WO2009063910A1 - Method for catalytic asymmetric synthesis of optically active isoxazoline compound - Google Patents
Method for catalytic asymmetric synthesis of optically active isoxazoline compound Download PDFInfo
- Publication number
- WO2009063910A1 WO2009063910A1 PCT/JP2008/070597 JP2008070597W WO2009063910A1 WO 2009063910 A1 WO2009063910 A1 WO 2009063910A1 JP 2008070597 W JP2008070597 W JP 2008070597W WO 2009063910 A1 WO2009063910 A1 WO 2009063910A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- asymmetric synthesis
- optically active
- isoxazoline compound
- catalytic asymmetric
- active isoxazoline
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Disclosed is a novel method for asymmetric synthesis of an intermediate of a pest control agent. Specifically disclosed is a method for catalytic asymmetric synthesis of an optically active isoxazoline compound represented by the formula (2) below, which is performed by reacting an α,β-unsaturated carbonyl compound represented by the formula (1) below with a hydroxyl amine, in a solvent in the presence of a base and water, by adding a chiral phase-transfer catalyst.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009541157A JP5365807B2 (en) | 2007-11-12 | 2008-11-12 | Catalytic asymmetric synthesis of optically active isoxazoline compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007-293168 | 2007-11-12 | ||
JP2007293168 | 2007-11-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009063910A1 true WO2009063910A1 (en) | 2009-05-22 |
Family
ID=40638759
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2008/070597 WO2009063910A1 (en) | 2007-11-12 | 2008-11-12 | Method for catalytic asymmetric synthesis of optically active isoxazoline compound |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP5365807B2 (en) |
WO (1) | WO2009063910A1 (en) |
Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011051977A (en) * | 2009-08-03 | 2011-03-17 | Nissan Chem Ind Ltd | Optically-active substance and diastereomer salt of dihydroisoxazole-substituted benzoic acid compound, and method for producing the same |
WO2011101402A1 (en) | 2010-02-17 | 2011-08-25 | Syngenta Participations Ag | Isoxazoline derivatives as insecticides |
WO2011104089A1 (en) * | 2010-02-25 | 2011-09-01 | Syngenta Participations Ag | Process for the preparation of isoxazoline derivatives |
GB2481118A (en) * | 2010-06-09 | 2011-12-14 | Syngenta Participations Ag | Pesticidal mixtures comprising enantiomerically enriched isoxazoline derivatives |
WO2011154433A2 (en) | 2010-06-09 | 2011-12-15 | Syngenta Participations Ag | Pesticidal mixtures including isoxazoline derivatives |
WO2011154434A2 (en) | 2010-06-09 | 2011-12-15 | Syngenta Participations Ag | Pesticidal mixtures including isoxazoline derivatives |
WO2012007426A1 (en) | 2010-07-13 | 2012-01-19 | Basf Se | Azoline substituted isoxazoline benzamide compounds for combating animal pests |
WO2012120399A1 (en) | 2011-03-10 | 2012-09-13 | Pfizer Inc. | Spirocyclic isoxazoline derivatives as antiparasitic agents |
GB2491594A (en) * | 2010-06-09 | 2012-12-12 | Syngenta Participations Ag | Pesticidal mixtures comprising enantiomerically enriched isoxazoline derivatives |
WO2013021949A1 (en) * | 2011-08-05 | 2013-02-14 | 日産化学工業株式会社 | Method for producing substituted 4,4-difluoro-2-buten-1-one compound and method for producing substituted isoxazoline compound |
WO2013069731A1 (en) * | 2011-11-08 | 2013-05-16 | 日産化学工業株式会社 | Method for catalytic asymmetric synthesis of optically active isoxazoline compound, and optically active isoxazoline compound |
WO2013116236A1 (en) | 2012-02-03 | 2013-08-08 | Zoetis Llc | Process for the preparation of chiral isoxazoline azetidine derivatives as antiparasitic agents |
