Cephem compounds, their production and use

Details Cephem compounds, their production and use Cephem compounds, their production and use

1997-07-29

1999-09-07

Berch, Mark L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540225, C07D50124, A61K 31545

Patent

active

059487747

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
This invention relates to a novel cephem compound having excellent antibacterial activities on a broad range of Gram-positive and Gram-negative bacteria, especially Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA), to a method of producing the compound and to an antibacterial composition containing the compound.
2. Description of Related Art
Various cephem compounds having, at the 7-position, 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-oxyiminoacetamido group, and having, at the 3-position, pyridiniothiovinyl group, have been reported in JPA S59(1984)-130292 and JPA H6(1994)-206886. In JPA S59(1984)-130292, however, while aminothiadiazolyl (lower) alkanoylamino having a lower alkoxyimino as the substituent at the 7-position of the cephem compound is disclosed, no description is found that the lower alkoxy may optionally be substituted with fluorine. And, in JPA H6(1994)-206886, only 2-(5-amino-1,2,4-thiadiazol-3-yl) or (2-aminothiazol-4-yl)-2(Z)-hydroxyiminoacetamido group is described as the substituents at the 7-position of the cephem compound, and no description on cephem compounds having 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-fluorine substituted lower alkyloxyiminoacetamido group and their effect is found at all.
So far known cephem compounds are not sufficiently satisfactory in the range and strength of antibacterial activities, especially, in conventional cephalosporin compounds, antibacterial activities against Staphylococcus aureus and methicillin resistant Staphylococcus aureus (MRSA) are not sufficiently satisfactory, and creation of novel compounds overcoming this point has been desired.


SUMMARY OF THE INVENTION

Taking the foregoing circumstances into consideration, the present inventors conducted diligent studies extensively and synthesized, for the first time, a cephem compound characterized by having, at the 3-position of its cephem nucleus, a group of the formula ##STR2## wherein R.sup.3 is an optionally substituted hydrocarbon group, and the ring A may optionally have further substituent(s), and, at the 7-position, a group of the formula: ##STR3##
wherein R.sup.1 is an optionally protected amino group, and R.sup.2 is a fluoro-lower-alkyl group, or an ester or salt thereof, and further found that the compound thus synthesized showed unexpectedly broadly excellent antibacterial activities against Gram-negative bacteria and against Gram-positive bacteria including Staphylococcus aureus and MRSA. Based on these findings, the present invention was accomplished.
More specifically, the present invention relates to: ##STR4## wherein R.sup.1 is an optionally protected amino group; R.sup.2 is a fluoro-lower-alkyl group; R.sup.3 is an optionally substituted hydrocarbon group; and the ring A may optionally have further substituent(s) or an ester or salt thereof, ##STR5## wherein symbols are of the same meaning as described above, or an ester or salt thereof. comprises reacting a compound of the formula: ##STR6## wherein symbols are of the same meaning as defined above, or an ester or salt thereof, with carboxylic acid of the formula: ##STR7## wherein symbols are of the same meaning as defined above, or a salt or reactive derivative thereof, then, upon necessity, by removing the protective group. (4) a method of producing the compound described in (1) above, which comprises reacting a compound of the formula: ##STR8## wherein symbols are of the same meaning as defined above, or an ester or salt thereof, with a compound of the formula, R.sup.3 --X, (wherein X is a leaving group and R.sup.3 is of the same meaning as defined above, then, upon necessity, by removing the protective group, compound described in (1) above and pharmaceutically acceptable carrier, diluent or excipient, and comprises administering an effective amount of a compound described in (1) above optionally together with a pharmaceutically acceptable carrier, diluent or excipient to a patient suffering from a bacterial infection, and antibacterial composition

REFERENCES:
patent: 4761410 (1988-08-01), Takaya

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