O-2-isocephem-4-carboxylic acid derivatives as antibacterial age

Details O-2-isocephem-4-carboxylic acid derivatives as antibacterial age O-2-isocephem-4-carboxylic acid derivatives as antibacterial age

1978-06-02

1979-10-23

Randolph, John D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

C07D26534

Patent

active

041721993

ABSTRACT:
There is described the stereoselective total synthesis by a variety of routes of novel suitably substituted .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is hydrogen or the residue of an ester group and X is acylamino. Also included in the invention are compounds of the above formula in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds. The compounds are potent antibacterial agents.

REFERENCES:
patent: 4012383 (1977-03-01), Belleau et al.
patent: 4065623 (1977-12-01), Belleau et al.
patent: 4066831 (1978-01-01), Belleau et al.
patent: 4113946 (1978-09-01), Belleau et al.
patent: 4123528 (1978-10-01), Cama et al.
Brunwin et al., J. Chem. Soc. Chem. Comm., 1972, pp. 589-590.
Lowe et al., J. Chem. Soc. Perkins I, pp. 1321-1328 (1973).
Sheehan et al., J. Heterocyclic Chemistry, vol. 5, pp. 779-783 (1968).

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