US 12,268,675 B2
Diaryl substituted 6,5-fused ring compounds as C5aR inhibitors
Pingchen Fan, Hayward, CA (US); Christopher W. Lange, Hayward, CA (US); Viengkham Malathong, Mountain View, CA (US); Venkat Reddy Mali, Cupertino, CA (US); Sreenivas Punna, Sunnyvale, CA (US); Hiroko Tanaka, Mountain View, CA (US); Yibin Zeng, Foster City, CA (US); and Penglie Zhang, Foster City, CA (US)
Assigned to CHEMOCENTRYX, INC., Thousand Oaks, CA (US)
Filed by CHEMOCENTRYX, INC., San Carlos, CA (US)
Filed on Sep. 13, 2022, as Appl. No. 17/931,801.
Application 17/033,124 is a division of application No. 16/226,865, filed on Dec. 20, 2018, granted, now 10,828,285, issued on Nov. 10, 2020.
Application 17/931,801 is a continuation of application No. 17/033,124, filed on Sep. 25, 2020, granted, now 11,478,460.
Claims priority of provisional application 62/609,834, filed on Dec. 22, 2017.
Prior Publication US 2023/0115912 A1, Apr. 13, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/437 (2006.01); A61P 9/00 (2006.01); A61P 35/00 (2006.01); A61P 37/00 (2006.01); A61K 45/06 (2006.01)
CPC A61K 31/437 (2013.01) [A61P 9/00 (2018.01); A61P 35/00 (2018.01); A61P 37/00 (2018.01); A61K 45/06 (2013.01)] 16 Claims
 
1. A method of treating a human suffering from or susceptible to a disease or disorder selected from the group consisting of microscopic polyangiitis, C3-glomerulonephritis, rheumatoid arthritis, systemic lupus erythematosus, lupus nephritis, lupus glomerulonephritis, vasculitis, ANCA vasculitis, immuno vasculitis, Graft versus host disease, glomerulonephritis,
comprising administering to the mammal a therapeutically effective amount of a compound of Formula (I)

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein,
X1 is selected from the group consisting of a bond, C1-8 alkylene, C(O), C(O)—C1-4 alkylene, and S(O)2;
R1 is pyridyl
wherein the group —X1—R1 is optionally substituted with 1 to 5 Rx substituents;
R2a and R2e are each independently selected from the group consisting of hydrogen, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, —O—C1-6 haloalkyl, —S—C1-6 alkyl, —C1-6 alkyl-O—C1-6 alkyl, —C1-6 alkyl-S—C1-6 alkyl, CN, and halogen, and at least one of R2a and R2e is other than hydrogen;
R2b, R2c, and R2d are each independently selected from the group consisting of hydrogen, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, —O—C1-6 haloalkyl, —S—C1-6 alkyl, —C1-6 alkyl-O—C1-6 alkyl, —C1-6 alkyl-S—C1-6 alkyl, cyano, and halogen;
each R3 is independently selected from the group consisting of hydroxyl, C1-4 alkyl, C1-4 haloalkyl and C1-4 hydroxyalkyl, and optionally two R3 groups on the same carbon atom are combined to form oxo (═O);
R4 is independently selected from the group consisting of —X2—OR4a, —X2—NR4aR4b, —X2—CONR4aR4b, —X2—NR4a—C(O)R4a, —X2—NR4a—C(O)NR4aR4b, —X2—NR4a—C(O)OR4a, —X2—NR4a—C(O)—C1-3 alkylene-OR4a and —X2—NR4a—C(O)—C1-3 alkylene-NR4aR4b, wherein each X2 is independently a bond, C(O), C1-4 alkylene, C(O)—C1-4 alkylene, and C1-4 alkylene-C(O), and each R4a and R4b is independently selected from the group consisting of hydrogen, C1-4 alkyl, and C1-4 haloalkyl;
each R5 is independently selected from the group consisting of C1-8 alkyl, C1-8 alkoxy, C1-8 haloalkyl, C1-8 haloalkoxy, C1-8 hydroxyalkyl, halogen, OH, CN, C(O)R5a and CO2R5a, wherein each R5a is independently selected from the group consisting of hydrogen, C1-4 alkyl, and C1-4 haloalkyl;
each Rx is independently selected from the group consisting of halogen, CN, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, C1-4 hydroxy, C2-4 alkenyl, C3-6 cycloalkyl, CO2—C1-4 alkyl, and CONH2;
the subscript m is 0, 1, 2, 3 or 4; and
the subscript n is 0, 1, 2 or 3.