DE69701319T2 - Bioverträgliche zusammensetzungen - Google Patents
Bioverträgliche zusammensetzungenInfo
- Publication number
- DE69701319T2 DE69701319T2 DE69701319T DE69701319T DE69701319T2 DE 69701319 T2 DE69701319 T2 DE 69701319T2 DE 69701319 T DE69701319 T DE 69701319T DE 69701319 T DE69701319 T DE 69701319T DE 69701319 T2 DE69701319 T2 DE 69701319T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- heparin
- groups
- polymer
- formula
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 25
- 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 claims abstract description 99
- 229920000669 heparin Polymers 0.000 claims abstract description 98
- 229960002897 heparin Drugs 0.000 claims abstract description 98
- 239000000178 monomer Substances 0.000 claims abstract description 84
- 229920000642 polymer Polymers 0.000 claims abstract description 73
- 125000002091 cationic group Chemical group 0.000 claims abstract description 50
- 239000000758 substrate Substances 0.000 claims abstract description 29
- 229920001897 terpolymer Polymers 0.000 claims abstract description 29
- 229920002683 Glycosaminoglycan Polymers 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 15
- 239000008199 coating composition Substances 0.000 claims abstract description 3
- 238000000576 coating method Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229920006296 quaterpolymer Polymers 0.000 claims description 13
- -1 siloxane substituent Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000129 anionic group Chemical group 0.000 claims description 12
- 238000004132 cross linking Methods 0.000 claims description 11
- 125000000962 organic group Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001165 hydrophobic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 2
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 2
- 229920001287 Chondroitin sulfate Polymers 0.000 claims description 2
- 102000007625 Hirudins Human genes 0.000 claims description 2
- 108010007267 Hirudins Proteins 0.000 claims description 2
- 229940072056 alginate Drugs 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229940059329 chondroitin sulfate Drugs 0.000 claims description 2
- 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 claims description 2
- 229940006607 hirudin Drugs 0.000 claims description 2
- 229920002674 hyaluronan Polymers 0.000 claims description 2
- 229960003160 hyaluronic acid Drugs 0.000 claims description 2
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims description 2
- 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
- 210000004369 blood Anatomy 0.000 abstract description 17
- 239000008280 blood Substances 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 17
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 abstract description 9
- 229910019142 PO4 Inorganic materials 0.000 abstract description 5
- 239000010452 phosphate Substances 0.000 abstract description 5
- 150000003839 salts Chemical class 0.000 abstract description 5
- 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
- 230000002209 hydrophobic effect Effects 0.000 abstract description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract description 3
- 239000002607 heparin antagonist Substances 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 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 20
- 239000002953 phosphate buffered saline Substances 0.000 description 20
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 20
- 239000011248 coating agent Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 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
- 239000003999 initiator Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 9
- 229940011051 isopropyl acetate Drugs 0.000 description 9
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 9
- 238000001179 sorption measurement Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000011877 solvent mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000001772 blood platelet Anatomy 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 230000010412 perfusion Effects 0.000 description 5
- 230000002965 anti-thrombogenic effect Effects 0.000 description 4
