JP2018515468A5 - - Google Patents
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- Publication number
- JP2018515468A5 JP2018515468A5 JP2017556540A JP2017556540A JP2018515468A5 JP 2018515468 A5 JP2018515468 A5 JP 2018515468A5 JP 2017556540 A JP2017556540 A JP 2017556540A JP 2017556540 A JP2017556540 A JP 2017556540A JP 2018515468 A5 JP2018515468 A5 JP 2018515468A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- halogen
- iii
- derivative
- integer equal
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- -1 cyanopyridyl Chemical class 0.000 claims 9
- 239000003054 catalyst Substances 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 239000003607 modifier Substances 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical class CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 230000003197 catalytic effect Effects 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 229940054066 benzamide antipsychotics Drugs 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 239000012074 organic phase Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 241001385733 Aesculus indica Species 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- JVQYWHGODHSTAM-UHFFFAOYSA-N [3-chloro-5-(trifluoromethyl)pyridin-2-yl]methanamine Chemical compound NCC1=NC=C(C(F)(F)F)C=C1Cl JVQYWHGODHSTAM-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Substances [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15165831.7 | 2015-04-30 | ||
| EP15165831.7A EP3088390A1 (en) | 2015-04-30 | 2015-04-30 | Catalytic hydrogenation of substituted cyanopyridines |
| PCT/EP2016/059215 WO2016173998A1 (en) | 2015-04-30 | 2016-04-26 | Catalytic hydrogenation of substituted cyanopyridines and process for preparing substituted pyridylmethylbenzamides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018515468A JP2018515468A (ja) | 2018-06-14 |
| JP2018515468A5 true JP2018515468A5 (enExample) | 2019-05-30 |
| JP6910957B2 JP6910957B2 (ja) | 2021-07-28 |
Family
ID=53040390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017556540A Expired - Fee Related JP6910957B2 (ja) | 2015-04-30 | 2016-04-26 | 置換シアノピリジン類の接触水素化および置換ピリジルメチルベンズアミド類の製造方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10781176B2 (enExample) |
| EP (2) | EP3088390A1 (enExample) |
| JP (1) | JP6910957B2 (enExample) |
| KR (1) | KR102526835B1 (enExample) |
| CN (1) | CN107835806A (enExample) |
| BR (1) | BR112017023411B1 (enExample) |
| DK (1) | DK3288922T3 (enExample) |
| ES (1) | ES2906727T3 (enExample) |
| IL (1) | IL255059B (enExample) |
| MX (1) | MX388855B (enExample) |
| TW (1) | TWI709555B (enExample) |
| WO (1) | WO2016173998A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3489221A1 (en) * | 2017-11-22 | 2019-05-29 | Bayer AG | Process for the preparation of fluopicolide |
| CN107814759A (zh) * | 2017-11-24 | 2018-03-20 | 常州沃腾化工科技有限公司 | 氟吡菌胺的制备方法 |
| CN110606827B (zh) * | 2019-09-26 | 2023-03-14 | 西安凯立新材料股份有限公司 | 一步法合成甲氨基吡啶类化合物的方法 |
| CN111138351A (zh) * | 2020-01-13 | 2020-05-12 | 大连九信精细化工有限公司 | 一种2-氨甲基-3-氯-5-三氟甲基吡啶醋酸盐的合成方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2649978B1 (fr) | 1989-07-20 | 1991-10-25 | Rhone Poulenc Chimie | Procede d'hydrogenation de derives halogeno nitroaromatiques en presence d'iodures |
| MX9300433A (es) | 1992-01-28 | 1994-07-29 | Kirin Brewery | Compuestos de piridincarboximidamina y composiciones farmaceuticas que los contienen. |
| JPH07138209A (ja) * | 1993-11-12 | 1995-05-30 | Sumitomo Seika Chem Co Ltd | 含ハロゲンアミノメチル化合物の製造法 |
| TW575562B (en) | 1998-02-19 | 2004-02-11 | Agrevo Uk Ltd | Fungicides |
| BR0113259B1 (pt) | 2000-08-25 | 2014-09-02 | Bayer Cropscience Sa | Processo para a preparação de um composto 2-aminometilpiridina de fórmula (I) |
| GB0021066D0 (en) * | 2000-08-25 | 2000-10-11 | Aventis Cropscience Sa | Novel process |
| GB0025616D0 (en) * | 2000-10-19 | 2000-12-06 | Aventis Cropscience Sa | Novel process |
| KR100818566B1 (ko) * | 2000-08-25 | 2008-04-01 | 바이엘 크롭사이언스 소시에떼아노님 | 2-아미노에틸피리딘의 제조 방법 |
| EP1422221A1 (en) * | 2002-11-20 | 2004-05-26 | Bayer CropScience SA | Novel process for the preparation of 2-aminomethylpyridine derivative |
| ES2377821T3 (es) * | 2006-10-11 | 2012-04-02 | Amgen Inc. | Compuestos de imidazo- y triazolo-piridina y métodos de uso de los mismos. |
| JP5659860B2 (ja) * | 2011-02-28 | 2015-01-28 | エヌ・イーケムキャット株式会社 | ニトリル化合物水素化用パラジウム含有触媒および該触媒を用いたニトリル化合物の水素化方法 |
| US9493412B2 (en) * | 2011-09-27 | 2016-11-15 | Bristol-Myers Squibb Company | Pyrrolinone carboxamide compounds useful as endothelial lipase inhibitors |
-
2015
- 2015-04-30 EP EP15165831.7A patent/EP3088390A1/en not_active Ceased
-
2016
- 2016-04-26 EP EP16718367.2A patent/EP3288922B1/en active Active
- 2016-04-26 DK DK16718367.2T patent/DK3288922T3/da active
- 2016-04-26 MX MX2017013919A patent/MX388855B/es unknown
- 2016-04-26 WO PCT/EP2016/059215 patent/WO2016173998A1/en not_active Ceased
- 2016-04-26 BR BR112017023411-4A patent/BR112017023411B1/pt not_active IP Right Cessation
- 2016-04-26 CN CN201680037551.2A patent/CN107835806A/zh active Pending
- 2016-04-26 US US15/569,528 patent/US10781176B2/en not_active Expired - Fee Related
- 2016-04-26 JP JP2017556540A patent/JP6910957B2/ja not_active Expired - Fee Related
- 2016-04-26 KR KR1020177034393A patent/KR102526835B1/ko active Active
- 2016-04-26 ES ES16718367T patent/ES2906727T3/es active Active
- 2016-04-28 TW TW105113216A patent/TWI709555B/zh not_active IP Right Cessation
-
2017
- 2017-10-16 IL IL255059A patent/IL255059B/en active IP Right Grant
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