AU734370B2 - Methods for actively binding heparin to biological and non- biological bioprosthetic material - Google Patents
Methods for actively binding heparin to biological and non- biological bioprosthetic material Download PDFInfo
- Publication number
- AU734370B2 AU734370B2 AU64523/98A AU6452398A AU734370B2 AU 734370 B2 AU734370 B2 AU 734370B2 AU 64523/98 A AU64523/98 A AU 64523/98A AU 6452398 A AU6452398 A AU 6452398A AU 734370 B2 AU734370 B2 AU 734370B2
- Authority
- AU
- Australia
- Prior art keywords
- biological material
- solution
- polyamine
- contacting
- carboxyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 105
- 229920000669 heparin Polymers 0.000 title claims description 66
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 title claims description 65
- 229960002897 heparin Drugs 0.000 title claims description 65
- 239000000463 material Substances 0.000 title claims description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 118
- 210000001519 tissue Anatomy 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 63
- 239000012620 biological material Substances 0.000 claims description 62
- 229920000768 polyamine Polymers 0.000 claims description 60
- 210000002808 connective tissue Anatomy 0.000 claims description 55
- 239000000243 solution Substances 0.000 claims description 54
- 102000004169 proteins and genes Human genes 0.000 claims description 50
- 108090000623 proteins and genes Proteins 0.000 claims description 50
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 43
- 239000004472 Lysine Substances 0.000 claims description 43
- 125000003277 amino group Chemical group 0.000 claims description 37
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 21
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 16
- 230000003213 activating effect Effects 0.000 claims description 15
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- 239000003431 cross linking reagent Substances 0.000 claims description 11
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 10
- 230000009467 reduction Effects 0.000 claims description 10
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- 238000004659 sterilization and disinfection Methods 0.000 claims description 6
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 4
- 102000015636 Oligopeptides Human genes 0.000 claims description 4
- 108010038807 Oligopeptides Proteins 0.000 claims description 4
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 4
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 4
- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- TXOUDPQJASQYBZ-UHFFFAOYSA-N n,n'-dihexylmethanediimine Chemical compound CCCCCCN=C=NCCCCCC TXOUDPQJASQYBZ-UHFFFAOYSA-N 0.000 claims description 4
- 229960003104 ornithine Drugs 0.000 claims description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
- VJINKBZUJYGZGP-UHFFFAOYSA-N 3-(1-aminopropylideneamino)propyl-trimethylazanium Chemical compound CCC(N)=NCCC[N+](C)(C)C VJINKBZUJYGZGP-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 claims 3
- YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 claims 3
- 125000005442 diisocyanate group Chemical group 0.000 claims 3
- YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 claims 3
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 claims 3
- 230000002045 lasting effect Effects 0.000 claims 2
- 102000008186 Collagen Human genes 0.000 description 36
- 108010035532 Collagen Proteins 0.000 description 36
- 229920001436 collagen Polymers 0.000 description 35
- 102000016942 Elastin Human genes 0.000 description 19
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- 230000002308 calcification Effects 0.000 description 17
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- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- KATAXDCYPGGJNJ-UHFFFAOYSA-N 1,3-bis(oxiran-2-ylmethoxy)propan-2-ol Chemical compound C1OC1COCC(O)COCC1CO1 KATAXDCYPGGJNJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 210000004379 membrane Anatomy 0.000 description 3
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- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- 229920002085 Dialdehyde starch Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- 206010021542 Implant site reaction Diseases 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 230000002429 anti-coagulating effect Effects 0.000 description 2
