US 2024/0390338 A1Published application

Methods for treating neurogenerative diseases

AssigneePTC Therapeutics, Inc.

InventorsScott J. Barraza, Jeffrey K. Trimmer, Yong Yu, Xiaoyan Zhang

Life of this patent

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Abstract

The present description relates to methods of treating neurodegenerative diseases characterized by the accumulation of aberrant forms of the microtubule associated protein Tau (MAPT) using substituted thieno[3,2-b]pyridine compounds, forms, and pharmaceutical compositions thereof.

Claims14

Dependent claims

A method for treating a neurodegenerative disease characterized by the accumulation of aberrant forms of the microtubule associated protein Tau (MAPT) in a subject in need thereof, comprising administering to said subject an effective amount of a compound of Formula (I):

or a form thereof, wherein
R1 is selected from the group consisting of phenyl and heteroaryl,
wherein heteroaryl is a 5-8 membered monocyclic or bicyclic aromatic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S, and
wherein phenyl or heteroaryl are optionally substituted with one, two, three, or four, independently selected R1a substituents;
R1a is independently selected from the group consisting of cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, and C1-6alkoxy;
R3 is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, and C1-6alkyl-amino,
wherein C1-6alkyl, C2-6alkenyl, and C2-6alkynyl may optionally contain a chiral carbon having an (R) or (S) configuration, and
wherein C1-6alkyl, C2-6alkenyl, or C2-6alkynyl are optionally substituted with one, two, three, or four independently selected R3a substituents;
R3a is independently selected from the group consisting of cyano, halo, hydroxy, oxo, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, halo-C1-6alkoxy, carboxyl, amino, C1-6alkoxy-carbonyl, C1-6alkyl-amino, halo-C1-6alkyl-amino, (C1-6alkyl)2-amino, phenyl-amino, heterocyclyl-amino, heteroaryl-amino, phenyl-(C1-6alkyl)-amino, heterocyclyl-(C1-6alkyl)-amino, heteroaryl-(C1-6alkyl)-amino, C1-6alkyl-thio, C1-6alkyl-sulfoxyl, and C1-6alkyl-sulfonyl,
wherein heterocyclyl is a 3-7 membered monocyclic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S,
wherein heteroaryl is a 5-8 membered monocyclic or bicyclic aromatic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S, and
wherein phenyl, heterocyclyl, and heteroaryl is optionally substituted with one, two, three or four independently selected R3a′ substituents;
R3a′ is independently selected from the group consisting of cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, and amino;
R4 is selected from the group consisting of hydrogen, cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, halo-C1-6alkoxy, amino, C1-6alkyl-amino, (C1-6alkyl)2-amino, C3-10cycloalkyl, phenyl, heterocyclyl, and heteroaryl,
wherein heterocyclyl is a 3-7 membered monocyclic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S,
wherein heteroaryl is a 5-8 membered monocyclic or bicyclic aromatic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S, and
wherein each instance of C1-6alkyl, C3-10cycloalkyl, phenyl, heterocyclyl, or heteroaryl are optionally substituted with one, two, three, or four independently selected R4a substituents;
R4a is independently selected from the group consisting of cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, and C1-6alkoxy;
R5 is selected from the group consisting of hydrogen, cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, carbamoyl, C3-10cycloalkyl, and heterocyclyl,
wherein heterocyclyl is a 3-7 membered monocyclic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S;
R6 is selected from the group consisting of hydrogen, halo, and C1-6alkyl;
and
wherein the form of the compound is selected from the group consisting of a salt, hydrate, solvate, and tautomer form thereof.

