Biomaterial drug delivery and surface modification compositions

• US 7,850,982 B2
• Filed: 12/01/2005
• Issued: 12/14/2010
• Est. Priority Date: 12/01/2004
• Status: Expired due to Fees

• Current Assignee: Covidien LP (Medtronic Plc)
• Original Assignee: Tyco Healthcare Group LP (Medtronic Plc)
• Inventors: Nentwick, Brian, Cuevas, Brian, Irfan, Ali, Tsai, Steven, Stopek, Joshua, Hotter, Joseph
• Primary Examiner(s): Hartley; Michael G
• Assistant Examiner(s): DICKINSON, PAUL W
• Application Number:
  US11/292,172
• Publication Number:
  US 20060193884A1
• Time in Patent Office: 1,839 Days
• Field of Search: None
• US Class Current: 424/400
• CPC Class Codes: A61B 17/06166 Sutures suture materials A61L17/00; manufacture of artificial threads D01D; treatment of threads D06M
• CPC Class Codes: A61B 17/064 Surgical staples, i.e. penetrating the tissue
• CPC Class Codes: A61B 17/08 Wound clamps or clips, i.e. not or only partly penetrating the tissue suture bridges A61B17/0466; Devices for bringing together the edges of a wound
• CPC Class Codes: A61B 17/11 for performing anastomosis; Buttons for anastomosis
• CPC Class Codes: A61B 17/122 Clamps or clips , e.g. for the umbilical cord for the vas deferens A61F6/206
• CPC Class Codes: A61B 2017/00831 Material properties
• CPC Class Codes: A61B 2017/00889 antimicrobial, disinfectant
• CPC Class Codes: A61K 31/715 Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
• CPC Class Codes: A61L 17/10 containing macromolecular materials
• CPC Class Codes: A61L 31/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: C08L 71/02 Polyalkylene oxides

Abstract

Compositions are provided which include a polymer made at least in part from a polyoxyalkylene copolymer, such as a poloxamer. The polymer may be combined with a second component to form a blend or emulsion. The resulting composition may be utilized to form medical devices, drug delivery devices, or coatings for other medical devices.

Claims

1. A blend comprising:

a bioabsorbable terpolymer comprising from about 30 to about 50 weight percent of a polyoxyalkylene copolymer, from about 40 to about 50 weight percent epsilon-caprolactone, the balance of the copolymer comprising at least one other copolymerizable monomer selected from the group consisting of glycolide, lactide, p-dioxanone and trimethylene carbonate; and

a polymer comprising two or more monomers selected from the group consisting of lactide, glycolide, lactic-acid, lactones, glycolic acid;

carbonates, orthoesters, absorbable urethanes, absorbable nylons, polyethylene glycol-polypropylene glycol, polystyrene, n-vinyl pyrrolidine, n-vinyl pyridine, C₁-C₁₂ acrylate monomer, C₁-C₁₂ methacrylate monomer, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylic acid, potassium sulfopropyl acrylate, potassium sulfopropyl methacrylate, and 2-methacryloyl phosphorocholine.

2. The blend of claim 1 wherein the polymer comprises a copolymer of epsilon caprolactone and glycolide.

3. The blend of claim 1 further comprising a fatty acid component.

4. The blend of claim 3 wherein the fatty acid component comprises a salt of a C₆ or higher fatty acid.

5. The blend of claim 4 wherein the fatty acid salt is selected from the group consisting of calcium, magnesium, barium, aluminum, and zinc salts of C₆ or higher fatty acids.

6. The blend of claim 4 wherein the fatty acid salt comprises calcium stearate.

7. The blend of claim 3 wherein the fatty acid component comprises a salt of a fatty acid ester selected from the group consisting of magnesium stearoyl lactylate, aluminum stearoyl lactylate, barium stearoyl lactylate, zinc stearoyl lactylate, calcium palmityl lactylate, magnesium palmityl lactylate, aluminum palmityl lactylate, barium palmityl lactylate, or zinc palmityl lactylate, calcium olelyl lactylate, magnesium olelyl lactylate, aluminum olelyl lactylate, barium olelyl lactylate, zinc olelyl lactylate and calcium stearoyl lactylate.

8. The blend of claim 1 further comprising a wax.

9. The blend of claim 8 wherein the wax is selected from the group consisting of polyethylene wax, ethylene copolymer wax, halogenated hydrocarbon waxes, hydrogenated vegetable oil, beeswax, caranuba wax, paraffin, microcrystalline wax, candelillia, spermacetic wax, and mixtures thereof.

