American Cyanamid Company

Other

Carl B Ziegler

Gregg Brian Feigelson

William V Curran

Yang-I Lin

Karen Bush

Panayota Bitha

Timothy W Strohmeyer

Subas Sakya

Daniel B Moran

Paul Frank Fabio

Deborah Steinberg

Carbapenem antibiotic compounds of the general formula: ##STR1## wherein the moiety ##STR2## is a 4, 5 or 6 membered mono, di- or tri-substituted oxygen or sulfur containing ring; wherein Z is oxygen, sulfur, sulfoxide and sulfone, pharmaceutical compositions thereof useful for the treatment of bacterial infections, processes for preparing the compounds and new intermediates useful in the process.

2-thiosubstituted carbapenems

Carbapenem antibiotic compounds of the general formula: ##STR1## wherein the moiety ##STR2## is a 4, 5 or 6 membered mono, di- or tri- substituted oxygen or sulfur containing ring; wherein Z is oxygen, sulfur, sulfoxide and sulfone, pharmaceutical compositions thereof useful for the treatment of bacterial infections, method of inhibiting a Beta-lactamase enzyme by administering said compounds, processes for preparing the compounds and new intermediates useful in the process are disclosed.

Method of inhibiting a .beta.-lactamase enzyme by administering novel

New 4-substituted azetidinones having the formulae I and II: ##STR1## wherein X is oxygen, sulfur or a moiety of the formula NR.sup.6 where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined hereafter, which are intermediates for the preparation of carbapenem and carbacephem antibacterials and processes for producing such antibacterials through the utilization of an acid mediated ring closure reaction.

4-substituted azetidinones as precursors to 2-substituted-3-carboxy

Compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.12, R.sup.16 and R.sup.17 are defined in the specification are provided. These compounds are useful as intermediates for the preparation of carbapenem antibacterials.

Tetrahydrofuanyl compounds of the following formulae: ##STR1## are disclosed.

Method for producing tetrahydrofuranyl compounds

Carbapenem antibiotic compounds of the general formula: ##STR1## wherein the moiety ##STR2## is a 4, 5 or 6 membered mono, di- or tri- substituted oxygen or sulfur containing ring; wherein Z is oxygen, sulfur, sulfoxide and sulfone, pharmaceutical compositions thereof useful for the treatment of bacterial infections, processes for preparing the compounds and new intermediates useful in the process.

The invention provides a novel class of 6-(isoxazolinyl)methyl penicillanic acid 1,1-dioxide compounds having the formula: ##STR1## wherein M, X, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are described in the specification;

Process for preparing 6-[(isoxazolinyl)methyl]penicillanic acid

The invention provides substituted allylazetidinone compounds having the formula: ##STR1## and propargyl azetidinone compounds having the formula: ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.30, X, Y and Q are defined in the specification.

2-substituted alkyl-3-carboxy carbapenems as antibiotics and a method of

The invention relates to new 2-substituted alkyl-3-carboxy carbapenems having the formula: ##STR1## with R.sup.1, R.sup.2, R.sup.3, X and Y defined hereafter as antibiotics and beta lactamase inhibitors produced by a novel Michael addition-elimination reaction of a substituted allyl azetidinone in the reaction shown: ##STR2## with R.sup.1, R.sup.2, Q, X and Y defined hereafter.

2-substituted alkyl-3-carboxy carbopenems as antibiotics and a method of

New 4-substituted azetidinones having the formulea I and II: ##STR1## with R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and X defined hereafter, which are intermediates for the preparation of carbapenem and carbacephem antibacterials and processes for producing such antibacterials through the utilization of an acid mediated ring closure reaction.

Novel 2-substituted alkyl-3-carboxy carbapenems as antibiotics and a

Novel substituted quinolinecarboxylic acid derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkali metal, alkaline earth metal or lower alkyl; R.sub.2 is hydrogen, benzyl or alkyl (C.sub.1 -C.sub.3); X is hydrogen or fluoro; which have antibacterial activity, intermediates useful in the preparation of the compounds, methods of producing and using the compounds to treat bacterial infections in animals.

8-fluoro and 7, 8,

Novel substituted quinolinecarboxylic acid derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkali metal, alkaline earth metal or lower alkyl; R.sub.2 is hydrogen, benzyl or alkyl(C.sub.1 -C.sub.3); X is hydrogen or fluoro; which have antibacterial activity, intermediates useful in the preparation of the compounds, methods of producing and using the compounds to treat bacterial infections in animals.

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Pearl River, NY, United States of America

Carl B Ziegler