WO2006111426A1 - Composition d'une solution de type filmogene, comprenant de la vitamine d ou un de ses derives et un corticosteroide, et son utilisation en dermatologie - Google Patents

Composition d'une solution de type filmogene, comprenant de la vitamine d ou un de ses derives et un corticosteroide, et son utilisation en dermatologie Download PDF

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Publication number
WO2006111426A1
WO2006111426A1 PCT/EP2006/004315 EP2006004315W WO2006111426A1 WO 2006111426 A1 WO2006111426 A1 WO 2006111426A1 EP 2006004315 W EP2006004315 W EP 2006004315W WO 2006111426 A1 WO2006111426 A1 WO 2006111426A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
composition
vitamin
corticosteroid
betamethasone
Prior art date
Application number
PCT/EP2006/004315
Other languages
English (en)
Inventor
Claire Mallard
Laurent Fredon
Original Assignee
Galderma S.A.
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
Priority claimed from FR0503913A external-priority patent/FR2884419B1/fr
Application filed by Galderma S.A. filed Critical Galderma S.A.
Priority to EP06753522A priority Critical patent/EP1874320A1/fr
Publication of WO2006111426A1 publication Critical patent/WO2006111426A1/fr
Priority to US11/976,066 priority patent/US20080118453A1/en
Priority to US12/983,608 priority patent/US20110300086A1/en

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Classifications

    • 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
    • A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
    • 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
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • 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
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings

Definitions

  • composition of film-forming solution type comprising vitamin D or a derivative thereof and a corticosteroid, and use thereof in dermatology
  • the invention relates to a novel composition of film- forming solution type, intended for application to the nails, comprising two solubilized active agents which are: vitamin D or a derivative thereof, preferably calcitriol, and a corticosteroid, preferably clobetasol 17-propionate, and also to the use thereof in dermatology in the treatment of nail psoriasis.
  • two solubilized active agents which are: vitamin D or a derivative thereof, preferably calcitriol, and a corticosteroid, preferably clobetasol 17-propionate
  • Psoriasis is a chronic inflammatory disease of the skin which affects approximately 5% of the French population. This disease manifests itself through lesions, giving rise to quite distinct forms of psoriasis.
  • nail psoriasis involves approximately half the individuals suffering from the disease.
  • the nails of the hands are affected more than those of the feet.
  • the nail which grows in an accelerated manner, is then subjected to certain alterations - due to keratinization problems - depending on the location of the psoriasis. It sometimes exhibits at its surface small depressions which give it a thimble-like appearance. Sometimes, salmon-coloured marks appear, or even a discoloration.
  • the nail can also undergo thickening which can detach it from its bed. Finally, it sometimes exhibits transverse or longitudinal striations.
  • the inflammation can also extend under the nail: in this case, the lesions are not in contact with the air and heal with difficulty.
  • Antifungal treatments can also be prescribed in the case of secondary infection.
  • Vitamin D and derivatives thereof are unstable in aqueous media, and sensitive to acidic pHs, whereas corticosteroids, and more particularly clobetasol 17-propionate, are themselves sensitive to basic media.
  • compositions which not only must be physically and chemically stable, but also must make it possible to release the active agent and to promote the penetration thereof over the target zone in order to improve its effectiveness .
  • compositions for the nails comprising vitamin D or a derivative thereof and a corticosteroid, said composition being stable and well tolerated.
  • the present invention consists in providing a novel formulation, of film-forming solution type, comprising vitamin D or a derivative thereof, preferably calcitriol, combined with a corticosteroid, preferably clobetasol 17-propionate.
  • This composition is of use in the treatment of nail psoriasis.
  • the solution form allows local application of the treatment without systemic exposure; it is therefore well tolerated. Furthermore, by virtue of its composition, this solution allows a gradual release of the active ingredients.
  • the present invention therefore relates to a composition
  • a composition comprising, in a physiologically acceptable medium, as pharmaceutical active agents, vitamin D or a derivative thereof and a corticosteroid, characterized in that said composition is a film-forming solution.
  • This solution is preferably a nail varnish.
  • the present invention preferably relates to a composition
  • a composition comprising, in a physiologically acceptable medium, as pharmaceutical active agents, calcitriol and clobetasol 17-propionate, characterized in that said composition is a film-forming solution, preferably a nail varnish.
  • clobetasol 17-propionate will be referred to as clobetasol propionate.
  • physiologically acceptable medium is intended to mean any medium that is compatible with the skin, the mucous membranes and the integuments.
  • film-forming solution is intended to mean a solution containing at least one film-forming polymer. Such a solution is preferably intended for application to the nails.
  • the film-forming solution according to the invention is a nail varnish.
  • the film-forming solution according to the invention is a nonaqueous solution.
  • nonaqueous solution is intended to mean a solution free of added water.
  • the solution may, however, contain an amount of residual water not exceeding 5% of the total concentration of solvents/cosolvents of the composition.
  • the film-forming solution according to the invention is a nonaqueous nail varnish.
  • composition is therefore for topical use.
  • compositions can also be sprayed with or without propellant gas.
  • composition contains a propellant gas
  • a propellant gas it is chosen from the group consisting of propane, butane, isobutane, dichlorodifluoromethane, dichlorotetra- fluoroethane, octafluorocyclobutane, nitrogen, CO 2 and dimethyl ether, or mixtures thereof.
  • the propellant gas is in liquefied form and its concentration is between 5% and 30% of the total composition.
  • the composition is a film-forming solution, preferably a nail varnish, which comprises, in a physiologically acceptable medium, as pharmaceutical active agents, vitamin D or a derivative thereof and a corticosteroid, which are present in solubilized form.
  • the film-forming solutions as defined above comprise: a) vitamin D or a derivative thereof and a cortico- steroid, which are solubilized, b) an organic solvent/cosolvent mixture, c) and at least one film-forming agent.
  • the film- forming solutions as defined above comprise: a) calcitriol and clobetasol propionate, which are solubilized, b) an organic solvent/cosolvent mixture, c) and at least one film-forming agent.
  • vitamin D is intended to mean the various forms of vitamin D, such as, for example, vitamin Di, D 2 , D 3 or vitamin D 4 .
  • vitamin D derivatives is intended to mean compounds which exhibit biological properties similar to those of vitamin D, in particular vitamin D response element (VDRE) transactivating properties, such as an agonist or antagonist activity with respect to vitamin D receptors.
  • VDRE vitamin D response element
  • These compounds are not generally natural metabolites of vitamin D, but are in particular synthetic compounds comprising the vitamin D backbone with modifications on the side chains and/or comprising modifications in the backbone itself.
  • vitamin D derivatives mention may, by way of nonlimiting example, be made of calcipotriol, 25-hydroxyvitamin D 3 , l ⁇ -hydroxyvitamin D 3 , calcitriol or l ⁇ , 25-dihydroxyvitamin D 3 , l ⁇ , 25, 2 ⁇ -trihydroxy- vitamin D3, l ⁇ , 23, 25-trihydroxyvitamin D3, 24, 25-dihydroxyvitamin D3, l ⁇ , 25-dihydroxyvitamin D2, l ⁇ -hydroxyvitamin D2, l ⁇ , 24-dihydroxyvitamin D2 and l ⁇ ,24-dihydroxyvitamin D3 (or tacalcitol), and mixtures thereof.
  • the vitamin D derivative is calcitriol.
  • the amount of vitamin D or derivatives thereof that can be used according to the invention is between 0.00001% and 0.1% m/m, preferably between 0.0001% and 0.001% m/m, and preferably between 0.0002% and 0.0005% m/m. This amount is preferably equal to 0.0003% m/m.
  • corticosteroids mention may, by way of non- limiting example, be made of clobetasone and esters thereof such as the 17-butyrate, clobetasol and esters thereof such as the 17-propionate, hydrocortisone and esters thereof such as the 17-butyrate, cortisone and esters thereof such as the 21-acetate, prednisolone and esters thereof such as pivalate, miconazole, prednisone, triamcinolone and esters and ethers thereof such as triamcinolone acetonide, methylprednisolone, fluometholone, fluocinolone and esters and ethers thereof such as fluocinolone acetonide, desonite, betamethasone and esters thereof such as the 21-acetate, the 17-adamantoate, the 17-benzoate, the 17-valerate and the 17, 21-di ⁇ ropionate, and dexamethasone, and mixtures
