# US 9,150,523 B2 · Piperazine derivatives, methods for preparing same, and uses thereof in the treatment of insulin resistance

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- Number: US 9,150,523 B2
- Document ID: US9150523B2
- Status: Granted
- Kind: B2
- Application number: 14/128,381
- Filed: 2012-06-22
- Published: 2014-06-05
- Granted: 2015-10-06
- Earliest claimed: 2011-06-23
- Assignees: Metabolys
- Applicants: Gerard Moinet; Gabriel Baverel; Remi Nazaret; Bernard Ferrier
- Inventors: Gerard Moinet; Gabriel Baverel; Remi Nazaret; Bernard Ferrier
- Web page: https://patentgrep.com/patent/US9150523B2

## CPC

- C07D 241/20: Nitrogen atoms (nitro radicals C07D241/16)
- A61K 31/495: having six-membered rings with two {or more} nitrogen atoms as the only ring heteroatoms, e.g. piperazine {or tetrazines}(A61K31/48 takes precedence {; with three nitrogen atoms A61K31/53})
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61K 31/497: containing further heterocyclic rings
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- C07D 213/74: Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C07D 295/088: to an acyclic saturated chain
- C07D 295/096: with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

Disclosed herein are compounds and compositions useful in the treatment of pathologies associated with the insulin resistance syndrome (or syndrome X), in particular in the treatment of type 2 diabetes.

## Claims

### Claim 1

A compound of formula (I),
in which:
R1 is —(CH2)4C(O)OH; and;
R2 represents:
a phenyl, non-substituted or substituted by one or more substituents, identical or different, chosen from:
a C1 to C6 alkoxy group, linear or branched;
a halogen atom; or
a C1 to C5 alkyl group, linear or branched, substituted by one or more halogen atoms;
a monocyclic or polycyclic heteroaryl chosen from

### Claim 2 (depends on 1)

A method for preparing a compound according to claim 1, comprising:
(a) the protection of the acid function of a compound of formula (II)
in which R1 is as defined by claim 1;
(b) the reaction of the compound obtained at in step (a) with a compound of formula R4—(CH2)2—R5 in which R4 and R5, identical or different, represent a leaving group;
(c) the reaction of the compound obtained in step (b) with a compound of formula (III)
in which R2 as defined by claim 1; and
(d) deprotection of the compound obtained in step (c).

### Claim 3 (depends on 1)

A method for preparing a compound according to claim 1, comprising:
(i) the reaction of a compound of formula (III)
in which R2 is as defined by claim 1 with a compound of formula R4—(CH2)2—R5, in which R4 and R5, identical or different, represent a leaving group;
(ii) the protection of the acid function of a compound of formula (II)
in which R1 is as defined by claim 1;
(iii) the reaction between the compound obtained in step (i) and the compound obtained at step (ii); and
(iv) deprotection of the compound obtained in step (iii).

### Claim 4 (depends on 1)

A method for treating type 2 diabetes in a patient in need thereof, the method comprising administering an effective quantity of a compound according to claim 1.

### Claim 5 (depends on 1)

A pharmaceutical composition comprising, as active principle, at least one compound according to claim 1.

### Claim 6 (depends on 5)

A pharmaceutical composition according to claim 5, further comprising at least one other anti-diabetic agent.