JP4759195B2 - 第４級アミノ基を含有するポリシロキサンの調製助剤としての使用ならびにそれを含有する薬剤 - Google Patents
第４級アミノ基を含有するポリシロキサンの調製助剤としての使用ならびにそれを含有する薬剤 Download PDFInfo
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- JP4759195B2 JP4759195B2 JP2001537545A JP2001537545A JP4759195B2 JP 4759195 B2 JP4759195 B2 JP 4759195B2 JP 2001537545 A JP2001537545 A JP 2001537545A JP 2001537545 A JP2001537545 A JP 2001537545A JP 4759195 B2 JP4759195 B2 JP 4759195B2
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- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 231100001068 severe skin irritation Toxicity 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
Classifications
-
- 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
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Toxicology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19954394.1 | 1999-11-12 | ||
| DE19954394A DE19954394A1 (de) | 1999-11-12 | 1999-11-12 | Verwendung von Polysiloxanen mit quartären Aminogruppen als Formulierungshilfe und Mittel enthalten dieselben |
| PCT/EP2000/010767 WO2001035739A1 (de) | 1999-11-12 | 2000-10-31 | Verwendung von polysiloxanen mit quartären aminogruppen als formulierungshilfsmittel und mittel enthaltend dieselben |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003513990A JP2003513990A (ja) | 2003-04-15 |
| JP2003513990A5 JP2003513990A5 (enExample) | 2007-12-06 |
| JP4759195B2 true JP4759195B2 (ja) | 2011-08-31 |
Family
ID=7928766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001537545A Expired - Fee Related JP4759195B2 (ja) | 1999-11-12 | 2000-10-31 | 第４級アミノ基を含有するポリシロキサンの調製助剤としての使用ならびにそれを含有する薬剤 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7025978B1 (enExample) |
| EP (1) | EP1241943B1 (enExample) |
| JP (1) | JP4759195B2 (enExample) |
| CN (1) | CN1213659C (enExample) |
| AR (1) | AR026240A1 (enExample) |
| AT (1) | ATE289749T1 (enExample) |
| AU (1) | AU781189B2 (enExample) |
| BR (1) | BR0015538B1 (enExample) |
| CA (1) | CA2390558C (enExample) |
| DE (2) | DE19954394A1 (enExample) |
| ES (1) | ES2238326T3 (enExample) |
| HK (1) | HK1052436B (enExample) |
| NZ (1) | NZ518871A (enExample) |
| WO (1) | WO2001035739A1 (enExample) |
| ZA (1) | ZA200202802B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19960775A1 (de) * | 1999-12-16 | 2001-06-21 | Bayer Ag | Dermal applizierbare insektizide Flüssigformulierungen zur Bekämpfung von parasitierenden Insektenlarven |
| US20020103233A1 (en) * | 2000-11-30 | 2002-08-01 | Arther Robert G. | Compositions for enhanced acaricidal activity |
| DE10320505A1 (de) * | 2003-05-08 | 2004-11-25 | Bayer Healthcare Ag | Mittel zum Bekämpfen von Parasiten an Tieren |
| JP2006298767A (ja) * | 2005-04-15 | 2006-11-02 | Sumitomo Chemical Co Ltd | ハエ亜目害虫防除剤 |
| ATE492160T1 (de) * | 2006-03-13 | 2011-01-15 | Evonik Goldschmidt Gmbh | Agrarchemikalienzusammensetzungen mit alkylendiol-modifizierten polysiloxanen |
| DE102006061537A1 (de) * | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Mittel zur Bekämpfung von Parasiten an Tieren |
| DE102006061538A1 (de) | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Kombinationsprodukt zur Bekämpfung von Parasiten an Tieren |
| US8367088B2 (en) * | 2009-10-08 | 2013-02-05 | Sergeant's Pet Care Products, Inc. | Liquid pest control formulation |
| CN102153474B (zh) * | 2011-02-14 | 2013-11-13 | 江苏扬农化工股份有限公司 | 防治动物寄生虫的酯化合物及其制备方法和应用 |
| CN102199367B (zh) * | 2011-03-30 | 2013-12-25 | 中国科学院宁波材料技术与工程研究所 | 一种高耐温性二氧化钛颜料的制备方法 |
| WO2012153735A1 (ja) * | 2011-05-10 | 2012-11-15 | 日本曹達株式会社 | 液状殺虫剤組成物 |