  • corticosteroid derivatives is intended in particular to mean their pharmaceutically acceptable salts with a base, such as the disodium phosphate salts.
  • the corticosteroid is a clobetasol ester such as clobetasol 17-propionate, called clobetasol propionate in the present application.
  • the amount of corticosteroid that can be used according to the invention is between 0.0001% and 0.1% m/m, preferably between 0.001% and 0.05% m/m, and preferably between 0.0002% and 0.0005% m/m. This amount is preferably equal to 0.025% m/m.
  • the composition is a film-forming solution, preferably a nail varnish, which also contains at least one promoter of absorption into the nail.
  • the composition contains two absorption promoters.
  • promoter of absorption into the nail is intended to mean pharmaceutically acceptable chemical compounds capable of increasing the permeability of the nail with respect to the active ingredients, so as to increase the kinetics of penetration of these active ingredients through the nail.
  • the absorption promoters that can be used according to the invention are urea, glycols, such as propylene glycol, butylene glycol, hexylene glycol, ethylene glycol or polyethylene glycols, glycol monoethers, such as the ethylene glycol monoethers sold under the names "Dowanol PM, DPM, TPM, PnB, PPH, DPnB, TPnB, PMA", glycol polyethers such as ethoxydiglycol, propylene glycol dimethyl ether or dipropylene glycol dimethyl ether, dimethyl sulphoxide, amino acids and derivatives thereof such as N-acetyl-L-cysteine, and a mono- or polycarboxylated C 1 to Ci 8 , preferably Ci to C 12 , carboxylic acid and derivatives thereof such as hydroxymonocarboxylic acids, hydroxydicarboxylic acids, or the free acids, and also the lactones, the salts, the esters derived therefrom
  • Ci to C 12 aliphatic carboxylic acids and in particular hydroxyl acids
  • the solution according to the invention may comprise, as aliphatic carboxylic acid, lactic acid or citric acid, preferably lactic acid.
  • the absorption promoters are the pairs urea/lactic acid or urea/N-acetyl-L-cysteine.
  • the urea is used at a concentration of less than 15% by weight of urea relative to the weight of the nonvolatile part of the composition, in particular at a concentration of less than 14% by weight of urea relative to the weight of the non-volatile part of the composition, preferably between 7% and 14%, and more particularly between 9% and 13% by weight of urea relative to the weight of the non-volatile part of the composition;
  • the lactic acid is used in an amount of between 0.01% and 15% m/m, and preferably between 1% and 10%, in particular between 1% and 7%;
  • the N- acetyl-L-cysteine is used in an amount of between 0.5% and 10% m/m, preferably between 1% and 7% m/m.
  • the weight proportion of ethoxydiglycol relative to the total weight of the composition is between 0.01% and 20% m/m, and preferably between 1% and 10%.
  • the solution according to the invention contains a solvent.
  • the solvents and cosolvents can be chosen from the organic solvent family, and are class 3 solvents with a low toxic potential according to the ICH standards (Impurities: Guideline for Residual Solvents, International Conference of Harmonization) , such as ethanol, isopropyl alcohol, acetone, methyl acetate, ethyl acetate, butyl acetate, alkyl methyl sulphoxides, such as dimethyl sulphoxide, 2-propanol, methyl isobutyl ketone, 1-butanol, dichloromethane or N-methyl-2-pyrrolidone, or mixtures thereof.
  • ICH standards Impurities: Guideline for Residual Solvents, International Conference of Harmonization
  • solvents/cosolvents as described above, use will preferably be made of volatile organic solvents/ cosolvents, and more preferably a mixture consisting of ethanol and of at least one cosolvent chosen from ethyl acetate and butyl acetate.
  • the solvents/cosolvents can be used at the preferential concentrations ranging, respectively, from 10% to 90% and from 0% to 30% m/m, and more preferably ranging respectively from 10% to 80% and from 1% to 30% m/m.
  • the vitamin D or derivatives thereof, preferably calcitriol, and the corticosteroid, preferably clobetasol propionate are solubilized in the preferred solvent, i.e. ethanol.
  • the latter is preferably water- insoluble and chosen from: - copolymers of monoalkyl esters of polyvinyl methyl ether and maleic acid, such as the butyl ester of polyvinyl methyl ether and maleic acid copolymer (butyl ester of PVM/MA copolymer) sold under the name Gantrez ES 425 by the company ISP, copolymers of acrylic and methacrylic acid esters with a low content of quaternary ammonium groups derived from acrylic acid, such as the acrylate and ammonium methacrylate copolymer (acrylate/ ammonium methacrylate copolymer) sold under the name Eudragit RL 100 by the company Rohm Pharma, cellulose derivatives, such as the nitrocellulose or the ethylcellulose sold by the company Aqualon, polyurethane derivatives, such as the Avalures sold by the company Noveon.
  • polyvinylpyrrolidones and derivatives such as poly-l-vinyl-2-pyrrolidone, polyvinylpyrrolidone/vinyl acetate copolymer and vinyl- pyrrolidone/dimethylaminoethyl methacrylate copolymer, the copolymer derived from vinylpyrrolidone/acrylic acid and lauryl methacrylate, polysaccharides such as, in particular, chitosans and derivatives, gums such as guar gum, carrageenan gums, karaya gum or xanthan gum, polyvinyl alcohols, polyacrylamides, acrylic/ methacrylic, polymethacrylate/butyl acrylate or acrylic/acrylate copolymers, cyanoacrylic polymers, or polyvinyl methyl ether/maleic anhydride copolymer.
  • polysaccharides such as, in particular, chitosans and derivatives
  • gums such as guar gum
  • the film-forming agent as described above is used at the preferential concentrations ranging from 0.01% to 50% m/m, preferably 5% to 30% m/m.
  • the composition can also contain a plasticizer.
  • the plasticizer is preferably used at concentrations ranging from 0.001% to 10.00% m/m, preferably from 0.5% to 5% m/m.
  • plasticizers use is made, without this list being limiting, of compounds such as phthalates, triacetates or citrates, or mixtures thereof.
  • the plasticizer is preferably triacetin.
  • the film-forming solution according to the invention can also comprise any additive normally used in the cosmetics or pharmaceutical field, such as sequestering agents, wetting agents, adhesion agents, spreading agents, antioxidants, sunscreens, preserving agents, fillers, electrolytes, humectants, pigments, dyes, of usual bases or acids, which may be inorganic or organic, essential oils, cosmetic active agents, moisturizers, vitamins, essential fatty acids, or sphingolipids .
  • any additive normally used in the cosmetics or pharmaceutical field such as sequestering agents, wetting agents, adhesion agents, spreading agents, antioxidants, sunscreens, preserving agents, fillers, electrolytes, humectants, pigments, dyes, of usual bases or acids, which may be inorganic or organic, essential oils, cosmetic active agents, moisturizers, vitamins, essential fatty acids, or sphingolipids .
  • any additive normally used in the cosmetics or pharmaceutical field such as sequestering agents, wetting agents, adhesion agents, spreading agents,
  • the invention also relates to the composition as described above, as a medicament.
  • the invention relates to the use of a composition as defined above, in the manufacture of a medicament for use in the prevention or treatment of nail psoriasis.
  • Example 1 Composition

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  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne une composition comprenant deux agents actifs solubilisés, de la vitamine D ou un de ses dérivés, et un corticostéroïde, ladite composition étant une solution filmogène, ainsi que son utilisation en dermatologie.
PCT/EP2006/004315 2005-04-19 2006-04-14 Composition d'une solution de type filmogene, comprenant de la vitamine d ou un de ses derives et un corticosteroide, et son utilisation en dermatologie WO2006111426A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP06753522A EP1874320A1 (fr) 2005-04-19 2006-04-14 Composition d'une solution de type filmogene, comprenant de la vitamine d ou un de ses derives et un corticosteroide, et son utilisation en dermatologie
US11/976,066 US20080118453A1 (en) 2005-04-19 2007-10-19 Film-forming solutions comprising vitamin D or derivative thereof and a corticosteroid and dermatological applications thereof
US12/983,608 US20110300086A1 (en) 2005-04-19 2011-01-03 Film-Forming Solutions Comprising Vitamin D or Derivative Thereof and a Corticosteroid and Dermatological Applications Thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0503913A FR2884419B1 (fr) 2005-04-19 2005-04-19 Composition de type solution filmogene comprenant de la vitamine d ou un de ses derives et un corticosteroide, et son utilisation en dermatologie
FR0503913 2005-04-19
US67629105P 2005-05-02 2005-05-02
US60/676,291 2005-05-02

