US 11,685,746 B2Granted

Heteroaryl compounds for treating Huntington's disease

AssigneePTC Therapeutics, Inc.

InventorsGuangming Chen, Anuradha Bhattacharyya, Yao Jiang, Gary Mitchell Karp, Jana Narasimhan, Anthony Turpoff, Nanjing Zhang

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Abstract

The present description relates to compounds, forms, and pharmaceutical compositions thereof and methods of using such compounds, forms, or compositions thereof for treating or ameliorating Huntington's disease. In particular, the present description relates to substituted bicyclic heteroaryl compounds of Formula (I), Formula (II), Formula (III), or Formula (IV), forms and pharmaceutical compositions thereof and methods of using such compounds, forms, or compositions thereof for treating or ameliorating Huntington's disease.

Claims9

Dependent claims

A compound of Formula (I):

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.

15 more elements

A compound selected from the group consisting of:

2-{5-[methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)phenol;
5-[2,3-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-[2,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-[3,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
2-[5-(piperazin-1-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-5-(1H-pyrazol-4-yl)phenol;
2-methyl-5-[5-(piperazin-1-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-2H-indazole-7-carbonitrile;
2-methyl-6-[5-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]imidazo[1,2-a]pyridine-8-carbonitrile;
7-fluoro-2-methyl-5-[5-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-2H-indazole;
2,8-dimethyl-6-[5-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]imidazo[1,2-b]pyridazine;
2-{5-[(3-exo)-8-azabicyclo[3.2.1]oct-3-ylamino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)phenol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)phenol;
2-methyl-5-[5-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-2H-indazole-7-carbonitrile;
2,7-dimethyl-5-[5-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-2H-indazole;
5-[2,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-[3,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
2-[5-(piperidin-4-ylamino)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-5-(1H-pyrazol-4-yl)phenol;
2-{5-[(1-methylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)phenol;
2-{5-[methyl(1-methylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)phenol;
2-methyl-5-[5-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-2H-indazole;
7-methoxy-2-methyl-5-[5-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-2H-indazole;
2-(5-{[(2R,6S)-2,6-dimethylpiperidin-4-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(1H-pyrazol-4-yl)phenol;
4-(3-hydroxy-4-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}phenyl)pyridin-2-ol;
4-(3-hydroxy 4-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}phenyl)-1-methylpyridin-2(1H)-one;
5-(1H-pyrazol-4-yl)-2-{5-[(2,2,6,6-tetramethylpiperidin-4-yl)oxy][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}phenol;
4-(3-hydroxy-4-{5-[(2,2,6,6-tetramethylpiperidin-4-yl)oxy][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}phenyl)-1-methylpyridin-2(1H)-one;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1-(2H3)methyl-1H-pyrazol-4-yl)phenol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1-methyl-1H-pyrazol-4-yl)phenol;
6,8-dimethyl-2-[5-(1,2,3,6-tetrahydropyridin-4-yl))[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]imidazo[1,2-a]pyrazine;
2-{5-[methyl(2,2,6,6-tetrahydropyridin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
5-(5-fluoro-1H-pyrazol-4-yl)-2-{5-[methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}phenol;
6,8-dimethyl-2-[5-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]imidazo[1,2-a]pyrazine;
5-(5-fluoro-1-methyl-1H-pyrazol-4-yl)-2-{5-[(2,2,6,6-tetramethylpiperidin-4-yl)oxy][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}phenol;
4-(3-hydroxy-4-{5-[methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}phenyl)-1-methylpyridin-2(1H)-one;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
5-(5-fluoro-1-methyl-1H-pyrazol-4-yl)-2-{5-[methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}phenol;
5-[1-(2H3)methyl-1H-pyrazol-4-yl]-2-{5-[methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
5-(1-ethyl-1H-pyrazol-4-yl)-2-{5-[methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-[1-(2H3)methyl-1H-pyrazol-4-yl]pyridin-3-ol;
5-(1-ethyl-1H-pyrazol-4-yl)-2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
