CA1171593A - Polyaminic resin for the selective separation of heparin from other glucosaminoglycanes and method for the preparation thereof - Google Patents
Polyaminic resin for the selective separation of heparin from other glucosaminoglycanes and method for the preparation thereofInfo
- Publication number
- CA1171593A CA1171593A CA000375254A CA375254A CA1171593A CA 1171593 A CA1171593 A CA 1171593A CA 000375254 A CA000375254 A CA 000375254A CA 375254 A CA375254 A CA 375254A CA 1171593 A CA1171593 A CA 1171593A
- Authority
- CA
- Canada
- Prior art keywords
- heparin
- resin
- crosslinking
- diisocyanate
- solution
- 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
Links
- 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 title claims abstract description 47
- 229920000669 heparin Polymers 0.000 title claims abstract description 47
- 229960002897 heparin Drugs 0.000 title claims abstract description 47
- 239000011347 resin Substances 0.000 title claims abstract description 38
- 229920005989 resin Polymers 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims description 18
- 238000000926 separation method Methods 0.000 title abstract description 10
- 238000002360 preparation method Methods 0.000 title description 4
- 238000004132 cross linking Methods 0.000 claims abstract description 24
- 239000000243 solution Substances 0.000 claims abstract description 22
- 229920002873 Polyethylenimine Polymers 0.000 claims abstract description 15
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 230000000295 complement effect Effects 0.000 claims abstract description 6
- 239000011780 sodium chloride Substances 0.000 claims abstract description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- 238000001179 sorption measurement Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 239000003957 anion exchange resin Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000000502 dialysis Methods 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 abstract description 7
- 238000000605 extraction Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000000129 anionic group Chemical group 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 229920002971 Heparan sulfate Polymers 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920002683 Glycosaminoglycan Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001962 electrophoresis Methods 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 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 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 description 2
- 102100025597 Caspase-4 Human genes 0.000 description 2
- 229920001287 Chondroitin sulfate Polymers 0.000 description 2
- 229920000045 Dermatan sulfate Polymers 0.000 description 2
- 101100273284 Homo sapiens CASP4 gene Proteins 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940059329 chondroitin sulfate Drugs 0.000 description 2
- AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 description 2
- 229940051593 dermatan sulfate Drugs 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229920002674 hyaluronan Polymers 0.000 description 2
- 229960003160 hyaluronic acid Drugs 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229920000447 polyanionic polymer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GVESKLRPSXPGCH-UHFFFAOYSA-N 3,4,5-trichloro-2h-thiazine Chemical compound ClC1=C(Cl)C(Cl)=CSN1 GVESKLRPSXPGCH-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000333 poly(propyleneimine) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011158 quantitative evaluation Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- 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 1
- -1 trichlorothiazine Chemical class 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
- C08G18/6423—Polyalkylene polyamines; polyethylenimines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyurethanes Or Polyureas (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21499/80A IT1141483B (it) | 1980-04-18 | 1980-04-18 | Resina poliamminica per la separazione selettiva di eparina da altri glucosamminoglicani e procedimento per la sua preparazione |
| IT21499A/80 | 1980-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1171593A true CA1171593A (en) | 1984-07-24 |
Family
ID=11182721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000375254A Expired CA1171593A (en) | 1980-04-18 | 1981-04-10 | Polyaminic resin for the selective separation of heparin from other glucosaminoglycanes and method for the preparation thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4369256A (OSRAM) |
