US 11,912,714 B2
Spiropyrrolidine derived antiviral agents
Hui Cao, Belmont, MA (US); Wei Li, Lexington, MA (US); Xuri Gao, Newtonville, MA (US); Jiajun Zhang, Cambridge, MA (US); Xiaowen Peng, Sudbury, MA (US); Jorden Kass, Arlington, MA (US); Ruichao Shen, Belmont, MA (US); Guoqiang Wang, Belmont, 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 Nov. 9, 2022, as Appl. No. 17/983,501.
Claims priority of provisional application 63/278,917, filed on Nov. 12, 2021.
Prior Publication US 2023/0151019 A1, May 18, 2023
Int. Cl. C07D 487/10 (2006.01); A61P 31/14 (2006.01)
CPC C07D 487/10 (2013.01) [A61P 31/14 (2018.01)] 13 Claims
 
1. A compound represented by Formula (I), or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein:
A is selected from:
1) —R11;
2) —OR12; and
3) —NR13R14;
-L1- is

OG Complex Work Unit Chemistry
-L2- is

OG Complex Work Unit Chemistry
B is an optionally substituted aryl or optionally substituted heteroaryl;
X is selected from:
1) —CN;
2) —C(O)R15;
3) —CH(OH)SO3R16;
4) —C(O)NR13R14;
5) —C(O)C(O)NR13R14; and
6) —C≡C—R17;
R1, R2, R3, R5, R6, and R17 are each independently selected from:
1) Hydrogen;
2) Optionally substituted —C1-C8 alkyl;
3) Optionally substituted —C2-C8 alkenyl;
4) Optionally substituted —C2-C8 alkynyl;
5) Optionally substituted —C3-C8 cycloalkyl;
6) Optionally substituted 3- to 8-membered heterocycloalkyl;
7) Optionally substituted aryl;
8) Optionally substituted arylalkyl;
9) Optionally substituted heteroaryl; and
10) Optionally substituted heteroarylalkyl;
alternatively, R1 and R2 are taken together with the carbon atom to which they are attached to form an optionally substituted 3- to 8-membered carbocyclic ring or an optionally substituted 3-to 8-membered heterocyclic ring;
alternatively, R2 and R3 are taken together with the carbon atom and nitrogen atom to which they are corresponding attached to form an optionally substituted 4- to 8-membered heterocyclic ring;
alternatively, R5 and R6 are taken together with the carbon atom to which they are attached to form an optionally substituted 3- to 8-membered carbocyclic ring or an optionally substituted 3-to 8-membered heterocyclic ring;
R4 is hydrogen, optionally substituted —C1-C4 alkyl, optionally substituted C2-C4-alkenyl, or optionally substituted —C3-C6 cycloalkyl;
R11 is selected from:
1) Optionally substituted —C1-C8 alkyl;
2) Optionally substituted —C2-C8 alkenyl;
3) Optionally substituted —C2-C8 alkynyl;
4) Optionally substituted —C3-C8 cycloalkyl;
5) Optionally substituted 3- to 8-membered heterocycloalkyl;
6) Optionally substituted aryl;
7) Optionally substituted arylalkyl;
8) Optionally substituted heteroaryl; and
9) Optionally substituted heteroarylalkyl;
R12, R13, and R14 each independently selected from:
1) Hydrogen;
2) Optionally substituted —C1-C8 alkyl;
3) Optionally substituted —C2-C8 alkenyl;
4) Optionally substituted —C2-C8 alkynyl;
5) Optionally substituted —C3-C8 cycloalkyl;
6) Optionally substituted 3- to 8-membered heterocycloalkyl;
7) Optionally substituted aryl;
8) Optionally substituted arylalkyl;
9) Optionally substituted heteroaryl; and
10) Optionally substituted heteroarylalkyl;
alternatively, R13 and R14 are taken together with the nitrogen atom to which they are attached to form an optionally substituted 3- to 8-membered heterocyclic ring;
R15 is hydrogen, hydroxy, optionally substituted —C1-C8 alkyl, or optionally substituted heteroary; and R16 is hydrogen or Na+.