Source: http://www.google.co.uk/patents/US20100152402
Timestamp: 2017-10-23 12:00:20
Document Index: 365146957

Matched Legal Cases: ['Application No. 60', 'Application No. 60', 'Application No. 60', 'Application No. 60', 'Application No. 60', 'Application No. 60', 'Application No. 60']

Patent US20100152402 - Zwiterionic terpolymers, method of making and use on medical devices - Google Patents
Biocompatible terpolymers are manufactured to include a zwitterionic monomer, an alkoxy acrylate monomer, and a hydrophobic monomer....http://www.google.co.uk/patents/US20100152402?utm_source=gb-gplus-sharePatent US20100152402 - Zwiterionic terpolymers, method of making and use on medical devices
Publication number US20100152402 A1
Application number US 12/711,082
Also published as US7713541, US8431665, US8722826, US20130296513
Publication number 12711082, 711082, US 2010/0152402 A1, US 2010/152402 A1, US 20100152402 A1, US 20100152402A1, US 2010152402 A1, US 2010152402A1, US-A1-20100152402, US-A1-2010152402, US2010/0152402A1, US2010/152402A1, US20100152402 A1, US20100152402A1, US2010152402 A1, US2010152402A1
Patent Citations (100), Referenced by (5), Classifications (12), Legal Events (4)
US 20100152402 A1
1. A biocompatible polymer, comprising:
2. A biocompatible polymer as in claim 1, in which the zwitterion group is selected from the group consisting of phosphorylcholine, phosphoryl ethanolamine, phosphatidyl ethanolamine, phosphoethanolamine, phosphatidyl serine, sulfobetaine and combinations thereof.
3. A biocompatible polymer as in claim 1, in which R6 is selected from the group consisting of a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-ethyl-hexyl, n-hexyl, cyclohexyl, n-hexyl, isobornyl, or trimethylcyclohexyl, and combinations thereof.
4. A biocompatible polymer as in claim 1, in which R5 is a methyl.
5. A biocompatible polymer as in claim 1, in which R5 is an ethyl.
6. A biocompatible polymer as in claim 1, in which the glass transition temperature of the polymer when hydrated is in a range from about −30° C. to about 37° C.
7. A biocompatible polymer as in claim 1, in which the glass transition temperature of the polymer when hydrated is in a range from about 0° C. to about 37° C.
8. A biocompatible polymer as in claim 1, in which the glass transition temperature of the polymer when dry is in a range from about −30° C. to about 100° C.
9. A biocompatible polymer as in claim 1, in which the glass transition temperature of the polymer when dry is in a range from about 0° C. to about 70° C.
10. A biocompatible polymer as in claim 1, in which the number average molecular weight is in a range from about 20K to about 800K.
11. A biocompatible polymer as in claim 1, in which the number average molecular weight is in a range from about 100K to about 600K.
12. A biocompatible polymer as in claim 1, in which the number average molecular weight is in a range from about 2K to about 200K.
This application is divisional application of U.S. application Ser. No. 11/939,512, filed Nov. 13, 2007, the teaching of which is incorporated herein in its entirety by reference. U.S. application Ser. No. 11/939,512 is a non-provisional application of U.S. provisional No. 60/866,805, filed on Nov. 21, 2006. This application is also a continuation-in-part of co-pending U.S. application Ser. No. 11/562,338 entitled “Use of Terpolymer of Tetrafluoroethylene, Hexafluoropropylene, and Vindylidene Fluoride in Drug Eluting Coatings on Medical Devices”, filed on Nov. 21, 2007. This application also claims priority to U.S. Provisional Patent Application No. 60/866,800, entitled “Copolymers Having Zwitterionic Moieties And Dihydroxyphenyl Moieties And Medical Devices Coated With The Copolymers”, U.S. Provisional Patent Application No. 60/866,802, entitled “Methods of Manufacturing Copolymers with Zwitterionic Moieties and Dihydroxyphenyl Moieties and Use of Same”, U.S. Provisional Patent Application No. 60/866,804, entitled “Zwitterionic Copolymers, Method of Making and Use on Medical Devices”, U.S. Provisional Patent Application No. 60/866,798, entitled “Amino Acid Mimetic Copolymers and Medical Devices Coated with the Copolymers”, co-pending U.S. Provisional Patent Application No. 60/866,797, entitled “Methods for Manufacturing Amino Acid Mimetic Copolymers and Use of Same”, U.S. Provisional Patent Application No. 60/866,796, entitled “Copolymers Having 1-Methy1-2-Methoxyethyl Moieties”, and U.S. Provisional Patent Application No. 60/866,792, entitled “Methods for Manufacturing Copolymers Having 1-methy1-2-Methoxyethyl Moieties and Use of Same”, each of which was filed Nov. 21, 2006, and each of which is hereby incorporated by reference in their entirety.
