US 12,268,723 B2
Peptidomimetics for the treatment of coronavirus and picorna virus infections
Raymond F. Schinazi, Atlanta, GA (US); Keivan Zandi, Atlanta, GA (US); and Franck Amblard, Atlanta, GA (US)
Assigned to Emory University, Atlanta, GA (US)
Filed by Emory University, Atlanta, GA (US)
Filed on Dec. 7, 2021, as Appl. No. 17/544,438.
Application 17/544,438 is a division of application No. 16/894,407, filed on Jun. 5, 2020, granted, now 11,207,370.
Claims priority of provisional application 62/857,674, filed on Jun. 5, 2019.
Prior Publication US 2022/0273753 A1, Sep. 1, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 38/06 (2006.01); A61K 31/519 (2006.01); A61K 31/53 (2006.01); A61K 31/675 (2006.01); A61K 31/7072 (2006.01); A61K 38/05 (2006.01); A61K 45/06 (2006.01); C07K 5/065 (2006.01); C07K 5/08 (2006.01); C07K 5/087 (2006.01); C07K 5/093 (2006.01); A61P 31/14 (2006.01)
CPC A61K 38/06 (2013.01) [A61K 31/519 (2013.01); A61K 31/53 (2013.01); A61K 31/675 (2013.01); A61K 31/7072 (2013.01); A61K 38/05 (2013.01); A61K 45/06 (2013.01); C07K 5/06078 (2013.01); C07K 5/0812 (2013.01); C07K 5/0819 (2013.01); C07K 5/0827 (2013.01); A61P 31/14 (2018.01)] 4 Claims
 
1. A compound of Formulas III or V:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein:
R1 is optionally substituted aryl, 5-membered ring heteroaryl, aryloxy, heteroaryloxy, or heteroarylalkoxy,
R3 is an optionally substituted arylalkyl, alkylaryl, heteroarylalkyl, or alkylheteroaryl, —CH2-(hydroxy) phenyl, and —CH2-(halo) phenyl,
R4 is an optionally substituted C1-6 alkyl,
R5 is CH═C(CN)C(O)NH2, —C(O)CF3, —CH(OH)CF3, —C(OH)SO3− (and an associated cation), or an optionally-substituted epoxide ring,
R2, R2′, R10 and R10′ are, independently, hydrogen, CF3, C1-6 alkyl, C1-6 haloalkyl, or C2-6 alkenyl,
X is, independently, a bond or NH,
n and p are, independently, 0, 1, 2, or 3;
m is 2,
p is 0;
R6 and R6′ are, independently, hydrogen, halogen, CF3, hydroxy, N(R′)S(O)2R′, S(O)2R′, S(O)2N(R′)2, C1-6 alkoxy, C2-6 alkenyl, cyano, C2-6 alkynyl, C3-6 alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, C1-6 alkyl, arylalkoxycarbonyl, carboxy, C1-6 haloalkyl, heterocyclylalkyl, or C1-6 hydroxyalkyl; or R6 and R6′, together with the carbon to which they are attached, form a carbonyl,
each R′ is, independently, H, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, aryl, heteroaryl, alkylaryl, or arylalkyl,
the R′ groups can optionally be substituted with one or more substituents, which substituents are, independently, halo, C1-6 haloalkyl, C1-6 hydroxyalkyl, hydroxyl, carboxyl, acyl, aryl, acyloxy, amino, amido, carboxyl derivatives, alkylamino, dialkylamino, arylamino, alkoxy, alkoxyalkyl, aryloxy, nitro, cyano, sulfonic acid, thiol, imine, sulfonyl, sulfanyl, sulfinyl, sulfamonyl, ester, carboxylic acid, amide, phosphonyl, phosphinyl, phosphoryl, phosphine, thioester, thioether, acid halide, anhydride, oxime, hydrozine, carbamate, phosphonic acid, or phosphonate;
two R′ residing on the same carbon or nitrogen atom can come together to form a C3-6 ring optionally containing a N, O, or S heteroatom;
R6 and R6′ can come together to form an optionally substituted double bond or a C3-6 ring optionally containing a N, O, or S heteroatom;
R7 and R7′ are, independently, hydrogen, CF3, N(R′) S(O)2R′, S(O)2R′, S(O)2N(R′)2, C1-6 alkoxy, C2-6 alkenyl, cyano, C2-6 alkynyl, C3-6 alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, C1-6 alkyl, arylalkoxycarbonyl, carboxy, C1-6 haloalkyl, heterocyclylalkyl, or C1-6 hydroxyalkyl; and
R7 and R7′ can come together to form an optionally substituted double bond or a C3-6 ring optionally containing a N, O, or S heteroatom;
wherein, with respect to Formula V, m is 1.