Polyurethane-sealed biocompatible device and method for its preparation

• US 20010053933A1
• Filed: 02/28/2001
• Published: 12/20/2001
• Est. Priority Date: 02/29/2000
• Status: Active Grant

• Current Assignee: Biomod Surfaces, BETH Israel Deaconess Medical Center (Caregroup Incorporated)
• Original Assignee: Biomod Surfaces
• Inventors: Phaneuf, Matthew D., Quist, William C., Dempsey, Donald J., Logerfo, Frank W.
• Granted Patent: US 6,743,253 B2
• Time in Patent Office: Days
• US Class Current: 623/1.48
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 27/40 Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
• CPC Class Codes: A61L 27/507 for artificial blood vessels apparatus for applying cells on a blood vessel prosthesis A61F2/062
• CPC Class Codes: A61L 27/54 Biologically active materials, e.g. therapeutic substances A61L27/227 takes precedence
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/34 Carboxylic acids; Esters thereof with monohydroxyl compounds
• CPC Class Codes: C08G 18/44 Polycarbonates
• CPC Class Codes: C08L 23/06 Polyethene
• CPC Class Codes: C08L 23/12 Polypropene
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 77/00 Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

Provided is a biocompatible device which has been coated or sealed with a polyether or polyether/carbonate based urethane polymer that contains functional groups (e.g. carboxylic acid groups) which are capable of serving as anchor sites for protein binding.

Claims

1. A biocompatible device, comprising:

(a) a polymeric base; and

(b) a surface layer coating said polymeric base, said surface layer comprising a polyether or polyether/carbonate based urethane polymer prepared by a method comprising the steps of;

(i) forming a diisocyanate terminated prepolymer based on (i) a polyether glycol or polyether/cabonate glycol having a molecular weight between about 200 to 3,000 Da and (ii) a diisocyanate having the general structure OCN—

R′

—

NCO, wherein R′

is a hydrocabon; and

(ii) chain extending said prepolymer using a dihydroxy carboxylic acid.

2. The device of

claim 1

, wherein said device is a vascular graft comprising a graft wall base and a surface layer coating the inner or outer surface of said graft wall base.

3. The device of

claim 2

, wherein said graft wall comprises a polymeric material selected from the group consisting of polyethylene terephthalate, polyurethane, polyethylene, polypropylene, silicons, and nylon.

4. The device of

claim 3

, wherein said graft is a knitted polyethylene terephthalate double velour vascular graft.

5. The device of

claim 2

, wherein proteins are covalently attached to said surface layer.

6. The device of

claim 5

, wherein said proteins are selected from the group consisting of anti-clotting agents, thrombolytic agents, mitogenic agents, growth promoting substances, and inhibitors.

7. The device of

claim 6

, wherein said proteins comprise vascular endothelial growth factor (VEGF) and recombinant hirudin (rHir).

8. The device of

claim 1

, wherein said diisocyanate is selected from the group consisting of 4,4′

-diphenylmethane diisocyanate (MDI), hydrogenated methylene diisocyanate (HMDI), hexamethylene diisocyanate, toluene diisocyanates, 4,4′

-tolidine diisocyanate, m-phenylene diisocyanate, 4-chloro-1,3-phenylene diisocyanate, 4,4-tetramethylene diisocyante, 1,6-hexamethylene diisocyanate, 1,10-decamethylene diisocyanate, 1,4-cyclohexylene diisocyanate, 4,4′

-methylene bis (cyclo hexylisocyanate), 1,4-isophorone diisocyanate, 3,3′

-dimethyl-4,4′

-diphenylmethane diisocyanate, and 1,5-tetrahydronaphthalene diisocyanate.

9. The device of

claim 8

, wherein said diisocyanate is 4,4′

-diphenylmethane diisocyanate (MDI).

10. The device of

claim 1

, wherein said polyether glycol is polytetramethylene ether glycol (PTMEG1000).

11. The device of

claim 1

, wherein said polyether/carbonate glycol is polyetherpolycarbonatediol.

12. The device of

claim 1

, wherein said carboxylic acid is 2,2-bis(hydroxymethyl)-propionic acid (DHMPA).

13. The device of

claim 1

, wherein said molecular weight is about 1,000 Da.

14. The device of

claim 2

, wherein said graft has a vascular shape with an internal diameter between about 2.0 and 20.0 mm.

15. The device of

claim 2

, wherein said graft has a vascular shape with an internal diameter less than about 9.0 mm.

16. The device of

claim 15

, wherein said graft has a vascular shape with an internal diameter less than about 6.0 mm.

17. The device of

claim 16

, wherein said graft has a vascular shape with an internal diameter less than about 5.0 mm.

18. The device of

claim 14

, wherein said graft has a vascular shape with an internal diameter between 6.0 and 8.0 mm.