DE567274C - Process for the production of water-soluble arsenic antimony compounds - Google Patents
Process for the production of water-soluble arsenic antimony compoundsInfo
- Publication number
- DE567274C DE567274C DEI42226D DEI0042226D DE567274C DE 567274 C DE567274 C DE 567274C DE I42226 D DEI42226 D DE I42226D DE I0042226 D DEI0042226 D DE I0042226D DE 567274 C DE567274 C DE 567274C
- Authority
- DE
- Germany
- Prior art keywords
- water
- production
- compounds
- antimony compounds
- arsenic antimony
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 5
- DLISVFCFLGSHAB-UHFFFAOYSA-N antimony arsenic Chemical class [As].[Sb] DLISVFCFLGSHAB-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 claims description 6
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical group OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- QJQZEJFUIOWFMS-UHFFFAOYSA-N formaldehyde;sulfanediol Chemical class O=C.OSO QJQZEJFUIOWFMS-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 2
- 208000006558 Dental Calculus Diseases 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Gewinnung von wasserlöslichen Arsenantimonverbindungen Es wurde gefunden, daß man aus den bisher ungenutzten Aminoarylarsenoantimonverbindungen therapeutisch wertvolle Verbindungen gewinnen kann, wenn man sie nach an sich üblichen Methoden in ihre wasserlöslichen neutralen Formaldehydsulfoxylatverbindungen überführt.Process for the production of water-soluble arsenic antimony compounds It has been found that from the previously unused aminoarylarsenoantimony compounds therapeutically valuable compounds can be obtained if they are used according to the usual Methods converted into their water-soluble, neutral formaldehyde sulfoxylate compounds.
Die auf verschiedenen Wegen erhältlichen Ausgangsstoffe sind z. B. nach der Formel (H, N # Ar # As)" Sb", zusammengesetzt. Darin entspricht im allgemeinen it der Zahl 3 und m der Zahl 2 entsprechend folgender Strukturformel: Die Einwirkung von Formaldehydsulfoxylat kann man in wässeriger Lösung oder in einem organischen Lösemittel bei neutrale, saurer oder alkalischer Reaktion erfolgen lassen; man kann auf diese Weise ein oder mehrere Sulfoxvlatreste in die Aminoarylarsezzoantimonverbindungen einführen.The starting materials available in various ways are z. B. according to the formula (H, N # Ar # As) "Sb" composed. In general, it corresponds to the number 3 and m to the number 2 according to the following structural formula: The action of formaldehyde sulfoxylate can take place in an aqueous solution or in an organic solvent with a neutral, acidic or alkaline reaction; in this way one or more sulfoxylate residues can be introduced into the aminoarylarsezzoantimony compounds.
Es ist somit gelungen, die Arsenantimonverbindungen (H_ N . Ar # As)" Sb"z in neutral lösliche Abkömmlinge überzuführen, welche es gestatten, diese wichtigen Kombinationsverbindungen für die Bekämpfung von Infektionskrankheiten nutzbar zu machen.It has thus been possible to use the arsenic antimony compounds (H_ N. Ar # As) " Sb "z to be converted into neutrally soluble derivatives, which allow these important Combination compounds for combating infectious diseases usable too do.
Von den in der Patentschrift 451701 beschriebenen Formaldehydsulfoxylatderivaten von sind die Ausgangsstoffe und die Endprodukte des vorliegenden Verfahrens grundsätzlich dadurch unterschieden, daß sie das Antimon in anorganischer, nicht an Kohlenstoff gebundener Form enthalten.Of the formaldehyde sulfoxylate derivatives of the starting materials and the end products of the present process are fundamentally differentiated in that they contain the antimony in an inorganic form that is not bound to carbon.
Solche Verbindungen sind technisch wesentlich einfacher herzustellen als die unter Benutzung von organischen Antimonverbindungen gewonnenen Produkte der Patentschrift 451701. Es ist bemerkenswert, daß die Einführung des Forma.ldehydsulfoxylatrestesglatt und ohne Abspaltung des anorganischen Antimons gelang und daß diese verhältnismäßig einfach zugänglichen Verbindungen einen hohen chemotherapeutischen Index bei verschiedenen experimentellen Infektionskrankheiten gezeigt haben.Such connections are technically much easier to make than the products obtained using organic antimony compounds the patent specification 451701. It is noteworthy that the introduction of the formaldehyde sulfoxylate residue is smooth and succeeded without splitting off the inorganic antimony and that this was proportionate readily available compounds have a high chemotherapeutic index at various experimental infectious diseases have shown.
