Azetidinone N-phosphonomethyl esters

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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540363, 540364, 540205, 548112, 548406, 548413, 560170, 560169, 562564, 562567, C07F 965

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active

048208159

ABSTRACT:
The invention provides azetidinones of the formula ##STR1## where R.sub.4 is hydrogen, amino or protected amino; R.sup.0 is H when R.sub.4 is amino or protected amino, or C.sub.1 -C.sub.4 alkyl when R.sub.4 is H; R.sub.1 is H, CH.sub.3, --CH.sub.2 --.sub.n Y where Y is OH, protected OH, --CH.sub.2 OH, protected --CH.sub.2 OH, halogen, COOH or protected COOH; n is 1 or 2; --CH.sub.2 --C(O)SR.sub.1 ' where R.sub.1 ' is e.g., C.sub.1 -C.sub.4 alkyl; R.sub.2 is H or protecting group and R.sub.3 is e.g., alkyl or phenyl. The azetidinones obtained are useful intermediates to carbapenems and carbacephems and monocyclic antibacterials, e.g., .alpha.-(dialkylphosphono)-[[3.beta.-[2-(2-aminothiazol-4-yl)-2-(syn)metho xyiminoacetylamino]azetidin-2-one-1-yl]]acetic acid and pharmaceutically acceptable salts thereof.

REFERENCES:
Derwent Abstract of Kyowa Hakko Kogyo, Japan Application No. J5 7091-991.
Herdewijn, Chem. Abs. 101, 38237z (1983).
Hirata, Chem. Abs. 93, 150115a (1978).

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