# US 7,745,475 B2 · Heteroaryl benzamide derivatives as GLK activators

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 7,745,475 B2
- Document ID: US7745475B2
- Status: Granted
- Kind: B2
- Application number: 11/628,448
- Filed: 2005-06-01
- Published: 2008-01-17
- Granted: 2010-06-29
- Earliest claimed: 2004-06-05
- Assignees: AstraZeneca AB
- Inventors: Craig Johnstone; Darren McKerrecher; Kurt Gordon Pike; Michael James Waring
- Web page: https://patentgrep.com/patent/US7745475B2

## CPC

- C07D 277/46: by carboxylic acids, or sulfur or nitrogen analogues thereof
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/08: for glucose homeostasis (pancreatic hormones A61P5/48)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 231/40: Acylated on said nitrogen atom
- C07D 285/08: 1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of Formula (I) wherein: R1 is hydroxymethyl; R2 is selected from —C(O)NR4R5, SO2NR4R5, S(O)pR4 and HET-2; HET-1 is a 5- or 6-membered, optionally substituted C-linked heteroaryl ring; HET-2 is a 4-, 5- or 6-membered, C- or N-linked optionally substituted heterocyclyl ring; R3 is selected from halo, fluoromethyl, difluoromethyl, trifluoromethyl, methyl, methoxy and cyano; R4 is selected from for example hydrogen, optionally substituted (1-4C)alkyl and HET-2; R5 is hydrogen or (1-4C)alkyl; or R4 and R5 together with the nitrogen atom to which they are attached may form a heterocyclyl ring system as defined by HET-3; HET-3 is for example an optionally substituted N-linked, 4, 5 or 6 membered, saturated or partially unsaturated heterocyclyl ring; p is (independently at each occurrence) 0, 1 or 2; m is 0 or 1; n is 0, 1 or 2; provided that when m is 0, then n is 1 or 2; or a salt, pro drug or solvate thereof, are described. Their use as GLK activators, pharmaceutical compositions containing them, and processes for their preparation are also described.

## Claims

### Claim 1

The compound 3-{[4-(azetidin-1-ylcarbonyl)phenyl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide or a salt thereof.

### Claim 2 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1, or a salt thereof, together with a pharmaceutically acceptable diluent or carrier.

### Claim 3 (depends on 1)

A process for the preparation of a compound of claim 1 or a salt thereof comprising reacting 3-{[4-(Azetidin-1-ylcarbonyl)-2-chlorophenyl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide with hydrogen in the presence of 10% palladium on carbon to form 3-{[4-(azetidin-1-ylcarbonyl)phenyl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide, and thereafter optionally forming a salt thereof.