US 11,834,436 B2
Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
Guoqiang Wang, Belmont, MA (US); Ruichao Shen, Belmont, MA (US); Brett Granger, Sudbury, MA (US); Jing He, Somerville, MA (US); Xuechao Xing, Wilmington, MA (US); Yong He, Lexington, MA (US); Jiang Long, Wayland, MA (US); Jun Ma, Wayland, MA (US); Bin Wang, Newton, MA (US); and Yat Sun Or, Waltham, MA (US)
Assigned to Enanta Pharmaceuticals, Inc., Watertown, MA (US)
Filed by ENANTA PHARMACEUTICALS, INC., Watertown, MA (US)
Filed on Apr. 13, 2021, as Appl. No. 17/228,815.
Application 17/228,815 is a division of application No. 16/400,529, filed on May 1, 2019, granted, now 11,008,304.
Claims priority of provisional application 62/665,789, filed on May 2, 2018.
Prior Publication US 2022/0119366 A1, Apr. 21, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/14 (2006.01); C07D 413/14 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 417/14 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01)] 5 Claims
 
1. A method for treating an ASK-1 mediated disease or condition in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound represented by Formula I or a pharmaceutically acceptable salt or ester thereof:

OG Complex Work Unit Chemistry
wherein

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 is selected from the groups below

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R1 is selected from the group consisting of:

OG Complex Work Unit Chemistry
R2 is

OG Complex Work Unit Chemistry
X is N or C—R3;
R3 is selected from the group consisting of:
1) Hydrogen;
2) Halogen;
2) —C1-C8 alkyl;
4) -halo-C1-C8-alkyl; and
5) C1-C8 alkoxyl; and
R4 is selected from the group consisting of

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein said ASK-1 mediated disease or condition is selected from the group consisting of nonalcoholic fatty liver disease, nonalcoholic steatohepatitis, diabetic nephropathy, myocardial ischemia, and glomerulonephritis.