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WO1996014048A1 - 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 - Google Patents

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 Download PDF

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Publication number
WO1996014048A1
WO1996014048A1 PCT/DK1995/000439 DK9500439W WO9614048A1 WO 1996014048 A1 WO1996014048 A1 WO 1996014048A1 DK 9500439 W DK9500439 W DK 9500439W WO 9614048 A1 WO9614048 A1 WO 9614048A1
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WO
WIPO (PCT)
Prior art keywords
vitamin
nail
lacquer
derivative
pharmaceutical
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.)
Ceased
Application number
PCT/DK1995/000439
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English (en)
Inventor
Edel K. Seidenschnur
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Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of WO1996014048A1 publication Critical patent/WO1996014048A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
    • A61K31/593—9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/07—Retinol compounds, e.g. vitamin A
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/203—Retinoic acids ; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings

Definitions

  • the present invention relates to the use of a pharmaceutical film forming nail lacquer containing a vitamin D metabolite or a vitamin D derivative, or a vitamin A derivative, or a combination of such substances for the treatment of keratinic and/or psoriatic disorders affecting human nails on fingers and toes, the nail bed, the nail matrix, and/or the surrounding tissue.
  • a pharmaceutical film forming nail lacquer containing a vitamin D metabolite or a vitamin D derivative, or a vitamin A derivative, or a combination of such substances for the treatment of keratinic and/or psoriatic disorders affecting human nails on fingers and toes, the nail bed, the nail matrix, and/or the surrounding tissue.
  • Therapeutic substances belonging to the categories of vitamin D metabolites and derivatives and vitamin A derivatives are often lipophilic and exhibit extremely low solubilities in solvents usually considered acceptable for long term exposure to the human body. On the other hand, these substances usually show high affinity to keratin.
  • the pharmaceutical nail preparation of the present invention comprises a solvent system which is suitable for dissolution of the quantities of the active substances of these groups necessary for penetration at therapeutic levels into and through the nail plate. Such quantities may be several times higher than the concentrations usually employed in topical skin formulations.
  • the solvent system is selected to comprise solvents acceptable for short term exposure by application to the nail plates.
  • the solvent system employed shall also be suitable for dissolution of the polymer resin selected for the preparation.
  • lacquer preparation according to this invention containing a suitable solvent system and a suitable polymer resin dissolved therein will, after subsequent evaporation of the solvents, leave the active substances indwelling in the polymer in close contact with the keratinic nail plate.
  • the polymer resin is chozen among those offered by respectable pharmaceutical suppliers as being of innocuous nature. Furthermore, as a main characteristic of a suitable polymer resin, it shall form a water insoluble stable film layer on the nail surface, from which the active substance(s) can penetrate into the nail plate. It is an important feature of the invention that the nail plate is given a functional role in the drug administration, namely the function of a drug depot gradually releasing the active substances to the tissue under the nail and surrounding it.
  • a primary criterium for the choice of the solvent system is its ability to dissolve the active substance(s) and the polymer resin.
  • the solvent system shall also be chozen in such a way that the solvents evaporate quickly after application of the lacquer to the nails, preferably within 3-5 minutes leaving on the nails a dry lacquer film being a stable continous self supporting layer of sufficient hardness, durability and flexibility.
  • Various organic solvents may be suitable, in particular methylene chloride or iso- propanol, which is an efficient solvent for even the most sparingly soluble substances within the therapeutic categories concerned.
  • Isopropanol is a preferred solvent since the main solvent primarily shall be of inert nature, and because isopropanol is known as being safe for application to human skin. Methylene chloride may be considered less acceptable for exposure to skin, but nevertheless usefull in this particular case because of the very small quantities employed . It has the advantage of facilitating penetration into keratinic material, for which reason it may be used at least partly as a solvent in the nail preparation. By using it, it shall also be considered that it may exert other functions beyond that of an inert solvent and a penetration enhancer, sice it may also act as an evaporation enhancer at the same time.
  • the polymer resin preferred for the preparation of this invention is an acrylic resin which is soluble in lower alcohols including isopropanol, and also in methylene chloride, and therefore, the solvent or solvent system chozen as being suitable for dissolution of the active substance(s) of the therapeutic categories concerned, is also appropriate as a solvent for the polymer resin.
  • R 1 can be H or CH 3 and R 2 can be lower aliphatic substituents.
  • Various types of these resins are available, and they may be used solely or may be mixed with one another according to the particular requirements.
  • Polymer resins of this category have good swelling capacities and porosity which ensures a high rate of diffusion and a high rate of permeability for the active substance(s).
  • the use of such polymer resins also guarantees a high degree of resistance of the resulting lacquer film against washing off and against mechanical damage. This makes it possible for the active substance(s) to remain in close contact with the nail surface for a long period of time, and consequently the period between two applications can be as long as several days, may be 3-4 days, whereas daily application is still possible, if so desired.
  • previously applied lacquer film shall be removed by use of a suitable solvent.
