WO1998022517A1 - Anion exchange materials and processes - Google Patents

Anion exchange materials and processes Download PDF

Info

Publication number
WO1998022517A1
WO1998022517A1 PCT/GB1997/003192 GB9703192W WO9822517A1 WO 1998022517 A1 WO1998022517 A1 WO 1998022517A1 GB 9703192 W GB9703192 W GB 9703192W WO 9822517 A1 WO9822517 A1 WO 9822517A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkylene
groups
cationic
alkyl
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.)
Ceased
Application number
PCT/GB1997/003192
Other languages
English (en)
French (fr)
Inventor
Joachim Storch
Robert Neil Hanley
Richard Neil Templar Freeman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Abbott Vascular Devices Ltd
Original Assignee
Biocompatibles Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Biocompatibles Ltd filed Critical Biocompatibles Ltd
Priority to JP52336498A priority Critical patent/JP4051414B2/ja
Priority to DE69711913T priority patent/DE69711913T2/de
Priority to EP97913311A priority patent/EP0939779B1/en
Priority to AT97913311T priority patent/ATE215971T1/de
Priority to US09/308,496 priority patent/US6432314B1/en
Priority to AU50611/98A priority patent/AU5061198A/en
Publication of WO1998022517A1 publication Critical patent/WO1998022517A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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

Definitions

  • X is a group of formula
  • B is a bond or a straight or branched alkylene, alkylene-oxa-alkylene or alkylene-oligooxa- alkylene group, any of which optionally include one or more fluorine substituents;
  • X is an organic group having a zwitterionic moiety preferably as described above;
  • R is hydrogen or a C ⁇ C,, alkyl group;
  • A is -0- or -NR 1 - where R 1 is hydrogen or a C ⁇ C, alkyl group or R 1 is -B-X, B , B 2 Q 2 or BQ 3 where B, B 1 , B 2 , B J , Q 1 , Q 2 and Q 3 and X are as defined above in the respective formulae I, II, III and IV and K is a group - (CH 2 ) p 0C(0) -, -(CH 2 ) P C(0) 0-, -(CH 2 ) p 0C(0)0-, -(CH 2 ) p NR 2 -, -(CH 2 ) p NR 2 C (O) -, -(CH 2 ) p C(0)NR 2 -, -(CH 2 ) p NR 2 C(0)0-, - (CH 2 ) p 0C (O) NR 2 -, -(CH 2 )
  • Copolymerisable nonionic monomers may be used such as C 1-24 alkyl (meth) aerylates, -(meth) acrylamides, and hydroxy C ⁇ _ 24 alkyl (meth) acrylates and (meth) acrylamides.
  • Arterial filters were filled with 100 ml of a heparin solution in PBS (50 U/ml) and inlet/outlet sides were closed. The filter was rotated for 30 min, ensuring that all parts of the device were in contact with the heparin loading solution. The filter was then drained and filled/drained 3 times with PBS and then filled/drained 3 times with deionized water. The filter was dried by a stream of air and stored at room temperature.
  • Zwitterionic monomer 34.10g, 0.116 mole
  • cationic monomer 6.3g, 0.030 mole
  • Dodecyl methacrylate (60.0lg, 0.236 mole), hydroxypropyl methacrylate monomer (14.51g, 0.101 mole), trimethyoxysilyl monomer (5.00g, 0.020 mole) and AIBN initiator (0.2409g, 0.2%) were weighed in air.
  • Dodecyl methacrylate was pre-columned through activated basic alumina (Brockmann 1 ca.150 mesh, 50g) before use. Dry nitrogen gas was bubbled through for 20 minutes to degas the reaction mixture at room temperature before immersing the reaction vessel in an oil bath heated to 67°C. The vessel was heated for 15 minutes prior to AIBN initiator (0.14g, l.lwt%) being rinsed into the reaction mixture with 2ml solvent mixture. The reaction was magnetically stirred and maintained under a positive pressure nitrogen blanket sufficient to bubble through a mineral oil bubbler. The reaction time was 39.5 hours.
  • the heparin activity on the DurafloII sample was 240 mU/cm 2 and 33.5 mU/cm 2 on the Medtronic M40.
  • the Carmeda BioActive Surface heparin appeared to be more stable with BSA, but the initial heparin activity was the lowest of all filters tested. Previous results have shown that another 20 micron Medtronic filter with Carmeda bonded heparin had only 2,3 mU/cm 2 .

