CH208081A - Process for the preparation of phenylglycidomethylglucamide-p-arsic acid. - Google Patents
Process for the preparation of phenylglycidomethylglucamide-p-arsic acid.Info
- Publication number
- CH208081A CH208081A CH208081DA CH208081A CH 208081 A CH208081 A CH 208081A CH 208081D A CH208081D A CH 208081DA CH 208081 A CH208081 A CH 208081A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- phenylglycidomethylglucamide
- preparation
- glucamide
- water
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- XKNKHVGWJDPIRJ-UHFFFAOYSA-N arsanilic acid Chemical compound NC1=CC=C([As](O)(O)=O)C=C1 XKNKHVGWJDPIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 229950002705 arsanilic acid Drugs 0.000 claims description 3
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 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
- 125000003277 amino group Chemical group 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
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940093920 gynecological arsenic compound Drugs 0.000 description 1
- -1 methylglucamine chlorohydrate Chemical compound 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 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
- C07F9/90—Antimony compounds
- C07F9/92—Aromatic compounds
-
- 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
Verfahren zur Herstellung von Phenylglycidmethylglukamid-p-arsinsäur e. Aromatische Arsen- und Antimonver- bindungen, welche einen Rest mit mehreren Hydroxylgruppen enthalten, sind bekannt. In diesen Verbindungen befindet sich der die Hydroxylgruppen tragende Alkylrest an einer aromatisch gebundenen Aminogruppe. Eine praktische Bedeutung haben diese Verbin dungen nicht gezeigt.
Es wurde nun gefunden, dass die Phenyl- glycidmethylglukamid-p-arsinsäure sich durch einen besonders günstigen chemotherapeu tischen Index auszeichnet. Man erhält diese Verbindung, indem man Arsanilsäure mit N-Halogenacetyl-N methylglukamid, beispiels weise mit Chloracetylmethyl-glukamid, in al kalischem Medium, beispielsweise in verdünn ter Natronlauge, umsetzt.
Die neue Verbindung stellt ein in Wasser leicht lösliches weisses Pulver dar; sie soll für chemotherapeutische Zwecke Verwendung finden. <I>Beispiel:</I> 21 g Arsanilsäure, die in 50 eins Wasser und 50 cms 2n-Natronlauge gelöst werden, werden mit 27 g N-Chloracetyl-N-methyl- glukamid etwa 2 Stunden auf dem Dampf bad erhitzt. Nach dem Abkühlen wird klar filtriert und in etwa 1 Liter absoluten Al kohol unter Rübren einlaufen gelassen. Das ausgefällte, fast weisse Pulver wird abgesaugt, dann in 40 cm' Wasser gelöst, filtriert und mehrere Stunden y m Eisschrank stehen ge lassen.
Man filtriert wieder klar und fällt mit Methylalkohol. Man erhält die Phenyl- glyeidmethyl-glukamid-p-arsinsäure als wei sses in Wasser leicht lösliches Pulver. Das Produkt besitzt die Formel
EMI0001.0024
Durch Reduktion der Phenylglycidmethyl- glukamid-p-arsinsäure mit Hypophoaphit bezw. Sulfit erhält man das Di-p-methyl- glukamidglycidarsenobenzol als ein in Wasser leicht lösliches hellgelbes Pulver, das sich durch Lösen in Wasser und Fällen mit Me thylalkohol leicht rein erhalten lässt.
Das N-Chloracetyl-N-methyl-glukamid wird folgendermassen erhalten 39 g N-Methyl-glukamin werden in 50 cm" Wasser gelöst und unter Kühlung 11,6 g Chloracetylchlorid zugesetzt. Es wird so lange geschüttelt, bis der Geruch des Chloracetyl- chlorids verschwunden ist. Dann wird im Vakuum zur Trockne gebracht und der Rück stand mit 200 cms Methylalkohol versetzt. Beim Abkühlen kristallisiert das Methyl- glukaminehlorhydrat aus. Man saugt ab und engt das Filtrat, welches das N-Chloracetyl- N-methyl-glukamid enthält, im Vakuum ein.
Process for the preparation of Phenylglycidmethylglukamid-p-arsinsäur e. Aromatic arsenic and antimony compounds which contain a radical with several hydroxyl groups are known. In these compounds, the alkyl radical carrying the hydroxyl groups is located on an aromatically bound amino group. These connections have not shown any practical significance.
It has now been found that phenylglycidomethylglucamide-p-arsic acid is characterized by a particularly favorable chemotherapeutic index. This compound is obtained by reacting arsanilic acid with N-haloacetyl-N methylglucamide, for example with chloroacetylmethylglucamide, in an alkaline medium, for example in dilute sodium hydroxide solution.
The new compound is a white powder that is easily soluble in water; it should be used for chemotherapeutic purposes. <I> Example: </I> 21 g of arsanilic acid, which are dissolved in 50 units of water and 50 cms of 2N sodium hydroxide solution, are heated with 27 g of N-chloroacetyl-N-methyl-glucamide on a steam bath for about 2 hours. After cooling, the mixture is filtered clear and poured into about 1 liter of absolute alcohol while stirring. The precipitated, almost white powder is filtered off with suction, then dissolved in 40 cm 'of water, filtered and left to stand in the refrigerator for several hours.
It is filtered clear again and precipitated with methyl alcohol. The phenylglyeide methyl-glucamide-p-arsic acid is obtained as a white powder which is readily soluble in water. The product has the formula
EMI0001.0024
By reducing the phenylglycidmethyl glucamide-p-arsinic acid with hypophoaphite or. Sulphite, the di-p-methylglucamide glycidarsenobenzene is obtained as a light yellow powder which is easily soluble in water and which can easily be obtained in pure form by dissolving in water and precipitating with methyl alcohol.
The N-chloroacetyl-N-methyl-glucamide is obtained as follows: 39 g of N-methyl-glucamine are dissolved in 50 cm "of water and 11.6 g of chloroacetyl chloride are added with cooling. The mixture is shaken until the odor of the chloroacetyl chloride It is then brought to dryness in vacuo and 200 cms of methyl alcohol are added to the residue. On cooling, the methylglucamine chlorohydrate crystallizes out. The filtrate, which contains the N-chloroacetyl-N-methyl-glucamide, is filtered off with suction and concentrated. in a vacuum.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE223019X | 1935-11-09 | ||
| DE208081X | 1935-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH208081A true CH208081A (en) | 1939-12-31 |
Family
ID=33030518
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH223019D CH223019A (en) | 1935-11-09 | 1936-11-03 | Process for the preparation of phenylglycidomethylglucamide-p-stibic acid. |
| CH208081D CH208081A (en) | 1935-11-09 | 1936-11-03 | Process for the preparation of phenylglycidomethylglucamide-p-arsic acid. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH223019D CH223019A (en) | 1935-11-09 | 1936-11-03 | Process for the preparation of phenylglycidomethylglucamide-p-stibic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH223019A (en) |
-
1936
- 1936-11-03 CH CH223019D patent/CH223019A/en unknown
- 1936-11-03 CH CH208081D patent/CH208081A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH223019A (en) | 1942-08-15 |
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