PRODUCTION OF 2-AMINO-4-PYRIDYLMETHYL-6 HYDROXYBENZOTHIAZOLE DERIVATIVE

PURPOSE:To obtain a 2-amino-4-pyridylmethyl-6-hydroxybenzothiazole derivative useful as an agent for preventing and treating diseases for which a lipoxygenase- inhibiting action is effective, by a new method using an amino- pyridylhydroxymethyl-hydroxybenzothazole derivative as a raw material. CONST...

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Hauptverfasser: NISHIMURA HIROSHI, FURUKAWA TAKESHI, KOMATSU TAKEKI, MINAMI NORIO, YAMAGISHI YOJI
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creator NISHIMURA HIROSHI
FURUKAWA TAKESHI
KOMATSU TAKEKI
MINAMI NORIO
YAMAGISHI YOJI
description PURPOSE:To obtain a 2-amino-4-pyridylmethyl-6-hydroxybenzothiazole derivative useful as an agent for preventing and treating diseases for which a lipoxygenase- inhibiting action is effective, by a new method using an amino- pyridylhydroxymethyl-hydroxybenzothazole derivative as a raw material. CONSTITUTION:A 2-amino-4-pyridylhydroxymethyl-6-hydroxybenzothiazole derivative of formula I (R is H, methyl, methoxy; R , R are H, lower alkyl) [e.g. 4-methoxy(3-pyridyl)methyl-6-hydroxy-5,7-dimethyl-2-methylaminobenzoth iazole] is reduced with zinc in acetic acid to obtain the objective compound of formula II. In the reaction, the acetic acid is preferably used in an amount of 1-10 volumes per pt.wt. of the compound of formula I, and the zinc is used in an amount of 2-30 equivalents based on the compound of formula I under refluxing the solvent. The reaction time is usually 6 hrs to 2 days.
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CONSTITUTION:A 2-amino-4-pyridylhydroxymethyl-6-hydroxybenzothiazole derivative of formula I (R is H, methyl, methoxy; R , R are H, lower alkyl) [e.g. 4-methoxy(3-pyridyl)methyl-6-hydroxy-5,7-dimethyl-2-methylaminobenzoth iazole] is reduced with zinc in acetic acid to obtain the objective compound of formula II. In the reaction, the acetic acid is preferably used in an amount of 1-10 volumes per pt.wt. of the compound of formula I, and the zinc is used in an amount of 2-30 equivalents based on the compound of formula I under refluxing the solvent. 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subjects CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
title PRODUCTION OF 2-AMINO-4-PYRIDYLMETHYL-6 HYDROXYBENZOTHIAZOLE DERIVATIVE
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