CH332324A - Process for the preparation of 16B-acyloxy-17a-oxy-20-oxo-pregnanes - Google Patents
Process for the preparation of 16B-acyloxy-17a-oxy-20-oxo-pregnanesInfo
- Publication number
- CH332324A CH332324A CH332324DA CH332324A CH 332324 A CH332324 A CH 332324A CH 332324D A CH332324D A CH 332324DA CH 332324 A CH332324 A CH 332324A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- parts
- oxo
- free
- volume
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- 239000013543 active substance Substances 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 copper oxide Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- GGEPMWAXNJCOPK-UHFFFAOYSA-N 2-methylpropan-2-ol;pyridine Chemical compound CC(C)(C)O.C1=CC=NC=C1 GGEPMWAXNJCOPK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 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
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- VTHIKKVKIVQWHV-UHFFFAOYSA-N chromium(6+) oxygen(2-) pyridine Chemical compound [O-2].[O-2].[O-2].[Cr+6].C1=CC=NC=C1 VTHIKKVKIVQWHV-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940119740 deoxycorticosterone Drugs 0.000 description 1
- 229960004486 desoxycorticosterone acetate Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 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 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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)
- Steroid Compounds (AREA)
Description
Verfahren zur Herstellung von 16ss-Acyloxy-17a-oxy-20-oxo-pregnanen Die Erfindung betrifft ein Verfahren zur Herstellung von gesättigten oder ungesättig- ten 16f3- Acyloxy-17a-oxy-20-oxo-pregnauen, welche in 3-.Stellung eine freie oder geschützte Oxy- oder Oxobgruppe,
in 21-.Stellung eine freie oder geschützte Oxygruppe und ausser dem gegebenenfalls weitere Substituenten aufweisen, das dadurch gekennzeichnet ist, dass man in die entsprechenden 16,17arOxido- Verbindungen durch Behandlung mit alipha- tisehen Carbonsäuren aufspaltet..
Ausser einer freien Oxy- oder Oxogruppe können die Verbindungen in 3-Stellung z. B. eine veresterte Oxygrüppe oder eine ketali- sierte Oxogruppe enthalten. Ferner können ausserdem noch weitere Substituenten vor handen sein, z. B. eine Oxy- oder Oxogruppe in 11-Stellung und Doppelbindungen z. B. ausgehend vom Kohlenstoffatom 5.
Die erfindungsgemäss erhältlichen Verbin dungen sind besonders wertvoll, weil sie interessante pharmakologische Eigenschaften besitzen. Insbesondere das 17a-Oxy-16ss-acet- oxy-desoxycorticosteron-acetat weist eine aus gesprochene Nebennierenrindenhormon-Wir- kung auf, welche im Wirkungstypus von der jenigen z. B. des 17 rOxy-desoxycorticosterons abweicht und sie teilweise übertrifft.
Zur Aufspaltung des 0xydringes verwen det man vorzugsweise aliphatische Carbon- säuren mit mindestens 2 C-Atomen, d.-h. Essigsäure und höhere. Gegebenenfalls wer den zur Spaltung auch Katalysatoren zuge setzt. Besonders günstig wirkt sich der Zu satz von konz. Schwefelsäure axis.
Sofern die Ausgangsstoffe neu sind, lassen sie sich nach bekannten Methoden gewinnen. Sofern die Verfahrensprodukte Zwischen produkte sind, kann man sie nach an sich bekannten Methoden in physiologisch wirk same Verbindungen, vorzugsweise solche, die die d4-3-getogruppierung aufweisen,
-an- wandeln. Insbesondere kann eine Acyloxy- gruppe in 3-Stellung durch gelinde Einwir- kung alkalischer, oder saurer Mittel, bei spielsweise von Hydrogencarbonatlösung oder verdünnter Mineralsäure, hydrolysiert wer den. In erhaltenen Verbindungen mit freier 3-Hydroxylgruppe lässt sich letztere in an sich bekannter Weise durch dehydrierende Mittel in eine Oxogruppe umwandeln. Hierzu dienen z. B.
Chromsäure in Eisessig, Chrom (VI)-salze in saurem Medium, Chromtrioxyd- Pyridin-gssmplex, Permanga-nate, Metall-Al- koholate oder -Phenolate in Gegenwart von Ketonen, N-Broma.cetamid, beispielsweise in Dioxan-Wasser oder Pyridin-t-Butanol, Hy- pohalogenite, Erhitzen mit Metallen oder Me talloxyden, wie Kupferoxyd usw.
