CH293300A - Process for the production of a thiosemicarbazone. - Google Patents
Process for the production of a thiosemicarbazone.Info
- Publication number
- CH293300A CH293300A CH293300DA CH293300A CH 293300 A CH293300 A CH 293300A CH 293300D A CH293300D A CH 293300DA CH 293300 A CH293300 A CH 293300A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- phenoxy
- thiosemicarbazone
- substituents
- benzalthiosemicarbazone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 title 1
- QWLHJVDRPZNVBS-UHFFFAOYSA-N 4-phenoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OC1=CC=CC=C1 QWLHJVDRPZNVBS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical group 0.000 claims description 3
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- -1 aeyloxy Chemical group 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 201000008827 tuberculosis Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Thiosemicarhazons. 1's wurde gefunden, dass die 0-Pheni-l- deriva.te von Oxybenzalthiosemicarbazonen sieh durch besonders intensive Wirkung gegen Tuberkulose auszeichnen und verhältnismässig 1.ut verträglich sind.
Zweckmässig kann dabei der Benzolkern des Phenoxyrestes durch Substituenten be setzt sein, welche die therapeutische Wirkuno- erhöben, wie z. B.
Halogene, ()xy-, Alkoxy-, Aryloxy-, Aeyloxy-, Amino-, Aeylamino-, Alkylamino-, Alkylmercapto-, Alkylsulfon-, Carboxyl-, Carboxylalkyl-, Nitro- und andere Gruppen. Die Substituenten können einmal oder mehrmals, auch kombiniert, auftreten.
Solche Substituenten können auch in dem Benzolkern der Oxybenzaldehydreste, bei denen die Oxygruppe in o-, in- oder p-Stel- lung zum Aldehydrest stehen kann, enthalten sein. Doch können auch Phenoxybenzalthio- semicarbazone, welche die aufgeführten Sub- stituenten nicht haben, starke Wirkungen ent falten. Die Verbindungen zeichnen sieh ausser ihrer Wirkung gegen Tuberkulose und Lepra durch starke entzündungshemmende Wirkung aus.
Czegenstand des vorliegenden Patentes ist. nun ein Verfahren zur Herstellung von 4 - Phenoxy - benzalthiosemicarbazon, das da durch gekennzeichnet ist, dass man 4-Phenoxy- benzaldehyd mit Thiosemicarbazid umsetzt.. Die Verbindung soll als Arzneimittel Verwen dung finden.
Beispiel: 39,6 g 4-Phenoxy-benzaldehyd werden in 240 cm3 Methanol gelöst und mit einer heissen Lösung von 18,2 g Thiosemicarbazid in 90 em3 Wasser versetzt. Die Mischung wird, zweck mässig nach Hinzufügung einiger Tropfen Eisessig, am Rückfluss gekocht. Nach Beendi gung der Umsetzung wird abgekühlt und der Niederschlag abgesaugt. Das entstandene 4-Phenoxy-benzalthiosemicarbazon bildet farb lose Kristalle vom Schmelzpunkt 142 , die aus Alkohol umgelöst werden können.
Process for the production of a thiosemicarhazone. It was found that the O-Pheni-deriva.te of Oxybenzalthiosemicarbazonen are characterized by a particularly intensive action against tuberculosis and are relatively well tolerated.
The benzene nucleus of the phenoxy radical can expediently be set by substituents which increase the therapeutic effect, such as. B.
Halogens, () xy, alkoxy, aryloxy, aeyloxy, amino, aeylamino, alkylamino, alkylmercapto, alkylsulfone, carboxyl, carboxylalkyl, nitro and other groups. The substituents can occur once or several times, also in combination.
Such substituents can also be contained in the benzene nucleus of the oxybenzaldehyde radicals, in which the oxy group can be in the o, in or p position to the aldehyde radical. However, phenoxybenzalthiosemicarbazones, which do not have the listed substituents, can also develop strong effects. In addition to their action against tuberculosis and leprosy, the compounds are characterized by a strong anti-inflammatory effect.
The subject of the present patent is. now a process for the production of 4-phenoxy-benzalthiosemicarbazone, which is characterized by the fact that 4-phenoxybenzaldehyde is reacted with thiosemicarbazide. The compound is said to be used as a medicament.
Example: 39.6 g of 4-phenoxy-benzaldehyde are dissolved in 240 cm3 of methanol and a hot solution of 18.2 g of thiosemicarbazide in 90 cubic meters of water is added. The mixture is refluxed, expediently after adding a few drops of glacial acetic acid. After the end of the reaction, the mixture is cooled and the precipitate is filtered off with suction. The resulting 4-phenoxy-benzalthiosemicarbazone forms colorless crystals with a melting point of 142, which can be redissolved from alcohol.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE293300X | 1950-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH293300A true CH293300A (en) | 1953-09-15 |
Family
ID=6078477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH293300D CH293300A (en) | 1950-03-27 | 1951-02-05 | Process for the production of a thiosemicarbazone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH293300A (en) |
-
1951
- 1951-02-05 CH CH293300D patent/CH293300A/en unknown
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