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The lactams 33 and 34 comprising 14-membered ring systems were most active in the series but nonetheless 100-fold less potent than the best disulfide and carba analogues ( Figure 7 The disulfide and carba analogues examined demonstrated a relative high stability against proteolysis by metallopeptidases, despite the similarities in the N-terminal to oxytocin 35 and vasopressin 36 that both serve as substrates to IRAP (Matsumoto et al., 2000