CH310979A - Process for the production of a double salt from adrenaline and sparteine sulfate. - Google Patents
Process for the production of a double salt from adrenaline and sparteine sulfate.Info
- Publication number
- CH310979A CH310979A CH310979DA CH310979A CH 310979 A CH310979 A CH 310979A CH 310979D A CH310979D A CH 310979DA CH 310979 A CH310979 A CH 310979A
- Authority
- CH
- Switzerland
- Prior art keywords
- adrenaline
- sparteine
- solution
- sulfate
- mole
- Prior art date
Links
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 title claims 22
- 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 14
- 229960001945 sparteine Drugs 0.000 title claims 14
- 238000000034 method Methods 0.000 title claims 7
- 150000003839 salts Chemical class 0.000 title claims 7
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 239000000243 solution Substances 0.000 claims 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 229930008564 C01BA04 - Sparteine Natural products 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- SLRCCWJSBJZJBV-UHFFFAOYSA-N alpha-isosparteine Natural products C1N2CCCCC2C2CN3CCCCC3C1C2 SLRCCWJSBJZJBV-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- WNSDDGBLIALDPB-HTZKOJAYSA-N lupinidine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.C1N2CCCC[C@@H]2[C@H]2CN3CCCC[C@H]3[C@@H]1C2 WNSDDGBLIALDPB-HTZKOJAYSA-N 0.000 claims 1
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- -1 sparteine sulfate Chemical class 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines Doppelsalzes aus Adrenalin und Sparteinsulfat.
Es ist bekannt, dass man Losungen von Adrenalin dadurch herstellen kann, da¯ man diese Base mittels verd nnter MineralsÏuren oder auch organiseher Säuren auflost. So hat sich die Losung 1 : 1000 in verdünnter Salzsäure als sehr beständig in der Pharmazie eingerührt, und es ist. bekannt, die Bestän- digkeit dieser Lösung durch einen Säure überschuss zu erhohen. Aber anch dieser Säureüberschuss kann die Losung nicht vollstÏndig vor der Zersetzung durch Oxydation schützen und hat ausserdem den Nachteil, bei Injektionen reizend zu wirken, so da¯ die allgemeine Verwendlmbsmöglie-hkeit darunter leiden muss.
Es wurde nun gefunden, dass man Adrenalin auch mit Salzen von organischen Basen, wie Sparteinsulfat, an Stelle von Säuren in Losung bringen kann, wodurch die Ver wendungsmöglichkeit vergrössert wird. Auch zeigen diese Losungen grosse Haltbarkeit, obwohl sie annähernd neutral sind.
Gegenstand des Patentes ist nun ein Verfahren zur Herstellung des Doppelsalzes Adrenalin-Sparteinsulfat, das dadurch gekennzeichnet ist, dass man Adrenalin in wässriger L¯sung auf Sparteinsulfat einwirken lϯt. Man kann die beiden Ausgangsstoffe z. B. in molekularem VerhÏltnis anwenden.
Man kann aber auch mit einem Überschuss an Sparteinsulfat arbeiten.. Dabei setzt sich ein Mol Adrenalin mit einem Mol Sparteinsulfat zu einem Doppelsalz um, das an ein Mol Schwefelsäure gebunden ist. Das Reaktionsprodukt aus äquimolekularenMengendei beiden Stoffe reagiert nach Beendigung dei Umsetzung gegenüber Methylrot genau neutral. Wenn man einen Übersehuss an Sparteinsulfat verwendet, so wird die Haltbarkeit der Losung gegenüber Oxydation erhöht.
Beispiel 1 :
Ein Mol Sparteinsulfat = 422 g wird in 2 Litern Wasser gelost und in diese Losuna a. llmählieh 1 Mol Adrenalin = 183 g in pulverisierter Form unter Rühren eingetragen, Die Losung erfolgt sehr schnell ohne Wärme- zufuhr.
Beispiel 2:
In eine AnfschlÏmmung von 1 Mol Adren, alin in 1 Liter Wasser gibt man èstes oder in Losung befindliches Sparteinsulfat bis vollständige Losung erfolgt ist. Das tritt r, a, ch dem Verbrauch von 1 Mol Sparteinsulfat ein. Nach Belieben kann man diesei Lösung weitere Mengen Sparteinsulfat zugeben.
Beispiel 3 : l Mol Sparteinsulfat wird in fester Form mit 1 Mol Adrenalin vermengt und mit einer beliebigen Menge Wasser Zll einer klaren und haltbaren Losung des Doppelsalzes verarbeitet.
PATENTANSPRUCH :
Verfahren zur Herstellung eines in Wasser l¯slichen Doppelsalzes aus Adrenalin, dadurch gekennzeichnet, dass man Spartein-
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the production of a double salt from adrenaline and sparteine sulfate.
It is known that solutions of adrenaline can be produced by dissolving this base with dilute mineral acids or organic acids. The solution 1: 1000 in dilute hydrochloric acid has proven to be very stable in pharmacy, and it is. known to increase the stability of this solution with an excess of acid. But even this excess acid cannot completely protect the solution from decomposition by oxidation and it also has the disadvantage of being irritating in the case of injections, so that its general applicability must suffer.
It has now been found that adrenaline can also be brought into solution with salts of organic bases, such as sparteine sulfate, instead of acids, which increases the possibility of use. These solutions also show great durability, although they are almost neutral.
The subject of the patent is a process for the production of the double salt adrenaline-sparteine sulphate, which is characterized in that adrenaline is allowed to act on sparteine sulphate in an aqueous solution. You can use the two starting materials z. B. apply in a molecular ratio.
But you can also work with an excess of sparteine sulfate. One mole of adrenaline reacts with one mole of sparteine sulfate to form a double salt, which is bound to one mole of sulfuric acid. The reaction product of equimolecular amounts of the two substances reacts exactly neutrally to methyl red after the reaction has ended. If an excess of sparteine sulfate is used, the durability of the solution against oxidation is increased.
Example 1 :
One mole of sparteine sulfate = 422 g is dissolved in 2 liters of water and poured into this Losuna a. One mole of adrenaline = 183 g is gradually added in powdered form with stirring. The solution takes place very quickly without supplying heat.
Example 2:
In a slurry of 1 mole of adrenaline in 1 liter of water, sparteine sulfate or sparteine sulfate in solution is added until it is completely dissolved. This occurs r, a, ch the consumption of 1 mole of sparteine sulfate. If you like, you can add more sparteine sulfate to this solution.
Example 3: 1 mol of sparteine sulfate is mixed in solid form with 1 mol of adrenaline and processed with any amount of water ZII of a clear and durable solution of the double salt.
PATENT CLAIM:
Process for the production of a water-soluble double salt from adrenaline, characterized in that one spartine
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH310979T | 1952-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310979A true CH310979A (en) | 1955-11-15 |
Family
ID=4494380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310979D CH310979A (en) | 1952-08-28 | 1952-08-28 | Process for the production of a double salt from adrenaline and sparteine sulfate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310979A (en) |
-
1952
- 1952-08-28 CH CH310979D patent/CH310979A/en unknown
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