ES2285565T3 - Represion de parasitos en animales mediante el uso de derivados de imidazo(1,2-b)piridazina. - Google Patents
Represion de parasitos en animales mediante el uso de derivados de imidazo(1,2-b)piridazina. Download PDFInfo
- Publication number
- ES2285565T3 ES2285565T3 ES04815474T ES04815474T ES2285565T3 ES 2285565 T3 ES2285565 T3 ES 2285565T3 ES 04815474 T ES04815474 T ES 04815474T ES 04815474 T ES04815474 T ES 04815474T ES 2285565 T3 ES2285565 T3 ES 2285565T3
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- Prior art keywords
- optionally substituted
- alkoxy
- compound
- alkyl
- aryl
- Prior art date
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- Expired - Lifetime
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- 241001465754 Metazoa Species 0.000 title claims abstract description 41
- 244000045947 parasite Species 0.000 title claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
- 125000003118 aryl group Chemical group 0.000 claims abstract description 37
- 238000002360 preparation method Methods 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 18
- 239000012453 solvate Substances 0.000 claims abstract description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 16
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 14
- 150000004942 imidazo[1,2-b]pyridazines Chemical class 0.000 claims abstract description 14
- 206010061217 Infestation Diseases 0.000 claims abstract description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 12
- 208000006968 Helminthiasis Diseases 0.000 claims abstract description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 10
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims abstract description 10
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims abstract description 9
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 11
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- VTVRXITWWZGKHV-UHFFFAOYSA-N imidazo[1,2-b]pyridazine Chemical compound N1=CC=CC2=NC=CN21 VTVRXITWWZGKHV-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 244000000013 helminth Species 0.000 claims description 5
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
- 150000004892 pyridazines Chemical class 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
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- 125000004414 alkyl thio group Chemical group 0.000 description 7
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- XJGAMGIHDJFISU-UHFFFAOYSA-N 2-bromo-1-[4-(2-methoxyethoxy)phenyl]ethanone Chemical compound COCCOC1=CC=C(C(=O)CBr)C=C1 XJGAMGIHDJFISU-UHFFFAOYSA-N 0.000 description 6
- DTXVKPOKPFWSFF-UHFFFAOYSA-N 3(S)-hydroxy-13-cis-eicosenoyl-CoA Chemical compound NC1=CC=C(Cl)N=N1 DTXVKPOKPFWSFF-UHFFFAOYSA-N 0.000 description 6
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- 241000244206 Nematoda Species 0.000 description 6
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- 241000607479 Yersinia pestis Species 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
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- VSDQKRFQYAYSNB-UHFFFAOYSA-N 3-iodo-2-[4-(2-methoxyethoxy)phenyl]-6-propoxyimidazo[1,2-b]pyridazine Chemical compound IC=1N2N=C(OCCC)C=CC2=NC=1C1=CC=C(OCCOC)C=C1 VSDQKRFQYAYSNB-UHFFFAOYSA-N 0.000 description 5
- LWTGZLYCNAUHAP-UHFFFAOYSA-N 6-(cyclopropylmethoxy)pyridazin-3-amine Chemical compound N1=NC(N)=CC=C1OCC1CC1 LWTGZLYCNAUHAP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
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- 125000001188 haloalkyl group Chemical group 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
