US 12,006,326 B2
Antiviral heterocyclic compounds
Adam Szymaniak, Boston, MA (US); Kevin McGrath, Brighton, MA (US); Jianming Yu, Plainsboro, NJ (US); Tyler Mann, Brighton, MA (US); Long Nguyen, Boston, MA (US); Kaicheng Zhu, Belmont, MA (US); In Jong Kim, 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 Aug. 24, 2022, as Appl. No. 17/894,412.
Application 17/894,412 is a continuation of application No. 17/220,300, filed on Apr. 1, 2021, granted, now 11,505,558.
Application 17/220,300 is a continuation in part of application No. 16/930,622, filed on Jul. 16, 2020, granted, now 11,572,367.
Claims priority of provisional application 62/910,712, filed on Oct. 4, 2019.
Claims priority of provisional application 62/959,230, filed on Jan. 10, 2020.
Claims priority of provisional application 63/038,234, filed on Jun. 12, 2020.
Prior Publication US 2023/0125803 A1, Apr. 27, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 491/052 (2006.01); C07D 471/04 (2006.01); C07D 491/044 (2006.01); C07D 491/048 (2006.01)
CPC C07D 491/052 (2013.01) [C07D 471/04 (2013.01); C07D 491/044 (2013.01); C07D 491/048 (2013.01)] 18 Claims
 
1. A compound represented by Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
A is selected from the group consisting of:
1) optionally substituted aryl; and
2) optionally substituted heteroaryl;
B is O;
R1 and R2 are each hydrogen;
Z is hydrogen;
W is
optionally substituted —C1-C6 alkyl;
G is
—C(O)NR11R12;
n is 1;
Y is O;
E is optionally substituted aryl;
R3 is hydroxy or fluorine;
R4 is selected from the group consisting of
optionally substituted —C1-C6 alkyl and
optionally substituted —C3-C8 cycloalkyl;
R11 at each occurrence is independently selected from the group consisting of:
1) hydrogen;
2) optionally substituted —C1-C8-alkyl;
3) optionally substituted —C3-C8-cycloalkyl;
4) optionally substituted 3- to 8-membered heterocyclic;
5) optionally substituted aryl;
6) optionally substituted arylalkyl;
7) optionally substituted heteroaryl; and
8) optionally substituted heteroarylalkyl; and
R12 at each occurrence is independently selected from the group consisting of:
1) hydrogen;
2) optionally substituted —C1-C8-alkyl;
3) optionally substituted —C3-C8-cycloalkyl;
4) optionally substituted 3- to 8-membered heterocyclic;
5) optionally substituted aryl;
6) optionally substituted arylalkyl;
7) optionally substituted heteroaryl; and
8) optionally substituted heteroarylalkyl;
alternatively, R11 and R12 are taken together with the nitrogen atom to which they are attached to form a 3- to 12-membered heterocyclic ring.