Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1992-02-26
1994-08-09
Rizzo, Nicholas S.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540222, 540225, C07D50138, A61K 31545
Patent
active
053366735
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to novel cephalosporins and pharmaceutically acceptable salts thereof, which are useful as antibacterial agents. The invention also relates to processes for the preparation of the same, to a pharmaceutical composition containing at least one of the same as active ingredients and to a use of the same for treatment of diseases caused by bacterial infection in human beings and animals.
BACKGROUND OF THE INVENTION
Hereto, it has been known that as antibiotics a great variety of cephalosporins having the basic skeleton of the nucleus of the formula(A): ##STR4## have effective antibacterial activities and are widely used as antimicrobial agents for infectious diseases caused by various Gram positive and Gram negative strains.
A variety of cephalosporins whose 7-position has 2-aminothiazolyl acetamino group substituted with .alpha.-oxyimino group have been known. Particularly, the following compounds exhibiting strong antibacterial activities against the enterobacteria have been reported: Cefotaxime in U.S. Pat. Nos. 4,152,432 and 4,098,888; Cefmenoxime in U.S. Pat. 4,098,888 and 4,476,122; Ceftriaxone in U.S. Pat. No. 4,327,210; Ceftazidime in U.S. Pat. Nos. 4,258,041 and 4,329,453.
These compounds, however, show relatively weak antibacterial activities against Staphylococcus when compared with Cephaloridine in French Patent No. 1,384,197 or Cefazoline in U.S. Pat. No. 3,516,997.
Moreover, Ceftazidime exhibits poor antibacterial activity against Staphylococcus, although its antibacterial activity against Pseudomonas is relatively stronger than that of other known cephalosporins.
The present inventors have conducted intensive research to prepare cephalosporins having improved antibacterial activities against Staphylococcus with strong antibacterial activities against Pseudomonas. As a result of prolonged studies on numerous cephalosporins, we found the 3-substituted cephem compounds show superior antibacterial activities against both of Staphylococcus and Pseudomonas.
SUMMARY OF THE INVENTION
An object of the invention is to provide novel cephalosporins represented by the formula (I): ##STR5## wherein,
R.sub.1 represents a C.sub.1 .about.C.sub.4 alkyl group or ##STR6## wherein, R.sub.2 and R.sub.3, independently, represent hydrogen or a C.sub.1 .about.C.sub.3 alkyl group and R.sub.4 represents hydrogen or a C.sub.1 .about.C.sub.4 alkyl group;
R.sub.1a represents hydrogen or an amino-protecting group;
Q represents CH or N; and
the substituent of the formula ##STR7## represents a saturated or unsaturated heterocyclic group containing 1 to 4 nitrogen atoms of which one must be substituted with amino group to form quaternary ammonium, and oxygen or sulfur atoms, or a fused heterocyclic group thereof formed together with a substituted or unsubstituted benzene or optional heterocyclic group, and a pharmaceutically acceptable salt thereof.
Another object of the invention is to provide processes for preparing the cephalosporins of the formula (I).
Another object of the invention is to provide pharmaceutical compositions containing at least one compound of cephalosporins as active ingradients.
Another object of the invention is to provide a use of cephalosporins of the formula (I) for treatment of the diseases caused by bacterial infection.
DETAILED DESCRIPTION OF THE INVENTION
The novel cephalosporins according to the invention may be represented by the following formula (I): ##STR8## wherein,
R.sub.1 represents a C.sub.1 .about.C.sub.4 alkyl group or ##STR9## wherein, R.sub.2 and R.sub.3, independently, represent hydrogen or a C.sub.1 .about.C.sub.3 alkyl group and R.sub.4 represents hydrogen or a C.sub.1 .about.C.sub.4 alkyl group;
R.sub.1a represents hydrogen or an amino-protecting group;
Q represents CH or N; and
the formula ##STR10## represents a saturated or unsaturated heterocyclic group containing 1 to 4 nitrogen atoms of which one must be substituted with an amino group to form quaternary ammonium, and oxygen or sulfur atoms, or a fused heterocyclic
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Choi Young K.
Kim Myoung G.
Moon Chi J.
Oh Sea H.
Park Nam J.
Dae Woong Pharmaceutical Co., Ltd.
Rizzo Nicholas S.
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