with a hydrophilic predominant fraction, i.e. with a high HLB value, of greater than about 10.
  • nonionic surfactants with a high HLB value examples include sorbitan esters such as
  • the said high-HLB nonionic surfactants have an HLB of between 10 and 18.
  • low-HLB nonionic surfactants examples include sorbitan esters, such as sorbitan monostearate (sold under the name Span 60 by Unichema) , glycerol esters (sold under the name Cutina
  • GMSVPH by Cognis
  • Cutina glyceryl monostearate
  • the said low-HLB nonionic surfactants have an HLB of less than 10.
  • the nonionic surfactants may be used alone or as a mixture of two or more of them to form the emulsifying system of which the emulsion of the invention is composed.
  • one or more high-HLB nonionic surfactant/low-HLB nonionic surfactant pairs will be used as emulsifying system: it may in particular be a nonionic emulsifying system comprising at least one nonionic surfactant with an HLB of greater than about 10 and at least one nonionic surfactant with an HLB of less than about 10.
  • the ratio of each of the two surfactants forming the abovementioned pair is usually determined by calculating the required HLB of the fatty phase used.
  • emulsifiers that may be mentioned include hydrophilic emulsifiers such as Tween 80, glyceryl stearate & PEG-100 stearate sold under the name Arlacel 165FL® by the company Uniqema; PEG 6 stearate and PEG
  • lipophilic emulsifiers such as Glucate SS
  • composition according to the invention may also comprise a fatty phase.
  • This fatty phase may comprise, for example, plant oils, mineral oils, animal oils, synthetic oils or silicone oils, and mixtures thereof.
  • mineral oils examples include liquid paraffins of various viscosities such as Primol 352®, Marcol 82® and Marcol 152® sold by the company Esso.
  • Plant oils that may be mentioned include sweet almond oil, palm oil, soybean oil, sesame seed oil and sunflower oil.
  • Animal oils that may be mentioned include lanolin, squalene, fish oil, mink oil with, as a derivative, squalane sold under the name Cosbiol® by the company Laserson.
  • Synthetic oils that may be mentioned include esters such as cetearyl isononanoate, for instance the product sold under the name Cetiol SN® by the company Cognis France, diisopropyl adipate, for instance the product sold under the name Ceraphyl 230® by the company ISF, isopropyl palmitate, for instance the product sold under the name Crodamol IPP® by the company Croda, isopropyl adipate, for instance the product sold under the name Crodamol DA by the company Croda and caprylic/capric triglyceride such as Miglyol 812® sold by the company H ⁇ ls/Lambert Riviere.
  • esters such as cetearyl isononanoate, for instance the product sold under the name Cetiol SN® by the company Cognis France
  • diisopropyl adipate for instance the product sold under the name Ceraphyl 230® by the company ISF
  • Silicone oils that may be mentioned include a dimethicone, for instance the product sold under the name Dow Corning 200 Fluid®, a cyclomethicone, for instance the product sold under the name Dow Corning 244 Fluid® by the company Dow Corning or the product sold under the name Mirasil CM5® by the company SACI- CFPA.
  • Solid fatty substances such as natural or synthetic waxes may also be used. In this case, the person skilled in the art will adapt the heating temperature of the preparation as a function of the presence or absence of these solids.
  • liquid paraffins and more particularly Marcol 152® and Miglyol 812® are preferred.
  • compositions of the invention may also comprise any additive usually used in cosmetics or pharmaceuticals, such as surfactants, neutralizers, sunscreens, antioxidants, fillers, electrolytes, dyes, common mineral or organic acids or bases, fragrances, essential oils, cosmetic active agents, moisturizers, vitamins, sphingolipids, self-tanning compounds such as DHA, calmatives and skin-protecting agents such as allantoin, and pro-penetrating agents, or a mixture thereof.
  • the composition according to the invention does not comprise any of the following active agents: glycolic acid, salicylic acid, retinol, tretinoin, retinaldehyde, azelaic acid and tazarotene. Needless to say, a person skilled in the art will take care to select this or these optional additional compound(s), and/or the amount thereof, such that the advantageous properties of the composition according to the invention are not, or are not substantially, adversely affected.
