JP4051414B2 - 陰イオン交換材料およびその方法 - Google Patents
陰イオン交換材料およびその方法 Download PDFInfo
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- JP4051414B2 JP4051414B2 JP52336498A JP52336498A JP4051414B2 JP 4051414 B2 JP4051414 B2 JP 4051414B2 JP 52336498 A JP52336498 A JP 52336498A JP 52336498 A JP52336498 A JP 52336498A JP 4051414 B2 JP4051414 B2 JP 4051414B2
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- Prior art keywords
- group
- alkylene
- cationic
- groups
- heparin
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 38
- 239000000463 material Substances 0.000 title claims description 23
- 238000005349 anion exchange Methods 0.000 title claims description 4
- 239000000178 monomer Substances 0.000 claims abstract description 75
- 229920000642 polymer Polymers 0.000 claims abstract description 70
- 125000002091 cationic group Chemical group 0.000 claims abstract description 50
- 239000000758 substrate Substances 0.000 claims abstract description 37
- 229920002683 Glycosaminoglycan Polymers 0.000 claims abstract description 9
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 5
- -1 siloxane substituent Chemical group 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000129 anionic group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000005342 ion exchange Methods 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 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
- 150000002500 ions Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 150000001449 anionic compounds Chemical class 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000001165 hydrophobic group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 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
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 3
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- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 2
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000004254 Ammonium phosphate Substances 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims 1
- 235000019289 ammonium phosphates Nutrition 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
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- 125000005496 phosphonium group Chemical group 0.000 claims 1
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- 229920000669 heparin Polymers 0.000 abstract description 82
- 229960002897 heparin Drugs 0.000 abstract description 82
- 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 81
- 230000000694 effects Effects 0.000 abstract description 17
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- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 abstract description 10
- 229920001897 terpolymer Polymers 0.000 abstract description 10
- 229910019142 PO4 Inorganic materials 0.000 abstract description 6
- 239000010452 phosphate Substances 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract description 4
- GYXOHPLRXDQGBP-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.C[N+](C)(C)CCO GYXOHPLRXDQGBP-UHFFFAOYSA-M 0.000 abstract description 3
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- 238000012360 testing method Methods 0.000 description 19
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- 239000002953 phosphate buffered saline Substances 0.000 description 17
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 102000008946 Fibrinogen Human genes 0.000 description 10
- 108010049003 Fibrinogen Proteins 0.000 description 10
- 229940012952 fibrinogen Drugs 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
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- 239000003999 initiator Substances 0.000 description 9
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 9
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- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 125000000837 carbohydrate group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
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- 229940059329 chondroitin sulfate Drugs 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
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- 229920005565 cyclic polymer Polymers 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 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 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
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- 238000007429 general method Methods 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 239000012510 hollow fiber Substances 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 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
- 150000002632 lipids Chemical class 0.000 description 1
- 238000011068 loading method Methods 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
- 239000003208 petroleum Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 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
- 150000003904 phospholipids Chemical class 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
- 229920000307 polymer substrate Polymers 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
- 238000001556 precipitation Methods 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
- 230000006920 protein precipitation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 238000007142 ring opening reaction Methods 0.000 description 1
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- 238000000926 separation method 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
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
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- 229920002554 vinyl polymer Chemical group 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
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)
Applications Claiming Priority (3)
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|---|---|---|---|
| GBGB9624130.2A GB9624130D0 (en) | 1996-11-20 | 1996-11-20 | Biocompatible compositions |
| GB9624130.2 | 1996-11-20 | ||
| PCT/GB1997/003192 WO1998022517A1 (en) | 1996-11-20 | 1997-11-20 | Anion exchange materials and processes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001506915A JP2001506915A (ja) | 2001-05-29 |
| JP2001506915A5 JP2001506915A5 (enExample) | 2005-05-12 |
| JP4051414B2 true JP4051414B2 (ja) | 2008-02-27 |
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| JP52336498A Expired - Fee Related JP4051414B2 (ja) | 1996-11-20 | 1997-11-20 | 陰イオン交換材料およびその方法 |
| JP52336298A Expired - Lifetime JP4295359B2 (ja) | 1996-11-20 | 1997-11-20 | 生体適合性の組成物 |
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| JP52336298A Expired - Lifetime JP4295359B2 (ja) | 1996-11-20 | 1997-11-20 | 生体適合性の組成物 |
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|---|---|
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| EP (2) | EP0939779B1 (enExample) |
| JP (2) | JP4051414B2 (enExample) |
| AT (2) | ATE215971T1 (enExample) |
| AU (3) | AU728887B2 (enExample) |
| CA (1) | CA2271132C (enExample) |
| DE (2) | DE69701319T2 (enExample) |
| ES (1) | ES2143301T3 (enExample) |
| GB (1) | GB9624130D0 (enExample) |
| WO (3) | WO1998022517A1 (enExample) |
| ZA (3) | ZA9710467B (enExample) |
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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 |
| DE60115203T2 (de) * | 2000-01-24 | 2006-08-03 | Biocompatibles Uk Ltd., Farnham | Beschichtete implantate |
| EP1325046B1 (en) | 2000-10-06 | 2007-06-27 | Biocompatibles UK Limited | Zwitterionic polymers |
| GB0100761D0 (en) | 2001-01-11 | 2001-02-21 | Biocompatibles Ltd | Drug delivery from stents |
| 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 |
| AU2003217009A1 (en) | 2002-03-07 | 2003-09-16 | Biocompatibles Uk Limited | Compositions of polymers |
| 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 |
| WO2008064058A2 (en) | 2006-11-21 | 2008-05-29 | Abbott Laboratories | Use of a terpolymer of tetrafluoroethylene, hexafluoropropylene, and vinylidene fluoride in drug eluting coatings |
| US20080286332A1 (en) | 2007-05-14 | 2008-11-20 | Pacetti Stephen D | Implantable medical devices with a topcoat layer of phosphoryl choline acrylate polymer for reduced thrombosis, and improved mechanical properties |
| 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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| SE306597B (enExample) | 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 |
| SE8200751L (sv) | 1982-02-09 | 1983-08-10 | Olle Larm | Forfarande for kovalent koppling for framstellning av konjugat och hervid erhallna produkter |
| SE456347B (sv) | 1982-02-09 | 1988-09-26 | Ird Biomaterial Ab | Ytmodifierat fast substrat samt forfarande for framstellning derav |
| 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 (ja) * | 1989-07-07 | 1999-05-10 | 科学技術振興事業団 | 生体適合性医療デバイス用材料 |
| 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 |
| AU666485B2 (en) * | 1991-07-05 | 1996-02-15 | Biocompatibles Uk Limited | Polymeric surface coatings |
| 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 |
| JPH07505900A (ja) | 1992-04-24 | 1995-06-29 | バイオコンパテイブルズ・リミテツド | 金属皮膜 |
| 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 (ja) | 1993-12-28 | 1995-07-25 | Kuraray Co Ltd | 血液適合性医療用高分子材料および医療材料 |
| JPH07285831A (ja) * | 1994-04-18 | 1995-10-31 | Mitsubishi Chem Corp | 毛髪化粧料組成物 |
-
1996
- 1996-11-20 GB GBGB9624130.2A patent/GB9624130D0/en active Pending
-
1997
- 1997-11-20 ES ES97913308T patent/ES2143301T3/es not_active Expired - Lifetime
- 1997-11-20 US US09/117,729 patent/US6251964B1/en not_active Expired - Lifetime
- 1997-11-20 ZA ZA9710467A patent/ZA9710467B/xx unknown
- 1997-11-20 WO PCT/GB1997/003192 patent/WO1998022517A1/en not_active Ceased
- 1997-11-20 CA CA002271132A patent/CA2271132C/en not_active Expired - Fee Related
- 1997-11-20 JP JP52336498A patent/JP4051414B2/ja not_active Expired - Fee Related
- 1997-11-20 WO PCT/GB1997/003191 patent/WO1998022162A1/en not_active Ceased
- 1997-11-20 DE DE69701319T patent/DE69701319T2/de not_active Expired - Lifetime
- 1997-11-20 US US09/308,496 patent/US6432314B1/en not_active Expired - Lifetime
- 1997-11-20 ZA ZA9710468A patent/ZA9710468B/xx unknown
- 1997-11-20 ZA ZA9710466A patent/ZA9710466B/xx unknown
- 1997-11-20 DE DE69711913T patent/DE69711913T2/de not_active Expired - Lifetime
- 1997-11-20 EP EP97913311A patent/EP0939779B1/en not_active Expired - Lifetime
- 1997-11-20 WO PCT/GB1997/003189 patent/WO1998022516A1/en not_active Ceased
- 1997-11-20 AU AU50608/98A patent/AU728887B2/en not_active Ceased
- 1997-11-20 EP EP97913308A patent/EP0866815B1/en not_active Expired - Lifetime
- 1997-11-20 JP JP52336298A patent/JP4295359B2/ja not_active Expired - Lifetime
- 1997-11-20 AU AU50611/98A patent/AU5061198A/en not_active Abandoned
- 1997-11-20 AU AU50610/98A patent/AU5061098A/en not_active Abandoned
- 1997-11-20 AT AT97913311T patent/ATE215971T1/de not_active IP Right Cessation
- 1997-11-20 AT AT97913308T patent/ATE189899T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69701319T2 (de) | 2000-07-13 |
| ATE189899T1 (de) | 2000-03-15 |
| WO1998022162A1 (en) | 1998-05-28 |
| WO1998022516A1 (en) | 1998-05-28 |
| WO1998022517A1 (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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