CH222901A - Process for the preparation of a new ester. - Google Patents
Process for the preparation of a new ester.Info
- Publication number
- CH222901A CH222901A CH222901DA CH222901A CH 222901 A CH222901 A CH 222901A CH 222901D A CH222901D A CH 222901DA CH 222901 A CH222901 A CH 222901A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- new ester
- deoxycorticosterone
- propionate
- pregnen
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 4
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 claims description 4
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 claims description 4
- 229940119740 deoxycorticosterone Drugs 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 230000002349 favourable effect Effects 0.000 claims description 2
- 230000001766 physiological effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 2
- 235000010334 sodium propionate Nutrition 0.000 description 2
- 239000004324 sodium propionate Substances 0.000 description 2
- 229960003212 sodium propionate Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZPNUREIHBRWTHU-PAPGYHMHSA-N O=C1CC2CC[C@H]3[C@@H]4CC=C(C(CCl)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C Chemical compound O=C1CC2CC[C@H]3[C@@H]4CC=C(C(CCl)=O)[C@]4(CC[C@@H]3[C@]2(CC1)C)C ZPNUREIHBRWTHU-PAPGYHMHSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Yeilahr en zur Darstellung eines neuen Esters. Es wurde gefunden, dass man zu einem neuen Ester des Desoxycorticosterons ge langen kann, wenn man ein 21-Halogen- pregnen-3,20-dion mit einem propionylieren- den Mittel behandelt.
Geeignete propionylierende Mittel sind z. B. die Salze der Propionsäure, wie Natriumpropionat.
Das so gewonnene De@soxycorticosteron- propionat schmilzt bei 163-164'. Es zeich net sich durch besonders günstige physio logische Wirkung aus und soll deshalb thera peutische Verwendung finden.
<I>Beispiel,:</I> Zu einer Lösung von 0,5 Teilen 21-Chlor- pregnen-3,20-dion in 5 Teilen absolutem Al kohol wird 1 Teil Natriumpropionat zu gefügt. Man erwärmt hierauf das Gemisch bis zur beendeten gochsalzabscheidung und filtriert. Das durch Wasserzusatz zum Fil trat zuerst ölig ausfallende, bald jedoch kristallisierende Reaktionsprodukt wird auf der Nutsche mit Wasser gewaschen.
Man ge winnt so das Desoxycorticosteron-propionat, das nach Umkristallisation aus Aceton- Petroläther bei 163-164' schmilzt.
Years to prepare a new ester. It has been found that a new ester of deoxycorticosterone can be obtained if a 21-halo-pregnen-3,20-dione is treated with a propionylating agent.
Suitable propionylating agents are e.g. B. the salts of propionic acid, such as sodium propionate.
The de @ soxycorticosterone propionate obtained in this way melts at 163-164 '. It is characterized by a particularly favorable physiological effect and should therefore be used therapeutically.
<I> Example: </I> 1 part of sodium propionate is added to a solution of 0.5 part of 21-chloro-pregnen-3,20-dione in 5 parts of absolute alcohol. The mixture is then heated until the separation of sodium chloride has ended and filtered. The reaction product which precipitated out oily but soon crystallized when water was added to the filter was washed with water on the suction filter.
The deoxycorticosterone propionate is thus obtained, which, after recrystallization from acetone-petroleum ether, melts at 163-164 '.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH222901T | 1938-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH222901A true CH222901A (en) | 1942-08-15 |
Family
ID=4452806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH222901D CH222901A (en) | 1938-06-27 | 1938-06-27 | Process for the preparation of a new ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH222901A (en) |
-
1938
- 1938-06-27 CH CH222901D patent/CH222901A/en unknown
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