Synthesis of non-peptide bradykinin B2 receptor antagonists

The syntheses of the potent, competitive bradykinin B2 receptor antagonists, 1–3, are described. These compounds represent the three structural classes of B2 receptor antagonists discovered in our program. Compounds 1–3 bind to the human IMR 90 fetal lung fibroblast bradykinin B2 receptor with affinity constants Ki = 3.4 μM, 0.77 μM, and 0.060 μM, respectively.