US 12,145,924 B2
Lysophosphatidic acid receptor 1 (LPAR1) inhibitor compounds
Tianwei Ma, Carmel, IN (US); Liang Wu, Shanghai (CN); and Xuejun Zhang, Shanghai (CN)
Assigned to ELI LILLY AND COMPANY, Indianapolis, IN (US)
Filed by Eli Lilly and Company, Indianapolis, IN (US)
Filed on May 18, 2022, as Appl. No. 17/747,261.
Application 17/747,261 is a division of application No. 16/633,371, granted, now 11,365,185, previously published as PCT/US2018/048249, filed on Aug. 28, 2018.
Claims priority of application No. PCT/CN2017/100354 (WO), filed on Sep. 4, 2017.
Prior Publication US 2022/0281845 A1, Sep. 8, 2022
Int. Cl. A61P 1/16 (2006.01); C07D 401/14 (2006.01); C07D 403/12 (2006.01); C07D 403/14 (2006.01)
CPC C07D 401/14 (2013.01) [A61P 1/16 (2018.01); C07D 403/12 (2013.01); C07D 403/14 (2013.01)] 10 Claims
 
1. A method for treating nonalcoholic steatohepatitis (NASH) comprising administering to a mammal in need thereof, an effective amount of a compound of the formula

OG Complex Work Unit Chemistry
wherein,
X1 and X2 are each independently CH or N, and X3 is C-R2 or N, provided that when X1 is CH, then X2 is CH and X3 is C-R2, and provided that when X1 is N, then only one of X2 or X3 may be N;
Y1 and Y2 are CH or N, provided that only one of Y1 or Y2 may be N;
R1 is
isopropyl,
isobutyl,
t-butyl,
2-hydroxypropyl-2-yl,
cyclopropyl,
cyclopropyloxy,
t-butyloxy,
cyclobutyloxy,
3,3-difluorocyclobutyloxy,
2-fluoropropyl-2-yl,
1, 1-difluoroethyl,
trifluoromethyl,
isopropyloxy, or
2-methoxypropyl-2-yl;
R2 is H or fluoro;
R3 is H, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkoxymethyl, CF3, or cyano;
R4 is H, halogen, C1-C3 alkyl, or CF3;
R5 is H, methyl, ethyl, propyl, isopropyl, or cyclopropyl; or
a pharmaceutically acceptable salt thereof.