JP2014511367A5 - - Google Patents
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- Publication number
- JP2014511367A5 JP2014511367A5 JP2013551371A JP2013551371A JP2014511367A5 JP 2014511367 A5 JP2014511367 A5 JP 2014511367A5 JP 2013551371 A JP2013551371 A JP 2013551371A JP 2013551371 A JP2013551371 A JP 2013551371A JP 2014511367 A5 JP2014511367 A5 JP 2014511367A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- alkyl
- cycloalkyl
- cyano
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 6
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- -1 hydroxypropyl Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 0 *c(cc1*)cc(*)c1N Chemical compound *c(cc1*)cc(*)c1N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161437280P | 2011-01-28 | 2011-01-28 | |
| US61/437,280 | 2011-01-28 | ||
| PCT/US2012/022899 WO2012103436A1 (en) | 2011-01-28 | 2012-01-27 | Method for preparing 2-aminobenzamide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014511367A JP2014511367A (ja) | 2014-05-15 |
| JP2014511367A5 true JP2014511367A5 (show.php) | 2015-03-05 |
Family
ID=45582051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013551371A Pending JP2014511367A (ja) | 2011-01-28 | 2012-01-27 | ２−アミノベンズアミド誘導体の調製方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US8871939B2 (show.php) |
| EP (1) | EP2668153B1 (show.php) |
| JP (1) | JP2014511367A (show.php) |
| KR (1) | KR20140006007A (show.php) |
| CN (1) | CN103328434A (show.php) |
| AU (1) | AU2012211165A1 (show.php) |
| BR (1) | BR112013018228A2 (show.php) |
| HU (1) | HUE025309T2 (show.php) |
| IL (1) | IL226892A (show.php) |
| MX (1) | MX2013008560A (show.php) |
| TW (1) | TW201235338A (show.php) |
| WO (1) | WO2012103436A1 (show.php) |
| ZA (1) | ZA201304330B (show.php) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013007603A1 (de) * | 2011-07-08 | 2013-01-17 | Bayer Intellectual Property Gmbh | Verfahren zur herstellung von 2-amino-5-cyano-n,3-dimethylbenzamid |
| CN104245666B (zh) | 2012-02-07 | 2019-01-11 | 拜耳知识产权有限责任公司 | 取代的邻氨基苯甲酸衍生物的制备方法 |
| TWI678354B (zh) * | 2014-05-29 | 2019-12-01 | 新加坡商艾佛艾姆希農業新加坡有限公司 | 藉空氣氧化製備３-甲基-２-硝基苯甲酸之製程 |
| CN107522689B (zh) * | 2016-06-21 | 2021-11-23 | 华东理工大学 | 氯虫苯甲酰胺的多晶型及其制备方法 |
| WO2020117493A1 (en) * | 2018-12-03 | 2020-06-11 | Fmc Corporation | Method for preparing n-phenylpyrazole-1-carboxamides |
| ES3031276T3 (en) * | 2018-12-24 | 2025-07-07 | Upl Ltd | Process for preparation of anthranilamides |
| PT3927701T (pt) | 2019-02-18 | 2025-02-03 | Pi Industries Ltd | Um processo de preparação de diamidas antranílicas e seus intermediários |
| US11718584B2 (en) | 2019-02-22 | 2023-08-08 | Pi Industries Ltd. | Process for the synthesis anthranilic diamide compounds and intermediates thereof |
| WO2021219424A1 (en) * | 2020-04-29 | 2021-11-04 | Basf Se | Preparation of aromatic carboxyamides by a palladium-catalyzed carbonylation reaction |
| TW202219046A (zh) * | 2020-07-23 | 2022-05-16 | 美商富曼西公司 | 藉由使用一結晶中間體改善剋安勃製程 |
| IL301271A (en) | 2020-09-17 | 2023-05-01 | Pi Industries Ltd | A process for the synthesis of anthranilic acid/amide compounds and intermediates thereof |
| TW202222162A (zh) | 2020-09-26 | 2022-06-16 | 印度商皮埃企業有限公司 | 鄰胺苯甲酸／醯胺化合物及其中間體的合成方法 |
| CN115417781B (zh) * | 2022-09-30 | 2023-08-29 | 西安凯立新材料股份有限公司 | 一种制备氯虫苯甲酰胺中间体k胺的方法 |
