US 11,987,554 B2
Protease inhibitors as antivirals
Long Mao, San Diego, CA (US); Xiao Xu, San Diego, CA (US); Namir Shaabani, San Diego, CA (US); and Can Jin, San Diego, CA (US)
Assigned to Vivasor, Inc., San Diego, CA (US)
Filed by ACEA Therapeutics, Inc., San Diego, CA (US)
Filed on Jun. 15, 2023, as Appl. No. 18/210,555.
Application 18/210,555 is a division of application No. 17/830,185, filed on Jun. 1, 2022, granted, now 11,753,373.
Claims priority of provisional application 63/275,113, filed on Nov. 3, 2021.
Claims priority of provisional application 63/195,930, filed on Jun. 2, 2021.
Prior Publication US 2023/0322668 A1, Oct. 12, 2023
Int. Cl. C07D 207/26 (2006.01); C07D 207/416 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 403/12 (2006.01); C07D 403/14 (2006.01); C07D 413/14 (2006.01)
CPC C07D 207/26 (2013.01) [C07D 207/416 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 403/12 (2013.01); C07D 403/14 (2013.01); C07D 413/14 (2013.01)] 16 Claims
 
1. A method to treat a viral infection, which comprises administering to a subject in need of such treatment a compound of Formula (I):

OG Complex Work Unit Chemistry
or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, a tautomer, a mixture of two or more tautomers, or an isotopic variant thereof; or a pharmaceutically acceptable salt, solvate, or hydrate thereof; wherein:
Z is selected from —CH2CN, —C(═O)—CH═CH2, and —CH(OH)SO3− (and an associated cation, optionally wherein the cation is Na+);
L is —C(═O)—NH—;
R1 is

OG Complex Work Unit Chemistry
R2 is selected from C1-6 alkyl, 3-7 membered cycloalkyl, C1-3 alkyl-(3-7 membered cycloalkyl), and (3-7 membered cycloalkyl)-C1-3 alkyl, each of which is optionally substituted with up to three groups selected from halo, CN, C1-3 alkyl, C1-6 alkoxy, C1-3 haloalkyl, and C1-3 haloalkoxy;
R3 is H or C1-4 alkyl;
each R* is independently selected from C1-3 alkyl, C1-3 alkoxy, C1-3 haloalkyl, CN, halo, and —OH;
m is an integer from 0 to 2; and
n is an integer from 0 to 4 wherein the viral infection is a coronavirus infection.