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Claims for Patent: 5,652,233

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Claims for Patent: 5,652,233

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)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 (Cheshire, GB2), Davies; Gareth Morse (Cheshire, GB2), Swain; Michael Lingard (Cheshire, GB2)
Assignee: Zeneca Limited (London, GB)
Application Number:08/462,037
Patent Claims: 1. 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. A compound according to claim 1 wherein R.sup.1 is 1-hydroxyethyl.

3. A compound according to either claim 1 or claim 2 wherein R.sup.2 is hydrogen or methyl.

4. A compound according to either claim 1 or claim 2 wherein R.sup.2 is methyl.

5. A compound according to claim 1 or claim 2 wherein R.sup.3 is hydrogen.

6. A compound according to claim 1 of the formula (IV): ##STR18## wherein R.sup.3, R.sup.4 and R.sup.5 are as defined in claim 1.

7. A compound 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. A compound according to either claim 6 or claim 7 wherein at least one of R.sup.4 and R.sup.5 is hydrogen.

9. A compound 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.

10. A compound according to claim 1 which is

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-hydroxyphenylcarbamoyl)pyrrolidin-4 -ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4-chlorophenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-chlorophenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6 -(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-methanesulphonylphenylcarbamoyl)pyr rolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4-fluorophenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-fluorophenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-2,4-difluorophenylcarbamoyl)pyrrolidi n-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3,4-dicarboxyphenylcarbamoyl)pyrrolidin-4-ylthi o)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4-hydroxyphenylcarbamoyl)pyrrolidin-4 -ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3,5-dicarboxyphenylcarbamoyl)pyrrolidin-4-ylthi o)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(2-carbamoyl-3-carboxyphenylcarbamoyl) pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4-carbamoylphenylcarbamoyl)pyrrolidin -4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-carbamoylphenylcarbamoyl)pyrrolidin -4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-acetamidophenylcarbamoyl)pyrrolidin -4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4-acetamidophenylcarbamoyl) pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-methylsulphonamidophenylcarbamoyl)p yrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-sulphophenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-carbamoylphenylcarbamoyl)pyrrolidin -4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-2-dimethylaminocarbonylphenylcarbamoy l)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(5R,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1 -hydroxyethyl)carbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4-methylphenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-methylphenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-methylphenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-2-methoxyphenyharbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methyharbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4-methoxyphenylcarbamoyl)pyrrolidin-4 -ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-methoxyphenylcarbamoyl)pyrrolidin-4 -ylthio)-6-(1-hydroxyethyl)-1-methyharbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-methoxyphenylcarbamoyl)pyrrolidin-4 -ylthio)-6-(1-hydroxyethyl)-1-methyharbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4,6-dimethoxyphenylcarbamoyl)-4-ylthi o)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-methoxycarbonylphenylcarbamoyl)pyrr olidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-cyanophenylcarbamoyl)pyrrolidin-4-y lthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-trifluoromethylphenylcarbamoyl)pyrr olidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4,6-difluorophenylcarbamoyl)pyrrolidi n-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-methylsulphinylphenylcarbamoyl)pyrr olidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-methylsulphonylcarbamoyl)pyrrolidin -4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-fluorophenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-cyanophenylcarbamoyl)pyrrolidin-4-y lthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid, or

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-N'-methylphenylcarbamoyl)pyrrolidin-4 -ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

or a pharmaceutically acceptable salt thereof.

11. A compound according to claim 1 which is

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-methylphenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-methoxyphenylcarbamoyl)pyrrolidin-4 -ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-methoxyphenylcarbamoyl)pyrrolidin-4 -ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-methoxycarbonylphenyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-cyanophenylcarbamoyl)pyrrolidin-4-y lthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-6-chlorophenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6 -(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-4-fluorophenylcarbamoyl)pyrrolidin-4- ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-1-(1-(3-carboxy-6-fluorophenylcarbamoyl)pyrrolidin-4- ylthio)-6-(2-hydroxyethyl)-2-methylcarbapenem-3-carboxylic acid,

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3,4-dicarboxyphenylcarbamoyl)pyrrolidin-4-ylthi o)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid.

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3,5-dicarboxyphenylcarbamoyl)pyrrolidin-4-ylthi o)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid, or

(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxy-5-sulphophenylcarbamoyl)pyrrolidin-4- ylthio )-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid,

or a pharmaceutically acceptable salt thereof.

12. An antibacterial pharmaceutical composition which comprises an antibacterially effective amount of a compound according to any one of claims 1, 2, 6, 7, 9, 10 and 11, and a pharmaceutically acceptable carrier.

13. A method of treatment of a bacterial infection by administering an antibacterially effective amount of a compound of the formula (I) according to claim 1, to a patient in need thereof.

14. A compound of the formula (V): ##STR19## wherein: R.sup.2 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, C1-4alkylaminosulphonyl, 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, R.sup.4 and R.sup.5 optionally being protected; with the proviso that there is no hydroxy or carboxy substituent in a position ortho to the link to --NR.sup.8 --;

--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

R.sup.10 is 1-hydroxyethyl, 1-fluoroethyl, hydroxymethyl, protected 1-hydroxyethyl or protected hydroxymethyl;

and wherein at least one protecting group is present.

15. A compound of the formula (VII): ##STR20## where 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, R.sup.4 and R.sup.5 optionally being protected; with the proviso that there is no hydroxy or carboxy substituent in a position ortho to the link to --NR.sup.8 --;

--COOR.sup.6 is carboxy or protected carboxy;

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

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

16. A compound of the formula (VIII): ##STR21## wherein: R.sup.2 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, R.sup.4 and R.sup.5 optionally being protected; with the proviso that there is no hydroxy or carboxy substituent in a position ortho to the link to --NR.sup.8 --;

--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

R.sup.10 is 1-hydroxyethyl, 1-fluoroethyl, hydroxymethyl, protected 1-hydroxyethyl or protected hydroxymethyl,

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 wherein any functional group is optionally protected.

17. A non-pharmaceutically acceptable salt of a compound of the formula (I): ##STR22## 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 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 --.

18. A compound of the formula (IX), (XII) or (XIV): ##STR23## wherein: R.sup.2 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, C1-4alkanoyl(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, R.sup.4 and R.sup.5 optionally being protected; with the proviso that there is no hydroxy or carboxy substituent in a position ortho to the link to --NR.sup.8 --;

--COOR.sup.6 and --COOR.sup.7 are carboxy or protected carboxy;

R.sup.8 is hydrogen, C1-4alkyl, or an amino protecting group;

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

R.sup.10 is 1-hydroxyethyl, 1-fluoroethyl, hydroxymethyl, protected 1-hydroxyethyl or protected hydroxymethyl; and

R.sup.14 is a protecting group.
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