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WO2009063910A1 - Method for catalytic asymmetric synthesis of optically active isoxazoline compound - Google Patents

Method for catalytic asymmetric synthesis of optically active isoxazoline compound Download PDF

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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
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.)
Ceased
Application number
PCT/JP2008/070597
Other languages
French (fr)
Japanese (ja)
Inventor
Kazutaka Matoba
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nissan Chemical Corp
Original Assignee
Nissan Chemical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to JP2009541157A priority Critical patent/JP5365807B2/en
Publication of WO2009063910A1 publication Critical patent/WO2009063910A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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.
PCT/JP2008/070597 2007-11-12 2008-11-12 Method for catalytic asymmetric synthesis of optically active isoxazoline compound Ceased WO2009063910A1 (en)

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 Ceased 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 (34)

* Cited by examiner, † Cited by third party
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
WO2011154434A2 (en) 2010-06-09 2011-12-15 Syngenta Participations Ag Pesticidal mixtures including isoxazoline derivatives
WO2011154433A2 (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
CN117186023A (en) * 2023-09-18 2023-12-08 河北圣雪大成制药有限责任公司 A kind of preparation method of high-purity Frellana
US12497370B2 (en) 2019-12-18 2025-12-16 Elanco Tiergesundheit Ag Isoxazoline derivatives

Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1975149B1 (en) * 2005-12-26 2012-02-15 Nissan Chemical Industries, Ltd. 1,3-bis(substituted phenyl)-3-hydroxypropan-1-one or 2-propen-1-one compound, and salt thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 (53)

* Cited by examiner, † Cited by third party
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 The method for preparing isoxazoline derivatives
CN102822168B (en) * 2010-02-25 2016-10-26 先正达参股股份有限公司 The method for preparing isoxazoline derivatives
WO2011104089A1 (en) * 2010-02-25 2011-09-01 Syngenta Participations Ag Process for the preparation of isoxazoline derivatives
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
WO2011154434A2 (en) 2010-06-09 2011-12-15 Syngenta Participations Ag Pesticidal mixtures including isoxazoline derivatives
WO2011154433A2 (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
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
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
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
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
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
US10342234B2 (en) 2015-01-16 2019-07-09 Avista Pharma Solutions, Inc. Antiparasitic compounds
US9420793B2 (en) 2015-01-16 2016-08-23 Avista Pharma Solutions Antiparasitic compounds
US9686991B2 (en) 2015-01-16 2017-06-27 Avista Pharma Solutions, Inc. Antiparasitic compounds
US9883674B2 (en) 2015-01-16 2018-02-06 Avista Pharma Solutions, Inc. Antiparasitic compounds
US10092001B2 (en) 2015-01-16 2018-10-09 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
US10750744B2 (en) 2016-04-06 2020-08-25 Boehringer Ingelheim Animal Health USA 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
WO2019091936A1 (en) 2017-11-07 2019-05-16 Intervet International B.V. Injectable isoxazoline pharmaceutical compositions and their use against parasite infestation
WO2019091940A1 (en) 2017-11-07 2019-05-16 Intervet International B.V. Process for preparing large size isoxazoline particles
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
US12497370B2 (en) 2019-12-18 2025-12-16 Elanco Tiergesundheit Ag Isoxazoline derivatives
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
CN117186023A (en) * 2023-09-18 2023-12-08 河北圣雪大成制药有限责任公司 A kind of preparation method of high-purity Frellana

Also Published As

Publication number Publication date
JPWO2009063910A1 (en) 2011-03-31
JP5365807B2 (en) 2013-12-11

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