US 12,234,221 B2
Pyridine carboxamide compounds for inhibiting NAV1.8
Michael Poslusney, Owings Mills, MD (US); Glen Ernst, Bear, DE (US); James Barrow, Arnold, MD (US); and Yifang Huang, Baltimore, MD (US)
Assigned to Lieber Institute, Inc., Baltimore, MD (US)
Appl. No. 17/256,781
Filed by Lieber Institute, Inc., Baltimore, MD (US)
PCT Filed Jul. 9, 2019, PCT No. PCT/US2019/041029
§ 371(c)(1), (2) Date Dec. 29, 2020,
PCT Pub. No. WO2020/014246, PCT Pub. Date Jan. 16, 2020.
Claims priority of provisional application 62/695,571, filed on Jul. 9, 2018.
Prior Publication US 2022/0227732 A1, Jul. 21, 2022
Int. Cl. C07D 401/12 (2006.01); A61K 31/44 (2006.01); A61K 31/4439 (2006.01); A61K 31/444 (2006.01); A61K 31/51 (2006.01); C07D 213/82 (2006.01); C07D 413/12 (2006.01); C07D 417/12 (2006.01)
CPC C07D 401/12 (2013.01) [A61K 31/44 (2013.01); A61K 31/4439 (2013.01); A61K 31/444 (2013.01); A61K 31/51 (2013.01); C07D 213/82 (2013.01); C07D 413/12 (2013.01); C07D 417/12 (2013.01)] 12 Claims
 
1. A compound of formula (I-H-i):

OG Complex Work Unit Chemistry
wherein:
R1 is selected from the group consisting of phenyl, pyridyl, and 1,3-benzothiazol-4yl, wherein the phenyl and pyridyl can be unsubstituted or substituted with one or more of halogen, C1-C8 alkyl, —O—R5, wherein R5 is selected from the group consisting of C1-C8 alkyl, —CF3, —CHF2, and —(CH2)p—CF3, wherein p is an integer selected from the group consisting of 1, 2, 3, 4, 5, 6, 7, and 8, —S—CF3, —NR6R7, wherein R6 and R7 are selected from the group consisting of H and C1-C4 alkyl;
R3 and R4 are H or —CF3, provided that if R3 is H, then R4 is —CF3 and if R4 is H, then R3 is —CF3;
R14 is C1-C4 alkyl; and
R15 is O or NR10, wherein R10 is H or C1-C4 alkyl.