Alfuzosin hydrochloride, SL-77499(free base), SL-7749910, Xatral OD, Xatral Retard, Xatral XL, Xatral SR, Alfetim, Uroxatral, Urion, Alfoten, Xatral

盐酸阿夫唑嗪 阿夫唑嗪 Chemical Name: (?-N-[3-[(4-Amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamide monohydrochloride; (?-N-[3-[(4-Amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furamide monohydrochloride
CAS No. 81403-68-1, 81403-80-7 (free base)
项目整合开发状态: Launched-1988
项目研究机构: Sanofi-Aventis (Originator), Altana Pharma (Licensee), Lorex (Licensee)
合成路线:Title compound can be prepared as follows:1) 6,7-Dimethoxyquinazolin-2,4-dione (I) is converted to 2,4-dichloro 6,7-dimethoxyquinazoline (II),followed by selective displacement of the 4-chloro group with ammonia to give 4-amino-2-chloro-6,7-dimethoxyquinazoline (III).2) 3-(Methylamino)propanenitrile (IV) is reacted with the mixed anhydride obtained from tetrahydrofuran-2-carboxylic acid and ethyl chloroformate to form the amide (V),which on hydrogenation over rhodium at 80 C in the presence of ammonia affords the required secondary amine (VI) via rearrangement of the initially formed primary amine (VII).Condensation of amine (VI) with 4-amino-2-chloro-6,7-dimethoxyquinazoline (III) in refluxing amyl alcohol gives alfuzosin hydrochloride.