Polymers of fluorinated monomers and hydrophilic monomers

• US 7,766,884 B2
• Filed: 05/25/2007
• Issued: 08/03/2010
• Est. Priority Date: 08/31/2004
• Status: Expired due to Fees

• Current Assignee: Advanced Cardiovascular Systems Incorporated
• Original Assignee: Advanced Cardiovascular Systems Incorporated
• Inventors: Pacetti, Stephen Dirk
• Primary Examiner(s): Mulcahy; Peter D.
• Assistant Examiner(s): HU, HENRY S
• Application Number:
  US11/807,091
• Publication Number:
  US 20070228345A1
• Time in Patent Office: 1,166 Days
• Field of Search: 604/265, 424/423, 524/520, 524/544
• US Class Current: 604/265
• 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 blend that contains a polymer of fluorinated monomers and another biocompatible polymer. The polymer blend can form a coating on a medical device. The medical device can be used for treat, prevent or ameliorate a medical condition.

Claims

1. An implantable device having a coating thereon, wherein the coating comprises a biocompatible copolymer comprising fluorinated monomers and hydrophilic monomers,

wherein the copolymer has a structure of formula I:

2. The implantable device of claim 1, wherein the strength fluoro monomer is selected from the group consisting of —

CF₂—

CF₂—

, —

CH₂—

CF₂—

, —

CH₂—

CHF—

, —

CF₂—

CHF—

, —

CHF—

CHF—

, or —

CF₂—

CRF—

where R can be phenyl, cyclic alkyl, heterocyclic, heteroaryl, fluorinated phenyl, fluorinated cyclic alkyl, or fluorinated heterocyclic,

wherein the flexibility fluoro monomer is selected from substituted fluorinated ethylene monomers that bear a substituent,

wherein the hydrophilic monomer is selected from the group consisting of vinyl monomers that bear a pyrrolidone group(s), carboxylic acid group(s), sulfonic acid group(s), sulfone group(s), amino group(s), alkoxy group(s), amide group(s), ester group(s), acetate group(s), poly(ethylene glycol) group(s), poly(propylene glycol) group(s), poly(tetramethylene glycol) group(s), poly(alkylene oxide) group(s), hydroxyl group(s), or a substituent that contains a charge or one of pyrrolidone group(s), carboxylic acid group(s), sulfone group(s), sulfonic acid group(s), amino group(s), alkoxy group(s), amide group(s), ester group(s), acetate group(s), poly(ethylene glycol) group(s), poly(propylene glycol) group(s), poly(tetramethylene glycol) group(s), poly(alkylene oxide) group(s), hydroxyl group(s), and combinations thereof.

3. The implantable device of claim 2, 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 implantable device 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 implantable device 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 implantable device of claim 1, wherein the biocompatible polymer has a structure of any of formula II and Formula IV:

7. The implantable device 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 %.

8. The implantable device of claim 1, further comprising a bioactive agent.

9. The implantable device of claim 8, wherein the bioactive agent is selected from the group consisting of paclitaxel, docetaxel, estradiol, nitric oxide donors, super oxide dismutases, super oxide dismutases mimics, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), tacrolimus, dexamethasone, rapamycin, rapamycin derivatives, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, and 40-O-tetrazole-rapamycin, ABT-578, clobetasol, prodrugs thereof, co-drugs thereof, and a combination thereof.

10. The implantable device of claim 1, which is a stent.

11. The implantable device of claim 8, which is a stent.

12. The implantable device of claim 9, which is a stent.