WO1994001098A1 - Fongicide - Google Patents

Fongicide Download PDF

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Publication number
WO1994001098A1
WO1994001098A1 PCT/JP1993/000916 JP9300916W WO9401098A1 WO 1994001098 A1 WO1994001098 A1 WO 1994001098A1 JP 9300916 W JP9300916 W JP 9300916W WO 9401098 A1 WO9401098 A1 WO 9401098A1
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WO
WIPO (PCT)
Prior art keywords
acid
solution
external preparation
surfactant
alcohol
Prior art date
Application number
PCT/JP1993/000916
Other languages
English (en)
Japanese (ja)
Inventor
Akira Yanagawa
Original Assignee
Dott Limited Company
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 Dott Limited Company filed Critical Dott Limited Company
Publication of WO1994001098A1 publication Critical patent/WO1994001098A1/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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • 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
    • 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
    • A61K31/12—Ketones
    • 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

Definitions

  • the present invention relates to a novel antifungal agent.
  • various antifungal agents are known and used as various skin treatment agents including athlete's foot treatment agents.
  • An object of the present invention is to provide a novel antifungal agent having excellent safety and excellent antibacterial properties.
  • an antifungal agent comprising as an active ingredient at least one selected from praunitol, gefarnate, teprenon, and sofacolcon.
  • the antifungal agent of the present invention contains at least 1% as an active ingredient selected from the following compounds.
  • the solution of the antifungal agent of the present invention can be applied in various forms such as ointments, creams, and powders.
  • the medicinal compound contained therein is contained in an organic liquid or organic solid that is compatible with the medicinal compound.
  • the medicinal compound and the organic liquid may be mixed at room temperature or under heating.
  • the body may be melted by heat and a medicinal compound added to the melt.
  • the medicinal compound is preferably present in a liquid or solution at room temperature in the external preparation.
  • the organic liquid includes aliphatic alcohol, terpene alcohol, fatty acid ester, N-alkylpyrrolidone, N, N-dialkylacetamide, partial ester of polyhydric alcohol, and partial ester of polyhydric alcohol.
  • Examples include anolexylene oxide adducts, alkylene oxide adducts of mono- or polyvalent anolecol, alkylene glycol monoalkyl ether, dialkyl imidazolidine, dialkyl sulfoxide and the like. Further, a nonionic interface having an HLB value of 1 to 12 can be used as the organic liquid.
  • the aliphatic alcohols include monohydric alcohols and polyhydric alcohols.
  • Such alcohols include monohydric alcohols such as ethanol, propanol, isoprono-nole, octyl alcohol, decylanolecole, 2-octinoledodecanonole, ethylene glycol, propylene glycol cornore, butylene glycol
  • alkylene glycols such as nore and isopren glycol, polyalkylene glycols such as polyethylene glycol and propylene glycol, as well as glycerin, sonorebit, sorbitan, and mannite.
  • the terpenanore coneles include Huarnesol, Phitol and Pachi. Lily alcohol and the like can be mentioned.
  • Fatty acid esters include ethylmyristate and monovalent such as isopropyl myristate, isotridecylmyristate, isopropyl laurate, isopropyl caprylate, isopropyl palmitate, isopropyl butyrate, amyl butyrate, and octyl butyrate.
  • N-alkylpyrrolidone examples include N-methylpyrrolidone, N-octylpyrrolidone, N-dodecylviridone, and the like
  • N, N-dianolekylacetamide examples include N, N- Examples include dimethylacetamide and N, N-dioctylacetamide
  • dialkyl sulfoxide examples include dimethyl sulfoxide and dioctyl sulfoxide.
  • alkylene carbonate examples include propylene carbonate and butylene carbonate.
  • partial esters of polyhydric alcohols include monoesters of higher aliphatic carboxylic acids of polyhydric alcohols as described above, for example, esthenoyl monostearate of glycerin, monobehenate of glycerin, polyethylene glycol. Cornole monoester stearate, propylene glycolonele Monostearic acid ester, butylene glycol monostearate, sorbitan monooleate, sorbitan monolaurate, sonolebitan mononoremitinate, sorbitan monostearate, sorbitan monoisostearate, etc. No.
  • alkylene oxide adducts of partial esters of polyhydric alcohols include ethylene oxide adducts or propylene oxide adducts of glycerin monostearate and ethylene glycol monostearate adducts of polyethylene glycol.
  • Oxide adduct or propylene oxide adduct propylene glycol monostearate ethylene oxide adduct or propylene oxide adduct, polypropylene dalicol monostearate ethylene oxide adduct or propylene oxide adduct Products, ethylene oxide adducts or propylene oxide adducts of monostearic acid ester of butyrene glycol, monofatty acid esters of sorbitan (lauric acid esters, palmitic acid esters, stearin Esters, Echirenokishido-added product or propylene O sulfoxide adduct of Orein ester, etc.), Bacillus ⁇ Roh record Echirenoki Cid adducts of Honoré or propylene O dimethylsulfoxide adducts.
