To obtain the subject new derivative strong in antimicrobial activities, stable to dehydropeptidase I, high in proportion in urine and useful as an antimicrobial agent.
The subject derivative is a tricyclic heterocyclic derivative of formulas I or II [R1 is H or the like; (m), (k), (n) and (s) are each 0 or 1; (p) and (t) are each 0-2; R2 is H or the like; R3 is H or the like], e.g. (5S,6R,7R, or 11S)-11-(azetidin-3-ylthio)-5-[(R)-1-hydroxyethyl]-4-oxo-3-azatricyclo[5.4.0.03,6] undeca-1-ene-2-carboxylic acid. The compound of formula I is obtained, for example, by subjecting a compound of formula III (R7 is a protective group of OH) to an epoxy ring-opening reaction with a mercaptan compound of formula IV [R2pr and R3pr are (protected) R2 and R3 respectively] in the presence of a base, oxidizing the product of the epoxy ring-opening reaction, further reacting the oxidized product with an oxalyl chloride derivative to provide a compound of formula V (R8 is a protective group of carboxy group) and cyclizing and deprotecting the compound of formula V.
SHIMOJI YASUO
MICHAEL TRACEY
ANDREW B KELSON
KENNETH J RYAN
BERAPARSHI APENDER
ROBERT R WEBB
| JPS4937A | 1974-01-05 | |||
| JPS6264379A | 1987-03-23 |
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