Antibacterial bismuth complexes

Patent metadata

Field	Value
Publication number	US-10501487-B2
Application number	US-201615576531-A
Country	US
Kind code	B2
Filing date	May 26, 2016
Priority date	May 26, 2015
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

Provided herein are organobismuth (III) phosphinate complexes, which comprise a phosphinate group and an aromatic carbocyclyl or aromatic heterocyclyl group. The complexes find use as antibacterial agents, and accordingly also provided herein are products, devices, compositions and materials comprising the complexes, for example medical products such as wound dressings and bandages.

First claim

The invention claimed is:

1. An organobismuth (III) phosphinate complex having a structure comprising formula (a):

wherein
R 1 is a phosphinate group;
R 2 is an aromatic carbocyclyl or aromatic heterocyclyl group; and
R 3 is a phosphinate group, an aromatic carbocyclyl or aromatic heterocyclyl group, or a ligand;
and wherein the complex is not

2. The complex of claim 1 , wherein R 3 is a phosphinate group, or an aromatic carbocyclyl or aromatic heterocyclyl group.

3. The complex of claim 2 , wherein R 3 is a phosphinate group.

4. The complex of claim 1 , wherein the phosphinate group has the formula (b)

and each R a is independently selected from the group consisting of hydrogen, optionally substituted C 1-10 alkyl, optionally substituted C 2-10 alkenyl, optionally substituted C 2-10 alkynyl, optionally substituted C 3-10 carbocyclyl and optionally substituted C 3-10 heterocyclyl.

5. The complex of claim 4 , wherein the complex has the formula (c)

6. The complex of claim 5 , wherein each R a is hydrogen.

7. The complex of claim 5 , wherein each R a is unsubstituted C 1-6 alkyl.

8. The complex of claim 5 , wherein each R a is C 6-10 aromatic carbocyclyl or C 6-10 aromatic heterocyclyl, said aromatic carbocyclyl or aromatic heterocyclyl being unsubstituted or substituted with up to 3 substituents selected from the group consisting of halogen, —CN, —NO 2 , —C 1-6 alkyl, —C 2-6 alkenyl, —C 2-6 alkynyl and —OC 1-6 alkyl.

9. The complex of claim 5 , wherein
R a is selected from the group consisting of hydrogen, C 1-6 alkyl, C 6-10 aromatic carbocyclyl or C 5-10 aromatic heterocyclyl, said aromatic carbocyclyl or aromatic heterocyclyl being unsubstituted or substituted with up to 3 substituents selected from the group consisting of halogen, —CN, —NO 2 , —C 1-6 alkyl, —C 2-6 alkenyl, —C 2-6 alkynyl and —OC 1-6 alkyl; and
R 2 is C 6-10 aromatic carbocyclyl or C 5-10 aromatic heterocyclyl, said aromatic carbocyclyl or aromatic heterocyclyl being unsubstituted or substituted with up to 3 substituents each independently selected from the group consisting of halogen, —CN, —NO 2 , C 1-6 alkyl, —C 2-6 alkenyl, —C 2-6 alkynyl and —OC 1-6 alkyl.

10. The complex of claim 1 , wherein R 2 is C 6-10 aromatic carbocyclyl or C 5-10 aromatic heterocyclyl, said aromatic carbocyclyl or aromatic heterocyclyl being unsubstituted or substituted with up to 3 substituents each independently selected from the group consisting of halogen, —CN, —NO 2 , C 1-6 alkyl, —C 2-6 alkenyl, —C 2-6 alkynyl and OC 1-6 alkyl.

11. The complex of claim 10 , wherein R 2 is phenyl which is unsubstituted or substituted with up to 3 substituents each independently selected from the group consisting of halogen, —CN, —NO 2 , C 1-6 alkyl, —C 2-6 alkenyl, —C 2-6 alkynyl and OC 1-6 alkyl.

12. The complex of claim 1 , wherein the complex is selected from the group consisting of:

13. The complex of claim 1 , wherein the complex is:

14. A product, device, material, or composition comprising a complex of claim 1 .

15. The product, device, material, or composition of claim 14 , wherein the product, device, material or composition comprises an antibacterial surface coating comprising the complex.

16. The composition of claim 14 , wherein the composition is a polymerisable and/or curable composition.

17. The product, device, material, or composition of claim 15 , wherein the product, device, material, or composition is a wound dressing, a suture, a surgical implement, or a medical implant.

18. The product, device, composition, or material of claim 14 , wherein the product, device, material, or composition is a medical adhesive, a bone cement, a dental adhesive or a dental filler composition.

19. The product, device, material, or composition of claim 14 , wherein the product, device, material, or composition is for use in building construction, renovation, and/or maintenance and wherein the product, device, material, or composition is a coating, sealant, cement, concrete, grout, mortar, or stucco composition.

20. The product, device, material, or composition of claim 14 , wherein the product, device, material, or composition comprises antibacterial packaging comprising the complex.

21. The product, device, material, or composition of claim 14 , wherein the product, device, material, or composition is a cellulosic material.

Assignees

• Univ Monash

Inventors

• Andrews Philip
• Werrett Melissa
• Busse Madleen

Classifications

• A61P31/04

  Antibacterial agents · CPC title

• A61K6/69

  Medicaments · CPC title

• A61K33/42

  Phosphorus; Compounds thereof · CPC title

• A61K33/245

  Bismuth; Compounds thereof · CPC title

• A61L24/0015

  Medicaments; Biocides · CPC title