CH210715A - Process for the preparation of a corticosterone ester. - Google Patents
Process for the preparation of a corticosterone ester.Info
- Publication number
- CH210715A CH210715A CH210715DA CH210715A CH 210715 A CH210715 A CH 210715A CH 210715D A CH210715D A CH 210715DA CH 210715 A CH210715 A CH 210715A
- Authority
- CH
- Switzerland
- Prior art keywords
- corticosterone
- oleylating
- ester
- oleylation
- agent
- 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 Herstellung eines Corticosteronesters. Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung eines Corticosteronesters, das dadurch gekennzeich net ist, dass man Corticosteron mit oleylie- renden Mitteln behandelt.
Die auf diese Weise gewonnene Verbin dung besitzt die Formel CziHza04 # CO . C171133 und die folgende Struktur:
EMI0001.0010
Sie bildet eine gallertige Masse von fett artiger Beschaffenheit und schmilzt bei etwa 80 C. Sie lässt sich aus Petroläther um kristallisieren.
Zur Oleylierung eignen sich die bekann ten Veresterungsmethoden.. Nur solche Me- thoden, bei denen stark alkalische Reagen- tien (wie freie Alkalien) benötigt werden, sind entweder mit grosser Vorsicht zu be nutzen oder ganz auszuschliessen.
-Methoden, bei denen freie Mineralsäure (wie Chlorwas serstoff) auftritt, können bei vorsichtigem Arbeiten benutzt werden, zweckmässig ist es jedoch in diesen Fällen unter Zusatz von säurebindenden Mitteln (wie Pyridin, ga- liumkarbonat, etc.) zu arbeiten. Auch durch Umesterung kann das Corticosteronoleat ge wonnen werden. Gegebenenfalls arbeitet man in Gegenwart von Verdünnungsmitteln, vie Äther, Benzol, Aceton usw.
Der neue Ester des Corticosterons soll therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung oder zur Reinigung von therapeutisch wertvollen Ver bindungen dienen.
<I>Beispiel:</I> 20 mg Corticosteron werden in 80 mg Pyridin gelöst, mit der Lösung von 25 mg Ölsäurechlorid in 0,5 ein' trockenem Äther versetzt und ohne Beachtung der Ausschei- dung von Kristallen bei gelinder Wärme zur Trockne gedämpft. Der Rückstand wird mit etwas Wasser versetzt und mit Äther in einen Scheidetrichter gespült. Er wird meh rere Male mit verdünnter Salzsäure, dann mit Wasser gewaschen. Die getrocknete Ätherlösung wird durch Destillation von Äther befreit und der Rückstand mit Pentan angerieben.
Der bald gallertig ausfallende Ölsäureester des Corticosterons wird abge- nutscht und mehrmals mit Pentan gewaschen. Er lässt sich aus Petroläther durch Einengen umkristallisieren. Er behält dabei eine etwa fettartige Konsistenz und schmilzt bei etwa 80 C. Der Ester ist leicht fettlöslich und unlöslich in Wasser.
Process for the preparation of a corticosterone ester. The subject of the present patent is a process for the production of a corticosterone ester which is characterized in that corticosterone is treated with olefinic agents.
The compound obtained in this way has the formula CziHza04 # CO. C171133 and the following structure:
EMI0001.0010
It forms a gelatinous mass with a fatty texture and melts at around 80 C. It can be crystallized from petroleum ether.
The known esterification methods are suitable for oleylation. Only those methods which require strongly alkaline reagents (such as free alkalis) are either to be used with great caution or to be excluded entirely.
-Methods in which free mineral acid (such as hydrogen chloride) occurs can be used with caution, but in these cases it is advisable to work with the addition of acid-binding agents (such as pyridine, gallium carbonate, etc.). The corticosterone oleate can also be obtained by transesterification. If necessary, one works in the presence of diluents, like ether, benzene, acetone, etc.
The new ester of corticosterone should be used therapeutically or serve as an intermediate for the production or purification of therapeutically valuable compounds.
<I> Example: </I> 20 mg of corticosterone are dissolved in 80 mg of pyridine, the solution of 25 mg of oleic acid chloride in 0.5% of a dry ether is added and, regardless of the precipitation of crystals, steamed to dryness with gentle heat . The residue is mixed with a little water and rinsed with ether into a separating funnel. It is washed several times with dilute hydrochloric acid and then with water. The dried ethereal solution is freed from ether by distillation and the residue is rubbed with pentane.
The oleic acid ester of corticosterone, which soon becomes gelatinous, is filtered off with suction and washed several times with pentane. It can be recrystallized from petroleum ether by concentration. It retains an approximately fat-like consistency and melts at around 80 C. The ester is easily soluble in fat and insoluble in water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH204233T | 1936-12-23 | ||
| CH210715T | 1936-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210715A true CH210715A (en) | 1940-07-31 |
Family
ID=25724009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210715D CH210715A (en) | 1936-12-23 | 1936-12-23 | Process for the preparation of a corticosterone ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210715A (en) |
-
1936
- 1936-12-23 CH CH210715D patent/CH210715A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH210715A (en) | Process for the preparation of a corticosterone ester. | |
| CH210714A (en) | Process for the preparation of a corticosterone ester. | |
| DE959189C (en) | Process for the preparation of 17ª ‰ -acyloxy-20-keto-allopregnans and -pregnenes | |
| DE873699C (en) | Process for the preparation of oxygen-rich derivatives of unsaturated compounds of the androstane and pregnane series | |
| AT219206B (en) | Process for the preparation of new, strongly progestationally active derivatives of δ <1> -allopregnen-17α-ol-3,20-dione | |
| AT159505B (en) | Process for the preparation of new esters. | |
| CH210712A (en) | Process for the preparation of a corticosterone ester. | |
| DE929424C (en) | Process for the production of sterols or their addition compounds from mixtures or solutions containing sterols | |
| AT250584B (en) | Process for the preparation of new steroid ol acylates | |
| AT202712B (en) | Process for the extraction of alkaloids | |
| AT147306B (en) | Process for the purification of raw extracts of the gonad hormones. | |
| CH210711A (en) | Process for the preparation of a corticosterone ester. | |
| CH210713A (en) | Process for the preparation of a corticosterone ester. | |
| AT233746B (en) | Process for the production of reserve acid diesters and their salts | |
| DE848824C (en) | Process for the preparation of derivatives of saturated or unsaturated compounds of the ª †, ª € -di (p-oxyphenyl) -hexane series | |
| CH204233A (en) | Process for the preparation of a corticosterone ester. | |
| AT159896B (en) | Process for the preparation of 17-acyl- or 17-glycosidoderivatives of estradiol. | |
| DE957030C (en) | Process for the preparation of the phenylpropionic acid esters of steroid hormones | |
| AT142027B (en) | Process for the preparation of acyl derivatives of the dihydrofollicle hormone. | |
| CH210719A (en) | Method for representing a connection of the adrenal cortex hormone series. | |
| CH210718A (en) | Method for representing a connection of the adrenal cortex hormone series. | |
| CH210720A (en) | Method for representing a connection of the adrenal cortex hormone series. | |
| CH210716A (en) | Process for the preparation of a corticosterone ester. | |
| CH226686A (en) | Process for the manufacture of pregnenolone. | |
| CH225108A (en) | Process for the preparation of a new ester. |