Granted Patent B2

US 12,723,057 · App. 18/174,474 · Granted Sep 1, 2026

Inventors: Byoung-Kwon Chun (Pleasanton, CA); Michael O. Clarke (Redwood City, CA); Deeba Ensan (Foster City, CA); Richard L. Mackman (Millbrae, CA); Devan Naduthambi (San Bruno, CA); Dustin S. Siegel (Half Moon Bay, CA)

Assignee: Gilead Sciences, Inc.

C07H7/06A61K31/706A61P31/14

Abstract

Claims (34)

1 . A compound of Formula I:

or a pharmaceutically acceptable salt thereof, wherein:

R 1 is OH;

R 2 is OH;

R 3 is C(O)R 7 ;

R 7 is C 1 -C 8 alkyl, C 3 -C 8 carbocyclyl, C 6 -C 10 aryl, 4 to 6 membered heterocyclyl containing 1, 2, or 3 O, or 5 to 6 membered heteroaryl containing 1, 2, or 3 heteroatoms selected from N, O, and S;

wherein the alkyl, carbocyclyl, aryl, heterocyclyl, and heteroaryl of R 7 are each, independently, optionally substituted with one, two or three substituents independently selected from the group consisting of halo, oxo, cyano, —N 3 , —OR 8 , C 1 -C 8 alkyl, —NR 9 R 10 , C 3 -C 8 carbocyclyl optionally substituted with C 1 -C 6 alkyl, and phenyl optionally substituted with one, two, or three substituents independently selected from halo, cyano, and C 1 -C 6 alkyl; and

each R 8 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, and C 3 -C 6 cycloalkyl;

each R 9 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, and C 3 -C 6 cycloalkyl;

each R 10 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, and C 3 -C 6 cycloalkyl; and

Base is

 wherein

R 11 is C 1 -C 6 alkyl substituted with —OP(O)(OH) 2 or —OC(O)R 12 ;

R 12 is C 1 -C 8 alkyl; and

R 13 is C 1 -C 6 alkyl substituted with —OP(O)(OH) 2 or —OC(O)R 12 .

2 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein R 3 is

3 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein R 7 is C 1 -C 8 alkyl.

4 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein R 7 is C 1 -C 6 alkyl.

5 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein R 7 is C 3 -C 8 carbocyclyl.

6 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein Base is

7 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein Base is

8 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein the compound is

9 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein the compound is

10 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein the compound is

11 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein the compound is

12 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein the compound is

13 . The compound of claim 1 , or the pharmaceutically acceptable salt thereof, wherein the compound is

14 . A pharmaceutical composition comprising a pharmaceutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or excipient.

15 . A method of treating a viral infection in a human in need thereof, wherein the method comprises administering to the human a therapeutically effective amount of a pharmaceutical composition of claim 14 .

16 . The method of claim 15 , wherein the viral infection is a pneumoviridae virus infection.

17 . The method of claim 16 , wherein the pneumoviridae virus infection is respiratory syncytial virus infection.

18 . The method of claim 16 , wherein the pneumoviridae virus infection is human metapneumovirus infection.

19 . The method of claim 15 , wherein the viral infection is a picornaviridae virus infection.

20 . The method of claim 19 , wherein the picornaviridae virus infection is human rhinovirus infection.

Assignments (1)

Continuity (2)

References Cited (400)