CH242529A - Process for the preparation of m- (2,4-diamino-1,3,5-triazinyl- (6)) -amino-phenylarsine oxide. - Google Patents
Process for the preparation of m- (2,4-diamino-1,3,5-triazinyl- (6)) -amino-phenylarsine oxide.Info
- Publication number
- CH242529A CH242529A CH242529DA CH242529A CH 242529 A CH242529 A CH 242529A CH 242529D A CH242529D A CH 242529DA CH 242529 A CH242529 A CH 242529A
- Authority
- CH
- Switzerland
- Prior art keywords
- triazinyl
- diamino
- amino
- preparation
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 4
- CXKRDMQZBMZKKJ-UHFFFAOYSA-N arsine oxide Chemical compound [AsH3]=O CXKRDMQZBMZKKJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- LVKZSFMYNWRPJX-UHFFFAOYSA-N benzenearsonic acid Natural products O[As](O)(=O)C1=CC=CC=C1 LVKZSFMYNWRPJX-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229940071870 hydroiodic acid Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 4
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UTZPGFZOSLGODE-UHFFFAOYSA-N oxo(phenyl)-$l^{5}-arsane Chemical class O=[AsH2]C1=CC=CC=C1 UTZPGFZOSLGODE-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical class O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001495 arsenic compounds Chemical class 0.000 description 1
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical class O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 description 1
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical class O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940093920 gynecological arsenic compound Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- AWYSLGMLVOSVIS-UHFFFAOYSA-N phenyl(phenylarsanylidene)arsane Chemical compound C1=CC=CC=C1[As]=[As]C1=CC=CC=C1 AWYSLGMLVOSVIS-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/80—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Terfaliren zur Darstellung von m-[2,4-1)iamino-I,3,5-triazinyl-(6))-amino-plienylarsinoxyd. Bei der Behandlung vieler Infektions krankheiten spielen organische Arsenverbin- dungen eine hervorragende Rolle. In der Hauptsache werden zur Bekämpfung dieser Krankheiten Abkömmlinge der Phenylarson- säuren und solche des Arsenobenzols verwen det.
Von den Derivaten des Phenylarsinoxyds hat bisher nur das 3-Amino-4-oxy-phenyl- arsinoxyd in der Therapie Eingang gefunden. Diese Verbindung besitzt den grossen Nach teil, dass sie sehr oxydationsempfindlich ist. Sie kann deshalb auch nicht in alkalischer Lösung verwendet werden.
Es wurde nun gefunden, dass die Tri- a,zinyl-amino-phenylarsinoxyde, eine neue Klasse von Abkömmlingen des Phenylarsin- oxyds, besonders wertvolle therapeutische Eigenschaften besitzen. Sie werden durch Reduktion der entsprechenden Arsonsäuren, vorzugsweise mit schwefliger Säure bei Ge genwart von Jodwasserstoffsäure, erhalten.
Die bisher unbekannten Triazinyl-amino- phenylarsinoxyde sind farblose, kristallisierte Verbindungen, die keinen definierten Schmelz- p un 'kt besitzen. Si' Si' lösen sich leicht in Al- halien. Aus der alkalischen Lösung werden sie durch Säuren wieder ausgefällt.
Die Ver bindungen besitzen eine grosse therapeutische Breite und ausserdem noch die für die prak tische Anwendung besonders wichtige Eigen schaft, auch in alkalischer Lösung gegen den Sauerstoff der Luft beständig zu sein. Die Arsinoxyde gehen bekanntlich durch Einwirkung von Alkalihydroxyden unter Hydratisierung in die Alkalisalze von Ar- si.nigsäuren über.
Die erfindungsgemäss dar gestellten Arsinoxyde lassen sich in Form dieser arsinigsauren Salze in wässerige Lö sung überführen. Derartige Lösungen sind luftbeständig und eignen sich zu Injektions zwecken.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von m- [2,4- Diamino -1, 3" 5 -- triazinyl - (6) ] -amino-phenyl- arsinoxyd, das dadurch gekennzeichnet ist, dass m - [2,4 - Diamino -1,3, 5 - triazinyl - (6) ] - -phenylarsonsäure mit einem Reduk- i amino tionsmittel behandelt wird.
Vorzugsweise wird als Reduktionsmittel schweflige Säure bei Gegenwart von Jodwasserstoffsäure ver wendet.
Das bisher unbekannte m-[2,4-Diamino- 1, 3; 5-triazinyl - (6) ] -, amino - phenylarsinogyd löst sich unter Salzbildung in wässerigen Laugen. Aus der klaren, farblosen Lösung wird durch Zugabe von Säuren das Arsin- ogyd wieder ausgefällt. Die Verbindung soll als Arzneimittel verwendet werden.
