US 12,240,828 B2
Heteroaromatic compounds as vanin inhibitors
Cedrickx Godbout, Attenweiler (DE); Martin Thomas Fleck, Munich (DE); Hannes Fiepko Koolman, Biberach an der Riss (DE); and Thomas Martin Kirrane, Jr., San Ramon, CA (US)
Assigned to Boehringer Ingelheim International GmbH, Ingelheim am Rhein (DE)
Appl. No. 17/299,148
Filed by Boehringer Ingelheim International GmbH, Ingelheim am Rhein (DE)
PCT Filed Dec. 2, 2019, PCT No. PCT/EP2019/083259
§ 371(c)(1), (2) Date Jun. 2, 2021,
PCT Pub. No. WO2020/114947, PCT Pub. Date Jun. 11, 2020.
Claims priority of provisional application 62/774,412, filed on Dec. 3, 2018.
Prior Publication US 2022/0048889 A1, Feb. 17, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/14 (2006.01); A61K 45/06 (2006.01); C07D 401/06 (2006.01); C07D 413/14 (2006.01)
CPC C07D 401/14 (2013.01) [A61K 45/06 (2013.01); C07D 401/06 (2013.01); C07D 413/14 (2013.01)] 11 Claims
 
1. A compound of the formula I,

OG Complex Work Unit Chemistry
wherein
R1 is selected from the group consisting of
H,
phenyl substituted by both R1.1 and R1.3,
a 5-6 membered heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of S, N and O and substituted by both R1.2 and R1.5, and
a 5-6 membered heterocyclyl containing 1 or 2 heteroatoms selected from the group consisting of S, N and O and substituted by R1.4;
wherein
R1.1 is selected from the group consisting of H, —CN, Br, Cl, F, C1-4-alkyl, C3-5-cycloalkyl, 5 membered heteroaryl optionally substituted by C1-3-alkyl, CF3, F3C—CH2, HF2C—H2N—S(O)2—, H3C—NH—S(O)2—, (H3C)2N—S(O)2—, H3C—NH—CO—, C1-4-alkyl-O—, H3C—O—CO—, H2N—, (H3C)2N—, H2N—CO— and H3C—CO—NH—;
R1.2 is selected from the group consisting of H, —CN, Br, Cl, F, C1-4-alkyl, C3-5-cycloalkyl CF3, F3C—CH2, HF2C—H2N—S(O)2—, H3C—NH—S(O)2—, (H3C)2N—S(O)2—, H3C—NH—CO—, C1-4-alkyl-O—, H3C—O—CO—, H2N—, (H3C)2N—, H2N—CO— and H3C—CO—NH—;
wherein in the definition of R1.1 and R1.2 mentioned alkyl is optionally substituted by 1-3 F-atoms
R1.3 is selected from the group consisting of H, Cl, F, CN, C1-4-alkyl, and C1-4-alkyl-O—;
R1.4 is selected from the group consisting of H, —CN, Br, Cl, F and C1-4-alkyl optionally substituted by 1-3 F-atoms,
R1.5 is H or C1-4-alkyl,
R2 and R3 are independently from each other selected from the group consisting of H and C1-3-alkyl,
or
R2 and R3 together form a 3 to 6 membered carbocycle, a 4 to 6 membered heterocycle containing 1O atom or 1N atom or a 5 to 9 membered heteroaryl containing 1-2N-atoms;
R4 denotes R4.1R4.2N— or NC—;
R4.1 is selected from the group consisting of C1-4-alkyl-CO—, pyrimidinyl, and C3-4-cycloalkyl-CO— substituted by both R4.1.1 and R4.1.2,
wherein
R4.1.1 and R4.1.2 independently from each other are selected from the group consisting of H, —CH3, F, and —CN;
R4.2 denotes H or methyl;
R5 denotes H or methyl;
or a pharmaceutically acceptable salt thereof.