CA2570322A1 - Side-chain crystallizable polymers for medical applications - Google Patents

Side-chain crystallizable polymers for medical applications Download PDF

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Publication number
CA2570322A1
CA2570322A1 CA002570322A CA2570322A CA2570322A1 CA 2570322 A1 CA2570322 A1 CA 2570322A1 CA 002570322 A CA002570322 A CA 002570322A CA 2570322 A CA2570322 A CA 2570322A CA 2570322 A1 CA2570322 A1 CA 2570322A1
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polymer
medical device
group
polymeric material
crystallizable
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CA002570322A
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CA2570322C (en
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Donald K. Brandom
Joan Zeltinger
Eric V. Schmid
Joseph J. Mallon
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Reva Medical Inc
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Reva Medical, Inc.
Donald K. Brandom
Joan Zeltinger
Eric V. Schmid
Joseph J. Mallon
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    • C08G64/04Aromatic polycarbonates
    • C08G64/06Aromatic polycarbonates not containing aliphatic unsaturation
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    • A61B17/12181Occluding by internal devices, e.g. balloons or releasable wires characterised by the type of occluding device formed by fluidized, gelatinous or cellular remodelable materials, e.g. embolic liquids, foams or extracellular matrices
    • A61B17/12186Occluding by internal devices, e.g. balloons or releasable wires characterised by the type of occluding device formed by fluidized, gelatinous or cellular remodelable materials, e.g. embolic liquids, foams or extracellular matrices liquid materials adapted to be injected
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    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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    • C08G63/682Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
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    • C08G63/685Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
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    • C08G65/40Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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    • A61B17/00Surgical instruments, devices or methods, e.g. tourniquets
    • A61B17/12Surgical instruments, devices or methods, e.g. tourniquets for ligaturing or otherwise compressing tubular parts of the body, e.g. blood vessels, umbilical cord
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    • C08G2261/10Definition of the polymer structure
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    • C08G2261/126Copolymers block

Abstract

Inherently radiopaque side-chain crystallizable polymers (IRSCCP's) are useful in various medical applications. An example of a IRSCCP is a polymer that comprises a main chain, a plurality of crystallizable side chains, and a plurality of heavy atoms attached to the polymer, the heavy atoms being present in an amount that is effective to render the polymer radiopaque. A
polymeric material that includes a IRSCCP may be fabricated into a medical device useful for at least partially occluding a body cavity. For example, such a medical device may be an embolotherapy product.

Claims (75)

1. A polymer comprising:
a main chain;

a plurality of crystallizable side chains; and a plurality of heavy atoms attached to the polymer, the heavy atoms being present in an amount that is effective to render the polymer radiopaque.
2. The polymer of Claim 1 having a melting point in the range of about 30°C to about 80°C.
3. The polymer of Claim 1 that is biocompatible.
4. The polymer of Claim 1 that is bioresorbable.
5. The polymer of Claim 1 in which the plurality of heavy atoms comprise an atom having an atomic number of at least 17.
6. The polymer of Claim 5 in which the plurality of heavy atoms comprise an atom having an atomic number of at least 35.
7. The polymer of Claim 1 in which the plurality of heavy atoms comprise an atom selected from the group consisting of bromine, iodine, bismuth, gold, platinum tantalum, tungsten, and barium.
8. The polymer of Claim 1 in which the plurality of heavy atoms are covalently attached to the polymer.
9. The polymer of Claim 1 in which the plurality of heavy atoms are ionically attached to the polymer.
10. The polymer of Claim 1 that is a copolymer comprising at least two different recurring units.
11. The polymer of Claim 10 that is a random copolymer.
12. The polymer of Claim 10 that is a block copolymer.
13. The polymer of Claim 1 in which the heavy atoms are attached to the polymer in a manner that minimizes disruption of side chain crystallinity.
14. The polymer of Claim 1 that comprises a recurring unit of the formula (I):

(I) wherein:

