HRP20030856A2 - Use of neuronal sodium chanell antagonists for the control of ectoparasites in homeothermic animals - Google Patents
Use of neuronal sodium chanell antagonists for the control of ectoparasites in homeothermic animals Download PDFInfo
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- HRP20030856A2 HRP20030856A2 HR20030856A HRP20030856A HRP20030856A2 HR P20030856 A2 HRP20030856 A2 HR P20030856A2 HR 20030856 A HR20030856 A HR 20030856A HR P20030856 A HRP20030856 A HR P20030856A HR P20030856 A2 HRP20030856 A2 HR P20030856A2
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- optionally substituted
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Classifications
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- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines having two or more nitrogen atoms in the same ring, e.g. oxadiazines
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P33/14—Ectoparasiticides, e.g. scabicides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
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- Chemical & Material Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Agronomy & Crop Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
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- Organic Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
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HR20030856A HRP20030856A2 (en) | 2002-10-21 | 2003-10-20 | Use of neuronal sodium chanell antagonists for the control of ectoparasites in homeothermic animals |
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EP (2) | EP1967067A3 (ja) |
JP (1) | JP2004143172A (ja) |
KR (1) | KR101110579B1 (ja) |
CN (1) | CN100531728C (ja) |
AR (1) | AR041668A1 (ja) |
AT (1) | ATE405161T1 (ja) |
AU (2) | AU2003255177B2 (ja) |
BR (1) | BR0304618A (ja) |
CA (1) | CA2444692C (ja) |
CO (1) | CO5510023A1 (ja) |
CY (1) | CY1108430T1 (ja) |
DE (1) | DE60323028D1 (ja) |
DK (1) | DK1413201T3 (ja) |
ES (1) | ES2311677T3 (ja) |
HR (1) | HRP20030856A2 (ja) |
ME (1) | ME00571A (ja) |
MX (1) | MXPA03009595A (ja) |
NZ (2) | NZ567277A (ja) |
PL (1) | PL362962A1 (ja) |
PT (1) | PT1413201E (ja) |
RS (1) | RS51054B (ja) |
SI (1) | SI1413201T1 (ja) |
TW (1) | TWI311465B (ja) |
ZA (1) | ZA200308147B (ja) |
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US7906128B2 (en) | 2002-10-21 | 2011-03-15 | Wyeth Llc | Use of neuronal sodium channel antagonists for the control of ectoparasites in homeothermic animals |
US7531186B2 (en) * | 2003-12-17 | 2009-05-12 | Merial Limited | Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz |
KR100595446B1 (ko) * | 2004-01-19 | 2006-07-03 | 삼성전자주식회사 | 디스플레이장치 |
TWI350728B (en) * | 2004-10-08 | 2011-10-21 | Wyeth Corp | Amitraz compositions |
UY28617A1 (es) * | 2004-11-12 | 2006-06-30 | Popley Pharma Ltda | Nuevas composiciones |
US20100095900A1 (en) * | 2005-05-24 | 2010-04-22 | Wyeth Llc | Device and method for controlling insects |
TWI368505B (en) * | 2005-05-24 | 2012-07-21 | Wyeth Corp | Versatile high load concentrate compositions for control of ecto-parasites |
US20060293260A1 (en) * | 2005-05-24 | 2006-12-28 | Wyeth | Useful high load concentrate compositions for control of ecto-and endo-parasites |
US7749527B2 (en) * | 2005-05-24 | 2010-07-06 | Wyeth Llc | Gel compositions for control of ecto-parasites |
TW200846029A (en) * | 2007-02-09 | 2008-12-01 | Wyeth Corp | High dose, long-acting ectoparasiticide for extended control |
CL2008001614A1 (es) * | 2007-06-05 | 2008-08-08 | Wyeth Corp | Composicion parasiticida veterinaria que comprende un disolvente que no contiene hidroxilo, un estabilizador, amitraz y opcionalmente una lactona macrociclica y miristato de isopropilo; y su uso para tratar o controlar una infestacion o infeccion par |
US9173728B2 (en) | 2008-11-19 | 2015-11-03 | Merial Inc. | Multi-cavity container having offset indentures for dispensing fluids |
CN102271672B (zh) | 2008-11-19 | 2015-02-04 | 梅里亚有限公司 | 用于治疗寄生物感染的包含单独的或与甲脒组合的1-芳基吡唑的组合物 |
AU2010224685A1 (en) | 2009-03-18 | 2011-11-03 | Fidopharm, Inc. | Parasiticidal formulation |
KR102027723B1 (ko) | 2010-12-27 | 2019-10-01 | 인터벳 인터내셔널 비.브이. | 국소 적용 이속사졸린 제제 |
US9622478B2 (en) | 2012-10-16 | 2017-04-18 | Solano S.P. Ltd. | Topical formulations for treating parasitic infestations |
CN105168560A (zh) * | 2015-07-22 | 2015-12-23 | 贵州谷丰生态农业发展有限责任公司 | 一种从鹅耳孔驱赶虱子的方法 |
US10512628B2 (en) | 2016-04-24 | 2019-12-24 | Solano S.P. Ltd. | Dinotefuran liquid flea and tick treatment |
SI3723739T1 (sl) | 2017-12-15 | 2024-08-30 | Tarsus Pharmaceuticals, Inc. | Paraziticidni pripravki na osnovi izoksazolina in njihova uporaba za zdravljenje blefaritisa |
Family Cites Families (28)
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---|---|---|---|---|
CA1176167A (en) | 1980-03-06 | 1984-10-16 | John J. Windheuser | Use of n,n-diethyl-m-toluamide for enhancing skin permeation of bio-affecting agents |
US4560553A (en) | 1981-07-07 | 1985-12-24 | Merck & Co., Inc. | Use of eucalyptol for enhancing skin permeation of bio-affecting agents |
GB8525447D0 (en) | 1985-10-16 | 1985-11-20 | Fbc Ltd | Pesticidal compositions |
US5116850A (en) | 1987-11-30 | 1992-05-26 | E. I. Du Pont De Nemours And Co. | Heterocyclic pyrazoline carboxanilides |
EP0462456B1 (en) | 1990-06-16 | 1996-05-08 | Nihon Nohyaku Co., Ltd. | Hydrazinecarboxamide derivatives, a process for production thereof, and uses thereof |
CA2093351A1 (en) | 1990-10-05 | 1992-04-06 | Charles R. Harrison | Semicarbazone arthropodicides |
DE69108356T2 (de) | 1990-11-17 | 1995-07-20 | Nihon Nohyaku Co Ltd | Hydrazonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung. |
US5462938A (en) | 1990-12-21 | 1995-10-31 | Annus; Gary D. | Arthropodicidal oxadiazinyl, thiadiazinyl and triazinyl carboxanilides |
US5250532A (en) | 1991-04-11 | 1993-10-05 | Dowelanco | 3,4,N-trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their use as insecticides |
JPH07165697A (ja) | 1993-10-04 | 1995-06-27 | Nissan Chem Ind Ltd | セミカルバゾン化合物及び有害生物防除剤 |
JP3711581B2 (ja) | 1995-03-31 | 2005-11-02 | 日産化学工業株式会社 | セミカルバゾン誘導体及び有害生物防除剤 |
JPH09301947A (ja) | 1996-05-17 | 1997-11-25 | Nissan Chem Ind Ltd | セミカルバゾン誘導体及び有害生物防除剤 |
US5968990A (en) | 1997-10-14 | 1999-10-19 | Isp Investments Inc. | Water-dilutable, microemulsion concentrate and pour-on formulations thereof |
JP4239298B2 (ja) * | 1998-07-27 | 2009-03-18 | 住友化学株式会社 | 動物の外部寄生虫防除剤 |
WO2000029387A1 (fr) * | 1998-11-12 | 2000-05-25 | Sagami Chemical Research Center | Derives de 2- anilino (3h)- pyrimidone, intermediaires dans la production de ces derniers, procede de production de ces derniers et pesticides contenant ces derniers comme ingredient actif |
US5965137A (en) * | 1998-11-16 | 1999-10-12 | Advanced Medical Instruments | Insect repellent composition and method for inhibiting the transmission and treatment of symptoms of vector-borne diseases |
AU765767B2 (en) * | 1999-03-12 | 2003-09-25 | Basf Aktiengesellschaft | Synergistic insecticidal compositions |
MY138864A (en) | 1999-07-05 | 2009-08-28 | Nihon Nohyaku Co Ltd | Ant controllers and method for application thereof |
AUPQ441699A0 (en) * | 1999-12-02 | 2000-01-06 | Eli Lilly And Company | Pour-on formulations |
JP2001240583A (ja) * | 1999-12-17 | 2001-09-04 | Mitsubishi Chemicals Corp | ジハロプロペニルオキシベンゼン誘導体及びこれを有効成分とする有害生物防除剤 |
JP2001240541A (ja) * | 2000-03-02 | 2001-09-04 | Kanto Kachiku Rinsho Center:Kk | 動物外部寄生虫の駆除方法及び駆除剤 |
AU781682B2 (en) * | 2000-03-20 | 2005-06-09 | Zoetis Services Llc | Sustained-release compositions for parenteral administration |
IL143225A (en) * | 2000-05-24 | 2008-03-20 | Pfizer | Preparation of drugs containing α-amylase inhibitors to treat hyperacidity of the inner abdomen |
JP5093429B2 (ja) * | 2000-10-18 | 2012-12-12 | 日本農薬株式会社 | 動物用外部寄生性害虫防除剤及びその使用方法 |
US7906128B2 (en) | 2002-10-21 | 2011-03-15 | Wyeth Llc | Use of neuronal sodium channel antagonists for the control of ectoparasites in homeothermic animals |
US20040122075A1 (en) | 2002-12-16 | 2004-06-24 | Wyeth | N-phenyl-3-cyclopropylpyrazole-4-carbonitriles as ectoparasiticidal agents |
EP1773121B1 (en) | 2004-07-06 | 2011-02-09 | Basf Se | Liquid pesticide compositions |
TWI350728B (en) | 2004-10-08 | 2011-10-21 | Wyeth Corp | Amitraz compositions |
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