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Summary
Novelty: Substituted-azetidinones are disclosed, which are said to inhibit elastase and hence are potentially useful for treating rheumatoid arthritis and emphysema.
Biology: The activity of these compounds was determined spectrophotometrically, using human leukocyte elastase and a (synthetic) pentapeptide substrate (eg. Boc-AAPAN). Second order rate constants of 4×105 to 1.3 ×106 Ms–1 are reported for enzyme inactivation.
Chemistry: Nine synthetic examples are given. These methods involve converting known azetidones (EP-337549) into the compounds of the invention by reaction with the appropriate phosphonite. All of these compounds are explicitly claimed, including 4(S)-3,3-di-ethyl-1 [(R)-γ-n-propyl(4-methyl)benzylaminocarboxyl]-4-[4-(allyl(hydroxyphosphinyl)-methyl)phenoxy]azetidin-2-one.
Structure: