DE235391C - - Google Patents
Info
- Publication number
- DE235391C DE235391C DENDAT235391D DE235391DA DE235391C DE 235391 C DE235391 C DE 235391C DE NDAT235391 D DENDAT235391 D DE NDAT235391D DE 235391D A DE235391D A DE 235391DA DE 235391 C DE235391 C DE 235391C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- acids
- oxyarylarsinic
- reducing agents
- weak reducing
- 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
- 239000002253 acid Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
- 229940067157 phenylhydrazine Drugs 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910000413 arsenic oxide Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- -1 aminooxyphenyl arsenic Chemical compound 0.000 description 2
- 229960002594 arsenic trioxide Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- AUVSZLMLDDURTR-UHFFFAOYSA-N NO[As](=O)c1ccccc1 Chemical compound NO[As](=O)c1ccccc1 AUVSZLMLDDURTR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- JDMNJTLOJXRGHG-UHFFFAOYSA-N aminooxy(phenyl)arsinic acid Chemical compound NO[As](O)(=O)C1=CC=CC=C1 JDMNJTLOJXRGHG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Nach dem Verfahren des Hauptpatents 213594 gelangt man zu therapeutisch wertvollen Verbindungen, wenn man Oxyarylarsinsäuren mit schwachen Reduktionsmitteln behandelt, wobei Oxyarylarsenoxyde erhalten werden.Following the procedure of the main patent 213594 one arrives at therapeutically valuable ones Compounds when treating oxyarylarsinic acids with weak reducing agents, whereby oxyaryl arsenic oxides are obtained.
Es hat sich nun gezeigt, daß die therapeutische Wirksamkeit dieser Verbindungen durch Einführung von Aminogruppen in den Benzolkern bedeutend gesteigert werden kann; zu solchen Aminooxyarylarsenoxyden gelangt man durch Behandlung von Aminoderivaten der Oxyarylarsinsäuren mit schwachen Reduktionsmitteln. It has now been shown that the therapeutic effectiveness of these compounds can be increased significantly by introducing amino groups into the benzene nucleus; Such aminooxyaryl arsenic oxides are obtained by treating amino derivatives of oxyarylarsinic acids with weak reducing agents.
Aminooxyphenylarsenoxyd: 234 g Aminooxyphenylarsinsäure, deren Darstellung im Patent 224953, Kl. 12 q, beschrieben wurde, werden in i,5 1 Wasser und 1,3 1 verdünnter Schwefelsäure (1: 5) gelöst. Man fügt 50 g Jodkalium hinzu und sättigt bei gewöhnlicher Temperatur mit schwefliger Säure. Nun versetzt man unter gelindem Rühren und starker Kühlung mit konzentriertem wässerigen Ammoniak bis zur stark alkalischen Reaktion. Sobald die Säure abgestumpft ist, scheidet sich das Aminooxyphenylarsenoxyd als mikrokristallinischer, fast weißer Niederschlag ab; zur Vervollständigung der Fällung trägt man noch ι kg Kochsalz ein, saugt darauf ab, wäscht mehrmals mit gesättigter Kochsalzlösung nach und trocknet im Vakuum über Schwefelsäure. Aminooxyphenylarsenoxide: 234 g of aminooxyphenylarsinic acid, the representation of which was described in patent 224953, cl. 12 q in 1.5 liters of water and 1.3 liters of dilute sulfuric acid (1: 5) solved. Add 50 g of potassium iodide and saturate at ordinary temperature with sulphurous acid. The mixture is then added with gentle stirring and vigorous cooling with concentrated aqueous ammonia to a strongly alkaline reaction. As soon as the Acid is blunted, the aminooxyphenyl arsenic oxide separates as a microcrystalline, almost white precipitate from; to complete the precipitation one still carries ι kg of sodium chloride, sucks on it, washes several times with saturated sodium chloride solution after and dried in vacuo over sulfuric acid.
Aminooxyphenylarsenoxyd ist in Wasser ziemlich löslich, sehr leicht in wässerigen Mineralsäuren und in Natronlauge sowie in Methylalkohol, wenig löslich in Äther, unlöslich in Benzol.Aminooxyphenyl arsenic oxide is quite soluble in water, very easily in aqueous ones Mineral acids and in caustic soda as well as in methyl alcohol, slightly soluble in ether, insoluble in benzene.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB190809855T | 1908-05-06 | ||
| DE191024480X | 1909-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE235391C true DE235391C (en) | 1911-06-10 |
Family
ID=32852099
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT213594D Expired DE213594C (en) | 1908-05-06 | ||
| DENDAT235391D Expired DE235391C (en) | 1908-05-06 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT213594D Expired DE213594C (en) | 1908-05-06 |
Country Status (2)
| Country | Link |
|---|---|
| DE (2) | DE235391C (en) |
| GB (1) | GB191024480A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476508A (en) * | 1942-08-31 | 1949-07-19 | Abbott Lab | Syphilotherapy agent |
-
0
- DE DENDAT213594D patent/DE213594C/de not_active Expired
- DE DENDAT235391D patent/DE235391C/de not_active Expired
-
1910
- 1910-10-21 GB GB191024480D patent/GB191024480A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE213594C (en) | 1900-01-01 |
| GB191024480A (en) | 1910-12-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE235391C (en) | ||
| DE1443064A1 (en) | Method of Obtaining Acrylamide | |
| DE3039997A1 (en) | PHOSPHONOHYDROXYACETONITRILE, A METHOD FOR THE PRODUCTION THEREOF AND ITS USE AS AN INTERMEDIATE PRODUCT FOR THE PRODUCTION OF MEDICINAL PRODUCTS | |
| DE1617463A1 (en) | Process for the manufacture of injectable colloidal iron preparations | |
| DE703103C (en) | indications from keratin breakdown products | |
| DE694100C (en) | Process for the production of metal compounds | |
| AT34249B (en) | Process for the preparation of 2.4.6-trioxypyrimidine and its 5-mono- and dialkyl derivatives. | |
| AT102313B (en) | Process for the representation of complex gold compounds. | |
| DE1174773B (en) | Process for the production of ª ‰, ª ‰ '- dihydroxydiaethylsulfon and ª ‰ -hydroxyaethanesulfonates | |
| AT105092B (en) | Process for the preparation of symmetrical ureas of p-oxy-m-aminophenylarsinic acid and its aminoazidyl derivatives. | |
| DE964496C (en) | Process for the recovery of the excess formaldehyde and nitric acid obtained in the manufacture of cyclotrimethylene trinitramine | |
| DE488891C (en) | Process for the preparation of N-substituted arsenobenzimidazolones | |
| DE638265C (en) | Process for the preparation of arsenobenzene monosulfoxylates | |
| DE458189C (en) | Production of hydrogen peroxide | |
| DE682663C (en) | Process for the production of a preparation from yeast | |
| DE902848C (en) | Process for the production of ª-oxybutyrolactone | |
| DE853167C (en) | Process for the preparation of pyrrolidine-acylaminobenzolar compounds | |
| DE944953C (en) | Process for the preparation of a therapeutic agent consisting of the calcium salt of Ca-ethylene diamine tetraacetic acid | |
| DE802636C (en) | Process for the preparation of glycosides of sulfanilamide | |
| DE555241C (en) | Process for the preparation of amino-substituted guaiacolar acids and their reduction products | |
| DE164323C (en) | ||
| AT112126B (en) | Process for the preparation of derivatives of cyclic aminometal mercapto compounds. | |
| DE261875C (en) | ||
| DE509515C (en) | Process for processing zirconia lime products | |
| DE442596C (en) | Process for the production of iron-free aluminum sulfate from alum |