Kyorin Pharmaceutical Co., Ltd.

Keiji Hirai

Seigo Suzue

Takayoshi Ishizaki

Kuniyoshi Masuzawa

Tsutomu Irikura

Satoshi Murayama

Tatsuhiro Saito

Hideyuki Fukuda

Kikoh Obi

Novel cephem compounds represented by a formula [I] and pharmacologically admissible salts or capable of physiologically hydrolyzable nontoxic esters thereof are disclosed. ##STR1## [wherein R.sup.1 indicates a straight-chain or branched lower alkyl group, which may be substituted by carboxyl group which may be protected, trityl group, hydrogen atom or fluorine-substituted lower alkyl group, R.sup.2 indicates a hydrogen atom, metal atom, protective group for carboxyl group or ester residue producible hydrolyzable ester in vivo, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be identical or different, indicate hydrogen atoms, halogen atoms, straight-chain or branched lower alkyl groups, which may be substituted, mercapto groups, which may be substituted, lower alkylamino groups, hydroxyl groups, which may be protected, lower alkoxy groups, lower alkanoyl groups, lower alkoxycarbonyl groups, or lower alkylenedioxy groups, which may be substituted, being maybe formed with R.sup.3 and R.sup.4, R.sup.7 indicates a hydrogen atom, cyano group, halogen atom or COOR.sup.8 (R.sup.8 is hydrogen or lower alkyl group), R.sup.9 indicates an amino group, which may be protected, Z indicates N or CH, and n indicates 0 or 1]. Preparation processes for them and antibacterial agents containing them as effective ingredients are also claimed.

Cephem compounds, and antibacterial agents

Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R indicates a hydrogen atom or lower alkyl group, R.sup.1 indicates a lower alkyl group, R.sup.2 indicates a hydrogen atom, amino group or nitro group, X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, ##STR2## (here, n is 0 or 1, R.sup.3 indicates a hydrogen atom or lower alkyl group, R.sup.4 indicates a hydrogen atom, lower alkyl group or substituted lower alkyl group and R.sup.5 indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group), the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agents.

8-alkoxyquinolonecarboxylic acid and salts thereof

Quinolonecarboxylic acid derivatives of the following formula: ##STR1## wherein R indicates a hydrogen atom or lower alkyl group, R.sup.1 indicates a lower alkyl group, R.sup.2 indicates a hydrogen atom, amino group or nitro group, X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, ##STR2## (here, n is 0 or 1, R.sup.3 indicates a hydrogen atom or lower alkyl group, R.sup.4 indicates a hydrogen atom, lower alkyl group and R.sup.5 indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group), the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agents.

Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R indicates straight or branched lower alkyl, R.sup.1 indicates cycloalkyl having 3 to 6 carbon atoms, straight or branched lower alkyl, halogenoalkyl, alkenyl, hydroxyalkyl, lower alkylamino or substituted or non-substituted phenyl, R.sup.2 indicates hydrogen, halogen, nitro or amino, X indicates halogen, Z indicates halogen, azetidino, pyrrolidino, piperidino, morpholino, thiomorpholino, piperazino or homopiperazino of the following formula, ##STR2## (here, n is 1 or 2, R.sup.3 indicates hydrogen, lower alkyl, lower acyl, acyloxycarbonyl or benzyl, R.sup.4 and R.sup.5 indicate hydrogen, lower alkyl, aminoalkyl, hydroxyalkyl or phenyl each independently), or pyrrolidino or piperidino of the following formula, ##STR3## (here, k is 0, 1 or 2, l is 0, 1 or 2, m is 0 or 1, R.sup.6 indicates hydrogen, lower alkyl or hydroxy, R.sup.7 indicates hydrogen, lower alkyl, halogenoalkyl or hydroxyalkyl, R.sup.8 indicates hydrogen, lower alkyl, lower acyl, alkoxycarbonyl or benzyl), the hydrates and pharmaceutically acceptable acid addition or alkali salts thereof are useful as antibacterial agents.

Quinolonecarboxylic acid derivatives and their preparation

Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen atom or lower alkyl group; the hydrates or the pharmaceutically acceptable acid addition or alkali salts thereof are useful as an antibacterial agent.

Quinolonecarboxylic acid derivatives

The present invention is concerned with certain novel halogenobenzoic acid derivatives of the following formula, ##STR1## wherein R is a chlorine atom, amino group or hydroxy group, X is a chlorine atom or bromine atom, which are useful intermediates for the synthesis of antibacterial agent.

Halogenobenzoic acid derivatives and their preparation

Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R is hydrogen atom or lower alkyl group, Alk is lower alkylene group and X is hydrogen atom or halogen atom; the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agent.

The present invention is concerned with certain novel benzoylacetic acid ester derivatives (I) which are useful as a intermediates for synthesis of antibacterial agests. ##STR1## wherein R is a lower alkyl group, X is a halogen atom and Y is a chlorine or bromine atom.

Benzoylacetic acid ester derivatives and process for their preparations

Pyridonecarboxylic acid derivatives of the following formula, ##STR1## wherein R is hydrogen atom or lower alkyl group, R.sup.1 is lower alkyl group, cycloalkyl group or haloalkyl group, Y is hydrogen atom or halogen atom, or Y and R.sup.1 are ##STR2## which work together, R.sup.2 is hydrogen atom, lower alkyl group, alkoxycarbonyl group or acyl group and n is 0 or 1; the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agents.

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Kuki, Japan

Keiji Hirai