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EP2459172A1 - Combinaison du dapsone avec l'adapalene - Google Patents

Combinaison du dapsone avec l'adapalene

Info

Publication number
EP2459172A1
EP2459172A1 EP10744770A EP10744770A EP2459172A1 EP 2459172 A1 EP2459172 A1 EP 2459172A1 EP 10744770 A EP10744770 A EP 10744770A EP 10744770 A EP10744770 A EP 10744770A EP 2459172 A1 EP2459172 A1 EP 2459172A1
Authority
EP
European Patent Office
Prior art keywords
composition
adapalene
dapsone
treatment
inflammatory
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Withdrawn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
EP10744770A
Other languages
German (de)
English (en)
Inventor
Gurpreet Ahluwalia
Kevin S. Warner
Haigang Chen
Meidong Yang
Frederick C. BEDDINGFIELD
Jeffrey R. EHRHARDT
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.)
Allergan Inc
Original Assignee
Allergan Inc
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 Allergan Inc filed Critical Allergan Inc
Publication of EP2459172A1 publication Critical patent/EP2459172A1/fr
Withdrawn legal-status Critical Current

Links

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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • 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
    • 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

Definitions

  • the present invention is directed to compositions and methods for the treatment of acne vulgaris and other dermato logical conditions.
  • Acne is the most common skin disease that affects a large number of adolescents and young adults after they reach puberty. Though not a life threatening disease, it has serious psychological impact on the patient. Chronic inflammatory acne can also result in permanent scarring of the face.
  • acne is a multifactorial condition
  • the marketed products work on one or more of the underlying factors contributing to acne for its treatment.
  • OTC over-the-counter
  • products include antibiotics (topical and systemic), benzoyl peroxide, retinoids (topical and systemic), dapsone, and a number of other compounds.
  • the anti-acne molecule dapsone is marketed as a commercial product Aczone®.
  • Aczone® is a 5% dapsone gel with a gritty texture due to insoluble particles of dapsone drugs.
  • the insolubility of dapsone limits the bioavilability of dapsone upon application and its absorption through the skin and is therefore administered twice daily.
  • dapsone exhibits an anti-inflammatory activity which provides a unique mechanism of action for this molecule in treatment of inflammatory acne lesions.
  • a complex combination of inflammatory pathways produce the clinical inflammation observed in acne. It is known that neutrophils significantly contribute to inflammatory acne. Dapsone is known to suppress neutrophil recruitment & local production of toxic products there by inhibiting neutrophil chemotaxis and reducing generation of oxygen free radicals. It further inhibits release of lysosomal enzymes and reduces release and bocks inflammatory effects of prostaglandins & leukotrienes. These effects results in reduction of inflammatory acne lesions. In addition to its anti-inflammatory activity, dapsone is also effective against P. acnes. MIC90 against P. acnes is 8 ⁇ g/ml. Adapalene is a third generation retinoid, which are compounds related to Vitamin
  • Adapalene is known to moderate inflammatory processes but its mechanism of action is also not entirely understood. Adapalene products are sold with the concentrations of 0.1% and 0.3% w/v concentrations for gels and 0.1% w/v concentration for cream. Adapalene acts on retinoid receptors and appears to be a modifier of cellular differentiation, keratinization and inflammatory processes which are involved in the pathology of acne vulgaris. Absorption of adapalene from either 0.1% or 0.3% gel or cream is low. In one pharmacokinetic study, 16 patients suffering from acne vulgaris received 0.3% adapalene gel applied to the face, chest and back which is approximately a dosage of 2 mg/cm2.
  • a combination acne product would provide the benefit of enhanced efficacy compared to the products containing single active agent by taking advantage of the synergistic mechanism of action of the active agents for treatment of acne.
  • the present invention is directed to acne products with at least two active compounds and in particular are directed to dapsone and adapalene combination formulations for the use in the treatment of dermatological conditions such as acne vulgaris, rosacea, atopic dermatitis, treatment of chronic wounds, bed sores, keratosis piralis, psoriasis, cosmetic improvement of surgical and acne scars, sebaceous cysts, inflammatory dermatoses, post inflammatory hyperpigmentation, eczema, xerosis, pruritis, lichen planus, nodular prurigo, eczema, and miliaria and other dermatological conditions.
