Antibacterial composition containing an isomer mixture of monosaccharide alkyl monoacetals or monoethers

Patent metadata

Field	Value
Publication number	US-10537103-B2
Application number	US-201515537869-A
Country	US
Kind code	B2
Filing date	Dec 17, 2015
Priority date	Dec 17, 2014
Publication date	Jan 21, 2020
Grant date	Jan 21, 2020

Abstract

A bactericidal or bacteriostatic composition comprising an isomer mixture of monosaccharide alkyl monoethers or monoacetals, its use in the treatment or prevention of Gram-positive bacterial infections, its use as a hygiene or dermatological product for external use and a method for disinfecting surfaces.

First claim

The invention claimed is:

1. A method for disinfection or prevention of bacterial colonization by Gram-positive bacteria of a substrate, comprising:
putting a substrate into contact with a composition comprising a mixture of positional isomers of alkyl monoethers or monoacetals of monosaccharides or monosaccharide alkylglycosides or pharmaceutically acceptable salts thereof, said alkyl group comprising between 11 to 18 carbon atoms, and said alkyl monoethers or monoacetals presenting an ether alkyl or acetal alkyl group on two distinct positions of the monosaccharide or monosaccharide alkylglycoside.

2. The method as claimed in claim 1 , wherein the mixture of positional isomers of alkyl monoethers or monoacetals of monosaccharides or monosaccharide alkylglycosides is obtained by a process comprising the following steps:
a) an acetalization or trans-acetalization of a monosaccharide or monosaccharide alkylglycoside by an aliphatic aldehyde containing from 11 to 18 carbon atoms or the acetal thereof, and
b) recovery of a mixture of alkyl monoether positional isomers of monosaccharide or monosaccharide alkylglycosides obtained by catalytic hydrogenolysis of the alkyl acetal monosaccharide or monosaccharide alkylglycoside obtained in a), in which the alkyl group (R) comprises between 11 to 18 carbon atoms,
or
recovery of a mixture of monosaccharide or monosaccharide derivative alkyl monoacetal positional isomers obtained in a) in which the alkyl group (R) comprises between 11 to 18 carbon atoms.

3. The method as claimed in claim 1 , wherein the monosaccharide is a C6 monosaccharide or an alkylglycoside thereof.

4. The method as claimed in claim 1 , wherein the monosaccharide is a glucoside and said alkyl monoacetal group is in the 1,2-O—, 2,3-O—, 3,4-O— or -4,6-O— position or said alkyl monoether group is in the 4-O— or 6-O— position.

5. The method as claimed in claim 1 , wherein the Gram-positive bacteria are bacteria from the phylum of Firmicutes.

6. The method as claimed in claim 1 , wherein the Gram-positive bacteria are bacteria of the order of Bacillales chosen from the family of Alicyclobacillaceae, Bacillaceae, Caryophanaceae, Listeriaceae, Paenibacillceae, Pasteuriaceae, Planococcaceae, Sporolactobacillaceae, Slaphylococcaceae, Thermoactinomycelacea and Turicibacteraceae.

7. The method as claimed in claim 1 , wherein the Gram-positive bacteria are bacteria from the family of Listeriaceae chosen from L. fleischmannii, L. grayi, L. innocua, L. ivanovii, L. marthii, L. monocytogenes, L. rocourtiae, L. seeligeri, L. weihenstephanensis and L. welshimeri.

8. The method as claimed in claim 1 , wherein the Gram-positive bacteria are bacteria from the family of Staphylococcaceae chosen from bacteria from the genus Staphylococcus, Gemella, Jeotgalicoccus, Macrococcus, Salinicoccus and Nosocomiicoccu.

9. The method as claimed in claim 1 , wherein the Gram-positive bacteria are bacteria from the genus Staphylococcus chosen from chosen from S. arlettae, S. agnetis, S. aureus, S. auricularis, S. capitis, S. caprae, S. carnosus, S. caseolyticus, S. chromogenes, S. cohnii, S. condimenti, S. delphini, S. devriesei, S. epidermidis, S. equorum, S. felis, S. fleurettii, S. gallinarum, S. haemolyticus, S. hominis, S. hyicus, S. intermedius, S. kloosii, S. leei, S. lentus, S. lugdunensis, S. lutrae, S. massiliensis, S. microti, S. muscae, S. nepalensis, S. pasteuri, S. pettenkoferi, S. piscifermentans, S. pseudintermedius, S. pseudolugdunensis, S. pulvereri, S. rostri, S. saccharolyticus, S. saprophyticus, S. schleiferi, S. sciuri, S. simiae, S. simulans, S. stepanovicii, S. succinus, S. vitulinus, S. warneri and S. xylosus.

10. The method as claimed in claim 1 , wherein the Gram-positive bacteria are Lactobacillales chosen from a family of Aerococcaceae, Carnobacteriaceae, Enterococcaceae, Lactobacillaceae, Leuconostocaceae and Streptococcaceae.

11. The method as claimed in claim 1 , wherein the Gram-positive bacteria are bacteria from the family of Enterococcaceae chosen from bacteria in the genus Bavariicoccus, Catellicoccus, Enterococcus, Melissococcus, Pilibacter, Tetragenococcus, Vagococcus.

12. The method as claimed in claim 1 , wherein the Gram-positive bacteria are bacteria from the Enterococcus genus chosen from E. malodoratus, E. avium, E. durans, E. faecalis, E. faecium, E. gallinarum, E. hirae, E. solitarius , preferentially, E. avium, E. durans, E. faecalis and E. faecium.

13. The method as claimed in claim 1 , wherein the substrate is a food, cosmetic, pharmaceutical, phytosanitary, veterinary composition or surface.

14. The method as claimed in claim 1 , wherein the method is used externally for a dermatological purpose.

15. The method as claimed in claim 14 , wherein the infection by Gram-positive bacteria is an infection of the skin or mucous membranes.

16. The method as claimed in claim 2 , wherein the process further comprises the catalytic hydrogenolysis of the obtained alkyl monosaccharide or monosaccharide alklylglycoside acetal.

17. The method as claimed in claim 16 , wherein the catalytic hydrogenolysis is performed without an acid catalyst.

18. The method as claimed in claim 1 , wherein the alkyl group comprises from 11 to 13 carbon atoms.

19. The method as claimed in claim 1 , wherein the monosaccharide is:
a hexose chosen from the group formed by glucose, mannose, galactose, allose, altrose, gulose, idose and talose.

20. The method as claimed in claim 15 , wherein the infection is an infection chosen from folliculitis, abscesses, paronychia, boils, impetigo, infections between the digits, anthrax (staphylococcal anthrax), cellulitis, secondary wound infections, otitis, sinusitis, hidradenitis, infectious mastitis, post-traumatic skin infections or infections on burnt skin.

Assignees

• Tereos Starch & Sweeteners Belgium
• Univ Claude Bernard Lyon
• Centre Nat Rech Scient

Inventors

• Gozlan Charlotte
• Belmessieri Dorine
• Duclos Marie-Christine
• Duguet Nicolas
• Lemaire Marc
• Lina Gérard
• Dumitrescu Oana
• Redl Andreas

Classifications

• A61P31/02

  Local antiseptics · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• A61P29/00

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

• A61P27/16

  Otologicals · CPC title

• C11D3/48

  Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions · CPC title