DE191385C - - Google Patents
Info
- Publication number
- DE191385C DE191385C DENDAT191385D DE191385DA DE191385C DE 191385 C DE191385 C DE 191385C DE NDAT191385 D DENDAT191385 D DE NDAT191385D DE 191385D A DE191385D A DE 191385DA DE 191385 C DE191385 C DE 191385C
- Authority
- DE
- Germany
- Prior art keywords
- bismuth
- cholic acid
- salts
- acid
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical class C([C@H]1C[C@H]2O)[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 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims description 16
- 235000019416 cholic acid Nutrition 0.000 claims description 13
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000004380 Cholic acid Substances 0.000 claims description 12
- 229960002471 cholic acid Drugs 0.000 claims description 12
- 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 12
- 150000001621 bismuth Chemical class 0.000 claims description 8
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 229910052797 bismuth Inorganic materials 0.000 claims description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical class [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- -1 bismuth forms basic salts Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- XWNOTOKFKBDMAP-UHFFFAOYSA-N [Bi].[N+](=O)(O)[O-] Chemical compound [Bi].[N+](=O)(O)[O-] XWNOTOKFKBDMAP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940049676 bismuth hydroxide Drugs 0.000 description 1
- TZSXPYWRDWEXHG-UHFFFAOYSA-K bismuth;trihydroxide Chemical compound [OH-].[OH-].[OH-].[Bi+3] TZSXPYWRDWEXHG-UHFFFAOYSA-K 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002812 cholic acid derivative Substances 0.000 description 1
- 150000001842 cholic acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[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 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- .M191385 KLASSE 12 o. GRUPPE- .M191385 CLASS 12 or GROUP
Dr. EMIL WÖRNER in POSEN.Dr. EMIL WÖRNER in POSEN.
Das Wismut bildet bekanntlich sehr leicht in Wasser unlösliche basische Salze.As is well known, bismuth forms basic salts which are insoluble in water very easily.
Man kann daher Verbindungen der Cholsäure mit Wismut nicht dadurch herstellen, daß man in sonst üblicher Weise neutrale Wismutsalzlösungen mit einer Auflösung eines cholsauren Salzes umsetzt. Saure Wismutsalzlösungen sind ebenfalls nicht zu verwenden, da die Säure aus den cholsaurenIt is therefore not possible to produce compounds of cholic acid with bismuth by that one reacts neutral bismuth salt solutions with a solution of a cholic acid salt in the usual manner. Acid bismuth salt solutions are also not to be used, as the acid is derived from the cholic acids
ίο Salzen sofort die Cholsäure ausfällt.ίο Salts immediately the cholic acid precipitates.
Es wurde nun gefunden, daß man Wismutsalze der Cholsäure leicht erhalten kann, wenn man die in Wasser meist unlöslichen basischen Salze des Wismuts mit Auflösungen von cholsauren Salzen einige Zeit erwärmt. Es gelingt so, die Säure des Wismutsalzes völlig gegen Cholsäure auszutauschen. Ein Überschuß an cholsaurem Salz befördert die Reaktion erheblich.It has now been found that bismuth salts of cholic acid can easily be obtained if the basic salts of bismuth, which are usually insoluble in water, are mixed with solutions warmed for some time by cholic acid salts. This is how the acid of the bismuth salt succeeds to be completely exchanged for cholic acid. An excess of cholic acid salt promoted the response is substantial.
