Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-09-06
1996-11-26
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540214, A61K 3139, A61K 3154, C07D51314, C07D51322
Patent
active
055785921
DESCRIPTION:
BRIEF SUMMARY
This invention relates to novel .beta.-lactam compounds, their preparation and their use, and in particular to a novel class of cephalosporins. These compounds have antibacterial properties, and are therefore of use in the treatment of bacterial infections in humans and animals caused by a wide range of organisms.
We have now found a particularly advantageous class of polycyclic compounds based upon a cephalosporin nucleus.
The present invention provides a compound of formula (I) or a salt thereof: ##STR2## wherein R.sup.1 is hydrogen, methoxy or formamido; cephalosporin; readily removable carboxy protecting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group; substituent group; bond between the two carbon atoms shown; of formula: ##STR3## wherein X represents --O-- or --NR.sup.8 --, wherein each R.sup.8 may be the same or different and independently represents hydrogen or a substituent group, or two groups R.sup.8 may be linked into a ring system, or any two adjacent--CR.sup.8.sub.2 -- units may be replaced by a --CR.sup.8 .dbd.CR.sup.8 -- unit, and wherein n is an integer 1 to 7, m is 0, 1, 2 or 3.
In compounds of formula (I) wherein R.sup.1 is formamido, the formamido group can exist in conformations wherein the hydrogen atoms of the --NH--CHO moiety are cis- or trans-; of these the cis conformation normally predominates.
Since the compounds of the present invention are intended for use as therapeutic agents for antibacterial use in pharmaceutical compositions, it will be readily appreciated that preferred compounds within formula (I) are pharmaceutically acceptable, i.e. are compounds of formula (Ia) or pharmaceutically acceptable salts or pharmaceutically acceptable in vivo hydrolysable esters thereof: ##STR4## wherein R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.6, and R.sup.7 are as defined with respect to formula (I) and the group CO.sub.2 R.sup.11 is CO.sub.2 R.sup.3 where CO.sub.2 R.sup.3 is a carboxy group or a carboxylate anion.
Accordingly, the present invention provides a compound of formula (Ia) or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof, for use as a therapeutic agent, and in particular an in vivo hydrolysable ester thereof for use as an orally administrable therapeutic agent.
The present invention further provides a compound of formula (Ia) or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof, for use in the treatment of bacterial infections, more particularly an in vivo hydrolysable ester thereof for use in the oral treatment of bacterial infections.
The present invention also includes a method of treating bacterial infections in humans and animals which comprises the administration of a therapeutically effective amount of an antibiotic compound of the formula (Ia) or a pharmaceutically acceptable in vivo hydrolysable ester thereof, in particular the oral administration of a therapeutically effective amount of an in vivo hydrolysable ester.
In addition, the present invention includes the use of a compound of formula (Ia) or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof, for the manufacture of a medicament for the treatment of bacterial infections, in particular the use of an in vivo hydrolysable ester for the manufacture of a medicament for the oral treatment of bacterial infections.
Those compounds of the formula (I) wherein R.sup.3 is a readily removable carboxy protecting group other than a pharmaceutically acceptable in vivo hydrolysable ester or which are in non-pharmaceutically acceptable salt form are primarily useful as intermediates in the preparation of compounds of the formula (Ia) or a pharmaceutically acceptable salt or pharmaceutically acceptable in vivo hydrolysable ester thereof.
Suitable readily removable carboxy protecting groups for the group R.sup.3 include groups forming ester derivatives of the carboxylic acid, including in vivo hydrolysable esters. The derivative is preferably one which may readily be cleaved in vivo.
Also included within the sco
REFERENCES:
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Chemical Abstracts, vol. 103 No. 3 Jul. 22, 1985.
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Burton George
Elliott Richard L.
Ford John M.
Ginsburg Paul H.
Ling Lorraine B.
Pfizer Inc.
Richardson Peter C.
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