CH310980A - Process for the preparation of a water-soluble complex salt from glycerol phosphoric acid calcium and sparteine sulfate. - Google Patents
Process for the preparation of a water-soluble complex salt from glycerol phosphoric acid calcium and sparteine sulfate.Info
- Publication number
- CH310980A CH310980A CH310980DA CH310980A CH 310980 A CH310980 A CH 310980A CH 310980D A CH310980D A CH 310980DA CH 310980 A CH310980 A CH 310980A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- sparteine
- complex salt
- acid calcium
- sulfate
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 18
- SLRCCWJSBJZJBV-AJNGGQMLSA-N sparteine Chemical compound C1N2CCCC[C@H]2[C@@H]2CN3CCCC[C@H]3[C@H]1C2 SLRCCWJSBJZJBV-AJNGGQMLSA-N 0.000 title claims description 15
- 229960001945 sparteine Drugs 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 7
- AGEDSIKTYLSETF-UHFFFAOYSA-N calcium;phosphoric acid;propane-1,2,3-triol Chemical compound [Ca].OP(O)(O)=O.OCC(O)CO AGEDSIKTYLSETF-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- XYZZKVRWGOWVGO-UHFFFAOYSA-N Glycerol-phosphate Chemical compound OP(O)(O)=O.OCC(O)CO XYZZKVRWGOWVGO-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229930008564 C01BA04 - Sparteine Natural products 0.000 claims description 2
- SLRCCWJSBJZJBV-UHFFFAOYSA-N alpha-isosparteine Natural products C1N2CCCCC2C2CN3CCCCC3C1C2 SLRCCWJSBJZJBV-UHFFFAOYSA-N 0.000 claims description 2
- 230000029142 excretion Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 150000007513 acids Chemical class 0.000 description 3
- IWIRHXNCFWGFJE-UHFFFAOYSA-L calcium;2,3-dihydroxypropyl phosphate Chemical compound [Ca+2].OCC(O)COP([O-])([O-])=O IWIRHXNCFWGFJE-UHFFFAOYSA-L 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- KORBDTTXVKJAGP-UHFFFAOYSA-H tricalcium propane-1,2,3-triol diphosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OCC(O)CO KORBDTTXVKJAGP-UHFFFAOYSA-H 0.000 description 3
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 101000952234 Homo sapiens Sphingolipid delta(4)-desaturase DES1 Proteins 0.000 description 1
- 102100037416 Sphingolipid delta(4)-desaturase DES1 Human genes 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008320 venous blood flow Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines wasserlöslichen Komplexsalzes aus glycerinphosphorsaurem Calcium und Sparteinsulfat. Das glycerinphosphorsaure Calcium des 1). A. B. 6 von der Formel CH20H # CHOH # CH2 (OP03Ca) # 2H20 stellt ein sehr schwer lösliches Salz dar, das sich nur langsam in 40 Teilen Wasser von 15 C auflöst.
Wie bisher aus der Literatur bekannt. ist, lässt sich das Caleiumgly eerin- phosphat nur mit Säuren in leichter lösliche S'alze überführen, die aber bei Verwendung von starken Säuren die Gefahr in sich ber gen, sich zu zersetzen, da die freie Glycerin phosphorsäure in wässriger Lösung unbestän dig ist. Es gelang zwar, durch Zusatz von Citronensäure die Löslichkeit heraufzusetzen (Pharm. Zentralblatt 4, 1928), jedoch enthal ten alle diese Verbindungen freie Säuren.
Nicht bekannt war jedoch bisher"dass es <B>t</B> -)ueh gelingt, durch Salzumsetzung die Lös lichkeit des Calciumglycerinphosphates zu erhöhen. Es wurde gefunden, dass dies durch Bildung von Komplexsalzen mit S.parteinsul- fat gelingt:. Das gegen Lackmus schwach alka lisch reagierende Caleiumglycerinphosphat tritt mit dem gegen Lackmus sauer reagie renden Sparteinsulfat in wässriger Lösung in Reaktion, ohne dass überraschenderweise Gips hydrat gebildet wird.
Die in den verschieden sten l-Iengenverhältnissen herzustellenden Lö sungen sind beständig und scheiden auch nach langem Stehen kein Gipshydrat aus. Die Löslichkeit dieser Komplexverbindungen ist ungefähr doppelt so hoch, wie die des ge wöhnliehen Caleiumglycerinphosphates.
Gegenstand des Patentes ist nun ein Ver fahren zur Herstellung einer Komplexverbin dung aus glycerinphosphorsaurem Calcium und Sparteinsulfat, das dadurch gekennzeich net ist, dass man ungefähr äquimolekulare Mengen von glycerinphosphorsaurem Cal cium und Sparteinsulfat in Gegenwart von Wasser aufeinander einwirken lässt.
Das so erhaltene Salz stellt eine weisse Substanz von bitterem Geschmack dar, welche in wä,ssriger Lösung mit Natronlauge versetzt eine ölige Ausscheidung von Sparteinbase, mit Ammoniumoxalat eine Fällung von Cal- eiumoxalat ergibt. Einen Schmelzpunkt be sitzt dieses Salz nicht. In Wasser ist dieses Salz 1:10 löslich.
