US 11,884,654 B2
Substituted anilines as CCR(4) antagonists
Trevor T. Charvat, San Jose, CA (US); Junfa Fan, Palo Alto, CA (US); Christopher W. Lange, Hayward, CA (US); Manmohan Reddy Leleti, Dublin, CA (US); Yandong Li, San Diego, CA (US); Venkat Reddy Mali, Cupertino, CA (US); Jeffrey P. McMahon, San Francisco, CA (US); Jay Powers, Pacifica, CA (US); Sreenivas Punna, Sunnyvale, CA (US); and Ju Yang, Palo Alto, CA (US)
Assigned to CHEMOCENTRYX, INC., Thousand Oaks, CA (US)
Filed by CHEMOCENTRYX, INC., San Carlos, CA (US)
Filed on Sep. 9, 2021, as Appl. No. 17/470,464.
Application 15/207,315 is a division of application No. 14/452,341, filed on Aug. 5, 2014, granted, now 9,567,323, issued on Feb. 14, 2017.
Application 17/470,464 is a continuation of application No. 16/526,338, filed on Jul. 30, 2019, granted, now 11,142,521.
Application 16/526,338 is a continuation of application No. 15/674,230, filed on Aug. 10, 2017, granted, now 10,407,417, issued on Sep. 10, 2019.
Application 15/674,230 is a continuation of application No. 15/207,315, filed on Jul. 11, 2016, granted, now 9,758,512, issued on Sep. 12, 2017.
Application 14/452,341 is a continuation of application No. 13/691,571, filed on Nov. 30, 2012, granted, now 8,835,419, issued on Sep. 16, 2014.
Claims priority of provisional application 61/565,968, filed on Dec. 1, 2011.
Prior Publication US 2022/0194929 A1, Jun. 23, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A01N 43/00 (2006.01); A61K 31/00 (2006.01); C07D 413/06 (2006.01); C07D 401/04 (2006.01); C07D 401/06 (2006.01); C07D 403/06 (2006.01); C07D 405/06 (2006.01); C07D 417/04 (2006.01); C07D 211/56 (2006.01); C07D 295/135 (2006.01); C07D 211/62 (2006.01); C07D 211/26 (2006.01); C07D 211/70 (2006.01); C07D 241/04 (2006.01); C07D 207/16 (2006.01); C07D 211/34 (2006.01); A61K 31/451 (2006.01); A61K 31/454 (2006.01); A61K 31/4545 (2006.01); A61K 31/495 (2006.01); A61K 31/496 (2006.01); A61K 31/5377 (2006.01)
CPC C07D 413/06 (2013.01) [A61K 31/451 (2013.01); A61K 31/454 (2013.01); A61K 31/4545 (2013.01); A61K 31/495 (2013.01); A61K 31/496 (2013.01); A61K 31/5377 (2013.01); C07D 207/16 (2013.01); C07D 211/26 (2013.01); C07D 211/34 (2013.01); C07D 211/56 (2013.01); C07D 211/62 (2013.01); C07D 211/70 (2013.01); C07D 241/04 (2013.01); C07D 295/135 (2013.01); C07D 401/04 (2013.01); C07D 401/06 (2013.01); C07D 403/06 (2013.01); C07D 405/06 (2013.01); C07D 417/04 (2013.01)] 15 Claims
 
1. A pharmaceutical composition comprising a compound of formula (Ic)

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient,
wherein
X and Y are each N;
Z is CH;
Q is CH or N;
R1 is selected from hydrogen, C1-8 alkyl, C1-8 haloalkyl, and halogen;
each R2 is a member selected from the group consisting of C1-8 alkyl, C1-8 haloalkyl, halogen and —CN;
R4 is hydrogen or methyl;
R6 is absent or is a member selected from the group consisting of H, —OH, C1-8 alkyl, C1-8 hydroxyalkyl, C1-4 alkoxy-C1-4 alkyl, —C(O)NRaRb, —CO2H, —C(O)ORa, —C(O)Ra, and —SO2Ra;
R7 is absent or is selected from the group consisting of H, C1-8 alkyl and C1-8 haloalkyl;
each Ra and Rb are independently selected from the group consisting of hydrogen, C1-8 alkyl, C1-8 hydroxyalkyl, C1-8 haloalkyl, and C1-8 alkoxy; and
the subscript n is 1.