CH321333A - Process for the preparation of 11-oxo derivatives of testosterone - Google Patents
Process for the preparation of 11-oxo derivatives of testosteroneInfo
- Publication number
- CH321333A CH321333A CH321333DA CH321333A CH 321333 A CH321333 A CH 321333A CH 321333D A CH321333D A CH 321333DA CH 321333 A CH321333 A CH 321333A
- Authority
- CH
- Switzerland
- Prior art keywords
- testosterone
- preparation
- acid
- ester
- keto
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testosterone Natural products O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 title claims description 6
- 229960003604 testosterone Drugs 0.000 title claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- WTPMRQZHJLJSBO-XQALERBDSA-N 11-oxotestosterone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 WTPMRQZHJLJSBO-XQALERBDSA-N 0.000 claims description 5
- 229960000583 acetic acid Drugs 0.000 claims description 5
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 5
- 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 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound 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 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000001548 androgenic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- -1 11-keto-testosterone ester Chemical class 0.000 description 1
- YQDZGFAYWGWSJK-SLMGBJJTSA-N 11beta-hydroxytestosterone Chemical class O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 YQDZGFAYWGWSJK-SLMGBJJTSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 1
- LCOMQMDZABGLTI-YUWMHKDHSA-N [(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-3,11-dioxo-2,6,7,8,9,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2=O LCOMQMDZABGLTI-YUWMHKDHSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960001712 testosterone propionate Drugs 0.000 description 1
- 150000003515 testosterones Chemical class 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)
- Steroid Compounds (AREA)
Description
Procédé de préparation de dérivés 11-oxo de la testostérone On a déjà utilisé la testostérone et divers dérivés de la testostérone pour leur activité testiculoïde. Parmi les dérivés habituellement utilisés se trouvent par exemple le propionate de testdstérone et la 17-méthyl-testostérone. En plus de l'activité testiculoïde, ces substances androgènes présentent fréquemment d'autres effets qui peuvent être indésirables.
Ainsi, 17-méthyl-testostérone, et dans certains cas le propionate de testostérone, ont pour effet de provoquer de l'oedème ou un arrêt du coeur. Le but de l'invention est la préparation de substances androgènes très utiles ne possédant ces propriétés indésirables qu'à un degré moins élevé.
Les composés à la préparation desquels se rapporte la présente invention sont des solides cristallins blancs, assez solubles dans les sol vants organiques habituels, et relativement in solubles dans l'eau.
Le procédé selon la présente invention, pour la préparation de dérivés 11-oxo de la testostérone, est caractérisé en ce qu'on oxyde un 17-ester de a4-androstène-3-one-11(i,17(3- diol en solution acide au moyen d'acide chro- mique, de façon à obtenir un ester de 11-céto- testostérone.
Cet ester répond à la formule générale suivante
EMI0001.0021
dans laquelle R représente un reste d'acide, notamment d'acide gras inférieur ou d'acide benzoïque.
La préparation des esters de la 11-hydroxy- testostérone utilisés comme matières de départ dans le procédé de la présente invention est décrite dans le brevet No 319781.
Pour la mise en oeuvre du procédé suivant l'invention, le 17-acétate de 04-androstène-3- one-11(3,17[3-diol est le produit de départ pré féré. Cependant, on peut utiliser d'autres esters de ce composé tels que le propionate, le buty- rate, le benzoate et analogues.
Les esters résultant de l'oxydation peuvent être soumis à une hydrolyse en milieu alcalin aqueux, en vue d'obtenir la 11-céto-testosté- rone. Le milieu alcalin aqueux peut être une solution aqueuse d'hydroxyde, de carbonate ou de bicarbonate alcalin ou alcalino-terreux ou de matières analogues. L'oxydation a lieu de préférence à une température d'environ 10-100(l C. On réalise de préférence l'oxydation en présence d'acide acétique glacial.
Comme agent oxydant on uti lise l'acide chromique, ajouté comme tel ou sous forme d'anhydride chromique additionné d'eau, en formant ainsi l'acide chromique in/situ. La réaction est ordinairement achevée aux températures indiquées ci-dessus en une demi à 3 ou à 4 heures.
