US 10,428,070 B2
Hepatitis B antiviral agents
Yao-Ling Qiu, Andover, MA (US); Xuri Gao, Newtonville, MA (US); Xiaowen Peng, Sudbury, MA (US); Wei Li, Lexington, MA (US); Jorden Kass, Arlington, MA (US); Hui Cao, Belmont, MA (US); Byung-Chul Suh, Lexington, MA (US); and Yat Sun Or, Waltham, MA (US)
Assigned to Enanta Pharmaceuticals, Inc., Watertown, MA (US)
Filed by Enanta Pharmaceuticals, Inc., Watertown, MA (US)
Filed on Dec. 5, 2018, as Appl. No. 16/210,472.
Claims priority of provisional application 62/595,271, filed on Dec. 6, 2017.
Claims priority of provisional application 62/674,209, filed on May 21, 2018.
Prior Publication US 2019/0177320 A1, Jun. 13, 2019
Int. Cl. A61K 45/06 (2006.01); C07D 471/10 (2006.01); A61P 31/14 (2006.01); C07D 471/20 (2006.01); C07D 471/04 (2006.01)
CPC C07D 471/10 (2013.01) [A61P 31/14 (2018.01); C07D 471/04 (2013.01); C07D 471/20 (2013.01); A61K 45/06 (2013.01)] 17 Claims
 
1. A compound represented by Formula (I):

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof, wherein:
A is optionally substituted aryl or optionally substituted heteroaryl;
B is selected from the group consisting of hydrogen, halo, CN, optionally substituted —C1-C6 alkyl, and optionally substituted C3-C6 cycloalkyl;
X is optionally substituted aryl or optionally substituted heteroaryl;
Y is —C(O)NR1R2, —C(O)OR1, optionally substituted aryl or optionally substituted heteroaryl;
R1 and R2 are each independently selected from the group consisting of hydrogen, optionally substituted —C1-C6 alkyl, optionally substituted —C2-C8 alkenyl, optionally substituted —C2-C8 alkynyl, optionally substituted —C3-C8 cycloalkyl, optionally substituted 3- to 8-membered heterocyclic, optionally substituted aryl, and optionally substituted heteroaryl; alternatively, R1 and R2 are taken together with the nitrogen atom to which they are attached to form an optionally substituted 3- to 8-membered heterocyclic; and
R and Z are taken together with the carbon atom to which they are attached to form an optionally substituted 3- to 8-membered cycloalkyl, 3- to 8-membered cycloalkenyl, or 3- to 8-membered heterocyclic;
provided that when Y is optionally substituted aryl or optionally substituted heteroaryl, R and Z taken together with carbon atom to which they are attached do not form

OG Complex Work Unit Drawing
where R5 is hydrogen, optionally substituted —C1-C8 alkyl, optionally substituted —C2-C8 alkenyl, optionally substituted —C2-C8 alkynyl, optionally substituted —C3-C8 cycloalkyl, optionally substituted 3- to 8-membered heterocyclic, optionally substituted aryl, optionally substituted heteroaryl, —C(O)R13, —C(O)OR13, —C(O)NR13R14, —S(O)2R13, or —S(O)2NR13R14; and R13 and R14 at each occurrence are independently hydrogen, optionally substituted —C1-C8 alkyl, optionally substituted —C2-C8 alkenyl, optionally substituted —C2-C8 alkynyl, optionally substituted —C3-C8 cycloalkyl, optionally substituted 3- to 8-membered heterocyclic, optionally substituted aryl or optionally substituted heteroaryl.