CH207671A - Process for the preparation of an oxyketone of the androsten series. - Google Patents
Process for the preparation of an oxyketone of the androsten series.Info
- Publication number
- CH207671A CH207671A CH207671DA CH207671A CH 207671 A CH207671 A CH 207671A CH 207671D A CH207671D A CH 207671DA CH 207671 A CH207671 A CH 207671A
- Authority
- CH
- Switzerland
- Prior art keywords
- process according
- oxidizing agent
- agent
- halogen
- dependent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims 2
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000012433 hydrogen halide Substances 0.000 claims description 6
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkali metal acetates Chemical class 0.000 claims description 4
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 4
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000005751 Copper oxide Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910000431 copper oxide Inorganic materials 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 150000001443 androstenes Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 4
- 238000003776 cleavage reaction Methods 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000007017 scission Effects 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000007256 debromination reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QJTAAHJJXWYZSK-UHFFFAOYSA-N [Br].CC(O)=O Chemical compound [Br].CC(O)=O QJTAAHJJXWYZSK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002506 high-vacuum sublimation Methods 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Oxykotons der Androstenreihe. Es wurde gefunden, dass man zu einem Oxyketon der Androstenreihe gelangen kann, wenn man die Doppelbindung eines in 17- Stellung veresterten A5,6-Androsten-17-eis- diols-(3,14) der Formel
EMI0001.0010
vor der folgengen Einwirkung des Oxydations mittels schützt, auf das so erhaltene Zwi schenprodukt ein Oxydationsmittel einwirken lässt,
hierauf die Kohlenstoff-Doppelbindung unter Verschiebung in 4,5-Stellung regeneriert und die so erhaltene Verbindung verseift.
Das so gewonnene dI,1-Androsten-3-on- 17-eis-ol der Formel
EMI0001.0017
bildet farblose Kristalle vom F. 200-2210. Wie Versuche ergaben, gelingt es leicht das Oxyketon entweder durch direkte Kri stallisation oder durch Bereitung schwer löslicher Derivate in reiner Form abzuschei den.
Solche schwer lösliche Derivate erhält man zum Beispiel durch Umsetzung des Oxy- ketons mit den üblichen Ketonreagenzien -wie Semicarbazid, Thiosemicarbazid, Hydroxyl- amin, Aminoguanidin, Phenylhydrazinen, neu tralen oder basischen Acylhydraziden. Zur Reinigung und<B>-</B> Trennung erwies sich auch die Acylierung mit Acylierungsmittein wie Acetanhydrid, Benzoylchlorid,
Dinitrobenzoyi- chlorid als vorteilhaft. Durch Einwirkung hydrolytisch wirkender Mittel werden die zwecks Reinigung des Oxyketons hergestell ten Verbindungen wieder in ihre Komponen ten gespalten.
Geeignete Oxydationsmittel sind zum Beispiel 6wertige Chromverbindungen, wie Chromsäure in Eisessig, ferner Kupferoxyd, Permanganat und dergleichen. Der Schutz der Kohlenstoffdoppelbindung ei-folgt zum Beispiel durch Anlagerung von Halogen bezw. Halogenwasserstoff an den Ausgangsstoff.
Nach erfolgter Oxydation wird die Kohlen- stoffdoppelbindung unter Verschiebung in 4,5-Stellung regenerlert. Die Entfernung des Halogens kann in bekannter Weise zum Beispiel durch Zinkstaub und Essigsätire oder Benzol, durch katalytisch angeregten Wasser stoff oder durch Behandeln mit Alkalijodiden, und die des Halogenwasserstoffes zum Beispiel durch tertiäre Basen wie Pyridin oder Di- methylanilin oder durch Umsetzen mit Salzen von Carbonsäuren,
wie zum Beispiel Alkali- acetaten, erfolgen.
Die erhaltene Verbindung soll therapeuti sche Verwendung finden.
<I>Beispiel<B>1:</B></I> <B>1,5 g</B> 17-Monoacetat des J5,6-3-traris-17- eis-Androsteridiols werden in<B>30</B> cm' Eisessig gelöst und mit der berechneten Menge<B>(1</B> Mol) Brom in Eisessig versetzt. Das Brom wird sofort entfärbt. Man fügt eine Lösung von <B>1</B> Mol Chromsäure in 90 %iger Essigsäure hinzu und lässt über Nacht bei Zimmertem peratur stehen.