US8686014B2 (en) | 2008-09-04 | 2014-04-01 | Syngenta Limited | Insecticidal compounds |
JP2014517837A (en) * | 2011-05-18 | 2014-07-24 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | Insecticidal compounds based on arylthioacetamide derivatives |
US8822502B2 (en) | 2008-08-22 | 2014-09-02 | Syngenta Crop Protection Llc | Insecticidal compounds |
US8853410B2 (en) | 2009-04-30 | 2014-10-07 | Basf Se | Process for preparing substituted isoxazoline compounds and their precursors |
WO2014192841A1 (en) * | 2013-05-27 | 2014-12-04 | 住友化学株式会社 | Method for producing optically active isoxazoline compound |
US9006447B2 (en) | 2010-11-03 | 2015-04-14 | Basf Se | Method for preparing substituted isoxazoline compounds and their precursors 4-chloro, 4-bromo- or 4-iodobenzaldehyde oximes |
US9062010B2 (en) | 2013-06-27 | 2015-06-23 | Nissan Chemical Industries, Ltd. | Crystalline polymorphs of isoxazoline compound and production method thereof |
US9085541B2 (en) | 2010-06-23 | 2015-07-21 | Basf Se | Process for producing imine compounds for combating invertebrate pests |
US9216973B2 (en) | 2008-08-22 | 2015-12-22 | Syngenta Participations Ag | Insecticidal compounds |
US9420793B2 (en) | 2015-01-16 | 2016-08-23 | Avista Pharma Solutions | Antiparasitic compounds |
WO2019091940A1 (en) | 2017-11-07 | 2019-05-16 | Intervet International B.V. | Process for preparing large size isoxazoline particles |
WO2019091936A1 (en) | 2017-11-07 | 2019-05-16 | Intervet International B.V. | Injectable isoxazoline pharmaceutical compositions and their use against parasite infestation |
WO2019115492A1 (en) | 2017-12-12 | 2019-06-20 | Intervet International B.V. | Implantable isoxazoline pharmaceutical compositions and uses thereof |
US10433552B2 (en) | 2016-04-06 | 2019-10-08 | Merial, Inc. | Process for the preparation of isoxazoline compounds |
WO2020094434A1 (en) | 2018-11-06 | 2020-05-14 | Basf Se | Process for preparation of optically enriched isoxazolines |
US10807992B2 (en) | 2017-11-16 | 2020-10-20 | Avista Pharma Solutions, Inc. | Single enantiomer antiparasitic compounds |
WO2020225143A1 (en) | 2019-05-03 | 2020-11-12 | Intervet International B.V. | Injectable pharmaceutical compositions and uses thereof |
WO2021197880A1 (en) | 2020-03-31 | 2021-10-07 | Basf Se | Process for preparation of optically enriched isoxazolines |
WO2021228673A1 (en) | 2020-05-13 | 2021-11-18 | Basf Se | Process for preparation of optically enriched isoxazolines |
WO2021233967A1 (en) | 2020-05-20 | 2021-11-25 | Intervet International B.V. | Injectable pharmaceutical compositions and uses thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004018410A1 (en) * | 2002-08-26 | 2004-03-04 | Nissan Chemical Industries, Ltd. | Substituted benzanilide compound and pest control agent |
WO2005085216A1 (en) * | 2004-03-05 | 2005-09-15 | Nissan Chemical Industries, Ltd. | Isoxazoline-substituted benzamide compound and noxious organism control agent |
JP2005272452A (en) * | 2004-02-23 | 2005-10-06 | Nissan Chem Ind Ltd | Substituted benzanilide compound and pesticide |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5304981B2 (en) * | 2005-12-26 | 2013-10-02 | 日産化学工業株式会社 | 1,3-bis (substituted phenyl) -3-hydroxypropan-1-one and 2-propen-1-one compounds and salts thereof |
-
2008
- 2008-11-12 JP JP2009541157A patent/JP5365807B2/en active Active
- 2008-11-12 WO PCT/JP2008/070597 patent/WO2009063910A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004018410A1 (en) * | 2002-08-26 | 2004-03-04 | Nissan Chemical Industries, Ltd. | Substituted benzanilide compound and pest control agent |
JP2005272452A (en) * | 2004-02-23 | 2005-10-06 | Nissan Chem Ind Ltd | Substituted benzanilide compound and pesticide |
WO2005085216A1 (en) * | 2004-03-05 | 2005-09-15 | Nissan Chemical Industries, Ltd. | Isoxazoline-substituted benzamide compound and noxious organism control agent |