  • additives may be present in the composition in a proportion of from 0.001% to 20% by weight relative to the total weight of the composition.
  • the composition is in the form of an oil-in-water (0/W) emulsion of lotion, cream or cream-gel type and comprises : from 0.1% to 0.3% of a naphthoic acid derivative; - from 1% to 10% of one or more polyurethane polymers or derivatives; from 0.1% to 3% of gelling agents or suspending agents; - from 0.01% to 1.5% of chelating agents; from 0.1% to 10% of a wetting agent; from 0.1% to 20% of an emollient; from 0.1% to 30% of fatty phase; from 0.01% to 3% of preserving agents; - from 0 to 10% of emulsifiers .
  • the composition is in gel form and comprises: from 0.1% to 0.3% of a naphthoic acid derivative; - from 1% to 10% of one or more polyurethane polymers or derivatives; from 0.1% to 3% of gelling agents; from 0.01% to 1.5% of chelating agents; from 1% to 10% of a wetting agent; - from 0.01% to 3% of preserving agents.
  • the composition is in lotion form and comprises in water: from 0,1% to 0,3% of a naphtoic acid derivative ;
  • a subject of the present invention is also the composition as described above, as medicament.
  • a subject of the invention is also a process for preparing a composition as described above.
  • Such a process is characterized in that it comprises the step of mixing a physiologically acceptable vehicle comprising at least one naphthoic acid derivative with at least one compound of polyurethane polymer type or derivatives thereof, the said naphthoic acid derivative being in a form dispersed in the said composition.
  • compositions according to the invention are performed in 2 or 4 steps according to the chosen galenical form, the 2 additional steps being performed solely for the preparation of forms of emulsion type such as creams, lotions or cream-gels.
  • the introduction of the polyolprepolymer into one or other of the steps is dependent on the lipophilic or hydrophilic nature of the polyolprepolymer.
  • the polyolprepolymer of the type PP-2 of lipophilic nature is introduced into the fatty phase for the emulsions and after the neutralization step for the gels.
  • the polyolprepolymer of the type PP-15, which is hydrophilic, is introduced into the active aqueous phase after dispersing of the gelling agent (s).
  • composition according to the invention is thus performed according to the following process:
  • the naphthoic acid derivative is mixed with at least one wetting agent, at least one chelating agent, at least one gelling agent, optionally hydrophilic emulsifiers and emollients, in water, until the said naphthoic acid derivative is fully dispersed, in order to obtain the aqueous active phase;
  • At least lipophilic emulsifiers, oils and/or solid fatty substances are mixed with preserving agents, in order to obtain the fatty phase;
  • the said fatty phase obtained in b) is introduced into the aqueous active phase obtained in a) in order to obtain an emulsion;
  • a gelling-agent neutralizer is introduced into the emulsion obtained in c) or into the aqueous phase obtained in a) in order to obtain the desired pH, and the remaining amount of water is added; the compound of polyurethane polymer type or derivatives thereof being introduced into the aqueous active phase obtained in a) or into the fatty phase obtained in step b) or during step d) as a function of its lipophilic or hydrophilic nature.
  • the process for preparing the composition according to the invention comprises the following steps:
  • Step a preparation of the aqueous active phase:
  • the hydrophilic emulsifiers such as Arlacel
  • Step b (optional) : Preparation of the fatty phase:
  • the lipophilic emulsifiers such as Glucate SS, Glucamate SSE 20 or Brij 721, Tefose 1500, Eumulgin B2 PH
  • the oily compounds such as isostearic olepal, Cetiol SN, Crodamol DA, Speziol C18, Miglyol 812 or Cosbiol
  • the preserving agents such as phenoxyethanol and propyl paraben
  • the fatty phase is introduced gently into the aqueous phase at a temperature of 60 0 C and with stirring using a deflocculator, in order to perform the emulsification. Heating is maintained for 5 minutes and the hotplate is then removed to allow the product to cool gently. The stirring is adjusted as a function of the viscosity.
  • Steps 2 and 3 are optional and are performed solely for the preparation of forms of emulsion type such as creams, lotions or cream-gels.
  • the gelling-agent neutralizer (such as triethanolamine or 10% sodium hydroxide solution) is introduced, if necessary, at 4O 0 G, up to a pH of 5.5 + 0.5.
  • the product then has a thicker consistency.
  • the pH is again checked. If it is within the norms, the sufficient quantity of water is added.
  • the product is homogenized a final time in order to ensure good dispersion of the adapalene active principle (observation by microscope revealing a uniform dispersion free of aggregates) , and the product is then packaged.
  • the compound of polyurethane polymer type is preferably a polyolprepolymer that is introduced during step a) (for the gel or emulsion formulations comprising a hydrophilic polymer) or during step b) (for the emulsion formulations comprising a lipophilic polymer) , or during step d) (for the gel formulations comprising a lipophilic polymer) as a function of its lipophilic or hydrophilic nature.
  • 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 preparation of a pharmaceutical composition for treating and/or preventing dermatological complaints associated with a keratinization disorder that has a bearing on cell differentiation and proliferation, especially for treating simple acne, comedonic acne, papulopustular acne, papulocomedonic acne, nodulocystic acne, acne conglobata, cheloid acne of the nape of the neck, recurrent miliary acne, necrotic acne, neonatal acne, occupational acne, acne rosacea, senile acne, solar acne and medication-related acne.
  • the invention relates to the use of a composition as described above for the preparation of a pharmaceutical composition for preventing or treating simple acne.
  • the said compositions according to the invention are preferentially administered topically.
  • the invention also relates to the cosmetic use of a composition according to the invention for the treatment of acne-prone skin, for combating the greasy appearance of the skin or the hair, in the protection against the harmful aspects of sunlight or in the treatment of physiologically greasy skin, or for preventing and/or combating light-induced or chronological ageing.
  • Example 1 Manufacture of a formulation of gel type containing adapalene and polyurethane polymer
  • the manufacture is performed in 4 steps:
  • Step 1 preparation of the aqueous phase:
  • Purified water, EDTA and methyl paraben are introduced into a beaker.
  • the beaker is then placed on a water bath (or on a hotplate) in order to bring the solution to 80°C + 5°C, allowing dissolution of the paraben.
  • the beaker is stirred with a Rayneri blender equipped with a deflocculating paddle until totally dispersed.
  • Carbopol 980 NF is then added as a shower and the mixture is stirred until fully dispersed.
  • Propylene glycol and Synperonic PE/L62 are introduced into an additional beaker.
  • Adapalene is then introduced and the beaker is stirred using an Ultra-Turrax blender (paddle: 540 rpm; turbomixer 20 500 rpm) .
  • an Ultra-Turrax blender (paddle: 540 rpm; turbomixer 20 500 rpm) .
  • the adapalene is fully dispersed (observation by microscope revealing a uniform dispersion free of aggregates) , the phase is then added to the rest of the formulation.
  • Step 3 Neutralization: a sufficient amount of aqueous 10% (m/m) sodium hydroxide solution is added to the formula phase in order to bring the formulation to pH 5.5 ⁇ 0.5.
  • Step 4 The polyurethane polymer (polyolprepolymer-2) is introduced.
  • the mixture is made up to the required volume with a sufficient quantity of water.
  • Example 2 Formulation of gel type containing 0.1% adapalene and polyolprepolymer-2 :
  • Example 3 Formulation of gel type containing 0.1% adapalene and polyolprepolymer-2 ;
  • Example 4 Formulation of gel type containing 0.1% adapalene and polyolprepolymer-2 :
  • Example 5 Chemical stability of the formulation according to Example 2 :
  • Example 2 The chemical stability of the gel formulation described in Example 2 is measured by HPLC over 6 months at room temperature (RT) . The results show that this composition is chemically stable for 6 months at room temperature.
