Toyama Chemical Co., Ltd.

Handi-pac, Inc.

Yasuo Watanabe

Isamu Saikawa

Hirokazu Narita

Hiroyuki Imaizumi

Takihiro Inaba

Hiroshi Sadaki

Yoshinori Konishi

Shinzaburo Minami

Masaru Tai

Hideo Taki

Tatsuo Hirakawa

Kaishu Momonoi

Yozo Todo

Hirokazu Ochiai

Kazuya Hayashi

Kenji Takeda

Isao Myokan

Yoshiharu Murotani

Hirohiko Fukuda

Takashi Nagai

Yoshikazu Fukuoka

Toshio Hayashi

Osamu Yoshino

Isamu Takakura

Jun Nitta

Masahiro Takahata

Hideyoshi Nagaki

Isao Kitayama

Nobuyuki Matsubara

Yoriko Nagai

Narita Hirokazu

Masahiro Tadahata

Shosaku Kato

Sadao Sotani

Shunjiro Misumi

Quinolonecarboxylic acid derivatives or salts thereof

Quinolone- or naphthylidone-carboxylic acid derivates or their salts

Sustained-release oral ointment

A penam derivative represented by the following general formula or a salt thereof: ##STR1## wherein R.sup.1 represents a hydrogen atom, an amino-protecting group or an acyl group; R.sup.2 represents a hydrogen atom or a lower alkyl group; R.sup.3 represents a hydrogen atom, a lower alkoxy group, a lower alkylthio group or a formamido group; R.sup.4 represents an protected or unprotected carboxyl group or a carboxylato group; R represents a group of the formula, --NHR.sup.5 or --NR.sup.5 R.sup.6 (in which R.sup.5 and R.sup.6, which may be the same or different, represent protected or unprotected hydroxyl groups, cyano groups, sulfo groups, or unsubstituted or substituted lower alkyl, aryl, acyl, carbamoyl, sulfamoyl, lower alkylsulfonyl or heterocyclic groups) or a group of the formula, --N.dbd.CR.sup.7 R.sup.8 (in which R.sup.7 and R.sup.8, which may be the same or different, represent hydrogen atoms or protected or unprotected carboxyl groups, cyano groups or unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl, aryl, amino, acyl, acyloxy, carbamoyl, carbamoyloxy, sulfamoyl, lower alkylthio, ureido or heterocyclic groups, or R.sup.7 and R.sup.8 may form a cycloalkene or a heterocyclic ring with the carbon atom to which R.sup.7 and R.sup.8 are attached); and n represents 1 or 2. The above penam derivative or its salt is very effective as antibacterial agents.

Penam derivatives and salts thereof, process for producing the same and

A penam derivative represented by the following general formula or a salt thereof: ##STR1## wherein R.sup.1 represents a hydrogen atom, an amino-protecting group or an acyl group; R.sup.2 represents a hydrogen atom or a lower alkyl group; R.sup.3 represents a hydrogen atom, a lower alkoxy group, a lower alkylthio group or a formamido group; R.sup.4 represents a protected or unprotected carboxy group or a craboxylato group; R represents a group of the formula, --NHR.sup.5 or --NR.sup.5 R.sup.6 (in which R.sup.5 and R.sup.6, which may be the same or different, represent protected or unprotected hydroxyl groups, cyano groups, sulfo groups, or unsubstituted or substituted lower alkyl, aryl, acyl, carbamoyl, sulfamoyl, lower alkylsulfonyl or heterocyclic groups) or a group of the formula, --N.dbd.CR.sup.7 R.sup.8 (in which R.sup.7 and R.sup.8, which may be the same or different, represent hydrogen atoms or protected or unprotected carboxyl groups, cyano groups or unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl, aryl, amino, acyl, acyloxy, carbamoyl, carbamoyloxy, sulfamoyl, lower alkylthio, ureido or heterocyclic groups, or R.sup.7 and R.sup.8 may form a cycloalkene or a heterocyclic ring with the carbon atom to which R.sup.7 and R.sup.8 are attached); and n represents 1 or 2. The above penam derivative or its salt is very effective as antibacterial agents.

Penam derivatives and salts thereof, and antibacterial agent comprising

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 a novel 4-oxo-1,4-dihydronicotinic acid derivative ##STR1## or a salt thereof, wherein R.sup.1 is hydrogen or carboxyl-protecting group;

4-oxo-1,4-dihydronicotinic acid derivatives, salts thereof, and

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

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)

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

Toyama, Japan

Yasuo Watanabe