  • a dermatological composition comprising dapsone, adapalene, and water.
  • composition comprises 5% w/w dapsone and 0.1% or 0.3% w/w adapalene and is used for the treatment of acne vulgaris.
  • compositions of paragraph 1 wherein the composition is a gel.
  • compositions of paragraphs 1 and 4 wherein the composition is 0.5% w/w dapsone, 0.1% w/w adapalene, 1.5% w/w benzyl alcohol, transcutol, 5 - 25% w/w PEG 400, 0.01% w/w EDTA, and 0.03% w/w citric acid. .
  • compositions of paragraphs 1 - 5 further comprising carbopol 980 at 0.5 - 2% w/w.
  • compositions of paragraphs 1 - 7 further comprising methyl paraben.
  • compositions of paragraphs 1 - 8 further comprising lactic acid.
  • compositions of paragraphs 1 - 9 further comprising glycerin.
  • composition of paragraph 5 further comprising dimethyl isosorbide in 5 - 15% w/w.
  • compositions of paragraphs 1 - 15 wherein the composition is in the form of one selected from the group consisting of a gel, emulsion, cream, liquid, paste, lotion, nanoemulsion, microemulsion, reverse emulsion and liposomal cream.
  • compositions of paragraphs 1- 16 wherein the composition may be used for treatment of one selected from the group consisting of acne vulgaris, rosacea, atopic dermatitis, treatment of chronic wounds, bed sores, keratosis piralis, sebaceous cysts, inflammatory dermatoses, post inflammatory hyperpigmentation, eczema, xerosis, pruritis, lichen planus, nodular prurigo, dermatitis, eczema, and miliaria and other dermatological conditions.
  • Fig. 1 is directed to dapsone and adapalene formulations for the treatment of
  • Fig. 2 is directed to variations of formulations for the treatment of dermatological conditions of Formula 1 of Figure 1;
  • Fig. 3 A is directed to variations of formulations for the treatment of dermatological conditions of Formula 2 of Figure 1;
  • Fig. 3B is directed to variations of formulations for the treatment of dermatological conditions of Formula 2 of Figure 1;
  • Fig. 3C is directed to variations of formulations for the treatment of dermatological conditions of Formula 2.1 of Figure 1;
  • Fig. 3D is directed to variations of formulations for the treatment of dermatological conditions of Formula 2.1 of Figure 1;
  • Fig. 4A is directed to variations of formulations for the treatment of dermatological conditions of Formula 4 of Figure 1;
  • Fig. 4B is directed to variations of formulations for the treatment of dermatological conditions of Formula 4 of Figure 1;
  • Fig. 4C is directed to variations of formulations for the treatment of dermatological conditions of Formula 4 of Figure 1;
  • Fig. 4D is directed to variations of formulations for the treatment of dermatological conditions of Formula 4 of Figure 1;
  • Fig. 5 is directed to dapsone and adapalene formulations for the treatment of
  • the present invention is directed to topical compositions for treatment of dermatological conditions which contain at least two active ingredients, one of these being dapsone and the other(s) selected from the list below for an effective treatment of acne and other dermatological conditions such as rosacea.
  • Suitable compounds that can be combined with dapsone (2 - 10% w/w) include:
  • Benzoyl peroxide 2.5 - 10% w/w
  • other antimicrobial actives that are effective against P. acnes.
  • Agents that inhibit comedogenesis by reducing pilosebaceous canal obstruction or have kerato lytic properties such as:
  • Salicylic acid 0.5 - 3% w/w
  • Azelaic acid (up to 20% w/w);
  • tretinoin or trans retinoic acid (0.02 - 0.1 % w/w); ii. Tazarotene (0.05 - 0.1 % w/w);
  • Adapalene (0.1 - 0.3% w/w);
  • One aspect of the present invention is a combination adapalene/dapsone topical formulation combining the two actives into one formulation.
  • the novelty of this invention is in part attributable to the use of additional excipients (solubilizers) in combination with diethylene glycol monoethyl ether ("DGME”) in order to solubilize dapsone. Addition of cosolvents has enabled the complete dissolution of dapsone in the formulation and an increase in the solubility of adapalene (adapalene is not completely solubilized in these formulations).
  • the increased concentration of dissolved dapsone and adapalene versus the marketed product comparators administered concurrently will increase the rate of skin penetration of both drugs into and through the skin
  • Topical dosage forms of the present invention include, but are not limited to solutions, gels, creams, ointments, foams, emulsions, films, and facial/skin peels.
