EP1965872A2 - Zusammensetzungen mit mindestens einer retinoid-verbindung und mindestens einer reizhemmenden verbindung sowie anwendungen davon - Google Patents

Zusammensetzungen mit mindestens einer retinoid-verbindung und mindestens einer reizhemmenden verbindung sowie anwendungen davon

Info

Publication number
EP1965872A2
EP1965872A2 EP06842054A EP06842054A EP1965872A2 EP 1965872 A2 EP1965872 A2 EP 1965872A2 EP 06842054 A EP06842054 A EP 06842054A EP 06842054 A EP06842054 A EP 06842054A EP 1965872 A2 EP1965872 A2 EP 1965872A2
Authority
EP
European Patent Office
Prior art keywords
composition according
acne
strontium
salts
radical
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Withdrawn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
EP06842054A
Other languages
English (en)
French (fr)
Inventor
Laurent Fredon
Claire Mallard
Eve Ferrara
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
Application filed by Galderma Research and Development SNC filed Critical Galderma Research and Development SNC
Publication of EP1965872A2 publication Critical patent/EP1965872A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61P17/10—Anti-acne agents
    • 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
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/008—Preparations for oily hair
    • 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
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant

Definitions

  • the present invention relates to compositions for topical application, and their uses as cosmetic or pharmaceutical products, said compositions being intended, in particular, for the treatment of acne.
  • Acne is a common multifactorial pathology that reaches skin rich in sebaceous glands (face, scapular region, arms and intertriginous regions). It is the most common dermatitis. The following five pathogenic factors play a determining role in the constitution of acne:
  • acne conglobata keloid acne
  • drug acne recurrent acne
  • acne necrotic acne necrotic
  • acne neonatorum premenstrual acne
  • acne rosacea senile acne
  • solar acne and acne vulgaris.
  • Acne vulgaris also called polymorphous juvenile acne, is the most common. It comprises four stages:
  • Stage 1 corresponds to comedonal acne characterized by a large number of open and / or closed comedones and microcysts.
  • Stage 2 or papulopustular acne
  • Stage 3 or papulocomedonian acne, is more serious and extends to the back, thorax and shoulders. It is accompanied by a larger number of scars.
  • Stage 4 or nodulocystic acne, is accompanied by numerous scars. It presents nodules as well as voluminous pustules violaceous and painful.
  • the different forms of acne described above can be treated with active agents such as anti-seborrhoeic agents and anti-infectious agents, for example benzoyl peroxide (in particular the product Eclaran® marketed by the company Pierre Fabre), with retinoids such as that tretinoin (in particular Retacnyl® product marketed by Galderma) or isotretinoin (Roaccutane® product marketed by Roche Laboratories), or by naphthoic acid derivatives.
  • active agents such as anti-seborrhoeic agents and anti-infectious agents, for example benzoyl peroxide (in particular the product Eclaran® marketed by the company Pierre Fabre), with retinoids such as that tretinoin (in particular Retacnyl® product marketed by Galderma) or isotretinoin (Roaccutane® product marketed by Roche Laboratories), or by naphthoic acid derivatives.
  • active agents such as anti
  • naphthoic acid derivatives such as in particular 6- [3- (1-adamantyl) -4-methoxyphenyl] -2-naphthoic acid), commonly known as adapalene (Differine® product marketed by Galderma), are widely described and recognized as active ingredients as effective as tretinoin for the treatment of acne.
  • Adapalene in particular has a proven efficacy; however, it would be beneficial and useful if its topical tolerance, although superior to that of its competitors in the same chemical class (tretinoin, tazarotene), be improved.
  • adapalene with certain specific anti-irritant compounds can significantly improve the tolerance of this retinoid, and thus overcome the problem of irritation. Indeed, as shown in Example 2, some anti-irritants can reduce the edema caused by adapalene up to 40%.
  • the subject of the present invention is therefore a composition, in particular pharmaceutical, and preferably dermatological, intended in particular for a topical application, comprising, in a physiologically acceptable medium, at least one retinoid compound, preferably chosen from naphthoic acid derivatives of Formula (I) below, their salts and esters, and at least one anti-irritant compound selected from allantoin, EDTA, divalent strontium salts, divalent zinc salts, monovalent sodium salts, and derivatives thereof hydrated.
  • said composition does not include any depigmenting agent.
