US 11,850,247 B2
Antiviral compounds
Zhengqiang Wang, Minneapolis, MN (US); and Stefanos G. Sarafianos, Atlanta, GA (US)
Assigned to REGENTS OF THE UNIVERSITY OF MINNESOTA, Minneapolis, MN (US); and EMORY UNIVERSITY, Atlanta, GA (US)
Filed by REGENTS OF THE UNIVERSITY OF MINNESOTA, Minneapolis, MN (US); and Emory University, Atlanta, GA (US)
Filed on Apr. 5, 2021, as Appl. No. 17/222,433.
Claims priority of provisional application 63/008,320, filed on Apr. 10, 2020.
Prior Publication US 2021/0322416 A1, Oct. 21, 2021
Int. Cl. C07D 403/12 (2006.01); C07D 401/12 (2006.01); C07D 239/96 (2006.01); C07D 239/54 (2006.01); A61K 31/513 (2006.01); A61K 31/495 (2006.01); A61K 31/4439 (2006.01); A61K 31/4184 (2006.01); A61K 31/4178 (2006.01); A61K 31/51 (2006.01); C07D 209/34 (2006.01); C07D 235/02 (2006.01); C07D 241/08 (2006.01); A61P 31/18 (2006.01); A61K 31/517 (2006.01); A61K 31/405 (2006.01); C07C 233/88 (2006.01); A61K 31/167 (2006.01); A61K 45/06 (2006.01)
CPC A61K 31/517 (2013.01) [A61K 31/167 (2013.01); A61K 31/405 (2013.01); A61K 31/4178 (2013.01); A61K 31/4184 (2013.01); A61K 31/4439 (2013.01); A61K 31/495 (2013.01); A61K 31/513 (2013.01); A61K 45/06 (2013.01); A61P 31/18 (2018.01); C07C 233/88 (2013.01); C07D 209/34 (2013.01); C07D 235/02 (2013.01); C07D 239/54 (2013.01); C07D 239/96 (2013.01); C07D 241/08 (2013.01); C07D 401/12 (2013.01); C07D 403/12 (2013.01)] 20 Claims
 
1. A compound of formula I, formula II, or formula III:

OG Complex Work Unit Chemistry
or a salt thereof, wherein:
R1 is selected from the group consisting of:

OG Complex Work Unit Chemistry
R2 is methyl or ethyl;
R3 is phenyl, optionally substituted at the 3-position with bromo, chloro, fluoro, methyl, or methoxy, and optionally substituted at the 4-position with bromo, chloro, fluoro, methyl, or methoxy;
R4 is 4-chloropyridyl, 4-bromopyridyl, or phenyl that is optionally substituted at the 4-position with halo, methyl, ethyl, or methoxy;
R5 is selected from the group consisting of:

OG Complex Work Unit Chemistry
R6 is a ring:

OG Complex Work Unit Chemistry
which ring is optionally substituted with carboxy, (C1-C6)alkoxycarbonyl, or —C(═O)NRcRd;
R7 is 4-chloropyridyl, 4-bromopyridyl, or phenyl that is optionally substituted at the 4-position with halo, methyl, ethyl, or methoxy;
R8 is selected from the group consisting of:

OG Complex Work Unit Chemistry
R9 is pyridyl that is substituted with phenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, or 4-cyanophenyl or R9 is imidazole that is substituted with phenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, or 4-cyanophenyl;
R10 is 4-chloropyridyl, 4-bromopyridyl, or phenyl that is optionally substituted at the 4-position with halo, methyl, ethyl, or methoxy;
Ra is H or methyl;
Rb is phenyl that is optionally substituted with one or more groups independently selected from the group consisting of nitro, halo, (C1-C6)alkyl, halo(C1-C6)alkyl, hydroxy, —SO2F, and NReRf;
Rc is H, phenyl, benzyl, or (C1-C6)alkyl;
Rd is H, phenyl, benzyl, or (C1-C6)alkyl;
Re is H, hydroxy, or (C1-C6)alkyl;
Rf is H or (C1-C6)alkyl;
Rg is H, OH, or (C1-C6)alkoxy; and
Rh is H or (C1-C6)alkyl.