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- MYYUYHRXRKLQCI-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-2-[4-(2-methoxyethoxy)phenyl]imidazo[1,2-b]pyridazine Chemical compound C1=CC(OCCOC)=CC=C1C1=CN(N=C(OCC2CC2)C=C2)C2=N1 MYYUYHRXRKLQCI-UHFFFAOYSA-N 0.000 description 4
- YXEDABZQSZKQKZ-UHFFFAOYSA-N 6-propoxypyridazin-3-amine Chemical compound CCCOC1=CC=C(N)N=N1 YXEDABZQSZKQKZ-UHFFFAOYSA-N 0.000 description 4
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Plant Pathology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Agronomy & Crop Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53372903P | 2003-12-31 | 2003-12-31 | |
| US533729P | 2003-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2285565T3 true ES2285565T3 (es) | 2007-11-16 |
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| JP (1) | JP4758909B2 (enExample) |
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| AT (1) | ATE362475T1 (enExample) |
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Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7943160B2 (en) * | 2002-05-09 | 2011-05-17 | Scimetrics Limited Corp. | Pest control methods |
| CN101065352A (zh) | 2004-09-23 | 2007-10-31 | 先灵-普劳有限公司 | 使用新的三氟甲磺酰苯胺肟醚衍生物控制动物中的寄生虫 |
| DE602005017419D1 (de) | 2004-11-19 | 2009-12-10 | Schering Plough Ltd | Kontrolle von parasiten bei tieren mittels verwendung von parasitiziden 2-phenyl-3-(1h-pyrrol-2-yl) acrylonitril-derivaten |
| WO2006070943A1 (ja) * | 2004-12-28 | 2006-07-06 | Takeda Pharmaceutical Company Limited | 縮合イミダゾール化合物およびその用途 |
| US20060281695A1 (en) * | 2005-06-09 | 2006-12-14 | Schering-Plough Animal Health Corporation | Control of parasites in animals by N-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and N-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives |
| US7750000B2 (en) | 2005-09-02 | 2010-07-06 | Bayer Schering Pharma Ag | Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments |
| DE102005042742A1 (de) * | 2005-09-02 | 2007-03-08 | Schering Ag | Substituierte Imidazo[1,2b]pyridazine als Kinase-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
| US8119667B2 (en) * | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
| TW200803903A (en) * | 2006-04-28 | 2008-01-16 | Nihon Mediphysics Co Ltd | Novel compound having affinity to amyloid |
| KR20090010987A (ko) | 2006-05-19 | 2009-01-30 | 니혼 메디피직스 가부시키가이샤 | 신규 아밀로이드 친화성 화합물 |
| DE102006029447A1 (de) * | 2006-06-21 | 2007-12-27 | Bayer Schering Pharma Ag | Oxo-substituierte Imidazo[1,2b]pyridazine, deren Herstellung und Verwendung als Arzneimittel |
| KR20090025282A (ko) * | 2006-06-21 | 2009-03-10 | 니혼 메디피직스 가부시키가이샤 | 신규 아밀로이드 친화성 화합물 |
| US8044049B2 (en) * | 2006-08-04 | 2011-10-25 | Takeda Pharmaceutical Company Limited | Fused heterocyclic derivative and use thereof |
| EP2098522B1 (en) * | 2006-11-30 | 2011-10-19 | Nihon Medi-Physics Co., Ltd. | Compounds having affinity for amyloid |
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| EP2102154A1 (en) * | 2006-12-13 | 2009-09-23 | Schering-Plough Ltd. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
| WO2008072682A1 (ja) * | 2006-12-15 | 2008-06-19 | Daiichi Sankyo Company, Limited | イミダゾ［１，２－ｂ］ピリダジン誘導体 |
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| US7868001B2 (en) | 2007-11-02 | 2011-01-11 | Hutchison Medipharma Enterprises Limited | Cytokine inhibitors |
| TWI491610B (zh) * | 2008-10-09 | 2015-07-11 | 必治妥美雅史谷比公司 | 作為激酶抑制劑之咪唑并嗒腈 |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| CN102574815A (zh) | 2009-08-05 | 2012-07-11 | 杜邦公司 | 介离子杀虫剂 |
| KR20120050467A (ko) | 2009-08-05 | 2012-05-18 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 메소이온성 살충제 |
