US 12,234,202 B2
Covalent inhibitors of coronavirus papain-like protease
Brian Sanders, Knoxville, TN (US); Stephanie S. Galanie, Scotch Plains, NJ (US); and Jerry M. Parks, Knoxville, TN (US)
Assigned to UT-Battelle, LLC, Oak Ridge, TN (US)
Filed by UT-Battelle, LLC, Oak Ridge, TN (US)
Filed on Aug. 26, 2022, as Appl. No. 17/896,182.
Claims priority of provisional application 63/237,578, filed on Aug. 27, 2021.
Prior Publication US 2023/0102656 A1, Mar. 30, 2023
Int. Cl. C07C 243/28 (2006.01); A61P 31/14 (2006.01); C07C 255/03 (2006.01)
CPC C07C 243/28 (2013.01) [A61P 31/14 (2018.01); C07C 255/03 (2013.01)] 26 Claims
 
1. A compound having the following structure:

OG Complex Work Unit Chemistry
wherein:
R1 is a linker having the formula —(CH2)n-L1-, wherein L1 contains 1-6 carbon atoms and at least one —NH— linkage and at least one oxygen-containing or sulfur-containing linkage, and n is an integer of 0-3;
R2 is a group having the formula —C(Y)-E, wherein Y is O or S, and E is a hydrocarbon group containing 1-12 carbon atoms and either: (i) at least one carbon-carbon or carbon-nitrogen unsaturated bond or (ii) at least one alkyl halide group;
R3 is selected from the group consisting of H, NR′2, NHC(O)R′, and —(CH2)p-T, wherein T contains at least one —NH— linkage; R′ is independently selected from H and hydrocarbon groups containing 1-6 carbon atoms; and p is an integer of 0-3;
Ra, Rb, Rc, Rd, Re, and Rf are independently selected from the group consisting of H, hydrocarbon groups containing 1-3 carbon atoms, fluorine atom, and chlorine atom;
X is N or CR9, wherein R9 is selected from the group consisting of H, hydrocarbon groups containing 1-3 carbon atoms, fluorine atom, and chlorine atom;
and pharmaceutically acceptable salts thereof.