US 12,344,606 B2
Next-generation modulators of stimulator of interferon genes (STING)
Magdalena Izabela Zawadzka, Gdansk (PL); Luigi Piero Stasi, Cracow (PL); Maciej Krzysztof Rogacki, Cracow (PL); Grzegorz Wojciech Cwiertnia, Kamesznica (PL); Lukasz Piotr Dudek, Cracow (PL); Monika Patrycja Dobrzanska, Wroclaw (PL); Grzegorz Witold Topolnicki, Piekary Slaskie (PL); Agnieszka Justyna Gibas, Cracow (PL); Anna Rajda, Gliwice (PL); Sylwia Sudol, Cracow (PL); Karolina Maria Gluza, Wroclaw (PL); and Charles-Henry Fabritius, Poznan (PL)
Assigned to Ryvu Therapeutics S.A., Cracow (PL)
Appl. No. 17/618,007
Filed by RYVU THERAPEUTICS S.A., Cracow (PL)
PCT Filed Jun. 12, 2020, PCT No. PCT/EP2020/066370
§ 371(c)(1), (2) Date Dec. 10, 2021,
PCT Pub. No. WO2020/249773, PCT Pub. Date Dec. 17, 2020.
Claims priority of application No. 19460034 (EP), filed on Jun. 12, 2019; and application No. 19460067 (EP), filed on Dec. 11, 2019.
Prior Publication US 2022/0251082 A1, Aug. 11, 2022
Int. Cl. C07D 471/04 (2006.01); A61P 35/00 (2006.01); C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01)
CPC C07D 471/04 (2013.01) [A61P 35/00 (2018.01); C07D 401/14 (2013.01); C07D 405/14 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01)] 11 Claims
 
1. A compound which is
3-({[(2-methoxypyridin-4-yl)methyl][(3S)-1-(pyridin-3-yl) piperidin-3-yl]amino}methyl)-1-methyl-1,4-dihydroquinolin-4-one,
1-methyl-3-({[(2-methylpyridin-4-yl)methyl][1-(pyridin-3-yl) piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
1-methyl-3-({[(2-methylpyridin-4-yl)methyl][(3S)-1-(pyridin-3-yl) piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
3-({[(2-methoxypyridin-4-yl)methyl][(3S)-1-(pyridin-3-yl) piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
1-methyl-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydroquinolin-4-one,
1-cyclopropyl-6,7-difluoro-3-({[(2-methoxypyridin-4-yl)methyl][(3S)-1-(pyridin-3, yl) piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
7-bromo-1-methyl-3-({[(2-methylpyridin-4-yl)methyl][(3S)-1-(pyridin-3-yl) piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
7-chloro-6-fluoro-1-methyl-3-({[(2-methylpyridin-4-yl)methyl][(3S)-1-(pyridin-3-yl) piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
3-({[(3S,5S)-5-fluoro-1-(pyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1-methyl-1,4-dihydroquinolin-4-one,
7-chloro-1-cyclopropyl-6-fluoro-3-({[(2-methoxypyridin-4-yl)methyl][(3S)-1-(pyridin-3-yl) piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
1-cyclopropyl-6,7-difluoro-3-({[(2-methoxypyridin-4-yl)methyl][(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
7-chloro-1-cyclopropyl-6-fluoro-3-({(2-methylpyridin-4-yl)methyl][(3S)-1-(pyridin-3-yl)piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
3-({[(2-methylpyridin-4-yl)methyl][(3S)-1-(pyridin-3-yl) piperidin-3-yl]amino}methyl)-1,4-dihydroquinolin-4-one,
7-bromo-1-methyl-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydroquinolin-4-one,
1-methyl-3-({[(3S)-1-(pyridin-3-yl) piperidin-3-yl][(pyridin-4-yl)methyl]amino}methyl)-1,4-dihydroquinolin-4-one,
7-chloro-1-cyclopropyl-6-fluoro-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydroquinolin-4-one,
7-chloro-1-cyclopropyl-6-fluoro-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydro-1,8-naphthyridin-4-one,
1-cyclopropyl-6-fluoro-7-methoxy-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydro-1,8-naphthyridin-4-one,
1-cyclopropyl-6-fluoro-7-methoxy-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydroquinolin-4-one,
3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1-(oxetan-3-yl)-1,4-dihydroquinolin-4-one,
7-chloro-1-cyclopropyl-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydro-1,6-naphthyridin-4-one,
7-(cyclohex-1-en-1-yl)-1-cyclopropyl-6-fluoro-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydroquinolin-4-one,
3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydroquinolin-4-one,
1-cyclopropyl-6-fluoro-7-hydroxy-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydroquinolin-4-one,
8-bromo-1-methyl-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1,4-dihydroquinolin-4-one,
7-chloro-6-fluoro-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1-(propan-2-yl)-1,4-dihydro-1,8-naphthyridin-4-one,
6-fluoro-7-methoxy-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-1-(propan-2-yl)-1,4-dihydro-1,8-naphthyridin-4-one, or
1-cyclopropyl-3-({[(3S)-1-(6-methylpyridin-3-yl) piperidin-3-yl][(2-methylpyridin-4-yl)methyl]amino}methyl)-7-(morpholin-3-yl)-1,4-dihydroquinolin-4-one;
or a salt, stereoisomer, or N-oxide thereof.