CH207669A - Process for the production of an organic gold compound. - Google Patents
Process for the production of an organic gold compound.Info
- Publication number
- CH207669A CH207669A CH207669DA CH207669A CH 207669 A CH207669 A CH 207669A CH 207669D A CH207669D A CH 207669DA CH 207669 A CH207669 A CH 207669A
- Authority
- CH
- Switzerland
- Prior art keywords
- gold
- production
- compound
- water
- soluble
- Prior art date
Links
- 150000002344 gold compounds Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 208000006379 syphilis Diseases 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 claims 2
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960003067 cystine Drugs 0.000 description 3
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- GHPCICSQWQDZLM-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-1-methyl-3-propylurea Chemical compound CCCNC(=O)N(C)S(=O)(=O)C1=CC=C(Cl)C=C1 GHPCICSQWQDZLM-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000002343 gold Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Description
Verfahren zur Herstellung einer organischen Goldverbindung. Es ist bekannt, gegen Tuberkulose wirk same Goldverbindungen des Cystins dadurch herzustellen, dass man Cystin in Natronlauge löst, zu der Lösung Goldchlorid hinzugibt und das so entstandene Goldsalz des Cystins durch Alkoholzugabe ausfällt. Die so ge wonnene Verbindung stellt sich als das Natriumsalz einer Dicarbonsäure dar, das in saurem Medium unlöslich ist.
Im Haupt patent ist ein Verfahren beschrieben, durch welches es gelingt, neutrale in saurem und alkalischem Medium gleichermassen lösliche schwefelhaltige Goldverbindungen herzu stellen, die eine gute Wirksamkeit insbeson dere gegen Syphilis, und zwar auch gegen arsenresistente Fälle zeigen.
Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung des Disulfidessig- säure-N-methylglukamids, welches dadurch gekennzeichnet ist, dass man ein wasserlös liches Goldsalz in wässriger Lösung auf Di- sulfidessigsäure-N-methylglukamid einwir ken lässt.
Es wurde weitergefunden, dass man zu einer für therapeutische Zwecke, insbeson dere für die Syphilisbekämpfung, in gleicher Weise wirksamen Verbindung gelangt, wenn man ein wasserlösliches Goldsalz, insbeson dere Goldchlorid, auf ss-Disulfidpropionsäure- N-methylglukamid einwirken lässt. Bei genü gend weitgehender Reinigung sind von den als Ausgangsstoffe angewandten Goldsalzen nur das Gold und kein anderer Rest in dem Umsetzungsprodukt enthalten.
Die so erhältliche neue Verbindung stellt eine gelbe amorphe Substanz dar, die in Wasser leicht, in Äthylalkohol schwer und in Äther und Benzol unlöslich ist.
<I>Beispiel:</I> 25,5 g Methylglukamin, in 50 cms Wasser gelöst, werden portionsweise mit 8,5 g ss-Chlorpropionsäurechlorid, analog wie beim Beispiel des Hauptpatentes, verarbeitet; dann wird mit aus 2,5 g Iialiummethylat dargestelltem Ialiumdisulfid, analog wie im Beispiel des Hauptpatentes, umgesetzt. Man erhält einen zähen Sirup, der nicht kristalli siert, 4 g des so erhaltenen ss-Disulfidpro- pionsäure-N-methylglukamids werden in 10 cm:' Wasser gelöst und eine Lösung von <B>1,7</B> g Goldchlorid in 7 cm' Wasser zugegeben.
Die zunächst dunkel gefärbte Lösung wird rasch hell; dann wird klar filtriert und in Alkohol eingegossen. Die Goldverbindung scheidet sich als hellgelbes festes Pulver ab; sie wird abgesaugt und mit Alkohol und Äther gewaschen. Ausbeute: 1,8 g
Process for the production of an organic gold compound. It is known that gold compounds of cystine that are effective against tuberculosis can be produced by dissolving cystine in sodium hydroxide solution, adding gold chloride to the solution and precipitating the resulting gold salt of cystine by adding alcohol. The compound obtained in this way is the sodium salt of a dicarboxylic acid, which is insoluble in an acidic medium.
The main patent describes a process by means of which it is possible to produce neutral sulfur-containing gold compounds which are equally soluble in acidic and alkaline media and which are particularly effective against syphilis, including arsenic-resistant cases.
The main patent relates to a process for the production of disulfidacetic acid-N-methylglucamide, which is characterized in that a water-soluble gold salt in aqueous solution is allowed to act on disulfidacetic acid-N-methylglucamide.
It has also been found that a compound which is equally effective for therapeutic purposes, in particular for combating syphilis, is obtained if a water-soluble gold salt, in particular gold chloride, is allowed to act on s-disulfidpropionic acid-N-methylglucamide. With sufficient extensive purification, of the gold salts used as starting materials, only the gold and no other remainder are contained in the reaction product.
The new compound obtained in this way is a yellow amorphous substance which is light in water, difficult in ethyl alcohol, and insoluble in ether and benzene.
<I> Example: </I> 25.5 g of methylglucamine, dissolved in 50 cms of water, are processed in portions with 8.5 g of s-chloropropionic acid chloride, analogously to the example of the main patent; then it is reacted with Ialium disulfide prepared from 2.5 g of Iialiummethylat, analogously to the example of the main patent. A viscous syrup is obtained which does not crystallize, 4 g of the β-disulfide propionic acid N-methylglucamide obtained in this way are dissolved in 10 cm of water and a solution of 1.7 g of gold chloride in 7 cm 'of water was added.
The initially dark colored solution quickly becomes light; then it is filtered clear and poured into alcohol. The gold compound is deposited as a light yellow solid powder; it is suctioned off and washed with alcohol and ether. Yield: 1.8 g
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE207669X | 1935-10-30 | ||
| CH199314T | 1936-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH207669A true CH207669A (en) | 1939-11-15 |
Family
ID=25723248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH207669D CH207669A (en) | 1935-10-30 | 1936-10-23 | Process for the production of an organic gold compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH207669A (en) |
-
1936
- 1936-10-23 CH CH207669D patent/CH207669A/en unknown
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