Das Reaktionsprodukt wird dann mit Wasser ausgefällt und abfiltriert. Es wird durch 48stündiges Schütteln mit Zinkstaub in alkoholischer Lösung entbronit und schliesslich durch Umkristallisieren aus Ilexan gereinigt. Aus dem erhaltenen Acetat des dI,5-Andf-osteri-eis-ol-(17)-ori-(3) vom F.<B>1150</B> gewinnt man durch Verseifen mit 21/oio,er methylalkoliolischer Kalilauge das 23 <I>A4,</I> 5-Androsten-eis-ol-(17)-on-(3) vom F. 220 bis 221<B>0.</B>
An Stelle des Acetats können auch andere Ester, wie zum Beispiel das Propionat, ein Butyrat, ein Valerianat, das Berizoat oder auch Ester anorganischer Säuren wie der Ila- logenwasserstoffsäuren, Verwendung finden.
Statt durch Brom lässt sich die Doppel bindung zum Beispiel auch durch Chlor schützen.
<I>Beispiel 2:</I> 2,1<B>g</B> A3#l;-Androsten-S-ti-aiis-17-eis-diol-17- benzoat vom F.<B>150-1510</B> nimmt man in <B>50</B> ein3 Eisessig auf und gibt unter Kühlung tropfenweise die berechnete Menge einer Bromeisessiglösung zu. Schliesslich wird<B>0,5 g</B> Chromtrioxyd, gelöst in 15 em3 90 %iger Essigsäure, in der Kälte zugefügt und das Ganze über Nacht bei Zimmertemperatur stehen gelassen, wobei das Oxlvdationsprodukt teilweise auskristallisiert.
Dann giesst man in Wasser, saugt das ausgefallene Produkt ab und wäscht mit viel Wasser nach. Das so erhaltene bromierte Keton behandelt man zur Entbromung in Eisessig mit Zinkstaub unter intensivem Schütteln auf dem siedenden Wasserbade. Dann wird abgesaugt, nachge waschen und die Lösung mit Wasser gefällt. Man zieht mit Äther aus, schüttelt die Äther lösung mit verdünnter Sodalösung und Wasser und dampft sie ein.
Die Entbromung kann aber auch zum Beispiel durch Erhitzen einer trockenen benzolischen Lösung des gebromten Ketons mit einer alkoholischen Lösung von Natriumjodid durchgeführt werden. In diesem Falle wird die Lösung nachher mit wässei-i- ger Natriumsulfitlösung und Wasser ge waschen und eingedampft.
Aus dem nach einer dieser Methoden gewonnenen Rohprodukt lässt sich zum Bei spiel durch Umkristallisation aus Hexan und/oder Hochvakuumsublimation oder auch über das schwer lösliche Seinicarbbazon das JI,71-Aiidi-osteii-3-on-17-eis-ol-benzoat vom F. 135-136" erhalten. Durch Verseifung zum Beispiel mit alkoholischer Lauge wird es ins freie Oxyketon, dasi dI,#l-Andi,osten-3- on-17-eis-ol vom F. '2220-2211 übergeführt.
Zur Oxydation kann man an Stelle von Chromsäure zum Beispiel auch Kupferoxyd verwenden.
Method for the representation of an oxycotone of the androsten series. It has been found that an oxyketone of the androstene series can be obtained if the double bond of a 17-esterified A5,6-androstene-17-cisdiols- (3.14) of the formula
EMI0001.0010
protects against the subsequent effects of the oxidizing agent, allowing an oxidizing agent to act on the intermediate product thus obtained,
the carbon double bond is then regenerated by shifting it to the 4,5 position and the compound thus obtained is saponified.
The dI, 1-androsten-3-one-17-eis-ol of the formula obtained in this way
EMI0001.0017
forms colorless crystals of F. 200-2210. As experiments have shown, it is easy to separate the oxyketone either by direct crystallization or by preparing poorly soluble derivatives in pure form.
