US 12,173,029 B2
Antiviral prodrugs, pharmaceutical formulations, and methods
Karl Y. Hostetler, La Jolla, CA (US); James Beadle, La Jolla, CA (US); Nadejda Valiaeva, La Jolla, CA (US); and Robert T. Schooley, La Jolla, CA (US)
Assigned to THE REGENTS OF THE UNIVERSITY OF CALIFORNIA, Oakland, CA (US)
Appl. No. 18/006,330
Filed by THE REGENTS OF THE UNIVERSITY OF CALIFORNIA, Oakland, CA (US)
PCT Filed Jul. 24, 2021, PCT No. PCT/US2021/043094
§ 371(c)(1), (2) Date Jan. 20, 2023,
PCT Pub. No. WO2022/020793, PCT Pub. Date Jan. 27, 2022.
Claims priority of provisional application 63/145,698, filed on Feb. 4, 2021.
Claims priority of provisional application 63/110,596, filed on Nov. 6, 2020.
Claims priority of provisional application 63/078,427, filed on Sep. 15, 2020.
Claims priority of provisional application 63/070,695, filed on Aug. 26, 2020.
Claims priority of provisional application 63/055,944, filed on Jul. 24, 2020.
Prior Publication US 2023/0287029 A1, Sep. 14, 2023
Int. Cl. C07H 7/06 (2006.01); A61P 31/14 (2006.01); C07H 9/02 (2006.01)
CPC C07H 7/06 (2013.01) [A61P 31/14 (2018.01); C07H 9/02 (2013.01)] 39 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
wherein—
Nuc is selected from the group consisting of beta-D-N4-hydroxycytidine (NHC), (2′R)-2-amino-2′-deoxy-2′-fluoro-N,2′-dimethyladenosine, and GS-441524:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
Y is independently selected from the group consisting of hydrogen, a C1-C30 hydrocarbyl, a pharmaceutically acceptable cation, and a covalent bond to a carbon atom of a five-carbon sugar moiety of the antiviral nucleoside or the antiviral nucleoside analog;
x is 0 or 1;
L is a C1-C6 hydrocarbyl; and
R is independently selected from the group consisting of a C10-C30 hydrocarbyl and a substituent of formula (A);

OG Complex Work Unit Chemistry
wherein R1 and R2 are independently selected from the group consisting of hydrogen and a C1-C30 hydrocarbyl.