| WO2024116197A1 (en) * | 2022-11-30 | 2024-06-06 | Natco Pharma Limited | An improved process for the preparation of intermediate of cyantraniliprole |
| CN121175296A (zh) * | 2023-06-08 | 2025-12-19 | 上海森辉医药有限公司 | 一种甲酰胺类化合物的制备方法 |
| WO2025134143A1 (en) | 2023-12-19 | 2025-06-26 | Pi Industries Ltd. | A method for the synthesis of substituted anthranilic amide compounds, intermediates and salts thereof |
| WO2025188963A1 (en) | 2024-03-06 | 2025-09-12 | Fmc Corporation | Metal catalyzed synthesis of 2-aminobenzamide derivatives |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE469892T1 (de) | 2001-08-13 | 2010-06-15 | Du Pont | Substituierte 1h-dihydropyrazole, ihre herstellung und verwendung |
| TWI371450B (en) | 2001-08-13 | 2012-09-01 | Du Pont | Novel substituted dihydro 3-halo-1h-pyrazole-5-carboxylates,their preparation and use |
| AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
| CN100453532C (zh) * | 2001-08-16 | 2009-01-21 | 纳幕尔杜邦公司 | 防治无脊椎害虫的取代的邻氨基苯甲酰胺类化合物 |
| JP2004043474A (ja) | 2002-07-05 | 2004-02-12 | Nippon Nohyaku Co Ltd | ２−アミノ安息香酸誘導体及びその製造方法 |
| TWI343376B (en) | 2002-07-31 | 2011-06-11 | Du Pont | Method for preparing 3-halo-4, 5-dihydro-1h-pyrazoles |
| SE526014C2 (sv) | 2002-09-11 | 2005-06-14 | Anmedic Ab | En apparat för att försörja en patient med en blandning av bärgas och ett gasformigt anestesimedel |
| US7211270B2 (en) * | 2002-10-04 | 2007-05-01 | E. I. Du Pont De Nemours And Company | Anthranilamide insecticides |
| TWI367882B (en) | 2003-03-26 | 2012-07-11 | Du Pont | Preparation and use of 2-substituted-5-oxo-3-pyrazolidinecarboxylates |
| EP1736465A4 (en) * | 2004-03-31 | 2009-06-17 | Ajinomoto Kk | ANILINE DERIVATIVES |
| TWI363756B (en) | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| GB0426894D0 (en) | 2004-12-08 | 2005-01-12 | Stylacats Ltd | Process |
| EP2088861A4 (en) | 2006-10-25 | 2010-07-07 | Takeda Pharmaceutical | Benzimidazole compounds |
| TWI431000B (zh) * | 2008-03-05 | 2014-03-21 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
| CN102046577B (zh) * | 2008-05-27 | 2014-09-24 | 巴斯夫欧洲公司 | 生产芳族和杂芳族羧酸、羧酸酯和羧酰胺的方法 |
| KR20100092909A (ko) | 2009-02-13 | 2010-08-23 | 주식회사 엘지생명과학 | 잔틴 옥시다제 저해제로서 효과적인 신규 화합물, 그 제조방법 및 그를 함유하는 약제학적 조성물 |
| CN101717395A (zh) * | 2009-12-04 | 2010-06-02 | 南开大学 | 一种氯虫苯甲酰胺农药的合成方法 |
-
2012
- 2012-01-27 HU HUE12703656A patent/HUE025309T2/en unknown
- 2012-01-27 EP EP12703656.4A patent/EP2668153B1/en not_active Not-in-force
- 2012-01-27 JP JP2013551371A patent/JP2014511367A/ja active Pending
- 2012-01-27 US US13/981,919 patent/US8871939B2/en active Active - Reinstated
- 2012-01-27 CN CN2012800057831A patent/CN103328434A/zh active Pending
- 2012-01-27 BR BR112013018228A patent/BR112013018228A2/pt not_active IP Right Cessation
- 2012-01-27 KR KR1020137022651A patent/KR20140006007A/ko not_active Withdrawn
- 2012-01-27 MX MX2013008560A patent/MX2013008560A/es not_active Application Discontinuation
- 2012-01-27 AU AU2012211165A patent/AU2012211165A1/en not_active Abandoned
- 2012-01-27 WO PCT/US2012/022899 patent/WO2012103436A1/en not_active Ceased
- 2012-01-30 TW TW101102830A patent/TW201235338A/zh unknown
-
2013
- 2013-06-12 ZA ZA2013/04330A patent/ZA201304330B/en unknown
- 2013-06-12 IL IL226892A patent/IL226892A/en not_active IP Right Cessation
-
2014
- 2014-09-16 US US14/487,600 patent/US9162973B2/en active Active
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