CH210721A - Method for representing a connection of the adrenal cortex hormone series. - Google Patents
Method for representing a connection of the adrenal cortex hormone series.Info
- Publication number
- CH210721A CH210721A CH210721DA CH210721A CH 210721 A CH210721 A CH 210721A CH 210721D A CH210721D A CH 210721DA CH 210721 A CH210721 A CH 210721A
- Authority
- CH
- Switzerland
- Prior art keywords
- stearylating
- stearylation
- agent
- carried out
- adrenal cortex
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung einer Verbindung der Nebennierenrindenhormonreihe. Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung einer Verbindung der Nebennierenrindenhormon- reihe, das dadurch gekennzeichnet ist, dass man Desogycorticosteron mit einem steary- lierenden Mittel behandelt.
Die auf diese Weise gewonnene Verbin dung hat die Formel CS1H290g-C0 # C171135 und besitzt die Struktur:
EMI0001.0012
kannten Veresterungsmethoden. Nur solche Methoden, bei denen stark alkalische Rea- gentien (wie freie Alkalien) benötigt wer den, sind entweder mit grosser Vorsicht zu benutzen oder ganz auszuschliessen. Bei Ver wendung von Methoden, bei denen freie Mi neralsäure (z.
B. Chlorwasserstoffsäure) auf tritt, arbeitet man zweckmässig mit säure bindenden Mitteln (tertiäre Basen, Kalium- carbonat etc.). Auch durch Umesterung kann das Desogycorticosteronstearat dargestellt werden. Gegebenenfalls arbeitet man in Ge genwart von Verdünnungsmitteln, wie Äther, Benzol, Aceton usw.
Die neue Verbindung soll therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung von therapeutischen wert vollen Verbindungen dienen.
<I>Beispiel:</I> Zu einer mit Kältemischung gekühlten Lösung von 0,5 Teilen Desogycorticosteron und 5 Teilen Pyridin wird 1 Teil Stearin- Diese Verbindung bildet farblose Kri stalle, die bei 63 bis 64' schmelzen; sie lässt sich aus Petroläther umkristallisieren.
Zur Stearylierung eignen sich die be- säurechlorid zugetropft und das Gemisch während mehreren Stunden bei Raumtem peratur stehen gelassen. Nach Versetzen mit. Wasser wird das Reaktionsprodukt in Äther aufgenommen.
plan schüttelt die Ätherlösung nacheinander mit verdünnter Salzsäure ver dünnter Sodalösung, verdünnter Natronlauge und Nasser und trocknet sie über Na.trium- sttlfat. Das durch Verdampfen des Lösungs mittels gewonnene Stearat des Desoxycortico- sterons wird aus Petroläther umkristallisiert und zeigt hierauf einen F. von 63 bis 64 und eine spezifische Drehung von [a1 -!-- 116 (in Chloroform).
Method for representing a connection of the adrenal cortex hormone series. The subject of the present patent is a process for the preparation of a compound of the adrenal cortical hormone series, which is characterized in that desogycorticosterone is treated with a stearylating agent.
The compound obtained in this way has the formula CS1H290g-C0 # C171135 and has the structure:
EMI0001.0012
knew esterification methods. Only those methods that require strongly alkaline reagents (such as free alkalis) are either to be used with great caution or to be excluded entirely. When using methods in which free mineral acid (e.g.
B. hydrochloric acid) occurs, it is advisable to work with acid-binding agents (tertiary bases, potassium carbonate, etc.). Desogycorticosterone stearate can also be produced by transesterification. If necessary, one works in the presence of diluents such as ether, benzene, acetone, etc.
The new compound should find therapeutic use or serve as an intermediate for the preparation of therapeutically valuable compounds.
<I> Example: </I> To a solution of 0.5 part desogycorticosterone and 5 parts pyridine, cooled with a cold mixture, 1 part stearin is added. This compound forms colorless crystals which melt at 63 to 64 '; it can be recrystallized from petroleum ether.
For the stearylation, the acid chloride is added dropwise and the mixture is left to stand for several hours at room temperature. After moving with. Water, the reaction product is taken up in ether.
Plan shakes the ethereal solution one after the other with dilute hydrochloric acid, dilute soda solution, dilute caustic soda and water, and dries it over sodium trium chloride. The deoxycorticosterone stearate obtained by evaporation of the solution is recrystallized from petroleum ether and shows an F. from 63 to 64 and a specific rotation of [a1 -! - 116 (in chloroform).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH204234T | 1936-12-23 | ||
| CH210721T | 1936-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210721A true CH210721A (en) | 1940-07-31 |
Family
ID=25724015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210721D CH210721A (en) | 1936-12-23 | 1936-12-23 | Method for representing a connection of the adrenal cortex hormone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210721A (en) |
-
1936
- 1936-12-23 CH CH210721D patent/CH210721A/en unknown
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