Triazolopyridin-3-ones or their salts and pharmaceutical compositions comprising the same

A method for treating diabetic kidney disease in a subject in need thereof, the method comprising administering to the subject a therapeutically effective amount of a compound of Formula X

• or a stereoisomer thereof or a pharmaceutically acceptable salt thereof;
• wherein
• R1 is hydrogen or fluoro;
• and
• R2 and R3, each independently, are selected from the group consisting of hydrogen, halogen, C1-6 alkyl, —R, and —C≡C—R;
• wherein said R is substituted or unsubstituted cyclic ring, optionally containing 1 to 5 heteroatom ring members chosen from O, N, or S, and the cyclic ring is aromatic or non-aromatic.

A method for treating diabetic kidney disease in a subject in need thereof, the method comprising administering to the subject a therapeutically effective amount of a compound selected from the group consisting of:

• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-bromo[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• N-[4-[2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-3-oxo-2,3-dihydro[1,2,4]triazolo[4,3-a]pyridin-6-yl]phenyl]acetamide;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-[4-(methylsulfonyl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-[4-(morpholin-4-ylsulfonyl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-[4-(1H-1,2,4-triazol-3-yl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-[3-(1H-1,2,4-triazol-3-yl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-[4-(1,2-oxazol-3-yl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• N-[4-[2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-3-oxo-2,3-dihydro[1,2,4]triazolo[4,3-a]pyridin-6-yl]pyridin-2-yl]acetamide;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-[6-(trifluoromethyl)pyridin-3-yl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-[6-(morpholin-4-yl)pyridin-3-yl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-[6-(morpholin-4-yl)pyridin-3-yl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-(1,3-benzodioxol-5-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-(2,3-dihydro-1,4-benzodioxin-6-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 6-(2-amino-1,3-benzothiazol-5-yl)-2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• N-[5-[2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-3-oxo-2,3-dihydro[1,2,4]triazolo[4,3-a]pyridin-6-yl]-1,3-benzothiazol-2-yl]acetamide;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-6-(2,1,3-benzoxadiazol-5-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 6-[2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-3-oxo-2,3-dihydro[1,2,4]triazolo[4,3-a]pyridin-6-yl]-8-methyl-3,4-dihydroquinolin-2(1H)-one;
• N-[4-[2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-3-oxo-2,3-dihydro[1,2,4]triazolo[4,3-a]pyridin-5-yl]phenyl]acetamide;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-5-[4-(1,2-oxazol-3-yl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-5-(1,3-benzodioxol-5-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-5-(2,1,3-benzoxadiazol-5-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[3-(methylsulfonyl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-2-[(dimethylamino)methyl]phenyl[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[4-(morpholin-4-ylcarbonyl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[4-(1,2-oxazol-3-yl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[3-(1H-pyrazol-3-yl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[4-(1,2,5-oxadiazol-3-yl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)phenyl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[6-(trifluoromethyl)pyridin-3-yl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-(6-methoxypyridin-3-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[6-(dimethylamino)pyridin-3-yl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-[6-(morpholin-4-yl)pyridin-3-yl][1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-(1,2,3,6-tetrahydropyridin-4-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-(1H-pyrrolo[2,3-b]pyridin-3-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-(1,3-benzodioxol-5-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-(1H-indazol-6-yl)[1,2,4]triazolo[4,a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-(2,1,3-benzoxadiazol-5-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-(1H-benzotriazol-6-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-(1H-pyrrolo[2,3-b]pyridin-4-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 7-[2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-3-oxo-2,3-dihydro[1,2,4]triazolo[4,3-a]pyridin-7-yl]-1,4-dihydro-2H-3,1-benzoxazin-2-one;
• 6-[2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-3-oxo-2,3-dihydro[1,2,4]triazolo[4,3-a]pyridin-7-yl]-2H-1,4-benzoxazine-3 (4H)-one;
• 6-[2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-3-oxo-2,3-dihydro[1,2,4]triazolo[4,3-a]pyridin-7-yl]-8-methyl-3,4-dihydroquinolin-2(1H)-one;
• 2-[(2E)-2-(aminomethyl)-3-fluoroprop-2-en-1-yl]-7-(4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-5-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-(4-methylsulfonylphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-(4-piperazin-1-ylphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-[6-(trifluoromethyl)-3-pyridyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-[6-(dimethylamino)-3-pyridyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-(1,3-benzodioxol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 6-[2-[2-(aminomethyl)-3,3-difluoro-allyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-8-methyl-3,4-dihydro-1H-quinolin-2-one;
• 6-[2-[2-(aminomethyl)-3,3-difluoro-allyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-1-methyl-3,4-dihydroquinolin-2-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-(1-ethylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-[2-(1-methylpyrazol-4-yl)ethynyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-[2-[6-(dimethylamino)-3-pyridyl]ethynyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-[2-(6-morpholino-3-pyridyl)ethynyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-[2-(3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethynyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-[2-(2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)ethynyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)ethynyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• 6-[2-[2-[2-(aminomethyl)-3,3-difluoro-allyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-7-yl]ethynyl]-3,4-dihydro-1H-quinolin-2-one;
• and
• 2-[2-(aminomethyl)-3,3-difluoro-allyl]-7-[2-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)ethynyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one;
• or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof.