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US 4,225,706 AGranted
Polychalcogen ester of cephem compound, process for preparing the same and method for removing the protective group of the same
AssigneeMeiji Seika Kaisha, Ltd.
InventorsShigeo Seki, Ken Nishihata, Satoru Nakabayashi, Toshinori Saito, Hitoshi Ikeda, Nobuo Itoh, Shokichi Nakajima, Shunzo Fukatsu
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Abstract
A novel ester of a cephem compound having a carboxyl group at the 4-position in the nucleus; a process for preparing the same by reacting a cephem carboxylic acid or its salt with a halogenide; and a method for removing the protective group for the carboxyl group in the nucleus of a cephem compound by contacting it with an alcohol, or with an organic solvent in the presence of a Lewis acid.
Claims7
An ester of a cephem compound represented by the formula:
- ##STR13## wherein A is selected from the group consisting of .beta.-methoxyethoxy-methyl, .beta.-methoxyethoxyethyl, .beta.-ethoxyethoxymethyl, .beta.-ethoxyethoxy-ethyl, .beta.-propyloxyethoxymethyl, .beta.-isopropyloxyethoxymethyl, .beta.-t-butoxyethoxymethyl, .beta.-phenoxyethoxymethyl, .beta.-benzyloxyethoxymethyl, .beta.-methoxy-.beta.-methylethoxymethyl, .gamma.-methoxypropyloxymethyl, .beta.-methylthioethylthiomethyl and .beta.-methoxyethylthiomethyl;
- B is selected from the group consisting of cyano, cyanomethylthio, trifluoromethylthio, phenyl, tolyl, chlorophenyl, bromophenyl, methoxyphenyl, hydroxyphenyl, phenoxy, tolyloxy, chlorophenoxy, bromophenoxy, methoxyphenoxy, hydroxyphenoxy, benzyl, methyl-benzyl, chlorobenzyl, .alpha.-phenethyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 1H-tetrazolyl, 4-pyridylthio, and ##STR14## wherein R.sup.4 is selected from the group consisting of methoxycarbonyl, ethoxycarbonyl, 5-butoxycarbonyl, benzoyl, p-chlorobenzoyl, phthaloyl, carbobenzoxy, chloroacetyl, 2,4-dinitrophenyl, phenylacetyl, and A is the same as defined above;
- R.sup.6 is selected from the group consisting of hydrogen, hydroxyl, benzoyl amino, p-chlorobenzoyl amino, phthalimido, t-butoxycarbonyl amino, carbobenzoxyamino;
- R.sup.7 is selected from the group consisting of a hydrogen atom, acetoxy, propionyloxy, pyridyl, carbamoylpyridyl, acetylaminopyridyl, methylthiopyridyl, methylthio, ethylthio, 1,3,4-thiadiazolylthio, 2-methyl-1,3,4-thiadiazolylthio, 1-methyl-tetrazolylthio, 1,2,3-triazolylthio, and 1,3,4-oxadiazolylthio;
- R.sup.8 is hydrogen or a methoxy group;
- and
- Z is 0 or 1.
4 more elements
Dependencies are inferred from the claim text.