20 more elements

5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
1-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)ethan-1-ol;
1-(5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)ethan-1-ol;
(5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)methanol;
3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
3-chloro-5-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
3-bromo-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-5-carbonitrile;
7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-3,5-dicarbonitrile;
5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-3-carbonitrile;
5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridine-3-carbonitrile;
7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridine-3,5-dicarbonitrile;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2R)-2-amino-3-(5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminobutyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridine-5-carbonitrile;
2-[(1S)-1-aminoethyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(1R)-1-aminoethyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(1R)-1-aminoethyl]-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(1S)-1-aminoethyl]-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
5-chloro-N-[(furan-2-yl)methyl]-2-[(methylamino)methyl]thieno[3,2-b]pyridin-7-amine;
5-chloro-N-[(furan-2-yl)methyl]-3-methyl-2-[(1S)-1-(methylamino)ethyl]thieno[3,2-b]pyridin-7-amine;
5-chloro-N-[(furan-2-yl)methyl]-3-methyl-2-[(methylamino)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(2-fluorophenyl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(1S)-1-amino-2-methylpropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(1R)-1-amino-2-methylpropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
5-chloro-N-[(furan-2-yl)methyl]-3-methyl-2-[(1S)-2-methyl-1-(methylamino)propyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminobutyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(3-fluoropyridin-4-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2R)-2-amino-3-(3,5-dichloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol;
2-[(2R)-2-amino-3-methoxypropyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2R)-2-amino-3-(3-bromo-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol;
5-chloro-N-[(furan-2-yl)methyl]-3-methyl-2-[(2S)-2-(methylamino)propyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-methoxypropyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-methoxypropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-fluorobutyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(3S)-3-amino-4-(3,5-dichloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butan-1-ol;
2-[(2S)-2-aminopropyl]-3-bromo-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridine-5-carbonitrile;
2-[(2S)-2-aminopropyl]-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridine-3,5-dicarbonitrile;
2-[(2S)-2-aminopropyl]-5-chloro-3-cyclopropyl-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-3-methyl-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-5-carbonitrile;
2-[(1S)-1-aminoethyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(1R)-1-aminoethyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2R)-2-amino-3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)propan-1-ol;
2-[(2S)-2-amino-3-fluoropropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-3-chloro-5-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-methylpentyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-methylpentyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-(trifluoromethoxy)propyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2R)-3-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)-2-[(trifluoromethyl)amino]propan-1-ol;
2-[(2S)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-3-fluoropropyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-methylpentyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2R)-2-amino-3-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol;
2-[(2R)-2-aminobut-3-en-1-yl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminobutyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-fluorobutyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminobutyl]-5-chloro-3-cyclopropyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-3-cyclopropyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminobutyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-methylpentyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-methylpentyl]-5-chloro-3-cyclopropyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminobutyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminobutyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminobutyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminobutyl]-5-chloro-3-cyclopropyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-3-cyclopropyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-fluorobutyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(3S)-3-amino-4-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butan-1-ol;
2-[(2R)-2-amino-3-fluoropropyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-fluorobutyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-fluorobutyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-fluoropropyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-fluorobutyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-5-chloro-3-cyclopropyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-fluorobutyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-fluorobutyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-4-fluorobutyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(3S)-3-amino-4-(3-bromo-5-chloro-7-{[(2-fluorophenyl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butan-1-ol;