  • said composition does not comprise any depigmenting agent distinct from the retinoid compound, in particular adapalene.
  • physiologically acceptable medium is meant a medium compatible with the skin, mucous membranes and / or integuments.
  • the retinoid compound according to the invention may be chosen from retinoic acid while trans (or tretinoin), isotretinoin or even motretinide.
  • the retinoid compound according to the invention is preferably chosen from the naphthoic acid derivatives of formula (I), their salts and esters:
  • R represents a hydrogen atom, a hydroxyl radical, a branched or unbranched alkyl radical having from 1 to 4 carbon atoms, an alkoxy radical having 1 to 10 carbon atoms or a substituted or unsubstituted cycloaliphatic radical.
  • linear or branched alkyl radical having from 1 to 4 carbon atoms is meant preferably the methyl, ethyl, propyl and butyl radicals.
  • alkoxy radical having from 1 to 10 carbon atoms is preferably meant methoxy, ethoxy, propoxy, butoxy, hexyloxy and decyloxy radicals.
  • cycloaliphatic radical preferably means mono or polycyclic radicals such as the 1-methylcyclohexyl radical or the 1-adamantyl radical.
  • salts of naphthoic acid derivatives is meant salts formed with a pharmaceutically acceptable base, in particular a mineral base such as sodium hydroxide, potassium hydroxide and aqueous ammonia or an organic base such as lysine, arginine, N -methyl-glucamine, but also the salts formed with fatty amines such as dioctylamine, aminomethyl propanol and stearylamine.
  • a pharmaceutically acceptable base such as sodium hydroxide, potassium hydroxide and aqueous ammonia
  • organic base such as lysine, arginine, N -methyl-glucamine
  • fatty amines such as dioctylamine, aminomethyl propanol and stearylamine.
  • esters of naphthoic acid derivatives is meant esters formed with pharmaceutically acceptable alcohols.
  • 6- [3- (1-adamantyl) -4-methoxyphenyl] -2-naphthoic acid (adapalene) will be chosen.
  • 6- [3- (1-adamantyl) -4-hydroxyphenyl] -2-naphthoic acid 6- [3- (1-adamantyl) -4-decyloxyphenyl] -2-naphthoic acid or acid 6- [3- (1-adamantyl) -4-hexyloxyphenyl] -2-naphthoic acid.
  • the retinoid compound which can be used according to the invention is chosen from adapalene (6- [3- (1 -adamantyl) -4-methoxyphenyl] -2-naphthoic acid), its salts and its esters.
  • adapalene salts in particular salts formed with a pharmaceutically acceptable base, in particular mineral bases such as sodium hydroxide, potash and ammonia or organic bases such as lysine, arginine,
  • Adapalene salts are also understood to mean salts formed with fatty amines such as dioctylamine, aminomethylpropanol and stearylamine.
  • the retinoid compound is adapalene.
  • the anti-irritants that can be used according to the present invention are chosen from allantoin, EDTA, divalent strontium salts, divalent zinc salts, monovalent sodium salts, and their hydrated derivatives.
  • the use of these specific anti-irritants reduces the irritation caused by retinoids, including adapalene.
  • divalent salts of strontium is meant in particular strontium nitrate, strontium chloride, strontium sulphide, strontium carbonate and strontium bromide.
  • the divalent salts of strontium are strontium nitrate and strontium chloride hexahydrate.
  • divalent salts of zinc is meant in particular zinc sulphate, zinc chloride, zinc carbonate and zinc citrate.
  • the divalent zinc salt is zinc sulfate.
  • Monovalent sodium salt is preferably sodium cholate.
  • hydrated derivatives in particular the anti-irritant compounds mentioned above hydrated by one or more water molecules.
  • the hydrated derivatives are strontium chloride hexahydrate or strontium bromide hexahydrate.
  • the anti-irritant compounds are selected from strontium nitrate, allantoin, zinc sulfate, sodium cholate, strontium chloride hexahydrate, and EDTA.
  • the anti-irritant is allantoin or strontium nitrate.
  • the concentration of retinoid compound is between 0.001% and 10%, preferably between 0.01% and 5% and, more preferably, between 0.05% and 2% by weight of the total weight of the composition.
  • the retinoid compound concentration is 0.1%.
  • the concentration of retinoid compound is preferably 0.3%.
  • the concentration of anti-irritant compound is between 0.01% and 10%, preferably between 0.1% and 7%.
  • compositions according to the present invention may be in any of the galenical forms normally used for topical application, especially in the form of aqueous, aqueous-alcoholic or oily dispersions, lotion-type dispersions, aqueous, anhydrous or lipophilic gels, liquid or semi-liquid consistency of the milk type, obtained by dispersion of a fatty phase in an aqueous phase (O / W) or conversely (W / O), or suspensions or emulsions of soft, semi-liquid or solid consistency cream type, gel-cream, mousse or ointment or microemulsions, micro capsules, micro particles or vesicular dispersions of ionic and / or nonionic type, or in the form of sprays.