  • the solvent system may also contain other solvents, part of which may be an evaporation enhancer selected to have a boiling point lower than the main solvent, and part of which may be an evaporation retarder selected among suitable solvents having a boiling point higher than the main solvent.
  • a solvent system composed according to these principles and primarily based on isopropanol as the main solvent methylene chloride may be a suitable evaporation enhancer, and in this way having a special functional presence in the solvent system.
  • Another possible evaporation enhancer will be ethyl acetate.
  • butyl acetate is a suitable choice, although other miscible and compatible solvents having a boiling point at a similar level maybe chosen.
  • Other examples of evaporation retarders are toluene, butanol, amyl alcohol and amyl acetate.
  • the active substances to be used in the preparation according to the invention are compounds active against keratinic and/or psoriatic disorders and selected from the groups of therapeutically active agents being vitamin D metabolites or vitamin D derivatives or vitamin A derivatives, or a combination of substances from these groups.
  • calcitriol is most suitable for the purpose.
  • Active substances belonging to the group of vitamin D-derivatives may be selected from those described in the following published documents:
  • vitamin D derivatives comprise calcipotriol (USAN: calcipotriene) which is mentioned in Example 5 of said reference c) and also mentioned by its code name MC 903 in said reference b) or alternatively 24-homo-1 ⁇ ,25-dihydroxy-vitamin D 3 mentioned in said reference e) or as still another alternative 20-oxa-21-nor-1 ⁇ ,25-dihydroxy-vitamin D 3 mentioned in said reference f).
  • Vitamin A derivatives may preferably be either tretinoin or isotretinoin.
  • Suitable combinations may be selected to comprise any combination of therapeutically active, and compatible substances of the two categories being on one hand the vitamin D metabolites and vitamin D derivatives and on the other hand vitamin A derivatives. More specifically, a combination of a vitamin A derivative with a vitamin D metabolite or vitamin D derivative may be selected from those described in Australian Patent Application Number 37161/93, application date 23. April 1993.
  • the active compounds may be present as added to the preparation in any form desirable, as base or salt, being anhydrous or as a hydrate, as suitable for the preparation with respect to relevant properties such as stability and solubility.
  • An example of this feature is the hydrate of calcipotriol mentioned in the published patent application GB 93763 filed 15. January 1993.
  • a preferred embodiment of a composition in accordance with the invention is a composition containing a vitamin D metabolite or a vitamin D derivative, selected from the substances referred to, in a concentration within the range 0.01-1.0 wt/vol %, more specifically calcipotriol (USAN: calcipotriene) in a concentration of 0.05- 0.5 wt/vol %, or a vitamin A derivative as referred to in ccncentrations within the range 0.1-10 wt/vol %, or a combination of such active substances selected from these two categories in concentrations within the ranges mentioned.
  • a vitamin D metabolite or a vitamin D derivative selected from the substances referred to, in a concentration within the range 0.01-1.0 wt/vol %, more specifically calcipotriol (USAN: calcipotriene) in a concentration of 0.05- 0.5 wt/vol %, or a vitamin A derivative as referred to in ccncentrations within the range 0.1-10
  • the polymer resin to be used in the nail lacquer preparation of this invention may be selected from those provided by Rohm Pharma under their trade mark EUDRAGIT R , being water insoluble copolymerizates based on acrylic acid esters and neutral methacrylic acid esters having an average molecular weight of about 150,000 which shall be present in the fluent lacquer preparation in a concentration of about 10-20 wt/vol%, preferably about 12.5 %.
  • the polymer resins will be selected from the EUDRAGIT R types designated EUDRAGIT R RL-100 and EUDRAGIR R RS-100, although types belonging to other groups as for example EUDRAGIT R
  • E-100 may be used as well .
  • the main solvent which may be isopropanol or methylene chloride, or both employed at the same time, but with a preference for isopropanol in concentrations of 10-73 % of the fluent lacquer composition more specifically 15-65 %, and within this preferred embodiment an evaporation enhancer, which may be ethyl acetate and/or methylene chloride, preferably ethyl acetate present in an amount of 5-20 % in the fluent lacquer composition, preferably 10-20 %.
  • an evaporation retarder which preferably is, although not limited to, butyl acetate in concentrations of 5-80 % of the fluent lacquer composition, preferably 5-65 %, and especially 5-40 % of the composition.
  • the preferred main solvent and/or the preferred evaporation enhancer may be totally or partially replaced by methylene chloride, which may be present in concentrations within the range of 5-75 % of the fluent lacquer composition depending on the functional role designated for it in the particular composition.
  • a solvent system as described provides proper qualities of the nail lacquer, not only with respect to suitable bioavailability of sparingly soluble compounds of the groups of therapeutic substances concerned, but it also provides proper qualities of the lacquer with regard to its application by producing a continous and homogenous fluent preparation of suitable viscosity and with good spreadability allowing a thin homogenous layer to be applied to the nail surface on which it will dry within few minutes leaving a continous self supporting and well adhering lacquer film on the nail plate.
  • the use of the polymer resins of the preferred type guarantees resistance to mechanical damage and to washing off of the lacquer coating. Furtehrmore , the good swelling capacity and porosity of the copolymerizates employed with this invention provides high rates of diffusion and permeability of active substances thereby facilitating their penetration into the nail plate.
  • a preparation in accordance with the invention containing calcipotriol (USAN:calcipotriene) as the active substance and isopropanol as the main solvent may have the following composition:
  • a preparation in accordance with the invention containing calcipotriol (calcipotriene) as the active substance, and a solvent system partly comprising methylene chloride may have the following composition:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

