DK2454242T3 - Fremgangsmåde til fremstilling af chirale 3-triazolyl-sulfoxid-derivater - Google Patents
Fremgangsmåde til fremstilling af chirale 3-triazolyl-sulfoxid-derivater Download PDFInfo
- Publication number
- DK2454242T3 DK2454242T3 DK10732316.4T DK10732316T DK2454242T3 DK 2454242 T3 DK2454242 T3 DK 2454242T3 DK 10732316 T DK10732316 T DK 10732316T DK 2454242 T3 DK2454242 T3 DK 2454242T3
- Authority
- DK
- Denmark
- Prior art keywords
- alkyl
- hydrogen
- chiral
- enantiomer
- cyano
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (8)
1. Fremgangsmåde til fremstilling af 3-triazolyl-sulfoxidderivater med formel (I) i enantiomerren eller enantiomerberiget form,
(i) Hvor X1 og X2 uafhængigt af hinanden står for fluor, chlor, brom, hydrogen, (C1-C12) alkyl, (C1-C12) halogenalkyl, Y1 og Y2 uafhængigt af hinanden står for fluor, chlor, brom, hydrogen, (C1-C12) alkyl, (C1-C12) halogenalkyl, R1 og R2 uafhængigt af hinanden står for hydrogen, (Ci— C12) alkyl, (C1-C12) halogenalkyl, cyano, halogen, nitro, R3 står for hydrogen, (C1-C12) alkyl, amino, nitro, NH(CO) (Ci-C12) alkyl, N=CR'R, idet R, R' uafhængigt af hinanden står for hydrogen, (Ci- C12) alkyl, aryl, kendetegnet ved, at man (A) omsætter et sulfid med formel (II)
(») hvor X1, X2, Y1, Y2, R1, R2 og R3 har de ovenfor nævnte betegnelser, i nærvær af en chiral katalysator og et oxidationsmiddel, idet oxidationsmidlet er udvalgt af hydrogenperoxid, alkylhydroperoxid og arylalkylhydroperoxid, og idet den chirale katalysator er et chiralt metal-ligand-kompleks, og metallet er et overgangsmetal.
2. Fremgangsmåde ifølge krav 1, kendetegnet ved, at enantiomerforholdet er 50,5:49,5 til 99,5:0,5 (+):(-) eller (-):(+)-enantiomer.
3. Fremgangsmåde ifølge et af kravene 1 til 2, kendetegnet ved, at enantiomerforholdet er 50,5:49,5 til 99,5:0,5 (+):(-) enantiomer.
4. Fremgangsmåde ifølge et af kravene 1 til 3, kendetegnet ved, at X1 og X2, Y1 og Y2 uafhængigt af hinanden står for fluor, chlor, hydrogen, (C1-C12) halogenalkyl, R1 og R2 uafhængigt af hinanden står for fluor, hydrogen, (Ci-C6) alkyl, R3 står for hydrogen, amino.
5. Fremgangsmåde ifølge et af kravene 1 til 4, kendetegnet ved, at X1 og X2, Y1 og Y2 uafhængigt af hinanden står for fluor, hydrogen, (Ci-C6) halogenalkyl, R1 og R2 uafhængigt af hinanden står for fluor, methyl, R3 står for hydrogen.
