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 (enExample) | 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 (enExample) |
| EP (1) | EP2683713B1 (enExample) |
| JP (1) | JP2014507459A (enExample) |
| CN (1) | CN103502246A (enExample) |
| AR (1) | AR085657A1 (enExample) |
| AU (1) | AU2012224521B2 (enExample) |
| BR (1) | BR112013022755A2 (enExample) |
| CA (1) | CA2829149A1 (enExample) |
| CL (1) | CL2013002472A1 (enExample) |
| CO (1) | CO6801794A2 (enExample) |
| ES (1) | ES2542409T3 (enExample) |
| MX (1) | MX2013010297A (enExample) |
| RU (1) | RU2013145304A (enExample) |
| WO (1) | WO2012120135A1 (enExample) |
| ZA (1) | ZA201306175B (enExample) |
Families Citing this family (37)
| 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 |
| MD4577C1 (ro) | 2012-02-06 | 2019-02-28 | Merial Inc. | Compoziţii masticabile de uz veterinar care conţin agent activ izoxazolinic şi utilizarea acestora în tratamentul sau prevenirea unei infestări sau infecţii parazitare |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| PT2953942T (pt) | 2013-02-06 | 2018-01-17 | Bayer Cropscience Ag | Derivados de pirazol substituídos com halogéneo como agentes pesticidas |
| JP2016523871A (ja) * | 2013-06-24 | 2016-08-12 | メリアル インコーポレイテッド | 殺有害生物剤としてのチオフェン又はフラン置換イソチアゾリン化合物 |
| 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 |
| ES2905848T3 (es) | 2013-11-01 | 2022-04-12 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de isoxazolina antiparasitarios y plaguicidas |
| TW201540705A (zh) | 2014-01-03 | 2015-11-01 | 拜耳作物科學股份有限公司 | 做為殺蟲劑之新穎吡唑基雜芳基醯胺類 |
| ES2765405T3 (es) | 2014-04-17 | 2020-06-09 | Boehringer Ingelheim Animal Health Usa Inc | Utilización de compuestos de malononitrilo para proteger animales de parásitos |
| AU2015289246B2 (en) | 2014-07-15 | 2019-07-25 | Elanco Animal Health Gmbh | Aryl-triazolyl pyridines as pest control agents |
| EP3207008B1 (en) | 2014-10-14 | 2018-07-25 | Syngenta Participations AG | Process for the preparation of 5-bromo-1,2,3-trichlorobenzene |
| JP6686012B2 (ja) | 2014-10-14 | 2020-04-22 | シンジェンタ パーティシペーションズ アーゲー | ハロ置換トリフルオロアセトフェノンを調製する方法 |
| BR112017007506B1 (pt) | 2014-10-14 | 2021-02-02 | Syngenta Participations Ag | processo para a preparação de 1-(3,5-diclorofenil)-2,2,2-trifluoroetanona e seus derivados |
| CN117550960A (zh) * | 2014-10-14 | 2024-02-13 | 先正达参股股份有限公司 | 用于制备1-(3,5-二氯-4-氟-苯基)-2,2,2-三氟-乙酮的方法 |
| 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 |
| JP6824900B2 (ja) * | 2015-04-08 | 2021-02-03 | ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド | イソオキサゾリン活性薬剤を含む延長放出注射製剤、方法及びその使用 |
| CN107835818B (zh) | 2015-05-20 | 2022-04-29 | 勃林格殷格翰动物保健美国公司 | 驱虫缩酚酸肽化合物 |
| 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 |
| BR112019007605A2 (pt) | 2016-10-14 | 2019-09-17 | Boehringer Ingelheim Animal Health Usa Inc | compostos pesticidas e parasiticidas de vinil isoxazolina |
| WO2018093920A1 (en) | 2016-11-16 | 2018-05-24 | Merial, Inc. | Anthelmintic depsipeptide compounds |
| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| ES2944616T3 (es) | 2017-08-14 | 2023-06-22 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de pirazol-isoxazolina plaguicidas y parasiticidas |
| KR102785432B1 (ko) | 2018-07-09 | 2025-03-21 | 베링거잉겔하임베트메디카게엠베하 | 구충성 헤테로시클릭 화합물 |
| US11773066B2 (en) | 2018-11-20 | 2023-10-03 | Boehringer Ingelheim Animal Health USA Inc. | Indazolylcyanoethylamino compound, compositions of same, method of making, and methods of using thereof |
| US11560388B2 (en) | 2019-03-19 | 2023-01-24 | Boehringer Ingelheim Vetmedica Gmbh | 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 |
| JP2023509452A (ja) | 2020-01-03 | 2023-03-08 | バーグ エルエルシー | がんを処置するためのｕｂｅ２ｋモジュレータとしての多環式アミド |
| 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 |
| MX2022015038A (es) | 2020-05-29 | 2023-01-04 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos heterociclicos como anthelminticos. |
| WO2022140728A1 (en) | 2020-12-21 | 2022-06-30 | Boehringer Ingelheim Animam Health Usa Inc. | Parasiticidal collar comprising isoxazoline compounds |
| WO2022162016A1 (en) | 2021-01-27 | 2022-08-04 | Intervet International B.V. | Cyclopropylamide compounds against parasites in fish |
| US20240116854A1 (en) | 2021-01-27 | 2024-04-11 | Intervet Inc. | Cyclopropylamide compounds against parasites in fish |
| 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 |
| US20260021076A1 (en) | 2024-07-22 | 2026-01-22 | Zoetis Services Llc | Isoxazoline and macrocyclic lactone microspheres |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101331127B (zh) * | 2005-12-16 | 2012-05-23 | 杜邦公司 | 用于防治无脊椎害虫的5-芳基异噁唑啉 |
| 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 |
| BRPI0707091B8 (pt) * | 2006-03-10 | 2018-02-14 | Nissan Chemical Ind Ltd | composto de isoxalina e benzaldoxima substituído ou um sal do mesmo; pesticida, agroquímico, endo- ou ecto-parasiticidapara mamíferos ou pássaros, inseticida e acaricida contendo como um ou mais ingredientes ativos selecionados a partir do composto de isoxalina substituído e o sal do mesmo |
| WO2008122375A2 (en) * | 2007-04-10 | 2008-10-16 | 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 |
| WO2010070068A2 (en) | 2008-12-19 | 2010-06-24 | Novartis Ag | Organic compounds |
| 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 RU RU2013145304/04A patent/RU2013145304A/ru not_active Application Discontinuation
- 2012-03-09 CA CA2829149A patent/CA2829149A1/en not_active Abandoned
- 2012-03-09 CN CN201280012748.2A patent/CN103502246A/zh active Pending
- 2012-03-09 BR BR112013022755A patent/BR112013022755A2/pt not_active IP Right Cessation
- 2012-03-09 WO PCT/EP2012/054161 patent/WO2012120135A1/en not_active Ceased
- 2012-03-09 US US14/004,307 patent/US8822466B2/en not_active Expired - Fee Related
- 2012-03-09 AR ARP120100793A patent/AR085657A1/es unknown
- 2012-03-09 MX MX2013010297A patent/MX2013010297A/es not_active Application Discontinuation
- 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 JP JP2013557121A patent/JP2014507459A/ja active Pending
- 2012-03-09 AU AU2012224521A patent/AU2012224521B2/en not_active Expired - Fee Related
-
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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