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Claims for Patent: 5,478,820

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Claims for Patent: 5,478,820

Title: Antibiotic compounds
Abstract:The present invention relates to carbapenems and provides a compound of the formula (I): ##STR1## or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof wherein: R.sup.1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R.sup.2 is hydrogen or C.sub.1-4 alkyl; R.sup.3 is hydrogen or C.sub.1-4 alkyl; R.sup.4 and R.sup.5 are the same or different and are selected from hydrogen, halo, cyano, C.sub.1-4 alkyl, nitro, hydroxy, carboxy, C.sub.1-4 alkoxy, C.sub.1-4 alkoxycarbonyl, aminosulphonyl, C.sub.1-4 alkylaminosulphonyl, di-C.sub.1-4 alkylaminosulphonyl, carbamoyl, C.sub.1-4 alkylcarbamoyl, di-C.sub.1-4 alkylcarbamoyl, trifluoromethyl, sulphonic acid, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, C.sub.1-4 alkanoylamino, C.sub.1-4 alkanoyl(N-C.sub.1-4 alkyl)amino, C.sub.1-4 alkanesulphonamido and C.sub.1-4 alkylS(O).sub.n -- wherein n is zero, one or two: with the proviso that there is no hydroxy or carboxy substituent in a position ortho to the --NR.sup.2 --. Processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.
Inventor(s): Betts; Michael J. (Wilmslow, GB2), Davies; Gareth M. (Macclesfield, GB2), Swain; Michael L. (Stockport, GB2)
Assignee: Zeneca Ltd. (London, GB2)
Application Number:08/129,056
Patent Claims: 1. ( 1R,5S,6S,8R,2'S,4'S)-2-(2-(3-Carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6 -(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid or a pharmaceutically acceptable salt or in vivo hydroysable ester thereof.

2. (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-Carboxyphenylcarbamoyl)pyrrolidin-4-yl thio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid.

3. (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-Carboxyphenylcarbamoyl)pyrrol idin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid in the form of a monosodium salt.

4. (1R,5S,6S,8R,2'S,4'S)-2-(2-( 3-Carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylca rbapenem-3-carboxylic acid in the form of a disodium salt.

5. A mixture of (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-Carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)- 6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid in the form of a monosodium salt and (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-Carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)- 6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid in the form of a disodium salt.

6. A method of treatment of a bacterial infection by administering an antibacterially effective amount of a compound according to claim 1.

7. A method of treatment of a bacterial infection by administering an antibacterially effective amount of a compound according to claim 2.

8. A method of treatment of a bacterial infection by administering an antibacterially effective amount of a compound according to claim 3.

9. A method of treatment of a bacterial infection by administering an antibacterially effective amount of a compound according to claim 4.

10. A method of treatment of a bacterial infection by administering an antibacterially effective amount of a compound according to claim 5.

11. An antibacterial pharmaceutical composition which comprises an antibacterially effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier.

12. An antibacterial pharmaceutical composition which comprises an antibacterially effective amount of a compound according to claim 2 and a pharmaceutically acceptable carrier.

13. An antibacterial pharmaceutical composition which comprises an antibacterially effective amount of a compound according to claim 3 and a pharmaceutically acceptable carrier.

14. An antibacterial pharmaceutical composition which comprises an antibacterially effective amount of a compound according to claim 4 and a pharmaceutically acceptable carrier.

15. An antibacterial pharmaceutical composition which comprises an antibacterially effective amount of a compound according to claim 5 and a pharmaceutically acceptable carrier.

16. A compound of the formula: ##STR17## wherein: --COOR.sup.6 and --COOR.sup.7 are carboxy or protected carboxy;

R.sup.8 is hydrogen, C.sub.1-4 alkyl, or an amino protecting group;

R.sup.9 is hydrogen or an amino protecting group;

and the hydroxy group in the 1-hydroxyethyl group is unprotected or protected.

17. A compound of the formula: ##STR18## wherein --COOR.sup.6 and --COOR.sup.7 are carboxy or protected carboxy;

R.sup.8 is hydrogen, C.sub.1-4 alkyl, or an amino protecting group;

R.sup.9 is hydrogen or an amino protecting group;

R.sup.11, R.sup.12 and R.sup.13 are independently selected from C.sub.1-6 alkoxy, aryloxy, di-C.sub.1-6 alkylamino and diarylamino or any two of R.sup.11, R.sup.12 and R.sup.13 represent o-phenylenedioxy; or one of R.sup.11, R.sup.12 and R.sup.13 is C.sub.1-4 alkyl, allyl, benzyl or phenyl and the other two values are independently selected from C.sub.1-4 alkyl, trifluoromethyl or phenyl, wherein any phenyl group is optionally substituted with C.sub.1-3 alkyl or C.sub.1-3 alkoxy;

and the hydroxy group in the 1-hydroxyethyl group is unprotected or protected.

18. A compound of the formula: ##STR19## wherein --COOR.sup.6 and --COOR.sup.7 are carboxy or protected carboxy;

R.sup.8 is hydrogen, C.sub.1-4 alkyl, or an amino protecting group;

R.sup.9 is hydrogen or an amino protecting group;

R.sup.14 is a protecting group; and

the hydroxy group in the 1-hydroxyethyl group is unprotected or protected.
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