5-(5-fluoro-1H-pyrazol-4-yl)-2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
2-(5-{methyl[(3S)-pyrrolidin-3-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(1H-pyrazol-4-yl)phenol;
2-(5-{methyl[(3R)-pyrrolidin-3-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(1H-pyrazol-4-yl)phenol;
2-(5-{methyl[(3R)-pyrrolidin-3-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(1H-pyrazol-4-yl)pyridin-3-ol;
5-bromo-2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
2-{5-[methyl(1-methylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-[1-(2H3)methyl-1H-pyrazol-4-yl]phenol;
2-{5-[(1-ethylpiperidin-4-yl)(methyl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1-methyl-1H-pyrazol-4-yl)phenol;
5-(1H-imidazol-1-yl)-2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
2-{5-[ethyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
5-(4-fluoropyrazol-1-yl)-2-[5-[methyl(4-piperidyl)amino]thiazolo[5,4-d]thiazol-2-yl]pyridin-3-ol;
5-(4-methylpyrazol-1-yl)-2-[5-[methyl(4-piperidyl)amino]thiazolo[5,4-d]thiazol-2-yl]pyridin-3-ol;
5-(thiazol-5-yl)-2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-5-[5-(6-methoxypyrimidin-4-yl)pyrazin-2-yl]-N-methyl[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-[5-(1H-imidazol-1-yl)pyrazin-2-yl]-N-methyl-N-[(2S,4R)-2-methylpiperidin-4-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(2-methyl-1H-imidazol-1-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
7-(5-{1[(2R,4S)-2-methylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)-1H-benzimidazole;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-5-[5-(2-methoxypyridin-4-yl)pyrazin-2-yl]-N-methyl[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(1H-1,2,4-triazol-1-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-[(2S,4R)-2-methylpiperidin-4-yl]-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-[(2S,4R)-2-methylpiperidin-4-yl]-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-5-[5-(3,5-dimethyl-1H-pyrazol-4-yl)pyrazin-2-yl]-N-methyl[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
7-(5-{1[(2R,4S)-2-methylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine;
N-methyl-N-[(2S,4R)-2-methylpiperidin-4-yl]-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
7-(5-{1[(2R,4S)-2-methylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine;
7-{5-[(2,2-dimethylpiperidin-4-yl)oxy][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine;
7-(5-{[(2R,4S)-2-methylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)-1H-indazole;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[6-(1H-pyrazol-4-yl)-1,2,4-triazin-3-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-[4-(1H-imidazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl]-N-methyl-N-[(2S,4R)-2-methylpiperidin-4-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
7-(5-{[(2S,4R)-2-methylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrrolo[2,3-c]pyridine;
7-(5-{[(2R,4S)-2-methylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)-1H-indole;
4-(5-{[(2R,4S)-2-methylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-7-(1H-pyrazol-4-yl)-3H-imidazo[4,5-c]pyridine;
7-(5-{[(2S,4R)-1,2-dimethylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine;
N-methyl-N-[(2R,4S)-2-methylpiperidin-4-yl]-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(5-methyl-1H-pyrazol-4-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-[(2R,4S)-2-methylpiperidin-4-yl]-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(4-methyl-1H-imidazol-1-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(1-methyl-1H-pyrazol-4-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-[4-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl]-N-methyl-N-[(2R,4S)-2-methylpiperidin-4-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-[(2R,4S)-2-methylpiperidin-4-yl]-5-[4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
4-[5-(5-{[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)pyrazin-2-yl]-1-methylpyridin-2(1H)-one;
N-methyl-N-[(2R,4S)-2-methylpiperidin-4-yl]-5-[5-(1H-pyrazol-4-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[5-(1-methyl-1H-pyrazol-4-yl)pyrazin-2-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-[(2S,4S)-2-methylpiperidin-4-yl]-5-[4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
7-[5-(6-methyl-1,6-diazaspiro[3.5]nonan-1-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine;
