WO1998022517A1 - Anion exchange materials and processes - Google Patents
Anion exchange materials and processes Download PDFInfo
- 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
Links
- 239000000463 material Substances 0.000 title claims abstract description 25
- 238000005349 anion exchange Methods 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 30
- 239000000178 monomer Substances 0.000 claims abstract description 69
- 229920000642 polymer Polymers 0.000 claims abstract description 65
- 125000002091 cationic group Chemical group 0.000 claims abstract description 52
- 239000000758 substrate Substances 0.000 claims abstract description 32
- 238000005342 ion exchange Methods 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- -1 siloxane substituent Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000000129 anionic group Chemical group 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 10
- 239000010452 phosphate Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000962 organic group Chemical group 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229920002683 Glycosaminoglycan Polymers 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000001449 anionic compounds Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229920001897 terpolymer Polymers 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001165 hydrophobic group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 4
- 150000002500 ions Chemical group 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- 229910000831 Steel Inorganic materials 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004254 Ammonium phosphate Substances 0.000 claims 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims 1
- 235000019289 ammonium phosphates Nutrition 0.000 claims 1
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- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical group [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
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- 229920000098 polyolefin Polymers 0.000 claims 1
- 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 abstract description 78
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 19
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 10
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 10
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- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 9
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- 210000004204 blood vessel Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000837 carbohydrate group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UXYBXUYUKHUNOM-UHFFFAOYSA-M ethyl(trimethyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(C)C UXYBXUYUKHUNOM-UHFFFAOYSA-M 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940006607 hirudin Drugs 0.000 description 1
- WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 description 1
- 229940106780 human fibrinogen Drugs 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 102000013415 peroxidase activity proteins Human genes 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000007981 phosphate-citrate buffer Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 238000004375 physisorption Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229940048914 protamine Drugs 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000012492 regenerant Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N sodium azide Substances [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- USFMMZYROHDWPJ-UHFFFAOYSA-N trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical compound CC(=C)C(=O)OCC[N+](C)(C)C USFMMZYROHDWPJ-UHFFFAOYSA-N 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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 .
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/308,496 US6432314B1 (en) | 1996-11-20 | 1997-11-20 | Anion exchange materials and processes |
