WO1988006884A1 - Composition pharmaceutique utilisee pour le traitement topique d'onychomycoses et procede de preparation de ladite composition - Google Patents

Composition pharmaceutique utilisee pour le traitement topique d'onychomycoses et procede de preparation de ladite composition Download PDF

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Publication number
WO1988006884A1
WO1988006884A1 PCT/HU1988/000012 HU8800012W WO8806884A1 WO 1988006884 A1 WO1988006884 A1 WO 1988006884A1 HU 8800012 W HU8800012 W HU 8800012W WO 8806884 A1 WO8806884 A1 WO 8806884A1
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WO
WIPO (PCT)
Prior art keywords
composition
topical
imidazole
ester
antimycotic
Prior art date
Application number
PCT/HU1988/000012
Other languages
English (en)
Inventor
Gyöngyi LENGYELNÉ HORVÁTH
Jeno^" NÉMETH
Original Assignee
Lengyelne Horvath Gyoengyi
Nemeth Jenoe
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 Lengyelne Horvath Gyoengyi, Nemeth Jenoe filed Critical Lengyelne Horvath Gyoengyi
Publication of WO1988006884A1 publication Critical patent/WO1988006884A1/fr

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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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; 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
    • A61K8/33—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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • 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
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures

Definitions

  • the invention relates to a pharmaceutical composition suitable for the topical treatment of nail mycosis and a process for preparing the composition.
  • Nail mycosis (onychomycosis) is a very frequent disease the treatment of which is very difficult. This disease is medicated by systemic treatment, by the oral addition of antimycotics, in this case, however, a highly increased therapeutical dose should be administered into the organism, as a consequence of which the organism suffers injuries by strong side-effects.
  • the topical treatment is carried out by using paintings and ointments. The disadvantage of these paintings and ointments is that they do not remain long-lasting on the nail surface, this treatment requires therefore the use of occlusive bandage, which hinders the patient in using his treated limb.
  • a further disadvantage of the known topical treatment is that it is only rarely successful.
  • the most radical method of treatment of nail mycosis is the ablation (surgical removal) of the nail which is, however, on one hand a very painful intervention, on the other hand, the patient. is unable to. work for a long time.
  • Aim of the invention is to prepare a composition enabling the topical treatment of nail mycosis.
  • the composition according to the invention assures a long-lasting active ingredient concentration, it cannot be washed with water and can be used very easily and the patient is not hindered in working during the therapy.
  • composition comprising a pharmaceutically effective amount of a topical antimycotic, preferably that of imidazole structure and optionally of an antiseptic, preferably salicylic acid or a salt or ester thereof dissolved if necessary in an organic solvent, preferably in a lower alcohol or in the ester thereof formed with lower carboxylic acid, a coat forming agent preferably colloidion and optionally a lower polyvalent alcohol.
  • a topical antimycotic preferably that of imidazole structure and optionally of an antiseptic, preferably salicylic acid or a salt or ester thereof dissolved if necessary in an organic solvent, preferably in a lower alcohol or in the ester thereof formed with lower carboxylic acid, a coat forming agent preferably colloidion and optionally a lower polyvalent alcohol.
  • antimycotics especially compounds of imidazole structure usable for topical treatment remain effective for a long time, if they are admixed to coat forming agents - if necessary with suitable additives and in solvents, resp. - and applied onto the surface to be treated in the form of nail polish.
  • composition for treating nail mycosis is prepared according to the invention in a way that a topical antimycotic active ingredient, preferably an antimycotic of imidazole structure and optionally an antiseptic compound, preferably salicylic acid or the salt or ester thereof is formed into nail polish by dissolving them if necessary in an organic solvent, preferably in lower alcohol or in the ester thereof formed with a lower carboxylic acid, and by mixing them with a coat forming agent, preferably with collodion as well as optionally with a lower polyvalent alcohol.