- 239000003146 anticoagulant agent Substances 0.000 description 4
- 229940127219 anticoagulant drug Drugs 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000000975 bioactive effect Effects 0.000 description 3
- 239000013060 biological fluid Substances 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
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- 238000002156 mixing Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000002572 peristaltic effect Effects 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
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- 229920001155 polypropylene Polymers 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 3
- NJNWCIAPVGRBHO-UHFFFAOYSA-N 2-hydroxyethyl-dimethyl-[(oxo-$l^{5}-phosphanylidyne)methyl]azanium Chemical group OCC[N+](C)(C)C#P=O NJNWCIAPVGRBHO-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 239000004593 Epoxy Chemical group 0.000 description 2
- 108010074860 Factor Xa Proteins 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 102000007562 Serum Albumin Human genes 0.000 description 2
- 108010071390 Serum Albumin Proteins 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
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- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 2
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- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
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- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 description 1
- LUYAMNYBNTVQJG-UHFFFAOYSA-N 1-chloro-2-(2-chloroethylsulfonyl)ethane Chemical group ClCCS(=O)(=O)CCCl LUYAMNYBNTVQJG-UHFFFAOYSA-N 0.000 description 1
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- MBGPMDXXPUWUIJ-UHFFFAOYSA-N 11-bromoundecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCBr MBGPMDXXPUWUIJ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- FIYLNTKHSCVZBK-UHFFFAOYSA-N 2-(2,5-dioxopyrrolidin-1-yl)-4-methylbenzenesulfonic acid Chemical compound CC1=CC(=C(C=C1)S(=O)(=O)O)N2C(=O)CCC2=O FIYLNTKHSCVZBK-UHFFFAOYSA-N 0.000 description 1
- RMAJLHJNKOQFRG-UHFFFAOYSA-N 3-dodecyl-2-methylpentadec-2-enoic acid Chemical compound CCCCCCCCCCCCC(=C(C)C(O)=O)CCCCCCCCCCCC RMAJLHJNKOQFRG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 101100173726 Arabidopsis thaliana OR23 gene Proteins 0.000 description 1
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- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 108010007568 Protamines Proteins 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
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- 239000005864 Sulphur Substances 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
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- 229920006243 acrylic copolymer Polymers 0.000 description 1
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- 238000013019 agitation Methods 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000005275 alkylenearyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 230000002785 anti-thrombosis Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- RIIWUGSYXOBDMC-UHFFFAOYSA-N benzene-1,2-diamine;hydron;dichloride Chemical compound Cl.Cl.NC1=CC=CC=C1N RIIWUGSYXOBDMC-UHFFFAOYSA-N 0.000 description 1
- 229910001423 beryllium ion Inorganic materials 0.000 description 1
- 229920000249 biocompatible polymer Polymers 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 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
- 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
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000011888 foil 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
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000001963 growth medium Substances 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229940106780 human fibrinogen 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000009629 microbiological culture Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 238000011056 performance test Methods 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
- 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
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 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
- 239000008259 solid foam Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 238000004448 titration Methods 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
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000005406 washing Methods 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
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9624130.2A GB9624130D0 (en) | 1996-11-20 | 1996-11-20 | Biocompatible compositions |
| PCT/GB1997/003189 WO1998022516A1 (en) | 1996-11-20 | 1997-11-20 | Biocompatible compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69701319D1 DE69701319D1 (de) | 2000-03-30 |
| DE69701319T2 true DE69701319T2 (de) | 2000-07-13 |
Family
ID=10803229
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69701319T Expired - Lifetime DE69701319T2 (de) | 1996-11-20 | 1997-11-20 | Bioverträgliche zusammensetzungen |
| DE69711913T Expired - Lifetime DE69711913T2 (de) | 1996-11-20 | 1997-11-20 | Anionenaustauschmaterialien und verfahren |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69711913T Expired - Lifetime DE69711913T2 (de) | 1996-11-20 | 1997-11-20 | Anionenaustauschmaterialien und verfahren |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6251964B1 (OSRAM) |
| EP (2) | EP0939779B1 (OSRAM) |
| JP (2) | JP4051414B2 (OSRAM) |
| AT (2) | ATE215971T1 (OSRAM) |
| AU (3) | AU728887B2 (OSRAM) |
| CA (1) | CA2271132C (OSRAM) |
| DE (2) | DE69701319T2 (OSRAM) |
| ES (1) | ES2143301T3 (OSRAM) |
| GB (1) | GB9624130D0 (OSRAM) |
| WO (3) | WO1998022517A1 (OSRAM) |
| ZA (3) | ZA9710467B (OSRAM) |
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| 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 |
| DE69939469D1 (de) | 1998-07-07 | 2008-10-16 | Nof Corp | Zusammensetzung zur wundheilung, wundverband und verfahren zur behandlung vonwunden |
| WO2000035980A1 (en) * | 1998-12-11 | 2000-06-22 | Biocompatibles Limited | Crosslinked polymers and refractive devices formed therefrom |
| EP1180013B1 (en) * | 1999-05-27 | 2006-03-08 | Biocompatibles UK Limited | Local drug delivery |
| EP1189956B1 (en) * | 1999-05-27 | 2003-07-23 | Biocompatibles UK Limited | Polymer solutions |
| ATE310542T1 (de) * | 2000-01-24 | 2005-12-15 | Biocompatibles Uk Ltd | Beschichtete implantate |
| DE60129148T2 (de) | 2000-10-06 | 2008-02-28 | Biocompatibles Uk Ltd., Farnham | Zwitterionische polymere |
| GB0100761D0 (en) | 2001-01-11 | 2001-02-21 | Biocompatibles Ltd | Drug delivery from stents |
| EP1391519B1 (en) * | 2001-04-26 | 2006-10-25 | Nof Corporation | Nonspecific hybridization inhibitors, clinical diagnostic reagents, and method of clinical analysis |
| 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 |
| US7892284B2 (en) * | 2005-02-28 | 2011-02-22 | Hoya Corporation | Intraocular lens and process for producing the same |
| 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 |
| JP5557373B2 (ja) | 2006-11-21 | 2014-07-23 | アボット ラボラトリーズ | 薬剤溶出性コーティングにおけるテトラフルオロエチレン、ヘキサフルオロプロピレン、及びフッ化ビニリデンのターポリマーの使用 |
| 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 |
| US8308699B2 (en) * | 2008-12-05 | 2012-11-13 | Semprus Biosciences Corp. | Layered non-fouling, antimicrobial antithrombogenic coatings |
| KR20130110143A (ko) | 2010-06-09 | 2013-10-08 | 셈프러스 바이오사이언시스 코퍼레이션 | 방오성, 항균성, 항혈전성 그라프트-프롬 조성물 |
| US20110305898A1 (en) | 2010-06-09 | 2011-12-15 | Zheng Zhang | Non-fouling, anti-microbial, anti-thrombogenic graft compositions |
| US8519189B2 (en) | 2011-06-01 | 2013-08-27 | University Of British Columbia | Polymers for reversing heparin-based anticoagulation |
| EP2791214A4 (en) | 2011-12-14 | 2015-11-04 | Semprus Biosciences Corp | REDOX PROCESS FOR CONTACT LENS MODIFICATION |
| MX2014007203A (es) | 2011-12-14 | 2015-04-14 | Semprus Biosciences Corp | Proceso de imbibicion para modificacion de superficie de lente de contacto. |
| MX2014007202A (es) | 2011-12-14 | 2015-03-09 | Semprus Biosciences Corp | Lentes de contacto modificadas en la superficie. |
| MX2014007211A (es) | 2011-12-14 | 2015-04-14 | Semprus Biosciences Corp | Lente de contacto de hidrogel de silicona modificada usando oxidantes de lantanido o de metal de transicion. |