6. Fremgangsmåde ifølge et af kravene 1 til 5, kendetegnet ved, at der som chiral katalysator anvendes et chiralt metal-ligand-kompleks, idet metallet er et overgangsmetal, og liganden er en forbindelse med formel (III) eller (IV), idet
R4 og R5 i formel (III) uafhængigt af hinanden står for hydrogen, (C1-C6) alkyl, (C1-C6) alkylphenyl, phenyl, halogen, cyano, nitro, cyano (Ci-Ce) alkyl, hydroxy (C1-C6) alkyl, (Ci-Οε) alkoxycarbonyl (C1-C6) alkyl, (C1-C6) alkoxy (C1-C6) alkyl, R6 står for (Ci-Ce) alkyl, for (Ci-C6) alkyl, carboxyl, carbonyl (Ci-C6) alkyl, (Ci-Οε) alkoxycarbonyl (Ci-Οε) alkyl, (Ci — Οε) alkoxy (Ci-C6) alkyl, (Ci-Οε) alkoxy, di (Ci-C6) alkoxy (Ci — Ce)alkyl, som er substitueret med halogen, cyano, nitro, amino, hydroxy eller phenyl, R7 står for hydrogen, (Ci-Ce) alkyl, (Οι-Οε) alkylphenyl, aryl, aryl(Ci-Ce)alkyl, fortrinsvis for tert-butyl, benzyl, phenyl, og chirale carbonatomer er mærket med *, idet R8 i formel (IV) står for hydrogen, (Ci-Ce) alkyl, (Οι-Οε) alkylphenyl, phenyl, halogen, cyano, nitro, cyano(Ci-Ce)alkyl, hydroxy(Ci-Ce) alkyl, (Οχ-Οε) alkoxycarbonyl (Οι~Οε) alkyl, (Οι~Οε) alkoxy (Ci-C6) alkyl, R9 og R10 står for hydrogen, (Ci-Οε) alkyl, phenyl, idet R9 og R10 kan danne en bro, og chirale carbonatomer er mærket med *.
7. Fremgangsmåde ifølge et af kravene 1 til 6, kendetegnet ved, at der i tilslutning til trin (A) gennemføres en krystallisation af organisk opløsningsmiddel eller en blanding af organisk opløsningsmiddel med vand.
8. Enantiomerrene eller enantiomerberigede 3-triazolyl- sulfoxid-derivater med formel (I) , som kan fremstilles ifølge fremgangsmåden ifølge et af kravene 1 til 7, idet enantiomerforholdet er 50,5:49,5 til 99,5:0,5 (+):(- ) enantiomer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009027771 | 2009-07-16 | ||
| PCT/EP2010/004288 WO2011006646A1 (de) | 2009-07-16 | 2010-07-14 | Verfahren zur herstellung von chiralen 3-triazolyl-sulfoxid-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2454242T3 true DK2454242T3 (da) | 2015-02-02 |
Family
ID=42710633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10732316.4T DK2454242T3 (da) | 2009-07-16 | 2010-07-14 | Fremgangsmåde til fremstilling af chirale 3-triazolyl-sulfoxid-derivater |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US8314133B2 (da) |
| EP (1) | EP2454242B1 (da) |
| JP (1) | JP5676602B2 (da) |
| KR (1) | KR20120037993A (da) |
| CN (1) | CN102471290B (da) |
| BR (1) | BR112012001078A8 (da) |
| DK (1) | DK2454242T3 (da) |
| ES (1) | ES2525535T3 (da) |
| IL (1) | IL217136A0 (da) |
| IN (1) | IN2012DN00422A (da) |
| MX (1) | MX2012000583A (da) |
| RU (1) | RU2012105122A (da) |
| TW (1) | TWI471314B (da) |
| WO (1) | WO2011006646A1 (da) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2454242B1 (de) | 2009-07-16 | 2014-10-15 | Bayer CropScience AG | Verfahren zur herstellung von chiralen 3-triazolyl-sulfoxid-derivaten |
| EP2274982A1 (de) * | 2009-07-16 | 2011-01-19 | Bayer CropScience AG | Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut |
| US8242313B2 (en) | 2009-07-23 | 2012-08-14 | Bayer Cropscience Ag | Alkoxy enones and enamino ketones and a process for preparation thereof |
| IN2012DN00638A (da) * | 2009-07-23 | 2015-08-21 | Bayer Cropscience Ag | |
| JP6140446B2 (ja) * | 2009-08-20 | 2017-05-31 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 殺ダニ剤および殺虫剤としての３−トリアゾリルフェニル置換スルフィド誘導体 |
| KR20120089458A (ko) * | 2009-08-20 | 2012-08-10 | 바이엘 크롭사이언스 아게 | 살비제 및 살충제로 사용하기 위한 3-〔1-(3-할로알킬)트리아졸릴〕페닐 설파이드 유도체 |
| EP2578575B1 (en) * | 2010-06-01 | 2016-05-04 | Kumiai Chemical Industry CO., LTD. | Triazole compound having pest-controlling activity |
| EP2606726A1 (de) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | N-Arylamidine-substituierte trifluoroethylsulfid-Derivate als Akarizide und Insektizide |
| EP2900634B1 (en) | 2012-09-27 | 2017-02-22 | Bayer CropScience AG | Process for the preparation of optionally substituted phenyl and pyridyl pyrrolidines |
| AR093909A1 (es) | 2012-12-12 | 2015-06-24 | Bayer Cropscience Ag | Uso de ingredientes activos para controlar nematodos en cultivos resistentes a nematodos |
| WO2015036380A1 (de) | 2013-09-13 | 2015-03-19 | Bayer Cropscience Ag | Verfahren zur reduktion von arylsulfoxiden zu arylthioethern |
| WO2015135984A1 (de) | 2014-03-13 | 2015-09-17 | Bayer Cropscience Ag | Verfahren zur herstellung von chiralen 3-(5-aminotriazolyl)-sulfoxid-derivaten |
| AR113445A1 (es) * | 2017-10-18 | 2020-05-06 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas / acaricidas |
| WO2021084074A1 (en) | 2019-10-30 | 2021-05-06 | Solvay Sa | Compositions and films comprising a polymer and tis2 particles, and their preparation and uses |
| EP4144723A1 (en) | 2020-04-30 | 2023-03-08 | Kumiai Chemical Industry Co., Ltd. | Method for producing monosulfoxide derivative |
| JP2024512032A (ja) | 2021-03-26 | 2024-03-18 | バイエル・アクチエンゲゼルシヤフト | エナンチオマー富化形態での（２ｚ）－２－（フェニルイミノ）－１，３－チアゾリジンｅ－４－オン－スルホキシド誘導体の製造方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1076053B1 (en) * | 1998-04-27 | 2006-11-29 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenyl sulfide derivatives and insecticides and miticides |
| JP2006523201A (ja) * | 2003-03-28 | 2006-10-12 | シデム ファーマ | スルホキシド誘導体をエナンチオ選択的に調製する方法 |
| FR2863611B1 (fr) * | 2003-12-15 | 2006-03-24 | Sidem Pharma Sa | Procede de preparation enantioselective de derives de sulfoxydes |
| FR2852956B1 (fr) * | 2003-03-28 | 2006-08-04 | Negma Gild | Procede de preparation enantioselective de derives de sulfoxydes |
| EP1516869A1 (en) * | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| FR2876101B1 (fr) * | 2004-10-05 | 2007-03-02 | Sidem Pharma Sa Sa | Procede de preparation enantioselective de derives de sulfoxydes |
| EP1802584B1 (en) * | 2004-10-11 | 2009-09-16 | Ranbaxy Laboratories Limited | Processes for the preparation of substituted sulfoxides |
| KR101310073B1 (ko) * | 2004-10-20 | 2013-09-24 | 이하라케미칼 고교가부시키가이샤 | 3-트리아졸릴페닐설파이드 유도체 및 그것을유효성분으로서 함유하는 살충·살진드기·살선충제 |
