Pseudomonas aeruginosa inhibitor compounds

Patent metadata

Field	Value
Publication number	US-10908153-B2
Application number	US-201615744190-A
Country	US
Kind code	B2
Filing date	Jul 12, 2016
Priority date	Jul 13, 2015
Publication date	Feb 2, 2021
Grant date	Feb 2, 2021

Abstract

The invention relates to a method of identifying molecules which inhibit the virulence machinery of Pseudomonas aeruginosa, to a device for identifying a molecule which inhibits the virulence machinery of Pseudomonas aeruginosa, to novel compounds which inhibit the virulence machinery of Pseudomonas aeruginosa, to compounds for use for preventing and/or treating a pathogenic infection caused by Pseudomonas aeruginosa and also to pharmaceutical compositions for preventing and/or treating a pathogenic infection caused by Pseudomonas aeruginosa.

First claim

The invention claimed is:

1. A compound of formula (A):

characterized in that:
X is a halogen;
Y is a halogen;
Z is a hydroxy or amine group or an —OR 1 group wherein R 1 is a C 1 -C 4 alkyl or a C 1 -C 4 acyl;
p is an integer and 13>p≥2; and
q is an integer and 13>q≥2;
on the condition that:
if p=4, then q≠8;
if p=10, then q≠4; and
if p=8, then q≠6.

2. The compound of formula (A) according to claim 1 characterized in that:
p=2 and q=2, 4 or 10;
p=4 and q=2, 4 or 6;
p=6 and q=2, 4, 6 or 10; or
p=8 and q=4 or 8.

3. The compound of formula (A) according to claim 1 characterized in that:
Z is —OH or OAc;
Y is Cl;
X is Cl; and
p and q are even numbers.

4. The compound of formula (A) according to claim 3 characterized in that:
p=2 and q=2, 4 or 10;
p=4 and q=2, 4 or 6;
p=6 and q=2, 4, 6 or 10; or
p=8 and q=4 or 8.

5. A process for producing the compound of formula (A) characterized in that the compound of formula B:

wherein
X is a halogen or Cl;
p is an integer and 13>p≥2;
q is an integer and 13>q≥2;
on the condition that:
if p=4, then q≠8;
if p=10, then q≠4; and
if p=8, then q≠6; or

p and q are even numbers;

is reacted in the presence of a catalyst, with the compound of formula C:

wherein

Y is a halogen or Cl;
Z is a hydroxy or amine group or an —OR 1 group wherein R 1 is a C 1 -C 4 alkyl or a C 1 -C 4 acyl or —OH or OAc;
and E is a leaving group selected from the group consisting of trimethylsilyl, tri-isopropyl silyl (TIPS) and dimethyl alcohol.

6. A medicinal product comprising a compound of formula (A) according to claim 1 .

7. A medicinal product comprising a compound of formula (A) according to claim 3 .

8. A method for preventing and/or treating a pathogenic infection caused by Pseudomonas aeruginosa comprising administering to a patient in need thereof a compound of formula (A) according to claim 1 .

9. A method for preventing and/or treating a pathogenic infection caused by Pseudomonas aeruginosa comprising administering to a patient in need thereof a compound of formula (A) according to claim 1 , wherein the pathogenic infection is a nosocomial infection.

10. A method for preventing and/or treating a pathogenic infection caused by Pseudomonas aeruginosa comprising administering to a patient in need thereof a compound of formula (A) according to claim 3 .

11. A method for preventing and/or treating a pathogenic infection caused by Pseudomonas aeruginosa comprising administering to a patient in need thereof a compound of formula (A) according to claim 3 , wherein the pathogenic infection is a nosocomial infection.

Assignees

• Centre Nat Rech Scient
• Commissariat Energie Atomique

Inventors

• Wong Yung-Sing
• Ple Sophie
• Attree Ina
• Barette Caroline

Classifications

• A61K31/352

  condensed with carbocyclic rings, e.g. methantheline  {(cannabinoids A61K31/658)} · CPC title

• A61K31/4709

  Non-condensed quinolines and containing further heterocyclic rings · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• G01N33/543 Primary

  with an insoluble carrier for immobilising immunochemicals · CPC title

• A61P31/04

  Antibacterial agents · CPC title