Fujisawa Pharmaceutical Company, Ltd.

Sk&f Lab Co.

Yoshiharu Nakai

Takashi Kamiya

Tsutomu Toyonaka Teraji

Kazuo Sakane

Kunihiko Tanaka

Masashi Hashimoto

Teruo Kyoto Oku

Jiro Goto

Osamu Nakaguti

Hidekazu Takeno

Graham J Durant

The present invention involves certain thiazol-4-yl-acetic acid compounds which are valuable intermediates for the preparation of cephem antibiotics. Said intermediates have the following structure: ##STR1## wherein R.sup.1 is an amino or a protected amino group; R.sup.2 is a group of the formula 13 CONH--R.sup.5 or --NHCO--R.sup.5 wherein R.sup.5 is pyridyl, thiazolyl or an isoxazolyl ring having lower alkyl and halogen substituted phenyl substituents, and A is lower alkylene, or a non-toxic salt thereof.

Thiazolylacetic acid derivative

The present invention relates to new 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutically acceptable salts thereof which have antimicrobial activities and to processes for preparation thereof, to pharmaceutical compositions comprising the same, and to a method of using the same therapeutically in the treatment of infectious diseases in humans and animals. This division relates to intermediate compounds, namely amino or amido-thiazolyl, substituted oxyimino disubstituted acetic acid of the formula: ##STR1## wherein R.sup.1 is amino or a protected amino group;

Amino thiazole compounds

A novel compound, useful as an intermediate in the production of compounds of high antimicrobial activity, of the formula: ##STR1## wherein R.sub.a.sup.1 is hydrogen, amino or a protected amino group,

Pyridinyl and pyrimidinyl derivatives

Antibiotic cephalosporin compounds, method of making and pharmaceutical composition thereof represented by the general formula ##STR1## wherein R.sup.1 is amino, lower alkylamino, a protected amino, a protected lower alkylamino, hydroxy or lower alkoxy,

3,7-Disubstituted-3-cephem-4-carboxylic acid compounds and processes for

Amino or amido-thiazolyl, substituted oxyimino disubstituted acetic acid

This invention relates to new 2-azetidinone compounds, which have antimicrobial activities, and to processes for the preparation thereof, and more particularly, this invention provides new 2-azetidinone compounds, especially ones having various substituted carboxyalkyl radicals at the first position and having various group at the fourth position of the azetidinone nucleus, which have antimicrobial activity against various pathogenic microorganisms and are useful as antibiotics in treatment for microbial infections in mammals including human beings and animals.

2-Azetidinone compounds and processes for preparation thereof

3,7-Disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutical salts thereof having antibacterial properties in the treatment of animals and processes for preparing the compounds.

3,7-Disubstituted-3-cephem-4-carboxylic acid compounds

This invention relates to novel compounds having antimicrobial activity of the formula ##STR1## in which R.sup.1 is amino or a protected amino group,

Cephem compounds

This invention relates to novel 7-pyrimidinyl and pyridinyl acetamido cephem derivatives of high antibacterial activity.

Pyrimidinyl cephalosporanic acid derivatives and pharmaceutical

This invention relates to new processes for preparing an imidazole derivative, i.e. cimetidine, by (1) reacting an imidazolylmethylthioethylamine with an amidine or (2) reacting a N-cyano-N'-imidazolylmethylthioethyl formamidine with methylamine or (3) reacting a N-methyl-N'-imidazolylmethylthioethyl formamidine with cyanamide.

Process for preparing an imidazole derivative

This invention relates to new 2-azetidinone compounds, which have antimicrobial activities, and to processes for the preparation thereof, and more particularly, this invention provides new 2-azetidinone compounds, especially ones having various substituted carboxyalkyl radicals at the first position and having various groups at the fourth position of the azetidinone nucleus, which have antimicrobial activities against various pathogenic microorganisms and are useful as antibiotics in treatment for microbial infections in mammal including human being and animals.

The present invention relates to new 3,7 disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutically acceptable salts thereof. More particularly, it relates to new 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and pharmaceutically acceptable salts thereof which have antimicrobial activities and to processes for preparation thereof, to pharmaceutical composition comprising the same, and to a method of using the same therapeutically in the treatment of infectious diseases in human being and animals.

3,7-Disubstituted-3-cephem-4-carboxylic acid compounds and

The invention relates to novel amino or acylamino-substituted pyrimidinyl cephalosporanic acid derivatives and pharmaceutically acceptable salts thereof, of antibacterial activity, to processes for the preparation thereof, and to pharmaceutical compositions comprising the novel cephalosporanic acid derivatives.

Amino or acylamino-substituted pyrimidinyl cephalosporanic acid

A process for preparing an azetidinone of the formula: ##STR1## which comprises reacting a C-unsubstituted methyleneamine of the formula: ##STR2## with R.sup.2 --CH.sub.2 COOH, its acid halide or anhydride, in the presence of boron trihalide and an organic base, wherein R.sup.1 is an organic residue bearing a carboxy group or its derivative and R.sup.2 is azido, substituted amino, halogen, acyloxy, alkoxy, aryloxy or aralkoxy.

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Otsu, Japan

Yoshiharu Nakai