| CN101012141B (zh) * | 2007-02-02 | 2012-05-23 | 沈阳药科大学 | 手性亚砜类化合物的制备方法 |
| JP5507257B2 (ja) * | 2007-11-30 | 2014-05-28 | イハラケミカル工業株式会社 | （１ｈ−１，２，４−トリアゾール−１−イル）アリール化合物及びその製造方法 |
| CN101323582A (zh) * | 2008-07-30 | 2008-12-17 | 大连理工大学 | 一类手性西佛碱配体及其在硫醚不对称氧化反应中的应用 |
| CN101429192A (zh) * | 2008-08-22 | 2009-05-13 | 扬子江药业集团有限公司 | 生产手性亚砜衍生物的新方法 |
| EP2274982A1 (de) | 2009-07-16 | 2011-01-19 | Bayer CropScience AG | Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut |
| EP2454242B1 (de) | 2009-07-16 | 2014-10-15 | Bayer CropScience AG | Verfahren zur herstellung von chiralen 3-triazolyl-sulfoxid-derivaten |
| KR20120089458A (ko) * | 2009-08-20 | 2012-08-10 | 바이엘 크롭사이언스 아게 | 살비제 및 살충제로 사용하기 위한 3-〔1-(3-할로알킬)트리아졸릴〕페닐 설파이드 유도체 |
| JP6140446B2 (ja) * | 2009-08-20 | 2017-05-31 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 殺ダニ剤および殺虫剤としての３−トリアゾリルフェニル置換スルフィド誘導体 |
-
2010
- 2010-07-14 EP EP10732316.4A patent/EP2454242B1/de not_active Not-in-force
- 2010-07-14 BR BR112012001078A patent/BR112012001078A8/pt active Search and Examination
- 2010-07-14 WO PCT/EP2010/004288 patent/WO2011006646A1/de active Application Filing
- 2010-07-14 JP JP2012519925A patent/JP5676602B2/ja not_active Expired - Fee Related
- 2010-07-14 IN IN422DEN2012 patent/IN2012DN00422A/en unknown
- 2010-07-14 ES ES10732316.4T patent/ES2525535T3/es active Active
- 2010-07-14 CN CN201080031476.1A patent/CN102471290B/zh not_active Expired - Fee Related
- 2010-07-14 KR KR1020127003961A patent/KR20120037993A/ko not_active Application Discontinuation
- 2010-07-14 DK DK10732316.4T patent/DK2454242T3/da active
- 2010-07-14 RU RU2012105122/04A patent/RU2012105122A/ru not_active Application Discontinuation
- 2010-07-14 MX MX2012000583A patent/MX2012000583A/es active IP Right Grant
- 2010-07-15 TW TW99123228A patent/TWI471314B/zh not_active IP Right Cessation
- 2010-07-16 US US12/837,646 patent/US8314133B2/en not_active Expired - Fee Related
-
2011
- 2011-12-22 IL IL217136A patent/IL217136A0/en unknown
-
2012
- 2012-10-15 US US13/652,039 patent/US8765970B2/en not_active Expired - Fee Related
-
2014
- 2014-05-15 US US14/278,132 patent/US20140256953A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IN2012DN00422A (da) | 2015-05-15 |
| ES2525535T3 (es) | 2014-12-26 |
| US20140256953A1 (en) | 2014-09-11 |
| IL217136A0 (en) | 2012-02-29 |
| US8314133B2 (en) | 2012-11-20 |
| CN102471290A (zh) | 2012-05-23 |
| EP2454242A1 (de) | 2012-05-23 |
| EP2454242B1 (de) | 2014-10-15 |
| BR112012001078A8 (pt) | 2016-05-03 |
| TW201116517A (en) | 2011-05-16 |
| JP5676602B2 (ja) | 2015-02-25 |
| MX2012000583A (es) | 2012-02-13 |
| BR112012001078A2 (pt) | 2015-09-01 |
| US20130172573A1 (en) | 2013-07-04 |
| RU2012105122A (ru) | 2013-08-27 |
| CN102471290B (zh) | 2016-02-03 |
| US8765970B2 (en) | 2014-07-01 |
| KR20120037993A (ko) | 2012-04-20 |
| WO2011006646A1 (de) | 2011-01-20 |
| TWI471314B (zh) | 2015-02-01 |
| US20110015405A1 (en) | 2011-01-20 |
| JP2012532906A (ja) | 2012-12-20 |
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