Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4H-imidazo[1,2-A][1,4]benzodiazepine-4-YL]propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process

US9156842B2 · kind B2 · utility

Assignee

• PAION UK LIMITED · GB

Inventors

• Gary Stuart Tilbrook · Huntingdon, GB
• Andreas Schumacher · Weil am Rhein, DE
• Rene Emmenegger · Basel, CH

Key dates

• Filing date: Sep 15, 2010
• Grant date: Oct 13, 2015
• Expiry date: Feb 4, 2032

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F9/65586
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention concerns a new process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4H-imidazo[1,2-a][1,4]benzodiazepine-4-yl]-propionic acid methyl esteror3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4H-imidazo[1,2-a][1,4]benzodiazepine-4-yl]propionic acid methyl ester benzene sulfonate (P)which comprises reacting 3-[(S)-7-bromo-2-((R and/or S)-2-hydroxy-propylamino)-5-pyridin-2-yl-3H-benzo[e][1,4]diazepin-3-yl]-propionic acid methyl ester of formula (EM)with an oxidizing agent and optionally treating the reaction product under acidic conditions, such as to produce the compound of formula (F) or the compound (P), and new compounds useful as starting material or as intermediate for performing that process.