Traitement de troubles kératiniques ou psoriatiques courants dans les tissus situés au-dessous ou autour des ongles avec un vernis à ongles pharmaceutique contenant un métabolite de vitamine D ou bien un dérivé de vitamine D, ou un dérivé de vitamine A thérapeutiquement efficaces ou une combinaison de ces substances dans une composition de vernis filmogène insoluble dans l'eau, comprenant une résine acrylique composée d'un copolymérisat d'esters d'acide acrylique et d'esters d'acide méthacrylique, et un système de solvants assurant des caractéristiques appropriées de viscosité, des propriétés d'écoulement et d'étalement, un temps de séchage court et une dureté, une adhésion sur les ongles ainsi qu'une durabilité satisfaisantes de la couche mince de vernis sèche. L'application sur les ongles une ou deux fois par semaine permet la pénétration de la substance ou des substances actives dans les tissus kératiniques de la couche cornée du limbe unguéal, laquelle fait office de dépôt pour l'administration d'une ou de plusieurs substances actives en concentrations thérapeutiques actives sur le lit, la matrice et les parties périphériques de l'ongle.
PCT/DK1995/000439 1994-11-08 1995-11-06 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 Ceased WO1996014048A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK128494A DK128494A (da) 1994-11-08 1994-11-08 Behandling af keratinøse og psoriatiske sygdomstilstande med neglelak indeholdende vitamin D metabolit, eller derivat, og/eller vitamin A derivat
DK1284/94 1994-11-08

Publications (1)

Publication Number Publication Date
WO1996014048A1 true WO1996014048A1 (fr) 1996-05-17

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PCT/DK1995/000439 Ceased WO1996014048A1 (fr) 1994-11-08 1995-11-06 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

Country Status (2)

Country Link
DK (1) DK128494A (fr)
WO (1) WO1996014048A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997034644A1 (fr) * 1996-03-16 1997-09-25 Hoechst Aktiengesellschaft Formulations topiques pour traiter le psoriasis de l'ongle
US6352686B2 (en) * 1997-08-21 2002-03-05 Aventis Pharma Deutschland Gmbh Antipsoriatic nail polish
FR2884419A1 (fr) * 2005-04-19 2006-10-20 Galderma Sa Composition de type solution filmogene comprenant de la vitamine d ou un de ses derives et un corticosteroide, et son utilisation en dermatologie
WO2006111426A1 (fr) * 2005-04-19 2006-10-26 Galderma S.A. 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
US10201490B2 (en) 2007-02-14 2019-02-12 Polichem Sa Use of chitosans for the treatment of nail inflammatory diseases

