2-oxo-oxazolidin-3,5-diyl antibiotic derivatives

1. A compound of formula I

wherein

R 1a represents H or carboxy and R 1b represents H, or R 1a and R 1b represent together either the group *—C(O)—NH—S— # or the group *—C(OH)═N—S— # wherein “*” represents the point of attachment of R 1a and “ # ” represents the point of attachment of R 1b ;

R 2 represents H, (C 1 -C 3 )alkyl, hydroxy-(C 1 -C 3 )alkyl, benzyl or (C 3 -C 5 )cycloalkyl;

R 3 represents H or halogen;

U represents N or CR 4 ; wherein R 4 is H or (C 1 -C 3 )alkoxy;

A represents CH, B represents NH, m represents 1 or 2 and n represents 1 or 2; or A represents N, B is absent, m represents 2 and n represents 2;

Y represents CH or N; and

Q represents O or S;

or a salt of such a compound.

2. The compound according to claim 1 , wherein:

R 1a represents H or carboxy;

R 1b represents H; and

A represents CH, B represents NH and m represents 1 and n represents 1 or m represents 2 and n represents 2; or A represents N, B is absent, m represents 2 and n represents 2;

or a salt of such a compound.

3. The compound according to claim 1 , wherein R 1 represents carboxy;

or a salt of such a compound.

4. The compound according to claim 1 , wherein R 2 represents (C 1 -C 3 )alkyl or (C 3 -C 5 )cycloalkyl;

or a salt of such a compound.

5. The compound according to claim 4 , wherein R 2 represents cyclopropyl;

or a salt of such a compound.

6. The compound according to one claim 1 , wherein R 3 represents halogen;

or a salt of such a compound.

7. The compound according to claim 1 , wherein U represents N;

or a salt of such a compound.

8. The compound according to claim 1 , wherein U represents CR 4 , wherein R 4 is H or (C1-C3)alkoxy;

or a salt of such a compound.

9. The compound according to claim 1 , wherein the group

is selected from

wherein the asterisks denote the bond linking said group to the CH 2 group which is attached to the oxazolidinone moiety;

or a salt of such a compound.

10. The compound according to claim 1 , wherein Y represents CH or N and Q represents O, or Y represents CH and Q represents S;

or a salt of such a compound.

11. The compound according to claim 1 , wherein:

R 1a represents carboxy and R 1b represents H, or R 1a and R 1b represent together either the group *—C(O)—NH—S— # or the group *—C(OH)═N—S— # wherein “*” represents the point of attachment of R 1a and “ # ” represents the point of attachment of R 1b ;

R 2 represents cyclopropyl;

R 3 represents fluorine;

U represents N;

A represents CH, B represents NH, m represents 1 or 2 and n represents 1 or 2;

Y represents N; and

Q represents O;

or a salt of such a compound.

12. The compound according to claim 1 , wherein the compound is:

1-cyclopropyl-6-fluoro-4-oxo-7-{4-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-ylmethyl]-piperazin-1-yl}1-1,4-dihydro-quinoline-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-{4-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)-oxazolidin-5-ylmethyl]-piperazin-1-yl}-1,4-dihydro-quinoline-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-{4-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-ylmethyl]-piperazin-1-yl}-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

6-((R)-5-{[1-(8-cyclopropyl-3-fluoro-5-oxo-5,8-dihydro-[1,8]naphthyridin-2-yl)-azetidin-3-ylamino]-methyl}-2-oxo-oxazolidin-3-yl)-4H-benzo[1,4]thiazin-3-one;

1-cyclopropyl-6-fluoro-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-8-methoxy-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid;

1-cyclopropyl-8-methoxy-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid;

1-ethyl-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-methyl-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

6-fluoro-1-methyl-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-benzyl-6-fluoro-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

6-fluoro-1-(2-hydroxy-ethyl)-4-oxo-7-(3-{[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-{4-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-ylmethyl]-piperazin-1-yl }-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-(4-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-piperidin-1-yl)-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-{4-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-piperazin-1-yl}-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-{4-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-piperazin-1-yl}-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-(4-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]amino}-piperidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-(3-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-pyrrolidin-1-yl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

1-cyclopropyl-6-fluoro-4-oxo-7-[(S)-3-({[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-methyl)-pyrrolidin-1-yl]-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;

9-cyclopropyl-6-fluoro-3-hydroxy-7-(4-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-piperidin-1-yl)-9H-1-thia-2,8,9-triaza-cyclopenta[b]naphthalen-4-one;

9-cyclopropyl-6-fluoro-3-hydroxy-7-(3-{[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-amino}-azetidin-1-yl)-9H-1-thia-2,8,9-triaza-cyclopenta[b]naphthalen-4-one; or

9-cyclopropyl-6-fluoro-3-hydroxy-7-{4-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-ylmethyl]-piperazin-1-yl}-9H-1-thia-2,8,9-triaza-cyclopenta[b]naphthalen-4-one;

or a salt of such a compound.

13. A medicament comprising the compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

14. A pharmaceutical composition comprising, as active principle, the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, and at least one therapeutically inert excipient.

15. A method of treating a bacterial infection comprising administering an effective amount of a compound or a salt thereof according to claim 1 to a subject in need thereof.

16. A method of treating a bacterial infection comprising administering an effective amount of the pharmaceutical composition according to claim 14 to a subject in need thereof.