CH169588A - Process for preparing a bile acid compound. - Google Patents
Process for preparing a bile acid compound.Info
- Publication number
- CH169588A CH169588A CH169588DA CH169588A CH 169588 A CH169588 A CH 169588A CH 169588D A CH169588D A CH 169588DA CH 169588 A CH169588 A CH 169588A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- soluble
- compound
- preparing
- acid compound
- Prior art date
Links
- -1 bile acid compound Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003613 bile acid Substances 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229960003964 deoxycholic acid Drugs 0.000 claims description 3
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N anhydrous gallic acid Natural products OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 1
- 229940074391 gallic acid Drugs 0.000 claims 1
- 235000004515 gallic acid Nutrition 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung einer Gallensäureverbindung. Das vorliegende Verfahren betrifft die Darstellung einer Gallensäureverbindung. Es ist dadurch gekennzeichnet, dass man 1 . 8 . 3 . 6-Aminonaphtoldisulfosäure mit I)esoxycholsäureazid behandelt.
<I>Beispiel:</I> 24,0 gr 1.8.3.6-Aminonaphtoldisulfo- säure, gelöst in 90 cm' n-Natronlauge, wer den mit 25,0 gr Desoxycholsäureazid (dar gestellt durch Einwirkenlassen der theore tischen Menge Salzsäure und Natriumnitrit auf 24,4 gr Desoxycholsäurehydrazid, Ab saugen und Auswaschen mit Wasser) ver setzt und zu der Suspension unter bestän digem Rühren<B>90</B> cm' n-Natronlauge im Laufe von 15 Minuten zugegeben. Man er wärmt langsam auf 55 und hält diese Tem peratur während 30 Minuten bei.
Beim An säuern mit Essigsäure findet eine stärkere Ausscheidung statt; man saugt von dieser ab, konzentriert die essigsaure Lösung im Vakuum bei<B>50'</B> auf ein kleines Volumen und versetzt mit absolutem Alkohol bis zur dicken Fällung. Nach einigen Stunden wird abgesaugt, mit absolutem Alkohol nach gewaschen und das noch dunkel gefärbte Rohprodukt aus Alkohol umkristallisiert, indem man es mit 30 cm' Wasser in der Hitze löst, langsam mit 500 cm3 absolutem Alkohol versetzt, so dass die Lösung bestän dig siedet, und heiss filtriert. Die Desoxy- cholalylaminonaphtoldisulfosäure (1.8.3.6) scheidet sich als flockig gallertige Masse aus und wird abgesaugt, mit absolutem Alkohol gewaschen und im Vakuum getrocknet.
Das erhaltene hellgraue Pulver ist leicht löslich in Wasser mit lackmussaurer Reaktion, etwas löslich in kaltem, ziemlich löslich in heissem Alkohol. In konzentrierter Schwefelsäure löst sich die Verbindung anfangs farblos, mit der Zeit gelb werdend.
Die neue Verbindung soll zu therapeu tischen Zwecken und als Zwischenprodukt bei der Herstellung von pharmazeutischen Präparaten Verwendung finden.
Process for preparing a bile acid compound. The present method relates to the preparation of a bile acid compound. It is characterized in that 1. 8th . 3. 6-aminonaphthol disulfonic acid treated with I) esoxycholic acid azide.
<I> Example: </I> 24.0 g 1.8.3.6-aminonaphthol disulphonic acid, dissolved in 90 cm 'n sodium hydroxide solution, mixed with 25.0 g deoxycholic acid azide (produced by allowing the theoretical amount of hydrochloric acid and sodium nitrite to act to 24.4 g deoxycholic acid hydrazide, sucking off and washing out with water) and added to the suspension with constant stirring 90 cm 'n sodium hydroxide solution over the course of 15 minutes. It is slowly warmed to 55 and held at this temperature for 30 minutes.
When acidifying with acetic acid, greater excretion takes place; it is suctioned off, the acetic acid solution is concentrated in a vacuum at <B> 50 '</B> to a small volume and mixed with absolute alcohol until a thick precipitation occurs. After a few hours, it is filtered off with suction, washed with absolute alcohol and the crude product, which is still dark in color, is recrystallized from alcohol by dissolving it with 30 cm of water in the heat, slowly adding 500 cm3 of absolute alcohol so that the solution boils constantly, and filtered hot. The deoxycholalylaminonaphthol disulfonic acid (1.8.3.6) separates out as a flaky gelatinous mass and is filtered off with suction, washed with absolute alcohol and dried in vacuo.
The light gray powder obtained is easily soluble in water with a lacquer acid reaction, somewhat soluble in cold, fairly soluble in hot alcohol. In concentrated sulfuric acid, the compound initially dissolves colorless, but turns yellow over time.
The new compound is intended to be used for therapeutic purposes and as an intermediate in the manufacture of pharmaceutical preparations.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE169588X | 1932-04-09 | ||
| CH166967T | 1933-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169588A true CH169588A (en) | 1934-05-31 |
Family
ID=25718373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169588D CH169588A (en) | 1932-04-09 | 1933-04-02 | Process for preparing a bile acid compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169588A (en) |
-
1933
- 1933-04-02 CH CH169588D patent/CH169588A/en unknown
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