Man kann von neutralen Wismutsalzen ausgehen, diese durch Behandeln mit Wasser in basische Salze überführen und diese frisch erhaltenen basischen Salze mit cholsauren Salzen umsetzen.You can start from neutral bismuth salts by treating them with water Convert into basic salts and these freshly obtained basic salts with cholsauren Implement salts.
i. Beispiel: I kg basisch salpetersaures Wismut· wird mit einer konz. wäßrigen Auflösung von ι kg cholsaurem Natron zu einem feinen Brei verrührt und auf dem Dampfbade unter häufigem Durchrühren und Ersetzen des verdunsteten Wassers einige Stunden erhitzt. Man verdünnt dann das Reaktionsprodukt mit Wasser, rührt gut durch und läßt absetzen. Die über dem Niederschlage stehende Flüssigkeit wird durch ein Filter abgegossen. Der Rückstand wird dann in derselben Weise wiederholt mit Wasser gewaschen, auf einem Filter gesammelt und getrocknet.i. Example: I kg of basic nitric acid bismuth · is mixed with a conc. aqueous dissolution of ι kg of cholic acid soda mixed into a fine paste and poured on the Steam bath with frequent stirring and replacement of the evaporated water a few Heated for hours. The reaction product is then diluted with water, stirred well and allowed to settle. The one above that Precipitated liquid is poured off through a filter. The residue will then washed repeatedly with water in the same manner, collected on a filter and dried.
2. Beispiel: 1 kg neutrales Wismutnitrat wird mit 3 kg Wasser fein verrührt und unter wiederholtem Schütteln einige Stunden stehen gelassen. Man gießt dann das saure Wasser ab, wäscht nochmals mit Wasser nach und führt dann das so erhaltene basische Salz durch Behandeln mit einer Lösung- von 1 kg cholsaurem Natron in der in Beispiel 1 beschriebenen Weise in das Wismutsalz der Cholsäure über.2nd example: 1 kg of neutral bismuth nitrate is finely mixed with 3 kg of water and left to stand for a few hours with repeated shaking. You then pour the sour Water off, washes again with water and then leads the basic salt obtained in this way by treating with a Solution of 1 kg of sodium cholate in the manner described in Example 1 in the Cholic acid bismuth salt over.
Die so erhaltenen cholsauren Salze des Wismuts stellen gelblichweiße Pulver dar, die in Wasser ganz unlöslich sind. Sie unterscheiden sich voneinander durch einen größeren oder geringeren Gehalt an Cholsäure, entsprechend dem Säuregehalt des zur Darstellung verwandten Wismutsalzes.The cholic acid salts of bismuth obtained in this way are yellowish-white powders, which are completely insoluble in water. They differ from one another in one greater or lesser content of cholic acid, according to the acidity of the zur Representation of related bismuth salt.
Die nach Beispiel 1 dargestellten Salze enthalten gegen 35 Prozent Cholsäure, während Beispiel 2 solche mit ungefähr 65 Prozent Cholsäure liefert.The salts shown according to Example 1 contain against 35 percent cholic acid, while Example 2 provides those with approximately 65 percent cholic acid.
Alkohol entzieht ihnen unter Zersetzung Cholsäure. In Äther, Benzol, Chloroform, Petroläther sind sie ganz unlöslich. .Alcohol removes cholic acid from them by decomposing them. In ether, benzene, chloroform, They are completely insoluble in petroleum ether. .
Mineralsäuren zersetzen sie, das" Wismutsalz der Mineralsäure geht in Lösung, Chol-Mineral acids decompose them, the "bismuth salt of the mineral acid goes into solution, Chol-
säure bleibt ungelöst. Alkalien zersetzen sie ebenfalls unter Abscheidung von Wismuthydroxyd und Bildung von löslichen cholsauren Alkalien.acid remains undissolved. Alkalis also decompose with the separation of bismuth hydroxide and formation of soluble cholic acid alkalis.
Die Salze sollen therapeutische Anwendung finden.The salts are said to be used therapeutically.
Claims (1)
Verfahren zur Herstellung von Wismutsalzen der Cholsäure, dadurch gekennzeichnet, daß basische Salze des Wismuts mit Auflösungen von cholsauren Salzen erhitzt werden.Patent claims:
Process for the production of bismuth salts of cholic acid, characterized in that basic salts of bismuth are heated with solutions of cholic acid salts.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE191385C true DE191385C (en) |
Family
ID=454783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT191385D Active DE191385C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE191385C (en) |
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0
- DE DENDAT191385D patent/DE191385C/de active Active
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