676489-50-2Relevant academic research and scientific papers
Synthetic process development of BMS-599793 including azaindole Negishi coupling on kilogram scale
Pikul, Stanislaw,Cheng, Hua,Cheng, Allen,Huang,Ke, Alex,Kuo, Lunghuang,Thompson, Andrew,Wilder, Susan
, p. 907 - 914 (2013)
A new approach to the synthesis of 1 (DS003, BMS-599793), a small-molecule HIV entry inhibitor, is described. The initial medical chemistry route has been modified by rearranging the sequence of synthetic steps followed by replacement of the Suzuki coupling step by the Negishi conditions. Acylation of the resulting azaindole 7 under the Friedel-Crafts conditions is studied using monoesters of chlorooxalic acid in the presence of aluminum chloride. Polymorphism of 1 is also investigated to develop conditions suitable for preparation of the desired Form 1 of the target compound. The new route is further optimized and scaled up to establish a new process that is applied to the synthesis of kilogram quantites of the target active pharmaceutical ingredient.
METHODS FOR SYNTHESIZING ANTIVIRAL COMPOUNDS
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Page/Page column 19, (2009/10/22)
New synthetic methods and intermediates are provided for the synthesis of antiviral compounds.
Indole, azaindole and related heterocyclic 4-alkenyl piperidine amides
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Page/Page column 93, (2010/02/06)
This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with new piperidine 4-alkenyl derivatives that possess unique antiviral activity. More particularly, the present invention relates to compounds useful for the treatment of HIV and AIDS. The compounds of the invention for the general Formula I: wherein: Z is Q is selected from the group consisting of: —W— is