Après achèvement de la réaction on peut isoler le produit en ajoutant une solution aqueuse d'un alcool au mélange réactionnel, ce qui provoque la préci pitation de l'ester de 11-céto-testostérone. On purifie ensuite le produit par recristallisation dans un solvant organique ou un mélange de solvants organiques tels que le mélange acétone- éther de pétrole, puis on peut l'hydrolyser pour obtenir la 11-céto-testostérone.
L'exemple suivant illustre l'invention. <I>Exemple</I> Le produit de départ est préparé comme suit: on chauffe au bain-marie pendant 20 minutes une solution de 156 mg de 3 -benzyloxy-A3#5- androstadiène-11(i -17[i -diol dans 8 em3 d'acide acétique aqueux à 50 %, on la refroidit, on la verse dans une solution saturée de bicarbonate de sodium,
on la re- largue et on l'extrait par l'acétate d'éthyle. On lave l'extrait avec une solution saline saturée et à l'eau. On le sèche sur du sulfate de magné sium, on le filtre sur de la terre de diatomées et on l'évapore sous pression réduite pour obtenir un solide cristallin blanc.
La recristal- lisation dans un mélange d'acétone, d'éther de pétrole (64-66o C) et d'éther donne 82 mg de A4-androstène-11p;17(3-diol-3-one (11(3-hy- droxy-testostérone), point de fusion: 235 236,5o C ; e.42=14900 (alcool absolu), [ct] 30 = --I-136 (chloroforme). On traité 300 mg de A4-androstène-1 l (3,17p-diol-3-one ainsi obtenue dans 3 cm' de pyridine par 3 cm3 d'anhydride acétique.
On laisse le mélange reposer à la température ambiante pendant 24 heures, puis on le verse dans l'eau glacée. On extrait le produit par l'acétate d'éthyle. L'évaporation sous pression réduite donne une huile qui cris- tallise au repos et par frottement. Le résidu (environ 330 mg) consiste en 17-acétate de A4-androstène-11[3,17(3-diol-3-one brut.
L'oxydation de l'acétate ainsi préparé est effectuée comme suit<B>:</B> on dissout l'acétate dans 5 cm3 d'acide acétique glacial et on traite la solution refroidie par 180 mg d'anhydride chromique additionnés de trois gouttes d'eau (acide chromique) dans 5 cm3 d'acide acétique glacial. On laisse le mélange reposer à la tem pérature ambiante (24o C) pendant 1 heure 45. L'addition d'eau contenant quelques gouttes dé méthanol donne des cristaux que l'on re cueille.
La recristallisation dans un mélange d'acétone et d'éther de pétrole donne 98 mg d'acétate de A4-androstène-3,11-dione; 17[3-ol (17-acétate de 11-céto-testostérône), point de fusion: 166,5-167,5 C lmax;m,im = 237-238 m#t (dans l'alcool absolu) ;
[ ]'24 n = -173 (chloro- forme. A partir des liqueurs-mères on obtient encore 31 mg de produit moins pur, point de fusion : 164,5-1660 C.
Process for the preparation of 11-oxo derivatives of testosterone Testosterone and various derivatives of testosterone have already been used for their testiculoid activity. Among the derivatives usually used are, for example, testdsterone propionate and 17-methyl-testosterone. In addition to testiculoid activity, these androgenic substances frequently exhibit other effects which may be undesirable.
Thus, 17-methyl-testosterone, and in some cases testosterone propionate, have the effect of causing edema or heart failure. The object of the invention is the preparation of very useful androgenic substances possessing these undesirable properties only to a lesser degree.
The compounds to the preparation of which the present invention relates are white crystalline solids, fairly soluble in the usual organic solvents, and relatively insoluble in water.
The process according to the present invention, for the preparation of 11-oxo derivatives of testosterone, is characterized in that a 17-ester of a4-androstene-3-one-11 (i, 17 (3-diol in acidic solution by means of chromic acid, so as to obtain an ester of 11-keto-testosterone.
