# US 7,745,491 B2 · Substituted phenylacetamides and their use as glucokinase activators

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- Number: US 7,745,491 B2
- Document ID: US7745491B2
- Status: Granted
- Kind: B2
- Application number: 11/573,464
- Filed: 2005-08-09
- Published: 2009-02-26
- Granted: 2010-06-29
- Earliest claimed: 2004-08-12
- Assignees: Prosidion Limited
- Inventors: Matthew Colin Thor Fyfe; Vilasben Kanji Shah
- Web page: https://patentgrep.com/patent/US7745491B2

## CPC

- C07C 317/44: having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- 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 237/20: Nitrogen atoms (nitro radicals C07D237/12)
- C07D 241/20: Nitrogen atoms (nitro radicals C07D241/16)
- C07C 2601/02: with a three-membered ring
- C07C 2601/08: the ring being saturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds of Formula (I) wherein R1 is a cycloalkylsulphonyl group, or pharmaceutically acceptable salts thereof, are useful in the prophylactic and therapeutic treatment of hyperglycemia and diabetes.

## Claims

### Claim 1

A compound of Formula (I):
or a pharmaceutically acceptable salt thereof, wherein:
V is (CH2)k; where one CH2 group is replaced by CH(OH) or C═O;
R1 is SO2R4;
T together with the —N═C— represents pyrazolyl, pyrazinyl or pyridazinyl;
R2 and R3 each independently are hydrogen, halogen, OCFnH3-n, methoxy, CO2R5, cyano, nitro, CHO, CONR6R7, CON(OCH3)CH3, or C1-2alkyl;
R4 is a C3-7cycloalkyl group;
R5 is hydrogen, or a C1-4alkyl group;
R6 and R7 each independently are hydrogen or a C1-4alkyl group;
n is 1, 2 or 3;
k is 4 or 5;
m is 0 or 1; and
the dotted line together with the solid line forms an optional double bond, and Δ indicates that the double bond has the (E)-configuration.

### Claim 2 (depends on 1)

A compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein the dotted line together with the solid line forms a single bond.

### Claim 3 (depends on 2)

A compound according to claim 2, or a pharmaceutically acceptable salt thereof, wherein the dotted line together with the solid line forms a single bond, and the absolute configuration at the asymmetric centre a to the amide carbonyl carbon is (R).

### Claim 4 (depends on 1)

A compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein m is 0.

### Claim 5 (depends on 1)

A compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein the group formed by
is 3-oxocyclopentyl, 4-oxocyclohexyl or 3-hydroxycyclopentyl.

### Claim 6 (depends on 5)

A compound according to claim 5, or a pharmaceutically acceptable salt thereof, wherein the group formed by
is 3-oxocyclopentyl.

### Claim 7 (depends on 1)

A compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R4 is C3-4cycloalkyl.

### Claim 8 (depends on 1)

A compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 and R3 are independently selected from hydrogen, halogen and methyl.

### Claim 9 (depends on 1)

A compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein the ring formed by T together with the —N═C— to which it is attached is selected from 1-methylpyrazol-3-yl, pyrazin-2-yl and 6-methylpyridazin-3-yl.

### Claim 10 (depends on 1)

A compound according to claim 1 selected from:
2(R)-2-(4-cyclopropanesulfonylphenyl)-N-(1-methylpyrazol-3-yl)-3-((R)-3-oxocyclopentyl)propionamide;
2(R)-2-(4-cyclopropanesulfonylphenyl)-N-(pyrazin-2-yl)-3-((R)-3-oxocyclopentyl)propionamide; and
2(R)-2-(4-cyclopropanesulfonylphenyl)-N-(6-methylpyridazin-3-yl)-3((R)-3-oxocyclopentyl)propionamide;
or a pharmaceutically acceptable salt of any one thereof.

### Claim 11 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

### Claim 12 (depends on 1)

A process for the preparation of a compound of Formula (I):
or a pharmaceutically acceptable salt thereof, said process comprising the condensation of a compound of the formula immediately below:
with a compound of Formula (V):
or a salt thereof,
wherein the dotted line together with solid line forms an optional double bond, and V, T, R1, R2, R3, m and Δ are as defined in claim 1.

### Claim 13 (depends on 8)

A compound according to claim 8, or a pharmaceutically acceptable salt thereof, wherein the ring formed by T together with the —N═C— to which it is attached is selected from 1-methylpyrazol-3-yl, pyrazin-2-yl and 6-methylpyridazin-3-yl.

### Claim 14 (depends on 1)

A compound of a formula illustrated below:
or a salt thereof, wherein V, R1, and m are as defined in claim 1, the dotted line together with the solid line forms an optional double bond, and Δ indicates that the double bond has the (E) configuration.

### Claim 15 (depends on 14)

A compound according to claim 14 wherein the dotted line together with the solid line forms a double bond.

### Claim 16 (depends on 14)

A compound according to claim 14 wherein the dotted line together with the solid line forms a single bond.

### Claim 17 (depends on 12)

The process according to claim 12 wherein the dotted line together with the solid line forms a double bond.

### Claim 18 (depends on 12)

The process according to claim 12 wherein the dotted line together with the solid line forms a single bond.