US 12,492,185 B2
Benzimidazole derivatives and their uses
Nagasree Chakka, Thousand Oaks, CA (US); Hua Gao, Thousand Oaks, CA (US); Angel Guzman-Perez, Thousand Oaks, CA (US); Brett Michael Johnson, Thousand Oaks, CA (US); Madeleine Kieffer, Thousand Oaks, CA (US); Justin Malinowski, Thousand Oaks, CA (US); and Laurie Schenkel, Thousand Oaks, CA (US)
Assigned to Teijin Pharma Limited, Tokyo (JP)
Appl. No. 17/602,028
Filed by Teijin Pharma Limited, Tokyo (JP)
PCT Filed Apr. 10, 2020, PCT No. PCT/US2020/027624
§ 371(c)(1), (2) Date Oct. 7, 2021,
PCT Pub. No. WO2020/210597, PCT Pub. Date Oct. 15, 2020.
Claims priority of provisional application 62/832,374, filed on Apr. 11, 2019.
Prior Publication US 2022/0204477 A1, Jun. 30, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/14 (2006.01)
CPC C07D 401/14 (2013.01) 5 Claims
 
1. A compound or a salt thereof selected from
(3R,4R)-4-fluoro-1-(5-fluoro-1-((5-fluoro-2-pyridinyl) methyl)-1H-benzimidazol-2-yl)-3-piperidinamine;
(3R)-1-(5,7-difluoro-1-((5-fluoro-2-pyridinyl) methyl)-1H-benzimidazol-2-yl)-4,4-difluoro-3-piperidinamine;
(3R,4R)-4-fluoro-1-(6-fluoro-1-((5-fluoro-2-pyrimidinyl)methyl)-1H-benzimidazol-2-yl)-3-piperidinamine;
(3R,4R)-4-fluoro-1-(6-fluoro-1-((5-fluoro-2-pyridinyl)methyl)-1H-benzimidazol-2-yl)-3-piperidinamine;
(3R,4R)-1-(1-((5-chloro-2-pyridinyl)methyl)-5-fluoro-1H-benzimidazol-2-yl)-4-fluoro-3-piperidinamine;
(3R)-1-(1-((5-chloro-2-pyrimidinyl)methyl)-6-fluoro-1H-benzimidazol-2-yl)-4,4-difluoro-3-piperidinamine;
(3R)-4,4-difluoro-1-(6-fluoro-1-((5-fluoro-2-pyridinyl)methyl)-1H-benzimidazol-2-yl)-3-piperidinamine;
(3R,4R)-1-(5,6-difluoro-1-((5-methyl-2-pyridinyl)methyl)-1H-benzimidazol-2-yl)-4-fluoro-3-piperidinamine;
(3R,4R)-1-(4,6-difluoro-1-((5-methoxy-2-pyrimidinyl)methyl)-1H-benzimidazol-2-yl)-4-fluoro-3-piperidinamine;
(3R)-1-(1-((5-chloropyridin-2-yl)methyl)-6-fluoro-1H-benzimidazol-2-yl)-4,4-difluoropiperidin-3-amine;
(3R,4R)-4-fluoro-1-(5-fluoro-1-((5-fluoro-2-pyrimidinyl)methyl)-1H-benzimidazol-2-yl)-3-piperidinamine;
(3R,4R)-1-(1-((5-chloro-2-pyridinyl)methyl)-6-fluoro-1H-benzimidazol-2-yl)-4-fluoro-3-piperidinamine;
2-((3R)-3-amino-4,4-difluoro-1-piperidinyl)-1-((5-chloro-2-pyridinyl)methyl)-1H-benzimidazole-6-carbonitrile;
(3R)-1-(1-((5-chloro-2-pyrimidinyl)methyl)-4,6-difluoro-1H-benzimidazol-2-yl)-4,4-difluoro-3-piperidinamine;
2-((3R,4R)-3-amino-4-fluoro-1-piperidinyl)-6-fluoro-1-((5-fluoro-2-pyridinyl)methyl)-1H-benzimidazole-4-carbonitrile;
(3R)-1-(1-((5-chloro-2-pyridinyl)methyl)-5,6-difluoro-1H-benzimidazol-2-yl)-4,4-difluoro-3-piperidinamine;
(3R)-1-(1-((5-chloro-2-pyrimidinyl)methyl)-5,6-difluoro-1H-benzimidazol-2-yl)-4,4-difluoro-3-piperidinamine;
(3R,4R)-1-(1-((5-chloro-2-pyrimidinyl)methyl)-5,6-difluoro-1H-benzimidazol-2-yl)-4-fluoro-3-piperidinamine;
(3R,4R)-1-(5,6-difluoro-1-((5-methoxy-2-pyrimidinyl)methyl)-1H-benzimidazol-2-yl)-4-fluoro-3-piperidinamine;
6-((2-((3R,4R)-3-amino-4-fluoro-1-piperidinyl)-5,6-difluoro-1H-benzimidazol-1-yl)methyl)-2-pyridinecarbonitrile;
and (3R,4R)-1-(1-((5-chloropyrimidin-2-yl)methyl)-4-fluoro-6-methoxy-1H-benzimidazol-2-yl)-4-fluoropiperidin-3-amine.