Such poorly soluble derivatives are obtained, for example, by reacting the oxy ketone with the usual ketone reagents such as semicarbazide, thiosemicarbazide, hydroxylamine, aminoguanidine, phenylhydrazines, neutral or basic acylhydrazides. For purification and <B> - </B> separation, acylation with acylating agents such as acetic anhydride, benzoyl chloride,
Dinitrobenzoyi chloride as advantageous. By the action of hydrolytic agents, the compounds produced for the purpose of cleaning the oxyketone are split back into their components.
Suitable oxidizing agents are, for example, hexavalent chromium compounds, such as chromic acid in glacial acetic acid, also copper oxide, permanganate and the like. The protection of the carbon double bond follows, for example, by the addition of halogen or. Hydrogen halide to the starting material.
After oxidation has taken place, the carbon double bond is regenerated by shifting it to the 4,5 position. The halogen can be removed in a known manner, for example by zinc dust and acetic acid or benzene, by catalytically excited hydrogen or by treatment with alkali iodides, and that of the hydrogen halide, for example by tertiary bases such as pyridine or dimethylaniline or by reaction with salts of carboxylic acids ,
such as, for example, alkali acetates.
The compound obtained should be used therapeutically.
<I>Example<B>1:</B> </I> <B> 1.5 g </B> 17-monoacetate of J5,6-3-traris-17-cis-androsteridiol are used in <B> 30 </B> cm 'dissolved in glacial acetic acid and added the calculated amount of <B> (1 </B> mol) bromine in glacial acetic acid. The bromine is immediately decolorized. A solution of 1 mol of chromic acid in 90% acetic acid is added and the mixture is left to stand overnight at room temperature.
The reaction product is then precipitated with water and filtered off. It is entbronitized by shaking with zinc dust in an alcoholic solution for 48 hours and finally purified by recrystallization from Ilexan. The obtained acetate of dI, 5-Andf-osteri-eis-ol- (17) -ori- (3) from F. 1150 is obtained by saponification with 21% of methyl alcoholic potassium hydroxide solution 23 <I> A4, </I> 5-Androsten-eis-ol- (17) -on- (3) from F. 220 to 221 <B> 0. </B>
Instead of the acetate, it is also possible to use other esters, such as propionate, a butyrate, a valerate, berizoate, or esters of inorganic acids such as the halogenated hydrochloric acids.
Instead of using bromine, the double bond can also be protected using chlorine, for example.
<I> Example 2: </I> 2.1 <B> g </B> A3 # l; -androsten-S-ti-aiis-17-cis-diol-17-benzoate from F. <B> 150 -1510 </B> take up a3 glacial acetic acid in <B> 50 </B> and add the calculated amount of a bromine acetic acid solution drop by drop while cooling. Finally, 0.5 g of chromium trioxide, dissolved in 15 cubic centimeters of 90% acetic acid, is added in the cold and the whole is left to stand overnight at room temperature, the oxidation product partially crystallizing out.
Then it is poured into water, the precipitated product is filtered off with suction and washed with plenty of water. The brominated ketone obtained in this way is treated for debromination in glacial acetic acid with zinc dust while shaking vigorously on the boiling water bath. Then it is suctioned off, washed afterwards and the solution is precipitated with water. One pulls out with ether, shakes the ether solution with dilute soda solution and water and evaporates it.
The debromination can, however, also be carried out, for example, by heating a dry benzene solution of the brominated ketone with an alcoholic solution of sodium iodide. In this case, the solution is then washed with aqueous sodium sulfite solution and water and evaporated.
From the crude product obtained by one of these methods, for example, by recrystallization from hexane and / or high vacuum sublimation or via the sparingly soluble Seinicarbbazon, the JI, 71-Alidi-osteii-3-one-17-cis-ol-benzoate from F. 135-136 ". By saponification, for example with alcoholic lye, it is converted into the free oxyketone, dasi dI, # l-Andi, osten-3-on-17-eis-ol from F. '2220-2211.
For oxidation, instead of chromic acid, for example, copper oxide can also be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH207671T | 1935-06-18 | ||
| CH202366T | 1935-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH207671A true CH207671A (en) | 1939-11-15 |
Family
ID=25723792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH207671D CH207671A (en) | 1935-06-18 | 1935-06-18 | Process for the preparation of an oxyketone of the androsten series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH207671A (en) |
-
1935
- 1935-06-18 CH CH207671D patent/CH207671A/en unknown
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