CH205437A - Process for the preparation of a new ester of estradiol. - Google Patents
Process for the preparation of a new ester of estradiol.Info
- Publication number
- CH205437A CH205437A CH205437DA CH205437A CH 205437 A CH205437 A CH 205437A CH 205437D A CH205437D A CH 205437DA CH 205437 A CH205437 A CH 205437A
- Authority
- CH
- Switzerland
- Prior art keywords
- estradiol
- valerianylating
- agent
- preparation
- new ester
- Prior art date
Links
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 title claims description 10
- 229960005309 estradiol Drugs 0.000 title claims description 10
- 229930182833 estradiol Natural products 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- -1 n-valeric acid halide Chemical class 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines neuen Esters des Oestradiols. Es wurde gefunden, dass man zu einem neuen Ester des Östradiols gelangen kann, wenn man 1 Mol Ostradiol mit 2 Mol eines n-Valerianylierungsmittels umsetzt.
Als Valerianylierungsmittel verwendet man z. B. n-Valeriansäureanhydrid, -haloge- nide, -ester oder die Säure selbst. Zweck mässig wird die Reaktion in Gegenwart von Lösungsmitteln, wie z. B. tertiären Basen, wie Pyridin, Chinolin oder auch aromatischen Kohlenwasserstoffen durcbgeführt.
Das so erhaltene Östradiol-di-n-valerianat bildet ein gelbliches Öl vom Siedepunkt 0,05 mm<B>220-2300</B> (Badtemperatur). Es soll therapeutische Verwendung finden.
<I>Beispiel:</I> 2,3 Teile Östradiol werden mit 12 Teilen Pyridin und 1O Teilen n-Valeriansäurearihy- drid einige Zeit im Ölbad auf<B>1150</B> erwärmt. Die erkaltete Lösung wird mit 250 Teilen Wasser versetzt, wodurch sich ein Öl aus scheidet, das mit Äther aufgenommen wird. Die abgetrennte ätherische Lösung wird . nacheinander mit
EMI0001.0023
Schwefelsäure, Wasser,
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Sodalösung und Wasser gewaschen und hierauf getrocknet. Das Lösungsmittel wird entfernt und der Rückstand durch Hoch vakuumdestillation gereinigt.
Das Östradiol- di-n-valerianat bildet ein gelbliches 0I vom Siedepunkt 0,05 mm 220-230' (Badtempe- ratur).
Die Reaktion kann auch in Anwesenheit anderer tertiärer Basen, wie z. B. Dimethyl- anifin, Chinolin und dergl. oder auch ohne solche Basen durchgeführt werden.
Process for the preparation of a new ester of estradiol. It has been found that a new ester of estradiol can be obtained if 1 mole of estradiol is reacted with 2 moles of an n-valerianylating agent.
The valerianylating agent used is, for. B. n-valeric anhydride, halides, esters or the acid itself. Appropriately, the reaction in the presence of solvents, such as. B. tertiary bases such as pyridine, quinoline or aromatic hydrocarbons.
The estradiol di-n-valerianate obtained in this way forms a yellowish oil with a boiling point of 0.05 mm 220-2300 (bath temperature). It should find therapeutic use.
<I> Example: </I> 2.3 parts of estradiol are heated with 12 parts of pyridine and 10 parts of n-valeric acid aryhydride in an oil bath to <B> 1150 </B> for some time. The cooled solution is mixed with 250 parts of water, whereby an oil separates out, which is absorbed with ether. The separated essential solution will. one after the other with
EMI0001.0023
Sulfuric acid, water,
EMI0001.0024
Washed soda solution and water and then dried. The solvent is removed and the residue is purified by high vacuum distillation.
The estradiol di-n-valerianate forms a yellowish oil with a boiling point of 0.05 mm 220-230 '(bath temperature).
The reaction can also be carried out in the presence of other tertiary bases, such as e.g. B. Dimethyl anifin, quinoline and the like. Or can be carried out without such bases.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH205437T | 1936-07-30 | ||
| CH201115T | 1936-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH205437A true CH205437A (en) | 1939-06-15 |
Family
ID=25723664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH205437D CH205437A (en) | 1936-07-30 | 1936-07-30 | Process for the preparation of a new ester of estradiol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH205437A (en) |
-
1936
- 1936-07-30 CH CH205437D patent/CH205437A/en unknown
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