Process for the preparation of indolone derivative

C - Chemistry – Metallurgy – 07 – D

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C07D 207/26 (2006.01)

Patent

CA 2597791

A process for the preparation of 4-[2-(Di-n-propylamino) ethyl]-2,3-dihydro-1 H-indol-2-one of formula (I) and its pharmaceutically acceptable salts, solvates Formaula I involving new intermediates of compound of formula (A) and (B) wherein R represents (i) a halogen atom selected from fluorine, chlorine atom, bromine atom and iodine atom; (ii) lower alkanesulfonyloxy group selected from methanesulfonyloxy, ethanesulfonyloxy, isopropanesulfonyloxy, propanesulfonyloxy, butanesulfonyloxy, tert-butanesulfonyloxy, pentanesulfonyloxy, hexanesulfonyloxy; (iii) substituted or unsubstantiated arylsulfonyloxy group selected from phenylsulfonyloxy, 4- methylphenylsulfonyloxy, 2-methylphenylsulfonyloxy, 4- nitrophenylsulfonyloxy, 4- methoxyphenylsulfonyloxy, 3-chlorophenylsulfonyloxy; (iv) arylalkylsulfonyloxy group selected from benzylsulfonyloxy, 2- phenylethylsulfonyloxy, 4-phenylbutylsulfonyloxy, 4- methylbenzylsulfonyloxy, 2- methylbenzylsulfonyloxy, 4- nitrobenzylsulfonyloxy, 4- methoxybenzylsulfonyloxy, 3- chlorobenzylsulfonyloxy.

L'invention concerne un procédé de préparation d'une 4-[2-(Di-n-propylamino) éthyl]-2,3-dihydro-1 H-indol-2-one de la formule (I) et de ses sels et solvates pharmaceutiquement acceptables, dans lequel sont utilisés de nouveaux intermédiaires du composé de la formule (A) et de la formule (B), où R représente (i) un atome d'halogène choisi entre le fluor, un atome de chlore, un atome de brome et un atome d'iode; (ii) un groupe alkanesulfonyloxy inférieur choisi entre le méthanesulfonyloxy, l'éthanesulfonyloxy, l'isopropanesulfonyloxy, le propanesulfonyloxy,le butanesulfonyloxy, le tert-butanesulfonyloxy, le pentanesulfonyloxy, l'hexanesulfonyloxy; (iii) un groupe arylsulfonyloxy substitué ou non substitué choisi entre le phénylsulfonyloxy, le 4-méthylphénylsulfonyloxy, le 2-méthylphénylsulfonyloxy, le 4-nitrophénylsulfonyloxy, le 4-méthoxyphénylsulfonyloxy, le 3-chlorophénylsulfonyloxy; (iv) un groupe arylalkylsulfonyloxy choisi entre le benzylsulfonyloxy, le 2-phényléthylsulfonyloxy, le 4-phénylbutylsulfonyloxy, le 4-méthylbenzylsulfonyloxy, le 2-méthylbenzylsulfonyloxy, le 4-nitrobenzylsulfonyloxy, le 4-méthoxybenzylsulfonyloxy, le 3-chlorobenzylsulfonyloxy.

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