US 11,718,613 B2
N-(phenylsulfonyl)benzamides and related compounds as Bcl-2 inhibitors
Shaomeng Wang, Superior Township, MI (US); and Jianyong Chen, Ann Arbor, MI (US)
Assigned to THE REGENTS OF THE UNIVERSITY OF MICHIGAN, Ann Arbor, MI (US)
Filed by THE REGENTS OF THE UNIVERSITY OF MICHIGAN, Ann Arbor, MI (US)
Filed on Sep. 17, 2020, as Appl. No. 17/23,426.
Application 17/023,426 is a continuation of application No. 16/317,056, granted, now 10,829,488, previously published as PCT/US2017/045428, filed on Aug. 4, 2017.
Claims priority of provisional application 62/454,101, filed on Feb. 3, 2017.
Claims priority of provisional application 62/371,504, filed on Aug. 5, 2016.
Prior Publication US 2021/0002277 A1, Jan. 7, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 471/04 (2006.01); A61P 35/02 (2006.01); A61P 35/00 (2006.01)
CPC C07D 471/04 (2013.01) [A61P 35/00 (2018.01); A61P 35/02 (2018.01)] 16 Claims
 
1. A compound, or a pharmaceutically acceptable salt thereof, having Formula I-A:

OG Complex Work Unit Chemistry
wherein:
A is selected from the group consisting of:

OG Complex Work Unit Chemistry
E is a carbon atom and the depicted dashed bond forms a double bond; or
E is a —C(H)— and the depicted dashed bond is absent to form a single bond; or
E is a nitrogen atom and the depicted dashed bond is absent to form a single bond;
X1, X2, and X3 are each —CR8═, or one of X1, X2, and X3 is —N═ and two X1, X2, and X3 are each —CR8;
R1a and R1b taken together with the carbon atom to which they are attached form

OG Complex Work Unit Chemistry
R2 is selected from the group consisting of —NO2, —SO2CH3, and —SO2CF3;
R3 is selected from the group consisting of hydrogen, —CN, —C≡CH, and —N(R4a)(R4b);
R2a is selected from the group consisting of hydrogen and halogen;
R4a is selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted C3-6 cycloalkyl, optionally substituted heterocyclo, optionally substitute heteroalkyl, optionally substituted (cycloalkyl)alkyl, and optionally substituted (heterocyclo)alkyl;
R4b is selected from the group consisting of hydrogen and C1-4 alkyl;
R5 is selected from the group consisting of is selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted heterocyclo, optionally substituted heteroalkyl, optionally substituted (cycloalkyl)alkyl, and optionally substituted (heterocyclo)alkyl;
R6a, R6c, R6e, R6f, and R6g are each independently selected from the group consisting of hydrogen, optionally substituted C1-6 alkyl, optionally substituted C3-6 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclo, optionally substituted heteroalkyl, optionally substituted (cycloalkyl)alkyl, and optionally substituted (heterocyclo)alkyl;
R6b and R6d are each independently selected from the group consisting of hydrogen, C1-4 alkyl, and halogen;
R7 is selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted heterocyclo, optionally substituted heteroalkyl, optionally substituted (cycloalkyl)alkyl, and optionally substituted (heterocyclo)alkyl; and
R8 is selected from the group consisting of hydrogen and halogen.