# US 9,518,016 B2 · Insulin secretion promoting agents

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- Number: US 9,518,016 B2
- Document ID: US9518016B2
- Status: Granted
- Kind: B2
- Application number: 15/160,362
- Filed: 2016-05-20
- Published: 2016-09-15
- Granted: 2016-12-13
- Earliest claimed: 2011-08-03
- Assignees: Val-Chum, Limited Partnership
- Applicants: Val-Chum, Limited Partnership
- Inventors: Murthy Madiraju; Marc Prentki; Erik Joly
- Web page: https://patentgrep.com/patent/US9518016B2

## CPC

- C07D 213/40: Acylated substituent nitrogen atom
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/50: for increasing or potentiating the activity of insulin
- C07C 271/44: to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present disclosure relates to novel compounds, compositions containing same and methods for treating or preventing a condition associated with a deficient insulin secretion such as diabetes and metabolic syndrome in a subject in need thereof.

## Claims

### Claim 1

A compound of formula I
or a pharmaceutically acceptable salt or solvate thereof, wherein
X is N or CH;
R1 is lower linear or branched alkyl, cycloalkyl, lower linear or branched alkenyl, cycloalkenyl or aryl;
each of R2, R3, R4 and R5 is H or one or more independently selected substituent;
R6 is H, lower linear or branched alkyl, or cycloalkyl;
each of R7 and R8 is independently selected from H, lower alkyl or fluoride;
provided that said compound is other than compounds i), ii) iii) and iv)):

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 is C1-6 linear or C3-6 branched alkyl, C3-6 cycloalkyl, or optionally substituted phenyl.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R6 is H, C1-6 linear alkyl or C3-6 branched alkyl, C3-6 cycloalkyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R2, R3, R4 and R5 are H or an independently selected substituent.

### Claim 5 (depends on 1)

The compound of claim 1, wherein each of R7 and R8 is independently selected from H or C1-3 alkyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R2, R3, R4, R5, R7 and R8, are each H.

### Claim 7 (depends on 1)

The compound as defined in claim 1, wherein said compound is a compound wherein X is CH, R1 is C1-3 linear alkyl, C3 branched alkyl, or optionally substituted phenyl and R6 is H, C1-3 linear alkyl, C3 branched alkyl or C3 cycloalkyl.

### Claim 8 (depends on 1)

The compound as defined in claim 1, wherein said compound is a compound wherein X is N, R1 is C1-3 linear alkyl, C3 branched alkyl, or optionally substituted phenyl and R6 is H, C1-3 linear alkyl, C3 branched alkyl or C3 cycloalkyl.

### Claim 9 (depends on 1)

The compound as defined in claim 1, wherein said compound is a compound of formula II
wherein X is N, R1 is C1-3 linear alkyl, C3 branched alkyl, or optionally substituted phenyl and R6 is H, C1-3 linear alkyl, C3 branched alkyl or C3 cycloalkyl.

### Claim 10 (depends on 1)

The compound as defined in claim 1, wherein said compound is a compound of formula II
wherein X is CH, R1 is C1-3 linear alkyl, C3 branched alkyl, or optionally substituted phenyl and R6 is H, C1-3 linear alkyl, C3 branched alkyl or C3 cycloalkyl.

### Claim 11 (depends on 9)

The compound of claim 9, wherein R2, R3, R4 and R5 are H.

### Claim 12 (depends on 10)

The compound of claim 10, wherein R2, R3, R4 and R5 are H.

### Claim 13 (depends on 1)

The compound of claim 1, wherein the compound is
Compound #
Structure
1
3
4
5
6
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 14 (depends on 1)

A pharmaceutical composition comprising a compound as defined in claim 1, or a pharmaceutically acceptable salt or solvate thereof, and an acceptable excipient.