Bioabsorbable, biobeneficial polyester polymers for stent coatings

• US 7,301,001 B2
• Filed: 12/20/2006
• Issued: 11/27/2007
• Est. Priority Date: 06/11/2003
• Status: Expired due to Fees

• Current Assignee: Advanced Cardiovascular Systems Incorporated (Abbott Laboratories)
• Original Assignee: Advanced Cardiovascular Systems Incorporated (Abbott Laboratories)
• Inventors: Pacetti, Stephen D., Hossainy, Syed F. A.
• Primary Examiner(s): BOYKIN, TERRESSA M
• Application Number:
  US11/643,331
• Publication Number:
  US 20070100123A1
• Time in Patent Office: 342 Days
• Field of Search: 424/426, 427/22.25, 427 22-271, 427/272, 528/271, 528/272, 623/1.46, 623/1.47, 623/1.48
• US Class Current: 528/272
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 31/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: C08G 63/20 Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
• CPC Class Codes: C08G 63/668 derived from polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: C08G 63/6854 derived from polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: C08G 63/6886 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08L 2666/18 Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
• CPC Class Codes: C08L 2666/20 Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence
• CPC Class Codes: C08L 67/025 containing polyether sequences
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: C08L 69/00 Compositions of polycarbonates; Compositions of derivatives of polycarbonates
• CPC Class Codes: C08L 73/02 Polyanhydrides

Abstract

This disclosure covers polymers, some of which are useful in medical device applications. Some of these medical devices are implantable within a mammalian body, such as in a body lumen. The copolymers comprise at least one alcoholic moiety derived from a diol, triol, or polyol. Additionally, the copolymers comprise an acidic moiety, derived from a polycarboxylic acid, and a biobeneficial moiety. Some of these copolymers are biodegradable or bioerodable. Medical devices comprising these polymers and methods of making these polymers are within the scope of this disclosure.

Claims

1. A polymer comprising:

a) an alcoholic moiety derived from an aliphatic diol, triol, or polyol;

b) an acidic moiety derived from a polcarboxylic acid; and

c) a biobeneficial moiety derived from polypropylene glycol, PLURONIC™

surfactants, block copolymers comprising polyethylene glycol and polypropylene glycol, hydroxy functional poly(vinyl pyrrolidone), dextrin, sodium hyaluronate, hyaluronic acid, elastin, water-soluble heparin, water-soluble elastin, tropoelastin, poly(2-hydroxyethyl methylmethacrylate), heparin, hirudin, sulfonated polystyrene, superoxide dismutase mimetics, anti-oxidants, or free radical scavengers,

wherein the polycarboxylic acid is selected from the acidic moiety derived from at least one diacid selected from the group consisting of straight chain aliphatic diacids having 2 to 20 carbon atoms, terephthalic acid, fumaric acid, citric acid, citramalic acid, tricarballylic acid, tartaric acid, isophthalic acid, 1,6-bis(p-carboxy phenoxy)hexane, 1,3-bis(p-phenoxy carboxy)propane, 1,4-bis(p-phenoxy carboxy)butane, and oligomeric diacids with anhydride bonds in the backbone.

2. The polymer of claim 1 wherein the alcoholic moiety is derived from a diol having from 1 to 25 carbon atoms or a saccharide.

3. The polymer of claim 1 wherein the biobeneficial moiety is selected such that it gives rise to a released molecule that can pass through a mammalian kidney and that the released molecule has a molecular weight of less than or equal to 40,000 daltons.

4. A polymer comprising a block copolymer comprising at least three blocks wherein:

a) the first block comprises a block copolymer comprising;

i) a first-block alcoholic moiety derived from a di-, tri-, or poly-ol; and

ii) a first-block acidic moiety derived from a di-, tri-, or poly-acidic carboxylic acid;

b) the second block comprises a block copolymer comprising;

i) a second-block alcoholic moiety derived from a di-, tri-, or poly-ol; and

ii) a second-block acidic moiety derived from a di-, tri-, or poly-acidic carboxylic acid; and

c) the third block comprising a block copolymer comprising;

i) a third-block alcoholic moiety derived from a di-, tri-, or poly-ol; and

ii) a third-block acidic moiety derived from a di-, tri-, or poly-acidic carboxylic acid,

wherein at least one of the first- or second-block alcoholic moieties or first- or second-block acidic moieties is attached to a biobeneficial moiety derived from polypropylene glycol, PLURONIC™

surfactants, block copolymers comprising polyethylene glycol and polypropylene glycol, hydroxy functional poly(vinyl pyrrolidone), dextrin, sodium hyaluronate, hyaluronic acid, elastin, water-soluble heparin, water-soluble elastin, tropoelastin, poly(2-hydroxyethyl methylmethacrylate), heparin, hirudin, sulfonated polystyrene, superoxide dismutase mimetics, anti-oxidants, or free radical scavengers.