Related Child Applications (1)

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US11/976,066 Continuation US20080118453A1 (en) 2005-04-19 2007-10-19 Film-forming solutions comprising vitamin D or derivative thereof and a corticosteroid and dermatological applications thereof

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WO2006111426A1 true WO2006111426A1 (fr) 2006-10-26

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WO (1) WO2006111426A1 (fr)

Cited By (9)

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Publication number Priority date Publication date Assignee Title
EP1958639A1 (fr) * 2007-02-14 2008-08-20 Polichem S.A. Utilisation de chitosanes dans le traitement de maladies inflammatoires des ongles
EP1958638A1 (fr) * 2007-02-14 2008-08-20 Polichem S.A. Utilisation de chitosanes pour augmenter la vitesse de pousse des ongles
US9345774B2 (en) 2012-07-06 2016-05-24 Leo Pharma A/S Topical composition comprising a film-forming polymer for delivering an active ingredient to skin
US9549896B2 (en) 2007-06-26 2017-01-24 Drug Delivery Solutions Limited Bioerodible patch comprising a polyaphron dispersion
US9610245B2 (en) 2011-03-14 2017-04-04 Drug Delivery Solutions Limited Ophthalmic composition
US10130640B2 (en) 2010-06-11 2018-11-20 Leo Pharma A/S Pharmaceutical spray composition comprising a vitamin D analogue and a corticosteroid
US10201490B2 (en) 2007-02-14 2019-02-12 Polichem Sa Use of chitosans for the treatment of nail inflammatory diseases
US10265265B2 (en) 2007-03-15 2019-04-23 Drug Delivery Solutions Limited Topical composition
US11696919B2 (en) 2018-03-19 2023-07-11 MC2 Therapeutics Limited Topical composition

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US4871723A (en) * 1984-10-08 1989-10-03 Teijin, Limited Method for treating psoriasis by externally administering to a patient a pharmaceutical composition containing active-type vitamin D
WO1996014048A1 (fr) * 1994-11-08 1996-05-17 Seidenschnur Edel K Traitement de troubles keratiniques et psoriatiques a l'aide d'un vernis a ongles contenant un metabolite ou un derive de vitamine d et/ou un derive de vitamine a
US5565462A (en) * 1991-09-02 1996-10-15 Teva Pharmaceutical Industries, Ltd. Composition for topical treatment of psoriasis and atopic dermatitis comprising a xanthine derivative
WO2000064450A1 (fr) * 1999-04-23 2000-11-02 Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) Composition pharmaceutique
US6231875B1 (en) * 1998-03-31 2001-05-15 Johnson & Johnson Consumer Companies, Inc. Acidified composition for topical treatment of nail and skin conditions
US20010006625A1 (en) * 1997-08-21 2001-07-05 Manfred Bohn Antipsoriatic nail polish
FR2848454A1 (fr) * 2002-12-17 2004-06-18 Galderma Res & Dev Composition pharmaceutique comprenant une association de calcitriol et d'un corticosteroide

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4871723A (en) * 1984-10-08 1989-10-03 Teijin, Limited Method for treating psoriasis by externally administering to a patient a pharmaceutical composition containing active-type vitamin D
US5565462A (en) * 1991-09-02 1996-10-15 Teva Pharmaceutical Industries, Ltd. Composition for topical treatment of psoriasis and atopic dermatitis comprising a xanthine derivative
WO1996014048A1 (fr) * 1994-11-08 1996-05-17 Seidenschnur Edel K Traitement de troubles keratiniques et psoriatiques a l'aide d'un vernis a ongles contenant un metabolite ou un derive de vitamine d et/ou un derive de vitamine a
US20010006625A1 (en) * 1997-08-21 2001-07-05 Manfred Bohn Antipsoriatic nail polish
US6231875B1 (en) * 1998-03-31 2001-05-15 Johnson & Johnson Consumer Companies, Inc. Acidified composition for topical treatment of nail and skin conditions
WO2000064450A1 (fr) * 1999-04-23 2000-11-02 Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) Composition pharmaceutique
FR2848454A1 (fr) * 2002-12-17 2004-06-18 Galderma Res & Dev Composition pharmaceutique comprenant une association de calcitriol et d'un corticosteroide

Cited By (36)