Landscapes

  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Materials For Medical Uses (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • External Artificial Organs (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
PCT/GB1997/003192 1996-11-20 1997-11-20 Anion exchange materials and processes Ceased WO1998022517A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP52336498A JP4051414B2 (ja) 1996-11-20 1997-11-20 陰イオン交換材料およびその方法
DE69711913T DE69711913T2 (de) 1996-11-20 1997-11-20 Anionenaustauschmaterialien und verfahren
EP97913311A EP0939779B1 (en) 1996-11-20 1997-11-20 Anion exchange materials and processes
AT97913311T ATE215971T1 (de) 1996-11-20 1997-11-20 Anionenaustauschmaterialien und verfahren
US09/308,496 US6432314B1 (en) 1996-11-20 1997-11-20 Anion exchange materials and processes
AU50611/98A AU5061198A (en) 1996-11-20 1997-11-20 Anion exchange materials and processes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9624130.2A GB9624130D0 (en) 1996-11-20 1996-11-20 Biocompatible compositions
GB9624130.2 1996-11-20

Publications (1)

Publication Number Publication Date
WO1998022517A1 true WO1998022517A1 (en) 1998-05-28

Family

ID=10803229

Family Applications (3)

Application Number Title Priority Date Filing Date
PCT/GB1997/003192 Ceased WO1998022517A1 (en) 1996-11-20 1997-11-20 Anion exchange materials and processes
PCT/GB1997/003191 Ceased WO1998022162A1 (en) 1996-11-20 1997-11-20 Biocompatible compositions
PCT/GB1997/003189 Ceased WO1998022516A1 (en) 1996-11-20 1997-11-20 Biocompatible compositions

Family Applications After (2)

Application Number Title Priority Date Filing Date
PCT/GB1997/003191 Ceased WO1998022162A1 (en) 1996-11-20 1997-11-20 Biocompatible compositions
PCT/GB1997/003189 Ceased WO1998022516A1 (en) 1996-11-20 1997-11-20 Biocompatible compositions

Country Status (11)

Country Link
US (2) US6251964B1 (cg-RX-API-DMAC7.html)
EP (2) EP0939779B1 (cg-RX-API-DMAC7.html)
JP (2) JP4051414B2 (cg-RX-API-DMAC7.html)
AT (2) ATE215971T1 (cg-RX-API-DMAC7.html)
AU (3) AU728887B2 (cg-RX-API-DMAC7.html)
CA (1) CA2271132C (cg-RX-API-DMAC7.html)
DE (2) DE69701319T2 (cg-RX-API-DMAC7.html)
ES (1) ES2143301T3 (cg-RX-API-DMAC7.html)
GB (1) GB9624130D0 (cg-RX-API-DMAC7.html)
WO (3) WO1998022517A1 (cg-RX-API-DMAC7.html)
ZA (3) ZA9710467B (cg-RX-API-DMAC7.html)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003074090A2 (en) 2002-03-07 2003-09-12 Biocompatibles Uk Limited Compositions of polymers
US6746686B2 (en) 2000-01-24 2004-06-08 Biocompatibles Uk Limited Coated implants
US8465758B2 (en) 2001-01-11 2013-06-18 Abbott Laboratories Drug delivery from stents
US8846839B2 (en) 2006-11-21 2014-09-30 Abbott Laboratories Copolymers having zwitterionic moieties and dihdroxyphenyl moieties and medical devices coated with the copolymers
US9180225B2 (en) 2007-05-14 2015-11-10 Abbott Laboratories Implantable medical devices with a topcoat layer of phosphoryl choline acrylate polymer for reduced thrombosis, and improved mechanical properties

