Ethyl ester of 6-bromo-5-hydroxy-4-dimethylaminomethyl-1 methyl-2-phenylthiomethylindole-3-carboxylic acid hydrochloride monohydrate, process for obtaining it and drug with antiviral, interferon-inducing and immunomodulant activity based thereon

Ethyl ester of 6-bromo-5-hydroxy-4-dimethylaminomethyl-1 methyl-2-phenylthiomethylindole-3-carboxylic acid hydrochloride monohydrate, process for obtaining it and drug with antiviral, interferon-inducing and immunomodulant activity based thereon

The new compound, namely the ethyl ester of 6-bromo-5 hydroxy-4-dimethylaminomethyl-1-methyl-2 phenylthiomethylindole-3-carboxylic acid hydrochloride monohydrate, has the following formula: The process for the preparation of the claimed substance consists in that the ethyl ester of 5-acetoxy-1,2 dim...

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Hauptverfasser: SAVINA ELENA PETROVNA, PERSHIN GRIGORY NIKOLAEVICH, SAFONOVA LJUDMILA SERGEEVNA, KUTCHAK SVETLANA NIKOLAEVNA, ZOTOVA SVETLANA ALEXEEVNA, KARPOVA NINA ALEXEEVNA, YDROVSKAYA VERA ALEXANDROVNA, KONOPLYANNIKOV ANATOLY GEORGIEVCH, TROFIMOV FEDOR ALEXANDROVICH, TSYSHKOVA NINA GAVRILOVNA, SVIRINA EVGENIA ALEXANDROVNA, SURINOV BORIS PAVLOVICH, FOMINA ALLA NIKOLAEVNA, BOGDANOVA NADEZHDA SERGEEVNA, KUBAR OLGA IOSIFVNJA, SHVETSOVA EVGENIA GEORGIEVNA, NIKOLAEVA IRINA SERGEEVNA, ZLYDNIKOV DMITRY MIKHAILOVICH, PADEISKAYA ELENA NIKOLAEVNA, GRINEV ALEXEI NIKOLAEVICH, SAKHASCHIK ZINAIDA MIKHAILOVNA, SAVINOVA LJUDMILA ALEXEEVNA, BRYANTSEVA ELENA ALEXEEVNA, PETERS VALENTINA VASILIEVNA
Format: Patent
Sprache:eng ; ita
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CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
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Zusammenfassung:The new compound, namely the ethyl ester of 6-bromo-5 hydroxy-4-dimethylaminomethyl-1-methyl-2 phenylthiomethylindole-3-carboxylic acid hydrochloride monohydrate, has the following formula: The process for the preparation of the claimed substance consists in that the ethyl ester of 5-acetoxy-1,2 dimethylindole-3-carboxylic acid is treated with a brominating agent in an inert organic solvent with boiling, the ethyl ester of 5-acetoxy-6-bromo-2 bromomethyl-1-methylindole-3-carboxylic acid formed is reacted with thiophenol in the presence of alkaline hydroxide or of its alcoholate in an organic solvent, and the ethyl ester of 6-bromo-5-hydroxy-1-methyl-2 phenylthiomethylindole-3-carboxylic acid obtained is reacted with an aminomethylating agent in an organic solvent at a temperature of 65 degree C up to the boiling point of the reaction mixture. Next the finished product is separated from the base formed, i.e. from the ethyl ester of 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2 phenylthiomethylindole-3-carboxylic acid. The claimed substance is the active principle of a drug with antiviral, interferon-inducing and immunomodulating action.