  • Alkylene oxide adducts of polyhydric or polyhydric alcohols include ethylene oxide adducts or propylene oxide adducts of dodecyl alcohol. Ethylene oxide adducts or propylene oxide adducts of glycerin, and ethylene oxide of sorbitan Oxide adducts or propylene oxide adducts are exemplified.
  • Examples of the alkylene glycol monoalcohol etherate include ethylene glycol monoethylate ethanol, ethylene glycol monoethylate ethanol, ethylene glycol monopropyl ether, ethylene glycol monooctyl alcohol, and isopropylene. Glycol monomethyl ether, isobutylene glycol, cornole monomethinole ethereone, methinolebutylengone oleone methyl ether, and the like.
  • sofacalcon is a solid at room temperature, it is preferable to dissolve it in an organic liquid or organic solid.
  • organic liquids include aliphatic carboxylic acids that are liquid at room temperature, such as cabronic acid, enanthic acid, caprylic acid, pelargonic acid, linoleic acid, linoleic acid, and arachidonic acid, and N-alkylpyrrolidone and dialkylsulfoxide. Is mentioned.
  • the organic solid include aliphatic carboxylic acids that are solid at normal temperature, such as lauric acid, myristic acid, norremitic acid, stearic acid, isostearic acid, and behenic acid. The antifungal agent of the present invention is included.
  • One embodiment of the external preparation contains an oleaginous substance and a surfactant together with the medicinal compound.
  • Oily substances are substances that are liquid or solid at room temperature, and are fatty acids, fatty acid esters, aromatic carboxylic acid esters, phosphoric acid esters, higher fatty acid triglycerides, higher fatty alcohols, higher fatty acids, terpenes, vaseline, This includes lanolin, liquid paraffin, squalane, beeswax and mixtures thereof.
  • the fatty acid ester a liquid or solid monovalent fatty acid ester and a polyvalent fatty acid ester at room temperature are used.
  • the fatty acid ester is generally a saturated or unsaturated linear or branched mono- or polyvalent fatty acid having about 4 to 22 carbon atoms, preferably about 8 to 18 carbon atoms. It can be as low as 8 and higher alcohol esters.
  • the fatty acid components in this fatty acid ester include butyric acid, lactic acid, octanoic acid, inoctanoic acid, dimethyloctanoic acid, nonanoic acid, pupuric acid, lauric acid, myristic acid, palmitic acid, stearic acid, a Examples include nstearic acid, oleic acid, behenic acid, adipic acid, azelaic acid, sebacic acid and the like.
  • examples of the alcohol component include ethanol, propanol, isopropanol, butanol, hexanol, decanol, myristinole alcohol, dodecanol, cetyl alcohol, hexadecyl alcohol, behenyl alcohol, and the like. be able to.
  • Suitable fatty acid esters include, for example, isoprovir myristate, isododecyl myristate, octyldodecyl myristate, myristyl myristate, decyl oleate, oleyl oleate, instellin Hexyl decyl acid, butyl stearate, cetyl inoctoate, hexyl decyl dimethyl octanoate, NO, "isopropyl noremitate, hexyl laurate, isopropyl acrylate, myristyl lactate, oleyl adipate, Getyl adipate, diisobutyl adipate, diisodecyl adipate, dioctyl adipate, dibenzyl adipate, di (2-methoxethyl) adipate, dityl sebacate, di
  • Examples of the aromatic carboxylate include getyl phthalate, dibutyl phthalate, and dioctyl phthalate.
  • Examples of phosphate esters include trioleyl phosphate, tridodecyl phosphate, and trioctyl phosphate. I can do it.
  • the above-mentioned partial esters of polyhydric alcohols and alkylene oxide adducts thereof can also be used as the oily substance.
  • the higher fatty acid triglycerides are liquid or semi-solid at room temperature, and various types of naturally occurring animal and vegetable substances can be used.These are generally called fats and oils and are widely available industrially. It is. Many types of vegetable oils, beef tallow, liver oil, lanolin, lard, etc. can be mentioned, but preferably vegetable oil, especially olive, camellia oil, soybean oil, rapeseed oil, corn oil, castor oil, safflower oil, etc. can do.
  • Examples of the higher aliphatic alcohols include cetanol, stearyl alcohol, behenyl alcohol, lanolin alcoholic, and fuarnesol.
  • Higher fatty acids include octanoic acid, nonanoic acid, hydropric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, behen, montanic acid
  • the surfactant include anionic, cationic, nonionic and amphoteric surfactants, but from the viewpoint of low irritation to the skin. Ionic surfactants are advantageously used.
  • the nonionic surfactant include an ethylene oxide surfactant, a polyhydroxy surfactant, and a polymer surfactant.