X1 and X2 are each independently selected from the group consisting of Br and I;

y1 and y2 are each independently zero or an integer in the range of 1 to 4;
A1 is selected from the group consisting of R3 is selected from the group consisting of C1-C30 alkyl, C1-C30 heteroalkyl, C5-C30 aryl, C6-C30 alkylaryl, and C2-C30 heteroaryl;
R4 selected from the group consisting of H, C1-C30 alkyl, and C1-C30 heteroalkyl;
R1 is Z is O or S;
R5 and R6 are each independently selected from the group consisting of -CH=CH-, -CHJ1-CHJ2-, and -(CH2)n-;
a is zero or an integer in the range of 1 to 8;
J1 and J2 are each independently selected from the group consisting of Br and I; and Q is a crystallizable group comprising from about 6 to about 30 carbon atoms.
15. The polymer of Claim 14 in which Q comprises from about 20 to about 30 carbon atoms.
16. The polymer of Claim 14 in which R5 is -CH=CH- or -(CH2)n-; R6 is -(CH2)a-; and Q is an ester group comprising from about 10 to about 30 carbon atoms.
17. The polymer of Claim 1 that comprises a recurring unit of the formula (II):
wherein R7 is H or CH3; A3 is a chemical group having a molecular weight of about 500 or less; and A3 bears at least one of the heavy atoms attached to the polymer.
18. The polymer of Claim 17 in which A3 comprises a metal carboxylate or metal sulfonate.
19. The polymer of Claim 18 in which A3 comprises barium.
20. The polymer of Claim 17 in which A3 comprises an ester or amide linkage.
21. The polymer of Claim 17 in which A3 comprises an aromatic group bearing at least one halogen atom selected from the group consisting of bromine and iodine.
22. The polymer of Claim 17 in which A3 comprises a chemical group of the formula -L1-(CH2)n2-L2-Ar1, wherein L1 and L2 each independently represent a nullity, ester, ether or amide group; n2 is zero or an integer in the range of about 1 to about 30; and Ar1 comprises a halogenated aromatic group containing from about 2 to about 20 carbon atoms.
23. The polymer of Claim 17 that comprises a second recurring unit, the second recurring unit comprising at least one of the crystallizable side chains.
24. The polymer of Claim 23 in which the second recurring unit is of the formula (III):

wherein R8 is H or CH3; L3 is an ester or amide linkage; and R9 comprises a C6 to C30 hydrocarbon group.
25. The polymer of Claim 1 that comprises a recurring unit of the formula (IV):
wherein A4 represents H or a chemical group containing from about 1 to about 30 carbons; A3 is a chemical group having a molecular weight of about 500 or less; and A3 bears at least one of the heavy atoms attached to the polymer.
26. The polymer of Claim 25 in which A3 comprises an aromatic group bearing it least one halogen atom selected from the group consisting of bromine and iodine.
27. The polymer of Claim 25 that comprises a second recurring unit, the second recurring unit comprising at least one of the crystallizable side chains.
28. The polymer of Claim 27 in which the second recurring unit is of the formula (V):

