Methods of applying antibiotic compounds to polyurethane biomaterials using textile dyeing technology

• US 20050196375A1
• Filed: 04/20/2005
• Published: 09/08/2005
• Est. Priority Date: 04/14/2000
• Status: Abandoned Application

• Current Assignee: Frank W. Logerfo, Martin J. Bide, Matthew D. Phaneuf, Michael Szycher, William C. Quist
• Original Assignee: Frank W. Logerfo, Martin J. Bide, Matthew D. Phaneuf, Michael Szycher, William C. Quist
• Inventors: Phaneuf, Matthew D., Szycher, Michael, LoGerfo, Frank W., Bide, Martin J., Quist, William C.
• Application Number:
  US11/110,198
• Publication Number:
  US 20050196375A1
• Time in Patent Office: Days
• US Class Current: 424/78.3
• CPC Class Codes: A61K 47/59 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/44 Polycarbonates

Abstract

The invention provides urethane polymers bonded to therapeutically active compounds, such as antibiotics. The invention also features methods of applying therapeutically active compounds to polyurethane polymers using textile dyeing. These polymers may be used in a variety of clinical applications.

Claims

1. A composition comprising a urethane polymer reversibly bonded to a therapeutically active compound via one or more reactive groups of said polymer.

2. The composition of claim 1, wherein said compound is bonded to said polymer via one or more carboxylic acid, amino, sulfo, and/or hydroxyl groups.

3. The composition of claim 2, wherein at least 25% of the carboxylic acid, amino, sulfo, and/or hydroxyl groups of said polymer are bonded to said compound.

4. The composition of claim 1, wherein said compound is directly bonded to said polymer.

5. The composition of claim 1, wherein said compound is bonded to said polymer through a hydrogen-bond.

6. The composition of claim 1, wherein said compound is bonded to said polymer for at least one day in phosphate-buffered saline at pH 7.4 and at 37°

C.

7. The composition of claim 1, wherein said compound is bonded to said polymer for less than ten days in phosphate-buffered saline at pH 7.4 and at 37°

C.

8. The composition of claim 1, wherein at said compound is bonded to said polymer or a period between one and ten days, inclusive, in phosphate-buffered saline at pH 7.4 and at 37°

C.

9. The composition of claim 1, wherein said compound comprises a carboxylic acid group or an aryl group.

10. The composition of claim 1, wherein said compound is an antibiotic or an antifungal, antiviral, or antiseptic agent.

11. The composition of claim 10, wherein said antibiotic is a quinolone.

12. The composition of claim 11, wherein said quinolone is selected from the group consisting of ciprofloxacin, ofloxacin, norfloxacin, sparfloxacin, tomafloxacin, enofloxacin, lomefloxacin, pefloxacin, fleroxacin, and DU6859a.

13. A biocompatible device comprising a urethane polymer reversibly bonded to a therapeutically active compound via one or more reactive groups of said polymer.

14. The device of claim 13, wherein said device is selected from the group consisting of a catheters, vascular grafts, artificial hearts, blood filters, pacemaker leads, heart valves, and prosthetic grafts.

15. A wound dressing comprising a urethane polymer reversibly bonded to a therapeutically active compound via one or more reactive groups of said polymer.