WO2009063910A1 - 光学活性イソキサゾリン化合物の触媒的不斉合成方法 - Google Patents

光学活性イソキサゾリン化合物の触媒的不斉合成方法 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
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WO
WIPO (PCT)
Prior art keywords
asymmetric synthesis
optically active
isoxazoline compound
catalytic asymmetric
active isoxazoline
Prior art date
Application number
PCT/JP2008/070597
Other languages
English (en)
French (fr)
Inventor
Kazutaka Matoba
Original Assignee
Nissan Chemical Industries, Ltd.
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 Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to JP2009541157A priority Critical patent/JP5365807B2/ja
Publication of WO2009063910A1 publication Critical patent/WO2009063910A1/ja

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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

Abstract

【課題】　有害生物防除剤の中間体の新規な不斉合成法を提供する。 【解決手段】 式（１）で表されるα、β－不飽和カルボニル化合物とヒドロキシルアミンとを、溶媒中、塩基及び水の存在下でキラル相間移動触媒を加えて反応させることによる式（２）で表される光学活性イソキサゾリン化合物の触媒的不斉合成方法。
PCT/JP2008/070597 2007-11-12 2008-11-12 光学活性イソキサゾリン化合物の触媒的不斉合成方法 WO2009063910A1 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2009541157A JP5365807B2 (ja) 2007-11-12 2008-11-12 光学活性イソキサゾリン化合物の触媒的不斉合成方法

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 (ja) 2009-05-22

Family

ID=40638759

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/070597 WO2009063910A1 (ja) 2007-11-12 2008-11-12 光学活性イソキサゾリン化合物の触媒的不斉合成方法

Country Status (2)

Country Link
JP (1) JP5365807B2 (ja)
WO (1) WO2009063910A1 (ja)

Cited By (32)

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Publication number Priority date Publication date Assignee Title
JP2011051977A (ja) * 2009-08-03 2011-03-17 Nissan Chem Ind Ltd ジヒドロイソキサゾール置換安息香酸化合物の光学活性体とジアステレオマー塩及びその製造方法
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 (ja) * 2011-08-05 2013-02-14 日産化学工業株式会社 置換４，４－ジフルオロ－２－ブテン－１－オン化合物及び置換イソキサゾリン化合物の製造方法
WO2013069731A1 (ja) * 2011-11-08 2013-05-16 日産化学工業株式会社 光学活性イソキサゾリン化合物の触媒的不斉合成方法及び光学活性イソキサゾリン化合物
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 (ja) * 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 アリールチオアセトアミド誘導体をベースとする殺虫化合物
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 (ja) * 2013-05-27 2014-12-04 住友化学株式会社 光学活性なイソキサゾリン化合物の製造方法
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
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
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004018410A1 (ja) * 2002-08-26 2004-03-04 Nissan Chemical Industries, Ltd. 置換ベンズアニリド化合物及び有害生物防除剤
WO2005085216A1 (ja) * 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤
JP2005272452A (ja) * 2004-02-23 2005-10-06 Nissan Chem Ind Ltd 置換ベンズアニリド化合物及び有害生物防除剤

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007074789A1 (ja) * 2005-12-26 2007-07-05 Nissan Chemical Industries, Ltd. １，３－ビス（置換フェニル）－３－ヒドロキシプロパン－１－オンおよび２－プロペン－１－オン化合物およびその塩

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004018410A1 (ja) * 2002-08-26 2004-03-04 Nissan Chemical Industries, Ltd. 置換ベンズアニリド化合物及び有害生物防除剤
JP2005272452A (ja) * 2004-02-23 2005-10-06 Nissan Chem Ind Ltd 置換ベンズアニリド化合物及び有害生物防除剤
WO2005085216A1 (ja) * 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤

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 (51)

* 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 (ja) * 2009-08-03 2011-03-17 Nissan Chem Ind Ltd ジヒドロイソキサゾール置換安息香酸化合物の光学活性体とジアステレオマー塩及びその製造方法
WO2011101402A1 (en) 2010-02-17 2011-08-25 Syngenta Participations Ag Isoxazoline derivatives as insecticides
JP2013520456A (ja) * 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 イソオキサゾリン誘導体の製造方法
CN102822168A (zh) * 2010-02-25 2012-12-12 先正达参股股份有限公司 制备异恶唑啉衍生物的方法
WO2011104089A1 (en) * 2010-02-25 2011-09-01 Syngenta Participations Ag Process for the preparation of isoxazoline derivatives
CN102822168B (zh) * 2010-02-25 2016-10-26 先正达参股股份有限公司 制备异恶唑啉衍生物的方法
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 (zh) * 2011-03-10 2014-01-15 佐蒂斯有限责任公司 作为抗寄生物剂的螺环异噁唑啉衍生物
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 (ja) * 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 アリールチオアセトアミド誘導体をベースとする殺虫化合物
JPWO2013021949A1 (ja) * 2011-08-05 2015-03-05 日産化学工業株式会社 置換４，４−ジフルオロ−２−ブテン−１−オン化合物及び置換イソキサゾリン化合物の製造方法
WO2013021949A1 (ja) * 2011-08-05 2013-02-14 日産化学工業株式会社 置換４，４－ジフルオロ－２－ブテン－１－オン化合物及び置換イソキサゾリン化合物の製造方法
JPWO2013069731A1 (ja) * 2011-11-08 2015-04-02 日産化学工業株式会社 光学活性イソキサゾリン化合物の触媒的不斉合成方法及び光学活性イソキサゾリン化合物
WO2013069731A1 (ja) * 2011-11-08 2013-05-16 日産化学工業株式会社 光学活性イソキサゾリン化合物の触媒的不斉合成方法及び光学活性イソキサゾリン化合物
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 (ja) * 2013-05-27 2014-12-04 住友化学株式会社 光学活性なイソキサゾリン化合物の製造方法
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
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
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

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Publication number Publication date
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JP5365807B2 (ja) 2013-12-11

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