US 11,999,716 B2
WDR5 inhibitors and modulators
Taekyu Lee, Brentwood, TN (US); Joseph R. Alvarado, Cleveland Heights, OH (US); Jianhua Tian, Nashville, TN (US); Kenneth M. Meyers, Nashville, TN (US); Changho Han, Nashville, TN (US); Jonathan J. Mills, Nashville, TN (US); Kevin B. Teuscher, Nashville, TN (US); Shaun R. Stauffer, Brentwood, TN (US); Stephen W. Fesik, Nashville, TN (US); and Rocco D. Gogliotti, Kingston Springs, TN (US)
Assigned to Vanderbilt University, Nashville, TN (US)
Appl. No. 17/287,492
Filed by Vanderbilt University, Nashville, TN (US)
PCT Filed Oct. 24, 2019, PCT No. PCT/US2019/057877
§ 371(c)(1), (2) Date Apr. 21, 2021,
PCT Pub. No. WO2020/086857, PCT Pub. Date Apr. 30, 2020.
Claims priority of provisional application 62/749,768, filed on Oct. 24, 2018.
Prior Publication US 2023/0012362 A1, Jan. 12, 2023
Int. Cl. C07D 401/14 (2006.01); C07D 217/16 (2006.01); C07D 401/06 (2006.01); C07D 405/14 (2006.01); C07D 413/06 (2006.01); C07D 413/14 (2006.01); C07D 417/06 (2006.01); C07D 417/14 (2006.01); C07D 487/04 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 217/16 (2013.01); C07D 401/06 (2013.01); C07D 405/14 (2013.01); C07D 413/06 (2013.01); C07D 413/14 (2013.01); C07D 417/06 (2013.01); C07D 417/14 (2013.01); C07D 487/04 (2013.01)] 12 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
n is 1;
R1 is —(CRaRb)-G1;
G1 is a 6 or 5-membered aromatic ring optionally containing 1-2 nitrogen atoms, wherein G1 is substituted with 1-3 substituents independently selected from the group consisting of —OC1-4alkyl, C1-4alkyl, halogen, and C3-6cycloalkyl;
Ra is C1-4alkyl, C3-6cycloalkyl, or hydrogen;
Rb is hydrogen;
R2a, R2b, R3a, and R3b are each hydrogen;
R4 is a 5 or 6-membered aromatic ring optionally containing 1-2 nitrogen atoms, wherein R4 is substituted with 2, 1, or 3 substituents independently selected from the group consisting of C1-4haloalkyl, C1-4alkyl, and halogen;
R5 is hydrogen;
R6 is hydrogen;
R7a and R7b are each hydrogen; and
R8 is a 5-membered heterocyclic ring containing 2-3 heteroatoms and 2 or 1 double bonds, wherein one of the 2-3 heteroatoms is a nitrogen and the remaining heteroatoms are independently selected from nitrogen and oxygen, wherein R8 is optionally substituted with 1-3 substituents independently selected from the group consisting of C1-4alkyl, imino, C1-4haloalkyl, —NH(C1-4alkyl), halogen, cyano, NH2, —N(C1-4alkyl)2, C3-6cycloalkyl, and —C1-3alkylene-C3-6cycloalkyl.