  • Example 6 Chemical stability of the formulation according to Example 3 :
  • Example 3 The chemical stability of the gel formulation described in Example 3 is measured by HPLC over 6 months at room temperature (RT) . The results show that this composition is chemically stable for 6 months at room temperature, and at constant pH.
  • Example 7 General process for manufacturing an oil-in- water emulsion formulation of cream-gel, cream or lotion type according to the invention
  • the manufacture is performed in 4 steps:
  • Step 1 preparation of the aqueous active phase:
  • Purified water Purified water, the active principle (adapalene) , the hydrophilic emulsifiers such as Arlacel 165FL and Tween 80, the emollients such as glycerol and propylene glycol, the wetting agents such as Synperonic PE/L44, the chelating agent such as EDTA and .
  • the gelling agent (s) such as Carbopol, Pemulen TRl, Xantural, Methocel or Simulgel 600 are introduced with stirring using a deflocculator into a beaker that will serve as receiver for the finished product. The mixture is stirred without heating until fully dispersed. When the mixture is homogeneous, the aqueous phase is brought to 60 °C on a water bath and the methyl paraben is introduced.
  • Step 2 Preparation of the fatty phase:
  • the lypophilic emulsifiers such as Glucate SS/Glucamate SSE 20 or Brij 721, Tefose 1500, Eumulgin B2 PH, the oily compounds such as isostearic olepal, Cetiol SN, Crodamol DA, Speziol C18, Miglyol 812 or Cosbiol and the preserving agents such as phenoxyethanol and propyl paraben are introduced with stirring using a deflocculator into an additional beaker.
  • the mixture is brought to 60 0 C on a water bath and, after homogenization, the volatile silicone, if present, is introduced into the composition.
  • Step 3 Introduction of the polyolprepolymer:
  • polyolprepolymer-2 which is lipophilic
  • polyolprepolymer-15 which is hydrophilic
  • it will be introduced into the aqueous phase, after dispersion of the gelling agent (s).
  • the fatty phase is introduced gently into the aqueous phase at a temperature of 60 0 C and with stirring using a deflocculator, to perform the emulsification.
  • Heating is maintained for 5 minutes and the hotplate is then removed to allow the product to cool gently.
  • the stirring is regulated as a function of the viscosity.
  • the gelling-agent neutralizer such as triethanolamine or 10% sodium hydroxide solution
  • the pH is again checked. If it is within the norms, the sufficient quantity of water is added.
  • the product is homogenized a final time in order to ensure good dispersion of the active principle adapalene (observation by microscope revealing a uniform dispersion free of aggregates) and the product is then packaged.
  • Example 8 Formulation of cream type containing 0.1% adapalene and polyolprepolymer-2
  • Example 9 Formulation of cream type containing 0.1% adapalene and polyolprepolymer-2
  • Example 10 Formulation of cream type containing 0.1% adapalene and pol ⁇ olprepol ⁇ mer-15
  • Example 11 Formulation of cream type containing 0.1% adapalene and polyolprepolymer-15 The formula is prepared according to the procedure described in Example 7.
  • Example 12 Formulation of lotion type containing 0.1% adapalene and polyolprepolymer-2
  • Example 13 Formulation of lotion type containing 0.1% adapalene and polyolprepoly ⁇ ter-2
  • Example 14 Formulation of lotion type containing 0.1% adapalene and polyolprepolymer-2
  • Example 15 Formulation of lotion type containing 0.1% adapalene and polyolprepolymer-2
  • Example 16 Formulation of lotion type containing 0.1% adapalene and polyolprepolymer-2
  • Example 17 Formulation of lotion type containing 0.1% adapalene and polyolprepolymer-2
  • Example 18 Formulation of lotion type containing 0.3% adapalene and polyolprepolymer-2
  • Example 19 Formulation of cream-gel type containing
  • Example 20 Formulation of cream-gel type containing 0.3% adapalene and polyolprepolymer-2
  • Example 21 Formulation of cream-gel type containing 0.3% adapalene and polyolprepolymer-2
  • Example 22 Formulation of lotion type containing 0.1% adapalene and 3% PP-2
  • Example 23 Formulation of lotion type containing 0.3% adapalene and 3% PP-2
  • composition is thus chemically and physically stable.
  • Example 24 Formulation of the lotion type cream- gel containing 0.3% adapalene and 3% PP-2
  • composition is thus physically and chemically stable.
  • Example 25 Formulation of the type lotion containing 0.3% adapalene and 3% PP-2
  • composition is thus chemically and physically stable.
  • Example 26 Formulation of the type cream-gel containing 0.3% adapalene and 3% PP-2
  • composition is thus physically and chemically stable.
  • Example 27 Formulation of the type lotion containing 0.3% adapalene and 3% PP-2
  • composition is thus physically and chemically stable .
  • the present study is aimed at comparing in vitro the release-penetration into human skin without occlusion of adapalene formulated at 0.1% (m/m) in a gel containing 1% PP-2 (formulation according to Example 2), formulated at 0.1% (m/m) in a gel containing 3% PP-2 (formulation according to Example 3) and in a reference gel containing 0.1% adapalene.
  • the absorption studies were performed using excized human skin mounted under static conditions for a period of 16 hours. Three samples of skin obtained from women (68 years old) were used. An amount of 10 mg of each formula (10 ⁇ g of adapalene) was applied to a 1 cm 2 area of skin. The adapalene concentrations in the fluid fractions collected over time and remaining in the skin at the end of the study were evaluated by the HPLC method with fluorescence detection (based on a validated method. Quantification limit: 1 ng.mlT 1 ) .
  • the present study is aimed at comparing the irritant power of a reference gel containing 0.1% adapalene with that of three 0.1% adapalene formulations in gel form containing a polyurethane polymer at various concentrations, and also placebos thereof, on the skin of the ear of the BALB/c mouse after repeated topical applications for 6 days.
  • the daily topical application (20 ⁇ l) of the test products is performed on the inner face of the ear of
  • mice BALB/c mice divided into ten groups (female mice about
  • test products are:
  • Group 1 acetone (control vehicle)
  • Group 2 placebo reference gel (control vehicle)
  • Group 3 placebo formulation (without 0.1% adapalene) of Example 2 (1% PP-2) (control vehicle)
  • Group 4 placebo formulation (without 0.1% adapalene) of Example 3 (3% PP-2) (control vehicle)
  • Group 5 placebo formulation (without 0.1% adapalene) of Example 4 (10% PP-2) (control vehicle)
  • Group 8 formulation of Example 3 (3% PP-2)
  • Group 9 placebo formulation of Example 4 (10% PP-2)
  • the evaluation is performed by measuring the thickness of the ear by means of the Oditest and by clinical observation of the animals from the 2 nd to the 19 th day.
  • FIG. 1 shows the kinetics of the mean thickness of the mouse ears between the 2 nd and 19 th days for the various test products with:
  • Figure 3 shows the kinetics of the mean thickness of the mouse ears between the 2 nd and 19 th days for the various test products with:
  • Example 3 is less irritant than the reference gel containing 0.1% adapalene.
  • This formulation according to Example 3 (3% PP-2) also shows an increase in the area under the curve of only 19% relative to its placebo (placebo Example 3 (3% PP-2)).
  • Example 4 is less irritant than the reference gel containing 0.1% adapalene.
  • This formulation according to Example 3 (3% PP-2) similarly shows an increase in the area under the curve of 22% relative to its placebo (placebo Example 4 (3% PP-2)).
  • placebos are not irritant and show fully superposable kinetics;
  • test formulations described in Examples 2, 3 and 4 increase the thickness of the ear by 15%, 19% and 22%, respectively, relative to their placebos. They are all less irritant than the "reference gel containing 0.1% adapalene" and difficult to differentiate from each other.
  • the table below compares the various formulations containing 0.1% adapalene with the untreated placebo so as to demonstrate the effect of the polyurethane polymer on the tolerance.
  • polyurethane polymer 1 irrespective of the content of polyurethane polymer 1: 3% or 10%, the formulations are tolerated 2 times better than in the absence of polyurethane polymers .