wherein R10 comprises a C6 to C30 hydrocarbon group and R11 represents H
or a C1 to C30 hydrocarbon group.
29. A medical device that comprises the polymer of Claim 1.
30. The medical device of Claim 29 that further comprises an effective amount of at least one therapeutic agent.
31. A medical device that comprises a polymeric material, the polymeric material comprising a biocompatible inherently radiopaque side chain crystallizable polymer.
32. The medical device of Claim 31 in which the polymeric material comprises a second polymer in admixture with the inherently radiopaque polymer.
33. The medical device of Claim 31 in which the inherently radiopaque polymer is bioresorbable.
34. The medical device of Claim 31 that is configured to be deliverable to a body cavity of a mammal.
35. The medical device of Claim 34 that is configured to be deliverable by injection or by catheter.
36. The medical device of Claim 34 that comprises an embolotherapy product, the embolotherapy product comprising at least a portion of the inherently radiopaque polymer.
37. The medical device of Claim 36 in which at least a portion of the inherently radiopaque polymer in the embolotherapy product is formed into at least one configuration selected from the group consisting of a rod, a particle, or a sheet.
38. The medical device of Claim 37 in which the rod is in the form of a coil.
39. The medical device of Claim 38 in which the coil is a memory coil.
40. The medical device of Claim 37 in which the particle is selected from the group consisting of a spherical particle, a geometrically non-uniform particle, a porous particle, a hollow particle, a solid particle, and a particle having an excluded diameter of from about 10 microns to about 5,000 microns.
41. The medical device of Claim 40 in which the geometrically non-uniform particle is a flake or a chip.
42. The medical device of Claim 34 in which the polymeric material has a melting point in the range of about 30°C to about 80°C.
43. The medical device of Claim 42 in which the polymeric material is configured to flow at a temperature above the melting point.
44. The medical device of Claim 43 in which the polymeric material has a viscosity in the range of about 50 cP to about 500 cP at the temperature above the melting point.
45. The medical device of Claim 43 in which the polymeric material has a viscosity in the range of about 500 cP to about 5,000 cP at the temperature above the melting point.
46. The medical device of Claim 43 in which the polymeric material has a viscosity in the range of about 5,000 cP to about 250,000 cP at the temperature above the melting point.
47. The medical device of Claim 43 in which the polymeric material has a viscosity in the range of about 250,000 cP to about 1,000,000 cP at the temperature above the melting point.
48. The medical device of Claim 43 in which the polymeric material comprises a crystalline region and a non-crystalline region at a temperature below the body temperature of the mammal.
49. The medical device of Claim 48 in which the non-crystalline region has a glass transition temperature that is higher than the body temperature.
50. The medical device of Claim 48 in which the non-crystalline region has a glass transition temperature that is lower than the body temperature.
51. The medical device of Claim 43 in which the polymeric material is configured to form a solid mass upon delivery to the body cavity, the solid mass at least partically conforming to an interior dimension of the body cavity.
52. The medical device of Claim 51 in which the polymeric material comprises an excipient selected from the group consisting of a photopolymerizable material, a blood reactive substance and a nucleating agent.
53. The medical device of Claim 51 in which the solid mass retains a preformed shape.
54. The medical device of Claim 53 in which the preformed shape is a coil.
55. The medical device of Claim 31 that further comprises an effective amount of at least one therapeutic agent.
56. The medical device of Claim 55 in which the therapeutic agent is selected from the group consisting of a chemotherapeutic agent, a non-steroidal anti-inflammatory, a steroidal anti-inflammatory, and a wound healing agent.
57. The medical device of Claim 55 in which the therapeutic agent is selected to promote at least one biological response.
