Lipopeptide compound and treatment of pain disorder

Patent metadata

Field	Value
Publication number	US-2025332129-A1
Application number	US-202318855427-A
Country	US
Kind code	A1
Filing date	Apr 14, 2023
Priority date	Apr 15, 2022
Publication date	Oct 30, 2025
Grant date	—

Abstract

The invention is based on the discovery of a novel compound with analgesic properties which could be used as a new tool for the treatment of pain disorders such as visceral pain. Thus, the invention relates to novel lipopeptide compound, derived from gamma-aminobutyric acid. The invention also relates to a lipopeptide compound according to the invention for the treatment of treating pain disorder, such as somatic pain and visceral pain.

First claim

1 . A compound of Formula (I):

wherein
R is a C5-C19 linear or branched hydrocarbon chain selected from the group consisting of alkyl, alkene, and alkyne,
Xaa is leucine, phenylalanine, isoleucine or alanine,
Xbb is HNCH 2 CH 2 CH 2 CO,
Y is —OH or NH 2 ,

and wherein Xbb is linked to Xaa through its amine functional group and wherein the RC(O) group is at the N terminal side and Y is a C terminal side,
or a pharmaceutical acceptable salt thereof.

2 . The compound according to claim 1 , wherein R is a C5-C19 alkyl.

3 . The compound according to any of claim 1 , wherein R is a C12 alkyl or a C14 alkyl or a C16 alkyl.

4 . The compound according to claim 1 , wherein Y is —OH—.

5 . The compound according to claim 1 , wherein the compound is C15 C(O)-Phe-gamma-aminobutyric acid.

6 . The compound according to claim 1 , wherein the compound is C11 C(O)-Ile-gamma-aminobutyric acid.

7 . The compound according to claim 1 , wherein the compound is C13 C(O)-Ile-gamma-aminobutyric acid.

8 . The compound according to claim 1 , wherein the compound is C11 C(O)-Ala-gamma-aminobutyric acid.

9 . The compound according to claim 1 , wherein the compound is C15 C(O)-Leu-gamma-aminobutyric acid.

10 . A method for treating a subject in need thereof, the method comprising administering to the subject a compound according to claim 1 , wherein the compound is used as a drug.

11 . A method for treating a pain disorder in a subject in need thereof, the method comprising administering to the subject a therapeutically effective amount of a compound according to claim 1 .

12 . (canceled)

13 . (canceled)

14 . A pharmaceutical composition, comprising a compound according to claim 1 , and one or more pharmaceutically acceptable excipients.

15 . A method to obtain the compound according to claim 1 , comprising synthesizing the compound using a peptide solid phase synthesis technique or a liquid phase synthesis technique.

16 . The method according to claim 11 , wherein the pain disorder is a visceral pain disorder or a somatic pain disorder.

17 . The method according to claim 16 , wherein the visceral pain disorder is Irritable Bowel Syndrome (IBS) or Inflammatory Bowel Disease (IBD).

18 . The compound for use according to claim 16 , wherein the visceral pain disorder is resulting from a urogenital disorder selected from the group consisting of a bladder neoplasm, a chronic urinary tract infection, interstitial cystitis, radiation cystitis, recurrent cystitis, recurrent urethritis, urolithiasis, uninhibited bladder contractions, urethral diverticulum, chronic urethral syndrome, a urethral carbuncle and a urethral stricture.

Assignees

• Inst Nat Sante Rech Med
• Univ Toulouse Iii – Paul Sabatier
• Centre Nat Rech Scient
• Ct Hospitalier Universitaire Toulouse
• Institut National De Rech Pour Lagriculture Lalimentation Et Lenvironnement
• Ecole Nat Veterinaire De Toulouse
• Enscm
• Univ Montpellier

Inventors

• Cenac Nicolas
• Bertrand-Michel Justine
• Durand Thierry
• Galano Jean-Marie
• Hueber Amandine
• Le Faouder Pauline
• Guy Alexandre
• Maurel Sarah

Classifications

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• C07C237/22

  having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated (peptides C07K) · CPC title

• A61K31/197 Primary

  the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid (carnitine A61K31/205) · CPC title