2-[(2S)-2-aminopropyl]-3-bromo-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-5-carbonitrile;
2-[(2S)-2-aminopropyl]-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-3,5-dicarbonitrile;
(3S)-3-amino-4-(3-bromo-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butanenitrile;
2-[(2R)-2-amino-3-(methylsulfanyl)propyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
(3S′)-3-amino-4-(5-chloro-3-methyl-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butanenitrile;
(3S)-3-amino-4-(3,5-dichloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butanenitrile;
2-[(2S)-2-amino-4,4-difluorobutyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-(methanesulfonyl)propyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridine-3-carbonitrile;
2-[(2S)-2-aminopropyl]-5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-3-carbonitrile;
(3S)-3-amino-4-(5-chloro-7-([(furan-2-yl)methyl]amino)-3-methylthieno[3,2-b]pyridin-2-yl)butanenitrile;
2-[(2S)-2-aminopropyl]-3-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-5-carbonitrile;
2-[(2R)-2-amino-3-(methanesulfonyl)propyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-(methylsulfanyl)propyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-D-alanine;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N,N-dimethyl-D-alaninamide;
2-[(2R)-2-amino-3-(methanesulfonyl)propyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-amino-3-(methylsulfanyl)propyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R)-2-aminobut-3-en-1-yl]-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
343,5-dichloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)-N-(2-fluorophenyl)-D-alaninamide;
343,5-dichloro-7-([(furan-2-yl)methyl]amino)thieno[3,2-b]pyridin-2-yl)-D-alanine;
3-(3,5-dichloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)-N-phenyl-D-alaninamide;
2-[(2R)-2-aminobut-3-yn-1-yl]-3-methyl-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
343,5-dichloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)-N-(2-fluorophenyl)-D-alaninamide;
2-[(2R,3S)-2-amino-3-fluorobutyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R,3S)-2-amino-3-fluorobutyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2S)-2-amino-1-(3,5-dichloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol;
2-[(2R,3S)-2-amino-3-fluorobutyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(5-fluoro-1,3-thiazol-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S)-2-amino-1-fluoropropyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
methyl 3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-D-alaninate;
2-[(2S)-2-amino-1,1-difluoropropyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-(4-cyanophenyl)-D-alaninamide;
3-(5-chloro-7-([(furan-2-yl)methyl]amino)-3-methylthieno[3,2-b]pyridin-2-yl)-N-pyridin-2-yl-D-alaninamide;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-pyrazin-2-yl-D-alaninamide;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methoxythieno[3,2-b]pyridin-7-amine;
5-chloro-N-[(furan-2-yl)methyl]-3-methoxythieno[3,2-b]pyridin-7-amine;
5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-3-ol;
2-[(2S)-2-aminopropyl]-5-chloro-3-(difluoromethoxy)-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-pyridin-4-yl-D-alaninamide;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-methyl-N-phenyl-D-alaninamide;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-(4-methylphenyl)-D-alaninamide;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-(3-chlorophenyl)-D-alaninamide;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-(3-methoxyphenyl)-D-alaninamide;
3-(5-chloro-7-([(furan-2-yl)methyl]amino)-3-methylthieno[3,2-b]pyridin-2-yl)-N-(1-methyl-1H-pyrazol-5-yl)-D-alaninamide;
2-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)propan-1-ol;
2-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)propane-1,2-diol;
2-(I-aminopropan-2-yl)-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
5-chloro-3-(difluoromethoxy)-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
2-[(2R,3S)-3-aminobutan-2-yl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-[(2S,3S)-3-aminobutan-2-yl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
2-(2-aminoethyl)-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol;
2-[(2S)-2-amino-1-fluoropropyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-one;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-one;
2-[(2,S)-2-amino-1-fluoropropyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-one;
2-[(2S)-2-amino-1-fluoropropyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
(2R)-2-amino-3-(5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol;
N2-[(2S)-2-aminopropyl]-5-chloro-3-methyl-N7-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridine-2,7-diamine;
N2-[(2R)-2-aminopropyl]-5-chloro-3-methyl-N7-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridine-2,7-diamine;
(2R,3R)-3-amino-4-(3-bromo-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butan-2-ol;
2-[(2R)-2-aminobut-3-yn-1-yl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine;
and
[(2R)-2-amino-3-(3,5-dichloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propyl](methyl)sulfaniumolate;
wherein the form of the compound is selected from the group consisting of a salt, hydrate, solvate, and tautomer form thereof.

