Toyama Chemical Co., Ltd.

Handi-pac, Inc.

Hiroshi Sadaki

Isamu Saikawa

Takihiro Inaba

Hiroyuki Imaizumi

Yasuo Watanabe

Masaru Tai

Hideo Taki

Yoshinori Konishi

Kenji Takeda

Tatsuo Hirakawa

Hirokazu Narita

Isao Myokan

Takashi Nagai

Ryuko Takeno

Shinzaburo Minami

Seishi Morita

Tetsuya Kajita

Yoshikazu Fukuoka

Hirokazu Ochiai

Narita Hirokazu

Novel cephalosporins which has attached to the exomethylene group at the 3-position of the cephem ring a substituted or unsubstituted aryl, acylamino, aromatic heterocyclic, triazolyl or tetrazolyl group, said aromatic heterocyclic group being attached through a carbon-carbon bond and said triazolyl or tetrazolyl group being attached through a carbon-nitrogen bond, and has the following group attached to the amino group at the 7-position: ##STR1## wherein A represents a group of the formula, --CH.sub.2 -- or a group of the formula ##STR2## in which R.sup.5 represents a hydrogen atom or an alkyl group, and the bond.about.represents syn or anti isomer or their mixture; R.sup.3 represents a hydrogen or halogen atom; and R.sup.4 represents a hydrogen atom or an amino group which may be protected or substituted. These cephalosporins have a broad antibacterial spectrum, are stable against .beta.-lactamase produced by bacteria, have a low toxicity, and are well absorbed when administered orally or parenterally.

Cephalosporins, process for producing the same, intermediates thereof

Novel cephalosporins which has attached to the exomethylene group at the 3-position of the cephem ring a substituted or unsubstituted aryl, acylamino, aromatic heterocyclic, triazolyl or tetrazolyl group, said aromatic heterocyclic group being attached through a carbon-carbon bond and said triazolyl or tetrazolyl group being attached through a carbon-nitrogen bond, and has the following group attached to the amino group at the 7-position: ##STR1## wherein A represents a group of the formula, --CH.sub.2 -- or a group of the formula ##STR2## in which R.sup.5 represents a hydrogen atom or an alkyl group, and the bond  represents syn or anti isomer or their mixture; R.sup.3 represents a hydrogen or halogen atom; and R.sup.4 represents a hydrogen atom or an amino group which may be protected or substituted. These cephalosporins have a broad antibacterial spectrum, are stable against .beta.-lactamase produced by bacteria, have a low toxicity, and are well absorbed when administered orally or parenterally.

7-(substituted or unsubstituted amino) 3-substituted methyl-.sup.3

This invention relates to a 7-amino-3-(pyrazinylmethyl)- or (pyridazinylmethyl)-cephalosporins of the formula: ##STR1## wherein R.sup.1 represents a hydrogen atom or a carboxyl-protecting group; R.sup.2 represents a group of the formula: ##STR2## in which R.sup.6 represents a hydrogen atom, a C.sub.1-5 alkyl group or a di-C.sub.1-5 alkylamino group; R.sup.13 represents a C.sub.1-5 alkyl group; and R.sup.28 represents an amino group.

7-amino-3-(pyrazinylmethyl) or (pyridazinylmethyl)-cephalosporins

This invention relates to novel 7-(substituted or unsubstituted amino)-3-substituted methyl-.DELTA..sup.3 -cephem-4-carboxylic acids in which a substituted or unsubstituted 1,2,4-triazolyl or 2-(1,2,3,4-tetrazolyl) group attaches to the exomethylene group at the 3-position of the cephem ring through a carbon-nitrogen bond. These cephalosporins are useful intermediates for producing various novel cephalosporins. Also, this invention concerns a process for producing a compound represented by the formula: ##STR1## which comprises reacting a compound represented by the formula: ##STR2## with an optionally substituted triazole or tetrazole in the presence of an acid or a complex of the acid in an organic solvent at 0.degree. to 80.degree. C.

Novel intermediates of cephalosporins and process for producing

This invention relates to a novel process for producing a 2-(2-aminothiazol-4-yl)glyoxylic acid derivative or a salt thereof which are useful in producing a cephalosporin antibiotic, and to intermediates for said derivative and salt and a process for producing the intermediates.

Novel process for producing 2-(2-aminothiazol-4-yl)glyoxylic acid

The invention relates to antibiotic compounds of the formula: ##STR1## wherein R.sup.1 represents a hydrogen atom or a carboxyl-protecting group; R.sup.2 represents a group of the formula: ##STR2## R.sup.3 represents a hydrogen atom or an alkoxy group; R.sup.4 represents a hydrogen atom or a halogen atom; R.sup.5 represents a hydrogen atom or a protected or unprotected amino group; A represents a group of the formula, --CH.sub.2 -- or a group of the formula, ##STR3## or a group of the formula, ##STR4## and the bond  means that the compound may be a synisomer or an anti-isomer or a mixture thereof.

Antibiotic 7-(thiazolyl)-3-(pyrazinylmethyl) or (pyridazinylmethyl)

This invention relates to a novel process for producing a useful cephalosporin which comprises reacting a thiolo ester compound with a 7-aminocephalosporin in the presence of boron trifluoride or a complex compound thereof. This process enables the cephalosporin to be produced with a high purity in a high yield.

Novel process for producing cephalosporins

Process for producing 2-(2-aminothiazol-4-yl)glyoxylic acid derivative

Novel cephalosporins which has attached to the exomethylene group at the 3-position of the cephem ring a substituted or unsubstituted aryl, acylamino, aromatic heterocyclic, triazolyl or tetrazolyl group, said aromatic heterocyclic group being attached through a carbon-carbon bond and said triazolyl or tetrazolyl group being attached through a carbon-nitrogen bond, and has the following group attached to the amino group at the 7-position: ##STR1## wherein A represents a group of the formula, --CH.sub.2 -- or a group of the formula ##STR2## in which R.sup.5 represents a hydrogen atom or an alkyl group, and the bond  represents syn or anti isomer or their mixture; R.sup.3 represents a hydrogen or halogen atom; and R.sup.4 represents a hydrogen atom or an amino group which may be protected or substituted. These cephalosporins have a broad antibacterial spectrum, are stable against .beta.-lactamase produced by bacteria, have a low toxicity, and are well absorbed when administered orally or parenterally. This invention relates to such novel cephalosporins, processes for producing said cephalosporins, intermediates for producing said cephalosporins, and a process for producing said intermediates.

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Toyama, Japan

Hiroshi Sadaki