Beispiel 1 Zu einer Lösung von 11 g Brechweinstein und 11 g Kaliumnatriumartrat in 300 ccm Wasser gibt man .1o ccm 5 n-Natronlauge hinzu. Dazu fügt man eine Lösung von 9 g 4-Oxy-3-aminophenylarsinacetat in Methylalkohol. Die Flüssigkeit färbt sich alsbald dunkelbraun. Nach kurzem Stehen fällt man die Lösung mit Ammoniumchloridlösung aus. Man saugt das gebildete q.-Oxy-3-aminophenylarsenöantimon ab, wäscht aus, löst die erhaltene braune Paste in der eben nötigen Menge verdünnter Natronlauge und setzt 79 Formaldehydsulfoxylat hinzu. Nach dreitägigem Stehen neutralisiert man mit verdünnter Säure, filtriert und fällt die gebildete Verbindung durch Einrühren in Methylalkohol aus. Nach dem Abtrennen und Trocknen im Vakuum erhält matt ein dunkelbraunes, in Wasser leicht und neutral lösliches, bei Luftabschluß gut haltbares Pulver. Es ist ungefähr ein Sulfoxylatrest in das Molekül eingetreten.EXAMPLE 1 10 cc of 5N sodium hydroxide solution are added to a solution of 11 g of tartar of tartar and 11 g of potassium sodium tartrate in 300 cc of water. A solution of 9 g of 4-oxy-3-aminophenylarsine acetate in methyl alcohol is added. The liquid soon turns dark brown. After standing for a short time, the solution is precipitated with ammonium chloride solution. The q.-oxy-3-aminophenylarsenoantimony formed is filtered off with suction, washed out, the brown paste obtained is dissolved in the required amount of dilute sodium hydroxide solution and 79 formaldehyde sulfoxylate is added. After standing for three days, the mixture is neutralized with dilute acid, filtered and the compound formed is precipitated by stirring into methyl alcohol. After separation and drying in vacuo, a matt dark brown powder which is easily and neutrally soluble in water and which can be kept well in the absence of air is obtained. Approximately one sulfoxylate residue has entered the molecule.
Sämtliche Operationen sind bei diesem und den folgenden Beispielen unter tunlichstem Ausschluß von Sauerstoff vorzunehmen. Beispiel a Die nach Beispiel i hergestellte Paste des 4-Oxy-3-aminophenylarsenoantimons wird mit einer Lösung von 16 g Formaldehydsulfoxylat geschüttelt, wobei Lösung eintritt. Nach 2 Tagen wird die Lösung filtriert und die erhaltene Verbindung durch Einrühren in Methylalkohol ausgefällt. Man erhält ein braunes, leicht und neutral in Wasser lösliches Pulver. Es sind ungefähr zwei Sulfoxylatreste in das Molekül eingetreten. Beispiel 3 Die nach Beispiel i hergestellte Paste des s-Oxy-3-aminophenylarsenoantimons wird mit Wasser aasgeschlämmt, in etwa 3,5 ccm 5 n-Salzsäure gelöst, 16 g Formaldehydsulfoxylat hinzugefügt und die Mischung in verschlossener Flasche geschüttelt. Nach etwa 2 Tagen wird mit verdünnter Natronlauge neutralisiert, filtriert und die gebildete Verbindung durch Einrühren in Methylalkohol ausgefällt. Nach dem Abtrennen und Trocknen im Vakuum erhält man ein braunes, leicht und neutral in Wasser lösliches Pulver. Es sind ungefähr drei Sulfoxylatreste in das Molekül eingetreten.In this and the following examples, all operations should be carried out with the greatest possible exclusion of oxygen. Example a The paste of 4-oxy-3-aminophenylarsenoantimone produced according to Example i is shaken with a solution of 16 g of formaldehyde sulfoxylate, during which time solution occurs. After 2 days, the solution is filtered and the compound obtained is precipitated by stirring into methyl alcohol. A brown powder which is easily and neutrally soluble in water is obtained. Approximately two sulfoxylate residues have entered the molecule. EXAMPLE 3 The paste of s-oxy-3-aminophenylarsenoantimone produced according to Example 1 is slurried with water, dissolved in about 3.5 cc of 5N hydrochloric acid, 16 g of formaldehyde sulfoxylate are added and the mixture is shaken in a sealed bottle. After about 2 days, the mixture is neutralized with dilute sodium hydroxide solution, filtered and the compound formed is precipitated by stirring in methyl alcohol. After separation and drying in vacuo, a brown powder which is easily and neutrally soluble in water is obtained. About three sulfoxylate residues have entered the molecule.
Läßt man im obigen Beispiel nur 7 g Formaldehydsulfoxylat einwirken und arbeitet nach einigen Stunden auf, erhält man ein Produkt, das nur etwa einen Sulfoxylatrest im Molekül hat.In the above example, only 7 g of formaldehyde sulfoxylate are allowed to act and after a few hours working up, you get a product that is only about one Has sulfoxylate residue in the molecule.
Ein entsprechendes Ergebnis erzielt man, wenn man bei diesem oder den vorangehenden Beispielen, z. B. vom q.-Oxy-3-aminophenylarsenoantimonhydrochlorid oder vom 4-Aminophenylarsenoantimon ausgeht.A corresponding result can be achieved if one works with this or the previous examples, e.g. B. from q.-Oxy-3-aminophenylarsenoantimony hydrochloride or starts from 4-aminophenylarsenoantimony.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI42226D DE567274C (en) | 1931-08-02 | 1931-08-02 | Process for the production of water-soluble arsenic antimony compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI42226D DE567274C (en) | 1931-08-02 | 1931-08-02 | Process for the production of water-soluble arsenic antimony compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE567274C true DE567274C (en) | 1932-12-30 |
Family
ID=7190735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI42226D Expired DE567274C (en) | 1931-08-02 | 1931-08-02 | Process for the production of water-soluble arsenic antimony compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE567274C (en) |
-
1931
- 1931-08-02 DE DEI42226D patent/DE567274C/en not_active Expired
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