CH210720A - Method for representing a connection of the adrenal cortex hormone series. - Google Patents
Method for representing a connection of the adrenal cortex hormone series.Info
- Publication number
- CH210720A CH210720A CH210720DA CH210720A CH 210720 A CH210720 A CH 210720A CH 210720D A CH210720D A CH 210720DA CH 210720 A CH210720 A CH 210720A
- Authority
- CH
- Switzerland
- Prior art keywords
- agent
- carried out
- palmitylation
- adrenal cortex
- connection
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 239000003470 adrenal cortex hormone Substances 0.000 title claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 claims description 4
- 229940119740 deoxycorticosterone Drugs 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 3
- 235000021314 Palmitic acid Nutrition 0.000 claims 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 2
- -1 palmityl halide Chemical class 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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 einer Verbindung der Nebennierenrindenhormonreihe. Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung einer Verbindung der Nebennierenrindenhormon- reihe, das dadurch gekennzeichnet ist, dass man Desoxycorticosteron mit einem palmity- lierenden Mittel behandelt.
Die auf diese Weise gewonnene Verbin dung hat die Formel C2:,HlC3-CO . C15H. und besitzt die Struktur:
EMI0001.0009
Diese Verbindung bildet farblose Kri stalle. die bei 60 bis 61 schmelzen; sie lässt sich aus Petroläther umkristallisieren.
Zur Palmitylierung eignen sich die be- kannten Veresterungsmethoden. Nur solche Methoden, bei denen stark alkalische Reagen- tien (wie freie Alkalien) benötigt werden, sind entweder mit grosser Vorsicht zu be nutzen oder ganz auszuschliessen. Bei Ver wendung von Methoden, bei denen freie Mi neralsäure (z.
B. Chlorwasserstoffsäure) auf tritt, arbeitet man zweckmässig mit säure bindenden Mitteln (tertiäre Basen, Kalium- earbonat etc.). Auch durch Umesterung kann das Desoxycorticosteronpalmitat dargestellt werden. Gegebenenfalls arbeitet man in Ge genwart von Verdünnungsmitteln, wie Äther, Benzol, Aceton usw.
Die neue Verbindung soll therapeutische Verwendung finden oder als Zwischenpro dukt zur Herstellung von therapeutischen wertvollen Verbindungen dienen. <I>Beispiel:</I> Zu einer mit Kältemischung gekühlten Lösung von 0,5 Teilen Desoxycorticosteron und 5 Teilen Pyridin wird 1 Teil Palmitin- Säurechlorid zugetropft und das Gemisch während mehreren Stunden bei Raumtem peratur stehen gelassen.
Nach Versetzen mit Wasser wird das Reaktionsprodukt in 3ther aufgenommen. Man schüttelt die Xtherlösung nacheinander mit verdünnter Salzsäure, ver dünnter Sodalösung, verdünnter Natronlauge und Wasser und trocknet sie über Natrium sulfat. Das durch Verdampfen des Lösungs mittels gewonnene Palmitat des Desoxy - eorticosterons wird aus Petroläther umkristal lisiert und zeigt hierauf einen F. von 60 bis 61 und eine spezifische Drehung von Via] D -f- 128 (in Chloroform).
Method for representing a connection of the adrenal cortex hormone series. The subject of the present patent is a process for the production of a compound of the adrenal cortex hormone series, which is characterized in that deoxycorticosterone is treated with a palmitylating agent.
The compound obtained in this way has the formula C2:, HIC3-CO. C15H. and has the structure:
EMI0001.0009
This compound forms colorless crystals. those melting at 60 to 61; it can be recrystallized from petroleum ether.
The known esterification methods are suitable for palmitylation. Only those methods which require strongly alkaline reagents (such as free alkalis) should either be used with great caution or excluded entirely. When using methods in which free mineral acid (e.g.
B. hydrochloric acid) occurs, it is advisable to work with acid-binding agents (tertiary bases, potassium carbonate, etc.). Deoxycorticosterone palmitate can also be produced by transesterification. If necessary, one works in the presence of diluents such as ether, benzene, acetone, etc.
The new compound is intended to find therapeutic use or serve as an intermediate product for the preparation of therapeutically valuable compounds. <I> Example: </I> 1 part of palmitic acid chloride is added dropwise to a solution of 0.5 part of deoxycorticosterone and 5 parts of pyridine, cooled with a cold mixture, and the mixture is left to stand for several hours at room temperature.
After adding water, the reaction product is taken up in 3ther. The Xtherlösung is shaken successively with dilute hydrochloric acid, dilute soda solution, dilute sodium hydroxide solution and water and dried over sodium sulfate. The deoxy-eorticosterone palmitate obtained by evaporation of the solution is recrystallized from petroleum ether and shows an F. of 60 to 61 and a specific rotation of Via] D -f- 128 (in chloroform).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH204234T | 1936-12-23 | ||
| CH210720T | 1936-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210720A true CH210720A (en) | 1940-07-31 |
Family
ID=25724014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210720D CH210720A (en) | 1936-12-23 | 1936-12-23 | Method for representing a connection of the adrenal cortex hormone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210720A (en) |
-
1936
- 1936-12-23 CH CH210720D patent/CH210720A/en unknown
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