DE1643174B2 - PROCESS FOR THE PRODUCTION OF 16-ACYL-GITOXIN - Google Patents
PROCESS FOR THE PRODUCTION OF 16-ACYL-GITOXINInfo
- Publication number
- DE1643174B2 DE1643174B2 DE19671643174 DE1643174A DE1643174B2 DE 1643174 B2 DE1643174 B2 DE 1643174B2 DE 19671643174 DE19671643174 DE 19671643174 DE 1643174 A DE1643174 A DE 1643174A DE 1643174 B2 DE1643174 B2 DE 1643174B2
- Authority
- DE
- Germany
- Prior art keywords
- gitoxin
- acetyl
- acetylgitoxin
- formylgitoxin
- cat
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
Description
kosid wird in Chloroform aufgenommen, die wäßrige Lösung anschließend mit Chloroform ausgeschüttelt. Die vereinigten Chloroformlösungen werden über Natriumsulfat getrocknet und im Vakuum zur Trockne eingeengt. Die angefallene Schmelze enthält Gitoxin (im Durchschnitt 60%) und 16-Acetyl-gitoxin (im Durchschnitt 40%). Ausbeute: 13,3 g. Das teilweise entacetylierte Substanzgemisch (a) wird nun durch multiplikative Verteilung nach O'Keef f e (vgl. E. Meeker, Verteilungsverfahren im Laboratorium, Verlag Chemie, 1955, Weinheim, Bergstraße) in 5 Elementen getrennt.Koside is taken up in chloroform, the aqueous one Solution then extracted with chloroform. The combined chloroform solutions are over Dried sodium sulfate and concentrated to dryness in vacuo. The resulting melt contains Gitoxin (on average 60%) and 16-acetyl-gitoxin (on average 40%). Yield: 13.3 g. That partially deacetylated substance mixture (a) is now determined by multiplicative distribution according to O'Keef f e (cf. E. Meeker, Distribution Process in the Laboratory, Verlag Chemie, 1955, Weinheim, Bergstrasse) separated into 5 elements.
Lösungsmittel: Methanol zu Wasser zu Chloroform zu Tetrachlorkohlenstoff = 3 :2:1,4 : 0,7; je Verteilungsschritt Solvent: methanol to water to chloroform to carbon tetrachloride = 3: 2: 1.4: 0.7; per distribution step
600 ml Oberphase,
50 ml Unterphase,
600 mg Substanz (a),600 ml upper phase,
50 ml lower phase,
600 mg substance (a),
zugegeben in die Mittelstellung.admittedly in the middle position.
Ausbeute aus der Unterphase: 4,0 g 16-Acetyl-gitoxin mit 85% Reinheit, aus der Oberphase 6,85 g Gitoxin mit geringen Spuren 16-Acetyl-gitoxin. Die restliche Substanz verbleibt in der Apparatur und wird bei späteren Verteilungsgängen wieder verarbeitet. Yield from the lower phase: 4.0 g of 16-acetylgitoxin with 85% purity, 6.85 g of gitoxin with small traces of 16-acetyl-gitoxin from the upper phase. the the remaining substance remains in the apparatus and is processed again in later distribution processes.
Claims (1)
mit Acylverbindungen des Gitoxins, die in den letz- Ziel und Aufgabe der Erfindung war daher, einGitoxin is a cardanolide glycoside from Digitalis-1144 [1960] and G. Baumgarten, Cach. Phararten, especially the Digitalis purpurea, which because of maz., 295, 305 [1962]). For a representation in Mcns of his bad physical properties, such as those required for therapy, cannot be used for technical reasons. Examinations 30 den, these procedures can not be used,
with acyl compounds of gitoxin, which in the final aim and object of the invention was therefore a
(Förster) mit zahlreichen Mono- und Polyacetyl-tion of a formyl group on the C16 atom of the genin 35 16-acetylgitoxin and gitoxin-containing mixture or a peracetylation of all free hydroalkyl groups through precise acetylation of the gitoxin and subsequent to pharmacologically and clinically effective gentle saponification, which leads to glycosides. Since formylgitoxin in its pure form has a limited shelf life, a method of distribution using the Menur, it is only mixed with other glycosides 40 in natural association with a suitable phase, e.g. B. carbon tetrachloride chloroiorm (digitoxin, gitoxin and verodoxin) and resorption methanol-water, in 16-acetylgitoxin and gitoxin require medical use (German interpretation can be separated. The inventive document 1 063 160). Driving 16-acylgitoxins with homologs is characterized in that one geder formic acid, z. B. acetic acid, or a mixture of di- and trio-acid, which is available as an example, have a 45% acetylgitoxin at room temperature with a considerably higher stability than 16-formylgitoxin with a 1.15-considerably higher stability, but they are difficult to produce a molar excess of dilute aqueous bar . They have a special sodium bicarbonate solution for the following reason: Pentaacetylgitoxin has become a gitoxin and the resulting mixture of long-acting glycoside has been shown to have an effect of oxin and 16-acetylgitoxin with a multiplicative digestion in the range of digoxin-digitoxin . Own 50 undergoes division. The recovered gitoxin from systematic animal studies can be used again.
(Förster) with numerous mono- and polyacetyl
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEV0032727 | 1967-01-07 |
Publications (3)
Publication Number | Publication Date |
---|---|
DE1643174A1 DE1643174A1 (en) | 1971-12-02 |
DE1643174B2 true DE1643174B2 (en) | 1973-03-01 |
DE1643174C3 DE1643174C3 (en) | 1973-09-27 |
Family
ID=7587529
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19671643174 Expired DE1643174C3 (en) | 1967-01-07 | 1967-01-07 | Process for the preparation of 16 acyl gitoxin |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE1643174C3 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2319873A1 (en) * | 1973-04-19 | 1974-10-31 | Boehringer Mannheim Gmbh | 16-O-ALKYL DERIVATIVES OF GITOXY INDIGITOXOSIDES AND THE PROCESS FOR THEIR PRODUCTION |
-
1967
- 1967-01-07 DE DE19671643174 patent/DE1643174C3/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2319873A1 (en) * | 1973-04-19 | 1974-10-31 | Boehringer Mannheim Gmbh | 16-O-ALKYL DERIVATIVES OF GITOXY INDIGITOXOSIDES AND THE PROCESS FOR THEIR PRODUCTION |
Also Published As
Publication number | Publication date |
---|---|
DE1643174C3 (en) | 1973-09-27 |
DE1643174A1 (en) | 1971-12-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C3 | Grant after two publication steps (3rd publication) | ||
E77 | Valid patent as to the heymanns-index 1977 |