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US6743878B2 (en) * 1991-07-05 2004-06-01 Biocompatibles Uk Limited Polymeric surface coatings
GB9522332D0 (en) 1995-11-01 1996-01-03 Biocompatibles Ltd Braided stent
US6258371B1 (en) * 1998-04-03 2001-07-10 Medtronic Inc Method for making biocompatible medical article
ATE406922T1 (de) 1998-07-07 2008-09-15 Nof Corp Zusammensetzung zur wundheilung, wundverband und verfahren zur behandlung vonwunden
ATE260306T1 (de) * 1998-12-11 2004-03-15 Biocompatibles Uk Ltd Vernetzte polymere und refraktionsvorrichtung aus diesen geformt
EP1180013B1 (en) 1999-05-27 2006-03-08 Biocompatibles UK Limited Local drug delivery
AU4941100A (en) 1999-05-27 2001-02-19 Biocompatibles Limited Polymer solutions
EP1325046B1 (en) 2000-10-06 2007-06-27 Biocompatibles UK Limited Zwitterionic polymers
DE60215635T2 (de) * 2001-04-26 2009-07-09 Nof Corp. Inhibitoren zur Inhibierung unspezifischer Hybridisierung, klinische Diagnosereagenzien und ein Verfahren zur klinischen Analyse
US6844028B2 (en) * 2001-06-26 2005-01-18 Accelr8 Technology Corporation Functional surface coating
WO2005027991A1 (en) * 2003-09-19 2005-03-31 Cambridge University Technical Services Ltd Orthopaedic devices
US20050208093A1 (en) * 2004-03-22 2005-09-22 Thierry Glauser Phosphoryl choline coating compositions
JP2006238914A (ja) * 2005-02-28 2006-09-14 Hoya Corp 眼内レンズおよびその製造方法
JP5179487B2 (ja) * 2006-07-14 2013-04-10 バイオコンパティブルズ ユーケー リミテッド ポリマー
JP5019524B2 (ja) * 2007-06-01 2012-09-05 国立大学法人 東京大学 新規ポリ（メタ）アクリレート共重合体ならびに小胞体及びゴルジ体への送達方法
CA2745204C (en) * 2008-12-05 2017-01-03 Semprus Biosciences Corp. Layered non-fouling, antimicrobial, antithrombogenic coatings
CA2799786A1 (en) 2010-06-09 2011-12-15 Semprus Biosciences Corp. Non-fouling, anti-microbial, anti-thrombogenic graft compositions
SG186180A1 (en) 2010-06-09 2013-01-30 Semprus Biosciences Corp Non-fouling, anti-microbial, anti-thrombogenic graft-from compositions
US8519189B2 (en) 2011-06-01 2013-08-27 University Of British Columbia Polymers for reversing heparin-based anticoagulation
WO2013090813A1 (en) 2011-12-14 2013-06-20 Semprus Biosciences Corp. Redox processes for contact lens modification
US9000063B2 (en) 2011-12-14 2015-04-07 Semprus Biosciences Corporation Multistep UV process to create surface modified contact lenses
CA2858730C (en) 2011-12-14 2017-07-18 Semprus Biosciences Corp. Surface modified contact lenses
WO2013090790A1 (en) 2011-12-14 2013-06-20 Semprus Biosciences Corp. Silicone hydrogel contact lens modified using lanthanide or transition metal oxidants
US9006359B2 (en) 2011-12-14 2015-04-14 Semprus Biosciences Corporation Imbibing process for contact lens surface modification
CN103193927B (zh) * 2013-04-27 2016-01-20 南京构友生物材料有限公司 可键合的血液友好聚合物及其制法与用途
WO2014192731A1 (ja) * 2013-05-27 2014-12-04 Jsr株式会社 無機材料で構成される表面用の表面処理剤、表面が改質された器具および装置、該器具および装置の製造方法
US10384167B2 (en) 2013-11-21 2019-08-20 Oasys Water LLC Systems and methods for improving performance of osmotically driven membrane systems
CN106794290B (zh) 2014-10-02 2020-11-06 旭化成医疗株式会社 源自生物体的液体处理过滤器及过滤器装置
KR20180076552A (ko) * 2016-12-28 2018-07-06 주식회사 엘지화학 친수성 코팅 조성물
SG11202112411SA (en) * 2019-05-10 2021-12-30 Tufts College Zwitterionic charged copolymer membranes
CA3219033A1 (en) 2021-05-27 2022-12-01 Metro International Biotech, Llc Crystalline solids of nicotinic acid mononucleotide and esters thereof and methods of making and use
CN113476661B (zh) * 2021-07-05 2022-08-05 中国医学科学院生物医学工程研究所 一种三层结构复合型自愈合人造血管及其制备方法

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6746686B2 (en) 2000-01-24 2004-06-08 Biocompatibles Uk Limited Coated implants
US8465758B2 (en) 2001-01-11 2013-06-18 Abbott Laboratories Drug delivery from stents
WO2003074090A2 (en) 2002-03-07 2003-09-12 Biocompatibles Uk Limited Compositions of polymers
US8182802B2 (en) 2002-03-07 2012-05-22 Biocompatibles Uk Limited Composition of polymers
US8846839B2 (en) 2006-11-21 2014-09-30 Abbott Laboratories Copolymers having zwitterionic moieties and dihdroxyphenyl moieties and medical devices coated with the copolymers
US9180225B2 (en) 2007-05-14 2015-11-10 Abbott Laboratories Implantable medical devices with a topcoat layer of phosphoryl choline acrylate polymer for reduced thrombosis, and improved mechanical properties

Also Published As

Publication number Publication date
DE69701319T2 (de) 2000-07-13
JP4051414B2 (ja) 2008-02-27
ATE189899T1 (de) 2000-03-15
WO1998022162A1 (en) 1998-05-28
WO1998022516A1 (en) 1998-05-28
US6251964B1 (en) 2001-06-26
ATE215971T1 (de) 2002-04-15
ZA9710467B (en) 1998-11-20
EP0939779A1 (en) 1999-09-08
EP0866815A2 (en) 1998-09-30
AU5060898A (en) 1998-06-10
JP2001506915A (ja) 2001-05-29
EP0866815B1 (en) 2000-02-23
DE69701319D1 (de) 2000-03-30
ZA9710468B (en) 1998-11-20
US6432314B1 (en) 2002-08-13
AU728887B2 (en) 2001-01-18
JP4295359B2 (ja) 2009-07-15
CA2271132C (en) 2007-04-17
ES2143301T3 (es) 2000-05-01
EP0866815A3 (en) 1998-10-21
EP0939779B1 (en) 2002-04-10
GB9624130D0 (en) 1997-01-08
JP2001504877A (ja) 2001-04-10
ZA9710466B (en) 1998-11-20
CA2271132A1 (en) 1998-05-28
DE69711913D1 (de) 2002-05-16
DE69711913T2 (de) 2002-10-10
AU5061198A (en) 1998-06-10
AU5061098A (en) 1998-06-10

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