DE1195010B - Verfahren zur Reinigung von Heparin nach der Chromatographischen Methode - Google Patents
Verfahren zur Reinigung von Heparin nach der Chromatographischen MethodeInfo
- Publication number
- DE1195010B DE1195010B DEO8745A DEO0008745A DE1195010B DE 1195010 B DE1195010 B DE 1195010B DE O8745 A DEO8745 A DE O8745A DE O0008745 A DEO0008745 A DE O0008745A DE 1195010 B DE1195010 B DE 1195010B
- Authority
- DE
- Germany
- Prior art keywords
- heparin
- elution
- adsorption
- resin
- concentration
- 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
- 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 description 30
- 229960002897 heparin Drugs 0.000 title claims description 30
- 229920000669 heparin Polymers 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 19
- 238000004587 chromatography analysis Methods 0.000 title description 2
- 239000000243 solution Substances 0.000 claims description 31
- 238000001179 sorption measurement Methods 0.000 claims description 24
- 238000010828 elution Methods 0.000 claims description 19
- 239000007853 buffer solution Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- JVIPLYCGEZUBIO-UHFFFAOYSA-N 2-(4-fluorophenyl)-1,3-dioxoisoindole-5-carboxylic acid Chemical compound O=C1C2=CC(C(=O)O)=CC=C2C(=O)N1C1=CC=C(F)C=C1 JVIPLYCGEZUBIO-UHFFFAOYSA-N 0.000 claims description 7
- 229920001425 Diethylaminoethyl cellulose Polymers 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920006321 anionic cellulose Polymers 0.000 claims description 3
- 239000012461 cellulose resin Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 2
- 150000003842 bromide salts Chemical class 0.000 claims 2
- 150000003841 chloride salts Chemical class 0.000 claims 2
- 150000004675 formic acid derivatives Chemical class 0.000 claims 2
- 150000002823 nitrates Chemical class 0.000 claims 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 239000011347 resin Substances 0.000 description 29
- 229920005989 resin Polymers 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 230000014508 negative regulation of coagulation Effects 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002565 heparin fraction Substances 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 150000007523 nucleic acids Chemical class 0.000 description 3
- 102000039446 nucleic acids Human genes 0.000 description 3
- 108020004707 nucleic acids Proteins 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- -1 alkyl radicals Chemical class 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 235000019846 buffering salt Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012149 elution buffer Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 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
- C08B37/0078—Degradation products
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/727—Heparin; Heparan
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEO8745A DE1195010B (de) | 1962-05-12 | 1962-05-12 | Verfahren zur Reinigung von Heparin nach der Chromatographischen Methode |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEO8745A DE1195010B (de) | 1962-05-12 | 1962-05-12 | Verfahren zur Reinigung von Heparin nach der Chromatographischen Methode |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1195010B true DE1195010B (de) | 1965-06-16 |
| DE1195010C2 DE1195010C2 (enrdf_load_stackoverflow) | 1966-02-17 |
Family
ID=7351473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEO8745A Granted DE1195010B (de) | 1962-05-12 | 1962-05-12 | Verfahren zur Reinigung von Heparin nach der Chromatographischen Methode |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1195010B (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1253868B (de) | 1962-12-10 | 1967-11-09 | Riker Laboratories Inc | Verfahren zur Gewinnung von Heparin |
| FR2342991A1 (fr) * | 1976-03-05 | 1977-09-30 | Kabi Ab | Procede pour la purification de l'heparine |
| US4119774A (en) * | 1976-03-05 | 1978-10-10 | Ab Kabi | Heparin purification method |
| US4122250A (en) * | 1977-08-22 | 1978-10-24 | Gottfried Schmer | Separation of high-activity heparin by affinity chromatography |
| US4226599A (en) * | 1979-06-20 | 1980-10-07 | Warner-Lambert Company | Removal of heparin from heparin-containing blood plasma samples using a triethylaminoethyl cellulose tablet |
| US4935204A (en) * | 1984-06-16 | 1990-06-19 | B. Braun-Ssc Ag | Process and device for the specific adsorption of heparin |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4198314A (en) | 1978-08-04 | 1980-04-15 | Warner-Lambert Company | Removal of heparin from heparin-containing blood plasma samples using a triethylaminoethyl cellulose tablet |
-
1962
- 1962-05-12 DE DEO8745A patent/DE1195010B/de active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1253868B (de) | 1962-12-10 | 1967-11-09 | Riker Laboratories Inc | Verfahren zur Gewinnung von Heparin |
| FR2342991A1 (fr) * | 1976-03-05 | 1977-09-30 | Kabi Ab | Procede pour la purification de l'heparine |
| US4119774A (en) * | 1976-03-05 | 1978-10-10 | Ab Kabi | Heparin purification method |
| US4122250A (en) * | 1977-08-22 | 1978-10-24 | Gottfried Schmer | Separation of high-activity heparin by affinity chromatography |
| US4226599A (en) * | 1979-06-20 | 1980-10-07 | Warner-Lambert Company | Removal of heparin from heparin-containing blood plasma samples using a triethylaminoethyl cellulose tablet |
| US4935204A (en) * | 1984-06-16 | 1990-06-19 | B. Braun-Ssc Ag | Process and device for the specific adsorption of heparin |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1195010C2 (enrdf_load_stackoverflow) | 1966-02-17 |
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