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Claims for Patent: 4,839,350

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Claims for Patent: 4,839,350

Title: Cephalosporin compounds and the production thereof
Abstract:A class of new caphalosporin compounds (syn-isomer) is now provided, which is useful as antibacterial agent and is represented by the general formula (I) ##STR1## wherein R.sup.1 is an amino group or a protected amino group; R.sup.2 is a lower alkyl group, a carboxymethyl group or a protected carboxymethyl group; R.sup.3 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group; A is an unsubstituted or substituted phenyl group, an unsubstituted or substituted furyl group, an unsubstituted or substituted thiazolyl group or an unsubstituted or substituted 3-lower-alkylthiazolio group, and a pharmaceutically acceptable salt or ester thereof.
Inventor(s): Atsumi; Kunio (Kawasaki, JP), Sakagami; Kenji (Kawasaki, JP), Yamamoto; Yuichi (Yokohama, JP), Yoshida; Takashi (Tokyo, JP), Nishihata; Ken (Yokohama, JP), Kondo; Shinichi (Yokohama, JP), Fukatsu; Shunzo (Tokyo, JP)
Assignee: Meiji Seika Kaisha, Ltd. (Tokyo, JP) Susumu Mitsuhashi (Tokyo, JP)
Application Number:07/036,124
Patent Claims: 1. A cephalosporin compound of the formula (I) ##STR23## wherein R.sup.1 is an amino group or a protected amino group; R.sup.2 is a lower alkyl group, a carboxymethyl group or a protected carboxymethyl group; R.sup.3 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group; A is thiazolyl group, a lower-alkyl-thiazolyl group, a halo-thiazolyl group, or a 3-lower-alkylthiazolio group optionally substituted with one lower alkyl group, with an iodide or tirfluoroacetate counterion, and a pharmaceutically acceptable salt or ester of said cephalosporin compound.

2. A cephalosporin compound as claimed in claim 1 which if of the formula (Ic) ##STR24## wherein R.sup.1 is an amino group or a protected amino group, R.sup.2 is a lower alkyl group, a carboxymethyl group or a protected carboxymethyl group, and R.sup.3 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group.

3. A cephalosporin compound as claimed in claim 1 which is of the formula (Id) ##STR25## wherein R.sup.1 is an amino group or a protected amino group, R.sup.2 is a lower (C.sub.1 -C.sub.6) alkyl group, a carboxymethyl group or a protected carboxymethyl group, R.sup.3 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group, R is a lower alkyl group and X is an iodide ion or a trifluoroacetate ion.

4. A cephalosporin compound as claimed in claim 1 which is of the formula (Ie) ##STR26## wherein R.sup.1 is an amino group or a protected amino group, R.sup.2 is a lower (C.sub.1 -C.sub.3) alkyl group, a carboxymethyl group, or a protected carboxymethyl group, R.sup.3 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group, and Y' is a hydrogen atom or a halogen atom, and n is a whole number of 1 or 2.

5. A cephalosporin compound as claimed in claim 1 which is of the formula (If) ##STR27## wherein R.sup.1 is an amino group or a protected amino group, R.sup.2 is a lower (C.sub.1 -C.sub.6) alkyl group, a caroboxymethyl group or a protected carboxymethyl group, and R.sup.3 is a hydrogen atom, a salt-forming cation or a carboxyl-protecting group.

6. A compound as claimed in claims 1, 2, 3, 4 or 5 in which R.sup.1 is an amino group, R.sup.2 is a methyl group or a carboxymethyl group, and R.sup.3 is sodium atom, benzhydryl group, p-methoxybenzyl group, diphenylmethyl group, pivaloyloxymethyl group or (5-methyl-2-oxo-1,3-dioxolene-4-yl)-methyl group.

7. A compound as claimed in claim 1 which is selected from the group consisting of

7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(thiazol-2-yl)viny l]-3-cephem-4-carboxylic acid (syn-isomer, trans-isomer, or syn-isomer, cis-isomer);

7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(thiazol-4-yl)viny l]-3-cephem-4-carboxylic acid (syn-isomer, cis-isomer) and its sodium salt and its pivaloyloxymethyl ester; and

7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(thiazol-5-yl)viny l]-3-cephem-4-carboxylic acid (syn-isomer, cis-isomer), it sodium salt, and its pivaloyloxymethyl ester.

8. A compound as claimed in claim 1 which is selected from the group of consisting of

7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(4-methylth iazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer, trans-isomer, or syn-isomer, cis-isomer) and its acid addition salt with trifluoroacetic acid,

7-[2-t-butoxycarbonylmethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3 -[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer, trans-isomer, or syn-isomer, cis-isomer); and

7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(2-methylthiazol-5 -yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer, trans-isomer, or syn-isomer, cis-isomer), its sodium salt, its acid addition salt with trifluoroacetic acid, and its (5-methyl-2-oxo-1,3-dioxolene-4-yl)-methyl ester.

9. A compound as claimed in claim 1 which is selected from the group consisting of

7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(4-chlorothiazol-5 -yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer, cis-isomer), its sodium salt and its pivaloyloxymethyl ester; and

7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(2,4-dichlorothiaz ol-5-yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer, cis-isomer), it sodium salt and its pivaloyloxymethyl ester.

10. A compound as claimed in claim 1 which is 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(3,4-dimethyl-5-t hiazolio)vinyl]-3-cephem-4-carboxylic acid (syn-isomer, trans-isomer, or syn-isomer, cis-isomer) iodide or its acid addition salt with trifluoroacetic acid.

11. 7-[2-methoxyimino- 2-(2-aminothiazol-4-yl)acetamido]-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephe m-4-carboxylic acid (syn-isomer, cis-isomer) sodium salt.

12. 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3 -[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer, cis-isomer) pivaloyloxymethyl ester.

13. A compound which is selected from the group consisting of 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido-3-[2-(4-methylthiazol-5 -yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer, trans-isomer, or syn-isomer, cis-isomer), a sodium salt thereof, a pivaloyloxymethyl ester thereof, a (5-methyl-2-oxo-1,3-dioxolene-4-yl)-methyl ester thereof and an acid addition salt thereof with trifluoroacetic acid.

14. A pharmaceutical, antibacterial composition which comprises an antibacterially effective amount of the compound of the formula (I) as defined in claim 1 or the compound of the formula (Ic) to (If) as defined in anyone of claims 2 to 5 or a pharmaceutically acceptable salt or ester thereof, as the active ingredient, in combination with a pharmaceutically acceptable carrier for the active ingredient.
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