Carbapenams and carbapen-2-ems and process therefor

Details Carbapenams and carbapen-2-ems and process therefor Carbapenams and carbapen-2-ems and process therefor

1982-02-11

1984-01-31

Lee, Mary C.

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

204158R, 2602452T, 424250, 424272, 424274, C07D48704

Patent

active

044291280

ABSTRACT:
Carbapenam-3-carboxylic acids and carbapen-2-em-3-carboxylic acids substituted at the 1-position with an oxo, a hydroxy or an acetoxy group, variously substituted at the 2-position with such groups as methyl, acetoxymethyl, methanesulfonyloxy, alkoxy, alkylthio, aminoalkylthio or amidinoalkylthio and optionally substituted at the 6-position with a hydroxyalkyl group, an acetoxyalkyl group or a conventional penicillin side-chain, pharmaceutically-acceptable salts thereof and various esters thereof wherein the esterifying group is selectively removed in the laboratory, or hydrolyzed under physiological conditions.
These compounds are useful either systemically or topically in the treatment of diseases caused by susceptible microorganisms, as animal feed additives for promotion of growth, or in the preservation of biodegradable materials, or as intermediates to compounds having such antibacterial activity.
Key to the synthesis of these compounds is the light catalyzed rearrangement of 2-diazo-1-oxoceph-3-em-4-carboxylates to 1-oxocarbapen-2-em-3-carboxylates, a newly discovered reaction determined to be of general applicability.

REFERENCES:
patent: 3592751 (1971-07-01), Archer et al.
patent: 4208422 (1980-06-01), Christensen et al.
patent: 4234596 (1980-11-01), Christensen et al.
patent: 4348264 (1982-09-01), Rosati
Kemetani et al., Heterocycles, 12, pp. 1189-1190, (1979).
Onoue et al., Tetrahedron Letters No. 40, pp. 3867-3870, (1979).
Baxter et al., J. Chem. Soc. Chem. Commun. 1979, pp. 236-237, (1979).
Cama and Christensen, J. Am. Chem. Soc., 100, pp. 8006-8007, (1979).
Ratcliffe et al., Tetrahedron Letters 21, pp. 31-34, (1980).

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