CH194280A - Method for the preparation of 17-methyloctahydrofollicle hormone. - Google Patents
Method for the preparation of 17-methyloctahydrofollicle hormone.Info
- Publication number
- CH194280A CH194280A CH194280DA CH194280A CH 194280 A CH194280 A CH 194280A CH 194280D A CH194280D A CH 194280DA CH 194280 A CH194280 A CH 194280A
- Authority
- CH
- Switzerland
- Prior art keywords
- hormone
- formula
- preparation
- methyloctahydrofollicle
- hydrogen
- Prior art date
Links
- 229940088597 hormone Drugs 0.000 title claims description 11
- 239000005556 hormone Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000010453 quartz Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0085—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Description
Verfahren zur Darstellung von 17-Methyloctahydrofollikelhormon. Gegenstand vorliegenden Patentes ist ein Verfahren zur Darstellung von 17-Methylocta- hydrofollikelhormon der Formel CisHs202, welches dadurch gekennzeichnet ist, dass man 17-Methyldihydrofollikelhormon der Formel CiaH2r,02 mit einem hydrierenden Mittel bis zur Aufnahme von 6 Atomen Wasserstoff be handelt,
Das als Ausgangsmaterial für das vorlie gende Verfahren dienende 17-111-ethyldihydro- follikelhormon der Formel CisH2602 kann z. B. gemäss dem Verfahren des Patentes Nr. 189749 durch Umsetzung von Follikelhormon der Formel CisH2202 mit Methylmagnesiumjodid dargestellt werden.
Als hydrierendes Mittel kann man kata lytisch erregten Wasserstoff oder auch Wasser stoff, der auf andere Art und Weise aktiviert worden ist, z. B. atomaren Wasserstoff oder Wasserstoff in statu nascendi, wie er bei spielsweise durch die Einwirkung von Na triummetall auf die alkoholische Lösung des Ausgangsmaterials erhalten wird, verwenden. <I>Beispiel:</I> 1,5 g 17-Methyldihydrofollikelhormon der Formel 019H2602 werden in<B>150 cm'</B> reinem Eisessig gelöst und die Lösung nach Zugabe von 200 mg Platinogydkatalysator nach Adams-Shriner ca. 18 Stunden in einer Was serstoffatmosphäre geschüttelt.
Nach Auf nahme von 6 Atomen Wasserstoff kommt die Hydrierung praktisch zum Stillstand. Die vom Katalysator befreite Reaktionslösung wird darauf im Vakuum zur Trockne abgedampft. Es hinterbleibt ein schwach gelb gefärbtes sprödes Harz, das bei der Kohlenstoff- und Wasserstoff-Bestimmung auf die Formel Ci9H3202 stimmende Werte ergibt.
Das so erhaltene 17-Methyloctahydrofol- likelhormon der Formel Ci9H3202 ist ein neues Produkt; es löst sich in konzentrierter Schwe felsäure mit rein gelber Farbe und zeigt in dieser Lösung, unter der Analysenquarzlampe betrachtet, ebenfalls eine gelbe Farbe und Fluoreszenz, während das Ausgangsmaterial unter denselben Bedingungen eine blaugrüne Farbe und Fluoreszenz aufweist, Das 17-1Vlethyloctahydrofollikelhormon der Formel 019H8202 soll für therapeutische Zwecke verwendet werden;
es zeigt bei phy siologischer Prüfung im Kapaunenkammtest einen Wirkungswert von 4 mg pro Kapaunen einheit.
Method for the preparation of 17-methyloctahydrofollicle hormone. The subject of the present patent is a process for the preparation of 17-methylocta hydrofollicle hormone of the formula CisHs202, which is characterized in that 17-methyldihydrofollicle hormone of the formula CiaH2r, 02 is treated with a hydrogenating agent up to the absorption of 6 atoms of hydrogen,
The starting material for the present process 17-111-ethyldihydro- follicle hormone of the formula CisH2602 can, for. B. can be prepared according to the method of patent no. 189749 by reacting follicle hormone of the formula CisH2202 with methyl magnesium iodide.
As a hydrogenating agent you can kata lytically excited hydrogen or hydrogen that has been activated in other ways, eg. B. atomic hydrogen or hydrogen in statu nascendi, as obtained for example by the action of Na trium metal on the alcoholic solution of the starting material, use. <I> Example: </I> 1.5 g of 17-methyldihydrofollicle hormone of the formula 019H2602 are dissolved in <B> 150 cm '</B> pure glacial acetic acid and the solution after adding 200 mg of Adams-Shriner platinogyd catalyst is approx Shaken in a hydrogen atmosphere for hours.
After 6 atoms of hydrogen have been absorbed, the hydrogenation practically comes to a standstill. The reaction solution freed from the catalyst is then evaporated to dryness in vacuo. What remains is a pale yellow, brittle resin which, when determining carbon and hydrogen, gives values that correspond to the formula Ci9H3202.
The 17-methyloctahydrofollil hormone of the formula Ci9H3202 obtained in this way is a new product; It dissolves in concentrated sulfuric acid with a purely yellow color and in this solution, viewed under the analysis quartz lamp, also shows a yellow color and fluorescence, while the starting material has a blue-green color and fluorescence under the same conditions used for therapeutic purposes;
In a physiological test in the capon comb test, it shows an action value of 4 mg per capon unit.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH194280T | 1935-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH194280A true CH194280A (en) | 1937-11-30 |
Family
ID=4439346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH194280D CH194280A (en) | 1935-02-22 | 1935-02-22 | Method for the preparation of 17-methyloctahydrofollicle hormone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH194280A (en) |
-
1935
- 1935-02-22 CH CH194280D patent/CH194280A/en unknown
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