1-Carba-2-penem-3-carboxylic acid
AssigneeMerck & Co., Inc.
InventorsLovji D. Cama, Burton G. Christensen
Life of this patent
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Abstract
Disclosed are 1-carba-2-penem-3-carboxylic acids of the following structure: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, aryl, and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
Claims41
A compound having the structural formula:
- ##STR590## and the pharmaceutically acceptable salts thereof wherein R.sup.1, R.sup.2 and R.sup.3 are independently selected from the group consisting of:
- hydrogen, mono-substituted and unsubstituted:
- alkyl having from 1 to 10 carbon atoms, alkenyl and akynyl having from 2 to 10 carbon atoms, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl and cycloalkenylalkyl wherein the preceding cycloalkyl or cycloalkenyl moieties comprise 3 to 6 carbon atoms and the alkyl or alkenyl moieties comprise 1 to 6 carbon atoms, phenyl, phenylalkyl, phenylalkenyl and phenylalkynyl having 1-6 carbon atoms in the chain;
- and wherein the substituent relative to the above-listed groups is selected from the group consisting of amino, hydroxyl, mercapto, alkylthio having from 1 to 6 carbon atoms, sulfamoyl, amidino, guanidino, nitro, chloro, bromo, fluoro, cyano, and carboxyl;
- with the proviso that when one of R.sup.1 or R.sup.2 is hydrogen and the other is 1-hydroxyethyl, then R.sup.3 is not hydrogen.
A compound having the structural formula:
- ##STR592## and the pharmaceutically acceptable salts thereof wherein R.sup.2 is selected from the group consisting of:
- ##STR593## and R.sup.3 is selected from the group consisting of:
- ##STR594##
The compound which is benzyl 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.
Dependencies are inferred from the claim text.