WO2014104149A1 - 皮膚適用製剤 - Google Patents

皮膚適用製剤 Download PDF

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Publication number
WO2014104149A1
WO2014104149A1 PCT/JP2013/084783 JP2013084783W WO2014104149A1 WO 2014104149 A1 WO2014104149 A1 WO 2014104149A1 JP 2013084783 W JP2013084783 W JP 2013084783W WO 2014104149 A1 WO2014104149 A1 WO 2014104149A1
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Prior art keywords
film
preparation
skin
mass
antifungal agent
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PCT/JP2013/084783
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English (en)
French (fr)
Japanese (ja)
Inventor
友保 阿閉
晃也 阿部
芳昂 横井
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大正製薬株式会社
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Priority to JP2014554518A priority Critical patent/JP6308137B2/ja
Publication of WO2014104149A1 publication Critical patent/WO2014104149A1/ja

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    • 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
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • 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
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7007—Drug-containing films, membranes or sheets
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics

Definitions

  • the present invention relates to a skin application preparation containing an antifungal agent as an active ingredient.
  • Dermatophytes such as athlete's foot, parasitize keratinous tissues and cause fungal infections. Symptoms of dermatophyte infection, athlete's foot, are lesions between the toes and may have spread to the sides and soles. In addition to direct contact, athlete's foot infection is transmitted by infected skin detached from the floor or bath mat.
  • antifungal agents with high fungicidal activity such as terbinafine hydrochloride and butenafine hydrochloride are mainstream, and products that are effective when applied once a day are being marketed due to advances in pharmaceutical technology.
  • these dosage forms are solutions, creams, and aerosols, and there is a possibility that the preparation may be peeled off due to friction with clothes or floors. It is considered that there is a problem of such a dosage form that many cases that are not cured by application once a day despite the effect of a high antifungal agent have been reported.
  • Patent Document 1 A film preparation for athlete's foot treatment in which a film using nitrocellulose is formed and the affected part is sealed is disclosed.
  • the present inventor prepared a celluloid film preparation containing an antifungal agent, but the film formed on the skin was brittle and easily peeled off. Furthermore, the water repellency was also low.
  • the present invention is to provide a film-type preparation containing an antifungal agent which improves the physical properties of the film when applied to the skin and further improves the skin permeability.
  • the present invention (1) a skin-applied preparation containing an antifungal agent, nitrocellulose, and water-soluble cellulose, (2) The skin application preparation according to (1), wherein the antifungal agent is an allylamine, benzylamine, morpholine, thiocarbamine, imidazole, azole, or triazole. (3) The skin-applied preparation according to (1), wherein the nitrocellulose is celluloid, piroxylin, or collodion, (4) The dermatological preparation according to any one of (1) to (3), further comprising a polar oil, (5) The dermatological preparation according to (4), wherein the polar oil is isopropyl myristate or glyceryl tri (caprylate / caprate). (6) The dermatological preparation according to any one of (1) to (5), which does not substantially contain water, It is.
  • the present invention it was possible to improve the physical properties of the film and further improve the skin permeability of the antifungal agent.
  • FIG. 6 is a diagram showing the results of skin permeation tests for luliconazole using hairless rat-extracted skin of the preparations of Examples 7 to 9 and Comparative Example 2.
  • the present invention is a film-forming preparation containing an antifungal agent.
  • the antifungal agent include allylamines such as terbinafine hydrochloride, benzylamines such as butenafine hydrochloride, and morpholines such as amorolfine hydrochloride.
  • Anti-fungal agents such as thiocarbamines such as Rilanaphthalate, imidazoles such as luliconasol and ketoconazole, azoles such as fluconazole and itraconazole, and triazoles such as efinaconazole, which are also available as commercial products is there.
  • One of these antifungal agents may be blended alone, or two or more may be blended as appropriate.
  • the amount of the antifungal agent used in the present invention is not particularly limited as long as the amount necessary for treatment can be supplied from the skin, but is usually 0.01% by mass or more, preferably 0.1% by mass or more, based on the whole preparation. More preferably 0.2% by mass or more, most preferably 0.5% by mass or more, usually 30% by mass or less, preferably 15% by mass or less, more preferably 5% by mass or less. The most preferable amount is 3% by mass or less. Further, it is usually 0.01 to 30% by mass, preferably 0.1 to 15% by mass, more preferably 0.2 to 5% by mass, and most preferably 0.5 to 3% by mass.