  • aqueous, aqueous-alcoholic or oily dispersions lotion-type dispersions, aqueous, anhydrous or lipophilic gels, liquid or semi-liquid consistency of the milk type, obtained by dispersion of a fatty phase in an
  • the compositions are in the form of a gel.
  • Those skilled in the art will take care to choose the excipients constituting the compositions according to the invention as a function of the desired dosage form and so that the advantageous properties of the composition according to the invention are respected.
  • composition according to the invention may furthermore in particular comprise one or more of the following ingredients: a) one or more gelling agents or suspending agents, b) one or more chelating agents distinct from EDTA, c) one or more wetting agents , d) one or more preservatives.
  • gelling agents or suspending agents that can be used in the compositions according to the invention
  • hydroxyethylcellulose sold in particular under the name Natrosol HHX 250®.
  • chelating agents include diethylene triamine pentaacetic acid (DTPA), ethylene diamine di (O-hydroxyphenyl acetic acid) (EDDHA) and hydroxy-2-ethylene acid.
  • DTPA diethylene triamine pentaacetic acid
  • EDDHA ethylene diamine di (O-hydroxyphenyl acetic acid)
  • HEDTA triacetic diamine
  • EDDHMA ethyldiamine-di (O-hydroxy-p-methyl phenyl) acetic acid
  • EEDCHA ethylene diamine-di (5-carboxy-2-hydroxyphenyl) acetic acid
  • wetting agents whose function is to reduce the surface tension and to allow a greater spreading of the liquid
  • compounds such as propylene glycol, dipropylene glycol and propylene glycol dipelargonate. , lauroglycol and ethoxydiglycol, alone or in admixture.
  • emulsifiers such as the Tween 80, Glyceryl Monostearate & POE Stearate type sold under the name Arlacel 165FL® by the company Uniquema, Polyoxyethylene (21) Stearyl Ether sold under the name Brij721 ® by Uniquema or synperonics with Synperonic PE / L62 (Poloxamer 182) or Synperonic PE / L44 (Poloxamer 124).
  • a preferred wetting agent mention may be made of propylene glycol, Synperonic PE / L62 (Poloxamer 182) or Synperonic PE / L44 (Poloxamer 124).
  • preserving agents mention may be made, by way of non-limiting examples, of benzoic acid and its derivatives with benzyl alcohol, benzalkonium chloride, sodium benzoate, bronopol, chlorhexidine, chlorocresol and its derivatives, ethyl alcohol, phenethyl alcohol, phenoxyethanol, potassium sorbate, diazolidinyl urea, parabens such as propyl paraben or methyl paraben, alone or in mixtures.
  • composition according to the invention may also comprise one or more emulsifiers.
  • the surfactant 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.
  • Emulsifiers Ionic or nonionic agents thus stabilize the oil / water emulsions by adsorbing at the interface and forming lamellar layers of liquid crystals.
  • emulsifiers As preferred emulsifiers, mention may be made of the emulsifiers previously mentioned for their wetting agent property or lipophilic emulsifiers of the Glucate SS and Glucamate SSE type.
  • compositions of the invention may furthermore comprise any additive usually used in the cosmetic or pharmaceutical field, such as neutralizers, sunscreens, antioxidants, fillers, electrolytes, dyes, conventional or inorganic or organic bases or acids. , 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, penetrating agents, or a mixture of these.
  • any additive usually used in the cosmetic or pharmaceutical field such as neutralizers, sunscreens, antioxidants, fillers, electrolytes, dyes, conventional or inorganic or organic bases or acids.
  • 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.
  • the present invention also relates to the composition as described above as a medicament.
  • the invention relates to the use of a composition as described above for the preparation of a medicament for the treatment and / or prevention of dermatological disorders related to a keratinization disorder relating to differentiation. and on cell proliferation, especially to treat vulgar, comedonal, papulopustular, papulocomedonous, nodulocystic acne, conglobata acne, keloid neck acne, relapsing acne acne, necrotic acne, acne neonatorum, occupational acne, rosacea, senile acnes, solar acnes and medicated acnes.
  • the invention relates to the use of a composition as described above for the preparation of a medicament for preventing and / or treating acne vulgaris.
  • compositions according to the invention are administered topically.
  • the invention also relates to the cosmetic use of a composition according to the invention for the treatment of acne-prone skin, to combat the oily appearance of the skin or hair.
