Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-07-31
1998-10-27
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540227, C07D50156, A61K 31545
Patent
active
058278451
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/JP94/01618 filed Sep. 29, 1994
TECHNICAL FIELD
This invention relates to novel cephem compounds having useful antibacterial activities, more particularly cephalosporin derivatives and pharmaceutically acceptable salts or esters thereof.
BACKGROUND ART
Antibiotics of cephalosporin type have excellent antibacterial activities against bacteria and exhibit low toxicity to mammals, and hence they are a medicine which is very much effective in therapeutic treatments of bacterial infections in mammals.
A variety of semi-synthetic cephalosporin derivatives having a wide range of antibacterial activities against gram-positive bacteria and gram-negative bacteria are already synthetised and available commercially, and they are now used clinically as a therapeutic agent for various bacterial infections. Among the known cephalosporin derivatives, however, such cephalosporin derivatives which can exhibit a high antibacterial activity against Pseudomonas aeruginosa and Proteus species are few. Many of the known cephalosporin derivatives have further such drawback that they are unstable to the .beta.-lactamase as produced by some resistant strains of bacteria and exhibit poor antibacterial activities against various resistant strains of bacteria which have now been a target of the clinical treatments of the bacterial infections. They can also have another certain drawbacks. Besides, many of the existing antibacterial compounds of the cephem series have been exploited mainly for use as injections and thus they can have such drawback that when they are orally administered, their rate of absorption in the living body is poor so that they do not exhibit a sufficiently high efficacy in the therapeutic treatments of bacterial infections.
In recent years, researches and exploitions have been made of such cephalosporin derivatives having amino-thiazolylacetyl group at the 7-position of the cephem ring since many of said cephalosporin derivatives can exhibit high antibacterial activities and a stability to .beta.-lactamase.
For example, the known cephem compounds having the aminothiazolylacetyl group at the 7-position and a .beta.-substituted or unsubstituted vinyl group at the 3-position of the cephem ring include Cefixime having the following formula (A) ##STR2## and Cefdinir having the following formula (B) ##STR3##
Also, there is known a cephem compound (syn-isomer) represented by the following general formula (C) ##STR4## wherein R.sup.1 is an amino group or a protected amino group, R.sup.2 is a lower alkyl group, carboxymethyl group or a protected carboxymethyl group, R.sup.3 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group, and A stands for phenyl group, a lower alkyl-phenyl group, a lower alkoxy-phenyl group, or a halo-phenyl group, or furyl group, nitro-furyl group, or a halo-furyl group or thiazolyl group, a lower alkyl-thiazolyl group or a halo-thiazolyl group, or a 3-lower alkyl-thiazolio group which may further bear one lower alkyl substituent at a position other than the 3-position of the thiazolyl ring and has an anionic counter-ion associated with the quarternary nitrogen atom at the 3-position of the thiazolio group, or a salt or an ester of said cephem compound (see Japanese patent publication No. Hei-3-64503, European patent No. 0175610 and U.S. Pat. No. 4,839,350). One example of the cephem compound of the general formula (C) is 5-yl)vinyl!-3-cephem-4-carboxylic acid (syn-isomer, cis-isomer), which is abbreviated as ME1206 compound hereinafter. Pivaloyloxymethyl ester of this ME1206 compound, which is abbreviated as ME1207 compound hereinafter, is known under a common name of "Cefditoren pivoxil".
Furthermore, syn-isomer of a cephem compound represented by the following general formula (D) ##STR5## wherein R.sup.1 is a lower (C.sub.1 -C.sub.6)alkyl group, and R.sup.2 is an ester-forming group cleavable by hydrolysis in vivo, and wherein the 4-methylthiazolyl group and the cephem ring are in "cis"-position around the carbon-carbon double bond of the substituted
Atsumi Kunio
Iwamatsu Katsuyoshi
Shibahara Seiji
Shiokawa Sohjiro
Tamura Atsushi
Ford John M.
Meiji Seika Kaisha Ltd.
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