DK2414345T3 - Fremgangsmåde til fremstilling af pyridyl-substituerede pyrazoler - Google Patents
Fremgangsmåde til fremstilling af pyridyl-substituerede pyrazoler Download PDFInfo
- Publication number
- DK2414345T3 DK2414345T3 DK10712340.8T DK10712340T DK2414345T3 DK 2414345 T3 DK2414345 T3 DK 2414345T3 DK 10712340 T DK10712340 T DK 10712340T DK 2414345 T3 DK2414345 T3 DK 2414345T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- alkyl
- compounds
- stands
- halogen
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Claims (9)
1. Fremgangsmåde til fremstilling af pyridyl-substituerede pyrazolderivater med den almene formel (1)
hvor R1 står for alkoxy, hydroxy, aryloxy, alkylaryloxy, alkyl, cycloalkyl, halogen, R2 står for hydroxy, alkoxy, arylalkoxy, alkylthio, for chlor, brom, fluor, rod, 0-(C=0)alkyl, 0-(C=0)0-alkyl, OSCgalkyl, OSCgPh, OSCg-halogenalkyl, OSCg-aryl, kendetegnet ved, at man omsætter (A) acetylenketoner med formel (II)
hvor R4 står for en beskyttelsesgruppe udvalgt af (CR-Ce)-alkyl, aryl, benzyl, tetrahydropyran, (C=0)-alkyl, (C=0)-Oalkyl, Si(alkyl)3 og X står for halogen, med hydrazinopyridiner med formel (III)
hvor R3 står for halogen, CN, NCR, alkyl, cycloalkyl, halogenalkyl, halogencycloalkyl, alkoxy, halogenalkoxy, alkylamino, dialkylamino, cycloalkylamino, til 1-pyridyl-substituerede dihydro-lH pyrazoler med formel (IV) ,
hvor X, R3, R4 har de ovenfor anførte betegnelser, (B) i givet fald omsætter disse videre uden forudgående isolering under fraspaltning af vand til 1-pyridyl-substituerede trihalogenmethylpyrazoler med formel (V)
hvor X, R3, R4 har de ovenfor anførte betegnelser, (C) omsætter disse forbindelser med den almene formel (V) under tilsætning af eksempelvis H2SO4 til pyrazolcarboxylsyrer med formel (VI),
hvor R3, R4 har de ovenfor anførte betegnelser, (D) omsætter disse efter fraspaltning af beskyttelsesgruppen R4 til hydroxymethylpyrazolsyrer med formel (VII),
hvor R3 de ovenfor anførte betegnelser, og (E) omsætter disse til forbindelser med formel (I).
2. Fremgangsmåde til fremstilling af forbindelser med formel (I) ifølge krav 1, kendetegnet ved, at R1 står for (CR-Ce) -alkoxy, halogen, R2 står for (Οι-Οε) -alkoxy, aryl (Ci-Ce) -alkoxy, fluor, chlor, brom, rod, R3 står for halogen, CN, NO2, (C1-C6) -alkyl, halogen (CR-Ce) -alkyl, (C1-C6) alkoxy, halogen (C1-C6) alkoxy.
3. Fremgangsmåde til fremstilling af forbindelser med formel (I), kendetegnet ved, at fremstillingen af forbindelsen med formel (V) omfatter trinnene (A) og (B) ifølge krav 1.
4. Fremgangsmåde til fremstilling af forbindelser med formel (I) ifølge krav 3, kendetegnet ved, at forbindelserne med formel (V) ,
hvor X står for halogen, R4 står for en beskyttelsesgruppe udvalgt af (Ci-C6)-alkyl, aryl, benzyl, tetrahydropyran, (C=0)-alkyl, (C=0)-Oalkyl, Si(alkyl)3 R3 står for halogen, CN, NO2, alkyl, cycloalkyl, halogenalkyl, halogencycloalkyl, alkoxy, halogenalkoxy, alkylamino, dialkylamino, cycloalkylamino, ved hjælp af fraspaltning af beskyttelsesgruppen omsættes til forbindelser med formel (VIII),
hvor X, R3 har de ovenfor anførte betegnelser, omsætter disse under hydrolyse til forbindelser med den almene formel (VII),
hvor R3 har de ovenfor anførte betegnelser, og omsætter disse under tilsætning af et halogeneringsmiddel og efterfølgende tilsætning af alkohol til forbindelser med formel (I).
5. Fremgangsmåde til fremstilling af forbindelser med formel (I) ifølge krav 3, kendetegnet ved, at forbindelserne med formel (V), hvor X står for halogen, R4 står for en beskyttelsesgruppe udvalgt af (Ci-C6)-alkyl, aryl, benzyl, tetrahydropyran, (C=0) alkyl, (C=0)-Oalkyl, Si (alkyl)3 R3 står for halogen, CN, NO2, alkyl, cycloalkyl, halogenalkyl, halogencycloalkyl, alkoxy, halogenalkoxy, alkylamino, dialkylamino, cycloalkylamino, omsættes under tilsætning af alkohol direkte til forbindelserne med formel (I) ifølge opfindelsen.
6. Forbindelser med formel (IV)
kendetegnet ved, at X står for halogen, R3 står for chlor, R4 står for benzyl.
7. Forbindelser med formel (V)
kendetegnet ved, at X står for halogen, R3 står for chlor, R4 står for benzyl.
8. Forbindelser med formel (V) ifølge krav 7, kendetegnet ved, at X står for chlor.
9. Forbindelser med formel (VII),
kendetegnet ved, at R3 står for halogen, CN, NO2, alkyl, cycloalkyl, halogenalkyl, halogencycloalkyl, alkoxy, halogenalkoxy, alkylamino, dialkylamino, cycloalkylamino.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09157317A EP2243777A1 (de) | 2009-04-03 | 2009-04-03 | Verfahren zum Herstellen von Pyridyl-substituierten Pyrazolen |
| PCT/EP2010/001926 WO2010112178A1 (de) | 2009-04-03 | 2010-03-26 | Verfahren zum herstellen von pyridyl-substituierten pyrazolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2414345T3 true DK2414345T3 (da) | 2014-12-15 |
Family
ID=40810800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10712340.8T DK2414345T3 (da) | 2009-04-03 | 2010-03-26 | Fremgangsmåde til fremstilling af pyridyl-substituerede pyrazoler |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US8362261B2 (da) |
| EP (2) | EP2243777A1 (da) |
| JP (1) | JP5752676B2 (da) |
| KR (1) | KR101705285B1 (da) |
| CN (1) | CN102388033B (da) |
| BR (1) | BRPI1014066A8 (da) |
| DK (1) | DK2414345T3 (da) |
| ES (1) | ES2523991T3 (da) |
| IL (1) | IL215024A (da) |
| MX (1) | MX2011010242A (da) |
| TW (1) | TWI477496B (da) |
| WO (1) | WO2010112178A1 (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2243777A1 (de) | 2009-04-03 | 2010-10-27 | Bayer CropScience AG | Verfahren zum Herstellen von Pyridyl-substituierten Pyrazolen |
| MX2012006723A (es) | 2009-12-15 | 2012-06-28 | Bayer Cropscience Ag | Procedimiento para la preparacion de derivados de acido 1-alquil-/1-aril-5-pirazolcarboxilico. |
| KR101331716B1 (ko) | 2013-02-04 | 2013-11-20 | 안영미 | 무단변속장치 |
| MX2015017640A (es) * | 2013-06-20 | 2016-09-07 | Basf Se | Proceso para preparar compuestos de piridilpirazol y sus derivados de piridilhidrazina. |
| CN105732502B (zh) * | 2014-12-09 | 2018-03-16 | 中国科学院大连化学物理研究所 | 一种制备手性4,5‑二氢吡唑类化合物的方法 |
| KR20210011918A (ko) | 2018-05-21 | 2021-02-02 | 피아이 인더스트리스 엘티디. | 안트라닐산 디아미드의 새로운 제조 방법 |
| WO2020016841A1 (en) | 2018-07-20 | 2020-01-23 | Pi Industries Ltd. | A novel process for the preparation of anthranilic diamides |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO179282C (no) * | 1991-01-18 | 1996-09-11 | Rhone Poulenc Agrochimie | Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter |
| DE19904406A1 (de) * | 1999-02-04 | 2000-08-10 | Bayer Ag | Substituierte Pyrazolcarbonsäuren |
| AU2002319814A1 (en) | 2001-08-13 | 2003-03-03 | E.I. Du Pont De Nemours And Company | Substituted 1h-dihydropyrazoles, their preparation and use |
