Polymers of fluorinated monomers and hydrophilic monomers

• US 7,244,443 B2
• Filed: 08/31/2004
• Issued: 07/17/2007
• Est. Priority Date: 08/31/2004
• Status: Active Grant

• Current Assignee: Advanced Cardiovascular Systems Incorporated (Abbott Laboratories)
• Original Assignee: Advanced Cardiovascular Systems Incorporated (Abbott Laboratories)
• Inventors: Pacetti, Stephen Dirk
• Primary Examiner(s): Wu; David W.
• Assistant Examiner(s): Hu; Henry S.
• Application Number:
  US10/931,927
• Publication Number:
  US 20060047095A1
• Time in Patent Office: 1,050 Days
• Field of Search: 524/520, 524/544, 424/423
• US Class Current: 424/423
• CPC Class Codes: A61L 2300/416 Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
• CPC Class Codes: A61L 2300/42 Anti-thrombotic agents, anticoagulants, anti-platelet agents
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: C08F 214/18 Monomers containing fluorine
• CPC Class Codes: C08F 214/22 Vinylidene fluoride
• CPC Class Codes: C08L 27/12 containing fluorine atoms
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]

Abstract

A polymer of fluorinated monomers and hydrophilic monomers is provided. It is also provided a polymer blend that contains a polymer of fluorinated monomers and another biocompatible polymer. The polymer of fluorinated monomers or polymer blend described herein and optionally a bioactive agent can form a coating on an implantable device such as a drug-delivery stent. The implantable device can be used for treating or preventing a disorder such as atherosclerosis, thrombosis, restenosis, hemorrhage, vascular dissection or perforation, vascular aneurysm, vulnerable plaque, chronic total occlusion, patent foramen ovale, claudication, anastomotic proliferation for vein and artificial grafts, bile duct obstruction, ureter obstruction, tumor obstruction, or combinations thereof.

Claims

1. A biocompatible copolymer comprising fluorinated monomers and hydrophilic monomers,

wherein the copolymer has a structure of formula I:

2. The biocompatible polymer of claim 1,

3. The biocompatible copolymer of claim 2,l wherein the flexibility monomer can be —

CF₂—

CRF—

, —

CHF—

CRF—

, and —

CF₂—

CRH—

, or combinations thereof in which R is selected from the group consisting of trifluoromethyl, F, Cl, Br, I, short chain alkyl groups from C₂ to C₁₂, fluorinated short chain alkyl groups from C₂ to C₁₂, and combinations thereof.

4. The biocompatible copolymer of claim 1, wherein the hydrophilic monomer is selected from the group consisting of vinyl pyrrolidone, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl vinyl ether, alkyl vinyl ether, vinyl alcohol, methacrylic acid, acrylic acid, acrylamide, N-alkyl acrylamide, hydroxypropylmethacrylamide, vinyl acetate, 2-sulfoethyl methacrylate, 3 -sulfopropyl acrylate, 3 -sulfopropyl methacrylate, PEG-methacrylate, 2-aminoethyl methacrylate hydrochloride, N-(3-aminopropyl)methacrylamide hydrochloride, 2-N-morpholinoethyl methacrylate, vinylbenzoic acid, vinyl sulfonic acid, styrene sulfonates, a monomer that bears a charge, and combinations thereof.

5. The biocompatible copolymer of claim 2, wherein the hydrophilicity monomer is selected from the group consisting of vinyl pyrrolidone, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl vinyl ether, alkyl vinyl ether, vinyl alcohol, methacrylic acid, acrylic acid, acrylamide, N-alkyl acrylamide, hydroxypropylmethacrylamide, vinyl acetate, 2-sulfoethyl methacrylate, 3-sulfopropyl acrylate, 3-sulfopropyl methacrylate, PEG-methacrylate, 2-aminoethyl methacrylate hydrochloride, N-(3-aminopropyl)methacrylamide hydrochloride, 2-N-morpholinoethyl methacrylate, vinylbenzoic acid, vinyl sulfonic acid, styrene sulfonates, a monomer that bears a charge, and combinations thereof.

6. The biocompatible copolymer of claim 2 having a structure of any of formulae II–

IV;

7. The biocompatible copolymer of claim 2, wherein the strength fluoro monomer is in the range from about 60 mole % to about 90 mole %,

wherein the flexibility fluoro monomer is in the range from above 0 mole % to about 40 mole %, and

wherein the hydrophilic monomer is in the range from above 0 mole % to about 20 mole %.