US 11,919,910 B2
Spiropyrrolidine derived antiviral agents
Guoqiang Wang, Belmont, MA (US); Ruichao Shen, Belmont, MA (US); Xuechao Xing, Wilmington, MA (US); Yong He, Lexington, MA (US); Matthew C. Rhodes, Boston, 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. 17/983,474.
Claims priority of provisional application 63/278,553, filed on Nov. 12, 2021.
Prior Publication US 2023/0203048 A1, Jun. 29, 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):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
B is an optionally substituted aryl or optionally substituted heteroaryl;
X is an optionally substituted aryl or optionally substituted heteroaryl;
R1, R2, and R3 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, R1 and R3 are taken together with the carbon atom and the nitrogen atom to which they are attached corresponding to form an optionally substituted 4- to 8-membered heterocyclic ring;
R4 is hydrogen, optionally substituted —C1-C4 alkyl, optionally substituted —C2-C4-alkenyl, or optionally substituted —C3-C6 cycloalkyl;
A is selected from:
1) —R11;
2) —OR12;
3) —NR13R14;
4) —C(R21R22)NR13C(O)R11;
5) —C(R21R22)NR13C(O)OR12;
6) —C(R21R22)NR23C(O)NR13R14;
7) —C(R21R22)NR13SO2R11;
8) —C(R21R22)NR13R14;
9) —C(O)R11; and
10) —C(O)NR13R14;
R11 and R12 are each independently 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;
R13, R14, R21, R22, and R23 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, 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.