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Structural modification of the P2' position of 2,7-dialkyl-substituted 5(S)-amino-4(S)-hydroxy-8-phenyl-octanecarboxamides: the discovery of aliskiren, a potent nonpeptide human renin inhibitor active after once daily dosing in marmosets.

Abstract：

:Due to its function in the rate limiting initial step of the renin-angiotensin system, renin is a particularly promising target for drugs designed to control hypertension, a growing risk to health worldwide. Despite vast efforts over more than two decades, no orally efficacious renin inhibitor had reached the market. As a result of a structure-based topological design approach, we have identified a novel class of small-molecule inhibitors with good oral blood-pressure lowering effects in primates. Further lead optimization aimed for improvement of in vivo potency and duration of action, mainly by P2' modifications at the hydroxyethylene transition-state isostere. These efforts resulted in the discovery of aliskiren (46, CGP060536B, SPP100), a highly potent, selective inhibitor of renin, demonstrating excellent efficacy in sodium-depleted marmosets after oral administration, with sustained duration of action in reducing dose-dependently mean arterial blood pressure. Aliskiren has recently received regulatory approval by the U.S. Food and Drug Administration for the treatment of hypertension.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Maibaum J,Stutz S,Göschke R,Rigollier P,Yamaguchi Y,Cumin F,Rahuel J,Baum HP,Cohen NC,Schnell CR,Fuhrer W,Gruetter MG,Schilling W,Wood JM

doi

10.1021/jm070316i

subject

Has Abstract

pub_date

2007-10-04 00:00:00

pages

4832-44

issue

20

eissn

0022-2623

issn

1520-4804

journal_volume

50

pub_type

杂志文章

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