  • a topical antimycotic active ingredient preferably an antimycotic of imidazole structure and optionally an antiseptic compound, preferably salicylic acid or the salt or ester thereof is formed into nail polish by dissolving them if necessary in an organic solvent, preferably in lower alcohol or in the ester thereof formed with a lower carboxylic acid, and by mixing them with a coat forming agent, preferably with collodion as well as optionally with a lower polyvalent
  • topical antimycotic active ingredient preferably 1-(2-chlorophenyl- ⁇ , ⁇ -diphenylbenzyl)-imidazole or 1-(2,4-dichloro- ⁇ -/2,4-dichlorobenzyloxy/-phenetyl)imidazole is used.
  • compounds of antimycotic activity known per se can also be used, but owing to the wide spectrum as well as the long duration of effect the mentioned compounds proved to be the most preferable concerning the invention.
  • an antiseptic compound could optionally be used for preparing the composition in order to prolong the effect of the antimycotics.
  • Salicylic acid or a salt of ester thereof are preferably used utilizing the keratolytic activity of these compounds.
  • a coat forming agent preferably collodion, i.e. an about 4 % solution of nitrocellulose in ether-alcohol micture of 3 : 1 ratio of volume is used. After the solvent is evaporated this material forms a long-lasting waterproof coating on the surface to be treated and assures at the same time that the active ingredient remains stable and acts with suitable intensity.
  • the thus-formed lacquer coat can further be improved, namely its elasticity can be increased (its cracking can be prevented) and the effectivity of the active ingredient therein can be enhanced if a lower polyvalent alcohol, preferably propylene glycol is added to the composition as further carrier.
  • a lower polyvalent alcohol preferably propylene glycol
  • the amount of the ingredients of the composition is determined by the circumstances of the preparation and storage of said nail polish as well as circumstances of use.
  • the composition contains besides 1 part by weight of antimycotic 2-5 parts by weight of antiseptic, and an organic solvent, if needed, in an amount up to 40 parts by weight, preferably 5-35 parts by weight, 15-35 parts by weight of a coat forming agent and, if needed, 3-15 parts by weight of a lower polyvalent alcohol.
  • the composition is prepared by the simple mixing of the components.
  • the active ingredients are admixed to the other ingredients of the composition in themselves or if they are hardly soluble in the carriers, then dissolved in an organic solvent, preferably in a lower alcohol or ester, e.g. absolute ethyl alcohol or ethyl acetate.
  • composition obtained by the mixing of the active ingredients and carriers can effectively be used for treating nail mycosis caused by a wide variety of fungus strains.
  • the composition can be used especially against infections caused by Trychophyton species but it is also effective against Candida albicans, Scopulariopsis brevtcaulis and other fungus strains.
  • the composition can be used in the human and veterinary therapy, as well. In latter case it may be used for treating onychomycosis of meat-eating animals. It is particularly useful for treating dogs and cats but it can be applied to any other meat-eating animals, too.
  • the treatment is very simple and easy, the composition is applied onto the nail and the thusformed lacquer coat is renewed from time to time.
  • the nail mycosis can be alleviated by a regular treatment for 1 to 6 month. Further one month treatment is advisable after the alleviation of the symptoms in order to prevent the renewed infection.
  • composition of the invention enables the treatment of nail mycosis involving no painful intervention or deleterious side effects to the organism.
  • the application of the composition is simple and makes the treatment of nail mycosis much easier.
  • Example 1 The invention is described more detailed in the following Examples. In the Examples “part” means part by weight. Example 1
  • a composition is prepared against nail mycosis with the following composition:
  • a composition is prepared against nail mycosis containing the following compounds: 0.4 part of 1-/2,4-dichloro- ⁇ -(2,4-dichlorobenzyloxy)-phenethyl)-imidazole antimycotic, 1.0 part of salicylic acid antiseptic, 4.0 part of ethylacetate solvent, 4.0 part of propylene glycol carrier additive,
  • composition is prepared from the active ingredients and the other components according to Example 1.
  • composition of the invention The stability and biological activity of the composition of the invention have been examined in vitro,while their therapeutical usability has been tested in vivo. The details of the examination are described as follows.
