DE729758C - Process for the preparation of hydrogenation products of the follicular hormone series - Google Patents
Process for the preparation of hydrogenation products of the follicular hormone seriesInfo
- Publication number
- DE729758C DE729758C DESCH102836D DESC102836D DE729758C DE 729758 C DE729758 C DE 729758C DE SCH102836 D DESCH102836 D DE SCH102836D DE SC102836 D DESC102836 D DE SC102836D DE 729758 C DE729758 C DE 729758C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- follicular
- hydrogenation products
- hydrogenation
- follicular hormone
- 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.)
- Expired
Links
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Darstellung von Hydrierungsprodukten der Follikelhormonreihe In dem Patent 698 796 ist gezeigt worden, daß man das Follikelhormon der Formel C1sH@.Oz durch Einwirkung von katalytisch erregtem Wasserstoff in Dihy drofollikelhormon der Formel C"H.,0., überführen kann, ohne daß dabei gleichzeitig der Benzolring angegriffen wird. Das so erhältliche Dihydrofollikelhormon ist wegen seiner außerordentlich hohen physiologischen Wirksamkeit von großer therapeutischer B-edeutun,g.Process for the preparation of hydrogenation products of the follicular hormone series It was shown in the '698,796 patent that one can obtain the follicular hormone of the formula C1sH @ .Oz by the action of catalytically excited hydrogen in dihydrofollicle hormone of the formula C "H., 0., without the benzene ring at the same time is attacked. The dihydrofollicle hormone thus obtainable is extraordinary because of its high physiological effectiveness of great therapeutic significance, g.
Es wurde die Beobachtung ,gemacht, d:aß es gelingt, die Ketogruppe in den Follikelhormonen in die sekundäre Alkoholgruppe. umzuwandeln, indem man die Follikelhormone in Gegenwart von Hydrierungsk.atalysato-ren mit Verbindungen behandelt, die Wasserstoff enthalten und fähig sind, diesen Wasserstoff abzugeben, wobei die genannten Verbindungen selbst dehydriert bzw. oxydiert werden. Solche Verbindungen sind z. B. die hydrierten Benzole und Naphthaline und ihre Derivate., wie das Cyclohexanol, Tetralin u. dgl., oder Isoborneol oder Piperidin und ähnliche Verbindungen. Man kann auch höher hydrierte Follikelhormone verwenden, in denen der Benzolring bereits hydriert ist und die z. B. nach dem Verfahren des Patents 672 958 erhalten werden. Beispiel Äduimolekulare Mengen von Cyclohexanol und Follikelhörmon werden unter kräftigem Rühren in einem Autoklaven in Gegenwart von etwa 5 o,'o ihres Gewichtes eines Hydrierungskatalysators auf etwa 2oo° erhitzt. Der Beginn der Reaktion wird durch den plötzlichen Druckanstieg ,angezeigt. Ihm folgt nach einiger Zeit ein Fallen des Druckes. Nach wenigen Stunden wird die Reaktion unterbrochen, die Reaktionsprodukte werden vom Katalysator getrennt, das gebildete Cyclohexanon und das nicht in Reaktion getretene Cyclohexanol werden durch Vakuumdestillation entfernt, der Rückstand wird in Alkohol gelöst, das nicht in Reaktion getretene Follikelhormon als Semicarbazon niedergeschlagen und ,aus der .alkoholischen Lösung durch Verdampfen des Alkohols .das Dihydrofollikelhormor isoliert, das in einer Ausbeute von etwa 3o 0,'o des eingesetzten Follikelhormons anfällt.The observation was made that the keto group succeeded in the follicular hormones to the secondary alcohol group. convert by using the Follicle hormones treated with compounds in the presence of hydrogenation catalysts, which contain hydrogen and are capable of releasing this hydrogen, the compounds mentioned are themselves dehydrated or oxidized. Such connections are z. B. the hydrogenated benzenes and naphthalenes and their derivatives., Such as cyclohexanol, Tetralin and the like, or isoborneol or piperidine and the like. Man can also use higher hydrogenated follicular hormones in which the benzene ring already exists is hydrogenated and the z. By the method of patent 672,958. Example Äduimolecular amounts of cyclohexanol and follicular hormone are under vigorous stirring in an autoclave in the presence of about 5 o, 'o of their weight a hydrogenation catalyst heated to about 2oo °. The beginning of the reaction will indicated by the sudden increase in pressure. After a while it is followed by a fall of pressure. After a few hours the reaction is interrupted, the reaction products are separated from the catalyst, the cyclohexanone formed and not in reaction Cyclohexanol which has entered is removed by vacuum distillation, the residue becomes Dissolved in alcohol, the unreacted follicular hormone as semicarbazone precipitated and, from the .alcoholic solution by evaporation of the alcohol .the dihydrofollicle hormone isolated that in a yield of about 30% of the follicular hormone used is obtained.
Andere Verbindungen, z. B. Tetrahydronaphthalin oder auch die höher hydrierten Follikelhormone, die z. B. einen hydrierten Benzolring enthalten, können an Stelle von Cycloheranol venaendet werden.Other connections, e.g. B. tetrahydronaphthalene or the higher hydrogenated follicular hormones, e.g. B. contain a hydrogenated benzene ring be used in place of cycloheranol.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DESCH102836D DE729758C (en) | 1933-12-07 | 1933-12-07 | Process for the preparation of hydrogenation products of the follicular hormone series |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DESCH102836D DE729758C (en) | 1933-12-07 | 1933-12-07 | Process for the preparation of hydrogenation products of the follicular hormone series |
Publications (1)
Publication Number | Publication Date |
---|---|
DE729758C true DE729758C (en) | 1943-01-04 |
Family
ID=7447333
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DESCH102836D Expired DE729758C (en) | 1933-12-07 | 1933-12-07 | Process for the preparation of hydrogenation products of the follicular hormone series |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE729758C (en) |
-
1933
- 1933-12-07 DE DESCH102836D patent/DE729758C/en not_active Expired
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