- Quaternary Heterocyclylamino β-Lactams: A Generic Alternative to the Classical Acylamino Side Chain
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6β-penam-3-carboxylates and 7β-ceph-3-em-4-carboxylates have been found to be interesting new classes of antibacterial β-lactams, readily available by SN2 Ar coupling of fluoro-substituted quaternized pyridines and appropriate amino lactam carboxylic acids.Compared to penicillin G, the penam 12c exhibited a spectrum extended to Gram-negative species, such as Escherichia, Shigella, Klebsiella and Enterobacter, offset by a loss of potency against Gram-positive spacies.Excluding Pseudomonas, many examples of the cephems showed excellent activity against the above Gram-negative organisms, and in some cases, such as 15i, the spectrum included good performance against the staphylococci and streptococci.With Serratia and many Proteus species, there was an adverse inoculum and medium effect which was not observed in the good Gram-positive reach of the cephem series.
- Hannah, John,Johnson, Charles R.,Wagner, Arthur F.,Walton, Edward
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p. 457 - 469
(2007/10/02)
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- 3-Heterothio-7-ureido cephalosporins
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Compounds of the formula STR1 wherein R1 is hydrogen, lower alkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, phenyl, phenyl-lower alkyl and substituted phenyl and phenyl-lower alkyl; R2 is hydrogen or lower alkyl; R3 is h
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- 3-Heterothio[(thioalkyl)thioacetyl]cephalosporanic derivatives
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3-Heterothio[(thioalkyl)thioacetyl]cephalosporin derivatives which have the formula STR1 wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, tri(lower alkyl)silyl, a salt forming ion, or the group STR2 R 1 is hydrogen, lower alkyl, phenyl, thienyl of furyl; R2 and R6 each is hydrogen or lower alkyl; R3 and R5 each is lower alkyl, phenyl or phenyl-lower alkyl; and R4 is a five- or six-membered nitrogen and/or sulfur or oxygen-containing ring system; are useful as antibacterial agents.
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- 3-Heterothiomethyl-7α-methoxy-7β-tetrazolylmethylthioacetamido-3-cephem derivatives
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7α-Methoxy-7β-tetrazolylmethylthioacetamido-3-cephem derivatives which have a heterothiomethyl substituent in the 3-position are novel compounds which are useful as antimicrobial agents.
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- 3-Heterothio derivatives of (carbamoylthioacetyl)cephalosporins
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3-Heterothio(carbamoylthioacetyl)cephalosporin derivatives of the general formula EQU1 wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, tri(lower alkyl)silyl, a salt forming ion or the group EQU2 R1 is hydrogen, lower alkyl, phenyl, thienyl, or pyridyl; R2 is lower alkyl or phenyl-lower alkyl; R3 is a five or six membered nitrogen, sulfur and/or oxygen containing ring system; and R4 is lower alkyl, phenyl or phenyl-lower alkyl; are useful as antibacterial agents.
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- 3-Heterothio[(oxyalkyl)thioacetyl]cephalosporin derivatives
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3-Heterothio[(oxyalkyl)thioacetyl] cephalosporin derivatives which have the formula EQU1 wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, tri (lower alkyl) silyl, a salt forming ion, or the group EQU2 R1 is hydrogen, lower alkyl, phenyl, thienyl or furyl; R2 and R6 each is hydrogen or lower alkyl; R3 and R5 is lower alkyl, phenyl or phenyl-lower alkyl; and R4 is a five- or six-member nitrogen and/or sulfur or oxygen-containing ring system; are useful as antibacterial agents.
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- 3-Heterothio derivatives of (α-thiocarbonylamino) cephalosporins
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3-Heterothio(α-thiocarbonylamino)cephalosporin derivatives of the general formula STR1 wherein R is hydrogen, lower alkyl, phenyl-lower alkyl, tri(lower alkyl)silyl, trihaloethyl, a salt forming ion or the group STR2 R1 is hydrogen, lower alkyl, cyclo-lower alkyl, unsaturated cyclo-lower alkyl, phenyl, substituted phenyl or thienyl; R2 and R5 each is hydrogen or lower alkyl; R3 is a five or six membered nitrogen, sulfur and/or oxygen containing ring system; and R4 is lower alkyl, phenyl or phenyl-lower alkyl; are useful as antibacterial agents.
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