  • nitrocellulose which is the film forming agent of the present invention into a preparation
  • celluloid in which camphor is mixed with nitrocellulose piroxyline in which nitrocellulose is dissolved in a soluble organic solvent
  • nitrocellulose in a diethyl ether / ethanol solution
  • film-forming agent raw materials such as collodion dissolved in can also be used. These film-forming agent raw materials may be blended alone or in a suitable mixture of two or more. In consideration of the formation of the film, the blending amount of the film forming agent raw material is usually 0.05% by mass or more, preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and most preferably 0.00%.
  • any cellulose that can be dissolved in a preparation can be used regardless of the molecular weight or the like.
  • examples thereof include hydroxypropylcellulose, hydroxypropylmethylcellulose, methylcellulose, ethylcellulose, carboxymethylcellulose, and cellulose acetate, and these are also available as commercial products.
  • hydroxypropyl cellulose when hydroxypropyl cellulose is used as the water-soluble cellulose, it can be used regardless of the degree of substitution of the hydroxyl group, but is preferably medium-substituted hydroxypropyl cellulose.
  • the amount of hydroxypropyl cellulose is usually 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1% by mass or more in consideration of film formation.
  • blend in the quantity of 20 mass% or less, Preferably it is 10 mass% or less, More preferably, it is 5 mass% or less. Further, it is usually 0.1 to 20% by mass, preferably 0.5 to 10% by mass, more preferably 1 to 5% by mass.
  • One kind of water-soluble cellulose may be blended alone, or two or more kinds of water-soluble celluloses may be blended as appropriate.
  • the polar oil of the present invention is an ester oil that is liquid at room temperature having an IOB value (Inorganic Organic Balance value) of less than 0.5, but preferably isopropyl myristate, tri (caprylic acid / capric acid) glyceryl. , Isopropyl palmitate, crotamiton, diethyl sebacate, diisopropyl adipate, octyldodecyl myristate, and the like, which are also commercially available. These polar oils may be used alone or in a combination of two or more.
  • IOB value Organic Organic Balance value
  • the amount of polar oil is usually 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1% by mass or more, considering the formation of a film. Can be blended in an amount of 20% by mass or less, preferably 10% by mass or less, more preferably 5% by mass or less. Further, it is usually 0.1 to 20% by mass, preferably 0.5 to 10% by mass, more preferably 1 to 5% by mass.
  • the film-forming preparation of the present invention is a preparation that forms a thin film containing a drug on the skin by volatilization of the solvent immediately after application to the skin. It is a formulation in which the drug released from the film is distributed to the stratum corneum on the skin surface and is a kind of coating agent. Moreover, since nitrocellulose is insoluble in water, and a film-forming agent using these forms a film due to volatilization of the solvent after application and moisture evaporated from the skin, a preparation containing substantially no water is preferable. “Contains substantially no water” means that the preparation is composed of a non-aqueous material. However, it is allowed to contain 5% by mass or less of water derived from the raw material or the production environment in the preparation.
  • a solvent capable of dissolving a mixture of an antifungal agent, nitrocellulose, and water-soluble cellulose can be used.
  • the soluble solvent include ethyl acetate, butyl acetate, diethyl ether, dimethyl ether, methyl ethyl ketone, acetone and the like as a mixed solution with ethanol.
  • These mixed solvents with ethanol may be used alone or in combination of two or more.
  • Preferred solvents are ethanol / ethyl acetate mixture, ethanol / butyl acetate mixture, and ethanol / diethyl ether mixture.
  • the ethanol / solvent ratio is preferably as the ethanol content increases, and the ethanol / solvent ratio is preferably 1 to 99, more preferably 1.5 to 50, considering the solubility of nitrocellulose.
  • the film-forming preparation of the present invention is required to have an appropriate viscosity. This is because if the viscosity is low, it may cause non-uniformity during application and dripping.
  • a thickener can be appropriately blended.
  • thickeners include polyacrylic acid compounds (such as sodium polyacrylate), polyoxyethylene compounds (such as polyethylene glycol 400), polyhydric alcohols (such as 1,3-butylene glycol and glycerin), and silicate compounds. (E.g., light silicic anhydride) and alicyclic saturated hydrocarbon resins. These thickeners may be used alone or in a combination of two or more.
  • the blending amount of these thickeners is preferably 0.05 to 20% by mass, more preferably 0.1 to 10% by mass in view of sufficient viscosity and skin irritation.
  • the viscosity measured at 20 to 30 ° C. is preferably 0.1 to 100000 mPa ⁇ s, more preferably 0.5 to 50000 mPa ⁇ s.
  • Example 1 An allylamine antifungal agent terbinafine hydrochloride-containing film-forming preparation was obtained by the following composition and production method.
  • composition Terbinafine hydrochloride 1% Celluloid 1% Isopropyl myristate 2% Hydroxypropylcellulose-M 2% Lactic acid 2% 10% ethyl acetate Ethanol (99%) 82%
  • Production Method Terbinafine hydrochloride, isopropyl myristate, and hydroxypropylcellulose-M (manufactured by Nippon Soda Co., Ltd.) were dissolved in a solution in which celluloid was completely dissolved in ethanol / ethyl acetate. After confirming all these dissolutions, a film-forming preparation was obtained by adding lactic acid.
  • Example 2 An allylamine antifungal agent terbinafine hydrochloride-containing film-forming preparation was obtained by the following composition and production method. (composition) Terbinafine hydrochloride 1% Celluloid 1% Tri (caprylic / capric) glyceryl 2% Hydroxypropylcellulose-M 2% Lactic acid 2% 10% ethyl acetate Ethanol (99%) 82% (Production Method) In the same manner as in Example 1, a film-forming preparation was obtained.
  • Example 3 An allylamine antifungal agent terbinafine hydrochloride-containing film-forming preparation was obtained by the following composition and production method. (composition) Terbinafine hydrochloride 1% Celluloid 2% Hydroxypropylcellulose-M 2% Lactic acid 2% Ethyl acetate 20% Ethanol (99%) 73% (Production Method) In the same manner as in Example 1, a film-forming preparation was obtained.
  • Example 4 An allylamine antifungal agent terbinafine hydrochloride-containing film-forming preparation was obtained by the following composition and production method. (composition) Terbinafine hydrochloride 1% Celluloid 2% Isopropyl myristate 2% Hydroxypropylcellulose-M 2% Lactic acid 2% Ethyl acetate 20% Ethanol (99%) 71% (Production Method) In the same manner as in Example 1, a film-forming preparation was obtained.
  • Example 5 An allylamine antifungal agent terbinafine hydrochloride-containing film-forming preparation was obtained by the following composition and production method.
  • composition Terbinafine hydrochloride 1% Celluloid 2% Tri (caprylic / capric) glyceryl 2% Hydroxypropylcellulose-M 2% Lactic acid 2% 1,3-butylene glycol 5% Ethyl acetate 20% Ethanol (99%) 66%
  • Composition Terbinafine hydrochloride, tri (caprylic acid / capric acid) glyceryl, hydroxypropylcellulose-M, and 1,3-butylene glycol were dissolved in a solution in which celluloid was completely dissolved in ethanol / ethyl acetate. After confirming all these dissolutions, a film-forming preparation was obtained by adding lactic acid.
  • Comparative Example 1 An allylamine antifungal agent terbinafine hydrochloride-containing film-forming preparation was obtained by the following composition and production method. (composition) Terbinafine hydrochloride 1% Celluloid 2% Lactic acid 2% Ethyl acetate 20% Ethanol (99%) 75% (Production Method) In the same manner as in Example 1, a film-forming preparation was obtained.
  • Test example 1 With reference to the scratch strength test pencil method (JIS K 5600-5-4), for Examples 1 to 5 and Comparative Example 1, the hardness of the film formed on the slide glass was measured. It was judged that the film was fragile as it was peeled off with a hard pencil, and the film was fragile as it was peeled off.
  • the scratch strength tester is an elcometer 501 pencil hardness tester (manufactured by Elcometer, Germany) according to JIS K 5600-5-4. Using.
  • Examples 1 to 5 and Comparative Example 1 are shown in Table 1. As is apparent from Table 1, Examples 1 to 5 containing hydroxypropylcellulose-M were scratched and peeled with a softer pencil than Comparative Example 1. By adding hydroxypropylcellulose-M, the flexibility of the film could be increased. In other words, the film was not brittle. Furthermore, flexibility was not lost even if a polar oil was blended.
  • Test example 2 For Examples 1 to 5 and Comparative Example 1, water was dropped on the film formed on the slide glass to form water droplets. The contact angle between the film and the water droplet was measured immediately. The larger the contact angle, the higher the water repellency.
  • Examples 1 to 5 and Comparative Example 1 are shown in Table 2. As is clear from Table 2, Examples 1 to 5 containing hydroxypropylcellulose-M had a larger contact angle than Comparative Example 1. The water repellency of the film could be improved by adding hydroxypropylcellulose-M. Furthermore, water repellency was not lost even when a polar oil was added.