DE69711913T DE69711913T2 (en) | 1996-11-20 | 1997-11-20 | ANION REPLACEMENT MATERIALS AND METHOD |
EP97913311A EP0939779B1 (en) | 1996-11-20 | 1997-11-20 | Anion exchange materials and processes |
JP52336498A JP4051414B2 (en) | 1996-11-20 | 1997-11-20 | Anion exchange material and method |
AU50611/98A AU5061198A (en) | 1996-11-20 | 1997-11-20 | Anion exchange materials and processes |
AT97913311T ATE215971T1 (en) | 1996-11-20 | 1997-11-20 | ANION EXCHANGE MATERIALS AND METHODS |
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/GB1997/003189 WO1998022516A1 (en) | 1996-11-20 | 1997-11-20 | Biocompatible compositions |
PCT/GB1997/003192 WO1998022517A1 (en) | 1996-11-20 | 1997-11-20 | Anion exchange materials and processes |
PCT/GB1997/003191 WO1998022162A1 (en) | 1996-11-20 | 1997-11-20 | Biocompatible compositions |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1997/003189 WO1998022516A1 (en) | 1996-11-20 | 1997-11-20 | Biocompatible compositions |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1997/003191 WO1998022162A1 (en) | 1996-11-20 | 1997-11-20 | Biocompatible compositions |
Country Status (11)
Country | Link |
---|---|
US (2) | US6251964B1 (en) |
EP (2) | EP0939779B1 (en) |
JP (2) | JP4051414B2 (en) |
AT (2) | ATE189899T1 (en) |
AU (3) | AU728887B2 (en) |
CA (1) | CA2271132C (en) |
DE (2) | DE69701319T2 (en) |
ES (1) | ES2143301T3 (en) |
GB (1) | GB9624130D0 (en) |
WO (3) | WO1998022516A1 (en) |
ZA (3) | ZA9710466B (en) |
Cited By (5)
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 |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO2000001424A1 (en) | 1998-07-07 | 2000-01-13 | Nof Corporation | Wound-covering preparation, wound-covering material, and method of wound healing |
US6767979B1 (en) * | 1998-12-11 | 2004-07-27 | Biocompatibles Uk Limited | Crosslinked polymers and refractive devices formed therefrom |
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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 |
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Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE306597B (en) | 1964-12-17 | 1968-12-02 | Incentive Ab | |
US3861948A (en) * | 1972-05-22 | 1975-01-21 | Kendall & Co | Pressure sensitive adhesive tape |
US3839237A (en) * | 1972-05-31 | 1974-10-01 | Ici Australia Ltd | Ion exchange resins having both acidic and basic ion-exchange sites |
SE456347B (en) | 1982-02-09 | 1988-09-26 | Ird Biomaterial Ab | SURFACE MODIFIED SOLID SUBSTRATE AND PROCEDURES FOR PRODUCING THEREOF |
SE8200751L (en) | 1982-02-09 | 1983-08-10 | Olle Larm | PROCEDURE FOR COVALENT COUPLING FOR MANUFACTURE OF CONJUGATE AND REQUIRED PRODUCTS |
US4517241A (en) * | 1982-12-02 | 1985-05-14 | Alpert Andrew J | Chromatographic support material |
US4704324A (en) * | 1985-04-03 | 1987-11-03 | The Dow Chemical Company | Semi-permeable membranes prepared via reaction of cationic groups with nucleophilic groups |
US4865870A (en) | 1988-07-07 | 1989-09-12 | Becton, Dickinson And Company | Method for rendering a substrate surface antithrombogenic |
JP2890316B2 (en) * | 1989-07-07 | 1999-05-10 | 科学技術振興事業団 | Materials for biocompatible medical devices |
GB9023498D0 (en) | 1990-10-29 | 1990-12-12 | Biocompatibles Ltd | Soft contact lens material |
US5075399A (en) * | 1990-11-15 | 1991-12-24 | Phillips Petroleum Company | Superabsorbent crosslinked ampholytic ion pair copolymers |
DE69230823T2 (en) * | 1991-07-05 | 2000-07-27 | Biocompatibles Ltd | POLYMER SURFACE COATING COMPOSITIONS |
WO1993014127A1 (en) * | 1992-01-21 | 1993-07-22 | University Of Utah | Method and composition for heparin binding using polyaminocations covalently immobilised on polymeric surfaces with polyethylene oxide spacers |
EP0639989B1 (en) | 1992-04-24 | 2001-06-27 | Biocompatibles Limited | Method of reducing microorganism adhesion |
US5342621A (en) * | 1992-09-15 | 1994-08-30 | Advanced Cardiovascular Systems, Inc. | Antithrombogenic surface |
GB9226791D0 (en) * | 1992-12-23 | 1993-02-17 | Biocompatibles Ltd | New materials |
JPH07184989A (en) | 1993-12-28 | 1995-07-25 | Kuraray Co Ltd | High polymer material having compatibility with blood for medical treatment and medical treating material |
JPH07285831A (en) * | 1994-04-18 | 1995-10-31 | Mitsubishi Chem Corp | Hair cosmetic composition |
-
1996
- 1996-11-20 GB GBGB9624130.2A patent/GB9624130D0/en active Pending
-
1997
- 1997-11-20 AU AU50608/98A patent/AU728887B2/en not_active Ceased
- 1997-11-20 DE DE69701319T patent/DE69701319T2/en not_active Expired - Lifetime
- 1997-11-20 WO PCT/GB1997/003189 patent/WO1998022516A1/en active IP Right Grant
- 1997-11-20 EP EP97913311A patent/EP0939779B1/en not_active Expired - Lifetime
- 1997-11-20 AT AT97913308T patent/ATE189899T1/en not_active IP Right Cessation
- 1997-11-20 EP EP97913308A patent/EP0866815B1/en not_active Expired - Lifetime
- 1997-11-20 JP JP52336498A patent/JP4051414B2/en not_active Expired - Fee Related
- 1997-11-20 ZA ZA9710466A patent/ZA9710466B/en unknown
- 1997-11-20 CA CA002271132A patent/CA2271132C/en not_active Expired - Fee Related
- 1997-11-20 ES ES97913308T patent/ES2143301T3/en not_active Expired - Lifetime
- 1997-11-20 US US09/117,729 patent/US6251964B1/en not_active Expired - Lifetime
- 1997-11-20 AT AT97913311T patent/ATE215971T1/en not_active IP Right Cessation
- 1997-11-20 DE DE69711913T patent/DE69711913T2/en not_active Expired - Lifetime
- 1997-11-20 US US09/308,496 patent/US6432314B1/en not_active Expired - Lifetime
- 1997-11-20 AU AU50610/98A patent/AU5061098A/en not_active Abandoned
- 1997-11-20 JP JP52336298A patent/JP4295359B2/en not_active Expired - Lifetime
- 1997-11-20 ZA ZA9710468A patent/ZA9710468B/en unknown
- 1997-11-20 WO PCT/GB1997/003192 patent/WO1998022517A1/en active IP Right Grant
- 1997-11-20 WO PCT/GB1997/003191 patent/WO1998022162A1/en active Application Filing
- 1997-11-20 ZA ZA9710467A patent/ZA9710467B/en unknown
- 1997-11-20 AU AU50611/98A patent/AU5061198A/en not_active Abandoned
Non-Patent Citations (3)
Title |
---|
LOUIS W. YU ET AL.: "zwitterionic stationary phases in HPLC", J. CHROMATOG. SCI, vol. 27, no. 4, 1989, pages 176 - 185, XP000677275 * |
MEI.HUI YANG ET AL.: "multifunctional ion-exchange stationary phases for high-performance liquid chromatography", J. CHROMATOGR., A, vol. 722(1+2), 1996, pages 87 - 96, XP000676263 * |
MEI-HUI YANG ET AL.: "multifunctional ion-exchange stationary phases for HPLC", INT. SYMP. CHROMATOG.,35TH ANNIV. RES. GROUP LIQ. CHROM. JPN, 1995, SINGAPORE, pages 593 - 597, XP000677284 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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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
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DE69701319D1 (en) | 2000-03-30 |
US6432314B1 (en) | 2002-08-13 |
JP2001506915A (en) | 2001-05-29 |
ZA9710466B (en) | 1998-11-20 |
ZA9710468B (en) | 1998-11-20 |
JP4051414B2 (en) | 2008-02-27 |
AU5061198A (en) | 1998-06-10 |
JP4295359B2 (en) | 2009-07-15 |
ZA9710467B (en) | 1998-11-20 |
DE69711913D1 (en) | 2002-05-16 |
WO1998022162A1 (en) | 1998-05-28 |
ATE215971T1 (en) | 2002-04-15 |
EP0939779A1 (en) | 1999-09-08 |
ES2143301T3 (en) | 2000-05-01 |
EP0866815A2 (en) | 1998-09-30 |
US6251964B1 (en) | 2001-06-26 |
EP0866815B1 (en) | 2000-02-23 |
AU728887B2 (en) | 2001-01-18 |
DE69701319T2 (en) | 2000-07-13 |
JP2001504877A (en) | 2001-04-10 |
CA2271132A1 (en) | 1998-05-28 |
EP0866815A3 (en) | 1998-10-21 |
CA2271132C (en) | 2007-04-17 |
WO1998022516A1 (en) | 1998-05-28 |
DE69711913T2 (en) | 2002-10-10 |
ATE189899T1 (en) | 2000-03-15 |
AU5060898A (en) | 1998-06-10 |
EP0939779B1 (en) | 2002-04-10 |
GB9624130D0 (en) | 1997-01-08 |
AU5061098A (en) | 1998-06-10 |
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