| JP (1) | JPS56163148A (OSRAM) |
| BE (1) | BE888463A (OSRAM) |
| CA (1) | CA1171593A (OSRAM) |
| CH (1) | CH651841A5 (OSRAM) |
| DE (1) | DE3115245A1 (OSRAM) |
| FR (1) | FR2480760B1 (OSRAM) |
| GB (1) | GB2074178B (OSRAM) |
| IT (1) | IT1141483B (OSRAM) |
| NL (1) | NL189863C (OSRAM) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0124676A1 (en) * | 1983-05-04 | 1984-11-14 | IRD-Biomaterial AB | A surface modified solid substrate and a method for its preparation |
| US4801475A (en) * | 1984-08-23 | 1989-01-31 | Gregory Halpern | Method of hydrophilic coating of plastics |
| US4663233A (en) * | 1985-10-24 | 1987-05-05 | Universal High Technologies | Lens with hydrophilic coating |
| FR2641281B1 (fr) * | 1989-01-05 | 1993-05-14 | Saduc Developp Utilisations Cu | Procede de purification de polymeres naturels ou synthetiques en solution, hydrosolubles ou solubles en milieu hydro-alcoolique comportant des groupements sulfates |
| JPH02105462U (OSRAM) * | 1989-02-08 | 1990-08-22 | ||
| US6197289B1 (en) * | 1997-07-01 | 2001-03-06 | Terumo Cardiovascular Systems Corporation | Removal of biologically active agents |
| US6146771A (en) * | 1997-07-01 | 2000-11-14 | Terumo Cardiovascular Systems Corporation | Process for modifying surfaces using the reaction product of a water-insoluble polymer and a polyalkylene imine |
| US20030069601A1 (en) * | 1998-12-15 | 2003-04-10 | Closys Corporation | Clotting cascade initiating apparatus and methods of use |
| ITMI20032498A1 (it) | 2003-12-17 | 2005-06-18 | Pasqua Anna Oreste | Polisaccaridi antitrombotici a basso peso molecolare e |
| EP1393394B1 (en) | 2000-12-29 | 2006-11-22 | The University of Oklahoma | Conductive polyamine-based electrolyte |
| ITMI20010397A1 (it) * | 2001-02-27 | 2002-08-27 | Giorgio Zoppetti | Derivati altamente n,o-solfatati del polisaccaride k5 e loro preparazione |
| DE60334617D1 (de) * | 2002-06-18 | 2010-12-02 | Glycores 2000 Srl | Epimerderivate von k5-polysaccharid mit hohem sulfatierungsgrad |
| US8513407B2 (en) * | 2002-06-18 | 2013-08-20 | Glycores 2000 S.R.L. | Process for the preparation of N-acyl-(epi)K5-amine-O-sulfate-derivatives and products thus obtained |
| WO2009108845A2 (en) * | 2008-02-28 | 2009-09-03 | Virginia Commonwealth University | Method for finger-printing heparins |
| JP5560808B2 (ja) * | 2010-03-23 | 2014-07-30 | 住友ベークライト株式会社 | 酸性糖鎖捕捉用基材 |
| CN104190383A (zh) * | 2014-08-22 | 2014-12-10 | 南京农业大学 | 一种低分子量肝素亲和纯化介质和纯化低分子量肝素方法 |
| CN112390947B (zh) * | 2019-08-16 | 2023-04-28 | 位速科技股份有限公司 | 电极界面层材料、两性离子聚合物和有机光伏元件 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL51867C (OSRAM) * | 1939-02-22 | |||
| NL282900A (OSRAM) * | 1961-09-22 | 1900-01-01 | ||
| US3325346A (en) * | 1964-06-26 | 1967-06-13 | Chemirad Corp | Process of making paper using reaction product of polyethyleneimine and polyisocyanate |
| JPS4928914A (OSRAM) * | 1972-07-17 | 1974-03-14 | ||
| CH590179A5 (OSRAM) * | 1973-11-08 | 1977-07-29 | Ciba Geigy Ag |
-
1980
- 1980-04-18 IT IT21499/80A patent/IT1141483B/it active
-
1981
- 1981-04-06 US US06/251,874 patent/US4369256A/en not_active Expired - Lifetime
- 1981-04-07 GB GB8110831A patent/GB2074178B/en not_active Expired
- 1981-04-10 CA CA000375254A patent/CA1171593A/en not_active Expired
- 1981-04-13 FR FR8107339A patent/FR2480760B1/fr not_active Expired
- 1981-04-15 CH CH2545/81A patent/CH651841A5/it not_active IP Right Cessation
- 1981-04-15 NL NLAANVRAGE8101864,A patent/NL189863C/xx not_active IP Right Cessation
- 1981-04-15 DE DE19813115245 patent/DE3115245A1/de active Granted
- 1981-04-16 BE BE0/204523A patent/BE888463A/fr not_active IP Right Cessation
- 1981-04-16 JP JP5780581A patent/JPS56163148A/ja active Granted
-
1982
- 1982-09-29 US US06/431,732 patent/US4411796A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2074178A (en) | 1981-10-28 |
| US4369256A (en) | 1983-01-18 |
| FR2480760B1 (fr) | 1986-02-07 |
| JPS56163148A (en) | 1981-12-15 |
| IT8021499A0 (it) | 1980-04-18 |
| NL189863C (nl) | 1993-08-16 |
| DE3115245A1 (de) | 1982-04-01 |
| NL189863B (nl) | 1993-03-16 |
| BE888463A (fr) | 1981-08-17 |
| FR2480760A1 (fr) | 1981-10-23 |
| US4411796A (en) | 1983-10-25 |
| NL8101864A (nl) | 1981-11-16 |
| CH651841A5 (it) | 1985-10-15 |
| DE3115245C2 (OSRAM) | 1988-09-15 |
| GB2074178B (en) | 1984-04-18 |
| JPH0253453B2 (OSRAM) | 1990-11-16 |
| IT1141483B (it) | 1986-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |