JP2018516873A5 - - Google Patents
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- Publication number
- JP2018516873A5 JP2018516873A5 JP2017555639A JP2017555639A JP2018516873A5 JP 2018516873 A5 JP2018516873 A5 JP 2018516873A5 JP 2017555639 A JP2017555639 A JP 2017555639A JP 2017555639 A JP2017555639 A JP 2017555639A JP 2018516873 A5 JP2018516873 A5 JP 2018516873A5
- Authority
- JP
- Japan
- Prior art keywords
- benzamide
- formula
- tert
- butyl
- compound
- 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
- 150000001875 compounds Chemical class 0.000 claims 36
- -1 CF 3 Chemical group 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 14
- 239000002253 acid Substances 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 230000003287 optical effect Effects 0.000 claims 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 208000020925 Bipolar disease Diseases 0.000 claims 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 4
- 208000029560 autism spectrum disease Diseases 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 2
- GXFFOSYQAHEIGK-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(2-cyclopropylimidazol-1-yl)-N-(2-methylbutan-2-yl)benzamide Chemical compound ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(CC)C)C=C(C=1)N1C(=NC=C1)C1CC1 GXFFOSYQAHEIGK-UHFFFAOYSA-N 0.000 claims 1
- ZLVLRABZIUQUKH-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(2-cyclopropylimidazol-1-yl)-N-(3-methyl-1,1-dioxothiolan-3-yl)benzamide Chemical compound ClC1=CC=C(C=C1)C=1C=C(C(=O)NC2(CS(CC2)(=O)=O)C)C=C(C=1)N1C(=NC=C1)C1CC1 ZLVLRABZIUQUKH-UHFFFAOYSA-N 0.000 claims 1
- IAPVDOMJGPJZAG-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(2-methylimidazol-1-yl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide Chemical compound ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C(F)(F)F)(C)C)C=C(C=1)N1C(=NC=C1)C IAPVDOMJGPJZAG-UHFFFAOYSA-N 0.000 claims 1
- DETYJJJOTRMBOU-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(2-propan-2-ylimidazol-1-yl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide Chemical compound ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C(F)(F)F)(C)C)C=C(C=1)N1C(=NC=C1)C(C)C DETYJJJOTRMBOU-UHFFFAOYSA-N 0.000 claims 1
- DVDTYBDLYFFAAY-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-[2-(hydroxymethyl)imidazol-1-yl]-N-(2-methylbutan-2-yl)benzamide Chemical compound ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(CC)C)C=C(C=1)N1C(=NC=C1)CO DVDTYBDLYFFAAY-UHFFFAOYSA-N 0.000 claims 1
- TXSKFNDDLNOCRW-UHFFFAOYSA-N 3-(4-chlorophenyl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-(2-propan-2-ylimidazol-1-yl)benzamide Chemical compound ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(CO)(C)C)C=C(C=1)N1C(=NC=C1)C(C)C TXSKFNDDLNOCRW-UHFFFAOYSA-N 0.000 claims 1
- VJAKNODKZHHGAZ-UHFFFAOYSA-N 3-(4-chlorophenyl)-N-(3-methyl-1,1-dioxothiolan-3-yl)-5-(2-propan-2-ylimidazol-1-yl)benzamide Chemical compound ClC1=CC=C(C=C1)C=1C=C(C(=O)NC2(CS(CC2)(=O)=O)C)C=C(C=1)N1C(=NC=C1)C(C)C VJAKNODKZHHGAZ-UHFFFAOYSA-N 0.000 claims 1
- YFJMVOQSEBBZRB-UHFFFAOYSA-N C(C)(C)(C)NC(C1=CC(=CC(=C1)N1C(=NC=C1)C(C)C)C1=CC(=C(C=C1)C)F)=O.C(C)(C)(C)NC(C1=CC(=CC(=C1)C1=CC=C(C=C1)C(F)(F)F)N1C(=NC=C1)C(C)C)=O Chemical compound C(C)(C)(C)NC(C1=CC(=CC(=C1)N1C(=NC=C1)C(C)C)C1=CC(=C(C=C1)C)F)=O.C(C)(C)(C)NC(C1=CC(=CC(=C1)C1=CC=C(C=C1)C(F)(F)F)N1C(=NC=C1)C(C)C)=O YFJMVOQSEBBZRB-UHFFFAOYSA-N 0.000 claims 1
- JLBDBNKDDXYVEX-UHFFFAOYSA-N C1(CC1)C(C)(C)NC(C1=CC(=CC(=C1)C1=CC=C(C=C1)F)N1C(=NC=C1)CC)=O.C1(CC1)C(C)(C)NC(C1=CC(=CC(=C1)N1C(=NC=C1)C(C)C)C1=CC=C(C=C1)F)=O Chemical compound C1(CC1)C(C)(C)NC(C1=CC(=CC(=C1)C1=CC=C(C=C1)F)N1C(=NC=C1)CC)=O.C1(CC1)C(C)(C)NC(C1=CC(=CC(=C1)N1C(=NC=C1)C(C)C)C1=CC=C(C=C1)F)=O JLBDBNKDDXYVEX-UHFFFAOYSA-N 0.000 claims 1
- KOGBLIKNRUSYNJ-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(C)C2CC2)C=C(C1)N1C(=NC=C1)C1CC1.ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(C)C2CC2)C=C(C1)N1C(=NC=C1)C Chemical compound ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(C)C2CC2)C=C(C1)N1C(=NC=C1)C1CC1.ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(C)C2CC2)C=C(C1)N1C(=NC=C1)C KOGBLIKNRUSYNJ-UHFFFAOYSA-N 0.000 claims 1
- XTLHPZWFEBUJGH-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(C)C2CC2)C=C(C1)N1C(=NC=C1)CC.ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(C)C2CC2)C=C(C1)N1C(=NC=C1)C(C)C Chemical compound ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(C)C2CC2)C=C(C1)N1C(=NC=C1)CC.ClC1=CC=C(C=C1)C=1C=C(C(=O)NC(C)(C)C2CC2)C=C(C1)N1C(=NC=C1)C(C)C XTLHPZWFEBUJGH-UHFFFAOYSA-N 0.000 claims 1
- OFKLVDQQRFAOQJ-UHFFFAOYSA-N N-tert-butyl-3-(2-tert-butylimidazol-1-yl)-5-(4-fluorophenyl)benzamide Chemical compound C(C)(C)(C)NC(C1=CC(=CC(=C1)C1=CC=C(C=C1)F)N1C(=NC=C1)C(C)(C)C)=O OFKLVDQQRFAOQJ-UHFFFAOYSA-N 0.000 claims 1
- HWBHVYNFUOUDRO-UHFFFAOYSA-N N-tert-butyl-3-(3,4-difluorophenyl)-5-(2-propan-2-ylimidazol-1-yl)benzamide Chemical compound C(C)(C)(C)NC(C1=CC(=CC(=C1)N1C(=NC=C1)C(C)C)C1=CC(=C(C=C1)F)F)=O HWBHVYNFUOUDRO-UHFFFAOYSA-N 0.000 claims 1
- PQEMNVYOUDLEGS-UHFFFAOYSA-N N-tert-butyl-3-(4-chlorophenyl)-5-[2-(2-hydroxypropan-2-yl)imidazol-1-yl]benzamide Chemical compound C(C)(C)(C)NC(C1=CC(=CC(=C1)N1C(=NC=C1)C(C)(C)O)C1=CC=C(C=C1)Cl)=O PQEMNVYOUDLEGS-UHFFFAOYSA-N 0.000 claims 1
- HPHWUZXYJHXBOH-UHFFFAOYSA-N N-tert-butyl-3-[2-(2-hydroxypropan-2-yl)imidazol-1-yl]-5-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C(C)(C)(C)NC(C1=CC(=CC(=C1)C1=CC=C(C=C1)C(F)(F)F)N1C(=NC=C1)C(C)(C)O)=O HPHWUZXYJHXBOH-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- HPBROFGYTXOJIO-UHFFFAOYSA-N propan-2-ylcyclopropane Chemical compound CC(C)C1CC1 HPBROFGYTXOJIO-UHFFFAOYSA-N 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 0 CC(*)(NC(c1cc(-[n]2c(C)ncc2)cc(-c2cc(*)c(*)cc2)c1)=O)I Chemical compound CC(*)(NC(c1cc(-[n]2c(C)ncc2)cc(-c2cc(*)c(*)cc2)c1)=O)I 0.000 description 13