This ester corresponds to the following general formula
EMI0001.0021
in which R represents an acid residue, in particular a lower fatty acid or benzoic acid.
The preparation of the 11-hydroxy-testosterone esters used as starting materials in the process of the present invention is described in Patent No. 319781.
For carrying out the process according to the invention, 04-androstene-3-one-11 17-acetate (3,17 [3-diol is the preferred starting material. However, other products can be used. esters of this compound such as propionate, butyrate, benzoate and the like.
The esters resulting from the oxidation can be subjected to hydrolysis in an aqueous alkaline medium, in order to obtain 11-keto-testosterone. The aqueous alkaline medium may be an aqueous solution of alkali or alkaline earth hydroxide, carbonate or bicarbonate or the like. The oxidation preferably takes place at a temperature of about 10-100 (1 ° C. The oxidation is preferably carried out in the presence of glacial acetic acid.
As an oxidizing agent, chromic acid is used, added as such or in the form of chromic anhydride with the addition of water, thus forming chromic acid in situ. The reaction is ordinarily completed at the temperatures indicated above in one-half to 3 or 4 hours.
After completion of the reaction, the product can be isolated by adding an aqueous solution of an alcohol to the reaction mixture, which causes precipitation of the 11-keto-testosterone ester. The product is then purified by recrystallization from an organic solvent or a mixture of organic solvents such as acetone-petroleum ether, and then it can be hydrolyzed to obtain 11-keto-testosterone.
The following example illustrates the invention. <I> Example </I> The starting product is prepared as follows: a solution of 156 mg of 3 -benzyloxy-A3 # 5- androstadiene-11 (i -17 [i - diol in 8 em3 of 50% aqueous acetic acid, cooled, poured into saturated sodium bicarbonate solution,
it is released and extracted with ethyl acetate. The extract is washed with saturated saline solution and water. It is dried over magnesium sulfate, filtered through diatomaceous earth and evaporated under reduced pressure to obtain a white crystalline solid.
Recrystallization from a mixture of acetone, petroleum ether (64-66o C) and ether gives 82 mg of A4-androstene-11p; 17 (3-diol-3-one (11 (3- hy- droxy-testosterone), melting point: 235 236.5o C; e.42 = 14900 (absolute alcohol), [ct] 30 = --I-136 (chloroform) 300 mg of A4-androstene are treated. 1 l (3,17p-diol-3-one thus obtained in 3 cm 3 of pyridine per 3 cm 3 of acetic anhydride.
The mixture is allowed to stand at room temperature for 24 hours, then poured into ice water. The product is extracted with ethyl acetate. Evaporation under reduced pressure gives an oil which crystallizes on standing and on friction. The residue (approximately 330 mg) consists of crude A4-androstene-11 [3,17 (3-diol-3-one) 17-acetate.
The oxidation of the acetate thus prepared is carried out as follows <B>: </B> the acetate is dissolved in 5 cm3 of glacial acetic acid and the cooled solution is treated with 180 mg of chromic anhydride added to three drops of water (chromic acid) in 5 cm3 of glacial acetic acid. The mixture is left to stand at room temperature (24 ° C.) for 1 hour 45 minutes. The addition of water containing a few drops of methanol gives crystals which are collected.
Recrystallization from a mixture of acetone and petroleum ether gives 98 mg of A4-androstene-3,11-dione acetate; 17 [3-ol (11-keto-testosterone 17-acetate), melting point: 166.5-167.5 C lmax; m, im = 237-238 m # t (in absolute alcohol);
[] 24 n = -173 (chloroform. From the mother liquors a further 31 mg of less pure product is obtained, melting point: 164.5-1660 C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US321333XA | 1952-12-06 | 1952-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH321333A true CH321333A (en) | 1957-04-30 |
Family
ID=21863277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH321333D CH321333A (en) | 1952-12-06 | 1953-12-05 | Process for the preparation of 11-oxo derivatives of testosterone |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH321333A (en) |
-
1953
- 1953-12-05 CH CH321333D patent/CH321333A/en unknown
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