Enantioselective synthesis of 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one and zilpaterol

US8629134B2 · kind B2 · utility

Assignee

• INTERVET INTERNATIONAL B.V · NL

Inventors

• Juan Jose Almena-Perea · Hanau, DE
• Monika Brink · Ingelheim am Rhein, DE
• Gerhard Geiβ · Hanau, DE
• Renat Kadyrov · Rostock, DE
• Thorsten Meyer · Bad Kreuznach, DE

Key dates

• Filing date: Jan 31, 2008
• Grant date: Jan 14, 2014
• Expiry date: Dec 15, 2029

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P43/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

This invention relates to a process for the hydrogenation of a ketooxime to selectively form an aminoalcohol stereoisomer, and, in particular, to a process for the hydrogenation of 4,5-dihydro-imidazo[4,5,1-jk][1]benzazepin-2,6,7[1H]-trione-6-oxime or a salt thereof to selectively form a stereoisomer of 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one or a salt thereof. This invention also relates to the use of the 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one hydrogenation product or a salt thereof to selectively make a stereoisomer of zilpaterol or a salt thereof, as well as the use of such a zilpaterol stereoisomer or salt in methods of treatment and medicaments for animals.