| JP2006522130A (ja) * | 2003-04-03 | 2006-09-28 | メルク エンド カムパニー インコーポレーテッド | ナトリウムチャンネル遮断薬としてのビアリール置換ピラゾール |
| JP2005008628A (ja) | 2003-05-27 | 2005-01-13 | Nissan Chem Ind Ltd | アクリロニトリル化合物 |
| ES2534605T3 (es) | 2004-08-23 | 2015-04-24 | Eli Lilly And Company | Agentes receptores de la histamina H3, preparación y usos terapéuticos |
| DE102006042437A1 (de) * | 2006-03-30 | 2007-10-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| DE102006032168A1 (de) | 2006-06-13 | 2007-12-20 | Bayer Cropscience Ag | Anthranilsäurediamid-Derivate mit heteroaromatischen Substituenten |
| EP2243777A1 (de) | 2009-04-03 | 2010-10-27 | Bayer CropScience AG | Verfahren zum Herstellen von Pyridyl-substituierten Pyrazolen |
| EP2456747B1 (de) | 2009-07-23 | 2014-06-25 | Bayer CropScience AG | Verfahren zur Herstellung von Alkoxyenonen und Enaminoketonen |
| JP5872467B2 (ja) | 2009-07-23 | 2016-03-01 | 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 | アリール置換ピラゾールの調製方法 |
| US8242313B2 (en) | 2009-07-23 | 2012-08-14 | Bayer Cropscience Ag | Alkoxy enones and enamino ketones and a process for preparation thereof |
-
2009
- 2009-04-03 EP EP09157317A patent/EP2243777A1/de not_active Ceased
-
2010
- 2010-03-26 DK DK10712340.8T patent/DK2414345T3/da active
- 2010-03-26 CN CN201080015390.XA patent/CN102388033B/zh not_active Expired - Fee Related
- 2010-03-26 MX MX2011010242A patent/MX2011010242A/es active IP Right Grant
- 2010-03-26 EP EP10712340.8A patent/EP2414345B1/de not_active Not-in-force
- 2010-03-26 ES ES10712340.8T patent/ES2523991T3/es active Active
- 2010-03-26 JP JP2012502500A patent/JP5752676B2/ja not_active Expired - Fee Related
- 2010-03-26 BR BRPI1014066A patent/BRPI1014066A8/pt not_active Application Discontinuation
- 2010-03-26 WO PCT/EP2010/001926 patent/WO2010112178A1/de active Application Filing
- 2010-03-26 KR KR1020117025721A patent/KR101705285B1/ko active IP Right Grant
- 2010-04-02 US US12/753,447 patent/US8362261B2/en active Active
- 2010-04-02 TW TW099110267A patent/TWI477496B/zh not_active IP Right Cessation
-
2011
- 2011-09-07 IL IL215024A patent/IL215024A/en not_active IP Right Cessation
-
2013
- 2013-01-11 US US13/739,446 patent/US8987460B2/en not_active Expired - Fee Related
-
2015
- 2015-03-23 US US14/665,583 patent/US9340526B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20110087029A1 (en) | 2011-04-14 |
| EP2414345A1 (de) | 2012-02-08 |
| TW201105648A (en) | 2011-02-16 |
| KR101705285B1 (ko) | 2017-02-09 |
| US20120136156A2 (en) | 2012-05-31 |
| IL215024A0 (en) | 2011-11-30 |
| US20150191447A1 (en) | 2015-07-09 |
| WO2010112178A1 (de) | 2010-10-07 |
| EP2243777A1 (de) | 2010-10-27 |
| IL215024A (en) | 2015-07-30 |
| US20130131347A1 (en) | 2013-05-23 |
| EP2414345B1 (de) | 2014-09-17 |
| JP5752676B2 (ja) | 2015-07-22 |
| US8362261B2 (en) | 2013-01-29 |
| BRPI1014066A8 (pt) | 2016-05-24 |
| US9340526B2 (en) | 2016-05-17 |
| KR20120006030A (ko) | 2012-01-17 |
| CN102388033A (zh) | 2012-03-21 |
| ES2523991T3 (es) | 2014-12-03 |
| US8987460B2 (en) | 2015-03-24 |
| MX2011010242A (es) | 2011-10-28 |
| BRPI1014066A2 (pt) | 2015-08-25 |
| CN102388033B (zh) | 2015-10-14 |
| JP2012522735A (ja) | 2012-09-27 |
| TWI477496B (zh) | 2015-03-21 |
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