US 12,152,026 B2
Transglutaminase 2 (TG2) inhibitors
David Campbell, La Jolla, CA (US); Justin Chapman, La Jolla, CA (US); Mui Cheung, Collegeville, PA (US); Thomas R. Diraimondo, La Jolla, CA (US); and Sergio G. Duron, La Jolla, CA (US)
Assigned to Sitari Pharma, Inc., Wilmington, DE (US)
Appl. No. 17/267,110
Filed by Sitari Pharma, Inc., La Jolla, CA (US)
PCT Filed Aug. 9, 2019, PCT No. PCT/US2019/045827
§ 371(c)(1), (2) Date Feb. 9, 2021,
PCT Pub. No. WO2020/033784, PCT Pub. Date Feb. 13, 2020.
Claims priority of provisional application 62/717,697, filed on Aug. 10, 2018.
Claims priority of provisional application 62/845,229, filed on May 8, 2019.
Prior Publication US 2021/0163480 A1, Jun. 3, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 471/04 (2006.01)
CPC C07D 471/04 (2013.01) 27 Claims
 
1. A compound according to Formula (I) or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein:

OG Complex Work Unit Chemistry
 is a 9-membered bicyclic heteroaryl ring;
X, Y, and Z are selected from ═C(R11)— or ═N—, wherein at least two of X, Y, and Z are ═C(R11)—;
R1 and R2 are independently selected from H or optionally substituted alkyl; or R1 and R2, together with the nitrogen to which they are attached, form an optionally substituted 3-, 4-, 5- or 6-membered heterocycloalkyl ring;
R3 is —N(H)C(O)OR5, —OC(O)NR6R7, —N(H)C(O)NR6R7, or —N(H)C(O)R8;
each R4 is independently selected from halogen, —CN, —OR9, —SR9, —N(R10)2, —S(O)R9, —S(O)2R9, —NHS(O)2R9, —S(O)2N(R10)2, —C(O)R9, —C(O)OR9, —OC(O)R9, —C(O)N(R10)2, —OC(O)N(R10)2, —NR10C(O)N(R10)2, —NR10C(O)R9, —NR10C(O)OR9, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted phenyl, or optionally substituted heteroaryl;
R5 is selected from optionally substituted alkyl, optionally substituted heterocycloalkyl, optionally substituted phenyl, or optionally substituted heteroaryl;
R6 and R7 are independently selected from H or optionally substituted alkyl; or R6 and R7, together with the nitrogen to which they are attached, form an optionally substituted 5- or 6-membered heterocycloalkyl ring;
R8 is selected from optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted heterocycloalkyl, or optionally substituted heteroaryl;
each R9 is independently selected from optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted phenyl, or optionally substituted heteroaryl;
each R10 is independently selected from H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted phenyl, or optionally substituted heteroaryl;
each R11 is independently selected from H, halogen, or optionally substituted alkyl;
n is 0, 1, 2, 3, or 4; and
p is 0, 1, or 2.