| WO2013090801A1 (en) | 2011-12-14 | 2013-06-20 | Semprus Biosciences Corp. | Multistep uv process to create surface modified contact lenses |
| 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 |
| CN105283521B (zh) * | 2013-05-27 | 2018-05-11 | Jsr株式会社 | 由无机材料构成的表面用的表面处理剂、表面被改性的器具和装置、该器具和装置的制造方法 |
| 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 |
| KR20240020716A (ko) | 2021-05-27 | 2024-02-15 | 메트로 인터내셔널 바이오테크 엘엘씨 | 니코틴산 모노뉴클레오타이드 및 이의 에스터의 결정질 고체 및 제조 및 사용 방법 |
| 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 (OSRAM) | 1964-12-17 | 1968-12-02 | Incentive Ab | |
| US3861948A (en) | 1972-05-22 | 1975-01-21 | Kendall & Co | Pressure sensitive adhesive tape |
| ZA733409B (en) * | 1972-05-31 | 1974-05-29 | Commw Scient Ind Res Org | A process of manufacturing ion-exchange resins |
| SE456347B (sv) | 1982-02-09 | 1988-09-26 | Ird Biomaterial Ab | Ytmodifierat fast substrat samt forfarande for framstellning derav |
| SE8200751L (sv) | 1982-02-09 | 1983-08-10 | Olle Larm | Forfarande for kovalent koppling for framstellning av konjugat och hervid erhallna produkter |
| 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 |
| RU2167886C2 (ru) * | 1991-07-05 | 2001-05-27 | Биокомпэтиблз Лимитед. | Полимер, способ получения полимера, поверхность с покрытием, способ покрытия поверхности |
| 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 |
| CA2118496C (en) | 1992-04-24 | 2005-01-11 | Roger Randall Charles New | 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 (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 ZA ZA9710467A patent/ZA9710467B/xx unknown
- 1997-11-20 WO PCT/GB1997/003192 patent/WO1998022517A1/en not_active Ceased
- 1997-11-20 AT AT97913311T patent/ATE215971T1/de not_active IP Right Cessation
- 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 WO PCT/GB1997/003189 patent/WO1998022516A1/en not_active Ceased
- 1997-11-20 WO PCT/GB1997/003191 patent/WO1998022162A1/en not_active Ceased
- 1997-11-20 JP JP52336498A patent/JP4051414B2/ja not_active Expired - Fee Related
- 1997-11-20 ZA ZA9710468A patent/ZA9710468B/xx unknown
- 1997-11-20 EP EP97913311A patent/EP0939779B1/en not_active Expired - Lifetime
- 1997-11-20 DE DE69701319T patent/DE69701319T2/de not_active Expired - Lifetime
- 1997-11-20 AT AT97913308T patent/ATE189899T1/de not_active IP Right Cessation
- 1997-11-20 EP EP97913308A patent/EP0866815B1/en not_active Expired - Lifetime
- 1997-11-20 DE DE69711913T patent/DE69711913T2/de not_active Expired - Lifetime
- 1997-11-20 US US09/308,496 patent/US6432314B1/en not_active Expired - Lifetime
- 1997-11-20 AU AU50608/98A patent/AU728887B2/en not_active Ceased
- 1997-11-20 AU AU50611/98A patent/AU5061198A/en not_active Abandoned
- 1997-11-20 CA CA002271132A patent/CA2271132C/en not_active Expired - Fee Related
- 1997-11-20 AU AU50610/98A patent/AU5061098A/en not_active Abandoned
- 1997-11-20 JP JP52336298A patent/JP4295359B2/ja not_active Expired - Lifetime
- 1997-11-20 ZA ZA9710466A patent/ZA9710466B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6251964B1 (en) | 2001-06-26 |
| EP0866815B1 (en) | 2000-02-23 |
| AU728887B2 (en) | 2001-01-18 |
| EP0939779A1 (en) | 1999-09-08 |
| US6432314B1 (en) | 2002-08-13 |
| JP2001504877A (ja) | 2001-04-10 |
| ES2143301T3 (es) | 2000-05-01 |
| WO1998022516A1 (en) | 1998-05-28 |
| EP0866815A3 (en) | 1998-10-21 |
| EP0939779B1 (en) | 2002-04-10 |
| AU5061098A (en) | 1998-06-10 |
| ZA9710468B (en) | 1998-11-20 |
| WO1998022517A1 (en) | 1998-05-28 |
| GB9624130D0 (en) | 1997-01-08 |
| WO1998022162A1 (en) | 1998-05-28 |
| DE69701319D1 (de) | 2000-03-30 |
| ZA9710467B (en) | 1998-11-20 |
| ZA9710466B (en) | 1998-11-20 |
| AU5060898A (en) | 1998-06-10 |
| ATE215971T1 (de) | 2002-04-15 |
| ATE189899T1 (de) | 2000-03-15 |
| EP0866815A2 (en) | 1998-09-30 |
| JP4295359B2 (ja) | 2009-07-15 |
| CA2271132A1 (en) | 1998-05-28 |
| JP2001506915A (ja) | 2001-05-29 |
| DE69711913D1 (de) | 2002-05-16 |
| AU5061198A (en) | 1998-06-10 |
| DE69711913T2 (de) | 2002-10-10 |
| CA2271132C (en) | 2007-04-17 |
| JP4051414B2 (ja) | 2008-02-27 |
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