# US 10,864,304 B2 · Anti-infective antimicrobial-containing biomaterials

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- Number: US 10,864,304 B2
- Document ID: US10864304B2
- Status: Granted
- Kind: B2
- Application number: 14/281,682
- Filed: 2014-05-19
- Published: 2015-01-22
- Granted: 2020-12-15
- Earliest claimed: 2009-08-11
- Assignees: Atrium Medical Corporation
- Applicants: Atrium Medical Corporation
- Inventors: Keith M. Faucher; Hilda N. Rono; Anthony Richard Horton; Jocelyn Choroszy; Paul Martakos
- Web page: https://patentgrep.com/patent/US10864304B2

## CPC

- A61L 31/08: Materials for coatings
- A01N 37/36: containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N 61/00: Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
- A61K 31/09: having two or more such linkages
- A61K 31/155: Amidines ([IMAGE cpc-sch-A61K-1029.gif]), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
- A61K 31/202: having three or more double bonds, e.g. linolenic (eicosanoids, e.g. leukotrienes A61K31/557)
- A61K 31/232: having three or more double bonds, e.g. etretinate
- A61K 31/35: having six-membered rings with one oxygen as the only ring hetero atom
- A61K 31/765: Polymers containing oxygen
- A61K 33/38: Silver; Compounds thereof
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61L 15/34: Oils, fats, waxes or natural resins {(A61L15/225 takes precedence)}
- A61L 15/46: Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
- A61L 27/50: Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials}
- A61L 27/54: Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)}
- A61L 29/14: Materials characterised by their function or physical properties {, e.g. lubricating compositions}
- A61L 29/16: Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)}
- A61L 31/005: {Ingredients of undetermined constitution or reaction products thereof}
- A61L 31/14: Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials}
- A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)}
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61L 2300/104: Silver, e.g. silver sulfadiazine
- A61L 2300/22: Lipids, fatty acids, e.g. prostaglandins, oils, fats, waxes
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- A61L 2300/406: Antibiotics
- A61L 2300/45: Mixtures of two or more drugs, e.g. synergistic mixtures
- A61L 2300/602: Type of release, e.g. controlled, sustained, slow
- A61L 2300/624: Nanocapsules
- A61L 2420/06: Coatings containing a mixture of two or more compounds
- 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)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A material including a plurality of fatty acid chains cross-linked together and a silver fatty acid salt formed with the fatty acid chains within the material. Methods for forming a material are also included. The silver-containing materials can be utilized alone or in combination with a medical device for the release and local delivery of one or more anti-infective agents.

## Claims

### Claim 1

A material comprising:
a plurality of fatty acid chains at least partially cross-linked together to form a bioabsorbable gel; and
a silver fatty acid salt formed in an aqueous environment with at least some of the at least partially cross-linked fatty acid chains within the material, wherein the silver fatty acid salt comprises silver ions and is characterized by an FTIR peak at about 1512 cm−1.

### Claim 2 (depends on 1)

The material of claim 1, wherein the silver fatty acid salt is formed from an interaction between the at least partially cross-linked fatty acid chains and an aqueous silver solution.

### Claim 3 (depends on 2)

The material of claim 2, wherein the silver solution includes silver nitrate or silver acetate.

### Claim 4 (depends on 1)

The material of claim 1, wherein the at least partially cross-linked fatty acid chains are cross-linked together by at least partially curing an oil.

### Claim 5 (depends on 4)

The material of claim 4, wherein the fatty acid chains are omega-3 fatty acids and the oil is a fish oil.

### Claim 6 (depends on 1)

A coating or film comprising the material of claim 1.

### Claim 7 (depends on 6)

The coating or film of claim 6 having an additional antimicrobial compound applied to an outer surface of the coating or film.

### Claim 8 (depends on 1)

The material of claim 1, wherein the silver fatty acid salt is dispersed in a soaked pattern in the material.

### Claim 9 (depends on 1)

The material of claim 1, wherein the silver fatty acid salt is suspended uniformly in the material.

### Claim 10 (depends on 1)

The material of claim 1, wherein the at least partially cross-linked plurality of fatty acid chains include one or more cross-links selected from the group consisting of ester cross-links, peroxide bridges, ether bridges and hydrocarbon bridges.

### Claim 11 (depends on 1)

The material of claim 1, wherein the silver fatty acid salt load in the material is sufficient to inhibit bacterial growth during implantation.

### Claim 12 (depends on 1)

The material of claim 1, wherein when the material becomes hydrated in an aqueous environment the material releases silver ions.

### Claim 13 (depends on 7)

The coating or film of claim 7, wherein the additional antimicrobial compound is triclosan.

### Claim 14 (depends on 1)

A method for forming a material, comprising the steps of:
at least partially curing an oil comprising fatty acids in order to at least partially cross-link chains of the fatty acids together to form the bioabsorbable gel;
soaking the bioabsorbable gel in an aqueous silver solution; and
evaporating a solvent from the aqueous silver solution to form silver fatty acid salts within the bioabsorbable gel so as to form the material according to claim 1.

### Claim 15 (depends on 14)

The method of claim 14, wherein the aqueous silver solution includes silver acetate or silver nitrate.

### Claim 16 (depends on 14)

The method of claim 14, wherein the at least partially curing includes at least partially curing the fatty acids to form a biomaterial on a medical device.

### Claim 17 (depends on 16)

The method of claim 16, wherein the medical device is a bandage, a stent, a graft, a shunt, a catheter, a balloon, or a surgical mesh.

### Claim 18 (depends on 1)

A method for forming a material according to claim 1, comprising the step of:
at least partially curing an oil to at least partially oxidize fatty acids within the oil to form a pre-cured oil;
combining the pre-cured oil with a substantially uncured oil to form an oil formulation;
combining an aqueous silver solution with the oil formulation; and
curing the oil formulation and the aqueous silver solution combination to react silver ions of the aqueous silver solution with the pre-cured oil of the oil formulation to convert the aqueous silver solution at least partially into elemental silver within the material.

### Claim 19 (depends on 18)

The method of claim 18, wherein the pre-cured oil and the substantially uncured oil both include fish oil.

### Claim 20 (depends on 18)

The method of claim 18, wherein curing also includes cross-linking fatty acids within the oil formulation to each other.

### Claim 21 (depends on 18)

The method of claim 18, wherein the pre-cured oil and the substantially uncured oil are combined in an approximately equal ratio.

### Claim 22 (depends on 18)

The method of claim 18, wherein at least partially curing the oil includes forming hydroperoxides in the oil, and wherein the silver ions react with the hydroperoxides to form the elemental silver from the aqueous silver solution.