Biologically beneficial coatings for implantable devices containing fluorinated polymers and methods for fabricating the same

• US 9,114,198 B2
• Filed: 11/19/2003
• Issued: 08/25/2015
• Est. Priority Date: 11/19/2003
• Status: Expired due to Fees

• Current Assignee: Advanced Cardiovascular Systems Incorporated (Abbott Laboratories)
• Original Assignee: Advanced Cardiovascular Systems Incorporated (Abbott Laboratories)
• Inventors: Hossainy, Syed F. A., Tang, Yiwen
• Primary Examiner(s): CHANNAVAJJALA, LAKSHMI SARADA
• Application Number:
  US10/718,278
• Publication Number:
  US 20050106204A1
• Time in Patent Office: 4,297 Days
• US Class Current: 1/1
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: C08L 101/04 containing halogen atoms
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence
• CPC Class Codes: C08L 71/02 Polyalkylene oxides

Abstract

Coatings for an implantable medical device and a method of fabricating the coatings are disclosed. The coatings comprise a fluorinated polymer and a biologically beneficial polymer, an example of which includes poly(ethylene-glycol)-block poly(butylene terephthalate)-block poly(ethylene-glycol). A biologically active agent can be additionally conjugated to the biologically beneficial polymer.

Claims

1. A medical article comprising a coating disposed on at least a portion of an implantable medical device, the coating comprising:

(a) a fluorinated polymer; and

(b) a biologically beneficial polymer;

wherein the fluorinated polymer is selected from the group consisting of;

(i) products of polymerization of fluorinated olefins;

(ii) fluorine-containing cyclic polymers having a main chain with an asymmetrical cyclic structure selected from a group consisting of polymers of repeating units of cyclically polymerized perfluorallyl vinyl ether, perfluorobutenyl vinyl ether, and a combination thereof;

and

(iii) copolymers of perfluoro-2,2-dimethyl-1,3-dioxole with perfluoroolefins or with perfluoro(alkyl vinyl)ethers;

wherein the biologically beneficial polymer is selected from the group consisting of poly(ester amide) polymers of a general formula

-[M-P]_m-[M-Q]_n-, and combinations of these poly(ester amide) polymers,

wherein M is a moiety represented by the structure

2. The medical article of claim 1, wherein the implantable medical device is a stent.

3. The medical article of claim 1, wherein the fluorinated polymer is selected from the group consisting of products of polymerization of fluorinated olefins, and combinations of these polymers.

4. The medical article of claim 1, wherein the fluorinated polymer is selected from the group consisting of copolymers of perfluoro-2,2-dimethyl-1,3-dioxole with perfluoroolefins or with perfluoro(alkyl vinyl)ethers, and combinations of these polymers.

5. The medical article of claim 1, wherein the fluorinated polymer is selected from the group consisting of polymers of repeating units of cyclically polymerized perfluorallyl vinyl ether, perfluorobutenyl vinyl ether, and combinations of these polymers.

6. The medical article of claim 1, wherein the biologically active agent is selected from the group consisting of polyarginine, cRGD peptide, antisense agent Rensten-NG, rapamycin, everolimus (40-O-(2-hydroxy)ethyl-rapamycin), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, diazenium diolates, and combinations thereof.

7. The medical article of claim 6, wherein the diazenium diolates are selected from the group consisting of 1,3-propanediamine, N-{4-[1-(3-aminopropyl)-2-hydroxy-2-nitrosohydrazino]butyl}-diazen-1-ium-1,2-diolate (SDD), 1-{N-methyl-N-[6-(N-methylammonio)hexyl]amino}diazen-1-ium-1,2-diolate (MAHMA-NO), Z-1-[N-(2-aminoethyl)-N-(2-ammonioethyl)amino]diazen-1-ium-1,2-diolate (DETA-NO), and combinations thereof.

8. The medical article of claim 1, wherein the coating comprises two or more layers, the fluorinated polymer and the biobeneficial polymer being in separate layers, and the outermost layer comprising the biobeneficial polymer.

9. The medical article of claim 1, wherein the biologically active agent is selected from the group consisting of rapamycin, everolimus (40-O-(2-hydroxy)ethyl-rapamycin), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, and combinations thereof.

10. The medical article of claim 9, wherein the outermost layer of the coating covers the entire surface area of the implantable device.

11. The medical article of claim 1, wherein the Z of the poly(ester amide) polymers is poly(ethylene glycol).

12. The medical article of claim 1, wherein the Z of the poly(ester amide) polymers is poly(propylene glycol).

13. The medical article of claim 1, wherein the Z of the poly(ester amide) polymers is hyaluronic acid.

14. The medical article of claim 1, wherein the Z of the poly(ester amide) polymers is poly(2-hydroxyethyl methacrylate).