Eine Dop pelbindung in 5;6-Stellung lässt sich vorüber gehend durch AnIagerung von Halogen oder Halogenwasserstoff oder durch Überführung in i-#Steroide schützen. Schliesslich lässt sich in im Ring A gesät tigte Reaktionsprodukte mit freier 3-0_xo- gruppe in a-Stellung zu derselben in bekann ter Weise eine Doppelbindung einführen.
Vorteilhaft wird hierzu bromiert, mit einem Hydrazid, wie Semicarbazid, umgesetzt und das Hydrazon mittels einer Carbonylverbin- dung, wie Brenztraubensäure, gespalten.
<I>Beispiel 1</I> 9 Gewichtsteile d4 - 21- Acetoxy -16,17a - oxido-pregnen-3,20 dion vom F.
= 165-167 (in an sich bekannter Weise aus d4.16-21- Acetoxy - pregnadien - 3,20 - dion hergestellt) werden in 180 Volumteilen Eisessig und 25 Volumteilen konzentrierter Schwefelsäure 10 Stunden bei + 10 stehengelassen. Die Lief rote, fluoreszierende Reaktionslösung giesst man dann in 2000 Volumteile Wasser und extrahiert mehrmals mit Äther.
Die vereinig ten Ätherlösungen werden mit Wasser, ver dünnter Natriumbicarbonatlösung und Wasser gewaschen, getrocknet und eingedampft. Man erhält 10 Gewichtsteile eines gelben öls, wel ches in 100 Volumteilen Benzol gelöst und an einer Säule von 250 Gewichtsteilen Alumi niumoxyd chromatographiert wird. Durch Eluieren mit Benzol gewinnt man etwa, 3 Ge wichtsteile Ausgangsmaterial zurück.
Mit einem Gemisch von gleichen Volumteilen Benzol und Äther werden 3,5 Gewichtsteile eines farblosen öls eluiert, aus dem man durch Kristallisation aus Äther das reine d4-16ss,21-D.ifacetoxy-pregnen,17,a-ol-3,20-dion vom F. = 167-168 gewinnt. Es weist bei 241 mu ein starkes A.bsorptionsmaxiiniun (a <I>=</I> 17000) und die spez. Drehung [a] <I>D =</I> + 99 (in Chloroforih) auf.
Die Acetylgruppen können wie folgt ver seift werden: 2,6 Gewichtsteile der D.iacetoxy- verbinduug löst man in 6 Volumteilen Me thanol und gibt eine Methylatlösung aus 0,3 Gewichtsteilen Natriiun und 22 Volum- teilen Methanol zu.
Nach - 3 Minuten .fügt man 10 Volumteile einer Mischung gleicher Volumteile Wasser -und Methanol zu und säuert nach weiteren 3 Minuten mit 1 Vohun- teil Eisessig an. Das Reaktionsgemisch wird -dann im Vakuum auf ein kleines Volumen eingeengt, mit 200 Volurnteilen Wasser ver setzt und mit Chloroform extrahiert.
Aus dem mit Wasser, Natriumbicarbonatlösung und Wasser gewaschenen und getrockneten Chloroformextrakt erhält man nach Ein- dampfen des Lösungsmittels auf Zusatz von Aceton 1,86 Gewichtsteile eines gristallisates. Durch Umkristallisieren aus Aceton und aus Isopropyläther gewinnt man das Triol vom F. = 208-212 .
<I>Beispiel 2</I> 0,5 Gewichtsteile d5 - 3ss,21- Diacetox-y- 16,17a-oxido-pregnen-20-on (in an sich be kannter Weise aus dem 4.s,16-3ss,21-Diacetoxy- pregnaäien-20-on hergestellt) vom F.
= 170 bis 173 werden in 10 Volumteilen Eisessig gelöst, mit einem Voliunteil einer Mischling von 10 Volumteilen Eisessig und 2,5 Volum- teilen konz. Schwefelsäure versetzt und 9 Stunden bei Raumtemperatur gut verschlos sen stehengelässen. Dann wird die braunrote Lösung in 150 Volumteile Eiswasser gegossen und der entstandene Niederschlag nach 30 Minuten abgesaugt,
in Wasser gewaschen und im Vakuum über Calciumehlorid getrocknet. Aus dem Rohprodukt (0;51 Gewichtsteil) ge winnt man durch Kristallisation aus Äther 0,3 Gewichtsteile d5 - 3ss,lsss,21- Triacetoxy- pregnen-17a-ol-20-on vom F. = 181-183 ; [cu]D = -24 (in Chloroform). Die Verbin- dung- zeigt im Ultraviolettspektrum bei 295 mu ein deutliches Maximum (a = 80).