58. The medical device of Claim 57 in which the biological response is selected from the group consisting of thrombosis, cell attachment, cell proliferation, attraction of inflammatory cells, deposition of matrix proteins, inhibition of thrombosis, inhibition of cell attachment, inhibition of cell proliferation, inhibition of inflammatory cells, and inhibition of deposition of matrix proteins.
59. The medical device of Claim 55 in which at least a portion of the therapeutic agent is contained within the polymeric material.
60. The medical device of Claim 59 in which at least a portion of the therapeutic agent is releasable from the polymeric material upon heating.
61. The medical device of Claim 31 that further comprises an effective amount of at least one magnetic resonance enhancing agent.
62. A method of treatment comprising introducing a medical device into a body cavity of a mammal in an amount that is effective to at least partially occlude the body cavity, wherein the medical device comprises a polymeric material, and wherein the polymeric material comprises a biocompatible inherently radiopaque side chain crystallizable polymer.
63. The method of Claim 62 in which the body cavity is selected from the group consisting of a tube, a tubule, a duct, a channel, a foramen, a vessel, a void, and a canal.
64. The method of Claim 62 in which the polymeric material has a melting point in the range of about 30°C to about 80°C.
65. The method of Claim 64 in which introducing the medical device into the body cavity comprises heating the polymeric material to a temperature that is higher than the melting point.
66. The method of Claim 65 in which introducing the medical device into the body cavity comprises cooling the polymeric material to a temperature that is lower than the melting point.
67. The method of Claim 66 in which the body cavity is a blood vessel.
68. The method of Claim 67 in which the blood vessel is a varicose vein.
69. The method of Claim 67 in which introducing the medical device into the blood vessel comprises flowing the polymeric material through a catheter, a syringe, a nozzle or combination thereof.
70. A method for making an inherently radiopaque side chain crystallizable polymer, comprising copolymerizing a first monomer and a second monomer, the first monomer comprising a heavy atom and the second monomer comprising a crystallizable group.
71. The method of Claim 70 in which the heavy atom is selected from the group consisting of bromine and iodine.
72. The method of Claim 70 in which the crystallizable group comprises from about 6 to about 30 carbon atoms.
73. A method for making an inherently radiopaque side chain crystallizable polymer, comprising reacting a side chain crystallizable polymer with a heavy metal reagent under conditions selected to attach a plurality of heavy atoms to the side chain crystallizable polymer.
74. The method of Claim 73 in which the heavy metal reagent comprises bromine.
75. The method of Claim 73 in which the heavy metal reagent comprises iodine.
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Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6623521B2 (en) 1998-02-17 2003-09-23 Md3, Inc. Expandable stent with sliding and locking radial elements
US20070142901A1 (en) * 1998-02-17 2007-06-21 Steinke Thomas A Expandable stent with sliding and locking radial elements
US7700819B2 (en) 2001-02-16 2010-04-20 Kci Licensing, Inc. Biocompatible wound dressing
US7763769B2 (en) * 2001-02-16 2010-07-27 Kci Licensing, Inc. Biocompatible wound dressing
AU2003270070A1 (en) * 2002-09-04 2004-03-29 Reva Medical, Inc. A slide and lock stent and method of manufacture from a single piece shape
WO2005030268A1 (en) 2003-09-25 2005-04-07 Rutgers, The State University Inherently radiopaque polymeric products for embolotherapy
US8703113B2 (en) 2004-07-08 2014-04-22 Reva Medical Inc. Side-chain crystallizable polymers for medical applications
AU2005269868B2 (en) 2004-07-08 2008-10-23 Reva Medical, Inc. Side-chain crystallizable polymers for medical applications
US8702716B1 (en) 2009-09-21 2014-04-22 Reva Medical Inc. Devices, compositions and methods for bone and tissue augmentation
US7763065B2 (en) 2004-07-21 2010-07-27 Reva Medical, Inc. Balloon expandable crush-recoverable stent device