  • ethylene oxide-based surfactant examples include an ethylene oxide adduct of a higher alcohol, an ethylene oxide adduct of a higher fatty acid, an ethylene oxide adduct of an alkylphenol, and an ethylene oxide adduct of an aliphatic amine. Things, aliphatic amides Examples include lenoxide adducts, ethylene oxide adducts of polyhydric alcohols, and ethylenoxide z propylene oxide block copolymers.
  • polyhydroxy surfactant examples include glycerin monofatty acid ester, pentaerythritol fatty acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, fatty acid amide of ethanolanolamine and alkylene oxide adduct thereof. And the like.
  • polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glyceryl monofatty acid ester, polyoxypropylene monofatty acid ester, sorbitan fatty acid ester, polyoxyethylene alcohol ether and the like are advantageously used. These surfactants are used alone or in the form of a mixture.
  • the content of the pharmaceutically active compound is 0.1 to 20 wt%, preferably 3 to 10 wt%.
  • the content of the oily substance is not particularly limited, and an appropriate amount is blended depending on the desired properties of the external preparation.
  • the blending amount is not particularly limited, and a suitable amount is blended according to the desired properties of the external preparation.
  • the surfactant is used in an amount of 5 to 50 wt%, preferably 20 to 45 wt% of the total external preparation when the external preparation is a non-emulsion type, and when the external preparation is an emulsion type. Is 1 to 20 wt%, preferably 5 to 15 wt ° / 0 .
  • alkanolamine can be blended as a stabilizer of the medicinal compound.
  • Alkanolamines include diethanolamine, triethanolamine, isopropanolamine, diisobutanol, triisopropanolamine, diisopropanolamine and dibutanolamine. And tributanolamine.
  • the compounding amount of alkanolamine is 0.5 to 15 wt%, preferably 2 to: 0 wt% in all the external preparations.
  • the external preparation of the present invention can contain water, a filler, a thickener (polymer compound), a coloring agent, a fragrance, an emulsion stabilizer, a bactericide, a force-proofing agent, and the like, if necessary.
  • Organic and inorganic fine powders are used as the filler.
  • the particle size of the filler is usually from 0.1 to 20 / m, preferably from 0.5 to 10 ⁇ .
  • Suitable examples of the filler include silica, alumina, titania, resin powder, silicate powder, clay powder, sepiolite powder, montmorillonite powder, fluorinated powder, hydroxypropyl cellulose. And the like.
  • the external preparation containing the active ingredient of the present invention is applied in various forms such as ointments, creams, lotions and the like, and its composition is appropriately adjusted according to the form of the product.
  • the external preparation of the present invention is applied in the form of a non-emulsion type ointment mixture, the following composition is preferable.
  • the oily substance a solid oily substance or a mixture of a solid oily substance and a liquid oily substance is used.
  • a surfactant at room temperature and Z or an oily substance.
  • examples of the solid oily substance include the various oily substances described above.
  • solid surfactants include polyoxyethylene glycerin fatty acids such as POE monostearate (5) glyceryl, POE (15) glyceryl monostearate, and POE (40) glyceryl monostearate.
  • Esters polyglycerin fatty acid esters such as tetraglyceryl monostearate, tetraglyceryl tristearate, decaglyceryl trioleate, glyceryl monomyristate, glyceryl monostearate, jig distearate Glycerin fatty acid esters such as luceryl, sorbitan monomonoremitate. Sorbitan monoesterate, sorbitan sesquistearate, sorbitan tristearate, etc.
  • Sorbitan fatty acid esters such as tristearate POE (20)
  • Polyester such as sorbitan Oxyethylene
  • Polyoxyethylene sorbite fatty acid esters such as bitane, hexostearic acid P ⁇ E (6) sorbite, polyethylene glycol fatty acids such as monostearic acid PEG (4 EO), polyethylene dartlylate, etc.
  • the external preparation is prepared by mixing an organic liquid solution of a medicinal compound, a heat-melted mixed liquid of an oily substance and a surfactant, and then, if necessary, adding a filler and uniformly It can be prepared by mixing and allowing to cool.
  • the external preparation containing the pharmaceutically active ingredient of the present invention is applied in the form of an emulsion-type ointment mixture, the following composition is preferable.
  • L 0 wt%, preferably 1 to 5 wt%
  • the oily substance may be a solid at room temperature or a mixture of a solid at room temperature and a liquid at room temperature.
  • the surfactant those having an HLB of 8 to 15, preferably 9 to 12 are used.
  • the above-mentioned external preparation is gradually added to the medicinal compound or its organic liquid solution A under stirring at a temperature of about 60 ° C. or higher into a molten mixture B of an oily substance and a surfactant under stirring.
