Synthesis and antibacterial activity of C-2 carboxyethenylthio-carbapenem derivatives.

Patents (and patent applications) on β-lactam antibacterials: January 1995 - December 1998

“…In parallel, Beecham scientists discovered a naturally-occurring carbapenem (e.g., olivanic acid) with (5R,6R,8S)-configuration with moderate bioactivity; however, no clinical agents resulted from this series [13]. During this review period, significant developments were reported by Suntory that showed (5R,6R,8S)-carbapenems (4) [101] and (5R,6R,8S)-penems (5) [102,103] with improved anti-MRSA activity versus carbapenems 1-3.…”

“…Takeda reported on a series of (thiacyclohexanoazole)carbapenems (11)(12)(13) [111]; notably, one of the diastereomers of carbapenem 13 (X and W = CH, T = N) is more potent then imipenem against Escherichia coli and Haemophilus influenzae. Subtle structural changes on the C(2)-moiety were observed to afford anti-Helicobacter activity; notable, from Sankyo, are the [N-(thiazolidinyl)azetindinylthio]carbapenem (14) and ( [112].…”