US20060034769A1 (en) * 2004-08-13 2006-02-16 Rutgers, The State University Radiopaque polymeric stents
RU2396289C2 (en) 2004-08-13 2010-08-10 Рева Медикал, Инк. Multi-purpose bioresorbable, inherently radio-opaque polymers
US8292944B2 (en) 2004-12-17 2012-10-23 Reva Medical, Inc. Slide-and-lock stent
US7914574B2 (en) * 2005-08-02 2011-03-29 Reva Medical, Inc. Axially nested slide and lock expandable device
US9149378B2 (en) 2005-08-02 2015-10-06 Reva Medical, Inc. Axially nested slide and lock expandable device
US8235939B2 (en) * 2006-02-06 2012-08-07 Kci Licensing, Inc. System and method for purging a reduced pressure apparatus during the administration of reduced pressure treatment
US8267918B2 (en) * 2006-03-14 2012-09-18 Kci Licensing, Inc. System and method for percutaneously administering reduced pressure treatment using a flowable manifold
US9456860B2 (en) * 2006-03-14 2016-10-04 Kci Licensing, Inc. Bioresorbable foaming tissue dressing
CN101415449A (en) * 2006-04-06 2009-04-22 雷瓦医药公司 Embolism prosthesis for treating vas aneurysm
US8507639B2 (en) * 2006-09-11 2013-08-13 Boston Scientific Scimed, Inc. Radiopaque amide polymers and medical devices formed thereof
JP5165686B2 (en) 2006-10-17 2013-03-21 ラトガース,ザ ステート ユニバーシティ N-substituted monomers and polymers
US7704275B2 (en) 2007-01-26 2010-04-27 Reva Medical, Inc. Circumferentially nested expandable device
EP1992371A1 (en) * 2007-05-15 2008-11-19 Occlutech GmbH Bio reabsorbable polymer materials opaque to X-rays and occlusion instruments made thereof
JP5216098B2 (en) 2007-11-30 2013-06-19 レヴァ メディカル、 インコーポレイテッド Axial and radially nested expandable device
EP2331014B1 (en) 2008-10-10 2017-08-09 Reva Medical, Inc. Expandable slide and lock stent
CA2737763C (en) 2008-10-11 2019-04-09 Rutgers, The State University Of New Jersey Phase-separated biocompatible polymer compositions for medical uses
US20100137908A1 (en) * 2008-12-01 2010-06-03 Zimmer Spine, Inc. Dynamic Stabilization System Components Including Readily Visualized Polymeric Compositions
RU2011127674A (en) * 2008-12-31 2013-02-10 КейСиАй ЛАЙСЕНЗИНГ, ИНК. HIGHWAYS, SYSTEMS AND METHODS FOR APPLYING THE REDUCED PRESSURE TO THE SUBSTANCE OF THE SUBCUTANEOUS TISSUE
EP2459638B1 (en) 2009-07-31 2017-09-27 Rutgers, The State University of New Jersey Monomers and phase-separated biocompatible polymer compositions prepared therefrom for medical uses
EP2486081B1 (en) 2009-10-11 2018-12-05 Rutgers, The State University of New Jersey Biocompatible polymers for medial devices
US20110086001A1 (en) * 2009-10-11 2011-04-14 Rutgers University Compliant biocompatible polymer compositions for medical uses
WO2011127452A1 (en) 2010-04-10 2011-10-13 Reva Medical, Inc Expandable slide and lock stent
WO2012019145A1 (en) 2010-08-06 2012-02-09 Endoshape, Inc. Radiopaque shape memory polymers for medical devices
JP2012180497A (en) * 2011-02-08 2012-09-20 Kaneka Corp Highly thermoconductive thermoplastic resin composition
US11472918B2 (en) 2012-02-03 2022-10-18 Rutgers, The State University Of New Jersey Polymeric biomaterials derived from phenolic monomers and their medical uses
JP6182159B2 (en) 2012-02-03 2017-08-16 ラトガース,ザ ステート ユニバーシティ オブ ニュー ジャージー Polymeric biomaterials derived from phenolic monomers and their medical applications
WO2014124225A1 (en) 2013-02-08 2014-08-14 Endoshape, Inc. Radiopaque polymers for medical devices
US9408732B2 (en) 2013-03-14 2016-08-09 Reva Medical, Inc. Reduced-profile slide and lock stent
JP6543831B2 (en) 2013-03-15 2019-07-17 エンドゥーシェイプ インコーポレイテッド Polymer composition having enhanced radiopacity
WO2015021254A1 (en) 2013-08-07 2015-02-12 Rutgers, The State Universtity Of New Jersey Polymeric biomaterials derived from monomers comprising hydroxyacids and phenol compounds and their medical uses
CN106103613B (en) * 2014-03-10 2019-07-09 3M创新有限公司 Conformal coating composition
AU2015370426B2 (en) * 2014-12-23 2019-09-12 Rutgers, The State University Of New Jersey Biocompatible iodinated diphenol monomers and polymers
US10774030B2 (en) 2014-12-23 2020-09-15 Rutgers, The State University Of New Jersey Polymeric biomaterials derived from phenolic monomers and their medical uses
WO2018102714A1 (en) 2016-12-02 2018-06-07 Endoshape, Inc. Radiopaque polymers with enhanced radiopacity
US11223722B1 (en) * 2020-12-23 2022-01-11 AcqueonTechnologies Inc. System and method for unified autodial campaign management

