US 12,421,224 B2
Azetidinyl O-glycoprotein-2-acetamido-2-deoxy-3-D-glucopyranosidase inhibitors
Nathan Genung, Charlestown, MA (US); Kevin M. Guckian, Northborough, MA (US); Jeffrey Vessels, Marlborough, MA (US); Lei Zhang, Westford, MA (US); Ryan Gianatassio, Everett, MA (US); Edward Yin Shiang Lin, Ashland, MA (US); and Zhili Xin, Lexington, MA (US)
Assigned to BIOGEN MA INC., Cambridge, MA (US)
Appl. No. 17/435,125
Filed by BIOGEN MA INC., Cambridge, MA (US)
PCT Filed Mar. 6, 2020, PCT No. PCT/US2020/021479
§ 371(c)(1), (2) Date Aug. 31, 2021,
PCT Pub. No. WO2020/185593, PCT Pub. Date Sep. 17, 2020.
Claims priority of provisional application 62/815,553, filed on Mar. 8, 2019.
Prior Publication US 2022/0259197 A1, Aug. 18, 2022
Int. Cl. C07D 417/14 (2006.01); C07D 495/04 (2006.01)
CPC C07D 417/14 (2013.01) [C07D 495/04 (2013.01)] 20 Claims
 
1. A compound represented by the following structural formula:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
Ar is an optionally substituted 6- to 10-membered aryl or an optionally substituted 5- to 10-membered heteroaryl;
X is —CR2R2—, —(CR2R2)O—, —NRd—, or —NRd(CR2R2);
Y1 and Y2 are each CRc or N, wherein at least one of Y1 or Y2 is N;
Z is —CR2R2—, —C(═O)—, —(CR2R2)2—, or —CH2C(═O)—;
Rc is —H, halo, —C1-C4 alkyl, or —C1-C4 haloalkyl;
Rd is —H or —C1-C4 alkyl;
n is 0 or an integer from 1 to 5;
when n is other than 0, R1, for each occurrence, is independently halo, —C1-C4 alkyl, —C1-C4 haloalkyl, or —C1-C4 alkoxy;
R2, for each occurrence, is independently —H, halo, —C1-C4 alkyl, —C1-C4 haloalkyl, —C3-C10 cycloalkyl, or —C3-C10 halocycloalkyl;
or alternatively two R2 together with the carbon atom to which they are attached form a —C3-C10 cycloalkyl;
R3 is —H or —C1-C4 alkyl; and
R4 is —H, —C1-C4 alkyl, —C1-C4 haloalkyl, or —C3-C6 cycloalkyl;
or alternatively R3 and R4 taken together with their intervening atoms form an optionally substituted 5- to 7-membered heterocyclyl.