Cephem derivatives

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

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Details

540227, C07D50156, A61K 31545

Patent

active

058830898

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/JP96/01406 filed May 24, 1996.


BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention relates to novel .beta.-lactam antibiotics and pharmaceutically acceptable salts and esters thereof. More particularly, the present invention relates to novel cephem compounds having antibacterial activity and pharmaceutically acceptable salts and esters thereof.
2. Background Art
Cephem antibiotics exhibit excellent antibacterial activity with low toxicity for mammals. They are therefore very important to the treatment of infectious diseases in mammals. In recent years, cephem derivatives having an aminothiazolylacetyl group at the 7-position of the cephem ring have been found to have potent antibacterial activity and stability against .beta.-lactamase, leading to numerous studies and developments in these cephem derivatives. Various semi-synthetic cephem compounds have already been put on the market and clinically used as therapeutic agents for various infectious diseases.
However, among these compounds, those usable as a therapeutic agent having antibacterial activity against Pseudomonas aeruginosa and Myxomycetes are limited. Further, these compounds are unstable against .beta.-lactamase produced by resistant bacteria and have drawbacks such as low antibacterial activity against the resistant bacteria which have posed a clinical problem these days. Furthermore, many cephem antibiotics have been developed for use in injections, and it is often pointed out that, in the case of oral administration, the cephem antibiotics have low absorption ratio and, hence, have unsatisfactory efficacy.
Specific examples of .beta.-lactam compounds known in the art include Cefixime, Cefdinir, ME 1207 (Cefditren pivoxil), and ME 1206 (Cefditren).
However, no compounds having a .beta.-substituted vinyl side chain, especially a .beta.-(substituted or unsubstituted have been reported so far as the present inventors know.


SUMMARY OF THE INVENTION

The present inventors have now found that compounds having a at the 3-position of the cephem ring have antibacterial activity against a very wide spectrum of bacteria and potent antibacterial activity against Gram-positive bacteria, Gram-negative bacteria, and resistant bacteria.
Thus, an object of the present invention is to provide novel cephem derivatives having potent antibacterial activity against a wide spectrum of bacteria.
Another object of the present invention is to provide pharmaceutical compositions comprising the cephem derivative of the present invention.
A further object of the present invention is to provide a method for treating infectious diseases, comprising the step of administering the cephem derivative of the present invention.
The compounds according to the present invention are cephem derivatives represented by the following formula (I): ##STR2## wherein X represents CH or N, R.sup.1 represents hydrogen or an amino protective group, atoms may be substituted by halogen, carboxyl, C.sub.1-4 alkoxycarbonyl, carbamoyl, N-C.sub.1-4 alkylcarbamoyl, cyano, amino, or C.sub.1-4 alkylamino; C.sub.2-4 alkenyl; C.sub.2-4 alkynyl; C.sub.3-7 cycloalkyl; or a hydroxy protective group, carboxyl protective group, represent C.sub.1-4 alkylcarbonyl, or C.sub.1-4 alkylsulfonyl; group selected from the group consisting of hydroxyl, C.sub.1-4 alkoxy, mercapto, C.sub.1-4 alkylthio, cyano, halogen, carboxyl, C.sub.1-4 alkoxycarbonyl, carbamoyl, N-C.sub.1-4 alkylcarbamoyl, formyl, alkylcarbonyl, hydroxyimino, C.sub.1-4 alkoxyimino, amino, formylamino, C.sub.1-4 alkylcarbonylamino, halogen-substituted C.sub.1-4 alkylcarbonylamino, carbamoyloxy, N-C.sub.1-4 alkylcarbamoyloxy, C.sub.1-4 alkylsulfonylamino, ureido, N-C.sub.1-4 alkylureido, C.sub.1-4 alkylcarbonylamino, and imino-C.sub.1-4 alkylamino; alkylene where one or more methylene groups in this alkylene group may be replaced by --NH--, --O--, --S--, or --CO--, C.sub.1-6 alkyl, or substituted C.sub.1-6 alkylene, and
The compounds represented by the formula (I) have antibacterial activity against a very

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