<I>Beispiel:</I> 10 Gewichtsteile m-[2,4-Diamino-1,3.,5- triazinyl-(6)]-amino-phenylarsonsäure wer den in 2,00 Gewichtsteilen 5 %iger :Salzsäure unter Erwärmen- gelöst, 2 Gewichtsteile Na- triumjodid zugegeben und bei etwa 25 schweflige Säure bis zur Sättigung einge leitet.
Nach einigem Stehen kristallisiert das m,[2,4 - Diamino r 1,3,5-triazinyl-(6) ] -amino- phenylarsinogyd als farbloses Pulver aus. Man saugt ab, wäscht mit Wasser und trock net bei Zimmertemperatur im Vakuum.
Terfaliren for the preparation of m- [2,4-1) iamino-1, 3,5-triazinyl- (6)) -amino-plienylarsine oxide. Organic arsenic compounds play an outstanding role in the treatment of many infectious diseases. In the main, derivatives of phenylarsonic acids and those of arsenobenzene are used to combat these diseases.
Of the derivatives of phenylarsine oxide, only 3-amino-4-oxy-phenyl arsine oxide has been used in therapy so far. This compound has the major disadvantage that it is very sensitive to oxidation. It can therefore not be used in an alkaline solution.
It has now been found that the tria, zinyl-aminophenylarsine oxides, a new class of derivatives of phenylarsine oxide, have particularly valuable therapeutic properties. They are obtained by reducing the corresponding arsonic acids, preferably with sulphurous acid in the presence of hydroiodic acid.
The previously unknown triazinyl-aminophenylarsine oxides are colorless, crystallized compounds that do not have a defined melting point. Si 'Si' easily dissolve in Al- lalia. They are reprecipitated from the alkaline solution by acids.
The compounds have a wide therapeutic range and also have the property, which is particularly important for practical use, of being resistant to oxygen in the air even in alkaline solutions. It is known that the arsine oxides are converted into the alkali salts of arsenic acids by the action of alkali hydroxides with hydration.
The arsine oxides provided according to the invention can be converted into aqueous solution in the form of these arsinic acid salts. Such solutions are air-resistant and are suitable for injection purposes.
The subject of the present patent is a process for the preparation of m- [2,4-diamino -1, 3 "5-triazinyl - (6)] -amino-phenyl arsine oxide, which is characterized in that m - [2, 4 - diamino -1,3,5 - triazinyl - (6)] - -phenylarsonic acid is treated with a reducing agent.
Sulfurous acid in the presence of hydriodic acid is preferably used as the reducing agent.
The previously unknown m- [2,4-diamino-1, 3; 5-triazinyl- (6)] -, aminophenylarsinogyd dissolves in aqueous alkalis with salt formation. The arsine oxide is precipitated again from the clear, colorless solution by adding acids. The compound is intended to be used as a medicine.
<I> Example: </I> 10 parts by weight of m- [2,4-diamino-1,3., 5- triazinyl- (6)] - aminophenylarsonic acid in 2.00 parts by weight of 5%: hydrochloric acid under Dissolve heating, add 2 parts by weight of sodium iodide and introduce sulfurous acid at about 25 to saturation.
After standing for a while, the m, [2,4-diamino r 1,3,5-triazinyl- (6)] -aminophenylarsinogyd crystallizes out as a colorless powder. It is suctioned off, washed with water and dry net at room temperature in a vacuum.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH242529T | 1940-12-10 | ||
| CH240545T | 1940-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH242529A true CH242529A (en) | 1946-05-15 |
Family
ID=25728516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH242529D CH242529A (en) | 1940-12-10 | 1940-12-10 | Process for the preparation of m- (2,4-diamino-1,3,5-triazinyl- (6)) -amino-phenylarsine oxide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH242529A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2684382A1 (en) * | 1991-12-02 | 1993-06-04 | Rhone Merieux | Pure preparations and medicaments of melarsomine dihydrochloride, process for their preparation and intermediates obtained |
| AU700833B2 (en) * | 1991-12-02 | 1999-01-14 | Merial | Medicinal products and pure preparations of melarsomine dihydrochloride, process for obtaining them and intermediate products obtained |
-
1940
- 1940-12-10 CH CH242529D patent/CH242529A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2684382A1 (en) * | 1991-12-02 | 1993-06-04 | Rhone Merieux | Pure preparations and medicaments of melarsomine dihydrochloride, process for their preparation and intermediates obtained |
| GR920100526A (en) * | 1991-12-02 | 1993-08-31 | Rhone Merieux | Medicaments and pure dichlorhydrate melarsomine compounds, method for obtaining them and intermediate receptive products. |
| AU700833B2 (en) * | 1991-12-02 | 1999-01-14 | Merial | Medicinal products and pure preparations of melarsomine dihydrochloride, process for obtaining them and intermediate products obtained |
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