  • the mixture can be prepared by mixing a filler as needed and allowing the resulting mixture to cool.
  • the external preparation containing the pharmaceutically active ingredient of the present invention is applied in the form of an emulsion-type creamy mixture, the following component composition is preferable.
  • L 0 wt%, preferably 1 to 5 wt%
  • the components (1) and (2) are mixed under heating to form a mixture A.
  • the components (3) and (4) are mixed under heating to form a molten mixture B.
  • the mixture A is gradually added to the molten mixture B under heating and stirring, and then the components (6) and (5) are added and mixed, and if necessary, a filler is added and mixed, followed by cooling.
  • the external preparation in this case can be an oil / water type and a water / oil type emulsion.
  • a surfactant having HLB 9 to 18 is preferably used as the surfactant, and in the case of the water / oil type, a surfactant having HLB 2 to 8 is used.
  • the oily substance a solid at room temperature or a mixture of a solid at room temperature and a liquid at room temperature is used.
  • the thickener include water-soluble polymers, for example, carboxyvinyl polymer, methylcellose, hydroxyxetinoresenorelose, canoleboxymethinoresenorelose, and ⁇ . Sonoleginic acid ⁇ 7 ', Anoleginate. Examples include propylene glycol cornole, chitosan, polyvinyl alcohol, and sodium hydroxide.
  • the agent A comprising a solution obtained by dissolving the medicinal compound of the component (1) in an organic liquid solution of the component (2) is added to the component (3)
  • the temperature of the hot-melt mixture of the solid oily substance at room temperature and the solid surfactant at room temperature is maintained at a temperature equal to or higher than the melting point of the substance, and the substance is converted into a solid. Be careful not to precipitate.
  • the thickener of the component (5) is preferably added after the addition of the water of the component (6), but it can be dissolved in the water of the component (6) in advance and added simultaneously with the water.
  • another water-soluble substance for example, urea or a polyhydric alcohol can be dissolved in water as the component (6) in advance.
  • the amount of urea to be added should be in the range of 5 to 20 wt%, preferably 5 to 10 wt% of the total external preparation.
  • the water of the component (6) preferably has a pH maintained in the range of 4.5 to 5.5, and as such a pH-adjusted water, it is preferable to use a phosphate buffer.
  • the external preparation is prepared by dissolving the medicinal compound of the component (1) in the organic liquid of the component (2) to form a solution, It can be obtained by adding the components (3), (4), (5) and (6) to this solution as needed.
  • This lotion type can be applied as a liquid lotion as it is, or can be filled into an aerosol can with a propellant such as liquefied natural gas and used as an aerosol type lotion.
  • the external preparation is applied directly to the affected area several times a day, for example, 1 to 3 times, or processed into a patch, a plaster, a puppet or the like. Can be applied to the affected area several times a day.
  • the frequency of application can be increased or decreased as appropriate according to the severity of the disease.
  • the external preparation of the present invention is characterized in that the pharmaceutically active compounds contained therein are highly safe. Since it is dissolved in an organic liquid or organic solid, it does not show inflammatory properties, has excellent skin or mucous membrane absorbability, and has a high therapeutic effect. Further, since the external preparation of the present invention is not administered systemically but is administered to a diseased site, it can be administered safely without causing side effects such as skin irritation, redness, and itching.
  • the antifungal agent of the present invention includes fungi, for example, Aspergillus furni gatus, Can adi da albicans, Canadida tropicalis, Sporotnrix schenckii, Epidermo ht on ⁇ 1 oc co s um, Micros po ru urn audou inii, It has excellent bacterial action against Microcrosporum canis, Trichophyton mentagrophytes, Trichophyton rubrum and the like.
  • the antifungal agent of the present invention can be used as a remedy for various diseases caused by fungi, including a remedy for athlete's foot.
  • Agar slant cultures of each fungus were suspended in a 0.1% Tween 80 phosphate buffer solution to obtain as much as possible a suspension.
  • 5 / i 1 of this bacterial solution was added to each drug-added Sabouraud agar plate (256, 128, 64, 32, 16, 8, 8, 4, 0 ⁇ g 1) was inoculated.
  • These plate media were cultured in a 25 ° C incubator, and after 7 days, the minimum concentration of the drug that inhibited the growth of the test bacteria was determined.
  • Canad i da trop i ca 1 is ⁇ 256 ⁇ 256> 256> 256
  • Mi cr o s po r urn can i s 16 ⁇ 256 256 128