- 230000002965 anti-thrombogenic effect Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000012304 carboxyl activating agent Substances 0.000 description 2
- 238000010382 chemical cross-linking Methods 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
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- 230000000116 mitigating effect Effects 0.000 description 2
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- 239000008363 phosphate buffer Substances 0.000 description 2
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- BQSMUQUKNCGJCT-SLPGGIOYSA-N 2-N,6-O-disulfo-D-glucosamine Chemical compound OS(=O)(=O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](NS(O)(=O)=O)C=O BQSMUQUKNCGJCT-SLPGGIOYSA-N 0.000 description 1
- 244000186140 Asperula odorata Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000035448 Device deposit issue Diseases 0.000 description 1
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000008526 Galium odoratum Nutrition 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 208000037147 Hypercalcaemia Diseases 0.000 description 1
- OXFPUTVGMDTUNO-SKNVOMKLSA-N L-iduronic acid 2-sulfate Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](C(O)=O)OS(O)(=O)=O OXFPUTVGMDTUNO-SKNVOMKLSA-N 0.000 description 1
- 108010013563 Lipoprotein Lipase Proteins 0.000 description 1
- 102100022119 Lipoprotein lipase Human genes 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 108010007568 Protamines Proteins 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 206010060872 Transplant failure Diseases 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 210000003484 anatomy Anatomy 0.000 description 1
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- 239000004019 antithrombin Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
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- 230000033558 biomineral tissue development Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
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- VEVRNHHLCPGNDU-MUGJNUQGSA-O desmosine Chemical compound OC(=O)[C@@H](N)CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C(O)=O)C(CC[C@H](N)C(O)=O)=C1 VEVRNHHLCPGNDU-MUGJNUQGSA-O 0.000 description 1
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- 229920000295 expanded polytetrafluoroethylene Polymers 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 230000000148 hypercalcaemia Effects 0.000 description 1
- 208000030915 hypercalcemia disease Diseases 0.000 description 1
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- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/0005—Use of materials characterised by their function or physical properties
- A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
- A61L33/0029—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate using an intermediate layer of polymer
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/0005—Use of materials characterised by their function or physical properties
- A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Materials For Medical Uses (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/843,504 US5891196A (en) | 1997-04-16 | 1997-04-16 | Method for actively binding heparin to crosslinked biological tissues |
| US08/843504 | 1997-04-16 | ||
| PCT/US1998/004508 WO1998046288A1 (en) | 1997-04-16 | 1998-03-06 | Methods for actively binding heparin to cross-linked biological tissues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6452398A AU6452398A (en) | 1998-11-11 |
| AU734370B2 true AU734370B2 (en) | 2001-06-14 |
Family
ID=25290197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU64523/98A Expired AU734370B2 (en) | 1997-04-16 | 1998-03-06 | Methods for actively binding heparin to biological and non- biological bioprosthetic material |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5891196A (enExample) |
| EP (1) | EP0975378A1 (enExample) |
| JP (1) | JP2001520539A (enExample) |
| AU (1) | AU734370B2 (enExample) |
| CA (1) | CA2286900C (enExample) |
