US 11,691,962 B2
Therapeutic compounds and compositions
Bertrand L. Chenard, Waterford, CT (US); Yuelian Xu, East Haven, CT (US); Frans L. Stassen, Cambridge, MA (US); Neil J. Hayward, Westborough, MA (US); and Zhiyao Teng, Newington, CT (US)
Assigned to EXITHERA PHARMACEUTICALS, INC., Westborough, MA (US)
Filed by eXIthera Pharmaceuticals, Inc., Westborough, MA (US)
Filed on Aug. 6, 2020, as Appl. No. 16/986,658.
Application 16/986,658 is a continuation of application No. PCT/US2019/016503, filed on Feb. 4, 2019.
Claims priority of provisional application 62/627,435, filed on Feb. 7, 2018.
Prior Publication US 2021/0188812 A1, Jun. 24, 2021
Int. Cl. C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 417/14 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 417/14 (2013.01)] 14 Claims
 
1. A compound of formula (II):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein
R1 is hydrogen or —NR8R9;
Ra is C1-6 alkyl, C1-6 haloalkyl, halo, cyano, or —OR6;
Rb is hydrogen or C1-6 alkyl;
R2 is optionally substituted 5-membered heteroaryl or optionally substituted 5-membered heterocyclyl;
R3 is hydrogen, C1-6 alkyl, or C1-6 haloalkyl;
R4 is C1-6 alkyl, C1-6 haloalkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein the cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with one, two, or three independent occurrences of halo, C1-6 alkyl, C1-6 haloalkyl, cyano, or —OR6;
R5 is hydrogen, C1-6 alkyl, C1-6 haloalkyl, cycloalkyl, or aryl, wherein the cycloalkyl or aryl is optionally substituted with one, two, or three independent occurrences of halo, C1-6 alkyl, C1-6 haloalkyl, cyano, or —OR6 or
R4 and R5, taken together with the carbon atom to which they are attached form a ring;
R6 is hydrogen, C1-6 alkyl, or C1-6 haloalkyl;
each R8 and R9 is independently hydrogen, C1-6 alkyl, —C(O)R10, or —C(O)OR10;
R10 is C1-6 alkyl or C1-6 haloalkyl;
Rx is —O or absent, wherein when Rx is —O, the nitrogen atom of the pyridyl ring is positively charged and Rx is negatively charged, thereby forming a pyridyl N-oxide;
m is 0, 1, 2, or, 3; and
n is 0 or 1, wherein if n is 0, then R5 is hydrogen and R4 is absent.