Bioabsorbabl, biobeneficial polyester polymers for stent coatings
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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.
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Citations
42 Claims
- 1. A polymer with the following formula:
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2. A medical device comprising a polymer comprising:
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a) an alcoholic moiety derived from an aliphatic diol, triol, or polyol; b) an acidic moiety derived from a polycarboxylic 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. - View Dependent Claims (3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13)
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17. A medical device comprising a block copolymer comprising at least two blocks wherein:
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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; and 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 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. - View Dependent Claims (18, 19, 20, 21, 22, 23, 24, 25, 26, 27)
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35. A polymer with the following formula:
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36. A polymer comprising:
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an alcoholic moiety derived from an aliphatic diol having from 1 to 25 carbon atoms or a saccharide; an acidic moiety derived from a polycarboxylic acid; and a biobeneficial moiety is 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.
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37. A polymer comprising:
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an alcoholic moiety derived from an aliphatic diol, triol, or polyol; an acidic moiety derived from a polycarboxylic acid; and a biobeneficial moiety having biobeneficial characteristics, a non-fouling moiety having non-fouling characteristics, a bioactive moiety having bioactive characteristics, or a moiety that has any combination of biobeneficial, non-fouling, or bioactive characteristics, wherein the biobeneficial moiety is 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, andwherein the polycarboxylic acid is selected from the acidic moiety is 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.
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38. A polymer comprising:
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an alcoholic moiety derived from an aliphatic diol, triol, or polyol; an acidic moiety derived from a polycarboxylic acid; and a biobeneficial moiety is 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 having a molecular weight of less than or equal to 40,000 daltons,wherein the polycarboxylic acid is selected from the acidic moiety is 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.
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39. A block copolymer comprising at least two blocks wherein:
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a) the first block comprises a block copolymer comprising; i) a first-block alcoholic moiety independently derived from at least one of ethylene glycol, 1,2-propane diol, 1,3-propane diol, 1,4-butanediol, 1,5-butanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, higher diols up to C16, glycerol, trimethylol propane, pentaerythritol, cyclohexanedimethanol, serinol, diethanolamine, or saccharides; and ii) a first-block acidic moiety derived from a di-, tri-, or poly-acidic carboxylic acid; and b) the second block comprises a block copolymer comprising; i) a second-block alcoholic moiety independently derived from at least one of ethylene glycol, 1,2-propane diol, 1,3-propane diol, 1,4-butanediol, 1,5-butanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, higher diols up to C16, glycerol, trimethylol propane, pentaerythritol, cyclohexanedimethanol, serinol, diethanolamine, or saccharides; and ii) a second-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, andwherein the first- or second-block acidic moieties are derived from at least one of straight chain aliphatic diacids having 2 to 20 carbon atoms. - View Dependent Claims (40)
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41. A composition comprising:
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a first polymer, wherein the first polymer comprises polycaprolactone, poly(D,L-lactide), poly(L-lactide), poly(D,L-lactide-co-L-lactide), poly(glycolide), poly(D,L-lactide-co-glycolide), poly(dioxanone), poly(4-hydroxybutyrate), poly(3-hydroxybutyrate), poly(3-hydroxy valerate), poly(hydroxybutyrate-co-hydroxyvalerate), poly(tyrosine derive carbonates), poly(tyrosine arylates), poly(imino carbonates), poly(trimethylene carbonate), poly(anhydrides), poly(orthoesters), or poly(ester amides), blended with a second polymer, wherein the second polymer comprises an alcoholic moiety derived from an aliphatic diol, triol, or polyol; an acidic moiety derived from at least one of straight chain aliphatic diacids having 2 to 20 carbon atoms; and 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. - View Dependent Claims (42)
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Specification