C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 209/88 (2006.01) C07C 69/96 (2006.01) C07C 271/16 (2006.01) C07D 263/20 (2006.01) C07D 413/12 (2006.01)
Patent
CA 2407103
1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxy-phenoxy)-ethylamino]-propan-2-ol, carvedilol, or an acid addition salt thereof, is prepared by alkylating 5- chloromethyl-3-[2-(2-methoxy-phenoxy)-ethyl]-oxazolidin-2-one (VII) with 4- hydroxy-carbazol for the formation of 5-(9H-carbazol-4-yloxymethyl)-3-[2-(2- methoxy-phenoxy)-ethyl]-oxazolidin-2-one (IX), or an acid addition salt thereof, which subsequently is decarboxylated. The compound (VII) may be formed in a two step reaction starting from 1,3-dichloro-propan-2-ol, phenyl chloroformate and 2-(2-methoxy-phenoxy)-ethylamine followed by formation of the oxazolidine ring by cyclisation. Further new intermediates for the synthesis of carvedilol are provided.
Selon l'invention, le 1-(9H-carbazol-4-yloxy)-3-[2-(2-méthoxy-phénoxy)-éthylamino]-propane-2-ol, carvedilol, ou un sel d'addition acide de ce composé, est préparé par alkylation de 5-chlorométhyl-3-[2-(2-méthoxy-phénoxy)-éthyl]-oxazolidine-2-one (VII) avec du 4-hydroxy-carbazol pour la formation de 5-(9H-carbazol-4-yloxyméthyl)-3-[2-(2-méthoxy-phénoxy)-éthyl]-oxazolidine-2-one (IX), ou d'un sel d'addition acide de ce composé, décarboxylé par la suite. Le composé (VII) peut être formé au cours d'une réaction en deux étapes partant de 1,3-dichloro-propane-2-ol, phényl chloroformate et de 2-(2-méthoxy-phénoxy)-éthylamine, suivie par formation du cycle oxazolidine par cyclisation. L'invention concerne par ailleurs de nouveaux intermédiaires pour la sysnthèse de carvedilol.
Fischer Erik
Pittelkow Thomas
Treppendahl Svend Peter
A/s Gea Farmaceutisk Fabrik
Gowling Lafleur Henderson Llp
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