US 12,065,427 B2
Heterocyclic compounds capable of activating STING
Sebastian Carotta, Vienna (AT); Georg Dahmann, Biberach (DE); Cédrickx Godbout, Attenweiler (DE); Sandra Ruth Handschuh, Biberach an der Riss (DE); Herbert Nar, Ochsenhausen (DE); Thorsten Oost, Biberach an der Riss (DE); Ulrich Reiser, Vienna (AT); and Matthias Treu, Vienna (AT)
Assigned to Boehringer Ingelheim International GmbH, Ingelheim am Rhein (DE)
Filed by BOEHRINGER INGELHEIM INTERNATIONAL GMBH, Ingelheim am Rhein (DE)
Filed on Apr. 27, 2022, as Appl. No. 17/730,395.
Claims priority of application No. 21171155 (EP), filed on Apr. 29, 2021.
Prior Publication US 2022/0388986 A1, Dec. 8, 2022
Int. Cl. C07D 401/14 (2006.01); A61K 45/06 (2006.01)
CPC C07D 401/14 (2013.01) [A61K 45/06 (2013.01)] 40 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
Wherein
A is N or C,
B is a group selected from among the group consisting of
a 5-7-membered monocyclic heterocyclyl containing 1 or 2 N-atoms,
a 6-membered bicyclic heterocyclyl containing 1 N-atom,
a 7-11 membered bicyclic heterocyclyl containing 2 N-atoms,
a 7-membered bicyclic heterocyclyl containing 1 N-atom and 1 O-atom,
a 6-membered monocyclic heterocyclyl containing 1 N-atom and 1 heteroatom selected from the group consisting of O and S,
a 9-membered bicyclic heterocyclyl containing 3 heteroatoms, 2 of which are N and the other is O,
a 9-membered bicyclic heterocyclyl containing 1 N-atom and 1 S-atom,
a 10-membered bicyclic heterocyclyl containing 3 N-atoms, 2 of which are substituted with C1-6-alkyl,
phenyl,
a 9-membered bicyclic heteroaryl containing 3 N-atoms,
—C1-4-alkylene-pyrimidine, and
—C1-4-alkylene-O—C1-3-alkyl;
D is a group selected from among the group consisting of
a 9-membered bicyclic heteroaryl containing 2 N-atoms,
a 10-membered bicyclic heteroaryl containing 1 N-atom, and benzodioxole;
R1 is selected from among the group consisting of —H, —C1-6-alkyl, —CF3, —C2-6-alkynyl, —O—C1-6-alkyl and halogen;
R2 is selected from among the group consisting of —H, —C1-6-alkyl, —C1-6-alkylene-OH, —C(O)OH, —C(O)O—C1-6-alkyl and -pyrazolyl-C1-6-alkyl;
R3 is —H or —C1-6-alkyl;
R4 is selected from among the group consisting of —H, —C1-3-alkyl, —NH2, —NHC1-3-alkyl and N(C1-3-alkyl)2;
R5 is absent or is selected from among the group consisting of —H, —C1-6-alkyl, —S(O2)—C1-6-alkyl, —NH—S(O2)—C1-6-alkyl, ═O, —C(O)—C1-6-alkyl, —C(O)H, —C(O)OH, —C(O)NH2, —C(O)O—C1-6-alkyl, —NR5.1R5.2, —C1-6-alkylene-C(O)OH, —S(O2)—NH2, -pyrolidin-2-one-1-yl, -tetrazolyl, and a 5-membered heteroaryl with 1 or 2 heteroatoms selected from the group consisting of N and O, substituted with R5.3;
R5.1 is selected from among the group consisting of —H, —C1-6-alkyl, —C(O)—C1-6-alkyl and —C1-6-alkylene-O—C1-6-alkyl;
R5.2 is selected from among the group consisting of —H, —C1-6-alkyl, —C(O)—C1-6-alkyl, —C1-6-alkylene-O—C1-6-alkyl and —C1-6-alkylene-R5.3;
R5.3 is selected from among the group consisting of —H, —C1-6-alkyl and a 6-membered heteroaryl with 1 or 2 heteroatoms selected from a group consisting of N and O;
R6 is absent or is selected from among the group consisting of —H, —C1-6-alkyl, ═O and —C(O)OH;
or a salt thereof.