  • Example 6 An allylamine antifungal agent terbinafine hydrochloride-containing film-forming preparation was obtained by the following composition and production method. (composition) Terbinafine hydrochloride 1% Celluloid 2% Tri (caprylic / capric) glyceryl 2% Hydroxypropylcellulose-M 2% Lactic acid 2% Ethyl acetate 20% Ethanol (99%) 71% (Production Method) In the same manner as in Example 1, a film-forming preparation was obtained.
  • Test example 3 A skin permeability test using hair-removed rat-extracted skin was performed, and the skin permeability of terbinafine hydrochloride was evaluated for Examples 1, 2, 4, 6 and Comparative Example 1 up to 72 hours. The test was performed by removing the abdominal skin of hairless rats, applying each film-forming preparation, attaching it to an improved Franz-type cell, and measuring terbinafine hydrochloride transferred into the receiver solution by liquid chromatography. A pH 4.0 phosphate buffer solution was used as the receiver solution.
  • Examples 1, 2, 4, 6 and Comparative Example 1 are shown in FIG. As is clear from FIG. 1, Examples 1, 2, 4, and 6 containing polar oil and hydroxypropyl cellulose-M showed higher terbinafine hydrochloride skin permeability than Comparative Example 1. By blending polar oil and hydroxypropylcellulose-M, the skin permeability of terbinafine hydrochloride could be improved.
  • Example 7 An imidazole antifungal agent luliconazole-containing film-forming preparation was obtained by the following composition and production method. (composition) Luliconazole 1% Celluloid 2% Tri (caprylic / capric) glyceryl 2% Hydroxypropylcellulose-M 2% Ethyl acetate 20% Ethanol (99%) 73% (Production Method) A film-forming preparation was obtained by dissolving luliconazole, tri (caprylic acid / capric acid) glyceryl, and hydroxypropylcellulose-M in a solution in which celluloid was completely dissolved in ethanol / ethyl acetate.
  • Example 8 An imidazole antifungal agent luliconazole-containing film-forming preparation was obtained by the following composition and production method. (composition) Luliconazole 1% Celluloid 2% Isopropyl myristate 2% Hydroxypropylcellulose-M 2% Ethyl acetate 20% Ethanol (99%) 73% (Production Method) A film-forming preparation was obtained in the same manner as in Example 7.
  • Example 9 An imidazole antifungal agent luliconazole-containing film-forming preparation was obtained by the following composition and production method. (composition) Luliconazole 1% Celluloid 2% Hydroxypropylcellulose-M 2% Ethyl acetate 20% Ethanol (99%) 75% (Production Method) A film-forming preparation was obtained in the same manner as in Example 7.
  • Comparative Example 2 An imidazole antifungal agent luliconazole-containing film-forming preparation was obtained by the following composition and production method. (composition) Luliconazole 1% Celluloid 2% Ethyl acetate 20% Ethanol (99%) 77% (Production Method) A film-forming preparation was obtained in the same manner as in Example 7.
  • Test example 4 A skin permeability test using hairless rat-extracted skin was conducted, and for Examples 7 to 9 and Comparative Example 2, the skin permeability of luliconazole was evaluated up to 72 hours. The test was performed by removing the abdominal skin of hairless rats, applying each film-forming preparation, attaching it to an improved Franz-type cell, and measuring the luliconazole transferred into the receiver solution by liquid chromatography. A pH 4.0 phosphate buffer solution was used as the receiver solution.
  • Examples 7 to 9 and Comparative Example 2 are shown in FIG. As is clear from FIG. 2, Examples 7 to 9 containing polar oil showed higher skin permeability of luliconazole than Comparative Example 2. By blending polar oil and hydroxypropylcellulose, the skin permeability of luliconazole could be improved.
  • Example 10 A benzylamine antifungal agent butenafine hydrochloride-containing film-forming preparation was obtained by the following composition and production method. (composition) Butenafine hydrochloride 1% Celluloid 1% Isopropyl myristate 2% Hydroxypropylcellulose-M 2% Lactic acid 2% 10% ethyl acetate Ethanol (99%) 82% (Production Method) In the same manner as in Example 1, a film-forming preparation was obtained.
  • Example 10 the hardness of the film formed on the slide glass was measured by the same method as in Test Example 1. As a result, the scratch strength of Example 10 was 6B, and Example 10 was a soft film as in Examples 1-5.
  • Example 10 the contact angle of the film was measured by the same method as in Test Example 2. As a result, the contact angle of Example 10 was 72 °, and Example 10 was a film having high water repellency as in Examples 1 to 5.
  • Example 3 and Comparative Example 1 were 73.4% and 0.0%, respectively, and the adhesion of the film could be improved by adding hydroxypropylcellulose.
  • the present invention it has become possible to improve the film physical properties at the time of skin application, and further to improve the skin permeability of the antifungal agent, so that it can be suitably used as a film-forming preparation containing the antifungal agent. is there.

