US 12,071,403 B2
Modulators of complex I
Kai Gerlach, Mittelbiberach (DE); Christian Eickmeier, Mittelbiberach (DE); Jan Magnus Kriegl, Ulm (DE); Lothar Kussmaul, Schemmerhofen (DE); Klaus Rudolf, Warthausen (DE); and Bernhard Schmid, Ingoldingen (DE)
Assigned to Boehringer Ingelheim International GmbH, Ingelheim am Rhein (DE)
Filed by Boehringer Ingelheim International GmbH, Ingelheim am Rhein (DE)
Filed on Sep. 7, 2023, as Appl. No. 18/462,578.
Application 18/462,578 is a division of application No. 17/002,937, filed on Aug. 26, 2020, granted, now 11,795,147.
Claims priority of application No. 19193570 (EP), filed on Aug. 26, 2019.
Prior Publication US 2024/0150285 A1, May 9, 2024
Int. Cl. C07D 207/38 (2006.01); C07D 403/04 (2006.01); C07D 471/08 (2006.01); C07D 491/044 (2006.01); C07D 498/10 (2006.01)
CPC C07D 207/38 (2013.01) [C07D 403/04 (2013.01); C07D 471/08 (2013.01); C07D 491/044 (2013.01); C07D 498/10 (2013.01)] 21 Claims
 
1. A method of treating a disease involving retinal dysfunction in a patient comprising administering to said patient a therapeutically effective amount of a compound having formula (I) or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein:
R1 is C1-4-alkyl unsubstituted or substituted with MeO; tetrahydropyranyl, tetrahydrofuranyl, oxetanyl, dioxepanyl, pyrrolidinyl or piperidinyl; or
pyrrolidinyl or piperidinyl with the nitrogen substituted by methyl, isopropyl, oxetanyl, ethoxycarbonyl, acetyl, or trifluoroacetyl;
R2 is a 5-, 6- or 7-membered ring containing 1 or 2 heteroatoms selected from O or N bound in formula (I) by a C═C double bond,
in which one or both N-atoms can be substituted by methyl, isopropyl, acetyl, benzyloxycarbonyl, phenyl, oxetanyl or tetrahydropyranyl, and
in which one or more C-atoms can be substituted by -methyl or —OH;
R3 and R4 are independently from one another
hydrogen; C1-6-alkyl, unsubstituted or substituted with one or more F, methoxy, C3-8-cycloalkyl unsubstituted or substituted with one or more F; aryl; heteroaryl consisting of 5 to 6 ring atoms; or heterocyclyl selected from the group consisting of oxetanyl, tetrahydropyranyl and pyrrolidinyl, said heterocyclyl being unsubstituted or substituted with C1-6-alkyl, acetyl, tetrahydrofuranyl, oxetanyl or hydroxyethylacetyl;
or R3 and R4 together with the attached N form a heterocyclyl ring selected from the group consisting of morpholinyl and pyrrolidinyl both unsubstituted or substituted with C1-6-alkyl, F, or hydroxyl;
or R3 and R4 together represent one of the following groups:

OG Complex Work Unit Chemistry