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Claims for Patent: 7,342,005

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Claims for Patent: 7,342,005

Title:Antibiotic compounds
Abstract:The present invention relates to carbapenems and provides a compound of the formula (I): ##STR00001## 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.1-4alkyl; R.sup.3 is hydrogen or C.sub.1-4alkyl; R.sup.4 and R.sup.5 are the same or different and are selected from hydrogen, halo, cyano, C.sub.1-4alkyl, nitro, hydroxy, carboxy, C.sub.1-4alkoxy, C.sub.1-4alkoxycarbonyl, aminosulphonyl, C.sub.1-4alkylaminosulphonyl, di-C.sub.1-4-alkylaminosulphonyl, carbamoyl, C.sub.1-4alkylcarbamoyl, di-C.sub.1-4alkylcarbamoyl, trifluoromethyl, sulphonic acid, amino, C.sub.1-4alkylamino, di-C.sub.1-4alkylamino, C.sub.1-4alkanoylamino, C.sub.1-4alkanoyl(N--C.sub.1-4alkyl)amino, C.sub.1-4alkanesulphonamido and C.sub.1-4alkylS(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: AstraZeneca UK Limited (London, GB)
Application Number:11/126,331
Patent Claims: 1. A pharmaceutical formulation for intravenous, subcutaneous or intra-muscular injection comprising a compound of the formula (I) ##STR00017## or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof and a pharmaceutically acceptable injectable carrier, wherein: R.sup.1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R.sup.2 is hydrogen or C.sub.1-4alkyl; R.sup.3 is hydrogen or C.sub.1-4alkyl; R.sup.4 and R.sup.5 are the same or different and are selected from hydrogen, halo, cyano, C.sub.1-4alkyl, nitro, hydroxy, carboxy, C.sub.1-4alkoxy, C.sub.1-4alkoxycarbonyl, aminosulphonyl, C.sub.1-4alkylaminosulphonyl, di-C.sub.1-4-alkylaminosulphonyl, carbamoyl, C.sub.1-4alkylcarbamoyl, di-C.sub.1-4alkylcarbamoyl, trifluoromethyl, sulphonic acid, amino, C.sub.1-4alkylamino, di-C.sub.1-4alkylamino, C.sub.1-4alkanoylamino, C.sub.1-4alkanoyl(N--C.sub.1-4alkyl)amino, C.sub.1-4alkanesulphonamido and --S(O).sub.nC.sub.1-4alkyl and 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 according to claim 1, wherein R.sup.1 is 1-hydroxyethyl.

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

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

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

6. The pharmaceutical formulation according to claim 1, wherein the compound has the structure of formula (IV): ##STR00018##

7. The pharmaceutical formulation 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 and acetamido.

8. The pharmaceutical formulation 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 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 according to claim 6 wherein R.sup.4 is hydrogen, carboxy, fluoro, chloro, methyl, methoxy, cyano, sulphonic acid or methoxycarbonyl and R.sup.5 is hydrogen.

11. The pharmaceutical formulation 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-ylthio)- -6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof.

12. The pharmaceutical formulation 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-ylthio)- -6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid.

13. The pharmaceutical formulation 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-ylthio- )-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid in the form of a monosodium salt.

14. The pharmaceutical formulation 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-ylthio- )-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid in the form of a disodium salt.

15. A pharmaceutical formulation comprising 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.

16. The pharmaceutical formulation according to any one of claims 1 and 6, wherein said composition comprises from 100 mg to 1 g of the compound of the formula (I) or formula (IV).

17. The pharmaceutical formulation according to any one of claims 1 and 6, wherein the pharmaceutically acceptable injectable carrier comprises water or an aqueous solution of sodium chloride.

18. A process for preparing the pharmaceutical formulation of claim 1 for intravenous, subcutaneous or intramuscular injection, said process comprising reconstituting a dry powder filled vial, which powder comprises a compound of formula (I) or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof as defined in claim 1, in a pharmaceutically acceptable injectable carrier.

19. The process of claim 18 wherein said pharmaceutically acceptable injectable carrier comprises water or an aqueous solution of sodium chloride.
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