CH199982A - Process for the preparation of a new ester. - Google Patents
Process for the preparation of a new ester.Info
- Publication number
- CH199982A CH199982A CH199982DA CH199982A CH 199982 A CH199982 A CH 199982A CH 199982D A CH199982D A CH 199982DA CH 199982 A CH199982 A CH 199982A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- new
- androstenol
- ester
- compound
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229940106681 chloroacetic acid Drugs 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960003604 testosterone Drugs 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
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0025—Esters
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung eines neuen Esters. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung eines neuen Esters, welches dadurch gekennzeichnet ist, dass man auf 44,5 -Androstenol - (17) - an - (3) eine Verbindung einwirken lässt, die das Radikal der Chloressigsäure enthält, wie z. B. die freie Säure selbst, ihre Ester, Halogenide oder ihr Anhydrid.
Der so gewonnene V4,6-Androstenol-(17)- on-(3)-chloressigsäureester der Formel
EMI0001.0010
hat den F. 123 bis 124'. Derselbe kann durch Umsetzung mit primären und sekun dären Aminen in Verbindungen übergeführt werden, die in der Form ihrer Salze wasser löslich sind.
Die neue Verbindung soll therapeutische Verwendung finden oder als Zwischen- Produkt zur Herstellung therapeutisch ver wendbarer Stoffe dienen.
Beispiel: Ein Gemisch von 1,1 Teilen Testosteron und 1,2 Teilen Chloressigsäureanhydrid wird einige Zeit auf 110 erwärmt. Nach dem Erkalten wird die Schmelze in wässerigem Aceton gelöst und durch Wasserzugabe zur Kristallisation gebracht. Die Kristalle wer den abfiltriert, mit verdünnter Sodalösung und Wasser gewaschen und getrocknet.
Zur weiteren Reinigung kann der d4,5-An.drostenol- (17)-on-(3)-chloressigsäureester aus Hegan umkristallisiert werden. Er schmilzt bei 123 bis 124'. Derselbe kann durch Umsetzung, z. B. mit Diäthylamin, in eine Verbindung übergeführt werden, die zum Beispiel als Hy- drochlorid wasserlöslich ist.
Process for the preparation of a new ester. The subject of the present patent is a process for the preparation of a new ester, which is characterized in that a compound is allowed to act on 44,5 -androstenol - (17) - to - (3) which contains the radical of chloroacetic acid, such as . B. the free acid itself, its esters, halides or its anhydride.
The V4,6-androstenol- (17) -on- (3) -chloroacetic acid ester of the formula obtained in this way
EMI0001.0010
has the F. 123 to 124 '. The same can be converted by reaction with primary and secondary amines in compounds which are water-soluble in the form of their salts.
The new compound should find therapeutic use or serve as an intermediate product for the production of therapeutically ver usable substances.
Example: A mixture of 1.1 parts testosterone and 1.2 parts chloroacetic anhydride is heated to 110 for some time. After cooling, the melt is dissolved in aqueous acetone and crystallized by adding water. The crystals who filtered off, washed with dilute soda solution and water and dried.
For further purification, the d4,5-an.drostenol- (17) -one- (3) -chloroacetic acid ester can be recrystallized from Hegan. It melts at 123 to 124 '. The same can be done by implementation, e.g. B. with diethylamine, can be converted into a compound that is water-soluble, for example as hydrochloride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH195775T | 1935-08-02 | ||
| CH199982T | 1935-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199982A true CH199982A (en) | 1938-09-15 |
Family
ID=25722793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199982D CH199982A (en) | 1935-08-02 | 1935-08-02 | Process for the preparation of a new ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199982A (en) |
-
1935
- 1935-08-02 CH CH199982D patent/CH199982A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH199982A (en) | Process for the preparation of a new ester. | |
| CH199983A (en) | Process for the preparation of a new ester. | |
| AT111249B (en) | Process for the preparation of complex antimony compounds. | |
| CH218361A (en) | Process for the production of a cyclopentano-dimethyl-polyhydro-phenanthrene-carboxylic acid. | |
| DE931947C (en) | Process for the preparation of 20, 21-pregnanketol esters | |
| DE845347C (en) | Process for the preparation of pyridine-mercury compounds | |
| AT216671B (en) | Process for the preparation of compounds of various penicillins with sulfonamides | |
| CH240162A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH199676A (en) | Process for the preparation of a substituted thiazolecarboxamide. | |
| CH201536A (en) | Process for the preparation of a new ester. | |
| CH183065A (en) | Process for the preparation of benzilic acid-2-diethylaminoethanol ester. | |
| CH240163A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH174886A (en) | Process for the preparation of an oxycarboxylic acid. | |
| CH296267A (en) | Process for the preparation of the piperidinoethyl ester of 4-amino-2-oxy-benzoic acid. | |
| CH139418A (en) | Process for the preparation of a one-sided heterocyclically acylated diamine. | |
| CH120257A (en) | Process for the preparation of a new oxynaphthalene carboxylic acid. | |
| CH201204A (en) | Process for preparing a sulfonic acid amide compound. | |
| CH180874A (en) | Process for the preparation of an acylated dihydrofollicle hormone. | |
| CH240160A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH240167A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH207497A (en) | Process for the preparation of an aldehyde of the cyclopentanopolyhydrophenanthrene series. | |
| CH240164A (en) | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. | |
| CH298740A (en) | Process for the preparation of a heterocyclic carbamic acid derivative. | |
| CH206120A (en) | Process for the preparation of a new ester. | |
| CH296180A (en) | Process for the preparation of a new disubstituted nicotinic acid amide. |