Chemical process for manufacturing monobactam antibiotic and intermediates thereof

US11414411B2 · kind B2 · utility

Assignee

• Novartis AG · CH

Inventors

• Like Chen · Hoherlehmer Straße, CN
• Chi Ming Cheung · Hoherlehmer Straße, CN
• Zhongbo Fei · Hoherlehmer Straße, CN
• Qun Jiang
• Lei Li · Zhengzhou, CN
• Bin Li · Columbus, US
• Thomas Ruch · Frenkendorf, CH
• Hao Wang · Beijing, CN
• Quanbing Wu · Hoherlehmer Straße, CN

Key dates

• Filing date: Aug 1, 2018
• Grant date: Aug 16, 2022
• Expiry date: Aug 1, 2038

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides a process of synthesizing 1-(((Z)-(1-(2-aminothiazol-4-yl)-2-oxo-2-(((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)-1-sulfoazetidin-3 yl)amino)ethylidene)amino)oxy)cyclopropanecarboxylic acid (referred to herein as Compound X), or a salt thereof, or a solvate including hydrate thereof, and/or intermediates thereof, and the use of intermediates for preparing Compound X. In particular, the process relates to the preparation of Compound X using dynamic kinetic resolution (DKR) and asymmetric catalytic reduction, thereby providing an improved route to 1-(((Z)-(1-(2-aminothiazol-4-yl)-2-oxo-2-(((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)-1-sulfoazetidin-3 yl)amino)ethylidene)amino)oxy)cyclopropanecarboxylic acid (Compound X) and compositions containing said compound, including the arginine salt, sodium salt and hydrated solid forms of Compound X.