10. The blend of claim 1 further comprising a phospholipid.

11. The blend of claim 10 wherein the phospholipid is selected from the group consisting of phosphatidylcholine, mono-acyl phosphatidylcholine, diacyl phosphatidylcholine, phosphatidylserine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylglycerol, plasmalogen, sphingomyelin, ceramide, ciliatin, and copolymers having phosphorylcholine groups.

12. The blend of claim 1 further comprising a medicinal agent.

13. The blend of claim 12 wherein the medicinal agent is selected from the group consisting of antimicrobials, analgesics, antipyretics, anesthetics, antiepileptics, antihistamines, anti-inflammatories, cardiovascular drugs, diagnostic agents, sympathomimetics, cholinomimetics, antimuscarinics, antispasmodics, hormones, growth factors, muscle relaxants, adrenergic neuron blockers, antineoplastics, immunosuppressants, gastrointestinal drugs, diuretics, proteins, nucleic acids, steroids, polysaccharides, and enzymes.

14. A medical device fabricated in whole or in part from the blend of claim 1.

15. A surgical suture coated with a composition comprising the blend of claim 1.

16. An emulsion comprising:

a bioabsorbable terpolymer comprising about 30 to about 50 weight percent of a polyoxyalkylene copolymer, about 40 to about 50 weight percent epsilon-caprolactone, the balance of the copolymer comprising at least one other copolymerizable monomer selected from the group consisting of glycolide, lactide, p-dioxanone and trimethylene carbonate; and

a polymer derived from two or more monomers selected from the group consisting of lactide, glycolide, lactic acid, lactones, glycolic acid, carbonates, orthoesters, absorbable urethanes, absorbable nylons, polyethylene glycol-polypropylene glycol, polystyrene, n-vinyl pyrrolidine, n-vinyl pyridine, C₁-C₁₂ acrylate monomer, C₁-C₁₂ methacrylate monomer, hydroxyethyl methacrylate, hydroxypropyl methacrylate, acrylic acid, potassium sulfopropyl acrylate, potassium sulfopropyl methacrylate, and 2-methacryloyl phosphorocholine.

17. The emulsion of claim 16 wherein the polymer comprises a copolymer of epsilon caprolactone and glycolide.

18. The emulsion of claim 16 further comprising a fatty acid component.

19. The emulsion of claim 18 wherein the fatty acid component comprises a salt of a C₆ or higher fatty acid.

20. The emulsion of claim 19 wherein the fatty acid salt is selected from the group consisting of calcium, magnesium, barium, aluminum, and zinc salts of C₆ or higher fatty acids.

21. The emulsion of claim 19 wherein the fatty acid salt comprises calcium stearate.

22. The emulsion of claim 18 wherein the fatty acid component comprises a salt of a fatty acid ester selected from the group consisting of magnesium stearoyl lactylate, aluminum stearoyl lactylate, barium stearoyl lactylate, zinc stearoyl lactylate, calcium palmityl lactylate, magnesium palmityl lactylate, aluminum palmityl lactylate, barium palmityl lactylate, or zinc palmityl lactylate, calcium olelyl lactylate, magnesium olelyl lactylate, aluminum olelyl lactylate, barium olelyl lactylate, zinc olelyl lactylate and calcium stearoyl lactylate.

23. The blend of claim 16 further comprising a wax.

24. The blend of claim 23 wherein the wax is selected from the group consisting of polyethylene wax, ethylene copolymer wax, halogenated hydrocarbon waxes, hydrogenated vegetable oil, beeswax, caranuba wax, paraffin, microcrystalline wax, candelillia, spermacetic wax, and mixtures thereof.

25. The blend of claim 16 further comprising a phospholipid.

26. The blend of claim 25 wherein the phospholipid is selected from the group consisting of phosphatidylcholine, mono-acyl phosphatidylcholine, diacyl phosphatidylcholine, phosphatidylserine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylglycerol, plasmalogen, sphingomyelin, ceramide, ciliatin, and copolymers having phosphorylcholine groups.

27. The emulsion of claim 16 further comprising a medicinal agent.

28. The emulsion of claim 27 wherein the medicinal agent is selected from the group consisting of antimicrobials, analgesics, antipyretics, anesthetics, antiepileptics, antihistamines, anti-inflammatories, cardiovascular drugs, diagnostic agents, sympathomimetics, cholinomimetics, antimuscarinics, antispasmodics, hormones, growth factors, muscle relaxants, adrenergic neuron blockers, antineoplastics, immunosuppressants, gastrointestinal drugs, diuretics, proteins, nucleic acids, steroids, polysaccharides, and enzymes.

29. A drug delivery device fabricated in whole or in part from the emulsion of claim 16.

30. A surgical suture coated with a composition comprising the emulsion of claim 16.