US 11,834,452 B2
CXCR7 antagonists
Junfa Fan, Palo Alto, CA (US); Antoni Krasinski, Sunnyvale, CA (US); Christopher W. Lange, Hayward, CA (US); Rebecca M. Lui, Mountain View, CA (US); Jeffrey P. McMahon, San Francisco, CA (US); Jay P. Powers, Pacifica, 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 May 27, 2021, as Appl. No. 17/331,750.
Application 17/331,750 is a continuation of application No. 16/379,599, filed on Apr. 9, 2019, granted, now 11,059,825.
Application 16/379,599 is a continuation of application No. 15/692,739, filed on Aug. 31, 2017, granted, now 10,287,292, issued on May 14, 2019.
Application 15/692,739 is a continuation of application No. 14/836,172, filed on Aug. 26, 2015, granted, now 9,783,544, issued on Oct. 10, 2017.
Application 14/836,172 is a continuation of application No. 14/091,641, filed on Nov. 27, 2013, granted, now 9,169,261, issued on Oct. 27, 2015.
Claims priority of provisional application 61/731,463, filed on Nov. 29, 2012.
Prior Publication US 2022/0127272 A1, Apr. 28, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 487/04 (2006.01); A61K 51/04 (2006.01); G01N 33/574 (2006.01)
CPC C07D 487/04 (2013.01) [A61K 51/0459 (2013.01); G01N 33/57492 (2013.01); G01N 2333/7158 (2013.01)] 14 Claims
 
1. A compound having formula I

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, hydrate, N-oxide, isotopically enriched or enantiomerically enriched version or a rotamer thereof, wherein
each of ring vertices Xa, Xb and Xc is independently selected from the group consisting of N, NH, N(R2), O, CH and C(R2);
the subscript n is 0, 1 or 2;
Z is selected from the group consisting of

OG Complex Work Unit Chemistry
R1 is a member selected from the group consisting of H and C1-8 alkyl, wherein the alkyl portion is optionally substituted with halogen, —NRaRb, —ORa, —CO2Ra and —CONRaRb;
each R2 is independently selected from the group consisting of H and C1-4 alkyl;
R3 is a member selected from the group consisting of H, C1-8 alkyl, C1-8 haloalkyl, C1-8 hydroxyalkyl, —CO2Ra, —X—CO2Ra, —CONRaRb and —X—CONRaRb;
each R4, when present, is a member independently selected from the group consisting of C1-8 alkyl, C1-8 haloalkyl, C1-8 hydroxyalkyl, —ORa, —CO2Ra, —X—CO2Ra, —NRaRb, —CONRaRb and —X—CONRaRb;
R5 is selected from the group consisting of substituted aryl, heteroaryl, cycloalkyl, and heterocycloalkyl optionally further substituted with 1-3 Ra;
each Ra and Rb is independently selected from the group consisting of hydrogen, hydroxyl, halogen, cyano, C1-8 alkyl, C1-8 alkoxy, C1-8 haloalkyl, C3-6 cycloalkyl, C3-6 cycloalkylalkyl, amino, C1-8 alkylamino, di C1-8 alkylamino, carboxamide, carboxy C1-4 alkyl ester, carboxylic acid, and —SO2— C1-8 alkyl;
each X is a C1-4 alkylene linking group or a linking group having the formula —(CH2)mO(CH2)p—, wherein the subscripts m and p are integer of from 0 to 5, and m+p is from 0 to 6, wherein any of the methylene portions of X are optionally substituted with one or two methyl groups.