N-methyl-N-[(2S,4S)-2-methylpiperidin-4-yl]-5-[4-(1H-pyrazol-4-yl)-1H-indol-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-[(2S,4S)-2-methylpiperidin-4-yl]-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-[(2S,4S)-2-methylpiperidin-4-yl]-5-[5-(1H-pyrazol-4-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[6-(1H-pyrazol-4-yl)-1,2,4-triazin-3-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-(piperidin-4-yl)-5-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-[5-(1H-imidazol-1-yl)pyrazin-2-yl]-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-5-[5-(1H-imidazol-1-yl)pyrazin-2-yl]-N-methyl[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(1H-pyrazol-1-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[5-(1H-pyrazol-1-yl)pyrazin-2-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-benzimidazol-7-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-indazol-7-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-indazol-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
7-(5-{[(2S,4R)-2-methylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-indazol-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-(4-bromo-1H-indazol-7-yl)-N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-benzimidazol-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[1-methyl-4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl]-N-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[5-(1H-pyrazol-4-yl)pyrazin-2-yl]-N-[(1R,3s,5S)-1,5,8-trimethyl-8-azabicyclo[3.2.1]octan-3-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[7-(1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-(5-bromoimidazo[1,2-c]pyrimidin-8-yl)-N-methyl-N-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine
5-(5-bromoimidazo[1,2-a]pyrazin-8-yl)-N-methyl-N-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[4-(2H-1,2,3-triazol-2-yl)-1H-indol-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-(4-chloro-1H-indol-7-yl)-N-(1,2-dimethylpiperidin-4-yl)-N-methyl[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
7-(5-{[(2S,4S)-2-methylpiperidin-4-yl]oxy}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine;
N-methyl-N-[1-(propan-2-yl)piperidin-4-yl]-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1-ethylpiperidin-4-yl)-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-{5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}octahydroindolizin-7-amine;
5-(4-bromo-1H-pyrrolo[2,3-c]pyridin-7-yl)-N-(1,2-dimethylpiperidin-4-yl)-N-methyl[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-indol-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[5-(1H-pyrazol-4-yl)pyridin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[6-(1H-pyrazol-4-yl)pyridin-3-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-indol-7-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[5-(1H-pyrazol-4-yl)pyrimidin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[2-(1H-pyrazol-4-yl)pyrimidin-5-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
3-{5-[(1,2-dimethylpiperidin-4-yl)(methyl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-6-(1H-pyrazol-4-yl)pyrimidin-4(3H)-one;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[5-(1H-pyrazol-4-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[5-(1H-pyrazol-4-yl)pyridin-2-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
7-[5-(1,6-diazaspiro[3.5]nonan-1-yl) [1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine;
N-methyl-5-[6-(1H-pyrazol-4-yl)pyridin-3-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[7-(1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl) [1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[2-(1H-pyrazol-4-yl)pyrimidin-5-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
7-[5-(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl) [1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine;
N-methyl-N-(piperidin-4-yl)-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
3-{5-[methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-6-(1H-pyrazol-4-yl)pyrimidin-4(3H)-one;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[4-(1H-pyrazol-4-yl)phenyl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(1H-pyrazol-4-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
2-[5-(1H-pyrazol-4-yl)pyrazin-2-yl]-5-[(2,2,6,6-tetramethylpiperidin-4-yl)oxy][1,3]thiazolo[5,4-d][1,3]thiazole;
3-(5-{1[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-6-(1H-pyrazol-4-yl)pyrimidin-4(3H)-one;
2-{5-[methyl(octahydroindolizin-7-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
1-(5-{1[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)pyridin-2(1H)-one;
2-{5-[3-(tert-butylamino)pyrrolidin-1-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)phenol;
1-(5-{1[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(4-fluoro-1H-pyrazol-1-yl)pyridin-2(1H)-one;
1-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(4-fluoro-1H-pyrazol-1-yl)pyridin-2(1H)-one;
N-tert-butyl-1-{5-[5-(1H-pyrazol-4-yl)pyrimidin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyrrolidin-3-amine;
1-{5-[3-(tert-butylamino)pyrrolidin-1-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-4-(1H-pyrazol-4-yl)pyridin-2(1H)-one;
N-(1,2-dimethylpiperidin-4-yl)-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
3-(5-{methyl[(1R,3s,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-6-(1H-pyrazol-4-yl)pyrimidin-4(3H)-one;
N-[(1R,3s,5S)-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
1-(5-{methyl[(3R)-piperidin-3-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)pyridin-2(1H)-one;
4-(1H-pyrazol-4-yl)-1-{5-[(2,2,6,6-tetramethylpiperidin-4-yl)oxy][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-2(1H)-one;
1-{5-[(1,2-dimethylpiperidin-4-yl)(methyl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-1H-pyrrolo[2,3-b]pyridin-6-ol;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-5-[2,5-difluoro-4-(1H-pyrazol-4-yl)phenyl]-N-methyl[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-(1H-pyrrolo[2,3-c]pyridin-7-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine
N-methyl-N-[(3S)-piperidin-3-yl]-5-[5-(1H-pyrazol-4-yl)pyrimidin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[5-(1H-pyrazol-4-yl)pyrimidin-2-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-5-[5-(1H-pyrazol-4-yl)pyrazin-2-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(1H-pyrazol-4-yl)pyrazin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
1-(5-{methyl[(1R,3s,5S)-8-propyl-8-azabicyclo[3.2.1]octan-3-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)pyridin-2(1H)-one;
1-(5-{[(1R,3s,5S)-8-ethyl-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)pyridin-2(1H)-one;
N-methyl-5-[6-(1H-pyrazol-4-yl)pyridazin-3-yl]-N-(2,2,6,6-tetramethylpiperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[6-(1H-pyrazol-4-yl)pyridazin-3-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
1-(5-{methyl[(3S)-piperidin-3-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)pyridin-2(11H)-one;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-imidazol-1-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
1-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-bromopyridin-2(1H)-one;
3-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-6-(1H-pyrazol-4-yl)pyrimidin-4(3H)-one;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[6-(1H-pyrazol-4-yl)pyridin-3-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(1H-pyrazol-4-yl)pyridin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[2-(1H-pyrazol-4-yl)pyrimidin-5-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
5-[5-(2,7-diazaspiro[3.5]nonan-2-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-7-fluoro-2-methyl-2H-indazole;
2-{5-[2,5-difluoro-4-(1H-pyrazol-4-yl)phenyl][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-2,7-diazaspiro[3.5]nonane;
1-(5-{methyl[(1R,3s,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)pyridin-2(1H)-one;
2-[5-(7-methyl-1,7-diazaspiro[3.5]nonan-1-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-3-ol;
1-{5-[(1,2-dimethylpiperidin-4-yl)(methyl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-4-(1H-pyrazol-4-yl)pyridin-2(11H)-one;
1-{5-[methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-4-(1H-pyrazol-4-yl)pyridin-2(1H)-one;
2-{5-[(1,2-dimethylpiperidin-4-yl)(methyl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-indol-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-7-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
2-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-bromopyridin-3-ol;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-5-(5-bromopyrimidin-2-yl)-N-methyl[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
1-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)pyridin-2(1H)-one;
1-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-4-(1H-pyrazol-4-yl)pyridin-2(1H)-one;
2-[5-(1,7-diazaspiro[3.5]nonan-1-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(4-methyl-1H-pyrazol-1-yl)pyridin-3-ol;
6-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-hydroxy-1′-methyl[3,4′-bipyridin]-2′(1′H)-one;
2-[5-(2,6-diazaspiro[3.5]nonan-2-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-(5-{[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(4-fluoro-1H-pyrazol-1-yl)pyridin-3-ol;
N-[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl]-N-methyl-5-[5-(1H-pyrazol-4-yl)pyrimidin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
1-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-4-(1H-pyrazol-4-yl)pyridin-2(1H)-one;
2-[5-(7-methyl-2,7-diazaspiro[3.5]nonan-2-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-3-ol;
5-(1H-pyrazol-4-yl)-2-[5-(spiro[8-azabicyclo[3.2.1]octane-3,3′-azetidin]-1′-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]pyridin-3-ol;
5-(1H-pyrazol-4-yl)-2-[5-(spiro[8-azabicyclo[3.2.1]octane-3,3′-azetidin]-1′-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]phenol;
2-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(2-methyl-1,3-thiazol-5-yl)pyridin-3-ol;
5-[2-methoxy-4-(1H-pyrazol-4-yl)phenyl]-N-methyl-N-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
N-methyl-N-(piperidin-4-yl)-5-[5-(1H-pyrazol-4-yl)pyrimidin-2-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
2-(5-1{[(2R,4S)-2-(hydroxymethyl)piperidin-4-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(1H-pyrazol-4-yl)phenol;
2-(5-{1[(1R,3s,5S)-8-azabicyclo[3.2.1]octan-3-yl](methyl)amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-{5-[(1-cyclopropylpiperidin-4-yl)(methyl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-(5-{methyl[1-(propan-2-yl)piperidin-4-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-{5-[methyl(1-propylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-{5-[(1-ethylpiperidin-4-yl)(methyl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-[5-(piperidin-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-5-(1H-pyrazol-4-yl)phenol;
2-[5-(2,7-diazaspiro[3.5]nonan-2-yl)[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-([1,2,4]triazolo[4,3-a]pyridin-6-yl)pyridin-3-ol;
2-{5-[(3aR,6aS)-5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)phenol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-1,2,4-triazol-1-yl)pyridin-3-ol;
2-(5-{methyl[(3S)-pyrrolidin-3-yl]amino}[1,3]thiazolo[5,4-d][1,3]thiazol-2-yl)-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(2H-1,2,3-triazol-2-yl)pyridin-3-ol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-1,2,3-triazol-1-yl)pyridin-3-ol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1,2-thiazol-4-yl)pyridin-3-ol;
2-{5-[methyl(1-methylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-{5-[ethyl(1-methylpiperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(1H-pyrazol-4-yl)pyridin-3-ol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(3-methyl-1H-pyrazol-4-yl)pyridin-3-ol;
5-(5-chloro-1H-pyrazol-4-yl)-2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
5-(4-methyl-1H-imidazol-1-yl)-2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(2-methyl-1,3-thiazol-5-yl)pyridin-3-ol;
5-(2-methyl-1,3-oxazol-5-yl)-2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}pyridin-3-ol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(6-methylpyridazin-4-yl)pyridin-3-ol;
2-{5-[methyl(piperidin-4-yl)amino][1,3]thiazolo[5,4-d][1,3]thiazol-2-yl}-5-(pyridazin-4-yl)pyridin-3-ol;
and
N-methyl-N-(piperidin-4-yl)-5-[7-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-4-yl][1,3]thiazolo[5,4-d][1,3]thiazol-2-amine;
wherein a form of the compound is selected from the group consisting of salt, hydrate, solvate, racemate, enantiomer, diastereomer, stereoisomer, and tautomer form thereof.

212 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/254,848Filed 25 Jun 2019 · us provisional application
Priority: 27 Jun 2018
Published: US 2021/0380603 A19 Dec 2021
Granted: 27 Jun 2023
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 513/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 25/00
Drugs for disorders of the nervous system
A61P 25/14
Drugs for disorders of the nervous system: for treating abnormal movements, e.g. chorea, dyskinesia
A61P 25/28
Drugs for disorders of the nervous system: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents,…

Family

Application62/690,605Us provisional application · filed 27 Jun 2018
US 2021/0380603 A1Pre-grant publication · published 9 Dec 2021
US 11,685,746 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of Formula (I):

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.

15 more elements

Facts

Application

17/254,848Filed 25 Jun 2019 · us provisional application

Priority

27 Jun 2018

Published

US 2021/0380603 A19 Dec 2021

Granted

27 Jun 2023

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 513/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 25/00
Drugs for disorders of the nervous system
A61P 25/14
Drugs for disorders of the nervous system: for treating abnormal movements, e.g. chorea, dyskinesia
A61P 25/28
Drugs for disorders of the nervous system: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents,…