WO2005007140A1 - Composition pharmaceutique contenant un repulsif pour insectes - Google Patents

Composition pharmaceutique contenant un repulsif pour insectes Download PDF

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Publication number
WO2005007140A1
WO2005007140A1 PCT/KR2004/001774 KR2004001774W WO2005007140A1 WO 2005007140 A1 WO2005007140 A1 WO 2005007140A1 KR 2004001774 W KR2004001774 W KR 2004001774W WO 2005007140 A1 WO2005007140 A1 WO 2005007140A1
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WIPO (PCT)
Prior art keywords
pharmaceutical composition
hydrochloride
composition according
agent
bitten
Prior art date
Application number
PCT/KR2004/001774
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English (en)
Inventor
Jong-Hoon Kim
Original Assignee
Jong-Hoon Kim
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Filing date
Publication date
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Publication of WO2005007140A1 publication Critical patent/WO2005007140A1/fr

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Classifications

    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants

Definitions

  • the present invention relates, in general, to a pharmaceutical composition comprising an insect repellent and, more particularly, to a pharmaceutical composition for repelling ha ⁇ nful insects and treating symptoms developed at sites bitten by harmful insects, which comprises (a) an insect repellent and (b) one or more components selected from the group consisting of an antMstamine, a topical anesthetic agent and an anu ⁇ nflammatory agent
  • harmful insects e.g., sucking insects, biting insects, mites, etc.
  • insect repellents and therapeutic agents topically applied to sites bitten by harmful insects are used.
  • the sucking insects include the common gnats (e.g., Aedes, Culex and Anopheles species), moth gnats (Phlebotomi), biting gnats (Culicoides species), sandflies (Simulium species), biting flies (e.g., Stomoxys cal ⁇ trans), tsetse flies (Glossina species), horseflies (Tabamis, Haematopota and Ch ⁇ sops species), houseflies (e.g., Musca domestica and Fannia canicularis), flesh-flies (e.g., Sarcophaga camari ⁇ , myiasis-causing flies (e.g., Luc ⁇ lia cuprina, Chysom ia chloropyga,
  • the biting insects include cockroaches (e.g., Blatte ⁇ la germianica, Periplcmeta americcma,
  • Blatta orientalis S pella supellectiliwn
  • beetles e.g., Sitophilus gi'anarius, Teneb ⁇ o molitor, Dermestes lardarius, Stegobiwn pcmiceum, Anobium puntaclum, Hylotr ⁇ es baj lus
  • termites e.g., Reticulitermes luctfugus
  • ants e.g., Lasius niger
  • the mites include ticks (e.g., O ⁇ iihodo"us moubata, Jxodes ricinus, Boophilus microplus, Amblyomma hebreum) and mites in the narrower sense (e.g., Sarcoptres scabiei, Dermanyssus gallinae).
  • Insect repellents refer to compounds that function to prevent harmful insects from touching, and stinging and sucking or biting on surfaces to which they are attracted, for example, the external skin of animals and humans.
  • compositions for repelling harmful insects have been developed so far, but are unpleasant when applied to the skin and inconvenient to use due to being used separately from cosmetics, thus limiting their applications to specific cases, such as long-term applications in outdoors where a large number of harmful insects inhabit.
  • a composition with a different use e.g., a cosmetic composition, U.S. Pat. No. 5,716,602
  • an insect repellent e.g., a cosmetic composition, U.S. Pat. No. 5,716,602
  • harmful insects especially, mosquitoes
  • conventional compositions for repelling insects are not suitable for use during the time when harmful insects substantially attack people in places where people spend most of their time.
  • compositions for repelling harmful insects which are capable of being easily used during daily life (especially at home) regardless of time and place.
  • many people carry therapeutic agents to be topically applied to sites that have been bitten by harmful insects.
  • the insect-bitten sites develop symptoms including itching, edema and aching pain.
  • blood and tissue fluids are stimulated to move to the sites while Mstamine production is stimulated, thereby causing irtflammation.
  • therapeutic agents containing various antiMstamines, topical anesthetic agents and anti-inflammatory agents are used.
