CA2732939C - Immobilised biological entities - Google Patents
Immobilised biological entities Download PDFInfo
- Publication number
- CA2732939C CA2732939C CA2732939A CA2732939A CA2732939C CA 2732939 C CA2732939 C CA 2732939C CA 2732939 A CA2732939 A CA 2732939A CA 2732939 A CA2732939 A CA 2732939A CA 2732939 C CA2732939 C CA 2732939C
- Authority
- CA
- Canada
- Prior art keywords
- heparin
- functionalized
- medical device
- cationic polymer
- polyamine
- 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.)
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- 239000008280 blood Substances 0.000 claims abstract description 31
- 210000004369 blood Anatomy 0.000 claims abstract description 31
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 14
- 239000011247 coating layer Substances 0.000 claims abstract description 14
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 13
- 230000015271 coagulation Effects 0.000 claims abstract description 11
- 238000005345 coagulation Methods 0.000 claims abstract description 11
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical group 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 description 199
- 229920000669 heparin Polymers 0.000 claims description 196
- 229960002897 heparin Drugs 0.000 claims description 193
- 229920000768 polyamine Polymers 0.000 claims description 61
- 239000010410 layer Substances 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 55
- 150000001345 alkine derivatives Chemical class 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 229920006317 cationic polymer Polymers 0.000 claims description 45
- 150000001540 azides Chemical class 0.000 claims description 39
- 230000001453 nonthrombogenic effect Effects 0.000 claims description 36
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 29
- 150000004804 polysaccharides Chemical class 0.000 claims description 27
- 230000027455 binding Effects 0.000 claims description 25
- 229920001282 polysaccharide Polymers 0.000 claims description 25
- 239000005017 polysaccharide Substances 0.000 claims description 25
- 125000002355 alkine group Chemical group 0.000 claims description 23
- 238000000576 coating method Methods 0.000 claims description 22
- 239000011248 coating agent Substances 0.000 claims description 19
- 229920006318 anionic polymer Polymers 0.000 claims description 18
- 239000002344 surface layer Substances 0.000 claims description 17
- 229920001586 anionic polysaccharide Polymers 0.000 claims description 11
- 150000004836 anionic polysaccharides Chemical class 0.000 claims description 11
- 102000004411 Antithrombin III Human genes 0.000 claims description 8
- 108090000935 Antithrombin III Proteins 0.000 claims description 8
- 229960005348 antithrombin iii Drugs 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 229960000633 dextran sulfate Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 238000002513 implantation Methods 0.000 claims description 3
- 229920000592 inorganic polymer Polymers 0.000 claims description 2
- 229920000620 organic polymer Polymers 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 238000002360 preparation method Methods 0.000 description 27
- 239000004019 antithrombin Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- 229920001223 polyethylene glycol Polymers 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 150000003852 triazoles Chemical class 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 238000007306 functionalization reaction Methods 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- -1 alkaline earth metal salts Chemical class 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 125000006850 spacer group Chemical group 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000003146 anticoagulant agent Substances 0.000 description 15
- 229940127219 anticoagulant drug Drugs 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000004800 polyvinyl chloride Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 11
- 229910052737 gold Inorganic materials 0.000 description 11
- 239000010931 gold Substances 0.000 description 11
- 125000005647 linker group Chemical group 0.000 description 11
- 229920000915 polyvinyl chloride Polymers 0.000 description 11
- 238000004659 sterilization and disinfection Methods 0.000 description 11
- 239000008213 purified water Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000000502 dialysis Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 235000010378 sodium ascorbate Nutrition 0.000 description 8
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 8
- 229960005055 sodium ascorbate Drugs 0.000 description 8
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 8
- 230000001954 sterilising effect Effects 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- KNEPBZMJMJUNQX-UHFFFAOYSA-N pent-4-ynamide Chemical compound NC(=O)CCC#C KNEPBZMJMJUNQX-UHFFFAOYSA-N 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000001720 carbohydrates Chemical group 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 230000037452 priming Effects 0.000 description 5
- WAGMYTXJRVPMGW-UHFFFAOYSA-N 4-azidobutanoic acid Chemical compound OC(=O)CCCN=[N+]=[N-] WAGMYTXJRVPMGW-UHFFFAOYSA-N 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- KQHKSGRIBYJYFX-UHFFFAOYSA-J Ponceau S Chemical compound [Na+].[Na+].[Na+].[Na+].Oc1c(cc2cc(ccc2c1N=Nc1ccc(cc1S([O-])(=O)=O)N=Nc1ccc(cc1)S([O-])(=O)=O)S([O-])(=O)=O)S([O-])(=O)=O KQHKSGRIBYJYFX-UHFFFAOYSA-J 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 125000003172 aldehyde group Chemical group 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920000295 expanded polytetrafluoroethylene Polymers 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- YLGNQZKAFVRMHJ-UHFFFAOYSA-N n-[4-(2-aminooxyethyl)phenyl]pent-4-ynamide Chemical compound NOCCC1=CC=C(NC(=O)CCC#C)C=C1 YLGNQZKAFVRMHJ-UHFFFAOYSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 3