  • the present study is aimed at evaluating the comedolytic activity of the reference gel containing 0.1% adapalene and of two 0.1% adapalene formulations in gel form with a polyurethane polymer at different concentrations, and also their placebos, on the skin of the back of RHINO FVB/N RJ-hr rh mice (Rhino) after repeated topical applications for 18 days.
  • the daily topical application (50 ⁇ l) of the test products is performed on the skin of the back of Rhino mice divided into seven groups (approximately 7-week- old mice) at a rate of one application per day for
  • test products are:
  • Group 2 placebo formulation (without 0.1% adapalene) of Example 3 (3% PP-2) (control vehicle)
  • Group 3 acetone + 0.01% (m/m) 2- (5, 5, 8, 8-tetramethyl- 5,6,7, 8-tetrahydronaphthalen-2-yl)benzo [b] thiophene-6- carboxylic acid (positive control)
  • Group 4 acetone + 0.1% (m/m) adapalene
  • 5 reference gel containing 0.1% adapalene
  • Group 6 formulation of Example 2 (1% PP-2)
  • Group 7 formulation of Example 3 (3% PP-2)
  • the tolerance evaluation is made by clinical observation of the dorsal epidermis with the following observation parameters: oedema, erythema and squamae 3 times a week for 19 days.
  • the comedolytic activity is evaluated by measuring the transepidermal water loss (TWL) on days D4 , DIl and D19, by measuring the thickness of the epidermis, by counting the number of comedones/cm and by weighing the animals on days Dl, D4, DlI and D19.
  • TWL transepidermal water loss
  • Figure 5 shows the results of the areas under the curve ffoorr tthhee ttoolleerraannccee eevvaalluuaattiioonn bbeettwweeeen the 1 st and 19 th day for the various test products with:
  • FIG. 6 shows the results of the areas under the curve (AUC) for the transepidermal water loss (TWL) after 18 days of topical treatment for the various test products with:
  • the TWL quantifies the impairment in the skin barrier by measuring the gradient of water vapour that is established in a layer 10 mm thick above the surface of the skin.
  • Figure 7 shows the results of the measurement of the thickness of the epidermis after 18 days of topical treatment for the various test products with:
  • Figure 8 shows the results of the counting of the number of comedones per centimetre (cm) on the back of Rhino mice after 18 days of topical treatment for the various test products with:
  • the present study is aimed at comparing in vitro the release-penetration into human skin without occlusion of adapalene formulated at 0.3% (m/m) in a lotion containing 3% PP-2 (formulation according to Example
  • the absorption studies were performed using excized human skin mounted under static conditions for a period of 16 hours. Three samples of skin obtained from women (68 years old) were used. An amount of 30 mg of each formula (30 ⁇ g of adapalene) was applied to a 1 cm 2 area of skin. The adapalene concentrations in the fluid fractions collected over time and remaining in the skin at the end of the study were evaluated by the HPLC method with fluorescence detection (based on a validated method. Quantification limit: 1

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Abstract

L'invention concerne une composition à application topique, contenant, dans un fluide physiologiquement acceptable, au moins un dérivé d'acide naphtoïque et au moins un composé de type polymère de polyuréthane ou des dérivés de ce composé. La composition selon l'invention est caractérisée en ce que le dérivé d'acide naphtoïque se présente sous forme dispersée dans la composition. La composition selon l'invention est particulièrement destinée aux domaines pharmaceutiques et cosmétiques humains.