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987000834A1 (fr) * 1985-08-02 1987-02-12 Leo Pharmaceutical Products Ltd. A/S Nouveaux analogues de la vitamine d
EP0226984A1 (fr) * 1985-12-19 1987-07-01 Hoechst Aktiengesellschaft Vernis à ongles antimycotique
EP0298271A1 (fr) * 1987-06-16 1989-01-11 Hoechst Aktiengesellschaft Email à ongles à activité antimycotique et procédé pour le préparer
WO1989010351A1 (fr) * 1988-04-21 1989-11-02 Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis Nouveaux analogues de vitamine d
EP0389778A1 (fr) * 1989-02-24 1990-10-03 F. Hoffmann-La Roche Ag Vernis à ongles
US5102654A (en) * 1990-04-18 1992-04-07 Revlon, Inc. Nail enamel emulsion lacquer comprising a water phase and a lacquer phase
EP0515312A2 (fr) * 1991-05-23 1992-11-25 Sandoz Ltd. Composition pharmaceutique anti-mycotique contenant de la terbinafine
EP0579915A1 (fr) * 1992-05-20 1994-01-26 F. Hoffmann-La Roche Ag Composition pharmaceutique contenant de l'acide 9-cis- ou 13-cis retinoique ou de l'acitretine et un dérivé de la vitamine D
EP0580968A2 (fr) * 1992-05-20 1994-02-02 F. Hoffmann-La Roche Ag Derivés fluorinés de la vitamine D3
WO1994014412A1 (fr) * 1992-12-18 1994-07-07 Beiersdorf Ag Combinaisons synergiques de principes actifs pour les soins cosmetiques ou dermatologiques de la peau ou des elements tegumentaires
WO1995005829A1 (fr) * 1993-08-21 1995-03-02 Lts Lohmann Therapie-Systeme Gmbh & Co. Kg Systeme therapeutique pour le traitement du psoriasis

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987000834A1 (fr) * 1985-08-02 1987-02-12 Leo Pharmaceutical Products Ltd. A/S Nouveaux analogues de la vitamine d
EP0226984A1 (fr) * 1985-12-19 1987-07-01 Hoechst Aktiengesellschaft Vernis à ongles antimycotique
EP0298271A1 (fr) * 1987-06-16 1989-01-11 Hoechst Aktiengesellschaft Email à ongles à activité antimycotique et procédé pour le préparer
WO1989010351A1 (fr) * 1988-04-21 1989-11-02 Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis Nouveaux analogues de vitamine d
EP0389778A1 (fr) * 1989-02-24 1990-10-03 F. Hoffmann-La Roche Ag Vernis à ongles
US5102654A (en) * 1990-04-18 1992-04-07 Revlon, Inc. Nail enamel emulsion lacquer comprising a water phase and a lacquer phase
EP0515312A2 (fr) * 1991-05-23 1992-11-25 Sandoz Ltd. Composition pharmaceutique anti-mycotique contenant de la terbinafine
EP0579915A1 (fr) * 1992-05-20 1994-01-26 F. Hoffmann-La Roche Ag Composition pharmaceutique contenant de l'acide 9-cis- ou 13-cis retinoique ou de l'acitretine et un dérivé de la vitamine D
EP0580968A2 (fr) * 1992-05-20 1994-02-02 F. Hoffmann-La Roche Ag Derivés fluorinés de la vitamine D3
WO1994014412A1 (fr) * 1992-12-18 1994-07-07 Beiersdorf Ag Combinaisons synergiques de principes actifs pour les soins cosmetiques ou dermatologiques de la peau ou des elements tegumentaires
WO1995005829A1 (fr) * 1993-08-21 1995-03-02 Lts Lohmann Therapie-Systeme Gmbh & Co. Kg Systeme therapeutique pour le traitement du psoriasis

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
STN INTERNATIONAL, File CAPLUS, Accession Number 1992:248622, KRAGBALLE KNUD, "Vitamin D Analogs in the Treatment of Psoriasis"; & J. CELL. BIOCHEM., (1992), 49(1), 46-52. *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997034644A1 (fr) * 1996-03-16 1997-09-25 Hoechst Aktiengesellschaft Formulations topiques pour traiter le psoriasis de l'ongle
US6352686B2 (en) * 1997-08-21 2002-03-05 Aventis Pharma Deutschland Gmbh Antipsoriatic nail polish
FR2884419A1 (fr) * 2005-04-19 2006-10-20 Galderma Sa Composition de type solution filmogene comprenant de la vitamine d ou un de ses derives et un corticosteroide, et son utilisation en dermatologie
WO2006111426A1 (fr) * 2005-04-19 2006-10-26 Galderma S.A. 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
US10201490B2 (en) 2007-02-14 2019-02-12 Polichem Sa Use of chitosans for the treatment of nail inflammatory diseases

Also Published As

Publication number Publication date
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