Process for the production of 16ss-acyloxy-17a-oxy-20-oxo-pregnanes The invention relates to a process for the production of saturated or unsaturated 16f3-acyloxy-17a-oxy-20-oxo-pregnaues, which are in the 3-position a free or protected oxy or oxo group,
in the 21-position have a free or protected oxy group and, in addition, optionally have further substituents, which is characterized in that it is split into the corresponding 16,17-oxido compounds by treatment with aliphatic carboxylic acids.
In addition to a free oxy or oxo group, the compounds in the 3-position can, for. B. contain an esterified oxy group or a ketalized oxo group. Furthermore, other substituents can also be present, for. B. an oxy or oxo group in the 11-position and double bonds z. B. starting from carbon atom 5.
The compounds obtainable according to the invention are particularly valuable because they have interesting pharmacological properties. In particular, the 17a-oxy-16ss-acet-oxy-deoxycorticosterone acetate has a pronounced adrenal cortical hormone effect, which in the type of effect differs from that of the z. B. deviates from 17 rOxy-deoxycorticosterone and sometimes exceeds it.
Aliphatic carboxylic acids with at least 2 carbon atoms are preferably used to split the oxide ring, i.e. Acetic acid and higher. If necessary, who also uses catalysts for the cleavage. The addition of conc. Sulfuric acid axis.
If the starting materials are new, they can be obtained using known methods. If the process products are intermediate products, they can be converted into physiologically active compounds by methods known per se, preferably those which have the d4-3 grouping,
- convert. In particular, an acyloxy group in the 3-position can be hydrolyzed by the gentle action of alkaline or acidic agents, for example hydrogen carbonate solution or dilute mineral acid. In compounds obtained with a free 3-hydroxyl group, the latter can be converted into an oxo group in a manner known per se by dehydrogenating agents. For this purpose z. B.
Chromic acid in glacial acetic acid, chromium (VI) salts in an acidic medium, chromium trioxide pyridine complex, permangnate, metal alcoholates or phenolates in the presence of ketones, N-bromacetamide, for example in dioxane water or pyridine -t-butanol, hypohalites, heating with metals or metal oxides such as copper oxide, etc.
A double bond in the 5; 6 position can be temporarily protected by the addition of halogen or hydrogen halide or by conversion into i- # steroids. Finally, in reaction products saturated in ring A with a free 3-0_xo group in a-position to the same, a double bond can be introduced in a known manner.
For this purpose, brominating is advantageously carried out, reacted with a hydrazide, such as semicarbazide, and the hydrazone is cleaved by means of a carbonyl compound, such as pyruvic acid.
<I> Example 1 </I> 9 parts by weight d4 - 21- acetoxy -16.17a - oxido-pregnen-3.20 dione from F.
= 165-167 (prepared in a manner known per se from d4.16-21-acetoxy-pregnadiene-3.20-dione) are left to stand in 180 parts by volume of glacial acetic acid and 25 parts by volume of concentrated sulfuric acid at +10 for 10 hours. The Lief red, fluorescent reaction solution is then poured into 2000 parts by volume of water and extracted several times with ether.
The united th ether solutions are washed with water, dilute sodium bicarbonate solution and water, dried and evaporated. 10 parts by weight of a yellow oil are obtained, which are dissolved in 100 parts by volume of benzene and chromatographed on a column of 250 parts by weight of aluminum oxide. Eluting with benzene recovers about 3 parts by weight of starting material.
With a mixture of equal parts by volume of benzene and ether, 3.5 parts by weight of a colorless oil are eluted, from which the pure d4-16ss, 21-D.ifacetoxy-pregnen, 17, a-ol-3.20- is obtained by crystallization from ether. dion vom F. = 167-168 wins. It shows a strong absorption maximum at 241 mu (a <I> = </I> 17000) and the spec. Rotation [a] <I> D = </I> + 99 (in Chloroforih).
The acetyl groups can be soaped off as follows: 2.6 parts by weight of the acetoxy compound are dissolved in 6 parts by volume of methanol and a methylate solution of 0.3 parts by weight of sodium and 22 parts by volume of methanol is added.
After 3 minutes, 10 parts by volume of a mixture of equal parts by volume of water and methanol are added and, after a further 3 minutes, the mixture is acidified with 1 part by volume of glacial acetic acid. The reaction mixture is then concentrated to a small volume in vacuo, ver with 200 parts by volume of water and extracted with chloroform.
