Bristol-myers Company

Bristol-myers Squibb Compnay

Bristol-myers

Marcel Menard

Gary M Lim

Terry T Conway

Alain Martel

Gilles Caron

Carol Bachand

James L Douglas

Jacques Meunier

Compounds of the formula ##STR1## wherein A is an unsubstituted or hydroxy-substituted straight or branched C.sub.1-10 alkylene group or a straight or branched C.sub.1-10 alkylene group having an intervening heteroatom selected from oxygen, sulfur and nitrogen;

4-substituted alkyl carbapenem antibiotics

This invention relates to 2-substituted and 2,6-disubstituted penem compounds of the formula ##STR1## wherein Y is hydrogen, halo or certain organic radicals and X represents certain hetero-interrupted substituted alkyl radicals. Also included in the invention are pharmaceutically acceptable salts of the above compounds and derivatives of the above compounds in which the carboxyl group at the 3-position is protected as by an easily removable ester protecting group. The compounds of the present invention are potent antibacterial agents or are of use as intermediates in the preparation of such agents.

4-Acylthioazetidinone intermediates for antibacterial agents

2,6 Disubstituted penems and intermediates therefor

This invention relates to 2-substituted and 2,6-disubstituted penem compounds of the formula ##STR1## wherein Y is hydrogen, halo or certain organic substituents and X represents certain organic substituents. Also included in the invention are pharmaceutically acceptable salts of the above compounds and derivatives of the above compounds in which the carboxyl group at the 3-position is protected as by an easily removable ester protecting group. The compounds of the present invention are potent antibacterial agents or are of use as intermediates in the preparation of such agents.

Antibacterial agents and metal containing azetidinone intermediates

This invention relates to 2-substituted and 2,6-disubstituted penem compounds of the formula ##STR1## wherein Y is hydrogen, halo or certain organic radicals and X represents certain hereto-interrupted substituted alkyl radicals. Also included in the invention are pharmaceutically acceptable salts of the above compounds and derivatives of the above compounds in which the carboxyl group at the 3-position is protected as by an easily removable ester protecting group. The compounds of the present invention are potent antibacterial agents or are of use as intermediates in the preparation of such agents.

Antibacterial agents of the .beta.-lactam type

2,6-Disubstituted penem compounds

Antibacterial agents, and 4-thio azetidinone intermediates

There is described the stereoselective total synthesis of novel .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 halo or hydroxyl 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.

Antibacterial analogs of isocephalosporins

Disclosed are novel phosphorane intermediates of the formula ##STR1## wherein Z is phenyl or C.sub.1 -C.sub.6 alkyl. The intermediates are of use in preparing 2-penem-3-carboxylic acid compounds having potent antibacterial activity.

Novel phosphorane intermediates for use in preparing penem antibiotics

There is described the stereoselective total synthesis of novel .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 hydroxyl esterified with a sulfonic acid residue and X is acylamino. Also included in the invention are compounds of the above formula in which the carboxyl group of 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.

0-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents

There is described the stereoselective total synthesis of novel .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 etherified hydroxyl 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.

O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents

There is described the preparation of novel 2-penem-3-carboxylic acid compounds having the formula ##STR1## and easily cleavable esters and carboxylic acid salts thereof. The compounds of formula I, particularly the dextrorotatory isomers thereof, are potent antibacterial agents or are of use as intermediates in the preparation of such agents.

2-Methylpenem-3-carboxylic acid antibiotics

There is described the stereoselective total synthesis of novel .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 halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I 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 of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.

.DELTA..sup.2,3 -1,4 Morpholine-2-carboxylic acid derivatives as

There is described the stereoselective total synthesis of novel .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 halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carbonyl 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 of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.

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Candiac, Canada

Marcel Menard