| CA2840704A1 (en) | 2011-06-30 | 2013-01-03 | Hansen-Ab Gmbh | Agents for the control of parasites on animals |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| WO2014060960A1 (en) | 2012-10-16 | 2014-04-24 | Solano Smart Products Ltd. | Topical formulations for treating parasitic infestations |
| AU2013204386B2 (en) * | 2012-11-01 | 2016-04-14 | Intervet International B.V. | Topical parasiticidal formulation |
| EP3324736B1 (en) | 2015-07-17 | 2019-04-10 | Evergreen Animal Health LLC | Novel spot-on active substance formulation |
| US10512628B2 (en) | 2016-04-24 | 2019-12-24 | Solano S.P. Ltd. | Dinotefuran liquid flea and tick treatment |
| EP3348143B1 (en) | 2017-01-17 | 2020-04-08 | Evergreen Animal Health LLC | Novel spot-on active substance formulation |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5578020A (en) * | 1978-12-05 | 1980-06-12 | Oreal | Surface active polysiloxan*its manufacture and composition containing it |
| JPH0429994A (ja) * | 1990-01-04 | 1992-01-31 | Dow Corning Corp | 第４アンモニウム官能シロキサン界面活性剤 |
| JPH04173747A (ja) * | 1990-11-06 | 1992-06-22 | Sagami Chem Res Center | 片末端に四級塩を有するポリオルガノシロキサンおよび経皮吸収促進剤 |
| JPH04334389A (ja) * | 1991-05-08 | 1992-11-20 | Sagami Chem Res Center | 四級塩を片末端に有するポリオルガノシロキサンおよび経皮吸収促進剤 |
| JPH0733870A (ja) * | 1993-07-23 | 1995-02-03 | Sagami Chem Res Center | ヒドロキシシリル基を末端に有するポリオキシエチレン化合物、四級塩を末端に有するブロック共重合体、および経皮吸収促進剤 |
| JPH08301705A (ja) * | 1995-05-05 | 1996-11-19 | Bayer Ag | 新規な液体組成物 |
| WO1999041987A1 (de) * | 1998-02-23 | 1999-08-26 | Bayer Aktiengesellschaft | Wasserhaltige mittel zur bekämpfung parasitierender insekten und milben an menschen |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2912485A1 (de) | 1979-03-29 | 1980-10-09 | Henkel Kgaa | Neue quartaere polysiloxanderivate, deren verwendung in haarkosmetika, sowie diese enthaltende haarwasch- und haarbehandlungsmittel |
| DE2912484A1 (de) | 1979-03-29 | 1980-10-16 | Henkel Kgaa | Neue quartaere polysiloxanderivate, deren verwendung in haarkosmetika, sowie diese enthaltende haarwasch- und haarbehandlungsmittel |
| GB2135886A (en) | 1983-02-22 | 1984-09-12 | Wellcome Found | Pesticidal pour-on formulations |
| IE58016B1 (en) | 1983-08-12 | 1993-06-16 | Ici Australia Ltd | Pour-on formulation for the control of parasites |
| DE3417912C1 (de) | 1984-05-15 | 1985-07-25 | Goldschmidt Ag Th | Betaingruppen enthaltende Siloxane,deren Herstellung und Verwendung in kosmetischen Zubereitungen |
| DE3422268C1 (de) | 1984-06-15 | 1985-07-25 | Goldschmidt Ag Th | Betaingruppen enthaltende Siloxane,deren Herstellung und Verwendung in Haarpflegemitteln |
| ZA854998B (en) | 1984-07-10 | 1987-06-24 | Aeci Ltd | Insecticidal composition |
| DE3705121A1 (de) | 1987-02-18 | 1988-09-01 | Goldschmidt Ag Th | Polyquaternaere polysiloxan-polymere, deren herstellung und verwendung in kosmetischen zubereitungen |
| DE3719086C1 (de) | 1987-06-06 | 1988-10-27 | Goldschmidt Ag Th | Diquartaere Polysiloxane,deren Herstellung und Verwendung in kosmetischen Zubereitungen |
| NZ228420A (en) | 1989-03-21 | 1990-08-28 | Ancare Distributors | Ectoparasiticidal pine oil-based spray formulation containing pyrethroids and organophosphates |
| EP0413610A3 (en) | 1989-08-18 | 1992-08-26 | Smithkline Beecham P.L.C. | Pesticidal formulations |
| JP2978245B2 (ja) | 1990-03-05 | 1999-11-15 | マリンクロット ベタリナリイ，インコーポレイテッド | 寄生虫防除組成物ならびにその製造法および使用法 |
| DE69126002T2 (de) * | 1990-11-06 | 1997-08-28 | Sagami Chem Res | An einem Kettenende mit einem quaternären Salz abgeschlossenes Polyorganosiloxan und Mittel zur Förderung der perkutanen Absorption |
| US5466458A (en) | 1992-03-09 | 1995-11-14 | Roussel Uclaf | Emulsified spray formulations |