From the chloroform extract, washed with water, sodium bicarbonate solution and water and dried, 1.86 parts by weight of a crystallizate are obtained after evaporation of the solvent and the addition of acetone. The triol of F. = 208-212 is obtained by recrystallization from acetone and from isopropyl ether.
<I> Example 2 </I> 0.5 part by weight d5 - 3ss, 21-diacetox-y-16,17a-oxido-pregnen-20-one (in a manner known per se from the 4th s, 16-3ss , 21-diacetoxy-pregnaäien-20-one produced) by F.
= 170 to 173 are dissolved in 10 parts by volume of glacial acetic acid, with one part by volume of a hybrid of 10 parts by volume of glacial acetic acid and 2.5 parts by volume of conc. Sulfuric acid was added and left to stand tightly closed for 9 hours at room temperature. Then the brown-red solution is poured into 150 parts by volume of ice water and the resulting precipitate is suctioned off after 30 minutes,
washed in water and dried in vacuo over calcium chloride. 0.3 parts by weight of d5-3ss, lsss, 21-triacetoxy-pregnen-17a-ol-20-one with a melting point of 181-183 are obtained from the crude product (0.51 part by weight) by crystallization from ether; [cu] D = -24 (in chloroform). The compound shows a clear maximum in the ultraviolet spectrum at 295 μm (a = 80).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH332324T | 1953-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH332324A true CH332324A (en) | 1958-08-31 |
Family
ID=4502387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH332324D CH332324A (en) | 1953-09-17 | 1953-09-17 | Process for the preparation of 16B-acyloxy-17a-oxy-20-oxo-pregnanes |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH332324A (en) |
-
1953
- 1953-09-17 CH CH332324D patent/CH332324A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1468035A1 (en) | Process for the preparation of 19-alkyl steroids | |
| CH332324A (en) | Process for the preparation of 16B-acyloxy-17a-oxy-20-oxo-pregnanes | |
| DE1027663B (en) | Process for the preparation of 11-oxy- or 11-acyloxysteroids unsubstituted in the 12-position | |
| DE960200C (en) | Process for the preparation of 4-pregnen-16 ª ‡ -ol-3, 20-diones | |
| DE2140291C3 (en) | Process for the preparation of pregnane derivatives | |
| DE935969C (en) | Process for the production of ª ‡, ª ‰ -unsaturated steroid ketones | |
| DE1131213B (en) | Process for the production of new pregnane compounds | |
| DE1518907C3 (en) | Process for the preparation of delta high 14 -3,20-diketo-21-acyloxysteriodes | |
| DE962434C (en) | Process for making compounds of the steroid series | |
| AT206593B (en) | Process for the preparation of 6-methyl-3-oxo-Δ <4> -steroids | |
| DE870102C (en) | Process for the preparation of 17, 20-oxyketones of the Pregnan series | |
| DE956954C (en) | Process for the preparation of pregnane-16-01-3, 20-dione unsaturated in the 4-position | |
| AT271759B (en) | Process for the production of new 1,2β-methylene steroids | |
| DE1003729B (en) | Process for the preparation of í¸-3-oxo-16ª ‰ -acetoxy-17ª ‡ -ol-20-ketopregnenes | |
| DE1593337C (en) | Process for the preparation of 3 Oxo 7 alpha methyl gona 4.9 are used | |
| DE1793676C2 (en) | Process for the production of Delta 4 or. Delta 5-unsaturated steroids of the androstane, pregnan and sapogenin series with a carboxyl group in the 19 position | |
| CH322805A (en) | Process for the preparation of 20-oxo-21-acetoxy-pregnanes | |
| DE957482C (en) | Process for the preparation of esters of 11-oxy derivatives of the pregnan, androstan and test series | |
| CH322482A (en) | Process for the preparation of 16a-oxy-20-oxo-pregnanes | |
| DE1094258B (en) | Process for the preparation of fluorinated 16-methyl steroids | |
| DE1078572B (en) | Process for the production of new allosteroids | |
| DE1193041B (en) | Process for making delta 7, delta 7.9, (11), delta 7.9, (11), 16, delta 7, delta 8 or delta 8.16 steroids | |
| CH407108A (en) | Process for the preparation of 5-19-hydroxy steroids | |
| DE1007327B (en) | Process for making compounds of the steroid series | |
| DE1021367B (en) | Process for the production of new halogen pregnenes |