  • compositions according to Examples 1 and 2 as well as those having similar composition but containing no salicylic acid have been examined in vitro.
  • the tests were carried out according to the prescriptions of the Országos Gydgyszerészeti Inté- zet (Hungarian Pharmaceutical Institute).
  • the test compositions have been kept on room temperature for six months and they have been examined from time to time for strange organic materials and decomposition products.
  • compositions containing the active ingredient according to Example 1 From the compositions containing the active ingredient according to Example 1 a sample was taken corresponding to 500 ⁇ g. of antimycotic, from which a thin layer chromatogram was made in contrast to the pure active ingredient with a 4:6 ratio of volume chloroformmethanol mixture; the chromatogram was made visible with the glacial acetic acidic-aqueous solution of potassium iodide. No imidazole decomposition product was detected even after six months. For examining carbinol decomposition products a thin layer chromatogram was made from samples similar as described before, developed this time with saturated diisopropvlether. The chromatogram was evaluated in ultraviolet light. No decomposition product could be detected either, even after six months.
  • compositions containing the active ingredient according to Example 2 From the compositions containing the active ingredient according to Example 2 a sample was taken corresponding to 200 ⁇ g. of antimycotics. A thin layer chromatogram was developed with a 6:3:1 ratio of volume n-hexane-chloroform-methanol mixture and evaluated as described before in iodine vapour atmosphere. It was found that the composition contained no strange organic materials indetectable amount even after a storage for six months.
  • compositions were examined according to the disc method specified in 6th Eddition of Pharmacopea Hungarica for the biological evaluation of antibiotics, by using self-prepared test discs.
  • the samples of the composition according to Examples 1 and 2 prepared by chain dilution according to the prescription were applied to the culture of test fungus strains inoculated into culture medium and the extinction ring was examined by different concentrations.
  • the examinations were carried out on Candida alblcans, Scopulariopsis brevicaulis as well as on Trichophyton rubrum and Menthagrophytes strains, respectively.
  • compositions according to Examples 1 and 2 proved to be the most effective against the Trichophyton strains, they showed an intensive activity against the Candida albicans strain and showed a good result against the Scopulariopsis brevicaulis strains, too. This result is very interesting considering the Trichophyton strains are fast always present among the pathogens of nail mycosis, without their killing the nail mycosis cannot be alleviated.
  • the therapeutical examination was carried out on groups of 58 voluntary patients. The patient suffering from nail mycosis have been instructed to treat their nails with the composition of Example 1 keeping the lacquer coat constantly. The patients have been examined after 28 weeks, then after further 6 weeks and the results were evaluated using the following scale:
  • the following Table shows the percentage ratio of the patients having reached the different recovery levels at the end of the examination period.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Birds (AREA)
  • Inorganic Chemistry (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La composition décrite comprend une quantité pharmaceutiquement efficace d'un antimycosique topique, ayant de préférence une structure imidazole, et éventuellement d'un antiseptique, tel que de préférence un acide salicyclique ou un sel ou ester dudit acide dissous si nécessaire dans un solvant organique, tel qu'un alcool inférieur ou son esther formé avec un acide carboxylique inférieur, un agent formant enduit, tel que de préférence un collodion et éventuellement un alcool polyvalent inférieur. On prépare ladite composition en mélangeant ces ingrédients. Ladite composition est d'un usage simple et facile et permet le traitement des onychomycoses sans intervention douloureuse ni effets secondaires negatifs sur l'organisme.
PCT/HU1988/000012 1987-03-09 1988-03-08 Composition pharmaceutique utilisee pour le traitement topique d'onychomycoses et procede de preparation de ladite composition WO1988006884A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU98787A HU200914B (en) 1987-03-09 1987-03-09 Process for producing new medical dosage unit suitable for local treatment of fungus infection of nails
HU987/87 1987-03-09

