CH206111A - Process for the preparation of a new ester of oestron. - Google Patents
Process for the preparation of a new ester of oestron.Info
- Publication number
- CH206111A CH206111A CH206111DA CH206111A CH 206111 A CH206111 A CH 206111A CH 206111D A CH206111D A CH 206111DA CH 206111 A CH206111 A CH 206111A
- Authority
- CH
- Switzerland
- Prior art keywords
- oestrone
- preparation
- agent
- new ester
- oestron
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 title claims description 7
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229960003399 estrone Drugs 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- FLJFMDYYNMNASJ-UHFFFAOYSA-N 6-methyl-5,6-dihydrothieno[2,3-b]thiopyran-4-one Chemical compound S1C(C)CC(=O)C2=C1SC=C2 FLJFMDYYNMNASJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000002253 acid Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010792 warming 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines neuen Esters des Oestrons. Es wurde gefunden, dass man zu einem neuen Ester des Oestrons gelangen kann, wenn man Oestron mit einem n-Caprylylie- rungsmittel umsetzt.
Als geeignete n-Caprylylierungsmittel kommen z. B. n-Caprylsäure-anhydrid, -halo- genide, -ester oder die Säure selbst in Frage.
Das so erhaltene Oestron-n-caprylat bildet Kristalle vom F. 70-710. Es soll thera peutische Verwendung finden.
Beispiel: 1 Teil Oestron wird in 4 Teilen Pyridin gelöst, mit 1 Teil n-Caprylsäurechlorid ver setzt und bei Zimmertemperatur einige Zeit stehen gelassen. Nach kurzem Erwärmen und Erkaltenlassen wird angesäuert, mit Wasser verdünnt und das Reaktionsprodukt mit Äther ausgezogen.
Die mit Wasser, verdünnter Säure, Sodalösung und wiederum mit Wasser gewaschene ätherische Lösung wird getrock net und vom Lösungsmittel befreit, den Rück stand kristallisiert man aus Hexan oder ver- dünntem Alkohol um und erhält so das Oestron-n-caprylat vom F. 70-710 Die Reaktion kann auch in Anwesenheit anderer tertiärer Basen oder selbst ohne solche durchgeführt werden.
Process for the preparation of a new ester of oestron. It has been found that a new ester of oestrone can be obtained if oestrone is reacted with an n-caprylylating agent.
Suitable n-caprylylating agents are e.g. B. n-caprylic anhydride, halides, esters or the acid itself.
The oestrone-n-caprylate obtained in this way forms crystals of F. 70-710. It should be used therapeutically.
Example: 1 part of oestrone is dissolved in 4 parts of pyridine, 1 part of n-caprylic acid chloride is added and left to stand for some time at room temperature. After briefly warming up and letting it cool down, it is acidified, diluted with water and the reaction product extracted with ether.
The ethereal solution washed with water, dilute acid, soda solution and again with water is dried and freed from the solvent, the residue is recrystallized from hexane or dilute alcohol and the oestrone-n-caprylate of F. 70- 710 The reaction can also be carried out in the presence of other tertiary bases or even without them.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH206111T | 1936-07-30 | ||
| CH201115T | 1936-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH206111A true CH206111A (en) | 1939-07-15 |
Family
ID=25723669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH206111D CH206111A (en) | 1936-07-30 | 1936-07-30 | Process for the preparation of a new ester of oestron. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH206111A (en) |
-
1936
- 1936-07-30 CH CH206111D patent/CH206111A/en unknown
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