JP2014507459A5 - - Google Patents
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- JP2014507459A5 JP2014507459A5 JP2013557121A JP2013557121A JP2014507459A5 JP 2014507459 A5 JP2014507459 A5 JP 2014507459A5 JP 2013557121 A JP2013557121 A JP 2013557121A JP 2013557121 A JP2013557121 A JP 2013557121A JP 2014507459 A5 JP2014507459 A5 JP 2014507459A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- haloalkyl
- alkoxy
- unsubstituted
- substituted
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- -1 amino - Chemical class 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- BOTREHHXSQGWTR-UHFFFAOYSA-N oxolane-3-carboxylic acid Chemical compound OC(=O)C1CCOC1 BOTREHHXSQGWTR-UHFFFAOYSA-N 0.000 claims 2
- 244000045947 parasite Species 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 2
- 125000005458 thianyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical group C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims 1
- YJEMQUPUTXKLMX-UHFFFAOYSA-N N-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]thiophen-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1SC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 YJEMQUPUTXKLMX-UHFFFAOYSA-N 0.000 claims 1
- HRVNBQRGLQRTMT-UHFFFAOYSA-N N-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]thiophen-3-yl]methyl]propanamide Chemical compound S1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C1 HRVNBQRGLQRTMT-UHFFFAOYSA-N 0.000 claims 1
- RHRVWNITRNKWCH-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylfuran-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1OC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 RHRVWNITRNKWCH-UHFFFAOYSA-N 0.000 claims 1
- LTOSPMAKMXIYDK-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylfuran-3-yl]methyl]oxolane-3-carboxamide Chemical compound CC=1OC(=CC1CNC(=O)C1COCC1)C1=NOC(C1)(C(F)(F)F)C1=CC(=CC(=C1)Cl)Cl LTOSPMAKMXIYDK-UHFFFAOYSA-N 0.000 claims 1
- OXIPEMXHAXUIDL-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylthiophen-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1SC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 OXIPEMXHAXUIDL-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- WFBFJMNWFUCZMJ-UHFFFAOYSA-N n-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1OC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 WFBFJMNWFUCZMJ-UHFFFAOYSA-N 0.000 claims 1
- ZPJVAIQVKUCRBP-UHFFFAOYSA-N n-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-yl]methyl]oxolane-3-carboxamide Chemical compound CC=1OC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CCOC1 ZPJVAIQVKUCRBP-UHFFFAOYSA-N 0.000 claims 1
- SLUWJSVOOWRWBS-UHFFFAOYSA-N n-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-yl]methyl]propanamide Chemical compound O1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C1 SLUWJSVOOWRWBS-UHFFFAOYSA-N 0.000 claims 1
- WUXYMHDSFCIQMA-UHFFFAOYSA-N n-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylthiophen-3-yl]methyl]propanamide Chemical compound S1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)C1 WUXYMHDSFCIQMA-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4072011 | 2011-03-10 | ||
| CH00407/11 | 2011-03-10 | ||
| PCT/EP2012/054161 WO2012120135A1 (en) | 2011-03-10 | 2012-03-09 | Isoxazole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014507459A JP2014507459A (ja) | 2014-03-27 |
| JP2014507459A5 true JP2014507459A5 (https=) | 2015-04-09 |
Family
ID=45809012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013557121A Pending JP2014507459A (ja) | 2011-03-10 | 2012-03-09 | イソオキサゾール誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8822466B2 (https=) |
| EP (1) | EP2683713B1 (https=) |
| JP (1) | JP2014507459A (https=) |
| CN (1) | CN103502246A (https=) |
