3-(Substituted) vinyl cephalosporins
AssigneeEli Lilly and Company
InventorJohn Alan Webber
Life of this patent
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Abstract
New 3-(substituted) vinyl cephalosporin compounds, e.g., 3-(2'-ethoxycarbonylvinyl)-7-phenoxyacetamido-3-cephem-4-carboxylic acid, which are useful as antibiotics, and 3-(substituted) vinyl cephalosporin compounds which are useful as intermediates in preparing antibiotic substances.
Claims18
A compound of the formula ##STR32## wherein n is 0 or 1;
- R is hydrogen, cyanoacetyl or a group of the formula ##STR33## wherein Ar is 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, phenyl, or nitrophenyl;
- ##STR34## wherein X is oxygen or sulfur and Ar is as defined above;
- ##STR35## wherein Ar is as defined above and B is --OH, or such --OH group protected by esterification with a C.sub.1 -C.sub.6 alkanoic acid;
- or
- B is --COOH, or such --COOH group protected by esterification with a C.sub.1 -C.sub.6 alkanol;
- or B is ##STR36## --NH-SO.sub.3 H, or --C(O)-NH.sub.2 ;
- R.sup.1 is hydrogen, or
- R and R.sup.1 taken together with the nitrogen to which they are bonded denote --NH.sub.3.sup.+, a salt group with an acid having a pKa of less than 4, or a cyclic imide group from a C.sub.3 to C.sub.12 hydrocarbon dicarboxylic acid;
- R.sup.2 is hydrogen,
- C.sub.4 to C.sub.6 -tert-alkyl,
- C.sub.5 to C.sub.7 -tert-alkenyl,
- C.sub.5 to C.sub.7 -tert-alkynyl, or
- a pharmaceutically acceptable cation;
- and
- Y is --C(O)OR.sup.3 where R.sup.3 is C.sub.1 -C.sub.4 alkyl, --CN, --COOH, --CHO, --X-C.sub.1 to C.sub.4 alkyl wherein X is oxygen or sulfur, --C(O)-NH.sub.2, --NO.sub.2, --S(O)-C.sub.1 C.sub.4 alkyl, --S(O).sub.2 C.sub.1 -C.sub.4 alkyl, or Cl, Br, or trifluoromethyl.
The compound of the formula ##STR41## wherein B is hydroxy, formyloxy, carboxy, or t-butoxycarbonyl;
- Y is --CN, --COOH, or ##STR42## and R.sup.2 is hydrogen, t-butyl, or a pharmaceutically acceptable cation.
A compound of the formula ##STR44## wherein R.sup.2 is t-butyl and Y is t-butyloxycarbonyl, ethyloxycarbonyl, and cyano.
A compound of the formula ##STR45## wherein Y is cyano, carboxy, or ethoxycarbonyl.
Dependencies are inferred from the claim text.