Toyama Chemical Co., Ltd.

Handi-Pac, Inc.

Takihiro Inaba

Isamu Saikawa

Hiroyuki Imaizumi

Hiroshi Sadaki

Shuntaro Takano

Yasuo Watanabe

Ryuko Takeno

Chosaku Yoshida

Masaru Tai

Hideo Taki

Yoshinori Konishi

Keiichi Tanaka

Kenji Takeda

Shinji Makino

Tomoya Shimotori

Tatsuo Hirakawa

Seishi Morita

Hirokazu Narita

Yukihiko Aikawa

Yoichi Taniguchi

Isao Myokan

Takashi Nagai

Ichiro Oshio

Kiyoshi Tanaka

Shinzaburo Minami

Hirohiko Fukuda

Yoshiharu Murotani

Tetsuya Kajita

Yoshikazu Fukuoka

Junichi Yoshida

Hirokazu Ochiai

Hideyoshi Nagaki

Narita Hirokazu

Autoimmune diseases, cell adhesion inhibition and immunomodulation are treated or effected by a method, comprising, treating a patient with a therapeutically effective amount of a 4H-1-benzopyran-4-one compound represented by the following formula or a salt thereof: ##STR1## wherein R.sup.1 is an unsubstituted or halogen-substituted alkyl, alkenyl or aryl group; R.sup.2 is a hydrogen atom or an alkyl or acyl group; R.sup.3 is a hydrogen or halogen atom or a cyano, azido, carboxyl, hydroxyl, formyl or alkoxycarbonyl group or a substituted or unsubstituted alkyl, alkoxy, phenoxy, cycloalkyl, carbamoyl, amino or phenyl group; R.sup.4 is a hydrogen or halogen atom, a nitro, cyano, carboxyl, acyl, hydroxyl or alkoxycarbonyl group, or a substituted or unsubstituted alkyl, alkoxy, alkylthio, phenylthio, alkynyl, alkenyl, sulfamoyl, alkanesulfonyl, alkanesulfonyl, amidino, phenyl or heterocyclic group or a group of the formula ##STR2## where R.sup.6 is a hydrogen atom, a hydroxyl, cyano or alkoxycarbonyl group or a substituted or unsubstituted alkyl, cycloalkyl, phenyl, amino, acyl, carbamoyl, alkanesulfonyl, iminomethyl or amidino group and R.sup.7 is a hydrogen atom or a substituted or unsubstituted alkyl, alkoxy, phenyl, cycloalkyl or heterocyclic group, or R.sup.6 and R.sup.7, when taken together with the nitrogen atom to which the two are bonded, form a 3- to 7-membered, substituted or unsubstituted heterocyclic group; R.sup.5 is a substituted or unsubstituted phenyl, thienyl, furyl or pyridyl group; Z is an oxygen or sulfur atom or an imino group; and the broken line means a single or double bond.

Immunomodulator, cell adhesion inhibitor, and agent for treating, and

Immunomodulator, cell adhesion inhibtor, and agent for treating, and

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

This invention relates to a 4H-1-benzopyran-4-one derivative represented by the formula: ##STR1## or a salt thereof, a process for producing the same and a pharmaceutical composition comprising the same as active ingredient.

4H-1-benzopyran-4-one derivative or its salt, process for producing the

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

The invention relates to a process for producing a cephalosporin of the formula ##STR1## by reacting the compound ##STR2## with the compound ##STR3## in the presence of boron trifluoride or a complex thereof.

Novel process for producing a cephalosporin

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

This invention relates to a novel aminothiazole intermediate for production of a cephalosporin of antibiotic activity.

Aminothiazole intermediate for a cephalosporin

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.

Cephalosporins

Growing community of inventors

Namerikawa, Japan

Takihiro Inaba