  • harmful insects have a habit of attacking one person several times, when the therapeutic agents are applied to insect bites immediately after the incidence of insect bites, they cannot stop the repeated incidences of insect bites.
  • An object of the present invention is to provide a pharmaceutical composition having effects on both of repelling harmful insects and treating sites bitten by harmful insects. More particularly the present invention aims to provide a pharrnaceutical composition which is capable of repelling harmful insects when applied prior to the incidence of insect bites, alleviating itohing, aching pain and iriflarnmation at a bitten site when applied after insect bites, and preventing repeated biting of riarmrul insects.
  • insect repellents have a molecular structure that does not chemically react with other therapeutically active components, thus not causing a reduction in therapeutic effects of the therapeutically active components and other side effects, and being approved to be safe to humans when used for a prolonged time
  • the present inventors added an insect repellent to a therapeutic agent carried by people and applied to sites bitten by harmful insects, and found that the resulting pharmaceutical composition has an effect of repelling riarmful insects.
  • the present invention provides a pharmaceutical composition for repelling haimful insects and treating symptoms developed at sites bitten by hamiful insects, which comprises (a) an insect repellent and (b) one or more components selected from the group consisting of an antiMstarr ⁇ ie, a topical anesthetic agent and an anti-inflammatory agent
  • the present invention provides a method of repelling harmful insects by applying the pharmaceutical composition to the external skin or clothing.
  • the pharmaceutical composition according to the present invention may comprise an insect repellent known in the art.
  • insect repellent include N-N-detfryl toluamide, N,N-diethyl benzamide, p-menthane-3,8-diol, lS,3S,4S,6R-carene-3,4-diol (granted to Sumitomo Chemical Company, U.S. Pat No.
  • 1-piperidinecarboxylic acid 2-(2- hydroxyethyl)-l-methylpropylester, l-(3-cyclohexene-l-ylcarbonyl)-2-methylpiperidine, l-(3-cyclohe xene-1-ylcarbonyl) piperidine, N ⁇ -diethyl mandelamide, isopulegol hydrate, ethyl-3-[N-n-butyl-N- acetyl] aminopropionate, d ⁇ sopropyladipate, alpha biasabal, spearmint oil, benzyl alcohol, N-N- dielhylphenylacetamide, 3-acetyl-2-(2-,6-dimethyl-5-heptenyl) oxa ⁇ lidine, (2-hydroxymethylcyclohe xyl) acetic acid lactone, and eucalyptol.
  • the pliarrnaceutical composition according to the present invention comprises N,N-diethyl toluamide as an insect repellent.
  • Each of the insect repellents may be used singly or in combinations of two or more.
  • the insect repellents may be used in an amount of 1 wt% to 50 wt%, preferably 5 wt% to 30 wt%, and most preferably 10 wt% to 25 wt%, based on the total weight of the pharmaceutical composition of the present invention.
  • the pharmaceutical composition according to the present invention may comprise a component to alleviate or treat "symptoms developed at sites bitten by ba ⁇ riful insects (e.g., itehing, aching pain, inflammation and edema)".
  • the component includes anti stamines, topical anesthetic agents and anti- inflarrrmatory agents.
  • the pharmaceutical composition according to the present invention includes at least one selected from among the components.
  • each of the components will be described in detail.
  • the pharmaceutical composition according to the present invention may comprise an antihistamine known in the art.
  • Non-limiting examples of the antihistamine include acrivastine, astemizole, azatadine, azelastine, bromo&phenhydramine, brompheriiramine, carbinoxamine, cetirizine, c o ⁇ heriiramine, cyproheptadine, dexbrompheniramine, dexc o ⁇ hemramine, dphenhydramine, mepyramine, promethazine, ebastine, ketotifen, lodoxamide, loratidine, levocuvastine, mequitazine, oxatomide, pyrilamine, phenindarnine, phenyltoloxamine, setastine, taztfylline, temelastine, terfenadine, tripelennamine, and pharmaceutically acceptable salts thereof.
  • the pharmaceutical composition according to the present invention comprises dphenhydramine as an antihistamine.
  • Each of the antiMstamines may be used singly or in combinations of two or more.
