Gilead Sciences has been granted a patent for methods of preparing 1′-cyano nucleosides, specifically a compound of Formula (I), from a compound of Formula (II-a) in a flow reactor. GlobalData’s report on Gilead Sciences gives a 360-degree view of the company including its patenting strategy. Buy the report here.
According to GlobalData’s company profile on Gilead Sciences, Peptide pharmacophores was a key innovation area identified from patents. Gilead Sciences's grant share as of May 2024 was 42%. Grant share is based on the ratio of number of grants to total number of patents.
Method of preparing 1'-cyano nucleosides from compound of formula (ii-a)
A recently granted patent (Publication Number: US12012431B2) discloses a method for preparing a compound of Formula (II-a) involving the use of specific oxidants, bases, and solvents. The method includes the addition of a fifth input mixture to a fifth reactor, with the oxidant options ranging from (2,2,6,6-tetramethylpiperidin-1-yl)oxyl to N-methylmorpholine-N-oxide/tetrapropylammonium perruthenate, among others. The fifth base can be selected from various options like sodium bicarbonate or potassium hydrogen phosphate, while the fifth solvent may include dichloromethane, chloroform, or acetonitrile, among others.
Furthermore, the patent details the preparation of a compound of Formula (V) through the addition of a sixth input mixture to a sixth reactor, involving specific amine-protecting agents, bases, and solvents. The amine-protecting agent options include chlorotrimethylsilane, while the sixth base can be phenylmagnesium chloride or sodium hydride, among others. The sixth solvent options range from tetrahydrofuran (THF) to toluene. The method also specifies temperature ranges for the reactors, with the fifth reactor maintained between -10°C to 60°C and the sixth reactor between -70°C to 40°C, among other conditions outlined in the patent.
In summary, the patent provides a detailed method for the preparation of compounds of Formula (II-a) and (V) through specific combinations of reactants, bases, and solvents in designated reactors under controlled temperature conditions. The disclosed method offers a systematic approach to synthesizing these compounds, providing valuable insights for researchers and practitioners in the field of chemical synthesis.
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