Embodiments of the invention relate to zwitterionic terpolymers. More particularly, embodiments of the invention relate to terpolymers of zwitterionic monomers, alkoxy acrylate monomers, and alkyl acrylate monomers and methods of making and using the terpolymers. 2. The Related Technology
Alternatively, the zwitterionic group may be a betaine group (i.e., in which the cation is closer to the backbone), for instance a sulpho-, carboxy- or phosphor-betaine. In an embodiment, the betaine group has the formula —A4—R3N+(R4)2—R5-V−, in which A4 is a valence bond, —O—, —S—, or —NH—; V is a carboxylate, sulphonate or phosphate diester (monovalently charged) anion; R3 is a valence bond (together with A4) or alkanediyl, —C(O)alkylene— or —C(O)NH alkylene; the groups R4 are the same or different and each is hydrogen or alkyl of 1 to 4 carbon atoms or the groups R4 together with the nitrogen to which the are attached form a heterocyclic ring of 5 to 7 atoms; and R5 is an alkyanediyl of 1 to 20 carbon atoms; of 1 to 10 carbon atoms, or of 1 to 6 carbon atoms.
In the foregoing formula, A5 is a valence bond, —O—, —S—, or —NH—; R16 is a valence bond (optionally together with A5) or alkanediyl, —C(O)alkylene— or —C(O)NH alkylene; the groups R17 are the same or different and each is hydrogen or alkyl of 1 to 4 carbon atoms or the groups R4 together with the nitrogen to which the are attached form a heterocyclic ring of 5 to 7 atoms; and R5 is an alkyanediyl of 1 to 20 carbon atoms, of 1 to 10 carbon atoms, or of 1 to 6 carbon atoms.
As can be seen, the PMEA coating is the most hemocompatible of the polymers tested. Kocakular et al. investigated the blood compatibility of PMEA coated extracorporeal circuits (Kocakular M., et al., J Bioactive and Compatible Polymers Vol. 17, Sept. 2002, p. 343). Hollow fiber oxygenators coated with PMEA were evaluated during twenty clinical procedures requiring cardiopulmonary bypass. The operations were compared to twenty operations with uncoated hollow fiber oxygenators. PMEA coatings were found to reduce both platelet adhesion and fibrinogen/albumin absorption. A coating of PEMA, known as the X coating®, is used in the CAPIOX RX blood oxygenator sold by Terumo.
The polymer coatings can be applied to a medical device using any techniques known to those skilled in the art or those that may be developed for applying a coating to a medical device. Examples of suitable techniques for applying the coating to the medical device include spraying, dip coating, roll coating, spin coating, powder coating, and direct application by brush or needle. One skilled in the art would appreciate the many diffetent techniques used in powder coating and apply them to the embodiments of the invention. The copolymers can be applied directly to the surface of the implant device, or they can be applied over a primer or other coating material.
FIG. 1A shows an example scent 10 coated with a polymer including zwitteionic monomers and alkyl acrylate monomers. Stent 10 includes a generally tubular body 12 with a lumen. The struts of body 12 (e.g. strut 14) provide a supporting structure for coating the polymers of the invention.
