Methods of synthesizing a prostacyclin analog

US10450257B2 · kind B2 · utility

Assignee

• CAYMAN CHEMICAL COMPANY, INC. · US

Inventors

• Kirk William Hering · Salem, US
• Gilles Chambournier · Ann Arbor, US
• Gregory William Endres · Saline, US
• Victor Fedij · Brighton, US
• Thomas James Krell, II · Wolfsburg, DE
• Hussein Mahmoud Mahmoud · Ann Arbor, US

Key dates

• Filing date: Jan 18, 2018
• Grant date: Oct 22, 2019
• Expiry date: Jan 18, 2038

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/14
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides processes for preparing a prostacyclin analog of Formula I or a pharmaceutically acceptable salt thereof, wherein R10 is a linear or branched C1-6 alkyl. The processes of the present invention comprise steps that generate improved yields and fewer byproducts than traditional methods. The processes of the present invention employ reagents (e.g., the oxidizing reagent) that are less toxic that those used in the traditional methods (e.g., oxalyl chloride). Many of the processes of the present invention generate intermediates with improved e.e. and chemical purity; thereby eliminating the need of additional chromatography steps. And, the processes of the present invention are scalable to generate commercial quantities of the final compound.