  • the antitastamines may be used in an amount of 0.05 wt% to 10 wt%, preferably 0.1 wt% to 5 wt%, and most preferably 0.5 wt% to 2.5 wt%, based on the total weight of the pharmaceutical composition of the present invention.
  • the pharmaceutical composition according to the present invention may comprise a topical anesthetic agent known in the art
  • topical anesthetic agent known in the art
  • the topical anesthetic agent include dibucaine hydrochloride, benzocaine, butamben, piperocaine hydrochloride, oxybuprocaine hydrochloride, tetracaine hydrochloride, lidocaine hydrochloride, cinchocaine hydrochloride, oxetacaine, propirocaine hydrochloride, bupivacaine hydrochloride, mepivacaine hydrochloride, dyclonine hydrochloride, fomocaine hydrochloride, quinisocaine hydrochloride, polydocanol, and pharmaceutically acceptable salts thereof.
  • the pharmaceutical composition according to the present invention comprises dibucaine hydrochloride as a topical anesthetic agent.
  • Each of the topical anesthetic agents may be used singly or in combinations of two or more.
  • the topical anesthetic agents may be used in an amount of 0.01 wt% to 5 wt%, preferably 0.05 wt% to 2.5 wt%, and most preferably 0.1 wt% to 1 wt%, based on the total weight of the pharmaceutical composition of the present invention.
  • the pharmaceutical composition according to the present invention may comprise an anti- Mammatory agent known in the art.
  • the anti-Mammatory agent includes steroidal and non- steroidal anti-inflammatory agents.
  • Non-limiting examples of the steroidal anti- ammatory agent include 21- acetoxypregnenolone, alclometasone, algestone, amcinonide, beclomethasone, betamethasone, triamcinolone, clobetasol, hydrocortisone, fludrocortisone, flurandrenolide, cortisone, desonide, methylprednisolone, fluocinonide, medrysone, desoximetasone, dexamethasone, hexacetonide, fluorometholone, diflorasone, flunisolide, prednisone, paramethasone, benetonide, halcinonide, prednisolone, and pharmaceutically acceptable salts thereof.
  • Non-limiting examples of the non-steroidal anti-inflammatory agent include acetylsalicylic acid, glycyrrhetic acid, ii domethacin, suprofen, phenylbutazone, sulindac, ibuprofen, naproxen, ketoprofen, flurbiprofen, piroxicam, diclofenac, and phannaceutically acceptable salts thereof.
  • the pharmaceutical composition according to the present invention comprises glycyrrhetic acid as an anti-inflammatory agent
  • Each of the anti- ⁇ iflammatory agents may be used singly or in combinations of two or more.
  • the anti-inflammatory agents may be used in an amount of 0.05 wt% to 5 wt%, preferably 0.01 wt% to 1 wt%. and most preferably 0.05 wt% to 0.5 wt%, based on the total weight of the pharmaceutical composition of the present invention.
  • the pharmaceutical composition according to the present invention may further comprise other components known in the art to alleviate symptoms developed at sites bitten by harmful insects (e.g., antipruritic agents or cool-feeling agents).
  • the pharmaceutical composition of the present invention preferably comprises an antipruritic agent to rapidly alleviate itching.
  • Non-limiting examples of the antipruritic agent include crotamiton, methdilazine, trimeprazine, and pharmaceutically acceptable salts thereof.
  • Each of the antipruritic agents may be used singly or in combinations of two or more.
  • the antipruritic agents may be used in an amount of 0.1 wt% to 20 wt%, preferably 0.5 wt% to 15 wt%, and most preferably 1 wt% to 10 wt%, based on the total weight of the pharmaceutical composition of the present invention.
  • the pharmaceutical composition of the present invention preferably comprises a cool-feeling agent to impart a refreshing feeling by local stimulation when applied to a bitten site of the skin.
  • cool-feeling agent examples include menthol, camphor, borneol, cineol, thymol, eucalyptus, menthane, glycosyl-mono-menthyl-oacetate, 3-l-menthoxypropane-l-2-diol s menthyl malonate, l-menthyl-3-hydroxybutyrate, menthyl salicylate, piperitone, peppermint, beta-pinene and spearmint
  • cool-feeling agents may be used singly or in combinations of two or more.
  • the cool-feeling agents may be used in an amount of 0.1 wt% to 20 wt%, preferably 0.5 wt% to 10 wt%, and most preferably 1 wt% to 5 wt%, based on the total weight of the pharmaceutical composition of the present invention.