| CA2103440A1 (en) * | 1993-06-11 | 1994-12-12 | Kimberly-Clark Worldwide, Inc. | Antimicrobial siloxane quaternary ammonium salts |
| DE4443062C2 (de) * | 1994-12-03 | 1997-07-17 | Wella Ag | Mittel und Verfahren zur dauerhaften Haarverformung |
| DE4443888A1 (de) * | 1994-12-09 | 1996-06-13 | Bayer Ag | Dermal applizierbare Formulierungen von Parasitiziden |
| DE19519007A1 (de) * | 1995-05-24 | 1996-11-28 | Bayer Ag | Insektizide Mittel |
-
1999
- 1999-11-12 DE DE19954394A patent/DE19954394A1/de not_active Withdrawn
-
2000
- 2000-10-25 AR ARP000105618A patent/AR026240A1/es unknown
- 2000-10-31 CN CNB00815581XA patent/CN1213659C/zh not_active Expired - Fee Related
- 2000-10-31 DE DE50009676T patent/DE50009676D1/de not_active Expired - Lifetime
- 2000-10-31 HK HK03104765.2A patent/HK1052436B/zh not_active IP Right Cessation
- 2000-10-31 BR BRPI0015538-1B1A patent/BR0015538B1/pt not_active IP Right Cessation
- 2000-10-31 JP JP2001537545A patent/JP4759195B2/ja not_active Expired - Fee Related
- 2000-10-31 AU AU15167/01A patent/AU781189B2/en not_active Ceased
- 2000-10-31 ES ES00977455T patent/ES2238326T3/es not_active Expired - Lifetime
- 2000-10-31 CA CA002390558A patent/CA2390558C/en not_active Expired - Fee Related
- 2000-10-31 US US10/129,774 patent/US7025978B1/en not_active Expired - Fee Related
- 2000-10-31 EP EP00977455A patent/EP1241943B1/de not_active Expired - Lifetime
- 2000-10-31 NZ NZ518871A patent/NZ518871A/en not_active IP Right Cessation
- 2000-10-31 AT AT00977455T patent/ATE289749T1/de not_active IP Right Cessation
- 2000-10-31 WO PCT/EP2000/010767 patent/WO2001035739A1/de not_active Ceased
-
2002
- 2002-04-10 ZA ZA200202802A patent/ZA200202802B/xx unknown
-
2005
- 2005-01-07 US US11/346,735 patent/US20060111323A1/en not_active Abandoned
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5578020A (en) * | 1978-12-05 | 1980-06-12 | Oreal | Surface active polysiloxan*its manufacture and composition containing it |
| JPH0429994A (ja) * | 1990-01-04 | 1992-01-31 | Dow Corning Corp | 第４アンモニウム官能シロキサン界面活性剤 |
| JPH04173747A (ja) * | 1990-11-06 | 1992-06-22 | Sagami Chem Res Center | 片末端に四級塩を有するポリオルガノシロキサンおよび経皮吸収促進剤 |
| JPH04334389A (ja) * | 1991-05-08 | 1992-11-20 | Sagami Chem Res Center | 四級塩を片末端に有するポリオルガノシロキサンおよび経皮吸収促進剤 |
| JPH0733870A (ja) * | 1993-07-23 | 1995-02-03 | Sagami Chem Res Center | ヒドロキシシリル基を末端に有するポリオキシエチレン化合物、四級塩を末端に有するブロック共重合体、および経皮吸収促進剤 |
| JPH08301705A (ja) * | 1995-05-05 | 1996-11-19 | Bayer Ag | 新規な液体組成物 |
| WO1999041987A1 (de) * | 1998-02-23 | 1999-08-26 | Bayer Aktiengesellschaft | Wasserhaltige mittel zur bekämpfung parasitierender insekten und milben an menschen |
Also Published As
| Publication number | Publication date |
|---|---|
| AU781189B2 (en) | 2005-05-12 |
| CN1390091A (zh) | 2003-01-08 |
| DE19954394A1 (de) | 2001-05-17 |
| ZA200202802B (en) | 2003-06-25 |
| AR026240A1 (es) | 2003-02-05 |
| DE50009676D1 (de) | 2005-04-07 |
| ES2238326T3 (es) | 2005-09-01 |
| AU1516701A (en) | 2001-05-30 |
| US20060111323A1 (en) | 2006-05-25 |
| HK1052436A1 (en) | 2003-09-19 |
| ATE289749T1 (de) | 2005-03-15 |
| JP2003513990A (ja) | 2003-04-15 |
| HK1052436B (zh) | 2006-04-07 |
| EP1241943B1 (de) | 2005-03-02 |
| NZ518871A (en) | 2004-10-29 |
| BR0015538A (pt) | 2002-07-16 |
| US7025978B1 (en) | 2006-04-11 |
| CA2390558A1 (en) | 2001-05-25 |
| EP1241943A1 (de) | 2002-09-25 |
| CA2390558C (en) | 2009-03-24 |
| WO2001035739A1 (de) | 2001-05-25 |
| CN1213659C (zh) | 2005-08-10 |
| BR0015538B1 (pt) | 2013-06-11 |
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