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Curr Radiopharm. 2012 Oct;5(4):314-7.

Synthesis of a potent cathepsin s inhibitor labeled with deuterium and carbon-14.

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Boehringer Ingelheim Pharmaceuticals, Research and Development Center, Ridgefield, CT 06877-0368, USA.


Morpholine-4-carboxylic acid {(S)-1-[4-cyano-1-(3-morpholin-4-yl-propyl)-piperidin-4-ylcarbamoyl]-4,4- dimethyl-hexyl}-amide, (1) is a potent reversible and selective cathepsin S inhibitor. Deuterium labeled (1) was prepared in four steps in 62% overall yield from [2H8]- morpholine and chiral acid (6). Carbon-14 labeled (1) was obtained in two steps using sodium [14C]-cyanide in a modified Strecker reaction followed by amide bond formation with acid (6) in 74% overall radiochemical yield. The phosphate salt of this compound was produced by treatment with phosphoric acid in methanol in 97% yield.

[Indexed for MEDLINE]

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