US 11,731,946 B2
Broad spectrum antivirulence, anti-persistence compounds
Laurence Rahme, Brookline, MA (US); Francois Lepine, Lavaltrie (CA); Damien Maura, Somerville, MA (US); Carmela Napolitano, Verona (IT); Antonio Felici, Vigasio (IT); Michele Negri, Zevio (IT); Stefano Fontana, Pove del Grappa (IT); and Daniele Andreotti, San Giovanni Lupatoto (IT)
Assigned to The General Hospital Corporation, Boston, MA (US); and Aptuit (Verona) SRL, An Evotec Company, Verona (IT)
Appl. No. 16/757,096
Filed by Francois Lepine, Lavaltrie (CA); The General Hospital Corporation, Boston, MA (US); and Aptuit (Verona) SRL, An Evotec Company, Verona (IT)
PCT Filed Oct. 19, 2018, PCT No. PCT/US2018/056771
§ 371(c)(1), (2) Date Apr. 17, 2020,
PCT Pub. No. WO2019/079759, PCT Pub. Date Apr. 25, 2019.
Claims priority of provisional application 62/663,105, filed on Apr. 26, 2018.
Claims priority of provisional application 62/574,500, filed on Oct. 19, 2017.
Prior Publication US 2021/0130306 A1, May 6, 2021
Int. Cl. C07D 263/58 (2006.01); C07C 237/42 (2006.01); C07C 255/60 (2006.01); C07C 327/42 (2006.01); C07D 209/08 (2006.01)
CPC C07D 263/58 (2013.01) [C07C 237/42 (2013.01); C07C 255/60 (2013.01); C07C 327/42 (2013.01); C07D 209/08 (2013.01)] 14 Claims
 
1. A compound selected from any one of the following compounds:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
Z1 is selected from the group consisting of O and S;
L1 is selected from the group consisting of methylene, methylmethylene, fluoromethylmethylene, fluoromethylene, difluoromethylene, and aminomethylene;
L2 is selected from the group consisting of NRN1C(O) and NRN1C(S);
RN1 and RN2 are each independently selected from the group consisting of H and C1-4 alkyl;
each R1 is independently selected from the group consisting of C1-4 haloalkyl, halo, CN, NO2, NH2, —COOH, —CONH2, and OH; and
each R2 is independently selected from the group consisting of halo, CN, NH2, —COOH, —CONH2, —C(O)C1-4 haloalkyl, —NHC(O)C1-4 haloalkyl, —NHSO2-C1-4 alkyl, and phenoxy;
wherein either R1 is CN or R2 is CN or phenoxy; and
wherein the compound of Formula I is not:

OG Complex Work Unit Chemistry