Non-Patent Citations (1)
Title |
---|
DIGHADE, S. R. ET AL.: "Synthesis of some new 3-(2-hydroxy-5-methylphenyl)-5,5-dialkyl/5, 5-diaryl/5-arylisoxazolines", ORIENTAL JOURNAL OF CHEMISTRY, vol. 17, no. 3, 2001, pages 505 - 508 * |
Cited By (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9216973B2 (en) | 2008-08-22 | 2015-12-22 | Syngenta Participations Ag | Insecticidal compounds |
US8822502B2 (en) | 2008-08-22 | 2014-09-02 | Syngenta Crop Protection Llc | Insecticidal compounds |
US9282742B2 (en) | 2008-09-04 | 2016-03-15 | Syngenta Participations Ag | Insecticidal compounds |
US8686014B2 (en) | 2008-09-04 | 2014-04-01 | Syngenta Limited | Insecticidal compounds |
US8853410B2 (en) | 2009-04-30 | 2014-10-07 | Basf Se | Process for preparing substituted isoxazoline compounds and their precursors |
JP2011051977A (en) * | 2009-08-03 | 2011-03-17 | Nissan Chem Ind Ltd | Optically-active substance and diastereomer salt of dihydroisoxazole-substituted benzoic acid compound, and method for producing the same |
WO2011101402A1 (en) | 2010-02-17 | 2011-08-25 | Syngenta Participations Ag | Isoxazoline derivatives as insecticides |
JP2013520456A (en) * | 2010-02-25 | 2013-06-06 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | Method for producing isoxazoline derivative |
CN102822168A (en) * | 2010-02-25 | 2012-12-12 | 先正达参股股份有限公司 | Process for the preparation of isoxazoline derivatives |
WO2011104089A1 (en) * | 2010-02-25 | 2011-09-01 | Syngenta Participations Ag | Process for the preparation of isoxazoline derivatives |
CN102822168B (en) * | 2010-02-25 | 2016-10-26 | 先正达参股股份有限公司 | The method preparing isoxazoline derivant |
GB2491594A (en) * | 2010-06-09 | 2012-12-12 | Syngenta Participations Ag | Pesticidal mixtures comprising enantiomerically enriched isoxazoline derivatives |
GB2481118A (en) * | 2010-06-09 | 2011-12-14 | Syngenta Participations Ag | Pesticidal mixtures comprising enantiomerically enriched isoxazoline derivatives |
WO2011154433A2 (en) | 2010-06-09 | 2011-12-15 | Syngenta Participations Ag | Pesticidal mixtures including isoxazoline derivatives |
WO2011154434A2 (en) | 2010-06-09 | 2011-12-15 | Syngenta Participations Ag | Pesticidal mixtures including isoxazoline derivatives |
US9085541B2 (en) | 2010-06-23 | 2015-07-21 | Basf Se | Process for producing imine compounds for combating invertebrate pests |
WO2012007426A1 (en) | 2010-07-13 | 2012-01-19 | Basf Se | Azoline substituted isoxazoline benzamide compounds for combating animal pests |
US9006447B2 (en) | 2010-11-03 | 2015-04-14 | Basf Se | Method for preparing substituted isoxazoline compounds and their precursors 4-chloro, 4-bromo- or 4-iodobenzaldehyde oximes |
CN103517907A (en) * | 2011-03-10 | 2014-01-15 | 佐蒂斯有限责任公司 | Spirocyclic isoxazoline derivatives as antiparasitic agents |
WO2012120399A1 (en) | 2011-03-10 | 2012-09-13 | Pfizer Inc. | Spirocyclic isoxazoline derivatives as antiparasitic agents |
US8466115B2 (en) | 2011-03-10 | 2013-06-18 | Zoetis Llc | Spirocyclic isoxazoline derivatives as antiparasitic agents |
JP2014517837A (en) * | 2011-05-18 | 2014-07-24 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | Insecticidal compounds based on arylthioacetamide derivatives |
JPWO2013021949A1 (en) * | 2011-08-05 | 2015-03-05 | 日産化学工業株式会社 | Process for producing substituted 4,4-difluoro-2-buten-1-one compound and substituted isoxazoline compound |
WO2013021949A1 (en) * | 2011-08-05 | 2013-02-14 | 日産化学工業株式会社 | Method for producing substituted 4,4-difluoro-2-buten-1-one compound and method for producing substituted isoxazoline compound |
JPWO2013069731A1 (en) * | 2011-11-08 | 2015-04-02 | 日産化学工業株式会社 | Catalytic asymmetric synthesis method of optically active isoxazoline compound and optically active isoxazoline compound |