  • the anti-irritants used are formulated unless otherwise indicated in an ethanol / water vehicle (50:50) at the concentrations indicated in the table below. The latter also indicates, for each anti-irritant, the group treated in Example 2.
  • Groups 4 and 6 are used as negative controls in the following studies. Indeed, as shown by the following studies, although known as anti-irritants, the compounds used in these two groups (enoxolone and disodium potassium salt of beta-glycyrrhizic acid) have no effect on the irritation due to retinoids.
  • the present study aims to compare the irritancy of a reference gel with 0.1% of adapalene when this treatment is preceded or not by treatment with an anti-irritant.
  • the treatment consists of a daily topical application (20 ⁇ l) of anti-irritant formulated in a hydro-alcoholic vehicle (50% ethanol and 50% water by volume) on the inside of the right mouse ear.
  • a hydro-alcoholic vehicle 50% ethanol and 50% water by volume
  • BALB / c divided into fifteen groups (female mice approximately 9 weeks old), followed by topical application (20 ⁇ l) of Differin® gel (0.1% reference gel of adapalene), one application of each formulation per day for 6 days.
  • the products to be tested are: Group 1: Untreated (controls) Group 2: Differin® gel (reference gel)
  • Group 6 Disodium potassium salt of beta-glycyrrhizic acid and then Différine® gel
  • Group 7 Sodium chololeate then Différine® gel
  • Group 8 Strontium nitrate then Différine® gel
  • the evaluation is done by measurements of the thickness of the ear using the Oditest and by clinical observation of the animals from the 2nd to the 19th day.
  • FIG. 1 represents the kinetics of the average thickness of the ears of mice between the 2nd and 19th days for groups 1 to 3 (references) and 4 to 6.
  • FIG. 2 represents the kinetics of the mean thickness of the mouse ears between the 2nd and 19th days for groups 1 to 3 (references) and 7 to 9.
  • Strontium nitrate and allantoin surprisingly decrease the irritation due to Differer® gel, in proportions of 37% and 40%, respectively.
  • FIG. 3 represents the kinetics of the mean thickness of the mouse ears between the 2nd and 19th days for groups 1 to 3 (references) and 10 to 13. These kinetics, very similar for groups 10 to 13, show that strontium chloride hexahydrate and EDTA reduce the irritation due to Differer® gel by at least 10%.
  • the anti-irritants tested enoxolone and sodium potassium disodium beta- glycyrrhizic have no effect on the irritation caused by Differin gel;
  • the anti-irritants tested zinc sulphate, sodium cholate, strontium chloride hexahydrate and EDTA reduce the edema by 25%, 9%, 20% and 10% respectively; Strontium nitrate and allantoin anti-irritants significantly lessen (at least 37%) the edema.
  • the purpose of this study is to compare the comedolytic activity of Différine® gel (reference gel with 0.1% of adapalene) when this treatment is preceded or not by treatment with an anti-irritant.
  • the treatment consists of a daily topical application of a hydro-alcoholic vehicle (ethanol / water 50:50) comprising an anti-irritant (strontium nitrate or allantoin), followed 30 minutes later by an application of Différine® gel, on the back of mouse RHINO FVB / N RJ-hr rh (Rhino) for 18 days.
  • a hydro-alcoholic vehicle ethanol / water 50:50
  • an anti-irritant serum nitrate or allantoin
  • the products to be tested are: Group 1: Differin® gel alone
  • Example 4 ⁇ el Formulations Comprising Adapalene at 0.1% and Antiirritants
  • Example 5 Tolerability Study of the Formulations of Example 4
  • Example 2 A tolerance study is conducted according to the protocol of Example 2 with the formulations of Example 4. However, it is here, unlike Example 2, an undissociated treatment, since adapalene and the anti-irritant are present in the same formulation.
  • Differin® Gel 0.1% increases the area under the curve by 45% compared to the placebo gel.
  • Anti-irritant formulations increase the area under the curve compared to the placebo gel in the following order: Formula A> Formula B.
  • formula B is less irritating by 20%.
  • Strontium nitrate appears to be the most effective anti-irritant.
  • Allantoin (Formula A) formed in a gel may be of limited effectiveness in reducing the irritation due to adapalene.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
EP06842054A 2005-12-15 2006-11-28 Zusammensetzungen mit mindestens einer retinoid-verbindung und mindestens einer reizhemmenden verbindung sowie anwendungen davon Withdrawn EP1965872A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0512759A FR2894820B1 (fr) 2005-12-15 2005-12-15 Compositions comprenant au moins un compose retinoide et au moins un compose anti-irritant et leurs utilisations
PCT/FR2006/051243 WO2007071861A2 (fr) 2005-12-15 2006-11-28 Compositions comprenant au moins un compose retinoide et au moins un compose anti-irritant et leurs utilisations

