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Claims for Patent: 4,918,068

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Claims for Patent: 4,918,068

Title: Cephem compounds
Abstract:There are provided new cephem compounds (synisomers) represented by the following general formula (I): ##STR1## wherein R.sup.1 means a lower group, R.sup.2 denotes an ester-forming group of the carboxyl group, and the 4-methylthiazolyl group and the cephem moiety are cis to each other relative to the carbon-carbon double bond of the substituted vinyl group in the side chain at the 3-position of the cephem nucleus. The cephem compounds exhibit strong antibacterial activities not only against resistant strains of bacteria and gram-negative bacteria but also against gram-positive bacteria and moreover have very low toxicity.
Inventor(s): Yamamoto; Yuichi (Yokohama, JP), Atsumi; Kunio (Kawasaki, JP), Sakagami; Kenji (Kawasaki, JP), Yoshida; Takashi (Tokyo, JP), Nishihata; Ken (Yokohama, JP), Kondo; Sinichi (Yokohama, JP)
Assignee: Meiji Seika Kaisha, Ltd. (Tokyo, JP)
Application Number:07/019,172
Patent Claims: 1. The syn-isomer of a cephem compound represented by the following formula (I) ##STR7## wherein R.sup.1 means a lower alkyl group, R.sup.2 denotes a lower alkanoyloxyalkyl group, a lower alkoxycarbonyloxyalkyl group, phthalidyl group or (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl group of the carboxyl group, and the 4-methylthiazolyl group and the cephem moiety are cis to each other relative to the carbon-carbon double bond of the substituted vinyl group in the side chain at the 3-position of the cephem nucleus.

2. The compound as claimed in claim 1, wherein R.sup.1 is a methyl or ethyl group, and R.sup.2 is a pivaloyloxymethyl, acetoxymethyl, 1-acetoxyethyl, 1-ethoxycarbonyloxyethyl, phthalidyl or (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl group.

3. The compound as claimed in claim 2, which is pivaloyloxymethyl 7-[2-ethoxyimino-2-(2-aminothiazol-4yl)acetamido-]-3-[2-(4-methylthiazol-5 -yl)vinyl]-3-cephem-4-carboxylate.

4. The compound as claimed in claim 2, which is acetoxymethyl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(4-methylthiazol- 5-yl)vinyl]-3-cephem-4-carboxylate.

5. The compound as claimed in claim 2, which is 1-acetoxyethyl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido-]-3-[2-(4-methylthiazol -5-yl)vinyl]-3-cephem-4-carboxylate.

6. The compound as claimed in claim 2, which is 1-ethoxycarbonyloxyethyl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(4-methylthiazol- 5-yl)vinyl]-3-cephem-4-carboxylate.

7. The compound as claimed in claim 2, which is phthalidyl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)-acetamido]-3-[2-(4-methylthiazol -5-yl)vinyl]-3-cephem-4-carboxylate.

8. The compound as claimed in claim 2, which is (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(4-methylthiazol- 5-yl)vinyl]-3-cephem-4-carboxylate.

9. A pharmaceutical, antibacterial composition which comprises an antibacterially effective amount compound of the formula (I) as defined in claim 1 as the active ingredient, in combination with a pharmaceutically acceptable carrier for the active ingredient.
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