Cephalosporin compounds, and antibacterial agents

• US 4,822,786 A
• Filed: 06/17/1987
• Issued: 04/18/1989
• Est. Priority Date: 07/01/1986
• Status: Expired due to Fees

• Current Assignee: Kaken Pharmaceutical Company Limited
• Original Assignee: Kaken Pharmaceutical Company Limited
• Inventors: Zama, Yoshiyuki, Yokoyama, Masaaki, Sekine, Keiji, Ishiyama, Nobuo, Hirose, Masao, Asano, Taiji, Naito, Takanobu, Senda, Hisato, Sanai, Shigeru, Saita, Tsuneo
• Primary Examiner(s): Rizzo, Nicholas S.
• Application Number:
  US07/063,077
• Time in Patent Office: 671 Days
• Field of Search: 540/225, 540/222, 540/227, 514/202, 514/203, 514/206
• US Class Current: 514/202
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 501/00 Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula: , e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Abstract

A cephalosporin compound having the formula: ##STR1## wherein R₁ is a hydrogen atom, a halogen atom, a methoxy group, a substituted or unsubstituted vinyl group, or --CH₂ --A wherein A is a hydrogen atom, an azido group, an acyloxy group, a carbamoyloxy group, a subsituted or unsubstituted heterocyclic group (wherein the hetrocyclic ring is a 5- or 6-membered heterocyclic ring having from 1 to 4 oxygen, nitrogen or sulfur atoms), or a substituted or unsubstituted heterocyclic thio group (wherein the heterocyclic ring is a monocyclic or bicyclic heterocyclic ring having from 1 to 5 oxygen, nitrogen or sulfur atoms), or a pharmaceutically acceptable salt thereof.

Claims

1. A cephalosporin compound having the formula:

##STR44## wherein R₁ is --CH₂ --A wherein A is tetrazolyl, thiazolylthio, isothiazolylthio, thiadiazxolylthio, triazolylthio, triazinylthio, tetrazxolylthio, triazolylpyrimidinylthio, pyridinium-4-ylthio or 2,3-cyclopenteno-pyridinium-4ylthio group which is unsubstituted or substituted hby one to three groups selected from the group consisting of a C_1-4 alkyl group, a carboxymethyl group, a C_1-4 alkoxycarbonylmethyl group, a hydroxy-(C_1-4)alkyl group, a di-(C_1-4)alkylamino-(C_1-4)alkyl group, a carboxyl group, a hydroxyl group, an oxo group and an amino group, or a pharmaceutically acceptable salt thereof.

2. (6R, 7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(1,5-dihydroxy-4-pyridon-2-ylmethoxyimino)acetamido]-3-(1,2,3-thiadiazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid or a pharmaceutically acceptable salt thereof, according to claim 1.

3. (6R, 7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(1,5-dihydroxy-4-pyridon-2-ylmethoxyimino)acetamido]-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid or a pharmaceutically acceptable salt thereof, according to claim 1.

5. (6R, 7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(1,5-dihydroxy-4-pyridon-2-ylmethoxyimino)acetamido]-3-(5-methyl-s-triazolo[1,5-a]pyrimidin-7-ylthiomethyl)-3-cephem-4-carboxylic acid or a pharmaceutically acceptable salt thereof, according to claim 1.

6. An antibacterial pharmaceutical composition containing an antibacterially effective amount of a cephalosporin compound of the formula I as defined in claim 1 or a pharmaceutically acceptable salt thereof.

7. A method of treating infectious disease which comprises administering an antibacterially effective amount of a cephalosporin compound of the formula I as defined in claim 1 to an animal or human being.

4. (6R, 7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(1,5-dihydroxy-4-pyridon-2-ylmethoxyimino)acetamido]-3-(1-methylpyridinium-4-ylthiomethyl)-3-cephem-4-carboxylate,