DEP0051631DA - Process for the preparation of solutions of thiosemicarbazones - Google Patents
Process for the preparation of solutions of thiosemicarbazonesInfo
- Publication number
- DEP0051631DA DEP0051631DA DEP0051631DA DE P0051631D A DEP0051631D A DE P0051631DA DE P0051631D A DEP0051631D A DE P0051631DA
- Authority
- DE
- Germany
- Prior art keywords
- solutions
- thiosemicarbazones
- preparation
- antipyrine
- solution
- 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
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 title claims description 7
- 150000003584 thiosemicarbazones Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 5
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims description 5
- 229960005222 phenazone Drugs 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 9
- 201000008827 tuberculosis Diseases 0.000 description 2
- WFJFGMLKAISFOZ-UHFFFAOYSA-N 1-amino-3-iminourea Chemical compound NN=C(O)N=N WFJFGMLKAISFOZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Dr, Clemens Lütter» Wuppertal Dr. Ernst Oauer, LeverkusenDr, Clemens Lütter »Wuppertal Dr. Ernst Oauer, Leverkusen
Mz/Sn Leverkusen, den 15.JuIi 1949Mz / Sn Leverkusen, June 15, 1949
Verfahren zur Herstellung von Lösungen von ThiosemicarbazonenProcess for the preparation of solutions of thiosemicarbazones
Thiosemicarbazone finden therapeutische "Verwendung, vor allem gegen Tuberkulose. Für die praktische Anwendung wird es oft als störend empfunden, dass sie vielfach nur in wenigen Lösungsmitteln, besonders Säuren oder Alkalien in Lösung zu bringen sind. Leichter lösliche Thiosemicarbazone kann man durch Einführung von löslichmachenden Gruppen, wie Z0B. von Garbonsäure- oder Sulfonsäuregruppen erhalten; hierdurch wird jedoch die therapeutische Wirkung oft beeinträchtigt. Thiosemicarbazones are used therapeutically, especially against tuberculosis. For practical use, it is often found disturbing that they can often only be dissolved in a few solvents, especially acids or alkalis. More easily soluble thiosemicarbazones can be made by introducing solubilizing groups such as 0 received from Garbonsäure- or sulfonic acid; thereby, however, the therapeutic effect is often impaired.
Es wurde gefunden, dass wässrige Antipyrinlösungen brauchbare Lösungsmittel für Thiosemicarbazone darstellen* In der Wärme, z.T. auch noch bei Körpertemperatur, lassen sich Lösungen mit hohem Thiosem: carbazongehalt herstellen. Bei gewöhnlicher Temperatur klar bleibende Lösungen erhält man z.B., wenn man folgende Konzentrationen bei Anwendung einer 50$igen Antipyrinlösung nicht wesentlich überschreitet. It has been found that aqueous antipyrine solutions are useful solvents for thiosemicarbazones. Even at body temperature, solutions with a high thiosem: carbazone content can be produced. Remaining clear at ordinary temperature Solutions are obtained, for example, if the following concentrations are not significantly exceeded when using a 50% antipyrine solution.
4-Acetylaminobenzalthiosemicarbazon ....... 1,9 - 2 $4-Acetylaminobenzalthiosemicarbazone ....... $ 1.9-2
4-Aminobenzalthiosemicarbazon .....».*.. X fo 4-aminobenzalthiosemicarbazone ..... ». * .. X fo
4-Propionylaminobönzalthiosemicarbazon . . . » . 0,5 $ 4-propionylaminobönzalthiosemicarbazone. . . ». $ 0.5
4-Benzoylaminobenzalthiosemicarbazon „.....,., 1 $4-Benzoylaminobenzalthiosemicarbazone ".....,., 1 $
4-Anisalthiosemicarbazon ..... 1 #4-anisalthiosemicarbazone ..... 1 #
4-Allyloxybenzalthiosemicarbazon 1 $4-Allyloxybenzalthiosemicarbazone $ 1
Die Lösungen können durch Erwärmen oder auch z»B. durch Schütteln bei gewöhnlicher Temperatur hergestellt werden.The solutions can be obtained by heating or, for example, be prepared by shaking at ordinary temperature.
Le A 203Le A 203
«=. 2 —«=. 2 -
Das 4-Acetylaminobenzalthiosemicarbazon ist in höherer Konzentration löslich, als die anderen aufgeführten Thiosemicarbazone. Das ist bei dieser bereits in der Tuberkulösebehandlung eingeführten Verbindung von besonderer praktischer Bedeutung. Die Lösung kann mit Wasser verdünnt werden, ohne dass eine Ausfällung stattfindet, was ein weiterer Vorteil für die medizinisöhe Anwendung, z.B. zu Injektionen ist.The 4-acetylaminobenzalthiosemicarbazone is soluble in higher concentrations than the other listed thiosemicarbazones. The is of particular practical importance for this compound, which has already been introduced in the treatment of tuberculosis. The solution can be with Water can be diluted without precipitation taking place, which is a further advantage for medical use, e.g. for injections is.
Versuche mit verschiedenen Konzentrationen von Antipyrinlösung hatten folgendes Ergebnis> Experiments with different concentrations of antipyrine solution had the following result >
Gehalt der AntipyrinlösungContent of the antipyrine solution
50 j 50 y
40 $ 20 $ 40 $ 20 $
Konzentration an 4-Acetylamino· benzalthiosemicarbazonConcentration of 4-acetylamino benzalt thiosemicarbazone
1,9 - 2 01.9 - 2 0
1 # 0,251 # 0.25
Claims (1)
Family
ID=
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