MannKind has been granted a patent for a method to synthesize N-protected 3,6-aminoalkyl-2,5-diketopiperazines. This process involves using a cyclic a-N protected active amino ester combined with an amine catalyst in an organic solvent. GlobalData’s report on MannKind gives a 360-degree view of the company including its patenting strategy. Buy the report here.
According to GlobalData’s company profile on MannKind, Smart inhalers was a key innovation area identified from patents. MannKind's grant share as of July 2024 was 54%. Grant share is based on the ratio of number of grants to total number of patents.
Synthesis method for n-protected diketopiperazines
The granted patent US12049453B2 outlines a method for synthesizing compounds, specifically focusing on a compound represented by Formula I and a diketopiperazine represented by Formula II. The synthesis involves heating a mixture to temperatures of up to 60° C, utilizing an organic solvent, preferably tetrahydrofuran (THF) or ethanol. The method employs an amine catalyst, with benzamindoxine being a specified example. Additionally, the process may include a co-catalyst, such as hydroxybenzotriazole or hydroxysuccinimide, present in a specific ratio to the catalyst. The claims detail the amounts of catalyst and co-catalyst used, emphasizing a range of 0.25 to 2.5 equivalents for the catalyst based on the cyclic amino compound.
Further claims specify the choice of protecting groups (PG) for the synthesis, including trifluoroacetyl, Cbz, and Boc. The patent also delineates the structural requirements for the compounds being synthesized, such as the presence of carbon (C) in specific positions. The method's versatility is highlighted by the various combinations of solvents, catalysts, and protecting groups, which can be tailored to achieve the desired chemical transformations. Overall, the patent provides a comprehensive framework for synthesizing these compounds, contributing to the field of organic chemistry and potentially facilitating advancements in pharmaceutical applications.
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