JP2016540820A5 - - Google Patents
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- Publication number
- JP2016540820A5 JP2016540820A5 JP2016541134A JP2016541134A JP2016540820A5 JP 2016540820 A5 JP2016540820 A5 JP 2016540820A5 JP 2016541134 A JP2016541134 A JP 2016541134A JP 2016541134 A JP2016541134 A JP 2016541134A JP 2016540820 A5 JP2016540820 A5 JP 2016540820A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- mmol
- benzyl
- butyl
- methyl
- 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
Links
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- -1 n-octyl Chemical group 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- BRSVPNMUMXRLAF-UHFFFAOYSA-N 1-benzyl-N-(2,2-dimethylpropyl)-N,4-dimethyl-3-(6-oxo-1H-pyridin-3-yl)-5-(trifluoromethyl)pyrrole-2-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C=1C=NC(=CC1)O)C(=O)N(C)CC(C)(C)C BRSVPNMUMXRLAF-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- DVDBKJGWXQEJFJ-UHFFFAOYSA-N [1-benzyl-3-bromo-4-methyl-5-(trifluoromethyl)pyrrol-2-yl]-morpholin-4-ylmethanone Chemical compound C=1C=CC=CC=1CN1C(C(F)(F)F)=C(C)C(Br)=C1C(=O)N1CCOCC1 DVDBKJGWXQEJFJ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- TXEKKOJINFMJNT-UHFFFAOYSA-N 1-benzyl-3-bromo-4-methyl-5-(trifluoromethyl)pyrrole-2-carboxylic acid Chemical compound FC(F)(F)C1=C(C)C(Br)=C(C(O)=O)N1CC1=CC=CC=C1 TXEKKOJINFMJNT-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- RHJAQQOPSKUIRQ-UHFFFAOYSA-N [1-benzyl-3-(5-methoxypyrazin-2-yl)-4-methyl-5-(trifluoromethyl)pyrrol-2-yl]-morpholin-4-ylmethanone Chemical compound C(C1=CC=CC=C1)N1C(=C(C(=C1C(F)(F)F)C)C1=NC=C(N=C1)OC)C(=O)N1CCOCC1 RHJAQQOPSKUIRQ-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13005933 | 2013-12-19 | ||
| EP13005933.0 | 2013-12-19 | ||
| PCT/EP2014/003430 WO2015090600A1 (en) | 2013-12-19 | 2014-12-18 | Fluoromethyl-substituted pyrrole carboxamides as cav2.2 calcium channel blockers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016540820A JP2016540820A (ja) | 2016-12-28 |
| JP2016540820A5 true JP2016540820A5 (enExample) | 2018-02-01 |
Family
ID=49882759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016541134A Pending JP2016540820A (ja) | 2013-12-19 | 2014-12-18 | ＣａＶ２．２カルシウムチャネルブロッカーとしてのフルオロメチル置換ピロールカルボキサミド |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9562036B2 (enExample) |
| EP (1) | EP3083612A1 (enExample) |
| JP (1) | JP2016540820A (enExample) |
| AR (1) | AR098845A1 (enExample) |
| AU (1) | AU2014365741A1 (enExample) |
| CA (1) | CA2934327A1 (enExample) |
| MX (1) | MX2016007956A (enExample) |
| TW (1) | TW201609691A (enExample) |
| WO (1) | WO2015090600A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3083597B1 (en) * | 2013-12-19 | 2017-11-22 | Grünenthal GmbH | Fluoromethyl-substituted pyrrole carboxamides as cav2.2 calcium channel blockers |
| WO2015090599A1 (en) | 2013-12-19 | 2015-06-25 | Grünenthal GmbH | Fluoromethyl-substituted pyrrole carboxamides iv |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477463A (en) * | 1982-05-10 | 1984-10-16 | E. I. Du Pont De Nemours And Company | Antiinflammatory and/or analgesic 1-alkyl-4,5-diaryl-2-fluoroalkyl-1H-pyrroles |
| DE102006027229A1 (de) * | 2006-06-09 | 2007-12-20 | Grünenthal GmbH | 1,3-Disubstituierte 4-Methyl-1H-pyrrol-2-carbonsäureamide und ihre Verwendung zur Herstellung von Arzneimitteln |
| EP2590953B1 (en) | 2010-07-09 | 2014-10-29 | Convergence Pharmaceuticals Limited | Tetrazole compounds as calcium channel blockers |
| CA2842916A1 (en) * | 2011-07-26 | 2013-01-31 | Grunenthal Gmbh | Substituted heteroaromatic pyrazole-containing carboxamide and urea derivatives as vanilloid receptor ligands |
| TW201416348A (zh) * | 2012-08-29 | 2014-05-01 | Gruenenthal Chemie | 以氟甲基取代之吡咯甲醯胺 |
| EP3083597B1 (en) | 2013-12-19 | 2017-11-22 | Grünenthal GmbH | Fluoromethyl-substituted pyrrole carboxamides as cav2.2 calcium channel blockers |
| WO2015090599A1 (en) | 2013-12-19 | 2015-06-25 | Grünenthal GmbH | Fluoromethyl-substituted pyrrole carboxamides iv |
-
2014
- 2014-12-18 MX MX2016007956A patent/MX2016007956A/es unknown
- 2014-12-18 AU AU2014365741A patent/AU2014365741A1/en not_active Abandoned
- 2014-12-18 EP EP14821512.2A patent/EP3083612A1/en not_active Withdrawn
- 2014-12-18 WO PCT/EP2014/003430 patent/WO2015090600A1/en not_active Ceased
- 2014-12-18 CA CA2934327A patent/CA2934327A1/en not_active Abandoned
- 2014-12-18 JP JP2016541134A patent/JP2016540820A/ja active Pending
- 2014-12-19 AR ARP140104776A patent/AR098845A1/es unknown
- 2014-12-19 TW TW103144423A patent/TW201609691A/zh unknown
-
2016
- 2016-06-17 US US15/185,124 patent/US9562036B2/en not_active Expired - Fee Related
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