US 9,809,537 B2
Glycosidase inhibitors and uses thereof
Ernest J. McEachern, Vancouver (CA); Jianyu Sun, Burnaby (CA); David J. Vocadlo, Burnaby (CA); Yuanxi Zhou, Burnaby (CA); Yongbao Zhu, Burnaby (CA); and Harold G. Selnick, West Point, PA (US)
Assigned to Alectos Therapeutics Inc., Burnaby (CA); and Merck Sharp & Dohme Corp., Rahway, NJ (US)
Appl. No. 14/424,873
Filed by Alectos Therapeutics Inc., Burnaby (CA); and Merck Sharp & Dohme Corp., Rahway, NJ (US)
PCT Filed Aug. 29, 2013, PCT No. PCT/CA2013/050672
§ 371(c)(1), (2) Date Feb. 27, 2015,
PCT Pub. No. WO2014/032188, PCT Pub. Date Mar. 6, 2014.
Claims priority of provisional application 61/695,987, filed on Aug. 31, 2012.
Prior Publication US 2015/0274656 A1, Oct. 1, 2015
Int. Cl. C07D 207/12 (2006.01); A61K 31/40 (2006.01); A61K 31/428 (2006.01); A61K 31/4439 (2006.01); C07D 401/06 (2006.01); C07D 417/06 (2006.01); C12N 9/99 (2006.01); C07D 207/16 (2006.01)
CPC C07D 207/12 (2013.01) [A61K 31/40 (2013.01); A61K 31/428 (2013.01); A61K 31/4439 (2013.01); C07D 207/16 (2013.01); C07D 401/06 (2013.01); C07D 417/06 (2013.01); C12N 9/99 (2013.01); C12Y 302/01169 (2013.01)] 6 Claims
 
1. A compound of Formula (I) or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Drawing
wherein
R1 is selected from the group consisting of: CH2NR8R9, wherein R8 is H and R9 is C1-6 acyl, and (CH2)nC(O)NR102, wherein n is 1, and one R10 is H and the other R10 is C1-6 alkyl;
R2 is H and R3 is OH, or R2 is H and R3 is H, or R2 is H and R3 is F, or R2 is F and R3 is H, or R2 is F and R3 is F, or R2 is OH and R3 is H;
R4 is H and R5 is OH, or R4 is H and R5 is H, or R4 is H and R5 is F, or R4 is F and R5 is H, or R4 is F and R5 is F, or R4 is OH and R5 is H;
R6 is selected from the group consisting of: CH3, CH2F, and CHF2; and
R7 is selected from the group consisting of: C1-18 alkyl, C2-10 alkenyl, C2-10 alkynyl, C7-20 arylalkyl, C8-20 arylalkenyl, and C8-20 arylalkynyl, each optionally substituted from one to four substituents with one of more of halo, OH, OCF3, CN, SO2NH2, SO2Me, C(O)NH2, CH2F, CHF2, CF3, CH2CH2F, CH2CF3, CH2CH2CH2F, C1-6 alkyl, C1-6 alkoxy, or C3-7 cycloalkyl,
with the proviso that the compound excludes N-(((2R,3R,4R,5R)-3,4-dihydroxy-5-methylpyrrolidin-2-yl)methyl)acetamide.