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US 4,361,512 AGranted
2-Substituted thio-6-substituted-carbapen-2-em-3-carboxylic acids
AssigneeMerck & Co., Inc.
InventorRonald W. Ratcliffe
Life of this patent
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Abstract
Disclosed are 2-substituted thio-6-substituted-carbapen-2-em-3-carboxylic acids (I) and their pharmaceutically acceptable salt, ester and amide derivatives which are useful as antibiotics: ##STR1## wherein: R.sup.5 is CN, ##STR2## (R is alkyl or aryl); R.sup.6 is hydrogen, R.sup.5, alkyl, aryl or heteroaryl; and R.sup.7 and R.sup.8 are, inter alia, hydrogen, alkyl, alkenyl, aryl and aralkyl.
Claims3
The process for preparing the compound of the formula:
- ##STR26## which comprises reacting the compound of the formula:
- ##STR27## with a diazo reagent:
- N.sub.2 .dbd.CR.sup.5 R.sup.6 III
- wherein the reaction takes place by dissolving compound II in a solvent such as tetrahydrofuran, dimethoxyethane, or toluene;
- in the presence of a catalytic amount of a copper catalyst which is copper II 2,4-pentanedione;
- then adding an excess of the diazo reagent III;
- at a temperature of about 55.degree.-57.degree. C. for about 1.5 hours;
- then quenching and isolating the resultant product Compound I;
- wherein R.sup.4 is p-nitrobenzyl, p-methoxybenzyl, o-nitrobenzyl, 2-trimethylsilyl or trimethylsilyl, or benzyl;
- R.sup.6 is hydrogen, CO.sub.2 CH.sub.2 CH.sub.3, CH.sub.3, CHO, CN;
- ##STR28## R.sup.5 is CO.sub.2 CH.sub.2 ##STR29## R.sup.8 is hydrogen, CH.sub.3 or OCH.sub.3 ;
- and R.sup.7 is ##STR30##
9 more elements
Dependencies are inferred from the claim text.