| WO (1) | WO1998046288A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996004028A1 (en) * | 1994-07-29 | 1996-02-15 | Baxter International Inc. | Methods for treating implantable biological tissues to mitigate the calcification thereof and bioprosthetic articles treated by such methods |
| US6562781B1 (en) | 1995-11-30 | 2003-05-13 | Hamilton Civic Hospitals Research Development Inc. | Glycosaminoglycan-antithrombin III/heparin cofactor II conjugates |
| US7045585B2 (en) * | 1995-11-30 | 2006-05-16 | Hamilton Civic Hospital Research Development Inc. | Methods of coating a device using anti-thrombin heparin |
| US6491965B1 (en) * | 1995-11-30 | 2002-12-10 | Hamilton Civic Hospitals Research Development, Inc. | Medical device comprising glycosaminoglycan-antithrombin III/heparin cofactor II conjugates |
| US6206917B1 (en) * | 1997-05-02 | 2001-03-27 | St. Jude Medical, Inc. | Differential treatment of prosthetic devices |
| US6214054B1 (en) * | 1998-09-21 | 2001-04-10 | Edwards Lifesciences Corporation | Method for fixation of biological tissues having mitigated propensity for post-implantation calcification and thrombosis and bioprosthetic devices prepared thereby |
| EP1117446B1 (en) | 1998-09-30 | 2004-11-24 | Medtronic, Inc. | Process for reducing mineralization of tissue used in transplantation |
| WO2000064371A1 (en) * | 1999-04-27 | 2000-11-02 | The Children's Hospital Of Philadelphia | Stabilization of implantable bioprosthetic devices |
| US7604663B1 (en) | 1999-12-30 | 2009-10-20 | St. Jude Medical, Inc. | Medical devices with polymer/inorganic substrate composites |
| US6471723B1 (en) | 2000-01-10 | 2002-10-29 | St. Jude Medical, Inc. | Biocompatible prosthetic tissue |
| FR2804328B1 (fr) | 2000-01-27 | 2002-03-15 | Hospal Ind | Membrane semi-permeable non thrombogene et procede de fabrication |
| US6391538B1 (en) * | 2000-02-09 | 2002-05-21 | The Children's Hospital Of Philadelphia | Stabilization of implantable bioprosthetic tissue |
| DE10060660A1 (de) | 2000-12-06 | 2002-06-20 | Frey Rainer | Verfahren zur Konservierung von biologischen Prothesen, konservierte biologische Prothese und Konservierungslösung |
| US20020177223A1 (en) * | 2001-03-12 | 2002-11-28 | Ogle Mathew F. | Methods and compositions for crosslinking tissue |
| US7078163B2 (en) * | 2001-03-30 | 2006-07-18 | Medtronic, Inc. | Process for reducing mineralization of tissue used in transplantation |
| US20030077310A1 (en) * | 2001-10-22 | 2003-04-24 | Chandrashekhar Pathak | Stent coatings containing HMG-CoA reductase inhibitors |
| US7955788B2 (en) * | 2003-10-30 | 2011-06-07 | Medtronic, Inc. | Bioprosthetic tissue preparation with synthetic hydrogels |
| US20050266390A1 (en) * | 2004-06-01 | 2005-12-01 | Yuichiro Ueda | Processes for removing cells and cell debris from tissue and tissue constructs used in transplantation and tissue reconstruction |
| US7989157B2 (en) * | 2005-01-11 | 2011-08-02 | Medtronic, Inc. | Solution for storing bioprosthetic tissue used in a biological prosthesis |
| CN1903143A (zh) * | 2005-07-29 | 2007-01-31 | 广东冠昊生物科技有限公司 | 生物型人工血管及其制备方法 |
| CN100482178C (zh) * | 2005-08-04 | 2009-04-29 | 广东冠昊生物科技有限公司 | 带生物膜的血管瘤夹 |
| US20070218038A1 (en) * | 2006-03-17 | 2007-09-20 | Pegasus Biologics, Inc. | Stabilized, sterilized collagen scaffolds with active adjuncts attached |
| CN113499478B (zh) * | 2021-07-07 | 2022-07-12 | 成都纽脉生物科技有限公司 | 一种生物组织材料的处理方法 |
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- 1998-03-06 EP EP98910231A patent/EP0975378A1/en not_active Withdrawn
- 1998-03-06 WO PCT/US1998/004508 patent/WO1998046288A1/en not_active Ceased
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- 1998-03-06 JP JP54388698A patent/JP2001520539A/ja active Pending
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| US5134192A (en) * | 1990-02-15 | 1992-07-28 | Cordis Corporation | Process for activating a polymer surface for covalent bonding for subsequent coating with heparin or the like |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6452398A (en) | 1998-11-11 |
| CA2286900A1 (en) | 1998-10-22 |
| WO1998046288A1 (en) | 1998-10-22 |
| CA2286900C (en) | 2008-11-25 |
| US5891196A (en) | 1999-04-06 |
| JP2001520539A (ja) | 2001-10-30 |
| EP0975378A1 (en) | 2000-02-02 |
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