Meiji Seika Kaisha, Ltd.

Other

Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

Meiji Seika Kabushiki Kaisha

Susumu Mitsuhashi

Ken Nishihata

Kunio Atsumi

Shinichi Kondo

Takashi Yoshida

Shunzo Fukatsu

Kenji Sakagami

Katsuharu Iinuma

Yuichi Yamamoto

Seiji Shibahara

Kiyoaki Katano

Yasushi Murai

Shigeo Seki

Tsuneo Okonogi

Eiichi Akita

Satoru Nakabayashi

Fumio Kai

Osamu Sakanaka

Toshiaki Kudo

Shinjiro Sumi

Toshinori Saito

Shouhei Yasuda

Katsufumi Sebata

Nobuo Itoh

Tomio Takeuchi

Hitoshi Ikeda

Takashi Tsuruoka

Hideaki Takahashi

Fumiya Hirano

Masahiro Onodera

Shokichi Nakajima

Sinichi Kondo

Hitoshi Yamada

Tomoya Machinami

New compounds are disclosed having the general formulas (1) and (2): ##STR1## Also described is a process for preparing the compounds of formulas (1) and (2). Further described is a process for preparing a cephalosporin derivative having formula (5): ##STR2## by converting the compound of formula (1) to the compound of formula (2) and then converting the compound of formula (2) to the compound of formula (5).

Azetidinone derivatives and method for producing azetidinone and

Method for producing azetidinone and cephalosporin derivatives

The present invention relates to a cephem compound of formula (III) shown in the description. The compound is useful as an intermediate for the synthesis of .beta.-lactam antibiotics of new class and also to a process for producing the same. The cephem compound (III) is produced by reacting a cephem compound of formula (I) with a nitrogen-containing compound of formula (II) under acid-capturing conditions. The process can be performed easily under mild conditions.

Beta-lactam compound and process for production thereof

There are provided new cephem compounds (synisomers) represented by the following general formula (I): ##STR1## wherein R.sup.1 means a lower group, R.sup.2 denotes an ester-forming group of the carboxyl group, and the 4-methylthiazolyl group and the cephem moiety are cis to each other relative to the carbon-carbon double bond of the substituted vinyl group in the side chain at the 3-position of the cephem nucleus. The cephem compounds exhibit strong antibacterial activities not only against resistant strains of bacteria and gram-negative bacteria but also against gram-positive bacteria and moreover have very low toxicity.

Cephem compounds

New cephalosporin derivatives of a general formula (I) and non-toxic salts and non-toxic esters thereof are provided: ##STR1## (wherein R represents an acyclic or cyclic lower alkyl group having 1-6 carbon atoms, which may optionally be substituted by a halogen atom; the steric configuration as asterisked (*) includes an optical-active (R)-form or (S)-form or an optical-inactive (RS)-form; n is 0 or 1, n.sup.1 is 0 to 3, n.sup.2 is 0 to 3; and when n.sup.1 is 0, n.sup.2 is 3; when n.sup.1 is 1, n.sup.2 is 2; when n.sup.1 is 2, n.sup.2 is 1; when n.sup.1 is 3, n.sup.2 is 0). The new derivatives of the formula (I) and non-toxic salts and esters thereof have high bactericidal activity with broad antibacterial spectra, and these are useful as active ingredients in bactericides.

Cephalosporin derivatives and antibiotics containing the same

A new compound, i.e., 14-chlorodaunomycin, and its method of preparation are provided. The new compound, useful as an antitumor agent and as an intermediate in the preparation of (2'R)-4'-O-tetrahydropyranyladriamycin, is obtained by reaction of daunomycin with an alkyl ortho-formate and a brominating agent to produce a 14-bromo-13-dialkylketaldaunomycin, hydrolysis of the latter compound, then adding an excess of a solid metal/chloride to produce an acid addition salt of 14-chlorodaunomycin and concurrently salting out the latter compound from the reaction solution, followed by recovering the 14-chlorodaunomycin acid addition salt.

Method for the synthesis of (2'R)-4'-O-tetra-hydropyranyladriamycim

A class of new caphalosporin compounds (syn-isomer) is now provided, which is useful as antibacterial agent and is represented by the general formula (I) ##STR1## wherein R.sup.1 is an amino group or a protected amino group; R.sup.2 is a lower alkyl group, a carboxymethyl group or a protected carboxymethyl group; R.sup.3 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group; A is an unsubstituted or substituted phenyl group, an unsubstituted or substituted furyl group, an unsubstituted or substituted thiazolyl group or an unsubstituted or substituted 3-lower-alkylthiazolio group, and a pharmaceutically acceptable salt or ester thereof.

Cephalosporin compounds and the production thereof

Cephalosporin compounds having 2-(2-aminothiazol-4-yl)-2{(1S)-carboxyethoxyimino}acetyl group on the side chain at the 7-position thereof and 1-ethylpyridinium-4-ylthiomethyl group on the side chain at the 3-position thereof or non-toxic salts thereof are excellent antibacterial agents for mammals including human. The cephalosporin derivatives have low toxicity.

Antibacterial agent for mammal use comprising cephalosporin derivatives

A new cephalosporin compound is now provided, which is useful as antibacterial agent and is represented by the general formula (I) ##STR1## wherein R.sup.1 is an amino group or a protected amino group; R.sup.2 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group; R.sup.3 is a hydrogen atom, a halogen atom, a lower alkylthio group, a lower alkoxyl group, a vinyl group or a group of the formula: --CH.sub.2 Y where Y is a hydrogen atom, a halogen atom, an acyloxy group, an unsubstituted or substituted heterocyclic thio group or an unsubstituted or substituted pyridinio group, and a pharmaceutically acceptable salt or ester thereof.

Cephalosporin compounds

Disclosed is a novel cephem compound represented by the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and Y are as defined in the specification, which is a useful intermediate for synthesizing various cephalosporin antibiotics having a methoxy group at the 7.alpha.-position thereof. Also disclosed is a process for preparing the same.

Cephem compounds and process for preparing the same

Sodium 7.beta.-(2D-2-amino-2-carboxyethylthioacetamido)-7.alpha.-methoxy-3-(1-met hyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate heptahydrate and a method of obtaining it from the corresponding carboxylate.

Sodium

Disclosed is a novel cephem compound represented by the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are as defined in the specification, which is a useful intermediate for synthesizing various cephalosporin antibiotics having a methoxy group at the 7.alpha.-position thereof. Also disclosed is a process for preparing the same.

Process for preparing 7-.alpha.-methoxycephem compounds

A novel ester of a cephem compound having a carboxyl group at the 4-position in the nucleus; a process for preparing the same by reacting a cephem carboxylic acid or its salt with a halogenide; and a method for removing the protective group for the carboxyl group in the nucleus of a cephem compound by contacting it with an alcohol, or with an organic solvent in the presence of a Lewis acid.

Polychalcogen ester of cephem compound, process for preparing the same

A process for preparing a cephalosporin ester which comprises subjecting an organic halide or an alcohol to reaction with a cephalosporin acid, a cephalosporin acid halide or a salt thereof in the presence of liquid sulfur dioxide.

Process for preparing cephalosporin esters in the presence of liquid

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Yokohama, Japan

Ken Nishihata