Source: https://patents.google.com/patent/US8431665B2/en
Timestamp: 2018-10-17 12:55:50
Document Index: 767561889

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

US8431665B2 - Zwitterionic terpolymers, method of making and use on medical devices - Google Patents
US8431665B2
US8431665B2 US12711082 US71108210A US8431665B2 US 8431665 B2 US8431665 B2 US 8431665B2 US 12711082 US12711082 US 12711082 US 71108210 A US71108210 A US 71108210A US 8431665 B2 US8431665 B2 US 8431665B2
US12711082
US20100152402A1 (en )
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 Nos. 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”, 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-Methyl-2-Methoxyethyl Moieties”, and U.S. Provisional Patent Application No. 60/866,792, entitled “Methods for Manufacturing Copolymers Having 1-methyl-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.
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.
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, Sep. 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.
m is a mole fraction in a range from about 0.1 to about 0.99,
o is a mole fraction in a range from about 0.1 to about 0.99, and m+n+o=1.
US12711082 2006-11-21 2010-02-23 Zwitterionic terpolymers, method of making and use on medical devices Expired - Fee Related US8431665B2 (en)
US11939512 Division US7713541B1 (en) 2006-11-21 2007-11-13 Zwitterionic terpolymers, method of making and use on medical devices
US13863261 Continuation US8722826B2 (en) 2006-11-21 2013-04-15 Zwitterionic terpolymers, method of making and use on medical devices
US20100152402A1 true US20100152402A1 (en) 2010-06-17
US8431665B2 true US8431665B2 (en) 2013-04-30
Gisselfalt et al. "Effect of Soft Segment Length and Chain Extender Structure on Phase Separation and Morphology in Poly (urethane urea)s", Macromol. Mater. Eng. No. 3, 288: pp. 265-271 (2003).
Hull et al. THV Fluoroplastic in Modern Fluoropolymers Ed. J. Scheirs p. 257 (1997).
Peck, "TCT: New Definition and Data Make Drug-Eluting Coronary Stents Seem Safer", MedPage Today (Oct. 24, 2006), available at www.medpagetoday.com/Cardiology/PCl/4355 (last accessed Oct. 15, 2012), 2 pgs.
Solvay Solexis 'Tecnoflon® P757 product information, 10 pgs. (2003).
Tanaka et al., "Blood compatible aspects of poly(2- methoxyethylacrylate) (PMEA)-relationship between protein adsorption and platelet adhesion on PMEA surface", Biomaterials 21, pp. 1471-1481 (2000).
U.S. Appl. No. 11/899,740, filed Sep. 6, 2007, Hosainy et al.