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1. (WO2001087837) PROCESS AND INTERMEDIATES FOR THE PREPARATION OF 1-(9H-CARBAZOL-4-YLOXY)-3-[2-(2-METHOXY-PHENOXY)-ETHYLAMINO]-PROPAN-2-OL, CARVEDILOL OR ACID ADDITION SALTS THEREOF
Latest bibliographic data on file with the International Bureau   

Pub. No.:    WO/2001/087837    International Application No.:    PCT/DK2001/000306
Publication Date: 22.11.2001 International Filing Date: 03.05.2001
Chapter 2 Demand Filed:    02.11.2001    
IPC:
C07C 69/96 (2006.01), C07C 271/16 (2006.01), C07D 209/88 (2006.01), C07D 263/20 (2006.01), C07D 413/12 (2006.01)
Applicants: A/S GEA FARMACEUTISK FABRIK [DK/DK]; Holger Danskes Vej 89, DK-2000 Frederiksberg (DK)
Inventors: PITTELKOW, Thomas; (DK).
FISCHER, Erik; (DK).
TREPPENDAHL, Svend, Peter; (DK)
Agent: SIMONSEN, Christian, Rosendal; Internationalt Patent-Bureau, Høje Taastrup Boulevard 23, DK-2630 Taastrup (DK)
Priority Data:
PA 2000 00801 18.05.2000 DK
Title (EN) PROCESS AND INTERMEDIATES FOR THE PREPARATION OF 1-(9H-CARBAZOL-4-YLOXY)-3-[2-(2-METHOXY-PHENOXY)-ETHYLAMINO]-PROPAN-2-OL, CARVEDILOL OR ACID ADDITION SALTS THEREOF
(FR) PROCEDE ET INTERMEDIAIRES DESTINES A LA PREPARATION DE 1-(9H-CARBAZOL-4-YLOXY)-3-[2-(2-METHOXY-PHENOXY)-ETHYLAMINO]-PROPANE-2-OL, CARVEDILOL OU D'UN SEL D'ADDITION ACIDE DE CE COMPOSE
Abstract: front page image
(EN)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.
(FR)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.
Designated States: CA, NO.
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR).
Publication Language: English (EN)
Filing Language: English (EN)