| AR (1) | AR085657A1 (https=) |
| AU (1) | AU2012224521B2 (https=) |
| BR (1) | BR112013022755A2 (https=) |
| CA (1) | CA2829149A1 (https=) |
| CL (1) | CL2013002472A1 (https=) |
| CO (1) | CO6801794A2 (https=) |
| ES (1) | ES2542409T3 (https=) |
| MX (1) | MX2013010297A (https=) |
| RU (1) | RU2013145304A (https=) |
| WO (1) | WO2012120135A1 (https=) |
| ZA (1) | ZA201306175B (https=) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY33403A (es) * | 2010-06-17 | 2011-12-30 | Novartis Ag | Compuestos orgánicos con novedosas isoxazolinas, sus n-óxidos, s-óxidos y sales |
| EP3216448B8 (en) | 2012-02-06 | 2019-06-05 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| ES2656012T3 (es) | 2013-02-06 | 2018-02-22 | Bayer Cropscience Aktiengesellschaft | Derivados de pirazol sustituidos con halógeno como pesticidas |
| BR112015032324B1 (pt) * | 2013-06-24 | 2020-04-07 | Merial Inc | compostos isotiazolina-substituído de tiofeno ou furano como pesticidas |
| US9944597B2 (en) | 2013-09-16 | 2018-04-17 | The Board Of Regents Of The University Of Texas System | Polysubstituted pyrroles having microtubule-disrupting, cytotoxic and antitumor activities and methods of use thereof |
| WO2015066277A1 (en) | 2013-11-01 | 2015-05-07 | Merial Limited | Antiparisitic and pesticidal isoxazoline compounds |
| AU2014375265B2 (en) | 2014-01-03 | 2018-11-01 | Elanco Animal Health Gmbh | Novel pyrazolyl-heteroarylamides as pesticides |
| EP3131398B1 (en) | 2014-04-17 | 2019-10-23 | Boehringer Ingelheim Animal Health USA Inc. | Use of malononitrile compounds for protecting animals from parasites |
| MX2017000673A (es) | 2014-07-15 | 2017-04-27 | Bayer Animal Health Gmbh | Nueva piridina triazolil arilo como pesticida. |
| US9862937B2 (en) | 2014-10-14 | 2018-01-09 | Syngenta Participations Ag | Process for the preparation of halo-substituted trifluoroacetophenones |
| EP3207008B1 (en) | 2014-10-14 | 2018-07-25 | Syngenta Participations AG | Process for the preparation of 5-bromo-1,2,3-trichlorobenzene |
| JP6640210B2 (ja) * | 2014-10-14 | 2020-02-05 | シンジェンタ パーティシペーションズ アーゲー | １−（３，５−ジクロロ−４−フルオロ−フェニル）−２，２，２−トリフルオロ−エタノンを調製するプロセス |
| PL3207023T3 (pl) | 2014-10-14 | 2020-01-31 | Syngenta Participations Ag | Sposób wytwarzania halo-podstawionych benzenów |
| EP3018129A1 (en) * | 2014-11-10 | 2016-05-11 | Novartis Tiergesundheit AG | Diaryl isoxazoline compound |
| UY36570A (es) | 2015-02-26 | 2016-10-31 | Merial Inc | Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas |
| SG11201708068PA (en) * | 2015-04-08 | 2017-10-30 | Merial Inc | Extended release injectable formulations comprising an isoxazoline active agent, methods and uses thereof |
| LT3298027T (lt) | 2015-05-20 | 2021-08-10 | Boehringer Ingelheim Animal Health USA Inc. | Antihelmintiniai depsipeptido junginiai |
| UY37137A (es) | 2016-02-24 | 2017-09-29 | Merial Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
| WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| WO2018071535A1 (en) | 2016-10-14 | 2018-04-19 | Merial, Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
| CA3044038A1 (en) | 2016-11-16 | 2018-05-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| BR112020003217A2 (pt) | 2017-08-14 | 2020-10-06 | Boehringer Ingelheim Animal Health USA Inc. | compostos pesticidas e parasiticidas de pirazolisoxazolina |
| AU2019301510B2 (en) | 2018-07-09 | 2024-06-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anthelminthic heterocyclic compounds |
| CN113260419A (zh) | 2018-11-20 | 2021-08-13 | 勃林格殷格翰动物保健美国公司 | 吲唑基氰基乙基氨基化合物、其组合物、其制备方法和其使用方法 |
| CA3133100A1 (en) | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| AR119790A1 (es) | 2019-08-29 | 2022-01-12 | Pi Industries Ltd | Compuestos de isoxazolina y su uso como agentes para el control de plagas |
| CA3166630A1 (en) | 2020-01-03 | 2021-07-08 | Berg Llc | Polycyclic amides as ube2k modulators for treating cancer |
| AU2021278871A1 (en) | 2020-05-28 | 2023-01-19 | Boehringer Ingelheim Animal Health USA Inc. | Bi-modal release intra-ruminal capsule device and methods of use thereof |
| KR20230028268A (ko) | 2020-05-29 | 2023-02-28 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 헤테로시클릭 화합물 |
| WO2022140728A1 (en) | 2020-12-21 | 2022-06-30 | Boehringer Ingelheim Animam Health Usa Inc. | Parasiticidal collar comprising isoxazoline compounds |
| US20240116854A1 (en) | 2021-01-27 | 2024-04-11 | Intervet Inc. | Cyclopropylamide compounds against parasites in fish |
| JP7824305B2 (ja) | 2021-01-27 | 2026-03-04 | コルテバ アグリサイエンス エルエルシー | 魚における寄生生物に対するシクロプロピルアミド化合物 |
| NO20240925A1 (en) | 2023-09-15 | 2025-03-17 | Evah Atlantic Inc | Dihydroisoxazole compound for use in reducing ectoparasite infestations on fish |
| WO2025257633A1 (en) | 2024-06-12 | 2025-12-18 | Boehringer Ingelheim Vetmedica Gmbh | Long-acting castor oil-containing injectable formulations and methods of use thereof |
| WO2026024600A1 (en) | 2024-07-22 | 2026-01-29 | Zoetis Services Llc | Isoxazoline and macrocyclic lactone microspheres |
| WO2026043852A1 (en) | 2024-08-20 | 2026-02-26 | Zoetis Services Llc | Process for preparing optically enriched isoxazolines |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200804080B (en) * | 2005-12-16 | 2009-10-28 | Du Pont | 5-Aryl isoxazolines for controlling invertebrate pests |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| TWI412322B (zh) * | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| WO2007105814A1 (ja) * | 2006-03-10 | 2007-09-20 | Nissan Chemical Industries, Ltd. | 置換イソキサゾリン化合物及び有害生物防除剤 |
| MY146638A (en) * | 2007-04-10 | 2012-09-14 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
| TWI600639B (zh) | 2007-08-17 | 2017-10-01 | 杜邦股份有限公司 | 製備５-鹵烷基-４，５-二氫異唑衍生物之化合物 |
| WO2009071500A2 (en) | 2007-12-03 | 2009-06-11 | Novartis Ag | Organic compounds |
| HUE015568T4 (en) * | 2008-12-19 | 2017-10-30 | Elanco Tiergesundheit Ag | Isoxazoline derivatives and their use as pesticides |
| JP2010235590A (ja) * | 2009-03-09 | 2010-10-21 | Nissan Chem Ind Ltd | 置換イソキサゾリン化合物及び有害生物防除剤 |
| UY33403A (es) | 2010-06-17 | 2011-12-30 | Novartis Ag | Compuestos orgánicos con novedosas isoxazolinas, sus n-óxidos, s-óxidos y sales |
-
2012
- 2012-03-09 WO PCT/EP2012/054161 patent/WO2012120135A1/en not_active Ceased
- 2012-03-09 AR ARP120100793A patent/AR085657A1/es unknown
- 2012-03-09 EP EP20120707629 patent/EP2683713B1/en not_active Not-in-force
- 2012-03-09 ES ES12707629.7T patent/ES2542409T3/es active Active
- 2012-03-09 US US14/004,307 patent/US8822466B2/en not_active Expired - Fee Related
- 2012-03-09 BR BR112013022755A patent/BR112013022755A2/pt not_active IP Right Cessation
- 2012-03-09 JP JP2013557121A patent/JP2014507459A/ja active Pending
- 2012-03-09 CA CA2829149A patent/CA2829149A1/en not_active Abandoned
- 2012-03-09 AU AU2012224521A patent/AU2012224521B2/en not_active Expired - Fee Related
- 2012-03-09 MX MX2013010297A patent/MX2013010297A/es not_active Application Discontinuation
- 2012-03-09 CN CN201280012748.2A patent/CN103502246A/zh active Pending
- 2012-03-09 RU RU2013145304/04A patent/RU2013145304A/ru not_active Application Discontinuation
-
2013
- 2013-08-16 ZA ZA2013/06175A patent/ZA201306175B/en unknown
- 2013-08-21 CO CO13198103A patent/CO6801794A2/es active IP Right Grant
- 2013-08-27 CL CL2013002472A patent/CL2013002472A1/es unknown
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