Family Cites Families (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE348111B (en) 1967-11-16 1972-08-28 Pharmacia Ab
US4638045A (en) 1985-02-19 1987-01-20 Massachusetts Institute Of Technology Non-peptide polyamino acid bioerodible polymers
US4863735A (en) 1985-02-19 1989-09-05 Massachusetts Institute Of Technology Biodegradable polymeric drug delivery system with adjuvant activity
JPS6234101A (en) 1985-08-08 1987-02-14 Toray Ind Inc Plastic lens having high refractive index
EP0266775A3 (en) 1986-11-07 1989-11-08 Showa Denko Kabushiki Kaisha Laminates
US4980449A (en) * 1988-07-14 1990-12-25 Rutgers, The State University Polyiminocarbonate synthesis
US5587507A (en) * 1995-03-31 1996-12-24 Rutgers, The State University Synthesis of tyrosine derived diphenol monomers
US5198507A (en) 1990-06-12 1993-03-30 Rutgers, The State University Of New Jersey Synthesis of amino acid-derived bioerodible polymers
US5163952A (en) 1990-09-14 1992-11-17 Michael Froix Expandable polymeric stent with memory and delivery apparatus and method
US5613952A (en) * 1991-12-23 1997-03-25 Syringe Develpoment Partners Safety syringe
US5469867A (en) 1992-09-02 1995-11-28 Landec Corporation Cast-in place thermoplastic channel occluder
US5466439A (en) 1992-11-12 1995-11-14 Magnetic Research, Inc. Polymeric contrast enhancing agents for magnetic resonance images
JPH0727766A (en) 1993-06-24 1995-01-31 Eiken Chem Co Ltd Reagent-bonded polymer and its preparation
US5443477A (en) 1994-02-10 1995-08-22 Stentco, Inc. Apparatus and method for deployment of radially expandable stents by a mechanical linkage
JP3472340B2 (en) * 1994-05-09 2003-12-02 鐘淵化学工業株式会社 Curable composition
US6831116B2 (en) 1995-03-07 2004-12-14 Landec Corporation Polymeric modifying agents
US5674242A (en) 1995-06-06 1997-10-07 Quanam Medical Corporation Endoprosthetic device with therapeutic compound
US6319492B1 (en) 1996-11-27 2001-11-20 Rutgers, The State University Copolymers of tyrosine-based polyarylates and poly(alkylene oxides)
JP4410857B2 (en) * 1997-02-18 2010-02-03 ラットガーズ ザ ステイト ユニヴァーシティ Monomers derived from hydroxy acids and polymers prepared therefrom
JPH10259298A (en) 1997-03-21 1998-09-29 Mitsubishi Eng Plast Kk Polycarbonate resin composition
US5912225A (en) * 1997-04-14 1999-06-15 Johns Hopkins Univ. School Of Medicine Biodegradable poly (phosphoester-co-desaminotyrosyl L-tyrosine ester) compounds, compositions, articles and methods for making and using the same
DE69842217D1 (en) * 1997-11-07 2011-05-19 State University Radiopaque polymeric biomaterials
EP0930343A3 (en) 1998-01-16 2000-05-31 Landec Corporation Low profile additives for crosslink resins
US6492462B2 (en) 1998-01-16 2002-12-10 Landec Corporation Side chain crystalline polymer as rheology modifier for crosslinked polymer
US6623521B2 (en) 1998-02-17 2003-09-23 Md3, Inc. Expandable stent with sliding and locking radial elements
DK1062278T3 (en) 1998-02-23 2006-09-25 Mnemoscience Gmbh Polymers with shape memory
US6015424A (en) 1998-04-28 2000-01-18 Microvention, Inc. Apparatus and method for vascular embolization
US6273909B1 (en) 1998-10-05 2001-08-14 Teramed Inc. Endovascular graft system
US6200338B1 (en) 1998-12-31 2001-03-13 Ethicon, Inc. Enhanced radiopacity of peripheral and central catheter tubing
US6599448B1 (en) 2000-05-10 2003-07-29 Hydromer, Inc. Radio-opaque polymeric compositions
US6550480B2 (en) 2001-01-31 2003-04-22 Numed/Tech Llc Lumen occluders made from thermodynamic materials
US6976106B2 (en) * 2002-11-01 2005-12-13 Sonics, Inc. Method and apparatus for speculative response arbitration to improve system latency
US7455687B2 (en) 2002-12-30 2008-11-25 Advanced Cardiovascular Systems, Inc. Polymer link hybrid stent
US6932930B2 (en) 2003-03-10 2005-08-23 Synecor, Llc Intraluminal prostheses having polymeric material with selectively modified crystallinity and methods of making same
CA2527976C (en) 2003-06-13 2011-11-22 Mnemoscience Gmbh Stents
WO2005030268A1 (en) 2003-09-25 2005-04-07 Rutgers, The State University Inherently radiopaque polymeric products for embolotherapy
AU2005269868B2 (en) * 2004-07-08 2008-10-23 Reva Medical, Inc. Side-chain crystallizable polymers for medical applications
RU2396289C2 (en) * 2004-08-13 2010-08-10 Рева Медикал, Инк. Multi-purpose bioresorbable, inherently radio-opaque polymers

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