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Details for Patent: 6,521,612

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Details for Patent: 6,521,612

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 link to --NR.sup.3 --. Processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.
Inventor(s): Betts; Michael John (Wilmslow, GB), Davies; Gareth Morse (Macclesfield, GB), Swain; Michael Lingard (Stockport, GB)
Assignee: Zeneca Ltd. (London, GB)
Filing Date:Feb 13, 2001
Application Number:09/781,556
Claims:1. A pharmaceutical formulation for oral administration comprising a compound of the formula (I) ##STR17##

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 --S(O).sub.n C.sub.1-4 alkyl wherein n is zero, one or two:

with the proviso that there is no hydroxy or carboxy substituent in a position ortho to the link to --NR.sup.3 --.

2. The pharmaceutical formulation for oral administration according to claim 1, wherein R.sup.1 is 1-hydroxyethyl.

3. The pharmaceutical formulation for oral administration to claim 1 or claim 2, wherein R.sup.2 is hydrogen or methyl.

4. The pharmaceutical formulation for oral administration according to claim 1 or claim 2 wherein R.sup.2 is methyl.

5. The pharmaceutical formulation for oral administration according to claim 1 or claim 2, wherein R.sup.3 is hydrogen.

6. The pharmaceutical formulation for oral administration according to claim 1, wherein the compound has the structure of formula (IV): ##STR18##

7. The pharmaceutical formulation for oral administration according to claim 6 wherein R.sup.4 and R.sup.5 are the same or different and selected from hydrogen, fluoro, chloro, hydroxy, carboxy, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methoxycarbonyl, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, trifluoromethyl, sulphonic acid, methylsulphinyl, methylsulphonyl, methanesulphonamido or acetamido.

8. The pharmaceutical formulation for oral administration according to claim 6 wherein at least one of R.sup.4 and R.sup.5 in the compound of formula (IV) is hydrogen.

9. The pharmaceutical formulation for oral administration according to claim 7 wherein at least one of R.sup.4 and R.sup.5 in the compound of formula (IV) is hydrogen.

10. The pharmaceutical formulation for oral administration according to claim 6 wherein R.sup.4 is hydrogen, carboxy, fluro, chloro, methyl, methoxy, cyano, sulphonic acid or methoxycarbonyl and R.sup.5 is hydrogen.

11. The pharmaceutical formulation for oral administration according to claim 1, wherein the compound of formula (I) is (1R,5S,6S,8R,2'S,4'S)-2- (2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-lythio)-6- (1-hydrxyethyl)-1-methylcarbapenem-3-carboxylic acid of a pharmaceutically acceptable salt or in vivo hydrplysable ester thereof.

12. The pharmaceutical formulation for oral administration according to claim 1, wherein the compound of formula (I) is (1R,5S,6S,8R,2'S,4'S)-2- (2-(3-carboxyphenylcarbamoyl0pyrrolidin-4-lythio)-6- (1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid.

13. The pharmaceutical formulation for oral administration according to claim 1, wherein the compound of formula (I) is (1R,5S,6S,8R,2'S,4'S)-2- (2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-lythio)-6- (1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid in the form of a monosodium salt.

14. The pharmaceutical formulation for oral administration according to claim 1, wherein the compound of formula (I) is (1R,5S,6S,8R,2'S,4'S)-2- (2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-lythio)-6- (1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid in the form of a disodium salt.

15. A pharmaceutical formulation for oral administration comprising a mixture of (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-lythio)- 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-lythio)- 6- (1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid in the form of a disodium salt.

16. The pharmaceutical formulation for oral administration according to claim 1 or claim 6, wherein said composition comprises from 100 mg to 1 g of the compound of the formula (I) or formula (IV).
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