Anti-infective functionalized surfaces and methods of making same

Patent metadata

Field	Value
Publication number	US-10596304-B2
Application number	US-201715497909-A
Country	US
Kind code	B2
Filing date	Apr 26, 2017
Priority date	Feb 25, 2009
Publication date	Mar 24, 2020
Grant date	Mar 24, 2020

Abstract

Devices are provided which are functionalized to include surface regions having anti-infective agents. Methods are provided for functionalizing various material surfaces to include active surface regions for binding anti-infective agents. Methods are provided by which anti-infective moieties or agents are bonded to functionalized surfaces.

First claim

The invention claimed is:

1. A method of preparing a medical device having an anti-infective surface, the method comprising
covalently bonding a functionalized organophosphonate to a native oxide surface of a metal,
derivatizing the functionalized organophosponate, and
covalently bonding a quaternary ammonium anti-infective agent to the organophosphonate,
wherein the functionalized organophosphonate is an hydroxy, amino or thiol omega-functionalized organophosphonate where the organo group is a linear or branched, saturated or unsaturated, substituted or unsubstituted, aliphatic or aromatic alkylene hydrocarbon of from 2 to 40 carbon atoms, and
comprising derivatizing the hydroxy, amino or thiol with a cross-coupling reagent;
reacting the derivatized hydroxy, amino or thiol with a diamine or aminoalcohol to bond the organo group of the organophosphonate via a urethane, carbonate, urea, thiocarbonate or thiourea bond and provide a distal amino group; and
quaternizing the distal amino.

2. The method according to claim 1 comprising covalently bonding the functionalized organophosphonate directly to the native oxide surface.

3. The method according to claim 1 comprising contacting a metal alkoxide with the native oxide surface, subjecting the metal alkoxide to conditions adequate to form a metal oxide adhesion layer, the conditions selected from the group consisting of pyrolysis, microwaving, complete or partial hydrolysis, and covalently bonding a functionalized organophosphonate to the metal oxide adhesion layer.

4. The method of claim 3 comprising contacting a zirconium alkoxide with the native oxide surface.

5. The method of claim 3 comprising contacting a zirconium alkoxide with a native oxide surface of titanium.

6. The method of claim 1 wherein the organophosphonate is 11-hydroxyundecylphosphonate.

7. The method of claim 1 wherein the the anti-infective agent is a quaternary alkylammonium moiety.

8. The method of claim 1 wherein the metal is selected from the group consisting of titanium, stainless steel, cobalt chrome, nickel, molybdenum, tantalum, zirconium, magnesium, manganese, niobium, and alloys thereof.

9. The method of claim 1 wherein the metal is titanium.

Assignees

• Orthobond Corp
• Univ Princeton

Inventors

• Clevenger Randell
• Dennes Thomas J
• Schwartz Jeffrey

Classifications

• A61L2300/208

  Quaternary ammonium compounds · CPC title

• A61L31/022

  Metals or alloys · CPC title

• C07F9/3821

  substituted by B, Si, P or a metal (C07F9/3839 takes precedence) · CPC title

• A01N25/10

  Macromolecular compounds · CPC title

• A61L2/16

  using chemical substances · CPC title