JPS63154180A - 抗血栓性医用材料およびその製造法 - Google Patents
抗血栓性医用材料およびその製造法Info
- Publication number
- JPS63154180A JPS63154180A JP61301422A JP30142286A JPS63154180A JP S63154180 A JPS63154180 A JP S63154180A JP 61301422 A JP61301422 A JP 61301422A JP 30142286 A JP30142286 A JP 30142286A JP S63154180 A JPS63154180 A JP S63154180A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy
- group
- heparin
- medical material
- compound
- 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.)
- Granted
Links
- 239000012567 medical material Substances 0.000 title claims description 48
- 238000004519 manufacturing process Methods 0.000 title claims description 26
- 230000002965 anti-thrombogenic effect Effects 0.000 title 1
- 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 92
- 150000001875 compounds Chemical class 0.000 claims description 91
- 229920000669 heparin Polymers 0.000 claims description 79
- 229960002897 heparin Drugs 0.000 claims description 78
- 125000003700 epoxy group Chemical group 0.000 claims description 68
- 239000004593 Epoxy Substances 0.000 claims description 51
- 230000002785 anti-thrombosis Effects 0.000 claims description 46
- 239000000243 solution Substances 0.000 claims description 45
- 239000003146 anticoagulant agent Substances 0.000 claims description 44
- 229920000642 polymer Polymers 0.000 claims description 42
- 239000007864 aqueous solution Substances 0.000 claims description 39
- 125000003277 amino group Chemical group 0.000 claims description 28
- 125000000524 functional group Chemical group 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000002628 heparin derivative Substances 0.000 claims description 16
- 229920001661 Chitosan Polymers 0.000 claims description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 239000007853 buffer solution Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
- 239000004327 boric acid Substances 0.000 claims description 7
- 239000001913 cellulose Substances 0.000 claims description 7
- 229920002678 cellulose Polymers 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 102000008186 Collagen Human genes 0.000 claims description 3
- 108010035532 Collagen Proteins 0.000 claims description 3
- 229920001436 collagen Polymers 0.000 claims description 3
- CYCBPQPFMHUATH-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)butan-1-ol Chemical compound OCCCCOCC1CO1 CYCBPQPFMHUATH-UHFFFAOYSA-N 0.000 claims description 2
- 108010022355 Fibroins Proteins 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 45
- 239000004627 regenerated cellulose Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 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 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 229950003937 tolonium Drugs 0.000 description 6
- 230000007423 decrease Effects 0.000 description 5
- 238000007654 immersion Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 230000014508 negative regulation of coagulation Effects 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000007447 staining method Methods 0.000 description 3
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- GKAMNGMEOQWSHF-UHFFFAOYSA-L potassium;sodium;chloride;hydroxide Chemical compound [OH-].[Na+].[Cl-].[K+] GKAMNGMEOQWSHF-UHFFFAOYSA-L 0.000 description 2
- LJSOLTRJEQZSHV-UHFFFAOYSA-L potassium;sodium;hydron;hydroxide;phosphate Chemical compound [OH-].[Na+].[K+].OP(O)([O-])=O LJSOLTRJEQZSHV-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 108010074860 Factor Xa Proteins 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 238000011481 absorbance measurement Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 239000004019 antithrombin Substances 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000002473 artificial blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
- 229960001008 heparin sodium Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Materials For Medical Uses (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61301422A JPS63154180A (ja) | 1986-12-19 | 1986-12-19 | 抗血栓性医用材料およびその製造法 |
| DE19873786927 DE3786927T2 (de) | 1986-12-03 | 1987-12-02 | Antithrombotische arzneimittel und deren herstellung. |
| PCT/JP1987/000934 WO1988004183A1 (en) | 1986-12-03 | 1987-12-02 | Antithrombotic medical materials and process for their production |
| EP19870907978 EP0336964B1 (en) | 1986-12-03 | 1987-12-02 | Antithrombotic medical materials and process for their production |
| DK430188A DK430188A (da) | 1986-12-03 | 1988-08-02 | Antithrombolisk materiale til medicinsk anvendelse samt fremgangsmaade til fremstilling deraf |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61301422A JPS63154180A (ja) | 1986-12-19 | 1986-12-19 | 抗血栓性医用材料およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63154180A true JPS63154180A (ja) | 1988-06-27 |
| JPH0334739B2 JPH0334739B2 (ko) | 1991-05-23 |
Family
ID=17896683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61301422A Granted JPS63154180A (ja) | 1986-12-03 | 1986-12-19 | 抗血栓性医用材料およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63154180A (ko) |
-
1986
- 1986-12-19 JP JP61301422A patent/JPS63154180A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0334739B2 (ko) | 1991-05-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2342991C (en) | Antithrombogenic surfaces comprising immobilized heparin and methods for producing same | |
| JP4278716B2 (ja) | Ｎ−硫酸化ヒアルロン酸化合物、その誘導体および製造方法 | |
| KR100378109B1 (ko) | 소수성 다중복합 헤파린 결합체, 그의 제조방법 및 용도 | |
| EP0272300B1 (en) | Material of polysaccharides containing carboxyl groups, and a process for producing such polysaccharides | |
| US4871357A (en) | Ionic heparin coating | |
| JPS58147404A (ja) | 共有結合体およびその製造法 | |
| CA2732939A1 (en) | Immobilised biological entities | |
| Larsson et al. | The stability of glutardialdehyde-stabilized 35-heparinized surfaces in contact with blood | |
| EP0580871B1 (en) | Water-soluble cellulose derivative and biocompatible material | |
| EP0231573B1 (en) | Improved ionic heparin coating | |
| JPH05507298A (ja) | 非トロンボゲン性グリコサミノグリカン共重合体 | |
| JPS6341541A (ja) | 表面にキトサン成分を有する高分子成形物及びその製造方法 | |
| WO1988004183A1 (en) | Antithrombotic medical materials and process for their production | |
| JPS63154180A (ja) | 抗血栓性医用材料およびその製造法 | |
| EP0595805B1 (en) | Method of modifying the properties of a substrate surface by covalent bonding of a compound to the surface, and membrane modified according to this method | |
| US20060159650A1 (en) | Composition and method for covalently coupling an antithrombotic substance and a hydrophilic polymer | |
| KR19990038671A (ko) | 혈액적합성 폴리우레탄-친수성 고분자 블랜드 | |
| JPH08336587A (ja) | 医療用材料及びその製造方法 | |
| JP4258703B2 (ja) | 血液適合性組成物およびそれをコートした医療用具 | |
| JPH04197264A (ja) | 抗血栓性医療材料の製造方法および抗血栓性医療材料を備えた医療用器具 | |
| JPH0337073A (ja) | 抗血栓性医療材料およびその製法 | |
| JPS5810053A (ja) | 血液接触医療器の製造方法および血液接触医療器 | |
| JPS63139901A (ja) | ヘパリン誘導体およびその製造法 | |
| JPH04312467A (ja) | 抗血栓性医用材料、医用器具および抗血栓性医用材料の製造方法 | |
| JPH07178160A (ja) | 医療用材料の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |