Cephalosporins

• US 5,538,963 A
• Filed: 09/27/1994
• Issued: 07/23/1996
• Est. Priority Date: 06/25/1991
• Status: Expired due to Fees

• Current Assignee: Hoechst Marion Roussel Incorporated (Sanofi )
• Original Assignee: Roussel Uclaf
• Inventors: Humbert, Daniel, Chantot, Jean-Francois, Teutsch, Jean-Georges, D'Ambrieres, Solange G.
• Primary Examiner(s): Rizzo, Nicholas
• Application Number:
  US08/313,745
• Time in Patent Office: 665 Days
• Field of Search: 540/214, 540/215, 540/227, 540/226, 514/210
• US Class Current: 514/210.05
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: C07D 513/04 Ortho-condensed systems

Abstract

The syn isomer of a compound of the formula ##STR1## in the R or S form or a mixture of R and S forms wherein selected from the group consisting of ##STR2## and their non-toxic, pharmaceutically acceptable acid addition salts wherein the substituents are defined as in the specification having antibacterial activity and their preparation.

Claims

1. The syn isomer of a quaternary ammonium compound of the formula ##STR41## in the R or S form or a mixture of R and S forms wherein R₁ is selected from the group consisting of ##STR42## R and R'"'"' are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halogen, Q and Q'"'"' are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, P, P'"'"' and P" are individually alkyl of 1 to 4 carbon atoms optionally substituted by one of the substituents of R and R'"'"', the dotted line indicating that P and P'"'"' can optionally form with the nitrogen atom to which they are attached a heterocycle with 5 or 6 ring members, or R₁ is --S--Het wherein Het is selected from the group consisting of thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadizaolyl, oxadizaolyl, tetrazolyl, imidazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl and dihydrotriazinyl, all optionally substituted by at least one substituent selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkyl or dialkylamino, hydroxy, oxo, alkylthio, free, esterified or salified carboxy and carboxyalkyl, X is a single bond or ##STR43## in E or Z form, R_b and R_c are individually hydrogen or acyl, A and A'"'"' are individually selected from the group consisting of an equivalent of alkali metal or alkaline-earth metal, magnesium, ammonium and amino or A and A'"'"' are the remainder of an easily cleavable ester group or --CO₂ A is --CO₂ -- and their non-toxic, pharmaceutically acceptable acid addition salts.

2. A compound of claim 1 wherein R₁ is, selected from the group consisting of ##STR44## or S-Het wherein Het is selected from the group consisting of 1,2,4, 1,3,4 or 1,2,3-thiadiazolyl;

thiazole-2-yl;

imidazol-2-yl;

2-methyl-1,3,4-thiadiazol-5-yl;

1-methyl-tetrazol-5-yl ##STR45##

3. An antibacterial composition comprising an antibacterially effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.

4. A method of combatting bacterial infections in warm-blooded animals comprising administering to warm-blooded animals in need thereof an anti-bacterially effective amount of a compound of claim 1.