Method for obtaining a pharmaceutically active compound (irbesartan) and its synthesis intermediate

• Main Authors: DALMASES BARJOAN PERE, HUGUET CLOTET JOAN
• Format: Patent
• Language: Chinese; English
• Published: 02.04.2008
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

Preparation (M1) of Irbesartan (I), or its salt involves: coupling 2-butyl-3-(4'-iodobenzyl)-1,3-diazaspiro[4,4]non-1-en-4-one (II) with 2-(1H-tetrazol-5-yl) phenylboronic acid (III) in a solvent medium, in the presence of an organic or inorganic base, forming a salt with the tetrazole ring of (III), at 25 - 150[deg]C, with a palladium catalyst and optionally with ligand, to obtain (I) in the form of an aqueous solution of one its organic- or inorganic-base salts, followed by acidification and recrystallization. Preparation (M1) of Irbesartan (I), or its salt involves: (1) coupling 2-butyl-3-(4'-iodobenzyl)-1,3-diazaspiro[4,4]non-1-en-4-one (II) with 2-(1H-tetrazol-5-yl) phenylboronic acid (III) in a solvent medium selected from an organic polar or aqueous solvent, or a mixture of water and water-miscible solvent or a biphasic system, in the presence of an organic or inorganic base, capable of forming a salt with the tetrazole ring of (III), at 25 - 150[deg]C, with a palladium catalyst and, optionally a ligan