  • the present invention is directed to topical dapsone and adapalene formulations which are formulated to optimize the dermal delivery profile of adapalene and dapsone to effectively treat acne and other dermatological conditions and improve the efficiency of
  • compositions of the present invention of 5% w/w dapsone and 0.1% w/w and 0.3% w/w adapalene formulations include but are not limited to: Table 2A: Adapalene / Dapsone Topical Formulations
  • formulations of the present invention can be made as follows based on the excipients:
  • adapalene/dapsone gels were prepared as follows:
  • step b Add water, EDTA, and citric acid to mixture in step a. Mix until dissolved; c. Add adapalene to mixture in step b; d. While continuing to mix, slowly add hydroxyethyl cellulose to mixture in step c avoid clumping. Mix vigorously at room temperature until a uniform lump-free dispersion is achieved; and,
  • adapalene/dapsone gels were prepared as follows:
  • step b Add water, EDTA, and citric acid to mixture in step a. Mix until dissolved.
  • c Add adapalene to mixture in step b;
  • step c While continuing to mix, slowly add hydroxyethyl cellulose to mixture in step c avoid clumping. Mix vigorously at room temperature until a uniform lump-free dispersion is achieved; and,
  • adapalene/dapsone gels were prepared as follows:
  • step b Add water, EDTA, and citric acid to mixture in step a. Mix until dissolved; c. Add adapalene to mixture in step b;
  • adapalene/dapsone gels were prepared as follows: a. Weigh the Transcutol into a kettle. Add the dapsone, propylene glycol, polyethylene glycol 400, benzyl alcohol. Stir with propeller mixer at room temperature. Mix until dissolved;
  • step b Add water, EDTA, and citric acid to mixture in step a. Mix until dissolved; c. Add adapalene to mixture in step b;
  • adapalene/dapsone gels were prepared as follows:
  • step b Add water, EDTA, and citric acid to mixture in step a. Mix until dissolved; c. Add adapalene to mixture in step b;
  • adapalene/dapsone gels were prepared as follows:
  • step b Add water, EDTA, and citric acid to mixture in step a. Mix until dissolved; c. Add adapalene to mixture in step b;
  • step c While continuing to mix, slowly add hydroxy ethyl cellulose to mixture in step c avoid clumping. Mix vigorously at room temperature until a uniform lump-free dispersion is achieved; and, e. While mixing add sufficient sodium hydroxide to achieve a pH of 5.3 to 5.7. Mix until uniform.
  • the most effective dapsone and adapalene composition is selected based on clinical studies. For example, a clinical study is conducted by forming two treatment groups, one with daily application of a selected dapsone and adapalene formulation, and twice daily topical application of the same selected dapsone and adapalene formulation to the acne area of the skin for a period of 12 weeks. Two control groups are formed with application once and twice daily of a vehicle consisting of the same excipients but no active ingredients. The patient's inflammatory and non-inflammatory acne lesion counts should be recorded at baseline before initiation of treatment and then at select intervals throughout the study. The reduction in total, non-inflammatory or inflammatory lesions counts provides determination of the efficacy of the formulations.
  • the established Global Acne Assessment Score should be used to assess efficacy of the product.
  • the tolerability of the product can be determined by assessment of skin dryness, irritation, sensitivity and redness as a result of treatment. A product is considered to have better tolerability if there is less effect on these parameters.
  • a suitable application method is topical cream, gel, lotion, ointment, foam, liquid or a semi solid preparation.
  • a topical preparation may contain additional ingredients to provide aesthetic and moisturizing and anti-inflammatory benefits to the skin.
  • a gel or liquid preparation can be alcohol or aqueous based or a combination of two;
  • a nanoemulsion or microemulsion preparation can be used for enhanced delivery of actives
  • a liposomal cream or lotion preparation can be used for enhanced delivery of actives
  • a foam preparation can be a quick breaking foam with additional emollient components.
  • Topical preparations that result in slow release or controlled release of the active agent can also be used to provide an optimal efficacy and tolerability balance.
  • Active ingredients encapsulated in micro beads or adsorbed on microsponge can be used for control release and in addition solve any incompatibility issues between the formulation ingredients.
