|Abstract:||An antibacterial 7beta-(carboxyalkenoyl)amino-3-cephem-4-carboxylic acid represented by the following formula: ##STR1## (wherein R is aryl or a heterocyclic group; R.sup.1 is hydrogen or halogen; R.sup.2 is a single bond, alkylene, or thiaalkylene; R.sup.3 is a hydrogen atom or carboxy modifying group; R.sup.4 is hydrogen or methoxy; R.sup.5 is hydrogen or a 3-substituent of cephalosporins; R.sup.6 is a hydrogen atom or carboxy modifying group; and X is oxygen, sulfur, or sulfinyl) a pharmaceutical composition containing the same, and a method for treating a bacterial infection with the same.|
|Inventor(s):||Hamashima; Yoshio (Kyoto, JP)|
|Assignee:||Shionogi & Co., Ltd. (Osaka, JP)|
|Filing Date:||Feb 20, 1986|
|Claims:||1. A 7beta-(carboxyalkenoylamino)-3-cephem-4-carboxylic acid compound represented by the following formula ##STR104## wherein R is 2-aminothiazol-4-yl or 5-amino-1,2,4-thiadiazol-3-yl; R.sup.1 is hydrogen; |
R.sup.2 is alkylene of 1 to 3 carbon atoms;
R.sup.3 is a hydrogen atom or a salt forming atom or group;
R.sup.4 is hydrogen or methoxy;
R.sup.5 is hydrogen, vinyl, cyanovinyl, carboxyvinyl, trifluoropropenyl, pyridiniomethyl, methoxymethyl, acetoxymethyl, carbamoyloxymethyl, methylthiomethyl, cyanomethylthiomethyl, difluoromethylthiomethyl, triazolylthiomethyl, thiadiazolylthiomethyl, methylthiadiazolylthiomethyl, aminomethylthiadiazolylthiomethyl, methyltetrazolylthiomethyl, methyl, methoxy, chloro, fluoroethylthio, trifluoroethylthio, vinylthio, or methanesulfonyloxy;
R.sup.6 is a hydrogen atom, salt forming atom or group, or ester forming group having 1 to 15 carbon atoms;
X is sulfur or sulfinyl with the proviso that when R.sup.2 is methylene and R.sup.5 is hydrogen, methyl, vinyl, cyanovinyl, trifluoropropenyl, methoxymethyl, carbamoyloxymethyl, methylthiomethyl, cyanomethylthiomethyl, thiadiazolylthiomethyl, triazolylthiomethyl, aminomethylthiadiazolylthiomethyl, methoxy, fluoroethylthio, trifluoroethylthio, or chloro, R is not protected or unprotected 2-aminothiazol-4-yl.
2. A compound claimed in claim 1 wherein the 7-acylamido double bond has the amido and carboxylic substituents in cis position.
3. A compound as claimed in claim 1 wherein R.sup.4 is hydrogen.
4. A compound as claimed in claim 1 wherein R.sup.6 is hydrogen, alkali metal, or a pharmaceutically acceptable ester group.
5. A compound as claimed in claim 1 wherein R.sup.6 is an alkyl or aralkyl ester-forming group.
6. A compound as claimed in claim 1 wherein X is sulfur.
7. A compound according to claim 1, said compound being selected from the group consisting of
7beta-[2-(2-aminothiazol-4-yl)-4-carboxy-2-butenoylamino]-3-acetoxymethyl-3 -cephem-4-carboxylic acid,
7beta-[2-(2-aminothiazol-4-yl)-4-carboxy-2-butenoylamino]-3-methyltetrazoly lthiomethyl-3-cephem-4-carboxylic acid,
7beta-[2-(2-aminothiazol-4-yl)-5-carboxy-2-pentenoylamino]-3-cephem-4-carbo xylic acid,
7beta-[2-(2-aminothiazol-4-yl)-6-carboxy-2-hexenoylamino]-3-cephem-4-carbox ylic acid,
7beta-[2-(2-aminothiazol-4-yl)-4-carboxy-2-pentenoylamino]-3-cephem-4-carbo xylic acid,
7beta-[2-(2-aminothiazol-4-yl)-4-carboxy-4-methyl-2-pentenoylamino]-3-cephe m-4-carboxylic acid,
or a salt or ester thereof.
8. An antibacterial composition comprising an effective amount of the compound as claimed in claim 4 and a pharmaceutically acceptable carrier.
9. A method for combating bacteria which comprises bringing an effective amount of the compound as claimed in claim 4 to contact with the bacteria.
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