US 12,433,897 B2
Pyridine derivatives with n-linked cyclic substituents as cGAS inhibitors
Annekatrin Charlotte Heimann, Biberach an der Riss (DE); Sandra Ruth Handschuh, Biberach an der Riss (DE); Christoph Hoenke, Biberach an der Riss (DE); Cédrickx Godbout, Attenweiler (DE); Christian Gnamm, Biberach an der Riss (DE); Patrick Gross, Biberach (DE); Joerg Kley, Mittelbiberach (DE); Christian Andreas Kuttruff, Schemmerhofen (DE); Dirk Reinert, Bad Duerkheim (DE); Raphael Stuber, Schwendi (DE); Marc Alexander Grundl, Biberach an der Riss (DE); and Theodor Theis, Biberach an der Riss (DE)
Assigned to Boehringer Ingelheim International GmbH, Ingelheim am Rhein (DE)
Filed by BOEHRINGER INGELHEIM INTERNATIONAL GMBH, Ingelheim am Rhein (DE)
Filed on May 10, 2022, as Appl. No. 17/741,009.
Claims priority of application No. 21173689 (EP), filed on May 12, 2021.
Prior Publication US 2023/0000878 A1, Jan. 5, 2023
Int. Cl. A61K 31/5386 (2006.01); A61K 31/4412 (2006.01); A61K 31/496 (2006.01); A61K 31/519 (2006.01); A61K 31/5377 (2006.01); A61K 39/395 (2006.01); A61K 45/06 (2006.01); A61P 37/06 (2006.01); C07D 491/048 (2006.01); C07D 519/00 (2006.01)
CPC A61K 31/5386 (2013.01) [A61K 31/4412 (2013.01); A61K 31/496 (2013.01); A61K 31/519 (2013.01); A61K 31/5377 (2013.01); A61K 39/3955 (2013.01); A61K 45/06 (2013.01); A61P 37/06 (2018.01); C07D 491/048 (2013.01); C07D 519/00 (2013.01)] 65 Claims
 
1. A compound of formula (I),

OG Complex Work Unit Chemistry
wherein
R1 is selected from methyl, ethyl, halomethyl, haloethyl and halogen, wherein
G is selected from O, NR8, CH2, and CR8R9,
wherein
R2 is selected from H, halogen, cyclopropyl, C1-3-alkyl, —C2-5-alkynyl, —S-methyl and CN,
wherein
R3 is H or methyl,
R4 is H or methyl,
R5 is selected from H, methyl, —CN, -methylene-OH and —CF3,
or R5 may be absent,
R6 is selected from H, methyl, —CN, -methylene-OH and —CF3,
or R5 and R6 together with the C-atoms in between form a ring selected from oxetane, tetrahydrofurane and cyclopropane,
R7 is selected from H, halogen, (C1-3)-alkyl and halo-(C1-3)-alkyl,
R8 is selected from CN, H and methyl,
R9 is selected from H, methyl and halogen
or R9 may be absent,
or G is CR8R9, R5 and R9 are absent, and R8 and R6 and the two C-atoms in between R8 and R6 form an annulated five-membered aromatic or non-aromatic heterocycle comprising one, two or three heteroatoms each independently selected from N, S and O,
or G is CR8R9 and R8 and R9 form together with the C-atom in between R8 and R9 a diazirine ring;
or a pharmaceutically acceptable salt thereof.