Riker Laboratories Inc.

Richard M Stern

Robert A Scherrer

Walton J Hammar

John F Gerster

Vernon R Fletcher

The compounds 8-bromo-6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-c arboxylic acid and 8-chloro-6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2- carboxylic acid are disclosed as potent antimicrobials. Pharmaceutically-acceptable carboxylate salts, acyl chlorides, esters and alkylaminoalkyl ester salts of the acids are also disclosed.

Intermediates for the preparation of 8,9-dihalobenzo[ij]quinolizine

Antimicrobial 2-nitro-3-phenylbenzofurans wherein the benzo or the 3-phenyl portion of the molecule is bonded to an alkylene or an oxyalkylene group which is in turn bonded to a basic nitrogen atom or to the nitrogen atom of an (N-lower alkanoyl)amino group.

Aminoalkyl and aminoalkoxy derivatives of 2-nitro-3-phenylbenzofuran

Antimicrobial compounds of the following formula are disclosed: ##STR1## wherein X is selected from the group consisting of --O--, --CH.sub.2 and ##STR2## m is 0 or 1; R.sub.1 is selected from the group consisting of hydrogen, nitro, amino, lower alkyl, lower alkanamido, lower N,N-dialkylamino, formamido, hydroxy, lower alkoxy, halogen, lower haloalkanamido and pyrryl; n is 1 or 2; and R.sub.2 is selected from the group consisting of hydrogen, methyl, fluoro, chloro and nitro. Acyl chlorides, esters, alkylaminoalkyl ester salts, amides and pharmaceutically acceptable carboxylate salts are also disclosed. Pharmaceutical compositions containing these compounds, methods of using these compound and synthetic intermediates are also disclosed.

Phenyl-substituted tricyclic antibacterial agent intermediates

The compounds 5-carboxyl-6-fluoroquinaldine, 6-fluoro-5-methylquinaldine, 6-fluoro-5-methyl-1,2,3,4-tetrahydroquinaldine, 1,2-dihydro-6-fluoro-5-hydroxymethylquinaldine and diethyl 2-[N-(6-fluoro-5-methyl-1,2,3,4-tetrahydroquinaldinyl)]methylenemalonate are disclosed as useful intermediates for preparing the antimicrobial agent 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzol[ij]quinolizine- 2-carboxylic acid.

Precursors of

The compounds 5-bromo-6-fluoroquinaldine, 5-bromo-6-fluoro-1,2,3,4-tetrahydroquinaldine, 1-acetyl-5-bromo-6-fluoro-1,2,3,4-tetrahydroquinaldine and diethyl 2-[N-(6-fluoro-5-methoxy-1,2,3,4-tetrahydroquinaldinyl)]-methylenemalonate are intermediates for preparing antimicrobial 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo[ij]-quinolizine-2 -carboxylic acids.

Precursors of 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo[ij]q

The compounds 8-bromo-6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quiniolizine-2- carboxylic acid and 8-chloro-6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H,-benzo[ij]quinolizine-2 -carboxylic acid are disclosed as potent antimicrobials. Pharmaceutically-acceptable carboxylate salts, acyl chlorides, esters and alkylaminoalkyl ester salts of the acids are also disclosed.

6-Fluoro-5-nitroquinaldine

Tetrazol-5-yl 2-nitro-3-phenylbenzofurans and antimicrobial use thereof

Antimicrobial 8,9-dihalobenzo[ij]quinolizine carboxylic acids

The compound 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carbo xylic acid is disclosed as a potent antimicrobial agent with a broad spectrum of activity. Esters, acyl chlorides, alkylaminoalkyl ester salts and pharmaceutically acceptable carboxylate salts of the acid are also disclosed. Methods of using these compounds, pharmaceutical compositions comprising these compounds and synthetic intermediates for preparing these compounds are described.

Antimicrobial 6,7-dihydro-5,8-dimethyl-9 fluoro-1-oxo-1H, 5H-benzo (ij)

The 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo- 1H,5H-benzo[ij]quinolizine-2-carboxylic acids are disclosed as potent antimicrobial agents with a broad spectrum of activity. Esters, acyl chlorides, amides, alkylaminoalkyl ester salts and pharmaceutically acceptable carboxylate salts are also disclosed. Methods of using these compounds, pharmaceutical compositions comprising these compounds and synthetic intermediates for preparing these compounds are also described.

Antimicrobial 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo[ij]q

Phenyl-substituted tricyclic antibacterial agents

Antimicrobial compounds of the following formula are disclosed: ##STR1## wherein Het is selected from the goup consisting of pyrryl, pyrrolidyl, tetrazolyl of the formula ##STR2## wherein R.sup.1 is lower alkyl or benzyl and oxadiazolyl of the formula ##STR3## wherein R.sup.2 is lower alkyl, trifluoromethyl or --NH.phi.--; X is hydrogen and when Het is pyrryl or pyrrolidyl, X may be fluorine. Pharmaceutically acceptable carboxylate salts and esters of the acids are also disclosed.

Antimicrobial 8-substituted benzo [IJ]quinolizines

This invention relates to antimicrobial compounds of the formula ##STR1## wherein X is hydrogen or fluorine; Y is selected from the group consisting of ##STR2## and ester, carboxylate salts, and alkylaminoalkyl ester salts thereof.

Antimicrobial derivatives of 8-amino and 8-aminomethyl

The compounds 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid and 8-cyano-6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-c arboxylic acid are disclosed as potent antimicrobial agents. Pharmaceutically-acceptable carboxylate salts, esters, acyl chlorides, amides and alkylaminoalkyl ester salts of the acids are also disclosed.

Antimicrobial

2-Nitrobenzofurans in which the furan ring is either fused to or substituted by a fused bicyclic system, which are active as antimicrobial agents, processes for their use and intermediates therefor are described.

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Cottage Grove, MN, United States of America

Richard M Stern