DE944189C - Process for the production of anti-coagulant substances - Google Patents
Process for the production of anti-coagulant substancesInfo
- Publication number
- DE944189C DE944189C DEK17944A DEK0017944A DE944189C DE 944189 C DE944189 C DE 944189C DE K17944 A DEK17944 A DE K17944A DE K0017944 A DEK0017944 A DE K0017944A DE 944189 C DE944189 C DE 944189C
- Authority
- DE
- Germany
- Prior art keywords
- production
- substances
- sulfuric acid
- inulin
- coagulant
- 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
- 239000000126 substance Substances 0.000 title claims description 7
- 239000003146 anticoagulant agent Substances 0.000 title claims description 4
- 229940127219 anticoagulant drug Drugs 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 229920001202 Inulin Polymers 0.000 claims description 6
- 229940029339 inulin Drugs 0.000 claims description 6
- -1 inulin sulfuric acid ester Chemical class 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 235000014633 carbohydrates Nutrition 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 description 6
- 239000005017 polysaccharide Substances 0.000 description 6
- 150000004676 glycans Chemical class 0.000 description 4
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229920000669 heparin Polymers 0.000 description 2
- 229960002897 heparin Drugs 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 229920000297 Rayon Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0051—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Fructofuranans, e.g. beta-2,6-D-fructofuranan, i.e. levan; Derivatives thereof
- C08B37/0054—Inulin, i.e. beta-2,1-D-fructofuranan; Derivatives 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)
Description
Verfahren zur Herstellung von blutgerinnunghemmenden Stoffen Es wurde schon mehrfach vorgeschlagen, Schwefelsäureester von Polysacchariden als blutgerinnnnghemmende Stoffe zu verwenden. Bei vielen solchen Stoffen hat sich gezeigt, daß diese Ester zwar stark wirksam, aber zugleich so toxisch sind, daß sie therapeutisch nicht verwendbar sind (Ingelman, Arkiv för Kein, Mineralogi och Geologie, Bd. 24B, Nr. 5 [1947], S. I bis 4).Process for the manufacture of anti-coagulant substances It was It has already been proposed several times to use sulfuric acid esters of polysaccharides as anticoagulants Substances to use. With many such substances it has been shown that these esters highly effective, but at the same time so toxic that they cannot be used therapeutically are (Ingelman, Arkiv för Kein, Mineralogi och Geologie, Vol. 24B, No. 5 [1947], Pp. I to 4).
Es wurde nun gefunden, daß man Inulinschwefelsäureester durch nachträgliche Behandlung mit solchen oxydierenden Mitteln, die Kohlenhydrate in die entsprechenden Uronsäuren überzuführen vermögen, derart abwandeln kann, daß ein Teil der primären Alkoholgruppen in Carboxylgruppen übergeführt wird) und man erhält auf diese Weise gut verträgliche Präparate von gleich starker blutgerinnunghemmender Wirkung. Die neuen Stoffe stehen in naher Verwandschaft zum Heparin, das als Polymucoildinschwe£elsäurèester ebenfalls sowohl Carboxyl- als auch Schwefelsäurereste enthält. It has now been found that inulin sulfuric acid esters by subsequent Treatment with such oxidizing agents, the carbohydrates in the appropriate Ability to transfer uronic acids, can modify them in such a way that some of the primary Alcohol groups is converted into carboxyl groups) and is obtained in this way well tolerated preparations with equally strong anti-coagulant effects. the New substances are closely related to heparin, the polymucoildin sulfuric acid ester also contains both carboxyl and sulfuric acid residues.
Als Oxydationsmittel für die Umwandlung der Polysaccharidschwefelsäureester hauben sich vorzugsweise Salpetersäure und Natrinmuitrit bzw. As an oxidizing agent for the conversion of the polysaccharide sulfuric acid ester Preferably nitric acid and sodium muitrite resp.
Stickoxyde bewährt.Proven nitrogen oxides.
Es ist zwar bekannt, Polysaccharide durch Einwirkung von Oxydationsmitteln in Polyuronsäuren umzuwandeln; diese Oxydation ist jedoch bei Polysaccharidschwefels äurees tern bis jetzt nicht versucht worden, und das Gelingen dieser Reaktion war auch nicht vorauszusehen. Although it is known to polysaccharides by the action of oxidizing agents convert to polyuronic acids; however, this oxidation is at Polysaccharide sulfur acid esters have not yet been attempted, and this reaction was successful also not to be foreseen.
Es wurde auch schon vorgeschlagen, Cellulose (Zellwolle) zunächst zu carboxylieren und darauf zu sulfurieren, wodurch ebenfalls carboxylierte Polysaccharidschwefelsäureester erhalten werden. It has also been suggested to use cellulose (rayon) initially to carboxylate and then to sulfurize, whereby also carboxylated polysaccharide sulfuric acid esters can be obtained.
Diese Produkte haben wegen ihrer schwachen Heparinwirkung keinen Eingang in den Arzneischatz gefunden. Auf Inulin war dieses bekannte Verfahren nicht anwendbar, da dieses Polysaccharid bei der Einwirkung von Oxydationsmitteln vollkommen zersetzt wird.These products have no entrance because of their weak heparin action found in the medicine treasure. This known method was not applicable to inulin, since this polysaccharide completely decomposes when exposed to oxidizing agents will.
Beispiel I00 g gut gereinigtes Natriumsalz des Inulinsulfats, das aus reinstem Inulin (für Clearance-Untersuchungen) gewomeen !worden ist, werden in 1 1 25°/aiger Salpetersäure gelöst. In diese Lösung werden bei 20° im Laufe von 5 Stunden 20 g Natriumnitrit unter stetigem Rühren in kleinen Portionen eingefragen. Die Reaktionslösung wird weitere 2 Stunden bei 200 stehengelassen. Darauf wird das oxydierte Inulinsulfat mit etwa 3 1 Alkohol gefällt, wiederholt mit Eisessig, Aceton, Ather gewaschen und getrocknet. Ausbeute: etwa 60 g. Example 100 g of well purified sodium salt of inulin sulfate, which made from the purest inulin (for clearance studies) dissolved in 1 liter of 25% nitric acid. In this solution at 20 ° during For 5 hours, fill in 20 g of sodium nitrite in small portions while stirring constantly. The reaction solution is left to stand at 200 for a further 2 hours. Then that will oxidized inulin sulfate precipitated with about 3 liters of alcohol, repeated with glacial acetic acid, acetone, Ather washed and dried. Yield: about 60 g.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK17944A DE944189C (en) | 1953-05-03 | 1953-05-03 | Process for the production of anti-coagulant substances |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK17944A DE944189C (en) | 1953-05-03 | 1953-05-03 | Process for the production of anti-coagulant substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE944189C true DE944189C (en) | 1956-06-07 |
Family
ID=7215251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK17944A Expired DE944189C (en) | 1953-05-03 | 1953-05-03 | Process for the production of anti-coagulant substances |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE944189C (en) |
-
1953
- 1953-05-03 DE DEK17944A patent/DE944189C/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
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