  • the pharmaceutical composition according to the present invention is preferably formulated to a topically admirEStrable form.
  • the formulation for topical a ⁇ t ⁇ irustration includes ointments, gels, creams, liniments and lotions. This formulation may be prepared according to a guidebook known in the art: Remington's Pharmaceutical Science, 15th Edition, 1975. Mack Publishing Company, Easton, Pennsylvania 18042 (Chapter 87: Blaug, Seymour).
  • the pharmaceutical composition according to the present invention may be formulated to an ointment, which is prepared by suitably combining and processing ointment base materials, active components, additives typically contained in other ointments, etc.
  • the ointment base materials are selected from among those known in the art, such as higher fatty acids or esters thereof (e.g., adipic acid, myristic acid, palmitic acid, stearic acid, oleic acid, adipic acid esters, myristic acid esters, palmitatic acid esters, dimethyl sebacate, hexyl laurate, cetyl isooctanate, etc.), waxes (e.g., spermaceti, beeswax, cerecine, etc.), surfactants (e.g., polyoxyethylene alkylether phosphate esters, etc.), higher alcohols (e.g., cetanol, stearylalcohol, cetostearylalco
  • the pharmaceutical composition according to the present invention may be formulated to a gel, which is prepared by suitably comb ⁇ iing and processing gel base materials, active components, additives typically contained in other gels, etc.
  • the gel base materials are selected from among those known in the art, such as lower alcohols (e.g., ethanol, isopropyl alcohol, etc.), water, gelling agents (e.g., carboxyvinyl polymers, hydroxyethyl cellulose, ethyl cellulose, carboxymethyl cellulose, propylene lycol alginate esters, etc.), neutralizing agents (e.g., triethanolamine, ⁇ sopropanolamine, sodium hydroxide, etc.), surfactants (e.g., sorbitane sesquioleate, sorbitane trioleate, sorbitane monooleate, sorbitane monostearate, sorbitane monolaurate, polyethylene glycol monostearate, polyoxyethylene nonyl pheny
  • the pharmaceutical composition according to the present invention may be formulated to a cream, which is prepared by suitably combining and processing cream base materials, active components, additives typically contained in other creams, etc.
  • the cream base materials are selected from among those known in the art, such as higher fatty acid esters (e.g., myristic acid esters, palmitic acid esters, dimethyl sebacate, hexyl laurate, cetyl isooctanate, etc.), lower alcohols (e.g., ethanol, isopropanol, etc.), carbohydrates (e.g., liquid paraffin, squalane, etc.), multivalent alcohols (e.g., propylene glycol, 1,3-butylene glycol, etc.), higher alcohols (e.g., 2-hexyldecanol, cetanol, 2- octyldecanol, etc.), emulsifying agents (e.g., polyoxyethylene alkyletfiers, fatty acid esters,
  • the pharmaceutical composition according to the present invention may be formulated to a Hniment, which is prepared by suitably combining and processing an active component with alcohols (e.g., monovalent alcohols such as ethanol, propanol and isopropanol, multivalent alcohols such as polyethylene glycol, propylene glycol and butylene glycol, etc.), water, fatter acid esters (e.g., various esters of adipic acid, sebacic acid, myristic acid, etc.), surfactants (e.g., polyoxyethylene alkylethers, etc.), if desired, in combination with ultraviolet absorbers, antioxidants, neutralizers for contiolling pH, viscosity controlling agents (e.g., methyl cellulose, carboxyvinyl polymers, hydroxypropyl cellulose, etc.), and infection inhibitors.
  • alcohols e.g., monovalent alcohols such as ethanol, propanol and isopropanol, multivalent alcohols such as polyethylene glycol, prop
  • the pharmaceutical composition according to the present invention may be formulated to an aerosol, which is prepared using a liquid or a suspension of an active component and a propellant
  • the liquid or suspension may be prepared using a diluting agent typically used in the art or used in the preparation of injectable preparations.
  • propellants may be used, such as liquefied gas propellants including chlorofluoromethane, such as freon-12 (cMorodifluoromethane) and freon-123 (tiifluoro ⁇ ichloroethane), and compressed gas propellants including nitrogen and carbon dioxide gases.
  • An aerosol may include a solution adjuvant and a buffering agent, which are typically used in the art, and, if desired, may further include a colorant, a preservative, an aromatic and a flavoring agent