  • the application is preferably once a day or more frequent depending on the desired effect.
  • a 17 year old Caucasian male patient suffers acne vulgaris with a combination of inflammatory and non-inflammatory lesions and applies a 0.1% w/w adapalene formulation according to formulation #1 in Fig. 5.
  • the 17 year old male patient applies the 0.1% w/w adapalene composition of Formula 1 once daily for 12 weeks. After 12 weeks, the 17 year old male patient experiences a 32% reduction in inflammatory and non-inflammatory lesions.
  • Example #2 Application of 0.3 % w/w adapalene of Formula 1 in Fig. 5
  • a 16 year old Caucasian female patient suffers acne vulgaris with a combination of inflammatory and non-inflammatory lesions and applies a 0.3% w/w adapalene formulation according to formulation #1 in Fig. 5.
  • the 16 year old female patient applies the 0.3% w/w adapalene composition of Formula 1 once daily for 12 weeks. After 12 weeks, the 16 year old female patient experiences a 41% reduction in inflammatory and non-inflammatory lesions.
  • a 23 year old African- American female patient suffers acne vulgaris with a combination of inflammatory and non-inflammatory lesions and applies a 0.1% w/w adapalene formulation according to formulation #2 in Fig. 5.
  • the 23 year old female patient applies the 0.1% w/w adapalene composition of Formula 2 once daily for 12 weeks. After 12 weeks, the 23 year old female patient experiences a 24 % reduction in inflammatory and non-inflammatory lesions.
  • a 19 year old Caucasian female patient suffers acne vulgaris with a combination of inflammatory and non-inflammatory lesions and applies a 0.3% w/w adapalene formulation according to formulation #2 in Fig. 5.
  • the 19 year old female patient applies the 0.3% w/w adapalene composition of Formula 2 once daily for 12 weeks. After 12 weeks, the patient experiences a 248 % reduction in inflammatory and noninflammatory lesions.
  • a n 23 year old Asian female patient suffers acne vulgaris with a combination of inflammatory and non-inflammatory lesions and applies a 0.3% w/w adapalene formulation according to formulation #3 in Fig. 5.
  • the 23 year old patient applies the 0.3% w/w adapalene composition once daily for 12 weeks. After 12 weeks, the patient experiences a 25 % reduction in inflammatory and non-inflammatory lesions.
  • An 18 year old African- American male patient suffers acne vulgaris with a combination of inflammatory and non-inflammatory lesions and applies a 0.1% w/w adapalene formulation according to formulation #3 in Fig. 5.
  • the 18 year old male patient applies the 0.1% w/w adapalene composition once daily for 12 weeks. After 12 weeks, the 18 year old male patient experiences a 29 % reduction in inflammatory and non-inflammatory lesions.
  • a 17 year old Caucasian female patient suffers acne vulgaris with a combination of inflammatory and non-inflammatory lesions and applies a 0.3% w/w adapalene formulation according to formulation #4 in Fig. 5.
  • the 17 year old male patient applies the 0.3% w/w adapalene composition twice daily for 12 weeks. After 12 weeks, the 17 year old male patient experiences a 41 % reduction in inflammatory and non- inflammatory lesions.
  • Example #9 Application of 0.1% w/w adapalene of Formula 5 in Fig. 5
  • a 16 year old Caucasian female patient suffers acne vulgaris with a combination of inflammatory and non-inflammatory lesions and applies a 0.1% w/w adapalene formulation according to formulation #5 in Fig. 5.
  • the 16 year old female patient applies the 0.1% w/w adapalene composition once daily for 12 weeks. After 12 weeks, the patient experiences a 27 % reduction in inflammatory and non-inflammatory lesions.
  • Example #10 Example #9 - Application of 0.3% w/w adapalene of Formula 5 in Fig. 5
  • a 19 year old Caucasian female patient suffers acne vulgaris with a combination of inflammatory and non-inflammatory lesions and applies a 0.3% w/w adapalene formulation according to formulation #5 in Fig. 5.
  • the 19 year old female patient applies the 0.3% w/w adapalene composition twice daily for 12 weeks. After 12 weeks, the patient experiences a 38 % reduction in inflammatory and non-inflammatory lesions.
  • Example #11 Application of 0.1% w/w adapalene of Formula 1 in Fig. 5
  • a 37 year old Caucasian male patient suffers from rosacea and applies a 0.1% w/w adapalene formulation according to formulation #1 in Fig. 5.
  • the 37 year old male patient applies the 0.1% w/w adapalene composition of Formula 1 once daily for 12 weeks. After 12 weeks, the 37 year old male patient experiences a reduction in the symptoms of rosacea.

