CH210714A - Process for the preparation of a corticosterone ester. - Google Patents
Process for the preparation of a corticosterone ester.Info
- Publication number
- CH210714A CH210714A CH210714DA CH210714A CH 210714 A CH210714 A CH 210714A CH 210714D A CH210714D A CH 210714DA CH 210714 A CH210714 A CH 210714A
- Authority
- CH
- Switzerland
- Prior art keywords
- corticosterone
- ester
- palmitylation
- rendes
- agent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 title claims description 11
- -1 corticosterone ester Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000013081 microcrystal Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- NGEZPLCPKXKLQQ-VOTSOKGWSA-N (e)-4-(3-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=CC(\C=C\C(C)=O)=C1 NGEZPLCPKXKLQQ-VOTSOKGWSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000000926 separation method 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Corticosteronesters. Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung eines Corticosteronesters, das dadurch gekennzeich net ist, dass man Corticosteron mit palmity- lierenden Mitteln behandelt.
Die auf diese Weise gewonnene Verbin dung besitzt die Formel C2182904 # <B>CO -</B> C1G11I31 und die folgende Struktur:
EMI0001.0011
Sie bildet Mikrokristalle, die bei etwa 90 schmelzen, und ist von fettartiger Beschaf fenheit. Sie lässt sich aus Petroläther oder wenig Äther-Petroläther umkristallisieren.
Zur Palmitylierung eignen sich die be kannten Veresterungsmethoden. Nur solche Methoden, bei denen stark alkalische Rea- gentien (wie freie Alkalien) benötigt werden, sind entweder mit grosser Vorsicht zu be nutzen oder ganz auszuschliessen.
Methoden, bei denen freie Mineralsäure (wie Chlor wasserstoff) auftritt, können bei vorsich tigem Arbeiten benutzt werden, zweckmässig ist jedoch in diesen Fällen unter Zusatz von säurebindenden Mitteln (wie. Pyridin, ga- liumcarbonat, etc.) zu arbeiten. Auch durch LTmesterung kann das Corticosteronpalmitat gewonnen werden. Gegebenenfalls arbeitet man in Gegenwart von Verdünnungsmitteln wie Äther, Benzol, Aceton usw.
Der neue Ester des Corticosterons soll therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung oder zur Reinigung von therapeutisch wertvollen Ver bindungen dienen.
<I>Beispiel:</I> 20 mg Corticosteron werden in 80 mg Pyridin gelöst, mit der Lösung von 25 mg Palmitinsäurechlorid in 0,5 cm3 trockenem Äther versetzt und ohne Beachtung der Aus scheidung von Kristallen bei gelinder ZVärme zur Trockne gedampft. Der Rückstand wird mit etwas Wasser versetzt und mit Äther in einen Scheidetrichter gespült. Er wird mehrere Male mit verdünnter Salzsäure, dann mit Wasser gewaschen.
Die getrocknete Ätherlösung wird durch Destillation von Äther befreit und der Rückstand mit Pen- tan angerieben. Der bald gallertig ausfal lende Palmitinsäureester des Corticosterons wird abgenutscht und mehrmals mit Pentan gewaschen.
Er lässt sich aus Petroläther oder wenig Äther-Petroläther durch Ein engen umkristallisieren. Er behält. dabei eine etwas fettartige Konsistenz und ist nur mikrokristallin. Der Schmelzpunkt liegt bei etwa 90 C. Der Ester ist leicht fettlöslich und unlöslich in Wasser.
Process for the preparation of a corticosterone ester. The subject of the present patent forms a process for the production of a corticosterone ester which is characterized in that corticosterone is treated with palmitylating agents.
The compound obtained in this way has the formula C2182904 # <B> CO - </B> C1G11I31 and the following structure:
EMI0001.0011
It forms microcrystals that melt at about 90 and is fatty in nature. It can be recrystallized from petroleum ether or a little ether-petroleum ether.
The known esterification methods are suitable for palmitylation. Only those methods that require strongly alkaline reagents (such as free alkalis) are either to be used with great caution or to be excluded entirely.
Methods in which free mineral acid (such as hydrogen chloride) occurs can be used when working carefully, but in these cases it is advisable to work with the addition of acid-binding agents (such as pyridine, gallium carbonate, etc.). Corticosterone palmitate can also be obtained by esterification. You may work in the presence of diluents such as ether, benzene, acetone, etc.
The new ester of corticosterone should be used therapeutically or serve as an intermediate for the production or purification of therapeutically valuable compounds.
<I> Example: </I> 20 mg of corticosterone are dissolved in 80 mg of pyridine, mixed with a solution of 25 mg of palmitic acid chloride in 0.5 cm3 of dry ether and, without considering the separation of crystals, evaporated to dryness with mild warmth. The residue is mixed with a little water and rinsed with ether into a separating funnel. It is washed several times with dilute hydrochloric acid and then with water.
The dried ether solution is freed from ether by distillation and the residue is rubbed with pentane. The palmitic acid ester of corticosterone, which soon becomes gelatinous, is sucked off and washed several times with pentane.
It can be recrystallized from petroleum ether or a little ether-petroleum ether by narrowing it. He keeps. it has a somewhat greasy consistency and is only microcrystalline. The melting point is around 90 C. The ester is easily soluble in fat and insoluble in water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH210714T | 1936-12-23 | ||
| CH204233T | 1936-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210714A true CH210714A (en) | 1940-07-31 |
Family
ID=25724008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210714D CH210714A (en) | 1936-12-23 | 1936-12-23 | Process for the preparation of a corticosterone ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210714A (en) |
-
1936
- 1936-12-23 CH CH210714D patent/CH210714A/en unknown
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