Publications (1)

Publication Number Publication Date
EP1965872A2 true EP1965872A2 (de) 2008-09-10

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EP06842054A Withdrawn EP1965872A2 (de) 2005-12-15 2006-11-28 Zusammensetzungen mit mindestens einer retinoid-verbindung und mindestens einer reizhemmenden verbindung sowie anwendungen davon

Country Status (5)

Country Link
US (1) US20090098219A1 (de)
EP (1) EP1965872A2 (de)
CA (1) CA2632911A1 (de)
FR (1) FR2894820B1 (de)
WO (1) WO2007071861A2 (de)

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Publication number Priority date Publication date Assignee Title
US20140135372A1 (en) 2010-02-02 2014-05-15 Elliott Farber Compositions and methods of treatment of inflammatory skin conditions using allantoin
WO2013178749A1 (fr) 2012-06-01 2013-12-05 Galderma Research & Development Nanocapsules lipidiques comprenant un rétinoide, nanodispersion et composition les contenant, leur procédé de préparation et leur utilisation en dermatologie
FR2991174B1 (fr) 2012-06-01 2014-12-26 Galderma Res & Dev Composition dermatologique comprenant des oleosomes et des retinoides, son procede de preparation et son utilisation
CN103099775B (zh) * 2012-10-08 2014-12-31 天津金耀集团有限公司 阿达帕林凝胶
US20160338997A1 (en) * 2013-12-27 2016-11-24 Scioderm, Inc. Keloid reduction using topical allantoin
JP7299766B2 (ja) * 2018-06-16 2023-06-28 ロート製薬株式会社 外用組成物

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US5804203A (en) * 1994-12-21 1998-09-08 Cosmederm Technologies Topical product formulations containing strontium for reducing skin irritation
US6048902A (en) * 1999-02-12 2000-04-11 Lebwohl; Mark G. Short contact treatment of psoriasis with topical retinoids
US7268148B2 (en) * 1999-05-20 2007-09-11 Regents Of The University Of Michigan Compositions and methods for use against acne-induced inflammation and dermal matrix-degrading enzymes
GB9913408D0 (en) * 1999-06-10 1999-08-11 Albright & Wilson Uk Ltd Personal care formulations
US6583184B1 (en) * 2000-11-27 2003-06-24 Avon Products, Inc. Compositions having comfrey and methods for reducing retinoid-induced skin irritation
US6551605B2 (en) * 2001-04-06 2003-04-22 Haarmann & Reimer Diesters or polyesters of naphthalene dicarboxylic acid as solubilizer/stabilizer for retinoids
ATE366566T1 (de) * 2002-09-05 2007-08-15 Galderma Res & Dev Zusammensetzung zur depigmentierung der haut, die adapalen und mindestens ein depigmentierungsmittel enthält
FR2871377B1 (fr) * 2004-06-11 2007-08-24 Galderma Res & Dev Gel depigmentant hydroalcoolique comprenant du mequinol et de l'adapalene
US20060128808A1 (en) * 2004-10-20 2006-06-15 Galderma Research & Development, S.N.C. Method of using adapalene in acne maintenance therapy
FR2916966B1 (fr) * 2007-06-11 2011-01-14 Galderma Res & Dev Compositions comprenant au moins un compose retinoide, un compose anti-irritant et du peroxyde de benzoyle, et leurs utilisations

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Title
See references of WO2007071861A2 *

Also Published As

Publication number Publication date
US20090098219A1 (en) 2009-04-16
WO2007071861A8 (fr) 2008-09-04
WO2007071861A2 (fr) 2007-06-28
CA2632911A1 (fr) 2007-06-28
FR2894820A1 (fr) 2007-06-22
FR2894820B1 (fr) 2008-02-29
WO2007071861A3 (fr) 2007-10-04

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