Synthetic heart valves composed of zwitterionic polymers

• US 10,299,915 B2
• Filed: 03/28/2016
• Issued: 05/28/2019
• Est. Priority Date: 04/09/2015
• Status: Active Grant

• Current Assignee: Boston Scientific Scimed (Boston Scientific Corporation)
• Original Assignee: Boston Scientific Scimed (Boston Scientific Corporation)
• Inventors: Edelman, Peter G., Boden, Mark W., Delaney, Jr., Joseph Thomas
• Primary Examiner(s): Bernatz, Kevin M
• Application Number:
  US15/082,293
• Publication Number:
  US 20160296322A1
• Time in Patent Office: 1,156 Days
• Field of Search: None
• CPC Class Codes: A61F 2/2412 with soft flexible valve members, e.g. tissue valves shaped like natural valves check valves with flexible valve members in general F16K15/14
• CPC Class Codes: A61F 2002/009 for hindering or preventing attachment of biological tissue of bone tissue onto implantable joints A61F2002/30932
• CPC Class Codes: A61F 2310/00389 The prosthesis being coated or covered with a particular material
• CPC Class Codes: A61L 27/00 Materials for grafts or prostheses or for coating grafts or prostheses dental prostheses A61C13/00; shape or structure of prostheses A61F2/00; use of preparations for artificial teeth A61K6/80; artificial kidneys A61M1/14
• CPC Class Codes: A61L 27/14 Macromolecular materials
• CPC Class Codes: C08L 101/02 characterised by the presence of specified groups , e.g. terminal or pendant functional groups

Abstract

A prosthetic heart valve includes a plurality of synthetic polymeric leaflets. Each leaflet has a base polymer and a polymer coating at least partially disposed over the base polymer, wherein the polymer coating includes polymerized units of a monomer comprising a zwitterionic group when the polymer coating is exposed to an aqueous environment at a pH of about 7.4.

Claims

1. A prosthetic heart valve comprising

a plurality of synthetic polymeric leaflets, each leaflet having a base polymer and a polymer coating disposed over the base polymer,

wherein the polymer coating comprises a trimethoxysilane functionalized polymer comprising zwitterionic pendant groups, wherein each zwitterionic pendant group comprises an anionic group and a cationic group.

2. The prosthetic heart valve of claim 1, wherein the anionic group of the zwitterionic pendant group is formed by a phosphoric acid group.

3. The prosthetic heart valve of claim 1, wherein the cationic group of the zwitterionic pendant group is formed by an (cyclo)aliphatic or aromatic amine, an amidine, or a guanidine;

or is a quaternary amine.

4. The prosthetic heart valve of claim 1, wherein the polymer coating consists essentially of the polymer comprising zwitterionic pendant groups.

5. The prosthetic heart valve of claim 1, wherein the cationic group is a quaternary amine.

6. The prosthetic heart valve of claim 1, wherein the pendant group has the structure X—

(CH₂)_n—

O—

Y—

(CH₂)_m—

Z, wherein;

X is the point of covalent attachment to the repeat unit of the monomer;

each R is independently selected from C1- to C4-alkyl;

n and m are each integers between 1 and 8;

Y is either P(O⁻

) or PO₃⁻

; and

Z is a cationic group derived from a (cyclo)aliphatic or aromatic amine, an amidine, a guanidine, or a quaternary amine, NR′

₃⁺, wherein each R′

is independently selected from C1- to C4-alkyl.

7. The prosthetic heart valve of claim 1, wherein the polymer of the polymer coating is the reaction product of one or more monomer species having a structure selected from the group consisting of:

8. The prosthetic heart valve of claim 1, wherein the polymer comprising a zwitterionic pendant group is the reaction product of monomers including one or more of an acrylate, a methacrylate, an acrylamide, or a methacrylamide.

9. The prosthetic heart valve of claim 1, wherein each leaflet comprises a plurality of fibers.

10. The prosthetic heart valve of claim 9, wherein the plurality of fibers are embedded in the base polymer, each fiber being oriented in an extending direction and comprising a plurality of undulations.

11. The prosthetic heart valve of claim 1, wherein the prosthetic heart valve comprises an expandable tubular body, wherein the expandable tubular body comprises a polymer layer comprising the same polymer as the base polymer of the plurality of leaflets.

12. The prosthetic heart valve of claim 1, wherein the base polymer comprises polyisobutylene polyurethanes (PIB-PUR).

13. A prosthetic heart valve comprising

a plurality of synthetic polymeric leaflets, each leaflet having a base polymer and a polymer coating disposed over the base polymer,

wherein the polymer coating comprises a trimethoxysilane functionalized polymer that is the reaction product of one or more monomers comprising zwitterionic pendant groups and one or more monomers comprising non-zwitterionic pendent groups.

14. The prosthetic heart valve of claim 13, wherein the polymer of the polymer coating is the reaction product of a monomer comprising zwitterionic pendant groups having a structure selected from the group consisting of:

15. A prosthetic heart valve comprising

a plurality of synthetic polymeric leaflets, each leaflet having a base polymer and a polymer coating disposed over the base polymer;

wherein the polymer coating comprises a polymer comprising zwitterionic pendant groups, wherein each zwitterionic pendant group comprises an anionic group and a cationic group; and

wherein the polymer of the polymer coating comprises the reaction product of one or more monomer species having a structure selected from the group consisting of;

16. The prosthetic heart valve of claim 15, wherein the polymer of the polymer coating is functionalized with a trimethoxysilane.