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A novel series of potent and selective PDE5 inhibitors with potential for high and dose-independent oral bioavailability.

Abstract：

:Sildenafil (5-[2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one), a potent and selective phosphodiesterase type 5 (PDE5) inhibitor, provided the first oral treatment for male erectile dysfunction. The objective of the work reported in this paper was to combine high levels of PDE5 potency and selectivity with high and dose-independent oral bioavailability, to minimize the impact on the C(max) of any interactions with coadministered drugs in the clinic. This goal was achieved through identification of a lower clearance series with a high absorption profile, by replacing the 5'-piperazine sulfonamide in the sildenafil template with a 5'-methyl ketone. This novel series provided compounds with low metabolism in human hepatocytes, excellent caco-2 flux, and the potential for good aqueous solubility. The in vivo oral and iv pharmacokinetic profiles of example compounds confirmed the high oral bioavailability predicted from these in vitro screens. 5-(5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-(1-ethyl-3-azetidinyl)-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (2) was selected for progression into the clinic.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Allerton CM,Barber CG,Beaumont KC,Brown DG,Cole SM,Ellis D,Lane CA,Maw GN,Mount NM,Rawson DJ,Robinson CM,Street SD,Summerhill NW

doi

10.1021/jm060113e

subject

Has Abstract

pub_date

2006-06-15 00:00:00

pages

3581-94

issue

12

eissn

0022-2623

issn

1520-4804

journal_volume

49

pub_type

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