CH176487A - Method for the preparation of an acyloctahydrofollicle hormone. - Google Patents
Method for the preparation of an acyloctahydrofollicle hormone.Info
- Publication number
- CH176487A CH176487A CH176487DA CH176487A CH 176487 A CH176487 A CH 176487A CH 176487D A CH176487D A CH 176487DA CH 176487 A CH176487 A CH 176487A
- Authority
- CH
- Switzerland
- Prior art keywords
- hormone
- preparation
- acyloctahydrofollicle
- hydrogen
- treated
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung eines Acyloctahydrofollikelhormons. Es ist bekannt, dass Acylderivate des Di- by drofollikelhormons zum Beispiel in der Weise erhalten werden können, dass man die .lcylderivate des Follikelhormons der Reduk tion unterwirft. Bei diesem Verfahren wer den zwei Atome Wasserstoff aufgenommen, die dazu dienen die Ketogruppen des Folli- kelhormons in die sekundäre Alkoholgruppe überzuführen.
Es wurde die Beobachtung gemacht, dass die so erhaltenen Monoacylderivate des Di- hydrofollikelhormons bei der weiteren Be- liandlung mit Wasserstoff unter Zusatz von Katalysatoren weitere sechs Atome Wasser stoff aufnehmen und in die Monoacylderi- Nate des Octahydrofollikelhormons über gehen, die sich dadurch auszeichnen, .dass sie, wie .das zugrunde liegende Octahydrofollilzel- hormon, eine wenn auch nur schwache,
dafür aber protahierte Wirkung im Sinne des männlichen Keimdrüsenhormons aufweisen.
Gegenstand vorliegenden Patentes ist nun ein Verfahren zur Darstellung eines Mono- In - octahydrofollikelhormons, dadurch gekennzeichnet, dass man das Monobenzoyl- derivat des Dihydrofollikelhormons vom F. P.<B>189'C</B> mit katalytisch erregtemWasser- stoff unter Bedingungen behandelt, bei denen der Benzolkern hydriert wird.
Die Durchführung der Hydrierung ge schieht zweckmässig durch Zufuhr von Wa.a- serstoff bei Gegenwart von Katalysatoren und wird am besten in Lösungsmitteln vor genommen.
<I>Beispiel:</I> Das -Monobenzoylderivat des Dihydro- follik elhormons vom Schmelzpunkt 189 wird in der 20fachen Menge Alkohol gelöst und mit 1/2 kg Nickel-Kupfer-Katalysator, der durch Reduktion eines Gemisches von Nickel- und Kupferoxyd im Verhältnis 1 : 1 bei 350 bis 400 erhalten wurde, versetzt und sodann bei 140' mit Wasserstoff behandelt. Nach Vollendung der Wasserstoffaufnahme wird in üblicher Weise aufgearbeitet.
Man erhält das neue Reaktionsprodukt, das als Arzneimittel Verwendung finden soll, in Form einer farblosen, glasartigen Masse, aus welcher durch Verseifung in bekannter Weise die Benzoylgruppe abgespalten werden kann. Das dann erhaltene Produkt ist identisch mit den in dem Patent Nr. 173197 beschrie benen Octahydrofollikelhormon der Formel C18H3002.
Method for the preparation of an acyloctahydrofollicle hormone. It is known that acyl derivatives of the dofollicle hormone can be obtained, for example, by subjecting the .lcyl derivatives of the follicle hormone to the reduction. In this process, two atoms of hydrogen are absorbed, which serve to convert the keto groups of the follicle hormone into the secondary alcohol group.
It was observed that the monoacyl derivatives of the dihydrofollicle hormone obtained in this way absorb a further six atoms of hydrogen on further treatment with hydrogen with the addition of catalysts and convert into the monoacyl derivatives of the octahydrofollicle hormone, which are characterized by. that, like the underlying octahydrofolil cell hormone, it is a
but have a protahed effect in the sense of the male gonadal hormone.
The subject matter of the present patent is a method for the preparation of a mono-in-octahydrofollicle hormone, characterized in that the monobenzoyl derivative of the dihydrofollicle hormone from FP <B> 189'C </B> is treated with catalytically excited hydrogen under conditions in which the benzene nucleus is hydrogenated.
The hydrogenation is expediently carried out by supplying hydrogen in the presence of catalysts and is best done in solvents.
<I> Example: </I> The monobenzoyl derivative of dihydrofollicle hormone with a melting point of 189 is dissolved in 20 times the amount of alcohol and treated with 1/2 kg of nickel-copper catalyst, which is produced by reducing a mixture of nickel and copper oxide Ratio 1: 1 was obtained at 350 to 400, added and then treated with hydrogen at 140 '. After the uptake of hydrogen is complete, it is worked up in the usual way.
The new reaction product, which is to be used as a medicament, is obtained in the form of a colorless, glass-like mass from which the benzoyl group can be split off in a known manner by saponification. The product then obtained is identical to the octahydrofollicle hormone of the formula C18H3002 described in patent no. 173197.
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DESCH101131D DE626291C (en) | 1933-05-06 | 1933-05-06 | Method for the preparation of acyloctahydrofollicle hormone |
CH176487T | 1934-05-02 | ||
DESCH104319D DE645818C (en) | 1933-05-06 | 1934-05-25 | Method for the preparation of acyloctahydrofollicle hormone |
Publications (1)
Publication Number | Publication Date |
---|---|
CH176487A true CH176487A (en) | 1935-04-15 |
Family
ID=34108250
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH176487D CH176487A (en) | 1933-05-06 | 1934-05-02 | Method for the preparation of an acyloctahydrofollicle hormone. |
CH184531D CH184531A (en) | 1933-05-06 | 1934-05-02 | Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones. |
CH184532D CH184532A (en) | 1933-05-06 | 1934-05-02 | Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones. |
CH185854D CH185854A (en) | 1933-05-06 | 1934-11-08 | Process for the preparation of a mixture of isomeric octahydrofollicle hormone diacetates. |
CH186460D CH186460A (en) | 1933-05-06 | 1934-11-08 | Process for the preparation of a mixture of isomeric octahydrofollicle hormone acetates. |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH184531D CH184531A (en) | 1933-05-06 | 1934-05-02 | Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones. |
CH184532D CH184532A (en) | 1933-05-06 | 1934-05-02 | Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones. |
CH185854D CH185854A (en) | 1933-05-06 | 1934-11-08 | Process for the preparation of a mixture of isomeric octahydrofollicle hormone diacetates. |
CH186460D CH186460A (en) | 1933-05-06 | 1934-11-08 | Process for the preparation of a mixture of isomeric octahydrofollicle hormone acetates. |
Country Status (1)
Country | Link |
---|---|
CH (5) | CH176487A (en) |
-
1934
- 1934-05-02 CH CH176487D patent/CH176487A/en unknown
- 1934-05-02 CH CH184531D patent/CH184531A/en unknown
- 1934-05-02 CH CH184532D patent/CH184532A/en unknown
- 1934-11-08 CH CH185854D patent/CH185854A/en unknown
- 1934-11-08 CH CH186460D patent/CH186460A/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH185854A (en) | 1936-08-15 |
CH184531A (en) | 1936-05-31 |
CH186460A (en) | 1936-09-15 |
CH184532A (en) | 1936-05-31 |
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