SE202131C1 - - Google Patents
Info
- Publication number
- SE202131C1 SE202131C1 SE202131DA SE202131C1 SE 202131 C1 SE202131 C1 SE 202131C1 SE 202131D A SE202131D A SE 202131DA SE 202131 C1 SE202131 C1 SE 202131C1
- Authority
- SE
- Sweden
- Prior art keywords
- benzyl
- heparin
- salt
- heparinate
- alkali metal
- Prior art date
Links
- 229920000669 heparin Polymers 0.000 claims description 49
- -1 benzyl halide Chemical class 0.000 claims description 43
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical class 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 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
- 229960002897 heparin Drugs 0.000 claims description 22
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 3
- 239000002628 heparin derivative Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- UIOHNCCXQHLQJE-UHFFFAOYSA-N 2-carboxyprop-2-enylazanium bromide Chemical compound [Br-].C=C(C[NH3+])C(=O)O UIOHNCCXQHLQJE-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 claims 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- YFYABWXIJBTAAM-UHFFFAOYSA-M trimethyl(2-phenyltetradecan-2-yl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC(C)([N+](C)(C)C)C1=CC=CC=C1 YFYABWXIJBTAAM-UHFFFAOYSA-M 0.000 claims 1
- 230000002429 anti-coagulating effect Effects 0.000 description 5
- 230000015271 coagulation Effects 0.000 description 5
- 238000005345 coagulation Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000002402 anti-lipaemic effect Effects 0.000 description 4
- 239000003146 anticoagulant agent Substances 0.000 description 4
- 229940127219 anticoagulant drug Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108090000190 Thrombin Proteins 0.000 description 2
- 208000019622 heart disease Diseases 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 208000001297 phlebitis Diseases 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229960004072 thrombin Drugs 0.000 description 2
- 200000000007 Arterial disease Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000009123 Fibrin Human genes 0.000 description 1
- 108010073385 Fibrin Proteins 0.000 description 1
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108010094028 Prothrombin Proteins 0.000 description 1
- 102100027378 Prothrombin Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000004019 antithrombin Substances 0.000 description 1
- 206010003230 arteritis Diseases 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 229950003499 fibrin Drugs 0.000 description 1
- 229940012952 fibrinogen Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE202131T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE202131C1 true SE202131C1 (da) | 1965-01-01 |
Family
ID=38413309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE202131D SE202131C1 (da) |
Country Status (1)
| Country | Link |
|---|---|
| SE (1) | SE202131C1 (da) |
-
0
- SE SE202131D patent/SE202131C1/sv unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10730960B2 (en) | Dextran sulfate | |
| AU2016323377B2 (en) | Carbohydrate ligands that bind to antibodies against glycoepitopes of glycosphingolipids | |
| SE202131C1 (da) | ||
| US11306158B1 (en) | Method for preparing high-purity sugammadex sodium | |
| US3210250A (en) | Heparine derivatives and method of making same | |
| JP4585072B2 (ja) | ヘパリン解重合法、解重合ヘパリン、その誘導体および医薬組成物 | |
| CN116621856A (zh) | 一种新颖的氨基甲酸酯类化合物及其用途 | |
| CA1055530A (en) | Method of fat-resorption determination, as well as substances employed for this and preparations derived therefrom | |
| US10227370B2 (en) | Heparan sulfate/heparin mimetics with anti-chemokine and anti-inflammatory activity | |
| Schweiger | Methanolysis of fucoidan. II. The presence of sugars other than L-fucose | |
| CN115093492B (zh) | 一种偕胺肟壳寡糖配体及其制备方法和应用 | |
| SE204006C1 (da) | ||
| CN116621857A (zh) | 一种新颖的氨基甲酸酯类化合物及其用途 | |
| RU2502739C1 (ru) | N-КАРБ(ГЛУТАМИНИЛ)ОКСИМЕТИЛИМИДАЗО[4,5-е]БЕНЗО[1,2-с;3,4-с']ДИФУРОКСАН, ИНГИБИРУЮЩИЙ АГРЕГАЦИЮ ТРОМБОЦИТОВ | |
| US2561384A (en) | Decamethylenediamine salt of heparin | |
| US20200254003A1 (en) | Oligosaccharide compound for inhibiting intrinsic coagulation factor x-enzyme complex, and preparation method therefor and uses thereof | |
| FI59336B (fi) | Foerfarande foer framstaellning av en oevermaettad isosorbiddinitratloesning | |
| US3211617A (en) | Heparine derivatives and process for preparation and utilization | |
| AU2021329765A1 (en) | Stable pharmaceutical composition | |
| RU2838319C1 (ru) | Стабильная фармацевтическая субстанция холина янтарнокислого | |
| CN105601589A (zh) | 一种双苯氟嗪-对羟基苯甲酸共晶及其制备方法 | |
| CN103570596B (zh) | 一种硫普罗宁晶体化合物及其制备方法 | |
| RU2652993C1 (ru) | Новое 2-стирилпроизводное 4-(2,6-диметил-4-оксо-5-фенил-4н-пиримидин-1-ил)-бензсульфамида, обладающее эндотелеопротекторной активностью | |
| DE2350392C2 (de) | Aromatische Cardenolid-Acetale, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| US3207665A (en) | Heparin derivatives and methods of making same |