| US20120295931A1 (en) | 2010-02-05 | 2012-11-22 | Lutz Juergen | Spiroindoline compounds for use as anthelminthics |
| ES2624845T3 (es) | 2010-09-29 | 2017-07-17 | Intervet International B.V. | Compuestos de N-heteroarilo con unidad de puente cíclico para el tratamiento de enfermedades parasitarias |
| RU2596185C2 (ru) | 2010-09-29 | 2016-08-27 | Интервет Интернэшнл Б.В. | N-гетероарильные соединения |
| WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
| TWI617559B (zh) * | 2010-12-22 | 2018-03-11 | 江蘇恆瑞醫藥股份有限公司 | ２－芳基咪唑并［１，２－ｂ］嗒．２－苯基咪唑并［１，２－ａ］吡啶，和２－苯基咪唑并［１，２－ａ］吡衍生物 |
| KR20140038527A (ko) | 2011-06-20 | 2014-03-28 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 연충 감염을 치료하기 위한 복소환식 화합물 |
| WO2013017678A1 (en) | 2011-08-04 | 2013-02-07 | Intervet International B.V. | Novel spiroindoline compounds |
| SG11201402664VA (en) | 2011-11-28 | 2014-06-27 | Du Pont | N- (4 -quinolinylmethyl) sulfonamide derivatives and their use as anthelmintics |
| US9260441B2 (en) | 2012-03-28 | 2016-02-16 | Intervet Inc. | Heteroaryl compounds with cyclic bridging unit |
| AU2013241853B2 (en) | 2012-03-28 | 2017-11-09 | Intervet International B.V. | Heteroaryl compounds with A-cyclic bridging unit |
| WO2013158422A1 (en) | 2012-04-17 | 2013-10-24 | E. I. Du Pont De Nemours And Company | Heterocyclic compounds for controlling invertebrate pests |
| WO2014099837A1 (en) | 2012-12-18 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Sulfonamide anthelmintics |
| US10188108B2 (en) | 2015-04-08 | 2019-01-29 | Bayer Cropscience Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
| JP6913076B2 (ja) | 2015-08-07 | 2021-08-04 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 有害生物防除剤としての２−（ヘタ）アリール−置換縮合ヘテロ環誘導体 |
| RU2018119344A (ru) | 2015-10-26 | 2019-11-28 | Байер Кропсайенс Акциенгезельшафт | Конденсированные бициклические гетероциклические производные в качестве средства для борьбы с вредителями |
| WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2017174414A1 (de) | 2016-04-05 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Naphthalin-derivate als schädlingsbekämpfungsmittel |
| EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| BR112019001135B1 (pt) * | 2016-07-19 | 2022-11-01 | Bayer Cropscience Aktiengesellschaft | Derivados de heterociclo bicíclico fundido como pesticidas, seu uso, formulação agroquímica, e método para controlar pragas animais |
| MA45918A (fr) | 2016-08-15 | 2019-06-19 | Bayer Ag | Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides |
| CN109963860A (zh) | 2016-09-19 | 2019-07-02 | 拜耳作物科学股份公司 | 吡唑并[1,5-a]吡啶衍生物及其作为农药的用途 |
| WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
| TW201837026A (zh) | 2017-01-10 | 2018-10-16 | 德商拜耳廠股份有限公司 | 作為除害劑之雜環衍生物（二） |
| UY37556A (es) | 2017-01-10 | 2018-07-31 | Bayer Ag | Derivados heterocíclicos como pesticidas |
| GB201700692D0 (en) * | 2017-01-16 | 2017-03-01 | Salvensis | Novel compounds and their use in the treatment of schistosomiasis |
| WO2018138050A1 (de) | 2017-01-26 | 2018-08-02 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| CN110582503B (zh) | 2017-04-24 | 2022-05-31 | 拜耳公司 | 作为有害物防治剂的稠合双环杂环化合物衍生物 |
| EP3305786A3 (de) | 2018-01-22 | 2018-07-25 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| EP3755700B1 (de) | 2018-02-21 | 2021-11-24 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2020002593A1 (en) | 2018-06-29 | 2020-01-02 | Intervet International B.V. | Compound for use against helminthic infection |
| PE20211275A1 (es) | 2018-07-09 | 2021-07-19 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos heterociclicos antihelminticos |
| BR112021010430A2 (pt) | 2019-02-26 | 2021-08-24 | Bayer Aktiengesellschaft | Derivados de heterociclo bicíclico fundido como pesticidas |
| MX2021010217A (es) | 2019-02-26 | 2021-09-21 | Bayer Ag | Derivados heterociclos biciclicos condensados como plaguicida. |
| KR20220002890A (ko) | 2019-03-19 | 2022-01-07 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 아자-벤조티오펜 및 아자-벤조푸란 화합물 |
| JP7644121B2 (ja) | 2019-12-18 | 2025-03-11 | インターベット インターナショナル ベー． フェー． | アザインドール構造を含む駆虫剤化合物 |
| US20230148316A1 (en) | 2019-12-18 | 2023-05-11 | Intervet Inc. | Anthelmintic compounds comprising a quinoline structure |
| MX2022015038A (es) * | 2020-05-29 | 2023-01-04 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos heterociclicos como anthelminticos. |
| US20240043446A1 (en) | 2020-12-11 | 2024-02-08 | Intervet Inc. | Anthelmintic compounds comprising a thienopyridine structure |
| GB202019622D0 (en) * | 2020-12-11 | 2021-01-27 | Adorx Therapeutics Ltd | Antagonist compounds |
| WO2025027117A1 (en) | 2023-08-02 | 2025-02-06 | Intervet International B.V. | Carboxamide-4-quinoline compounds with anthelmintic activity |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725407A (en) * | 1971-04-08 | 1973-04-03 | American Cyanamid Co | 6-substituted amino-3-nitroimidazo(1,2-b)pyridazines and methods of preparing the same |
| US3905974A (en) * | 1972-09-28 | 1975-09-16 | American Cyanamid Co | 6-Substituted oxo and thio-3-nitroimidazo(1,2-b)-pyridazines and methods of preparing same |
| DD202692A5 (de) | 1979-12-04 | 1983-09-28 | Ciba Geigy | Verfahren zur herstellung neuer derivate des 2-amino-aethanols |
-
2004
- 2004-12-22 CA CA2551867A patent/CA2551867C/en not_active Expired - Fee Related
- 2004-12-22 AT AT04815474T patent/ATE362475T1/de not_active IP Right Cessation
- 2004-12-22 ES ES04815474T patent/ES2285565T3/es not_active Expired - Lifetime
- 2004-12-22 AU AU2004312506A patent/AU2004312506B2/en not_active Ceased
- 2004-12-22 US US11/019,597 patent/US7759349B2/en not_active Expired - Fee Related
- 2004-12-22 DE DE602004006536T patent/DE602004006536T2/de not_active Expired - Lifetime
- 2004-12-22 BR BRPI0418328-2A patent/BRPI0418328A/pt not_active IP Right Cessation
- 2004-12-22 NZ NZ548098A patent/NZ548098A/en not_active IP Right Cessation
- 2004-12-22 JP JP2006547394A patent/JP4758909B2/ja not_active Expired - Fee Related
- 2004-12-22 CN CN200480042106A patent/CN100582108C/zh not_active Expired - Fee Related
- 2004-12-22 WO PCT/US2004/043402 patent/WO2005066177A1/en not_active Ceased
- 2004-12-22 KR KR1020067013219A patent/KR20060110344A/ko not_active Ceased
- 2004-12-22 PL PL380764A patent/PL380764A1/pl not_active Application Discontinuation
- 2004-12-22 EP EP04815474A patent/EP1699799B1/en not_active Expired - Lifetime
-
2006
- 2006-06-27 ZA ZA200605299A patent/ZA200605299B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004312506B2 (en) | 2011-08-04 |
| KR20060110344A (ko) | 2006-10-24 |
| AU2004312506A1 (en) | 2005-07-21 |
| EP1699799B1 (en) | 2007-05-16 |
| US7759349B2 (en) | 2010-07-20 |
| CN100582108C (zh) | 2010-01-20 |
| ZA200605299B (en) | 2007-03-28 |
| EP1699799A1 (en) | 2006-09-13 |
| PL380764A1 (pl) | 2007-03-19 |
| WO2005066177A1 (en) | 2005-07-21 |
| CN1922181A (zh) | 2007-02-28 |
| JP2007517043A (ja) | 2007-06-28 |
| DE602004006536T2 (de) | 2008-01-31 |
| US20050182059A1 (en) | 2005-08-18 |
| HK1091207A1 (en) | 2007-01-12 |
| ATE362475T1 (de) | 2007-06-15 |
| CA2551867C (en) | 2010-08-17 |
| DE602004006536D1 (de) | 2007-06-28 |
| BRPI0418328A (pt) | 2007-05-02 |
| JP4758909B2 (ja) | 2011-08-31 |
| CA2551867A1 (en) | 2005-07-21 |
| NZ548098A (en) | 2010-05-28 |
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