C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 213/61 (2006.01) C07D 213/68 (2006.01) C07D 401/12 (2006.01)
Patent
CA 2405304
The method for obtaining derivatives of [[(pyridil substituted) methyl]thio]benzimidazole (I), where each of R1, R3 and R4, independently of each other, is hydrogen, an alkyl, alkoxy or fluorinated alkoxy of 1 to 6 carbon atoms, and R2 is nitro, halogen, alkoxy or halogenated alkoxy of 1 to 6 carbon atoms, or a group -O-(CH2)n-OR8, where n is an integer between 1 and 6 and R8 represents hydrogen or an alkyl group with 1 to 6 carbon atoms, which involves (a) reacting an N-oxide of a methylpyridine with an anhydride of activated carboxylic acid or of sulfonic acid, and (b) reacting the intermediate formed in stage (a) with a corresponding mercaptobenzimidazole. The compounds (I) are useful in the synthesis of derivatives of [[(pyridil substituted) methyl] sulfinyl]benzimidazole, such as omeprazol, lansoprazol, rabeprazol or pantoprazol. (see formula I)
L'invention concerne un procédé permettant d'obtenir des dérivés de [[(pyridil substitué)méthyl]thio]benzimidazole (I), dans lequel R¿1?, R¿3? et R¿4?, représentent chacun indépendamment, hydrogène, alkyle, alcoxy ou alcoxy fluoré contenant entre 1 et 6 atomes de carbone, et R¿2? représente nitro, halogène, alcoxy ou alcoxy halogéné contenant entre 1 à 6 atomes de carbone ou un groupe -O-(CH¿2?)¿n?-OR¿8?, dans lequel n vaut un entier compris entre 1 et 6 et R¿8? représente hydrogène ou un groupe alkyle contenant entre 1 et 6 atomes de carbone. Ce procédé consiste (a) à faire réagir un N-oxyde d'une méthylpyridine avec un anhydride d'acide carboxylique activé ou d'acide sulfonique, et (b) à faire réagir l'intermédiaire formé dans l'étape (a) avec un mercaptobenzimidazole correspondant. Les composés selon l'invention (I) conviennent pour synthétiser des dérivés de [[(pyridil substitué)méthyl]thio]benzimidazole, tels que l'oméprazole, le lansoprazole, le rabeprazole ou le pantoprazole.
Berenguer Maimo Ramon
Coppi Laura
Esteve Quimica S.a.
Sim & Mcburney
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