CH201536A - Process for the preparation of a new ester. - Google Patents
Process for the preparation of a new ester.Info
- Publication number
- CH201536A CH201536A CH201536DA CH201536A CH 201536 A CH201536 A CH 201536A CH 201536D A CH201536D A CH 201536DA CH 201536 A CH201536 A CH 201536A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- water
- androstenol
- new
- ester
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound 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 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960003604 testosterone Drugs 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
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
Verfahren zur Darstellung eines neuen Esters. Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Darstellung eines neuen Esters, welches dadurch gekennzeich net ist, dass man 44,5-Androstenol-(17)-on-(3) mit einem Mol Phosphorogyhalogenid umsetzt und auf das Reaktionsprodukt Wasser ein wirken lässt.
Der so gewonnene 44,5 Androstenol-(17)- on-(3)-monophosphorsäureester der Formel
EMI0001.0010
hat den F.<B>150'.</B> Seine Alkalisalze, sowie auch sein Ammonium- und Triäthanolamin- salz sind in Wasser leicht löslich.
Die neue Verbindung soll therapeutische Verwendung finden. <I>Beispiel:</I> 1,0 g Testosteron werden in 10,0 cm' abso lutem Pyridin gelöst und 0,54 g frisch destil- liertes Phosphorogychlorid hinzugegeben, wo bei Erwärmung eintritt. Nach etwa 22stün- digem Stehen bei Zimmertemperatur wird das Reaktionsgemisch in Wasser gegossen.
Beim Ansäuern der Lösung mit verdünnter Salz säure scheidet sich der Testosteron-mono- phosphorsäureester vom F.<B>150'</B> aus. Er wird abfiltriert, mit Wasser gewaschen und im Vakuum getrocknet.
An Stelle von Phosphorogychlorid kann man zum Beispiel auch Phosphorogybromid verwenden.
Process for the preparation of a new ester. The subject of the present patent is a process for the preparation of a new ester, which is characterized in that 44,5-androstenol- (17) -one- (3) is reacted with one mole of phosphorogyhalide and water is allowed to act on the reaction product.
The 44.5 androstenol- (17) -on- (3) -monophosphoric acid ester of the formula obtained in this way
EMI0001.0010
has the F. <B> 150 '. </B> Its alkali salts, as well as its ammonium and triethanolamine salts, are easily soluble in water.
The new compound should find therapeutic use. <I> Example: </I> 1.0 g of testosterone are dissolved in 10.0 cm of absolute pyridine and 0.54 g of freshly distilled phosphorogychloride are added, which occurs when heated. After standing for about 22 hours at room temperature, the reaction mixture is poured into water.
When the solution is acidified with dilute hydrochloric acid, the testosterone monophosphoric acid ester is separated from the F. <B> 150 '</B>. It is filtered off, washed with water and dried in vacuo.
For example, phosphorogybromide can also be used instead of phosphorogychloride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH195775T | 1935-08-02 | ||
| CH201536T | 1935-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH201536A true CH201536A (en) | 1938-11-30 |
Family
ID=25722795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH201536D CH201536A (en) | 1935-08-02 | 1935-08-02 | Process for the preparation of a new ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH201536A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2928849A (en) * | 1953-11-20 | 1960-03-15 | Leo Ab | High-molecular weight derivatives of steroids containing hydroxyl groups and method of producing the same |
-
1935
- 1935-08-02 CH CH201536D patent/CH201536A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2928849A (en) * | 1953-11-20 | 1960-03-15 | Leo Ab | High-molecular weight derivatives of steroids containing hydroxyl groups and method of producing the same |
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