US 11,938,114 B2
Bacterial efflux pump inhibitors
Edmond J. LaVoie, New Brunswick, NJ (US); Ajit Parhi, New Brunswick, NJ (US); and Yongzheng Zhang, Monmouth Junction, NJ (US)
Assigned to RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY, New Brunswick, NJ (US)
Appl. No. 16/492,908
Filed by RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY, New Brunswick, NJ (US)
PCT Filed Mar. 9, 2018, PCT No. PCT/US2018/021851
§ 371(c)(1), (2) Date Sep. 10, 2019,
PCT Pub. No. WO2018/165614, PCT Pub. Date Sep. 13, 2018.
Claims priority of provisional application 62/470,038, filed on Mar. 10, 2017.
Prior Publication US 2021/0137881 A1, May 13, 2021
Int. Cl. C07D 207/09 (2006.01); A61K 9/00 (2006.01); A61K 9/08 (2006.01); A61K 9/20 (2006.01); A61K 9/28 (2006.01); A61K 9/48 (2006.01); A61K 31/40 (2006.01); A61K 45/06 (2006.01); A61K 47/02 (2006.01); A61P 31/04 (2006.01); C07D 207/12 (2006.01); C07D 207/14 (2006.01)
CPC A61K 31/40 (2013.01) [A61K 9/0019 (2013.01); A61K 9/08 (2013.01); A61K 9/2013 (2013.01); A61K 9/2018 (2013.01); A61K 9/2027 (2013.01); A61K 9/2054 (2013.01); A61K 9/2059 (2013.01); A61K 9/28 (2013.01); A61K 9/485 (2013.01); A61K 9/4858 (2013.01); A61K 9/4866 (2013.01); A61K 45/06 (2013.01); A61K 47/02 (2013.01); A61P 31/04 (2018.01); C07D 207/09 (2013.01); C07D 207/12 (2013.01); C07D 207/14 (2013.01)] 9 Claims
 
1. A compound of formula I:

OG Complex Work Unit Chemistry
wherein:
A is —C(═O)N(Ra1)—R1;
R1 is pyrrolidinyl-(C1-C4)alkyl-, wherein pyrrolidinyl-(C1-C4)alkyl- is substituted with one or more groups independently selected from the group consisting of Z and —(C1-C6)alkyl substituted with one or more Z, and wherein the pyrrolidinyl-(C1-C4)alkyl- is further optionally substituted with one or more (C1-C4)alkyl;
each Z is NRb2Rc2;
R2 is hydrogen;
R3 is aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, —NO2, —CN, (C1-C6)alkyl, (C1-C4)haloalkyl, (C1-C6)alkoxy, and (C1-C4)haloalkoxy;
R4 is hydrogen;
R5 is aryl wherein the aryl is optionally substituted with one or more groups independently selected from halo, —NO2, —CN, (C1-C6)alkyl, (C1-C4)haloalkyl, (C1-C6)alkoxy, and (C1-C4)haloalkoxy;
R6 is hydrogen;
Ra1 is hydrogen; and
each Rb2 and Rc2 is independently hydrogen, (C1-C6)alkyl or (C3-C7)carbocyclyl;
or a salt thereof.