166 more elements

3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
3-chloro-5-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(2R)-2-amino-3-(5-chloro-7-[(furan-2-yl)methyl]amino)thieno[3,2-b]pyridin-2-yl)propan-1-ol dihydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminobutyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-7-[(furan-2-yl)methyl]amino)-3-methylthieno[3,2-b]pyridine-5-carbonitrile trifluoroacetate;
2-[(1S)-1-aminoethyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(1R)-1-aminoethyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(1R)-1-aminoethyl]-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(1S)-1-aminoethyl]-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
5-chloro-N-[(furan-2-yl)methyl]-2-[(methylamino)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
5-chloro-N-[(furan-2-yl)methyl]-3-methyl-2-[(1S)-1-(methylamino)ethyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
5-chloro-N-[(furan-2-yl)methyl]-3-methyl-2-[(methylamino)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(2-fluorophenyl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(1S)-1-amino-2-methylpropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(1R)-1-amino-2-methylpropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine hydrochloride;
5-chloro-N-[(furan-2-yl)methyl]-3-methyl-2-[(1S)-2-methyl-1-(methylamino)propyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminobutyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(3-fluoropyridin-4-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(2R)-2-amino-3-(3,5-dichloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol dihydrochloride;
2-[(2R)-2-amino-3-methoxypropyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(2R)-2-amino-3-(3-bromo-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol dihydrochloride;
5-chloro-N-[(furan-2-yl)methyl]-3-methyl-2-[(2S)-2-(methylamino)propyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminopropyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-methoxypropyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-methoxypropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine formate;
2-[(2S)-2-amino-4-fluorobutyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(3S)-3-amino-4-(3,5-dichloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butan-1-ol dihydrochloride;
2-[(2S)-2-aminopropyl]-3-bromo-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridine-5-carbonitrile hydrochloride;
2-[(2S)-2-aminopropyl]-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridine-3,5-dicarbonitrile hydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-3-cyclopropyl-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminopropyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-3-methyl-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-5-carbonitrile formate;
2-[(1 S)-1-aminoethyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(1R)-1-aminoethyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(2R)-2-amino-3-(5-chloro-7-([(furan-2-yl)methyl]amino)-3-methylthieno[3,2-b]pyridin-2-yl)propan-1-ol dihydrochloride;
2-[(2S)-2-amino-3-fluoropropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-3-chloro-5-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-4-methylpentyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-amino-4-methylpentyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2R)-2-amino-3-(trifluoromethoxy)propyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine formate;
(2R)-3-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)-2-[(trifluoromethyl)amino]propan-1-ol formate;
2-[(2S)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-3-fluoropropyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-4-methylpentyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(2R)-2-amino-3-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol dihydrochloride;
2-[(2R)-2-aminobut-3-en-1-yl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminobutyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-4-fluorobutyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminobutyl]-5-chloro-3-cyclopropyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-3-cyclopropyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminobutyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-amino-4-methylpentyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-amino-4-methylpentyl]-5-chloro-3-cyclopropyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminobutyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminobutyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminobutyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine formate;
2-[(2S)-2-aminobutyl]-5-chloro-3-cyclopropyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-3-cyclopropyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-4-fluorobutyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(3S)-3-amino-4-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butan-1-ol dihydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-3,5-dichloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-4-fluorobutyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-4-fluorobutyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-fluoropropyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-4-fluorobutyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-3-cyclopropyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
2-[(2S)-2-amino-4-fluorobutyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-4-fluorobutyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-4-fluorobutyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine formate;
(3S)-3-amino-4-(3-bromo-5-chloro-7-{[(2-fluorophenyl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butan-1-ol dihydrochloride;
2-[(2S)-2-aminopropyl]-3-bromo-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-5-carbonitrile formate;
2-[(2S)-2-aminopropyl]-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-3,5-dicarbonitrile formate;