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PCT/JP2013/084783 2012-12-28 2013-12-26 皮膚適用製剤 WO2014104149A1 (ja)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018110693A1 (ja) 2016-12-16 2018-06-21 株式会社カネカ 爪白癬治療剤

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Publication number Priority date Publication date Assignee Title
MX2020004491A (es) * 2017-10-30 2020-08-13 Kaken Pharma Co Ltd Preparacion externa para tratar tinea unguium.
JP7365409B2 (ja) 2018-06-28 2023-10-19 エイアールエックス エルエルシー 溶解性単位用量膜構造物を製造するための分配方法

Citations (7)

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Publication number Priority date Publication date Assignee Title
JPH02311414A (ja) * 1989-05-29 1990-12-27 Shiseido Co Ltd 皮膚外用剤
WO1994015591A1 (en) * 1993-01-12 1994-07-21 Hisamitsu Seiyaku Kabushiki Kaisha Onychomycosis remedy composition
JPH07206711A (ja) * 1994-01-12 1995-08-08 Hisamitsu Pharmaceut Co Inc 爪白癬治療用組成物
WO1996011710A1 (fr) * 1994-10-13 1996-04-25 Hisamitsu Pharmaceutical Co., Inc. Preparation externe pour onychomycose
WO2008050491A1 (fr) * 2006-10-24 2008-05-02 Japan Health Science Research Center.Ltd. Préparation de film servant à former un film sur la peau
JP2010235471A (ja) * 2009-03-30 2010-10-21 Nippon Kenko Kagaku Kenkyu Center:Kk 被膜形成型製剤
WO2011044008A1 (en) * 2009-10-08 2011-04-14 Schering-Plough Healthcare Products, Inc. Low ether composition and delivery apparatus

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Publication number Priority date Publication date Assignee Title
JPS5939825A (ja) * 1982-08-30 1984-03-05 Terumo Corp 外用基剤組成物
JP5000932B2 (ja) * 2005-06-21 2012-08-15 日東電工株式会社 ニコチン含有経皮吸収製剤

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02311414A (ja) * 1989-05-29 1990-12-27 Shiseido Co Ltd 皮膚外用剤
WO1994015591A1 (en) * 1993-01-12 1994-07-21 Hisamitsu Seiyaku Kabushiki Kaisha Onychomycosis remedy composition
JPH07206711A (ja) * 1994-01-12 1995-08-08 Hisamitsu Pharmaceut Co Inc 爪白癬治療用組成物
WO1996011710A1 (fr) * 1994-10-13 1996-04-25 Hisamitsu Pharmaceutical Co., Inc. Preparation externe pour onychomycose
WO2008050491A1 (fr) * 2006-10-24 2008-05-02 Japan Health Science Research Center.Ltd. Préparation de film servant à former un film sur la peau
JP2010235471A (ja) * 2009-03-30 2010-10-21 Nippon Kenko Kagaku Kenkyu Center:Kk 被膜形成型製剤
WO2011044008A1 (en) * 2009-10-08 2011-04-14 Schering-Plough Healthcare Products, Inc. Low ether composition and delivery apparatus

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018110693A1 (ja) 2016-12-16 2018-06-21 株式会社カネカ 爪白癬治療剤

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