US 11,970,481 B1
Substituted pyridine derivatives as SARM1 inhibitors
Jennifer Aiden Kozak, Pacifica, CA (US); Sean Pomeroy Brown, Half Moon Bay, CA (US); Christopher Michael Tegley, San Carlos, CA (US); Alexander Wayne Schammel, San Francisco, CA (US); Liusheng Zhu, Foster City, CA (US); Maximiliano De La Higuera Macias, San Francisco, CA (US); and Shilpa Sambashivan, Los Altos, CA (US)
Assigned to NURA BIO, INC., South San Francisco, CA (US)
Filed by Nura Bio, Inc., South San Francisco, CA (US)
Filed on Oct. 4, 2023, as Appl. No. 18/481,173.
Application 18/481,173 is a continuation of application No. 18/019,452, previously published as PCT/US2021/044389, filed on Aug. 3, 2021.
Claims priority of provisional application 63/060,790, filed on Aug. 4, 2020.
Int. Cl. C07D 403/14 (2006.01); A61P 25/28 (2006.01); C07D 403/04 (2006.01)
CPC C07D 403/14 (2013.01) [A61P 25/28 (2018.01); C07D 403/04 (2013.01)] 18 Claims
 
1. A compound of Formula Ic:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
A is N or N+—O—;
Q1 and Q2 are each independently selected from CH and N;
W is O, S, or NRN;
--- is a single bond;
X is CR5R6 and Y is CR8R9;
Ring Z is C6-10 aryl, C3-7 cycloalkyl, 5-10 membered heteroaryl, or 4-10 membered heterocycloalkyl;
RN is H, C1-4 alkyl, or CN;
R1 is halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, or C1-4 haloalkoxy;
R2C is selected from H, C1-4 alkyl, C1-4 hydroxyalkyl, C1-4cyanoalkyl, and C3-7 cycloalkyl;
R3 and R5, together with the atoms to which they are attached and together with any intervening atoms, form a 5-7 membered heterocycloalkyl ring optionally substituted by 1, 2, or 3 substituents independently selected from oxo, halo, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, and C1-4 haloalkoxy;
each R4 is independently halo, nitro, cyano, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 haloalkyl, C1-4 alkoxy, or C1-4 haloalkoxy;
R6, R8, and R9 are each independently selected from H, halo, NH2, OH, C1-4 alkyl, C1-4 haloalkyl, C1-4 cyanoalkyl, C1-4 alkoxy, and C1-4 haloalkoxy;
m is 0, 1, or 2; and
n is 0, 1, 2, 3, 4, or 5.