US 12,251,370 B2
Small molecule inhibitors of the BfrB:Bfd interaction
Mario Rivera, Baton Rouge, LA (US); Huili Yao, Baton Rouge, LA (US); Richard A. Bunce, Stillwater, OK (US); Baskar Nammalwar, San Diego, CA (US); Krishna Kumar Gnanasekaran, Mississauga (CA); Kate Eshelman, Alexandria, VA (US); Achala N. D. Punchi Hewage, Lawrence, KS (US); and Scott Lovell, Shawnee, KS (US)
Assigned to Board of Supervisors of Louisiana State University and Agricultural and Mechanical College, Baton Rouge, LA (US); University of Kansas, Lawrence, KS (US); and The Board of Regents for Oklahoma State University, Stillwater, OK (US)
Appl. No. 17/299,267
Filed by BOARD OF SUPERVISORS OF LOUISIANA STATE UNIVERSITY AND AGRICULTURAL AND MECHANICAL COLLEGE, Baton Rouge, LA (US); UNIVERSITY OF KANSAS, Lawrence, KS (US); and THE BOARD OF REGENTS FOR OKLAHOMA STATE UNIVERSITY, Stillwater, OK (US)
PCT Filed Dec. 3, 2019, PCT No. PCT/US2019/064272
§ 371(c)(1), (2) Date Jun. 2, 2021,
PCT Pub. No. WO2020/117832, PCT Pub. Date Jun. 11, 2020.
Claims priority of provisional application 62/831,616, filed on Apr. 9, 2019.
Claims priority of provisional application 62/775,304, filed on Dec. 4, 2018.
Prior Publication US 2022/0031661 A1, Feb. 3, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/4035 (2006.01); A61K 31/454 (2006.01); A61K 31/496 (2006.01); A61K 31/502 (2006.01); A61P 31/04 (2006.01); C07D 209/48 (2006.01); C07D 237/32 (2006.01); C07D 401/12 (2006.01); C07D 405/12 (2006.01)
CPC A61K 31/4035 (2013.01) [A61K 31/454 (2013.01); A61K 31/496 (2013.01); A61K 31/502 (2013.01); A61P 31/04 (2018.01); C07D 209/48 (2013.01); C07D 237/32 (2013.01); C07D 401/12 (2013.01); C07D 405/12 (2013.01)] 20 Claims
 
1. A compound according to Formula I

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt and/or a solvate thereof, wherein
R2 and R3 are each independently C1-C6 alkoxy, H, or OH, and R1 is C1-C6 alkoxy, H, OH, or halo, and at least one of R1, R2, and R3 is OH or C1-C6 alkoxy;
R4 and R5 are each independently H or halo;
X1 is CH2 or O; and
m is 0, 2, 3, 4, or 5;
provided that when X1 is O, m is not 0; and
provided that when R2 is OH, R1, R3, R4, and R5 are each H, X1 is CH2, and m is not 0.