Examples of suitable bioactive agents include synthetic inorganic and organic compounds, proteins and peptides, polysaccharides and other sugars, lipids, DNA and RNA nucleic acid sequences, antisense oligonucleotides, antibodies, receptor ligands, enzymes, adhesion peptides, blood clot agents, including streptokinase and tissue plasminogen activator, antigens, hormones, growth factors, ribozymes, retroviral vectors, anti-proliferative agents including rapamycin (sirolimus), 40-O-(2-hydroxyethyDrapamycin (everolimus), 40-O-(3-hydroxypropyl)rapamycin, 40-O-(2-hydroxyethyoxy)ethylrapamycin, 40-O-tetrazolylrapamycin (zotarolimus, ABT-578), paclitaxel, docetaxel, methotrexate, azathioprine, vincristine, vinblastine, fluorouracil, doxorubicin hydrochloride, mitomycin, antiplatelet compounds, anticoagulants, antifibrin, antithrombins including sodium heparin, low molecular weight heparins, heparinoids, hirudin, argatroban, forskolin, vapiprost, prostacyclin, prostacyclin analogues, dextran, D-phe-pro-arg-chloromethylketone (synthetic antithrombin), dipyridamole, glycoprotein IIb/IIIa platelet membrane receptor antagonist antibody, recombinant hirudin, thrombin inhibitors including Angiomax A, calcium channel blockers including nifedipine, colchicine, fibroblast growth factor (FGF) antagonists, fish oil (omega 3-fatty acid), histamine antagonists, lovastatin, monoclonal antibodies, nitroprusside, phosphodiesterase inhibitors, prostaglandin inhibitors, suramin, serotonin blockers, steroids, thioprotease inhibitors, triazolopyrimidine, nitric oxide or nitric oxide donors, super oxide dismutases, super oxide dismutase mimetic, estradiol, anticancer agents, dietary supplements including vitamins, anti-inflammatory agents including aspirin, tacrolimus, dexamethasone and clobetasol, cytostatic substances including angiopeptin, angiotensin converting enzyme inhibitors including captopril, cilazapril or lisinopril, antiallergic agents is permirolast potassium, alpha-interferon, bioactive RGD, and genetically engineered epithelial cells. Other bioactive agents which are currently available or that may be developed in the future for use with DESs may likewise be used and all are within the scope of this invention.
US7048975 * 2 Oct 2000 23 May 2006 Kao Corporation Pulp molded container
US8202956 * 10 Mar 2011 19 Jun 2012 Abbott Laboratories Copolymers having zwitterionic moieties and dihydroxyphenyl moieties and medical devices coated with the copolymers
US20040152785 * 7 Sep 2001 5 Aug 2004 Shigehiro Okuyama Novel crystal of n-hydroxy-2 (s)-methyl-5-ethoxymethoxy-4(s)-[n-(4-phenoxyphenylcarbonyl)amino] pentanamide, process for their production and medicines containing the crystals as the active ingredient
US20100160391 * 9 Jul 2007 24 Jun 2010 Hammock Bruce D Substituted Aminopyridines as Fluorescent Reporters for Amide Hydrolases
US20120157602 * 23 Feb 2012 21 Jun 2012 Abbott Laboratories Copolymers having zwitterionic moieties and dihdroxyphenyl moieties and medical devices coated with the copolymers
WO2000056283A1 * 17 Mar 2000 28 Sep 2000 The B.F.Goodrich Company Inhibition of matrix metalloproteinases with polymers and pharmaceutical applications thereof
U.S. Classification 526/277
Cooperative Classification C08F2220/282, C08F230/02, C09D133/14, A61F2/91, A61L27/34, A61L31/10, C08F2220/1825
European Classification A61L31/10, A61L27/34, C09D133/14
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:PACETTI, STEPHEN;ROORDA, WOUTER ERIK;SIGNING DATES FROM 20080107 TO 20080116;REEL/FRAME:028451/0767