Antibiotic compounds

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

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540200, 540350, 548413, 548537, A61K 31395, C07D20500, C07D48704, C07D20700

Patent

active

054788200

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/CT 1393/00217, filed Feb. 2, 1993.
The present invention relates to carbapenems and in particular to such compounds containing a carboxy substituted phenyl group. This invention further relates to processes for their preparation, to intermediates in their preparation, to their use as therapeutic agents and to pharmaceutical compositions containing them.
The compounds of this invention are antibiotics and can be used in the treatment of any disease that is conventionally treated with antibiotics for example in the treatment of bacterial infection in mammals including humans.
Carbapenems were first isolated from fermentation media in 1974 and were found to have broad spectrum antibacterial activity. Since this discovery substantial investigations have been made into new carbapenem derivatives and many hundreds of patents and scientific papers have been published.
The first, and so far the only, carbapenem to be commercially marketed is imipenem (N-formimidoyl thienamycin). This compound has a road spectrum of antibacterial activity.
The present invention provides compounds with a broad spectrum of antibacterial activity including against both Gram positive and negative, aerobic and anaerobic bacteria. They exhibit good stability to beta-lactamases. In addition representative compounds of this invention exhibit a very favourable duration of action.
The carbapenem derivatives referred to herein are named in accordance with the generally accepted semi-systematic nomenclature: ##STR2##
Accordingly the present invention provides a compound of the formula (I): ##STR3## or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof wherein: hydrogen, halo, cyano, C.sub.1-4 alkyl, nitro, hydroxy, carboxy, C.sub.1-4 alkoxy, C.sub.1-4 alkoxycarbonyl, aminosulphonyl, C.sub.1-4 alkylaminosulphonyl, di-C.sub.1-4 alkylaminosulphonyl, carbamoyl, C.sub.1-4 alkylcarbamoyl, di-C.sub.1-4 alkylcarbamoyl, trifluoromethyl, sulphonic acid, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, C.sub.1-4 alkanoylamino, C.sub.1-4 alkanoyl(N-C.sub.1-4 alkyl)amino, C.sub.1-4 alkanesulphonamido and C.sub.1-4 alkylS(O).sub.n -- wherein n is zero, one or two: position ortho to the link to --NR.sup.3 --.
Alkyl when used herein includes straight chain and branched chain substituents for example methyl, ethyl, n-propyl, isopropyl, n-butyl and isobutyl.
Preferably R.sup.1 is 1-hydroxyethyl.
R.sup.2 is hydrogen or C.sub.1-4 alkyl for example methyl, ethyl, n-propyl, isopropyl or n-butyl. Preferably R.sup.2 is hydrogen or methyl and in particular R.sup.2 is methyl.
R.sup.3 is hydrogen or C.sub.1-4 alkyl for example methyl, ethyl, n-propyl, isopropyl or n-butyl. Preferably R.sup.3 is hydrogen.
R.sup.4 and R.sup.5 are the same or different and are selected from hydrogen; halo for example fluoro, bromo or chloro; cyano; C.sub.1-4 alkyl for example methyl, ethyl, n-propyl, isopropyl or n-butyl; nitro; hydroxy; carboxy; C.sub.1-4 alkoxy for example methoxy or ethoxy; C.sub.1-4 alkoxycarbonyl for example methoxycarbonyl, ethoxycarbonyl and n-propoxycarbonyl; aminosulphonyl; C.sub.1-4 alkylaminosulphonyl for example methylaminosulphonyl and ethylaminosulphonyl; di-C.sub.1-4 alkylaminosulphonyl for example di-methylaminosulphonyl, methylethylaminosulphonyl and di-ethylaminosulphonyl; carbamoyl; C.sub.1-4 alkylcarbamoyl for example methylcarbamoyl or ethylcarbamoyl; di-C.sub.1-4 alkylcarbamoyl for example dimethylcarbamoyl or diethylcarbamoyl; trifluoromethyl; sulphonic acid; amino; C.sub.1-4 alkylamino for example methylamino or ethylamino; di-C.sub.1-4 alkylamino for example dimethylamino or diethylamino; C.sub.1-4 alkanoylamino for example acetamido or propionamido; C.sub.1-4 alkanoyl(N-C.sub.1-4 alkyl)amino for example N-methylacetamido; C.sub.1-4 alkanesulphonamido for example methanesulphonamido; and C.sub.1-4 alkylS(O).sub.n -- for example methylthio, methylsulphinyl or methylsulphonyl.
In a particular aspect a suitable class of compounds is that in which R.sup.4 and R.sup.5 are the same or different

REFERENCES:
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Betts, CA 118(9):80721d (1992).
Betts, CA 118(7):59495y (1992).

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