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• W2099974733 abstract "Dasatinib (SPRYCEL®) is a multiple kinase inhibitor approved for the treatment of chronic myelogenous leukemia and Philadelphia chromosome-positive acute lymphoblastic leukemia in patients with resistance to prior therapy, including imatinib mesylate (Gleevec®). Radiolabeled dasatinib and its piperazine N-dealkyl metabolite were synthesized to investigate absorption, distribution, metabolism, and elimination of the compounds in humans and animals. These compounds were prepared following a three-step sequence, which included thiazole carboxamide formation via cyclization of labeled thiourea with a brominated oxyacrylamide precursor. In the final step a common intermediate was converted to either [14C]dasatinib or the radiolabeled piperazine N-dealkyl metabolite with labeling in the aminothiazole ring. Syntheses of both compounds were achieved with radiochemical purities in excess of 98%. Stable-labeled dasatinib and the piperazine N-dealkyl metabolite were also needed for use as mass spectral internal standards in support of bioanalytical assays. By following the same route used for the carbon-14 synthesis, [13C4, 15N2]dasatinib and the [13C4, 15N2]metabolite were prepared with labeling in both the dichloropyrimidine and thiazole ring systems. This convergent process introduced stable isotope labeling through (1, 2, 3-13C3) diethyl malonate and [13C,15N2]thiourea. Copyright © 2008 John Wiley & Sons, Ltd." @default.
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• W2099974733 date "2008-01-01" @default.
• W2099974733 modified "2023-10-14" @default.
• W2099974733 title "Synthesis of14C-labeled and13C-,15N-labeled dasatinib and its piperazineN-dealkyl metabolite" @default.
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• W2099974733 doi "https://doi.org/10.1002/jlcr.1469" @default.
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