PCT/IB2006/003852 2005-09-16 2006-09-15 Composition contenant au moins un derive d'acide naphtoique et au moins un compose de type polymere de polyurethane ou des derives de ce compose, procedes de fabrication et utilisations de cette composition WO2007031883A2 (fr)

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CA002622468A CA2622468A1 (fr) 2005-09-16 2006-09-15 Composition contenant au moins un derive d'acide naphtoique et au moins un compose de type polymere de polyurethane ou des derives de ce compose, procedes de fabrication et utilisations de cette composition
JP2008530661A JP5074401B2 (ja) 2005-09-16 2006-09-15 少なくとも１つのナフトエ酸誘導体および少なくとも１つのポリウレタンポリマータイプの化合物またはその誘導体を含む組成物、その調製方法、およびその使用
EP06831837A EP1933827A2 (fr) 2005-09-16 2006-09-15 Composition contenant au moins un derive d'acide naphtoique et au moins un compose de type polymere de polyurethane ou des derives de ce compose, procedes de fabrication et utilisations de cette composition
BRPI0617045A BRPI0617045B8 (pt) 2005-09-16 2006-09-15 composição, processo para preparar uma composição, uso de uma composição e uso cosmético de uma composição
MX2008003422A MX2008003422A (es) 2005-09-16 2006-09-15 Composiciones que comprenden al menos un derivado de acido naftoico y al menos un compuesto de tipo polimero de poliuretano o derivados del mismo, procesos de preparacion y composiciones que comprenden al menos un derivado de acido naftoico y al meno
KR1020087006011A KR101358490B1 (ko) 2005-09-16 2006-09-15 하나 이상의 나프토산 유도체 및 하나 이상의 폴리우레탄중합체 유형 화합물 또는 이의 유도체를 함유하는 조성물,이의 제조 방법 및 이의 용도
AU2006290364A AU2006290364B2 (en) 2005-09-16 2006-09-15 Composition comprising at least one naphthoic acid derivative and at least one compound of polyurethane polymer type or derivatives thereof, preparation processes therefor and uses thereof
US12/076,169 US7998467B2 (en) 2005-09-16 2008-03-14 Cosmetic/dermatological compositions comprising naphthoic acid compounds and polyurethane polymers
US13/171,872 US8435502B2 (en) 2005-09-16 2011-06-29 Cosmetic/dermatological compositions comprising naphtholic acid compounds and polyurethane polymers
US13/889,163 US8709392B2 (en) 2005-09-16 2013-05-07 Cosmetic/dermatological compositions comprising naphthoic acid compounds and polyurethane polymers

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FR0509493A FR2890861B1 (fr) 2005-09-16 2005-09-16 Compositions comprenant au moins un derive de l'acide naphtoique et au moins un compose de type polymeres de polyurethanes ou des derives de celui-ci, leurs procede de preparation, et leur utilisation
US72527905P 2005-10-12 2005-10-12
US60/725,279 2005-10-12

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US9814690B2 (en) 2001-12-21 2017-11-14 Galderma Research & Development Gel composition for treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt
FR2916975A1 (fr) * 2007-06-11 2008-12-12 Galderma Res & Dev Compositions comprenant au moins un compose retinoide, un compose anti-irritant et du peroxyde de benzoyle, et leurs utilisations
FR2916966A1 (fr) * 2007-06-11 2008-12-12 Galderma Res & Dev Compositions comprenant au moins un compose retinoide, un compose anti-irritant et du peroxyde de benzoyle, et leurs utilisations
WO2009007341A3 (fr) * 2007-07-06 2009-11-19 Galderma Research & Development Compositions destinées à l'application topique pour le traitement des troubles de la kératinisation
WO2009007341A2 (fr) * 2007-07-06 2009-01-15 Galderma Research & Development Compositions destinées à l'application topique pour le traitement des troubles de la kératinisation
US8716341B2 (en) 2007-07-06 2014-05-06 Galderma Research & Development Topically applicable compositions for the treatment of keratinization disorders
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JP5074401B2 (ja) 2012-11-14
AU2006290364A1 (en) 2007-03-22
JP2009508843A (ja) 2009-03-05
JP2012184258A (ja) 2012-09-27
AU2006290364B2 (en) 2012-07-05
MX2008003422A (es) 2008-03-27
CA2622468A1 (fr) 2007-03-22
WO2007031883A3 (fr) 2007-09-13
RU2421216C2 (ru) 2011-06-20
EP1933827A2 (fr) 2008-06-25
RU2008114840A (ru) 2009-10-27

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