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Synthesis of the Nonpeptide Renin Inhibitor A-68064 and the ACE Inhibitor Methyl Enalaprilat from (5S)-2,3,5,6-Tetrahydro-5-alkyl-N-(tert-butyloxycarbonyl-4H-1,4-oxazine-2-ones

✍ Scribed by William R. Baker; Stephen L. Condon

Publisher: Elsevier Science
Year: 1992
Tongue: French
Weight: 218 KB
Volume: 33
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)91678-2

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✦ Synopsis

The nonpeptide renin inhibitor, A-68064, and the ACE inhibitor methyl enalaprilat were synthesizedfrom (5S) 235,6-tetrahydro-S-benryI(bury2)-N-(tert-buto~car~nyl)~H~l fl-oxazine-2-ones la and 76, and (5s) 2.3,S,6-tetrahydro-5methyl-N-(fert-butoxycarbonyl)-4H-l.4-oxazine-2-one 12, respectively.

We have recently identified a novel series of renin inhibitory compounds whose structure is typified by A-68064 (11.1 These nonpeptide inhibitors possessed a novel (2S,4S)-3-aza-2,4-disubstituted glutaric acid moiety 2 at the Pfl3 position of the molecule, a moiety also found in the ACE inhibitor, enalaprilat (16). We have developed 1 nonpeptide renin inhibitor

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