US 11,685,746 B2
Heteroaryl compounds for treating Huntington's disease
Guangming Chen, Bridgewater, NJ (US); Anuradha Bhattacharyya, Edison, NJ (US); Yao Jiang, South Plainfield, NJ (US); Gary Mitchell Karp, Princeton Junction, NJ (US); Jana Narasimhan, Scotch Plains, NJ (US); Anthony Turpoff, Hillsborough, NJ (US); and Nanjing Zhang, Princeton, NJ (US)
Assigned to PTC Therapeutics, Inc., South Plainfield, NJ (US)
Appl. No. 17/254,848
Filed by PTC THERAPEUTICS, INC., South Plainfield, NJ (US)
PCT Filed Jun. 25, 2019, PCT No. PCT/US2019/038900
§ 371(c)(1), (2) Date Dec. 21, 2020,
PCT Pub. No. WO2020/005882, PCT Pub. Date Jan. 2, 2020.
Claims priority of provisional application 62/690,605, filed on Jun. 27, 2018.
Prior Publication US 2021/0380603 A1, Dec. 9, 2021
Int. Cl. C07D 513/04 (2006.01); C07D 519/00 (2006.01)
CPC C07D 513/04 (2013.01) [C07D 519/00 (2013.01)] 9 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a form thereof, wherein:
X is selected from the group consisting of N—Rb, O, and a bond;
Rb is selected from the group consisting of hydrogen and C1-6 alkyl;
R1 is heterocyclyl,
wherein heterocyclyl is a saturated or partially unsaturated 3-7 membered monocyclic, 6-10 membered bicyclic or 13-16 membered polycyclic ring system having 1, 2, or 3 heteroatom ring members independently selected from N, O, or S, and
wherein heterocyclyl is optionally substituted where allowed by available valences with one, two, three, or four R3 substituents;
R3 is, in each instance, independently selected from the group consisting of cyano, halogen, hydroxy, C1-6 alkyl, deutero-C1-4alkyl, halo-C1-6alkyl, C1-6 alkoxy, halo-C1-6 alkoxy, C1-6alkoxy-C1-6 alkyl, amino, C1-6 alkyl-amino, (C1-6 alkyl)2-amino, amino-C1-6alkyl, hydroxy-C1-6 alkyl, and C3-10 cycloalkyl;
R2 is selected from the group consisting of phenyl and heteroaryl,
wherein heteroaryl is a 3-7 membered monocyclic or 6-10 membered bicyclic ring system having 1, 2, 3, or 4 heteroatom ring members independently selected from N, O, or S, and
wherein phenyl or heteroaryl is optionally substituted where allowed by available valences with one, two, or three R4 substituents and optionally, with one additional R5 substituent, or
wherein, alternatively, phenyl or heteroaryl is optionally substituted where allowed by available valences with one, two, three, or four R4 substituents;
R4 is, in each instance, independently selected from the group consisting of cyano, halogen, hydroxy, C1-6 alkyl, deutero-C1-4alkyl, halo-C1-6alkyl, C1-6 alkoxy, halo-C1-6 alkoxy, C1-6alkoxy-C1-6 alkyl, C1-6 alkoxy-carbonyl, amino, C1-6alkyl-amino, (C1-6 alkyl)2-amino, amino-C1-6alkyl, and hydroxy-C1-6 alkyl;
R5 is heteroaryl;
wherein heteroaryl is a 3-7 membered monocyclic or 6-10 membered bicyclic ring system having 1, 2, 3, or 4 heteroatom ring members independently selected from N, O, or S, and
wherein, each instance of heteroaryl is optionally substituted where allowed by available valences with one, two or three R6 substituents; and
R6 is, in each instance, independently selected from the group consisting of cyano, halogen, hydroxy, C1-6 alkyl, deutero-C1-4alkyl, halo-C1-6alkyl, C1-6 alkoxy, halo-C1-6 alkoxy, C1-6alkoxy-C1-6 alkyl, C1-6 alkoxy-carbonyl, amino, C1-6alkyl-amino, (C1-6 alkyl)2-amino, amino-C1-8alkyl, and hydroxy-C1-6 alkyl;
wherein a form of the compound is selected from the group consisting of a salt, hydrate, solvate, racemate, enantiomer, diastereomer, stereoisomer, and tautomer form thereof.