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US 10,307,402 B2Granted
Azabenzimidazole derivatives as agonists of the AMP-activated protein kinase
AssigneeBoehringer Ingelheim International GmbH
InventorsDirk Gottschling, Joerg P. Hehn, Christoph Hoenke, Elke Langkopf
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Abstract
The present invention relates to compounds of general formula I, wherein the group R1, X and Y are defined as in claim 1, which have valuable pharmacological properties, in particular bind to the AMP-activated protein kinase (AMPK) and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.
Claims3
A compound of formula
- wherein
- R1 is selected from the group consisting of F and Cl;
- X is selected from the group consisting of a divalent straight-chained or branched —C1-3-alkyl-O— linker attached via the O-atom to the imidazopyridine core and
- a trivalent linker selected from
- attached via the O-atom to the imidazopyridine core and attached via the remaining two binding positions to vicinal carbon atoms of group Y;
- and
- Y is phenyl,
- optionally substituted with 1 to 2 groups independently selected from F, Cl, NC—, H3C—, F3C—, and H3C—O—,
- but mandatorily substituted with a group selected from RSRS′(O═)S═N—, RSRS′(O═)S═N—C1-3-alkyl-, RSRS′(O═)S═N—C(═O)—, (RN)N═S(═O)(RS)—, (RN)N═S(═O)(RS)—CH2—, RSRS′(RN′—N═)S═N—C(═O)—, RSRS′(O═)S═N—C(═O)—C1-3-alkyl-, RSRS′(O═)S═N—C(═O)—C2-3-alkenyl-, and RSRS′(RN′—N═)S═N—,
- wherein RN is selected from H, NC— and C1-4-alkyl, and RN′ is selected from H and NC—,
- wherein RS is selected from H3C—, H5C2— and cyclopropyl, and RS′ is independently selected from C1-4-alkyl- and C3-6-cycloalkyl, from an aryl group selected from phenyl and benzyl, and from the heteroaryl group pyridinyl,
- wherein any alkyl and cycloalkyl group mentioned hereinbefore under RN, RS and RS′ is optionally substituted with F, (C1-3-alkyl)2N—, (C1-3-alkyl)HN—, H2N—, NC—, HO—, H3C—, and H3C—O—,
- wherein any aryl and heteroaryl group mentioned hereinbefore under RS′ is optionally substituted with 1 to 3 groups independently selected from halogen, NC—, HO—, C1-3-alkyl, and C1-3-alkyl-O—,
- wherein in any definition mentioned hereinbefore and if not specified otherwise, any alkyl group or sub-group may be straight-chained or branched,
- or a salt thereof.
12 more elements
Dependencies are inferred from the claim text.