Publications (1)

Publication Number Publication Date
WO1988006884A1 true WO1988006884A1 (fr) 1988-09-22

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AU (1) AU1424988A (fr)
HU (1) HU200914B (fr)
WO (1) WO1988006884A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0515312A2 (fr) * 1991-05-23 1992-11-25 Sandoz Ltd. Composition pharmaceutique anti-mycotique contenant de la terbinafine
WO1994008591A1 (fr) * 1992-10-15 1994-04-28 Schering-Plough Healthcare Products, Inc. Traitement de l'onychomycose par l'application topique de l'acide salicylique, eventuellement en combinaison avec un retinoide
WO1999049835A1 (fr) * 1998-03-31 1999-10-07 Johnson And Johnson Consumer Companies, Inc. Composition acidifiee pour le traitement topique d'affections ungeales et cutanees
WO2003026710A1 (fr) * 2001-09-26 2003-04-03 Mbs Multination Business Services (M.E.) Ltd. Melange a utiliser comme pansement protecteur
WO2003026709A1 (fr) * 2001-09-26 2003-04-03 Mbs Multination Business Services (G.B.) Ltd. Melange liquide prevu pour etre utilise comme pansement en aerosol
US6596325B1 (en) * 1998-04-02 2003-07-22 Vroom Rene Werenfridus Lodewijk Composition for the treatment of hoof conditions in hoofed animals
US8193233B2 (en) 2009-02-13 2012-06-05 Topica Pharmaceuticals, Inc. Anti-fungal formulation
US8697753B1 (en) 2013-02-07 2014-04-15 Polichem Sa Method of treating onychomycosis
JP2015515960A (ja) * 2012-05-02 2015-06-04 サード, サミーSAAD, Samy 局所非水性医薬製剤
ES2556253R1 (es) * 2014-07-11 2016-02-02 R&D Pharma Preparaciones antifúngicas destinadas al tratamiento local de onicomicosis

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2423849A1 (de) * 1973-05-17 1974-12-12 Minnesota Mining & Mfg Filmbildende zubereitung fuer lokale anwendung auf der haut
EP0054205A1 (fr) * 1980-12-05 1982-06-23 Bayer Ag Composition anti-mycose sous forme d'émulsion et à degré élevé de libération de la substance active
EP0055396A1 (fr) * 1980-12-05 1982-07-07 Bayer Ag Compositions anti-mycose à degré élevé de libération de la substance active et en forme de pansements liquides élastiques
EP0055397A1 (fr) * 1980-12-05 1982-07-07 Bayer Ag Compositions antimycotiques à vitesse de libération élevée de la substance active et en forme de pansements liquides élastiques
EP0070525A2 (fr) * 1981-07-22 1983-01-26 Toko Yakuhin Industry Co., Ltd. Préparations fongicides pour usage externe
EP0186055A2 (fr) * 1984-12-25 1986-07-02 Bayer Ag Préparations antimycotiques sous forme de gel
WO1987002580A1 (fr) * 1985-11-04 1987-05-07 Dermatological Products Of Texas Vehicules pharmaceutiques filmogenes pour l'application de medicaments sur les ongles, compositions pharmaceutiques a base de ces vehicules, et leurs procedes d'utilisation
EP0226984A1 (fr) * 1985-12-19 1987-07-01 Hoechst Aktiengesellschaft Vernis à ongles antimycotique

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2423849A1 (de) * 1973-05-17 1974-12-12 Minnesota Mining & Mfg Filmbildende zubereitung fuer lokale anwendung auf der haut
EP0054205A1 (fr) * 1980-12-05 1982-06-23 Bayer Ag Composition anti-mycose sous forme d'émulsion et à degré élevé de libération de la substance active
EP0055396A1 (fr) * 1980-12-05 1982-07-07 Bayer Ag Compositions anti-mycose à degré élevé de libération de la substance active et en forme de pansements liquides élastiques
EP0055397A1 (fr) * 1980-12-05 1982-07-07 Bayer Ag Compositions antimycotiques à vitesse de libération élevée de la substance active et en forme de pansements liquides élastiques
EP0070525A2 (fr) * 1981-07-22 1983-01-26 Toko Yakuhin Industry Co., Ltd. Préparations fongicides pour usage externe
EP0186055A2 (fr) * 1984-12-25 1986-07-02 Bayer Ag Préparations antimycotiques sous forme de gel
WO1987002580A1 (fr) * 1985-11-04 1987-05-07 Dermatological Products Of Texas Vehicules pharmaceutiques filmogenes pour l'application de medicaments sur les ongles, compositions pharmaceutiques a base de ces vehicules, et leurs procedes d'utilisation
EP0226984A1 (fr) * 1985-12-19 1987-07-01 Hoechst Aktiengesellschaft Vernis à ongles antimycotique

