CH211259A - 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
- CH211259A CH211259A CH211259DA CH211259A CH 211259 A CH211259 A CH 211259A CH 211259D A CH211259D A CH 211259DA CH 211259 A CH211259 A CH 211259A
- Authority
- CH
- Switzerland
- Prior art keywords
- estradiol
- alkaline
- preparation
- agent
- dependent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 229960005309 estradiol Drugs 0.000 title claims description 5
- 229930182833 estradiol Natural products 0.000 title claims description 5
- 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 description 3
- 150000002148 esters Chemical class 0.000 title description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- -1 estradiol ester Chemical class 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- NCDHAIVZKJYMPV-IWJZLDOKSA-N C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2(CCCCCCCCCC(=O)O)O)CCC4=C3C=CC(=C4)O Chemical compound C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2(CCCCCCCCCC(=O)O)O)CCC4=C3C=CC(=C4)O NCDHAIVZKJYMPV-IWJZLDOKSA-N 0.000 claims description 2
- UETILLFPBWWSTP-BAQMTIIXSA-N [(8R,9S,13S,14S)-3-decanoyloxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] decanoate Chemical compound C1CC2=CC(OC(=O)CCCCCCCCC)=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC(OC(=O)CCCCCCCCC)[C@@]1(C)CC2 UETILLFPBWWSTP-BAQMTIIXSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 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 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 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
- 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
- 239000003513 alkali Substances 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 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
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
Verfabren zur Darstellung eines neuen Esters des Oestradiols. Es wurde gefunden, dass man zu einem neuen Ester des Oestradiols gelangen kann, wenn man Oestradiol-dicaprinat mit alkalisch reagierenden Mitteln in schonender Weise behandelt. Hierbei wird nur der Säurerest abgespalten, der an die pbenolische Hydroxyl- gruppe gebunden ist. Als alkalisch reagierende Mittel können zum Beispiel Alkalihydroxyde, Alkalicarbonate, Erdalkalibydroxyde, Mag nesia usw. verwendet werden.
Das so gewonnene Oestradiol-17-mono- caprinat bildet Kristalle vom F. 112-112,50. Es soll therapeutische Verwendung finden.
Während die partielle Verseifung von Diestern der Androstandiole zu Gemischen führt, die sich oft nur schwer trennen lassen, verläuft die Reaktion nach vorliegenden Ver fahren überraschenderweise durchaus einheit lich und man erhält den Oestradiol-17-mono- ester in so gut wie quantitativer Ausbeute.
Beispiel: 1 Teil Oestradiol-3,17-dicaprinat (Öl; Spd. 0,001 mm, 260-265' Badtemperatur; hergestellt zum Beispiel durch Einwirkung von Caprinylchlorid auf Oestradiol in Ge genwart von Pyridin) und 60 Teile einer 0,5%igen Lösung von Kaliumcarbonat in 95% Methylalkohol werden einige Zeit bei Zimmertemperatur verrührt.
Hierauf wird mit Salzsäure neutralisiert, mit Wasser ge fällt, filtriert und nacheinander mit Wasser verdünnter Sodalösung und Wasser gewa schen. Man erhält das Oestradiol-17-mono- caprinat in feinen Kristallblättchen, die sich aus Methylalkoholwasser umkristallisieren lassen. F. 112-112,50.
An Stelle von Kaliumcarbonat kann man auch andere alkalisch reagierende Mittel wie zum Beispiel Alkalihydroxyde, Erdalkalihy- droxyde usw. verwenden. Die Reaktion kann auch in Gegenwart anderer Lösungsmittel wie zum Beispiel Äthylalkohol, iso-Butyl- alkohol, Aceton, Dioxan und dergleichen gegebenenfalls in Gegenwart von Wasser durchgeführt werden.
Procedure for the preparation of a new ester of estradiol. It has been found that a new estradiol ester can be obtained if estradiol dicaprinate is treated gently with alkaline agents. Only the acid residue that is bound to the pbenolic hydroxyl group is split off. As the alkaline reacting agent, for example, alkali hydroxides, alkali carbonates, alkaline earth hydroxides, magnesia, etc. can be used.
The estradiol-17-monocaprinate obtained in this way forms crystals with a melting point of 112-112.50. It should find therapeutic use.
While the partial saponification of diesters of androstandiols leads to mixtures which are often difficult to separate, the reaction according to the present process surprisingly proceeds quite uniformly and the estradiol-17-monoester is obtained in virtually quantitative yield.
Example: 1 part of estradiol-3,17-dicaprinate (oil; Spd. 0.001 mm, 260-265 'bath temperature; produced for example by the action of caprinyl chloride on estradiol in the presence of pyridine) and 60 parts of a 0.5% solution of potassium carbonate in 95% methyl alcohol are stirred for some time at room temperature.
It is then neutralized with hydrochloric acid, precipitated with water, filtered and washed successively with water-diluted soda solution and water. The oestradiol-17-monocaprinate is obtained in fine crystal flakes which can be recrystallized from methyl alcohol water. F. 112-112.50.
Instead of potassium carbonate, other alkaline-reacting agents such as alkali hydroxides, alkaline earth hydroxides, etc. can also be used. The reaction can also be carried out in the presence of other solvents such as, for example, ethyl alcohol, isobutyl alcohol, acetone, dioxane and the like, if appropriate in the presence of water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211259T | 1937-02-06 | ||
| CH206034T | 1937-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211259A true CH211259A (en) | 1940-08-31 |
Family
ID=25724260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211259D CH211259A (en) | 1937-02-06 | 1937-02-06 | Process for the preparation of a new ester of estradiol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211259A (en) |
-
1937
- 1937-02-06 CH CH211259D patent/CH211259A/en unknown
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