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 3
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 3
- 239000004812 Fluorinated ethylene propylene Substances 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229920002873 Polyethylenimine Polymers 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 108090000190 Thrombin Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003114 blood coagulation factor Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 229920001903 high density polyethylene Polymers 0.000 description 3
- 229940063583 high-density polyethylene Drugs 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 3
- HEFNUGVGRLEKEA-UHFFFAOYSA-N n-[4-(2-hydroxyethyl)phenyl]pent-4-ynamide Chemical compound OCCC1=CC=C(NC(=O)CCC#C)C=C1 HEFNUGVGRLEKEA-UHFFFAOYSA-N 0.000 description 3
- 229910001000 nickel titanium Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229920009441 perflouroethylene propylene Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 229960004072 thrombin Drugs 0.000 description 3
- 230000002885 thrombogenetic effect Effects 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 239000011800 void material Substances 0.000 description 3
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 2
- PADMHRRSXNQELF-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;pent-4-ynoic acid Chemical compound OC(=O)CCC#C.ON1C(=O)CCC1=O PADMHRRSXNQELF-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229920002683 Glycosaminoglycan Polymers 0.000 description 2
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 229920002593 Polyethylene Glycol 800 Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 108091006629 SLC13A2 Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 210000003484 anatomy Anatomy 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000000337 buffer salt Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 150000004676 glycans Polymers 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003055 low molecular weight heparin Substances 0.000 description 2
- 229940127215 low-molecular weight heparin Drugs 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- HLXZNVUGXRDIFK-UHFFFAOYSA-N nickel titanium Chemical compound [Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni] HLXZNVUGXRDIFK-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001643 poly(ether ketone) Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 238000003380 quartz crystal microbalance Methods 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 229950003937 tolonium Drugs 0.000 description 2
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 2
- 238000009827 uniform distribution Methods 0.000 description 2
- OHJKXVLJWUPWQG-IUYNYSEKSA-J (4s,6r)-6-[(2r,4r)-4,6-dihydroxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)oxan-3-yl]oxy-3,4-dihydroxy-5-sulfonatooxyoxane-2-carboxylate Chemical compound O[C@@H]1C(NS([O-])(=O)=O)C(O)O[C@H](COS([O-])(=O)=O)C1O[C@H]1C(OS([O-])(=O)=O)[C@@H](O)C(O)C(C([O-])=O)O1 OHJKXVLJWUPWQG-IUYNYSEKSA-J 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- JTEJPPKMYBDEMY-UHFFFAOYSA-N 5-methoxytryptamine Chemical compound COC1=CC=C2NC=C(CCN)C2=C1 JTEJPPKMYBDEMY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000252506 Characiformes Species 0.000 description 1
- 102000000405 Clarin Human genes 0.000 description 1
- 108050008883 Clarin Proteins 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- 229910000684 Cobalt-chrome Inorganic materials 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010074860 Factor Xa Proteins 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 229920000544 Gore-Tex Polymers 0.000 description 1
- 229920002971 Heparan sulfate Polymers 0.000 description 1
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| WO2014152423A1 (en) * | 2013-03-15 | 2014-09-25 | Bard Access Systems, Inc. | Antithrombic coatings and uses thereof |
| CA2925858A1 (en) * | 2013-09-30 | 2015-04-02 | Teleflex Medical Incorporated | Stabilized enzyme compositions |
| US9795721B2 (en) | 2013-11-28 | 2017-10-24 | Toray Industries, Inc. | Antithrombotic material |
| US11839698B2 (en) | 2014-03-13 | 2023-12-12 | W. L. Gore & Associates, Inc. | Drug composition and coating |
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| EP4032560A1 (en) * | 2021-01-25 | 2022-07-27 | Centre National pour la Recherche Scientifique | Implantable material in contact with blood and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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2008
- 2008-09-15 GB GBGB0816783.5A patent/GB0816783D0/en not_active Ceased
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2009
- 2009-09-15 EP EP09783061.6A patent/EP2340057B1/en active Active
- 2009-09-15 AU AU2009290833A patent/AU2009290833B2/en active Active
- 2009-09-15 CA CA2732939A patent/CA2732939C/en active Active
- 2009-09-15 US US12/559,660 patent/US8992963B2/en active Active
- 2009-09-15 JP JP2011526514A patent/JP5775454B2/ja active Active
- 2009-09-15 ES ES09783061.6T patent/ES2550147T3/es active Active
- 2009-09-15 WO PCT/EP2009/061981 patent/WO2010029189A2/en not_active Ceased
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| Publication number | Publication date |
|---|---|
| AU2009290833A1 (en) | 2010-03-18 |
| US20100074938A1 (en) | 2010-03-25 |
| US20180326118A1 (en) | 2018-11-15 |
| US10064978B2 (en) | 2018-09-04 |
| JP2015147051A (ja) | 2015-08-20 |
| EP2340057A2 (en) | 2011-07-06 |
| AU2009290833B2 (en) | 2015-05-07 |
| JP2012502678A (ja) | 2012-02-02 |
| JP6122052B2 (ja) | 2017-04-26 |
| US8992963B2 (en) | 2015-03-31 |
| US20150045508A1 (en) | 2015-02-12 |
| WO2010029189A3 (en) | 2011-03-03 |
| EP2340057B1 (en) | 2015-07-22 |
| WO2010029189A2 (en) | 2010-03-18 |
| ES2550147T3 (es) | 2015-11-04 |
| JP5775454B2 (ja) | 2015-09-09 |
| HK1159530A1 (en) | 2012-08-03 |
| CA2732939A1 (en) | 2010-03-18 |
| GB0816783D0 (en) | 2008-10-22 |
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