  • Daily dosage of the pharmaceutical composition according to the present invention may vary depending on patients' age, sex and skin condition, application sites, application frequency, formulation types, adjuvant types, etc, but typically ranges from 0.01 mg to 10 mg, preferably 0.05 mg to 5 mg, and most preferably 0.5 mgto 1 mg.
  • the present invention provides a method of repelling harmful insects by applying the pharmaceutical composition to the skin or clothing. In particular, in case of applying prior to any incidence of insect bites, the pharmaceutical composition is preferably applied to clothing rather than the skin.
  • COMPARATIVE EXAMPLE Another lbiment not containing an insect repellent was prepared according to the same method as the above Example except that diethyl toluamide in the components listed in the above Table 1 was not used.
  • the pharmaceutical composition prepared in Example was applied to the bitten sites of guinea pigs.
  • the pharmaceutical composition prepared in Comparative Example was applied to the bitten sites of guinea pigs. Then, guinea pigs were put into the cage. After two hours, guinea pigs were taken out from the cage, and sites bitten by mosquitoes were counted and recorded. Guinea pigs were again put into the cage, and, after two hours, were taken out from the cage, followed by counting the number of mosquitoes' bites. This step was repeated twice more, until efficacy of the insect repellent was maintained.
  • diethyl toluamide contained in the pliarmaceutical composition of the present invention, maintained its insect repelling effect for a certain period of time similar to that known in the art, indicating that diethyl toluamide maintains its activity even when mixed with other components.
  • EXPERIMENTAL EXAMPLE 2 Clinical tests Test subject: a present inventor Test period: 17 days The test subject, a present inventor, had a physical constitution sweating profusely and being likely to be bitten by mosquitoes. The subject was bitten with various frequencies of three to ten times daily. Clinical tests were perforated with the liniment prepared in Example, as follows.
  • Test l After the subject was bitten on the right foot, the liniment of Example was applied once to the bitten site (the first bite). Until the next morning, additional application of the liniment was not performed. - Total bites: six (including the first bite) - Two bites on hands; and three bites on arms
  • Test 2 After the subject was bitten on the right hand, the liniment of Example was applied once to the bitten site. Until the next morning, additional application of the liniment was not performed. - Total bites: six (including the first bite) - One bite on the fleshy inside of the thigh; three bites on feet; and one bite on the left hand
  • Test 4 After the subject was bitten on the left foot, the lmatiment of Example was applied once to the bitten site and a certain area of the right foot. Until the next moming, additional application of the liniment was not performed. - Total bites: five (including the first bite) - Two bites on arms; and two bites on face
  • Test 8 Prior to any incidence of mosquitoes' bites to the subject, the liniment of Example was applied twice to both hands and both feet of the subject. Until the next morning, additional application of the liniment was not performed. -No bites
  • Test 9 Prior to any incidence of mosquitoes' bites to the subject, the liniment of Example was applied twice to a lower part of each of an upper nightshirt and knee trousers. Until the next morning, additional application of the liniment was not perfomied. -Total bites: One - One bite on the right foot Test 10 Prior to any incidence of mosquitoes' bites to the subject, the liniment of Example was applied twice to a lower part of each of an upper nightshirt and knee trousers and both feet. Until the next morning, additional application of the liniment was not performed. -No bites
  • the pharmaceutical composition according to the present invention alleviated itching, aching pain and inflammation, as well as preventing repeated insect bites.
  • the tests 7 to 10 revealed that, in case of applying prior to any incidence of insect bites, the present composition is effective in repelling hamiful insects.

Abstract

L'invention concerne une composition pharmaceutique comprenant (a) un répulsif d'insecte et (b) un ou plusieurs composants sélectionnés dans le groupe comprenant : un antihistaminique, un agent anesthésique topique et un agent anti-inflammatoire. La composition pharmaceutique de l'invention présente des effets de répulsion d'insectes nuisibles et permet de traiter des zones de piqûre d'insectes nuisibles.
PCT/KR2004/001774 2003-07-16 2004-07-16 Composition pharmaceutique contenant un repulsif pour insectes WO2005007140A1 (fr)

Applications Claiming Priority (2)

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KR10-2003-0048835 2003-07-16
KR1020030048835A KR20050009502A (ko) 2003-07-16 2003-07-16 해충 퇴치제를 함유한 약제학적 조성물

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JP2007217412A (ja) * 2006-02-14 2007-08-30 Jr Chemicals コンディショニング組成物およびその使用法
WO2009154147A1 (fr) * 2008-06-16 2009-12-23 帝國製薬株式会社 Préparation analgésique/antiprurigineuse contenant de l'oxybuprocaïne pour application externe
WO2009154148A1 (fr) * 2008-06-16 2009-12-23 帝國製薬株式会社 Préparation analgésique anti-inflammatoire pour application externe
WO2014060960A1 (fr) * 2012-10-16 2014-04-24 Solano Smart Products Ltd. Formulations topiques pour le traitement d'infestations parasitaires
CN106511352A (zh) * 2016-12-23 2017-03-22 林维星 一种治疗皮炎的药物及其制备方法
US20180035675A1 (en) * 2016-08-06 2018-02-08 Hemant N. Joshi Composition of a novel topical insect repellent powder formulation
US10512628B2 (en) 2016-04-24 2019-12-24 Solano S.P. Ltd. Dinotefuran liquid flea and tick treatment

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US3933915A (en) * 1972-06-23 1976-01-20 Scm Corporation Insect repellent compositions and process having an N-substituted hydroxyalkyl amine as an active ingredient
US5298528A (en) * 1991-10-07 1994-03-29 Baker Cummins Dermatologicals, Inc. Insect repellent
US20010009925A1 (en) * 1998-06-03 2001-07-26 Danilo L. Lambino Insect repellant compositions
US6391290B1 (en) * 2001-03-21 2002-05-21 Schering-Plough Healthcare Products, Inc. Skin care compositions

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OELSCHLAGER H. ET AL.: "Antihistaminic effects of a hydrogel with the components diphenhydramine, N, N-diethyl-m-toluamide and phthalic acid dimethyl ester", ARZENEIMITTELFORSCHUNG, vol. 33, no. 1, 1983, pages 169 - 172 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007217412A (ja) * 2006-02-14 2007-08-30 Jr Chemicals コンディショニング組成物およびその使用法
EP1834627A1 (fr) * 2006-02-14 2007-09-19 JR Chemicals Compositions de soin de la peau et méthodes d'utilisation correspondantes
US20110160194A1 (en) * 2008-06-16 2011-06-30 Teikoku Seiyaku Co., Ltd Anti-Inflammatory Analgesic External Preparation
WO2009154148A1 (fr) * 2008-06-16 2009-12-23 帝國製薬株式会社 Préparation analgésique anti-inflammatoire pour application externe
JP2009298741A (ja) * 2008-06-16 2009-12-24 Teikoku Seiyaku Co Ltd 消炎鎮痛外用剤
JP2010024223A (ja) * 2008-06-16 2010-02-04 Teikoku Seiyaku Co Ltd オキシブプロカイン含有鎮痛・鎮痒用外用剤
WO2009154147A1 (fr) * 2008-06-16 2009-12-23 帝國製薬株式会社 Préparation analgésique/antiprurigineuse contenant de l'oxybuprocaïne pour application externe
AU2009261264B2 (en) * 2008-06-16 2014-07-24 Teikoku Seiyaku Co., Ltd. Analgesic anti-inflammatory preparation for external application
WO2014060960A1 (fr) * 2012-10-16 2014-04-24 Solano Smart Products Ltd. Formulations topiques pour le traitement d'infestations parasitaires
US9622478B2 (en) 2012-10-16 2017-04-18 Solano S.P. Ltd. Topical formulations for treating parasitic infestations
US10512628B2 (en) 2016-04-24 2019-12-24 Solano S.P. Ltd. Dinotefuran liquid flea and tick treatment
US20180035675A1 (en) * 2016-08-06 2018-02-08 Hemant N. Joshi Composition of a novel topical insect repellent powder formulation
CN106511352A (zh) * 2016-12-23 2017-03-22 林维星 一种治疗皮炎的药物及其制备方法

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