CH189749A - Method for the preparation of 17-methyl-dihydrofollicle hormone. - Google Patents
Method for the preparation of 17-methyl-dihydrofollicle hormone.Info
- Publication number
- CH189749A CH189749A CH189749DA CH189749A CH 189749 A CH189749 A CH 189749A CH 189749D A CH189749D A CH 189749DA CH 189749 A CH189749 A CH 189749A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- hormone
- methyl
- organometallic compound
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 239000005556 hormone Substances 0.000 title claims description 8
- 229940088597 hormone Drugs 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000002902 organometallic compounds Chemical class 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000004567 concrete Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000010453 quartz Substances 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung von 17-1Vlethyl-diliydrofollikelhormon. Gegenstand der vorliegenden Erfindung isst ein Verfahren zur Darstellung von 17- 1vlethyl-dihydrofollikelhormon, welches da durch gekennzeichnet ist, dass man F'ollikel- hoimon der Formel C,sH2202 mit einer für dio Umwandlung von Ketonen in Methyl- karbinole geeigneten metallorganischen Ver bindung,
beispielsweise nach der Methode von Grignard mit Methylmagnesiumjodid, umsetzt und das dabei gebildete Umsetzungs produkt mit Hilfe hydrolysierend wirkender Mittel aufspaltet. Bei .der Aufarbeitung des Reaktionsgemisiehes erhält man dann 17- Methyl-dihydrofollikelhormon -der Formel C1sH2602 in kristalliner Form. Es, soll zur Behebung physiologischer Ausfallerschei nungen verwendet werden.
Das erfindungsgemässe Verfahren sei im folgenden für die Verwendung von Methyl- magnes:iumjodid als metallorganischer Ver bindung durch Formelbilder veranschaulicht:
EMI0001.0026
Die für das, vorliegende Verfahren in Be tracht kommenden, für die Umwandlung von Betonen in Methylkarbinole geeigneten me tallorganischen Verbindungen sind in ihrer Verwendungsweise z. B. beschrieben in Houben-Weyl, Methoden der organ. Chemie, 3. Band, 2. Aufl. (l923), Seite<B>61</B> ff.
<I>Beispiel:</I> 1 g kristallisiertes Follikelhormon vom Schmelzpunkt 253 bis 256 wird in absolu tem, über Natrium getrocknetem Äther ge löst. Die ätherische Lösung des. Hormons wird dann zu einer ätherischen Lösung von überschüssigem, in bekannter Weise herge- @stelltem Methylmagnesiumjodid hinzuge- tropft und die Reaktionslösung im Anschluss daran noch etwa i/2 iStunde zum Sieden er hitzt.
Nach dem Erkalten wird die Reak tionsflüssigkeit mit Salzsäure angesäuert und nach dem Verdünnen mit Wasser mit Äther ausgeschüttelt. Nach dem Trocknen und Verdampfen des Äthers wird das, Reak tionsprodukt in kristalliner Form erhalten.
Das verfahrensgemäss erhältliche Reak- tionsprodukt ist neu; es besteht entsprechend der Theorie aus einem Gemisch zweier iGo- merer Methy lkarbinole und zeigt in kon zentrierter .Schwefelsäure im Lichte der Analysenquarzlampe eine blaugrüne Farbe und Fluoreszenz.
Der physiologische Wir kungswert des Präparates im Allen-Doisy- Test beträgt bei subkutaner Verabfolgung in wässriger Lösung und sechsmaliger Untertei lung 3 bis -4 Millionen Ratteneinheiten pro Gramm, während das Follikelhormon der Formel C1gA.-_0@ nur eine Wirksamkeit von etwa 1,2 Millionen Ratteneinheiten pro Gramm aufweist.
Method for the preparation of 17-1Vlethyl-diliydrofollicle hormone. The subject matter of the present invention is a process for the preparation of 17- 1vlethyl-dihydrofollicle hormone, which is characterized in that F'ollikel- hoimon of the formula C, sH2202 with an organometallic compound suitable for the conversion of ketones into methyl carbinols,
for example, according to the Grignard method with methyl magnesium iodide, and the reaction product thus formed splits up with the aid of hydrolyzing agents. When working up the reaction mixture, 17-methyl-dihydrofollicle hormone of the formula C1sH2602 is obtained in crystalline form. It should be used to correct physiological failure phenomena.
The process according to the invention is illustrated below for the use of methyl magnes: ium iodide as an organometallic compound using formulas:
EMI0001.0026
The for the, present process in consideration, suitable for the conversion of concretes in methyl carbinols me tallorganischen compounds are in their use z. B. described in Houben-Weyl, Methods of organ. Chemie, 3rd volume, 2nd edition (1923), page <B> 61 </B> ff.
<I> Example: </I> 1 g of crystallized follicular hormone with a melting point of 253 to 256 is dissolved in absolute ether dried over sodium. The ethereal solution of the hormone is then added dropwise to an ethereal solution of excess methylmagnesium iodide prepared in a known manner, and the reaction solution is then heated to boiling for about half an hour.
After cooling, the reaction liquid is acidified with hydrochloric acid and, after diluting with water, shaken out with ether. After drying and evaporation of the ether, the reaction product is obtained in crystalline form.
The reaction product obtainable according to the process is new; According to the theory, it consists of a mixture of two iGomer methyl carbinols and, in concentrated sulfuric acid, shows a blue-green color and fluorescence in the light of the analytical quartz lamp.
The physiological effect value of the preparation in the Allen-Doisy test is 3 to -4 million rat units per gram when administered subcutaneously in aqueous solution and subdivided six times, while the follicular hormone of the formula C1gA.-_ 0 @ only has an effectiveness of about 1.2 Has millions of rat units per gram.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE189749X | 1933-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH189749A true CH189749A (en) | 1937-03-15 |
Family
ID=5721464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH189749D CH189749A (en) | 1933-10-21 | 1934-10-20 | Method for the preparation of 17-methyl-dihydrofollicle hormone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH189749A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2713062A (en) * | 1952-08-08 | 1955-07-12 | Schering Ag | 3-methyl-17-ethinyl androstandiols |
| DE941668C (en) * | 1952-08-09 | 1956-04-19 | Schering Ag | Process for the preparation of alcohols of the cyclopentanopolyhydrophenanthrene series |
| US2857405A (en) * | 1953-05-15 | 1958-10-21 | Boehringer & Soehne Gmbh | Process of preparing 17-methyl-estradiol |
-
1934
- 1934-10-20 CH CH189749D patent/CH189749A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2713062A (en) * | 1952-08-08 | 1955-07-12 | Schering Ag | 3-methyl-17-ethinyl androstandiols |
| DE941668C (en) * | 1952-08-09 | 1956-04-19 | Schering Ag | Process for the preparation of alcohols of the cyclopentanopolyhydrophenanthrene series |
| US2857405A (en) * | 1953-05-15 | 1958-10-21 | Boehringer & Soehne Gmbh | Process of preparing 17-methyl-estradiol |
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