Antibacterial compound and uses of same

Patent metadata

Field	Value
Publication number	US-11414403-B2
Application number	US-201816650707-A
Country	US
Kind code	B2
Filing date	Sep 24, 2018
Priority date	Sep 25, 2017
Publication date	Aug 16, 2022
Grant date	Aug 16, 2022

Abstract

A new compound exhibiting particularly advantageous antibacterial properties, and having the structural formula:L-pyroglutamyl-L-1-aminoethyltetrazole (or N-(1-(1H-tetrazol-5-yl)ethyl)-5-oxopyrrolidine-2-carboxamide). Also, the use of this compound in microbiological culture methods and media intended for the detection, identification, enrichment, counting and/or isolation of target microorganisms that may be encountered in samples taken for clinical diagnosis or microbiological health control purposes.

First claim

The invention claimed is:

1. L-pyroglutamyl-L-1-aminoethyltetrazole having the structural formula:

2. An in vitro microbiological culture method, wherein microorganisms that may be present in a sample to be analyzed and/or to be treated are inoculated in or on a microbiological culture medium comprising L-pyroglutamyl-L-1-aminoethyltetrazole (12) as claimed in claim 1 , at a non-zero concentration, less than or equal to 1 g/l.

3. The culture method as claimed in claim 2 , wherein the L-pyroglutamyl-L-1-aminoethyltetrazole is present in the microbiological culture medium at a concentration:
of between 10 and 1, 1000 mg/l for inhibiting at least one bacterium chosen from the bacterial species consisting of: Klebsiella pneumoniae, Serratia marcescens, Yersinia enterocolitica, Bacillus subtilis, Enterococcus faecalis and Enterococcus faecium ; or of between 2 and 50 mg/l for inhibiting at least one bacterium chosen from the bacterial species consisting of: Klebsiella pneumoniae, Serratia marcescens, Yersinia enterocolitica, Enterococcus faecalis and Enterococcus faecium ; or
of between 1 and 10 mg/l for inhibiting at least one bacterium chosen from the bacterial species consisting of: Yersinia enterocolitica, Enterococcus faecalis and Enterococcus faecium ; or
which is non-zero, less than or equal to 5 mg/l for inhibiting at least one bacterium chosen from the bacterial species consisting of: Enterococcus faecalis and Enterococcus faecium;
the at least one bacterium being capable of being present in the sample to be analyzed and/or to be treated.

4. The culture method as claimed in claim 2 , wherein the L-pyroglutamyl-L-1-aminoethyltetrazole is present in the microbiological culture medium at a concentration:
of between 10 and 1,1000 mg/l with a view to detecting, identifying, counting and/or isolating at least one target microorganism chosen from the bacterial species consisting of: Acinetobacter baumannii, Burkholderia cepacia, Enterobacter cloacae, Escherichia coli, Providencia rettgeri, Pseudomonas aeruginosa, Salmonella typhimurium, Salmonella enteritidis, Listeria monocytogenes, Staphylococcus epidermidis, Staphylococcus aureus, Streptococcus agalactiae ; or
of between 2 and 50 mg/l with a view to detecting, identifying, counting and/or isolating at least one target microorganism chosen from the bacterial species consisting of: Acinetobacter baumannii, Burkholderia cepacia, Enterobacter cloacae, Escherichia coli, Providencia rettgeri, Pseudomonas aeruginosa, Salmonella typhimurium, Salmonella enteritidis, Bacillus subtilis, Listeria monocytogenes, Staphylococcus epidermidis, Staphylococcus aureus, Streptococcus agalactiae ; or
of between 1 and 10 mg/l with a view to detecting, identifying, counting and/or isolating at least one target microorganism chosen from the bacterial species consisting of: Acinetobacter baumannii, Burkholderia cepacia, Enterobacter cloacae, Escherichia coli, Klebsiella pneumoniae, Providencia rettgeri, Pseudomonas aeruginosa, Salmonella typhimurium, Serratia marcescens, Salmonella enteritidis, Bacillus subtilis, Listeria monocytogenes, Staphylococcus epidermidis, Staphylococcus aureus, Streptococcus agalactiae ; or
which is non-zero, less than or equal to 5 mg/l with a view to detecting, identifying, counting and/or isolating at least one target microorganism chosen from the bacterial species consisting of: Acinetobacter baumannii, Burkholderia cepacia, Enterobacter cloacae, Escherichia coli, Klebsiella pneumoniae, Providencia rettgeri, Pseudomonas aeruginosa, Salmonella typhimurium, Serratia marcescens, Yersinia enterocolitica, Salmonella enteritidis, Bacillus subtilis, Listeria monocytogenes, Staphylococcus epidermidis, Staphylococcus aureus, Streptococcus agalactiae ; or
the at least one target microorganism being capable of being present in the sample to be analyzed and/or to be treated.

5. A microbiological culture medium comprising, as selective agent, at least L-pyroglutamyl-L-1-aminoethyltetrazole (12) as claimed in claim 1 , at a non-zero concentration, less than or equal to 1 g/1.

6. The microbiological culture medium as claimed in claim 5 , for the detection, identification, counting and/or isolation of at least one target microorganism chosen from the bacterial species consisting of: Acinetobacter baumannii, Burkholderia cepacia, Enterobacter cloacae, Escherichia coli, Klebsiella pneumoniae, Providencia rettgeri, Pseudomonas aeruginosa, Salmonella typhimurium, Serratia marcescens, Yersinia enterocolitica, Salmonella enteritidis, Bacillus subtilis, Listeria monocytogenes, Staphylococcus epidermidis, Staphylococcus aureus, Streptococcus agalactiae;
wherein the L-pyroglutamyl-L-1-aminoethyltetrazole is present at a concentration of between 10 and 1000 mg/l.

7. The microbiological culture medium as claimed in claim 5 , for the detection, identification, counting and/or isolation of at least one target microorganism chosen from the bacterial species consisting of: Acinetobacter baumannii, Burkholderia cepacia, Enterobacter cloacae, Escherichia coli, Providencia rettgeri, Pseudomonas aeruginosa, Salmonella typhimurium, Salmonella enteritidis, Bacillus subtilis, Listeria monocytogenes, Staphylococcus epidermidis, Staphylococcus aureus, Streptococcus agalactiae;
wherein the L-pyroglutamyl-L-1-aminoethyltetrazole is present at a concentration of between 2 and mg/l.

8. The microbiological culture medium as claimed in claim 5 , for the detection, identification, counting and/or isolation of at least one target microorganism chosen for the bacterial species consisting of: Acinetobacter baumannii, Burkholderia cepacia, Enterobacter cloacae, Escherichia coli, Klebsiella pneumoniae, Providencia rettgeri, Pseudomonas aeruginosa, Salmonella typhimurium, Serratia marcescens, Salmonella enteritidis, Bacillus subtilis, Listeria monocytogenes, Staphylococcus epidermidis, Staphylococcus aureus, Streptococcus agalactiae;
wherein the L-pyroglutamyl-L-1-aminoethyltetrazole is present at a non-zero concentration, less than or equal to 5 mg/l.

Assignees

• Biomerieux Sa

Inventors

• Anderson Rosaleen
• Gray Mark
• Kondacs Laszlo
• Orenga Sylvain
• Perry John

Classifications

• A01N43/713

  having rings with four or more nitrogen atoms as the only ring hetero atoms · CPC title

• C12Q1/18

  Testing for antimicrobial activity of a material · CPC title

• C07D403/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C12N1/20

  Bacteria; Culture media therefor · CPC title