# US 10,501,487 B2 · Antibacterial bismuth complexes

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- Number: US 10,501,487 B2
- Document ID: US10501487B2
- Status: Granted
- Kind: B2
- Application number: 15/576,531
- Filed: 2016-05-26
- Published: 2018-06-07
- Granted: 2019-12-10
- Earliest claimed: 2015-05-26
- Assignees: Monash University
- Applicants: Monash University
- Inventors: Philip Andrews; Melissa Werrett; Madleen Busse
- Web page: https://patentgrep.com/patent/US10501487B2

## CPC

- C07F 9/94: Bismuth compounds
- A01N 57/22: containing aromatic radicals
- A61K 6/69: Medicaments
- A61K 31/662: Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
- A61K 31/663: Compounds having two or more phosphorus acid groups or esters thereof, e.g. clodronic acid, pamidronic acid
- A61K 33/245: Bismuth; Compounds thereof
- A61K 33/42: Phosphorus; Compounds thereof
- A61L 15/20: containing organic materials
- A61L 15/44: Medicaments
- A61L 17/005: {containing a biologically active substance, e.g. a medicament or a biocide}
- A61L 24/0015: {Medicaments; Biocides}
- A61L 31/08: Materials for coatings
- A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)}
- A61P 31/04: Antibacterial agents
- C09D 5/14: Paints containing biocides, e.g. fungicides, insecticides or pesticides (C09D5/16 takes precedence)
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- A61L 2430/02: for reconstruction of bones; weight-bearing implants
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## 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.

## Claims

### Claim 1

An organobismuth (III) phosphinate complex having a structure comprising formula (a):
wherein
R1 is a phosphinate group;
R2 is an aromatic carbocyclyl or aromatic heterocyclyl group; and
R3 is a phosphinate group, an aromatic carbocyclyl or aromatic heterocyclyl group, or a ligand;
and wherein the complex is not

### Claim 2 (depends on 1)

The complex of claim 1, wherein R3 is a phosphinate group, or an aromatic carbocyclyl or aromatic heterocyclyl group.

### Claim 3 (depends on 2)

The complex of claim 2, wherein R3 is a phosphinate group.

### Claim 4 (depends on 1)

The complex of claim 1, wherein the phosphinate group has the formula (b)
and each Ra is independently selected from the group consisting of hydrogen, optionally substituted C1-10alkyl, optionally substituted C2-10alkenyl, optionally substituted C2-10alkynyl, optionally substituted C3-10 carbocyclyl and optionally substituted C3-10 heterocyclyl.

### Claim 5 (depends on 4)

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

### Claim 6 (depends on 5)

The complex of claim 5, wherein each Ra is hydrogen.

### Claim 7 (depends on 5)

The complex of claim 5, wherein each Ra is unsubstituted C1-6 alkyl.

### Claim 8 (depends on 5)

The complex of claim 5, wherein each Ra is C6-10 aromatic carbocyclyl or C6-10 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, —NO2, —C1-6alkyl, —C2-6alkenyl, —C2-6alkynyl and —OC1-6alkyl.

### Claim 9 (depends on 5)

The complex of claim 5, wherein
Ra is selected from the group consisting of hydrogen, C1-6alkyl, C6-10 aromatic carbocyclyl or C5-10 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, —NO2, —C1-6alkyl, —C2-6alkenyl, —C2-6alkynyl and —OC1-6alkyl; and
R2 is C6-10 aromatic carbocyclyl or C5-10 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, —NO2, C1-6alkyl, —C2-6alkenyl, —C2-6alkynyl and —OC1-6alkyl.

### Claim 10 (depends on 1)

The complex of claim 1, wherein R2 is C6-10 aromatic carbocyclyl or C5-10 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, —NO2, C1-6alkyl, —C2-6alkenyl, —C2-6alkynyl and OC1-6alkyl.

### Claim 11 (depends on 10)

The complex of claim 10, wherein R2 is phenyl which is unsubstituted or substituted with up to 3 substituents each independently selected from the group consisting of halogen, —CN, —NO2, C1-6alkyl, —C2-6alkenyl, —C2-6alkynyl and OC1-6alkyl.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 1)

The complex of claim 1, wherein the complex is:

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 14)

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

### Claim 16 (depends on 14)

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

### Claim 17 (depends on 15)

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.

### Claim 18 (depends on 14)

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.

### Claim 19 (depends on 14)

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.

### Claim 20 (depends on 14)

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

### Claim 21 (depends on 14)

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