Dieses Komplexsalz ist infolge seiner fast neutralen Reaktion injektionsfähig und als Injektionslösung sowie als Salbe äusserlich und auch als Dragee bzw. Tablette innerlich angewendet, von guter Wirkung bei gestörter venöser Durchblutung infolge Stauungen va rikÖser Art. Die Lösung des Komplexsalzes besitzt in einer Verdünnung von 1:10 in Wasser den pH-Wert von 5,7.
Die Herstellung des Salzes kann z. B. durch Vorlegung einer Sparteinsulfatlösung und nachträgliches Eintragen von glycerin- phosphorsaurem Caleium oder durch Ver setzen einer Suspension von glycerinphosphor- saurem Calcium in Wasser mit festem oder gelöstem Sparteinsulfat erfolgen. Auch kön nen die Salze durch Lösung in Wasser oder feuchtes Ankneten in das Komplexsalz über- führt werden.
Beispiel <I>1:</I> 600 g Sparteinsulfat werden in 6 Litern Wasser gelöst und nacheinander in Portionen 300 g Calciumglyeerinphosphat eingetragen, bis Lösung erfolgt ist. <I>Beispiel</I> 7u einer Aufschlämmung von 300 g Cal- ciumgly cerinphosphat in Wasser werden 600 g Sparteinsulfat in fester oder gelöster Form unter Schütteln gebracht, bis vollständige Lö sung erfolgt ist.
<I>Beispiel 3:</I> Die in Beispiel 1. und 2 gewählten Mengen trockengemischter Salze werden in Wasser gegeben und zusammen zur Reaktion ge bracht oder mit wenig Wasser angefeuchtet und. durch Kneten umgesetzt und bei nied riger Temperatur getrocknet.
Process for the preparation of a water-soluble complex salt from glycerol phosphoric acid calcium and sparteine sulfate. The glycerolphosphoric acid calcium des 1). A. B. 6 of the formula CH20H # CHOH # CH2 (OP03Ca) # 2H20 is a very sparingly soluble salt that dissolves only slowly in 40 parts of water at 15 ° C.
As previously known from the literature. the calcium glycerin phosphate can only be converted into more soluble salts with acids, which, however, involve the risk of decomposition when using strong acids, since the free glycerol phosphoric acid is unstable in aqueous solution. Although it was possible to increase the solubility by adding citric acid (Pharm. Zentralblatt 4, 1928), all these compounds contain free acids.
Up to now, however, it was not known "that it is possible to increase the solubility of calcium glycerol phosphate by converting salts. It has been found that this is achieved by forming complex salts with S.parteinsulphate :. The calcium glycerol phosphate, which reacts weakly alkaline against litmus, reacts in aqueous solution with sparteine sulfate, which reacts acidic against litmus, without, surprisingly, gypsum hydrate being formed.
The solutions to be produced in the most varied of length ratios are stable and do not excrete any gypsum hydrate even after long periods of standing. The solubility of these complex compounds is about twice as high as that of the usual calcium glycerol phosphate.
The subject of the patent is now a process for the production of a complex compound of glycerophosphate calcium and sparteine sulfate, which is characterized in that approximately equimolecular amounts of glycerophosphate calcium and sparteine sulfate can act on each other in the presence of water.
The salt thus obtained is a white substance with a bitter taste, which in aqueous solution mixed with sodium hydroxide solution results in an oily excretion of sparteine base, with ammonium oxalate a precipitation of calcium oxalate. This salt does not have a melting point. This salt is 1:10 soluble in water.
Due to its almost neutral reaction, this complex salt can be injected and used externally as an injection solution as well as an ointment and internally as a dragee or tablet, of good effect in case of disturbed venous blood flow due to congestion of various kinds. The solution of the complex salt has a dilution of 1: 10 has a pH of 5.7 in water.
The preparation of the salt can e.g. B. by submitting a sparteine sulfate solution and subsequent entry of glycerol phosphoric acid Caleium or by setting a suspension of glycerol phosphoric acid calcium in water with solid or dissolved sparteine sulfate. The salts can also be converted into the complex salt by dissolving them in water or by wet kneading.
Example <I> 1: </I> 600 g of sparteine sulfate are dissolved in 6 liters of water and 300 g of calcium glycerine phosphate are added one after the other in portions until the solution is dissolved. <I> Example </I> 7u of a slurry of 300 g calcium glycerine phosphate in water, 600 g sparteine sulfate in solid or dissolved form are brought with shaking until complete dissolution has taken place.
<I> Example 3: </I> The amounts of dry mixed salts selected in Example 1 and 2 are added to water and brought together to react or moistened with a little water and. implemented by kneading and dried at low temperature.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH310980T | 1952-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310980A true CH310980A (en) | 1955-11-15 |
Family
ID=4494381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310980D CH310980A (en) | 1952-08-28 | 1952-08-28 | Process for the preparation of a water-soluble complex salt from glycerol phosphoric acid calcium and sparteine sulfate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310980A (en) |
-
1952
- 1952-08-28 CH CH310980D patent/CH310980A/en unknown
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