WO2013069731A1 (en) * | 2011-11-08 | 2013-05-16 | 日産化学工業株式会社 | Method for catalytic asymmetric synthesis of optically active isoxazoline compound, and optically active isoxazoline compound |
US9126995B2 (en) | 2011-11-08 | 2015-09-08 | Nissan Chemical Industries, Ltd. | Method for catalytic asymmetric synthesis of optically active isoxazoline compound and optically active isoxazoline compound |
US20140350261A1 (en) * | 2011-11-08 | 2014-11-27 | Nissan Chemical Industries, Ltd. | Method for catalytic asymmetric synthesis of optically active isoxazoline compound, and optically active isoxazoline compound |
WO2013116236A1 (en) | 2012-02-03 | 2013-08-08 | Zoetis Llc | Process for the preparation of chiral isoxazoline azetidine derivatives as antiparasitic agents |
WO2014192841A1 (en) * | 2013-05-27 | 2014-12-04 | 住友化学株式会社 | Method for producing optically active isoxazoline compound |
US9062010B2 (en) | 2013-06-27 | 2015-06-23 | Nissan Chemical Industries, Ltd. | Crystalline polymorphs of isoxazoline compound and production method thereof |
US9883674B2 (en) | 2015-01-16 | 2018-02-06 | Avista Pharma Solutions, Inc. | Antiparasitic compounds |
US9686991B2 (en) | 2015-01-16 | 2017-06-27 | Avista Pharma Solutions, Inc. | Antiparasitic compounds |
US9420793B2 (en) | 2015-01-16 | 2016-08-23 | Avista Pharma Solutions | Antiparasitic compounds |
US10092001B2 (en) | 2015-01-16 | 2018-10-09 | Avista Pharma Solutions, Inc. | Antiparasitic compounds |
US10342234B2 (en) | 2015-01-16 | 2019-07-09 | Avista Pharma Solutions, Inc. | Antiparasitic compounds |
US10772331B2 (en) | 2015-01-16 | 2020-09-15 | Avista Pharma Solutions, Inc. | Antiparasitic compounds |
US10433552B2 (en) | 2016-04-06 | 2019-10-08 | Merial, Inc. | Process for the preparation of isoxazoline compounds |
US11324220B2 (en) | 2016-04-06 | 2022-05-10 | Boehringer Ingelheim Animal Health USA Inc. | Process for the preparation of isoxazoline compounds |
US10750744B2 (en) | 2016-04-06 | 2020-08-25 | Boehringer Ingelheim Animal Health USA Inc. | Process for the preparation of isoxazoline compounds |
WO2019091940A1 (en) | 2017-11-07 | 2019-05-16 | Intervet International B.V. | Process for preparing large size isoxazoline particles |
WO2019091936A1 (en) | 2017-11-07 | 2019-05-16 | Intervet International B.V. | Injectable isoxazoline pharmaceutical compositions and their use against parasite infestation |
EP4316522A2 (en) | 2017-11-07 | 2024-02-07 | Intervet International B.V. | Injectable isoxazoline pharmaceutical compositions and their use against parasite infestation |
US10807992B2 (en) | 2017-11-16 | 2020-10-20 | Avista Pharma Solutions, Inc. | Single enantiomer antiparasitic compounds |
WO2019115492A1 (en) | 2017-12-12 | 2019-06-20 | Intervet International B.V. | Implantable isoxazoline pharmaceutical compositions and uses thereof |
US20210380569A1 (en) * | 2018-11-06 | 2021-12-09 | Basf Se | Process for Preparation of Optically Enriched Isoxazolines |
WO2020094434A1 (en) | 2018-11-06 | 2020-05-14 | Basf Se | Process for preparation of optically enriched isoxazolines |
WO2020225143A1 (en) | 2019-05-03 | 2020-11-12 | Intervet International B.V. | Injectable pharmaceutical compositions and uses thereof |
WO2021197880A1 (en) | 2020-03-31 | 2021-10-07 | Basf Se | Process for preparation of optically enriched isoxazolines |
WO2021228673A1 (en) | 2020-05-13 | 2021-11-18 | Basf Se | Process for preparation of optically enriched isoxazolines |
WO2021233967A1 (en) | 2020-05-20 | 2021-11-25 | Intervet International B.V. | Injectable pharmaceutical compositions and uses thereof |
Also Published As
Publication number | Publication date |
---|---|
JP5365807B2 (en) | 2013-12-11 |
JPWO2009063910A1 (en) | 2011-03-31 |
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