US 12,030,903 B2
Antiviral compounds
Daniel H. Byun, Foster City, CA (US); Gregory F. Chin, San Francisco, CA (US); Michael O. Clarke, Redwood City, CA (US); Bindu Goyal, Fremont, CA (US); Petr Jansa, Foster City, CA (US); Richard L. Mackman, Millbrae, CA (US); Michael R. Mish, Foster City, CA (US); and Dustin S. Siegel, Half Moon Bay, CA (US)
Assigned to Gilead Sciences, Inc., Foster City, CA (US)
Filed by Gilead Sciences, Inc., Foster City, CA (US)
Filed on Feb. 17, 2021, as Appl. No. 17/178,115.
Claims priority of provisional application 62/978,199, filed on Feb. 18, 2020.
Prior Publication US 2021/0292348 A1, Sep. 23, 2021
Int. Cl. C07F 9/6561 (2006.01); A61K 45/06 (2006.01)
CPC C07F 9/6561 (2013.01) [A61K 45/06 (2013.01)] 33 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
Base is

OG Complex Work Unit Chemistry
R1 and R2 are each independently H or —C(O)R1A, wherein R1A is C1-6 alkyl;
R3 is —N(H)R3A;
R3A is H, —CH2OP(O)(OH)2, or —C(O)R3D, wherein
R3D is C6-12 aryl or C1-6 alkyl optionally substituted with a C3-6 cycloalkyl;
R4A is O;
R4B and R4C are each independently:
(A) —OH;
(B) —OR4B1, wherein R4B1 is C6-12 aryl;
(C)

OG Complex Work Unit Chemistry
 wherein
subscript m is 0, 1, 2, 3, 4, or 5; and
each R4D is independently C1-6 alkyl;
(D)

OG Complex Work Unit Chemistry
 wherein
R4E1 and R4E2 are each independently H or C1-6 alkyl;
R4F1 and R4F2 together are oxo;
R4G is C1-8 alkyl optionally substituted with 1 to 3 R4G1, C3-8 cycloalkyl, or a 3 to 8 membered heterocyclyl having 1 to 3 heteroatoms selected from N, O and S, optionally substituted with 1 to 3 R4G3;
each R4G1 is independently —OH, C1-6 alkoxy, —(CH2OCH2)1-5—CH3, C1-3 haloalkyl, or C3-8 cycloalkyl optionally substituted with 1 to 3 R4G9;
each R4G3 and R4G9 is independently C1-6 alkyl; or
(E) —(OP(O)(OH))1-2—OH; and
R5A is C1-6 alkyl substituted with —OP(O)(OH)2.