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
D. HANTSCHKE, "Mykosen", Volume 19, published 1976, Grosse Verlag (Berlin), J. VANDERDOUCKT et al., "Miconazole Alcoholic Solution in the Treatment of Mycotic Nail Infections", see pages 251-256, especially page 251. *
Die Pharmazie, Vol. 36, published 1981, Berlin, DDR, W. HORSCH et al., "Beitraege zur Arzneistoffliberation aus Suspensionssalben", see pages 24-28, especially page 25, table 1, preparation G. *
E. MUTSCHLER, "Arzneimittelwirkungen", fifth edition, published 1986, Wissenschaftliche Verlagsgesellschaft m.b.H. Stuttgart, see pages 621-624. *
PATENT ABSTRACTS OF JAPAN, unexamined applications, C Section, Volume 10, No. 98, Arpil 15, 1986 (15.04.86), The Patent Office Japanese Government, page 38 C 339; & JP,A,60 228 412 (TERUMO KK). *

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6319509B1 (en) 1991-05-23 2001-11-20 Novartis Ag Pharmaceutical composition
FR2676647A1 (fr) * 1991-05-23 1992-11-27 Sandoz Sa Nouvelles formulations pour application locale contenant une allylamine et leur utilisation.
EP0515312A3 (en) * 1991-05-23 1993-04-14 Sandoz Ltd. Pharmaceutical composition containing terbinafine as an anti-mycotic agent
US5866105A (en) * 1991-05-23 1999-02-02 Novartis Ag Pharmaceutical composition
US6214360B1 (en) 1991-05-23 2001-04-10 Novartis Ag Pharmaceutical composition
EP0515312A2 (fr) * 1991-05-23 1992-11-25 Sandoz Ltd. Composition pharmaceutique anti-mycotique contenant de la terbinafine
WO1994008591A1 (fr) * 1992-10-15 1994-04-28 Schering-Plough Healthcare Products, Inc. Traitement de l'onychomycose par l'application topique de l'acide salicylique, eventuellement en combinaison avec un retinoide
US5464610A (en) * 1992-10-15 1995-11-07 Schering-Plough Healthcare Products, Inc. Method for treating onychomycosis
US6416749B1 (en) 1992-10-15 2002-07-09 Schering-Plough Healthcare Products, Inc. Treatment for onychomycosis topically applying salicylic acid, optionally in combination with a retinoid
JP2002509867A (ja) * 1998-03-31 2002-04-02 ジョンソン・アンド・ジョンソン・コンシューマー・カンパニーズ・インコーポレイテッド 爪と皮膚の局所治療用酸性化組成物
US6231875B1 (en) 1998-03-31 2001-05-15 Johnson & Johnson Consumer Companies, Inc. Acidified composition for topical treatment of nail and skin conditions
WO1999049835A1 (fr) * 1998-03-31 1999-10-07 Johnson And Johnson Consumer Companies, Inc. Composition acidifiee pour le traitement topique d'affections ungeales et cutanees
US6596325B1 (en) * 1998-04-02 2003-07-22 Vroom Rene Werenfridus Lodewijk Composition for the treatment of hoof conditions in hoofed animals
WO2003026710A1 (fr) * 2001-09-26 2003-04-03 Mbs Multination Business Services (M.E.) Ltd. Melange a utiliser comme pansement protecteur
WO2003026709A1 (fr) * 2001-09-26 2003-04-03 Mbs Multination Business Services (G.B.) Ltd. Melange liquide prevu pour etre utilise comme pansement en aerosol
US8193232B2 (en) 2009-02-13 2012-06-05 Topica Pharmaceuticals, Inc. Anti-fungal formulation
US8193233B2 (en) 2009-02-13 2012-06-05 Topica Pharmaceuticals, Inc. Anti-fungal formulation
US8362059B2 (en) 2009-02-13 2013-01-29 Topica Pharmaceuticals, Inc. Anti-fungal formulation
JP2015515960A (ja) * 2012-05-02 2015-06-04 サード, サミーSAAD, Samy 局所非水性医薬製剤
US8697753B1 (en) 2013-02-07 2014-04-15 Polichem Sa Method of treating onychomycosis
US9107877B2 (en) 2013-02-07 2015-08-18 Polichem Sa Method of treating onychomycosis
US10172811B2 (en) 2013-02-07 2019-01-08 Polichem Sa Topical antifungal composition for treating onychomycosis
ES2556253R1 (es) * 2014-07-11 2016-02-02 R&D Pharma Preparaciones antifúngicas destinadas al tratamiento local de onicomicosis

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Publication number Publication date
AU1424988A (en) 1988-10-10
HU200914B (en) 1990-09-28
HUT46850A (en) 1988-12-28

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