CH211255A - 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
- CH211255A CH211255A CH211255DA CH211255A CH 211255 A CH211255 A CH 211255A CH 211255D A CH211255D A CH 211255DA CH 211255 A CH211255 A CH 211255A
- Authority
- CH
- Switzerland
- Prior art keywords
- estradiol
- alkaline
- iso
- works
- dependent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 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 7
- 229930182833 estradiol Natural products 0.000 title claims description 7
- 229960005309 estradiol Drugs 0.000 title claims description 6
- 150000002148 esters Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 230000001419 dependent effect Effects 0.000 claims 3
- 150000001298 alcohols Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- CBMYJHIOYJEBSB-CAHXEBCQSA-N androstane-3,17-diol Chemical class C1C(O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)O)[C@@H]4[C@@H]3CCC21 CBMYJHIOYJEBSB-CAHXEBCQSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000005406 washing 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)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung eines neuen Esters des Oestradiols. Es wurde gefunden, dass man zu einem neuen Ester des Oestradiols gelangen kann, wenn man Oestradiol-di-iso-butyrat mit al kalisch reagierenden Mitteln in schonender Weise behandelt. Hierbei wird nur der Säurerest abgespalten, der an die phenolische Hydroxylgruppe gebunden ist. Als alkalisch reagierende Mittel können zum Beispiel Al kalihydroxyde, Alkalicarbonate, Erdalkali- hydroxyde, Magnesia usw. verwendet wer den.
Das so gewonnene Oestradiol-17-mono- iso-butyrat bildet Kristalle vom F. 183 bis <B>183,5'.</B> Es soll therapeutische Verwendung finden.
Während die partielle Verseifung von Biestern der Androstandiole zu Gemischen führt, die sich oft nur schwer trennen lassen, verläuft die Reaktion nach vorliegenden Ver fahren überraschenderweise durchaus ein heitlich und man erhält den Oestradiol-17- monoester in so gut wie quantitativer Aus beute.
<I>Beispiel:</I> 1 Teil Oestradiol-3,17-di-iso-butyrat (F. 100,5 bis 101,5 ; hergestellt zum Bei spiel durch Einwirkung von iso-Buttersäure- anhydrid auf eine Pyridinlösung von Oestra- diol) wird mit 100 Teilen einer Lösung von <B>0,5%</B> Natriumcarbonat in 95%igem Methyl alkohol versetzt, bei Zimmertemperatur ge löst und einige Zeit stehen gelassen.
Nach dem Ansäuern, Fällen mit Wasser, Abfil- trieren und gründlichem Waschen mit Was ser, verdünnter Sodalösung und Wasser wird das bereits -sehr reine Oestradiol-17-mono- iso-butyrat noch einige Male aus Methanol- Wasser umgelöst. Es schmilzt bei 183 bis <B>183,5-.</B>
An Stelle von Natriumcarbonat kann man auch andere alkalisch reagierende Mit tel, wie z. B. Alkalihydrogyde, Erdalkali- hydroxyde usw. verwenden. Die Reaktion kann auch in Gegenwart anderer Lösungs mittel, wie z. B. Äthylalkohol, iso-Butyl- alkohol, Aceton, Dioxan und dergleichen, gegebenenfalls in Gegenwart von Wasser, 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 estradiol di-iso-butyrate is treated gently with alkaline agents. Only the acid residue that is bound to the phenolic hydroxyl group is split off. Alkali metal hydroxides, alkali metal carbonates, alkaline earth metal hydroxides, magnesia, etc., for example, can be used as alkaline reacting agents.
The estradiol-17-mono-iso-butyrate obtained in this way forms crystals from F. 183 to <B> 183.5 '. </B> It is intended to be used therapeutically.
While the partial saponification of beasts of androstandiols leads to mixtures that are often difficult to separate, the reaction according to the present process surprisingly proceeds uniformly and the estradiol-17 monoester is obtained in virtually quantitative yield.
<I> Example: </I> 1 part oestradiol-3,17-di-iso-butyrate (F. 100.5 to 101.5; produced, for example, by the action of iso-butyric anhydride on a pyridine solution from Oestra - diol) is mixed with 100 parts of a solution of <B> 0.5% </B> sodium carbonate in 95% methyl alcohol, dissolved at room temperature and left to stand for some time.
After acidification, precipitation with water, filtering off and thorough washing with water, dilute soda solution and water, the already-very pure estradiol-17-mono-iso-butyrate is redissolved several times from methanol-water. It melts at 183 to <B> 183.5-. </B>
Instead of sodium carbonate, you can also use other alkaline agents with tel such. B. Alkalihydrogyde, alkaline earth hydroxide etc. use. The reaction can also medium in the presence of other solvents, such as. B. ethyl alcohol, iso-butyl alcohol, acetone, dioxane and the like, optionally in the presence of water, are carried out.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211255T | 1937-02-06 | ||
| CH206034T | 1937-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211255A true CH211255A (en) | 1940-08-31 |
Family
ID=25724256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211255D CH211255A (en) | 1937-02-06 | 1937-02-06 | Process for the preparation of a new ester of estradiol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211255A (en) |
-
1937
- 1937-02-06 CH CH211255D patent/CH211255A/en unknown
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