* Cited by examiner, † Cited by third party
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JP2014208709A (ja) * 2007-02-14 2014-11-06 ポリケム・エスエイ 爪の炎症性疾患の処置のためのキトサンの使用
WO2008098869A3 (fr) * 2007-02-14 2008-10-09 Polichem Sa Utilisation de chitosane pour augmenter le taux de croissance des ongles
KR101323762B1 (ko) 2007-02-14 2013-11-01 폴리켐 에스.에이. 조갑 성장율을 증가시키기 위한 키토산의 용도
EA019539B1 (ru) * 2007-02-14 2014-04-30 Полихем С.А. Применение хитозанов для лечения воспалительных заболеваний ногтей
CN101641103A (zh) * 2007-02-14 2010-02-03 波利化学公司 脱乙酰壳多糖用于治疗指/趾甲炎症性疾病的用途
JP2010518138A (ja) * 2007-02-14 2010-05-27 ポリケム・エスエイ 爪の成長速度を増大するためのキトサンの使用
JP2010518139A (ja) * 2007-02-14 2010-05-27 ポリケム・エスエイ 爪の炎症性疾患の処置のためのキトサンの使用
EP2377541A1 (fr) 2007-02-14 2011-10-19 Polichem SA Utilisation de chitosanes pour augmenter la vitesse de pousse des ongles
EP2455086A1 (fr) 2007-02-14 2012-05-23 Polichem SA Utilisation de chitosanes dans le traitement de maladies inflammatoires des ongles
CN102988405A (zh) * 2007-02-14 2013-03-27 波利化学公司 壳聚糖提高指甲生长速率的用途
AU2008214693B2 (en) * 2007-02-14 2013-05-02 Polichem S.A. Use of chitosans to increase nail growth rate
CN101641103B (zh) * 2007-02-14 2013-05-15 波利化学公司 脱乙酰壳多糖在制备用于治疗指/趾甲炎症性疾病的药物中的用途
EA018390B1 (ru) * 2007-02-14 2013-07-30 Полихем С.А. Применение хитозана, аминополисахарида хитозана и/или его физиологически приемлемой соли для ускорения роста ногтей
CN101663039B (zh) * 2007-02-14 2013-08-07 波利化学公司 壳聚糖提高指甲生长速率的用途
AU2008214695B2 (en) * 2007-02-14 2013-10-03 Polichem S.A. Use of chitosans for the treatment of nail inflammatory diseases
JP2013213048A (ja) * 2007-02-14 2013-10-17 Polichem Sa 爪の成長速度を増大するためのキトサンの使用
WO2008098871A3 (fr) * 2007-02-14 2008-10-09 Polichem Sa Utilisation de chitosans pour le traitement de maladies inflammatoires des ongles
EP1958639A1 (fr) * 2007-02-14 2008-08-20 Polichem S.A. Utilisation de chitosanes dans le traitement de maladies inflammatoires des ongles
EP1958638A1 (fr) * 2007-02-14 2008-08-20 Polichem S.A. Utilisation de chitosanes pour augmenter la vitesse de pousse des ongles
US8906881B2 (en) 2007-02-14 2014-12-09 Polichem Sa Use of chitosans for the treatment of nail inflammatory diseases
JP2015221823A (ja) * 2007-02-14 2015-12-10 ポリケム・エスエイ 爪の成長速度を増大するためのキトサンの使用
US10201490B2 (en) 2007-02-14 2019-02-12 Polichem Sa Use of chitosans for the treatment of nail inflammatory diseases
JP2016188252A (ja) * 2007-02-14 2016-11-04 ポリケム・エスエイ 爪の炎症性疾患の処置のためのキトサンの使用
US11065195B2 (en) 2007-03-15 2021-07-20 MC2 Therapeutics Limited Topical composition
US10265265B2 (en) 2007-03-15 2019-04-23 Drug Delivery Solutions Limited Topical composition
US9549896B2 (en) 2007-06-26 2017-01-24 Drug Delivery Solutions Limited Bioerodible patch comprising a polyaphron dispersion
US10660908B2 (en) 2010-06-11 2020-05-26 Leo Pharma A/S Pharmaceutical spray composition comprising a vitamin D analogue and a corticosteroid
US10130640B2 (en) 2010-06-11 2018-11-20 Leo Pharma A/S Pharmaceutical spray composition comprising a vitamin D analogue and a corticosteroid
US10688108B2 (en) 2010-06-11 2020-06-23 Leo Pharma A/S Pharmaceutical spray composition comprising a vitamin D analogue and a corticosteroid
US10682364B2 (en) 2010-06-11 2020-06-16 Leo Pharma A/S Pharmaceutical spray composition comprising a vitamind D analogue and a corticosteroid
US10617698B2 (en) 2010-06-11 2020-04-14 Leo Pharma A/S Pharmaceutical spray composition comprising a vitamind D analogue and a corticosteroid
US10716799B2 (en) 2010-06-11 2020-07-21 Leo Pharma A/S Pharmaceutical spray composition comprising a vitamin D analogue and a corticosteroid
US10154959B1 (en) 2011-03-14 2018-12-18 Drug Delivery Solutions Limited Ophthalmic composition containing a polyaphron dispersion
US9610245B2 (en) 2011-03-14 2017-04-04 Drug Delivery Solutions Limited Ophthalmic composition
US9345774B2 (en) 2012-07-06 2016-05-24 Leo Pharma A/S Topical composition comprising a film-forming polymer for delivering an active ingredient to skin
US11696919B2 (en) 2018-03-19 2023-07-11 MC2 Therapeutics Limited Topical composition

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