Kyorin Pharmaceutical Co., Ltd.

Kyorin Seiyaku Kabushiki Kaisha

Kyorin Seiyaki Kabushiki Kaisha

Seigo Suzue

Tsutomu Irikura

Keiji Hirai

Takayoshi Ishizaki

Kuniyoshi Masuzawa

Satoshi Murayama

Hiroaki Uchida

Susumu Kinoshita

Hirotaka Shinoda

Hiroshi Koga

Akira Ito

Keigo Nishino

Tatsuhiro Saito

Hideo Okubo

Hideyuki Fukuda

Toshiya Ikeda

Kodo Okada

Kikoh Obi

Katsuya Awano

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.

This invention relates to a novel imidazo[1,5-a]pyrimidine derivatives and process for their preparation. Moreover, it relates to novel imidazo[1,5-a]pyrimidine derivatives and salts thereof having antifungal activities, and process for their preparation.

Imidazo [1,5-a]pyrimidine derivatives and process for their preparation

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.

Pyridonecarboxylic acid derivatives and antibacterial pharmaceutical

Imidazo [1,5-a] pyrimidine derivatives of the formula (I) exhibit antifungal properties: ##STR1## wherein X.sub.1 and X.sub.2 are selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, an amino or substituted amino group, an alkoxy group, an alkylthio group, an alkylsulfinyl group and an alkylsulfonyl group; R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group and an aralkyl group. Compound (I) are prepared by reacting the corresponding .alpha.-acylamino-alkylpyrimidines with condensing agents to form chlorine-substituted imidazo [1,5-a] pyrimidines, then replacing one or both chlorine atoms in the pyrimidine ring with other substituents, if necessary.

Imidazo(1,5-a)pyrimidine derivatives and their use as antimycotic agents

The present invention is concerned with certain novel pyrozolo[1,5-a]pyridine derivatives, which are prepared by various means. The compounds of the present invention are antiallergic agents, referred to as SRS-A antagonists, and useful for treatment of allergic diseases.

Pyrazolo[1,5-a]pyridine derivatives and anti-allergic compositions

This invention relates to new and useful pyrazolopyridine and tetrahydro pyrazolopyridine derivatives which possess inhibitory activities on platelet aggregation. More particularly, it relates to method for their production as well as therapeutic compositions containing these compounds as used in cerebral and peripheral vascular insufficiency and its complications.

Pyrazolopyridines and tetrahydro pyrazolopyridines

This invention relates to compounds, 4-(4-substituted phenylalkyloxy) phenylalkyl nicotinates, represented by the following structural formula I and its salts, the methods for preparations thereof. ##STR1## wherein n.sub.1 is an integer from 2 to 6 inclusive, provided that n.sub.1 and n.sub.2 are not 1 at the same time, n.sub.1 is an integer from 1 to 6 inclusive, and X means chlorine or fluorine atom.

Nicotinic acid derivatives

This invention relates to new compounds of value as antibacterial agents. More particularly, it relates to quinoline carboxylic acid derivatives, the hydrates and the acid or alkali addition salts thereof.

Growing community of inventors

Kuki, Japan

Seigo Suzue