# US 10,307,402 B2 · Azabenzimidazole derivatives as agonists of the AMP-activated protein kinase

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- Number: US 10,307,402 B2
- Document ID: US10307402B2
- Status: Granted
- Kind: B2
- Application number: 15/543,244
- Filed: 2016-01-13
- Published: 2018-02-01
- Granted: 2019-06-04
- Earliest claimed: 2015-01-16
- Assignees: Boehringer Ingelheim International GmbH
- Applicants: Boehringer Ingelheim International GmbH
- Inventors: Dirk Gottschling; Joerg P. Hehn; Christoph Hoenke; Elke Langkopf
- Web page: https://patentgrep.com/patent/US10307402B2

## CPC

- A61K 31/4188: condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
- A61K 31/34: having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/06: Antihyperlipidemics
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/12: Antihypertensives
- A61P 13/12: of the kidneys
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 493/04: Ortho-condensed systems
- C12N 9/12: transferring phosphorus containing groups, e.g. kinases (2.7)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)

## 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.

## Claims

### Claim 1

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.

### Claim 2 (depends on 1)

A pharmaceutically acceptable salt of a compound according to claim 1.

### Claim 3 (depends on 1)

A pharmaceutical composition comprising one or more compounds according to claim 1 or one or more pharmaceutically acceptable salts thereof, optionally together with one or more inert carriers and/or diluents.