(3S)-3-amino-4-(3-bromo-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butanenitrile formate;
2-[(2R)-2-amino-3-(methylsulfanyl)propyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
(3S)-3-amino-4-(5-chloro-3-methyl-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butanenitrile dihydrochloride;
(3S)-3-amino-4-(3,5-dichloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butanenitrile dihydrochloride;
2-[(2S)-2-amino-4,4-difluorobutyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-(methanesulfonyl)propyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-7-([(furan-2-yl)methyl]amino)thieno[3,2-b]pyridine-3-carbonitrile formate;
2-[(2S)-2-aminopropyl]-5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-3-carbonitrile formate;
(3S)-3-amino-4-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)butanenitrile dihydrochloride;
2-[(2S)-2-aminopropyl]-3-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridine-5-carbonitrile formate;
2-[(2R)-2-amino-3-(methanesulfonyl)propyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-(methylsulfanyl)propyl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine hydrochloride;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-D-alanine dihydrochloride;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N,N-dimethyl-D-alaninamide dihydrochloride;
2-[(2R)-2-amino-3-(methanesulfonyl)propyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-amino-3-(methylsulfanyl)propyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R)-2-aminobut-3-en-1-yl]-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine formate;
3-(3,5-dichloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)-N-(2-fluorophenyl)-D-alaninamide dihydrochloride;
343,5-dichloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)-D-alanine dihydrochloride;
343,5-dichloro-7-([(furan-2-yl)methyl]amino)thieno[3,2-b]pyridin-2-yl)-N-phenyl-D-alaninamide hydrochloride;
2-[(2R)-2-aminobut-3-yn-1-yl]-3-methyl-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
3-(3,5-dichloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)-N-(2-fluorophenyl)-D-alaninamide dihydrochloride;
2-[(2R,3S)-2-amino-3-fluorobutyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2R,3S)-2-amino-3-fluorobutyl]-5-chloro-3-methyl-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(2S)-2-amino-1-(3,5-dichloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol dihydrochloride;
2-[(2R,3S)-2-amino-3-fluorobutyl]-5-chloro-3-methyl-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(5-fluoro-1,3-thiazol-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S)-2-amino-1-fluoropropyl]-3,5-dichloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine formate;
methyl 3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-D-alaninate dihydrochloride;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-(4-cyanophenyl)-D-alaninamide hydrochloride;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-pyridin-2-yl-D-alaninamide hydrochloride;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-pyrazin-2-yl-D-alaninamide hydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-N-[(furan-2-yl)methyl]-3-methoxythieno[3,2-b]pyridin-7-amine dihydrochloride;
5-chloro-N-[(furan-2-yl)methyl]-3-methoxythieno[3,2-b]pyridin-7-amine hydrochloride;
5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-3-ol hydrochloride;
2-[(2S)-2-aminopropyl]-5-chloro-3-(difluoromethoxy)-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine formate;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-pyridin-4-yl-D-alaninamide hydrochloride;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-methyl-N-phenyl-D-alaninamide hydrochloride;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-(4-methylphenyl)-D-alaninamide hydrochloride;
3-(5-chloro-7-([(furan-2-yl)methyl]amino)-3-methylthieno[3,2-b]pyridin-2-yl)-N-(3-chlorophenyl)-D-alaninamide hydrochloride;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-(3-methoxyphenyl)-D-alaninamide hydrochloride;
3-(5-chloro-7-{[(furan-2-yl)methyl]amino}-3-methylthieno[3,2-b]pyridin-2-yl)-N-(1-methyl-1H-pyrazol-5-yl)-D-alaninamide hydrochloride;
2-(1-aminopropan-2-yl)-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine formate;
2-[(2R,3S)-3-aminobutan-2-yl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-[(2S,3S)-3-aminobutan-2-yl]-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine dihydrochloride;
2-(2-aminoethyl)-5-chloro-N-[(furan-2-yl)methyl]-3-methylthieno[3,2-b]pyridin-7-amine formate;
(2S)-2-amino-1-(3-bromo-5-chloro-7-([(furan-2-yl)methyl]amino)thieno[3,2-b]pyridin-2-yl)propan-1-ol dihydrochloride;
2-[(2S)-2-amino-1-fluoropropyl]-3-bromo-5-chloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol dihydrochloride;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-one dihydrochloride;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-one dihydrochloride;
2-[(2S)-2-amino-1-fluoropropyl]-3-bromo-5-chloro-N-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol dihydrochloride;
(2S)-2-amino-1-(3-bromo-5-chloro-7-{[(1,3-thiazol-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-one dihydrochloride;
2-[(2S)-2-amino-1-fluoropropyl]-3-bromo-5-chloro-N-[(1,3-thiazol-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
(2R)-2-amino-3-(5-chloro-7-{[(thiophen-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)propan-1-ol formate;
N2-[(2S)-2-aminopropyl]-5-chloro-3-methyl-N7-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridine-2,7-diamine hydrochloride;
N2-[(2R)-2-aminopropyl]-5-chloro-3-methyl-N7-[(thiophen-2-yl)methyl]thieno[3,2-b]pyridine-2,7-diamine hydrochloride;
(2R,3R)-3-amino-4-(3-bromo-5-chloro-7-{[(furan-2-yl)methyl]amino}thieno[3,2-b]pyridin-2-yl)butan-2-ol hydrochloride;
and
2-[(2R)-2-aminobut-3-yn-1-yl]-3,5-dichloro-N-[(furan-2-yl)methyl]thieno[3,2-b]pyridin-7-amine dihydrochloride;
wherein the form of the compound salt is selected from the group consisting of a salt, hydrate, solvate, and tautomer form thereof.