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15170671.0 | 2015-06-04 | ||
| EP15170671 | 2015-06-04 | ||
| PCT/EP2016/062204 WO2016193235A1 (en) | 2015-06-04 | 2016-05-31 | Imidazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018516873A JP2018516873A (ja) | 2018-06-28 |
| JP2018516873A5 true JP2018516873A5 (enExample) | 2019-06-27 |
| JP6877359B2 JP6877359B2 (ja) | 2021-05-26 |
Family
ID=53284112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017555639A Expired - Fee Related JP6877359B2 (ja) | 2015-06-04 | 2016-05-31 | イミダゾール誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10029989B2 (enExample) |
| EP (1) | EP3303299B1 (enExample) |
| JP (1) | JP6877359B2 (enExample) |
| CN (1) | CN107531642B (enExample) |
| AR (1) | AR104863A1 (enExample) |
| TW (1) | TW201718511A (enExample) |
| WO (1) | WO2016193235A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10577332B2 (en) | 2015-04-23 | 2020-03-03 | Hoffmann-La Roche Inc. | Tetrazole derivatives |
| WO2017060202A1 (en) | 2015-10-06 | 2017-04-13 | F. Hoffmann-La Roche Ag | Triazole derivatives |
| EP3411365B1 (en) | 2016-02-02 | 2019-11-20 | H. Hoffnabb-La Roche Ag | Pyrazol-pyridine derivatives as eaat3 inhibitors |
| CN109071451B (zh) * | 2016-05-27 | 2022-07-15 | 豪夫迈·罗氏有限公司 | 作为eaat3抑制剂的吡唑化合物 |
| WO2018069362A1 (en) | 2016-10-14 | 2018-04-19 | F. Hoffmann-La Roche Ag | Imidazole compounds as eaat3 inhibitors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7939556B2 (en) * | 2005-10-14 | 2011-05-10 | Neurosearch A/S | Imidazole derivatives and their use for modulating the GABAA receptor complex |
| ES2596706T3 (es) * | 2006-06-29 | 2017-01-11 | F. Hoffmann-La Roche Ag | Arilamidas con sustitución de tetrazol |
| WO2009058298A1 (en) * | 2007-10-31 | 2009-05-07 | Merck & Co., Inc. | P2x3, receptor antagonists for treatment of pain |
| ES2570628T3 (es) * | 2007-12-17 | 2016-05-19 | Hoffmann La Roche | Nuevas arilamidas con sustitución imidazol |
| US10577332B2 (en) * | 2015-04-23 | 2020-03-03 | Hoffmann-La Roche Inc. | Tetrazole derivatives |
-
2016
- 2016-05-31 CN CN201680022475.8A patent/CN107531642B/zh not_active Expired - Fee Related
- 2016-05-31 WO PCT/EP2016/062204 patent/WO2016193235A1/en not_active Ceased
- 2016-05-31 JP JP2017555639A patent/JP6877359B2/ja not_active Expired - Fee Related
- 2016-05-31 EP EP16726087.6A patent/EP3303299B1/en not_active Not-in-force
- 2016-06-02 AR ARP160101615A patent/AR104863A1/es unknown
- 2016-06-03 TW TW105117674A patent/TW201718511A/zh unknown
-
2017
- 2017-12-04 US US15/830,399 patent/US10029989B2/en active Active
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