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

Abstract

Remède d'une grande efficacité thérapeutique contre les dermatoses dues à des champignons tels que le tinea pedis, contenant au moins un composé pharmaceutiquement efficace choisi parmi le plaunotol, le géfarnate, la téprénone et la sofalcone.
PCT/JP1993/000916 1992-07-02 1993-07-02 Fongicide WO1994001098A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP20029192 1992-07-02
JP4/200291 1992-07-02

Publications (1)

Publication Number Publication Date
WO1994001098A1 true WO1994001098A1 (fr) 1994-01-20

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Application Number Title Priority Date Filing Date
PCT/JP1993/000916 WO1994001098A1 (fr) 1992-07-02 1993-07-02 Fongicide

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WO (1) WO1994001098A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11171796A (ja) * 1997-12-08 1999-06-29 Ohta Pharmaceut Co Ltd テプレノン経口投与用製剤およびその製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3868413A (en) * 1970-06-04 1975-02-25 Searle & Co 2-(4-Hydroxy-1-alkynyl)-5-oxocyclopent-1-enealkanoic acids, 3-hydroxy congeners corresponding and derivatives thereof
US4018811A (en) * 1972-02-11 1977-04-19 American Cyanamid Company 3-Alkyl-2-(6-carboxyhexyl)cyclopentanones and esters and salts thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3868413A (en) * 1970-06-04 1975-02-25 Searle & Co 2-(4-Hydroxy-1-alkynyl)-5-oxocyclopent-1-enealkanoic acids, 3-hydroxy congeners corresponding and derivatives thereof
US4018811A (en) * 1972-02-11 1977-04-19 American Cyanamid Company 3-Alkyl-2-(6-carboxyhexyl)cyclopentanones and esters and salts thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 119, No. 5, Refer to Abstract No. 45069w; & INFLAMMATION, Vol. 13, No. 2, 155-61, (1993). *
THE MERCK INDEX, Eleventh Edition, 7506, 9083, 4273, 8658, published by MERCK & CO. INC. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11171796A (ja) * 1997-12-08 1999-06-29 Ohta Pharmaceut Co Ltd テプレノン経口投与用製剤およびその製造方法

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