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  • Pharmacology & Pharmacy (AREA)
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Abstract

L'invention concerne une composition conçue pour une application topique qui contient au moins deux ingrédients actifs, l'un étant du dapsone, l'autre sélectionné dans le groupe constitué de l'adapalène, du tazarotène et du treinion, pour le traitement efficace de l'acné et d'autres états dermatologiques.
EP10744770A 2009-07-30 2010-07-29 Combinaison du dapsone avec l'adapalene Withdrawn EP2459172A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US22990309P 2009-07-30 2009-07-30
PCT/US2010/043671 WO2011014627A1 (fr) 2009-07-30 2010-07-29 Combinaison du dapsone avec l'adapalene

Publications (1)

Publication Number Publication Date
EP2459172A1 true EP2459172A1 (fr) 2012-06-06

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EP10744770A Withdrawn EP2459172A1 (fr) 2009-07-30 2010-07-29 Combinaison du dapsone avec l'adapalene

Country Status (6)

Country Link
EP (1) EP2459172A1 (fr)
JP (1) JP2013500984A (fr)
AU (1) AU2010278915A1 (fr)
CA (1) CA2769640A1 (fr)
RU (1) RU2012104572A (fr)
WO (1) WO2011014627A1 (fr)

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US20110117182A1 (en) * 2009-07-30 2011-05-19 Allergan, Inc. Combination of dapsone with other anti-acne agents
WO2011135090A1 (fr) * 2010-04-29 2011-11-03 Galderma Research & Development Méthode de traitement des cicatrices par l'adapalène à 0,3%
CN103491945A (zh) * 2011-03-03 2014-01-01 阿勒根公司 基于硅酮的非水性眼科制剂
WO2013003236A1 (fr) 2011-06-30 2013-01-03 Allergan, Inc. Compositions topiques de rétinoïde et méthodes de traitement d'états cutanés
AU2013348247A1 (en) 2012-11-20 2015-05-21 Allergan, Inc. Topical dapsone and dapsone/adapalene compositions and methods for use thereof
WO2016136925A1 (fr) * 2015-02-27 2016-09-01 マルホ株式会社 Composition pour la peau
JP6508681B2 (ja) * 2016-01-18 2019-05-08 基嗣 田島 ケミカルピーリング剤
KR102662461B1 (ko) * 2017-07-21 2024-04-30 알미랄 엘엘씨 비염증성 병변의 치료
JPWO2019240290A1 (ja) * 2018-06-16 2021-06-24 ロート製薬株式会社 外用組成物
JP7299766B2 (ja) * 2018-06-16 2023-06-28 ロート製薬株式会社 外用組成物
JP2022131565A (ja) * 2021-02-26 2022-09-07 ロート製薬株式会社 水性医薬組成物

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KR20070091613A (ko) * 2004-11-08 2007-09-11 그렌마크 파머수티칼스 엘티디. 항여드름 화합물 및 항생제 화합물을 함유하는 국소적 제약조성물
MXPA06008988A (es) * 2006-08-08 2008-02-07 Fernando Ahumada Ayala Preparaciones topicas antiacne que contienen retinoide (tazaroteno o adapaleno), antibiotico (fosfato de clindamicina) y/o queratolitico (peroxido de bonzoilo en microesponjas).
US20100029781A1 (en) * 2008-06-04 2010-02-04 Morris Jerome A Methods for preparation of anti-acne formulation and compositions prepared thereby

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Title
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Publication number Publication date
WO2011014627A1 (fr) 2011-02-03
CA2769640A1 (fr) 2011-02-03
AU2010278915A1 (en) 2012-03-01
JP2013500984A (ja) 2013-01-10
RU2012104572A (ru) 2013-09-10

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