148 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/689,761Filed 6 Sep 2022
Priority: 7 Sep 2021
Published: 28 Nov 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

A61K 31/4365
Ortho- or peri-condensed with heterocyclic ring systems: the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
A61P 25/16
For treating abnormal movements, e.g. chorea, dyskinesia: anti-Parkinson drugs
A61K 31/444
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
A61K 31/497
Non-condensed pyrazines: containing further heterocyclic rings

Family

Application63/260,943Us provisional application · filed 7 Sep 2021
US 2024/0390338 A1This patent

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

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Abstract

or a form thereof, wherein
R1 is selected from the group consisting of phenyl and heteroaryl,
wherein heteroaryl is a 5-8 membered monocyclic or bicyclic aromatic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S, and
wherein phenyl or heteroaryl are optionally substituted with one, two, three, or four, independently selected R1a substituents;
R1a is independently selected from the group consisting of cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, and C1-6alkoxy;
R3 is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, and C1-6alkyl-amino,
wherein C1-6alkyl, C2-6alkenyl, and C2-6alkynyl may optionally contain a chiral carbon having an (R) or (S) configuration, and
wherein C1-6alkyl, C2-6alkenyl, or C2-6alkynyl are optionally substituted with one, two, three, or four independently selected R3a substituents;
R3a is independently selected from the group consisting of cyano, halo, hydroxy, oxo, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, halo-C1-6alkoxy, carboxyl, amino, C1-6alkoxy-carbonyl, C1-6alkyl-amino, halo-C1-6alkyl-amino, (C1-6alkyl)2-amino, phenyl-amino, heterocyclyl-amino, heteroaryl-amino, phenyl-(C1-6alkyl)-amino, heterocyclyl-(C1-6alkyl)-amino, heteroaryl-(C1-6alkyl)-amino, C1-6alkyl-thio, C1-6alkyl-sulfoxyl, and C1-6alkyl-sulfonyl,
wherein heterocyclyl is a 3-7 membered monocyclic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S,
wherein heteroaryl is a 5-8 membered monocyclic or bicyclic aromatic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S, and
wherein phenyl, heterocyclyl, and heteroaryl is optionally substituted with one, two, three or four independently selected R3a′ substituents;
R3a′ is independently selected from the group consisting of cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, and amino;
R4 is selected from the group consisting of hydrogen, cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, halo-C1-6alkoxy, amino, C1-6alkyl-amino, (C1-6alkyl)2-amino, C3-10cycloalkyl, phenyl, heterocyclyl, and heteroaryl,
wherein heterocyclyl is a 3-7 membered monocyclic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S,
wherein heteroaryl is a 5-8 membered monocyclic or bicyclic aromatic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S, and
wherein each instance of C1-6alkyl, C3-10cycloalkyl, phenyl, heterocyclyl, or heteroaryl are optionally substituted with one, two, three, or four independently selected R4a substituents;
R4a is independently selected from the group consisting of cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, and C1-6alkoxy;
R5 is selected from the group consisting of hydrogen, cyano, halo, hydroxy, C1-6alkyl, halo-C1-6alkyl, C1-6alkoxy, carbamoyl, C3-10cycloalkyl, and heterocyclyl,
wherein heterocyclyl is a 3-7 membered monocyclic carbon atom ring structure radical containing 1-3 heteroatoms selected from N, O, and S;
R6 is selected from the group consisting of hydrogen, halo, and C1-6alkyl;
and
wherein the form of the compound is selected from the group consisting of a salt, hydrate, solvate, and tautomer form thereof.

20 more elements

Facts

Application

18/689,761Filed 6 Sep 2022

Priority

7 Sep 2021

Published

28 Nov 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

A61K 31/4365
Ortho- or peri-condensed with heterocyclic ring systems: the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
A61P 25/16
For treating abnormal movements, e.g. chorea, dyskinesia: anti-Parkinson drugs
A61K 31/444
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
A61K 31/497
Non-condensed pyrazines: containing further heterocyclic rings