Process for the production of artemisinin intermediates

Abstract

This application relates to a process for the production of (2R)-dihydroartemisinic acid or (2R)-dihydroartemisinic acid esters from artemisinic acid or artemisinic acid esters, respectively, by diimine hydrogenation of the exocyclic CC-double bond, and use of said process in the production of the antimalarial drug artemisinin.

Description

[0001] Cross References to Related Applications [0002] This application claims priority under 35 U.S.C. §119 to U.S. Provisional Patent Application 61 / 241,744, filed September 11, 2009, which is hereby incorporated by reference in its entirety. Background technique [0003] Malaria is a tropical disease common in Africa, Southeast Asia and South America. An estimated 300-500 million people are infected with malaria, making it one of the world's leading infectious diseases. In 2006, an estimated 1.5 to 2.7 million deaths were caused by malaria and most of the deaths occurred in children under 5 years of age. Disease control is hampered by the emergence of multidrug-resistant strains of the parasite Plasmodium falciparum. Therefore, the development of new antimalarial drugs and alternative methods of preparing antimalarial drugs are important world health goals. One of these antimalarial drugs is artemisinin of formula II, [0004] [0005] That is, sesquiterpene lacton...

AI Technical Summary

Problems solved by technology

However, homogeneous catalytic hydrogenation using transition metal complexes is very expensive due to noble metals (e.g. rhodium or ruthenium) and complexed organic ligands, complex metal and ligand recovery, often low substrate-to-catalyst Substrate to catalyst loadings and conversions, reactions sensitive to trace catalyst poisons and require expensive high pressure reactor equipment e.g. operating at hydrogen pressures up to 60 bar on a large scale

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