[4-(1-amino-ethyl)-cyclohexyl]-methyl-amine and [6-(1-amino-ethyl)-tetrahydro-pyran-3-yl]-methyl-amine derivatives as antibacterials

1. A compound of formula I

wherein

R 1 represents alkoxy or halogen;

U, V, and W each represents CH, or one of U, V, and W represents N and the others each represents CH;

A represents CH 2 or O;

G is CH═CH-E wherein E represents a phenyl group mono- or di-substituted with halogen, or

G is

wherein Z represents CH or N, Q represents O or S, and K represents O or S;

or a salt thereof.

2. The compound of formula I according to claim 1 , wherein U represents CH, G is CH═CH-E wherein E represents a phenyl group mono- or di-substituted with halogen, or G is a

wherein Z represents CH or N and Q represents O or S;

or a salt thereof.

3. The compound of formula I according to claim 1 , wherein: U, V, and W each represents CH; U and W each represents CH and V represents N; U and V each represents CH and W represents N; or U represents N and V and W each represents CH; and

R 1 is methoxy or ethoxy;

or a salt thereof.

4. The compound of formula I according to claim 1 ,

wherein

R 1 represents alkoxy or fluorine;

U, V and W each represents CH; U represents CH, one of V and W represents N and the other represents CH; or U represents N and V and W each represent CH;

A represents CH 2 or O;

G is CH═CH-E wherein E represents a phenyl group di-substituted with halogen, or

G is

wherein Z represents CH or N and Q represents O or S;

or a salt thereof.

5. The compound of formula I according to claim 1 , wherein R 1 represents methoxy;

or a salt thereof.

6. The compound of formula I according to claim 1 , wherein A represents CH 2 ;

or a salt thereof.

7. The compound of formula I according to claim 1 , wherein A represents O;

or a salt thereof.

8. The compound of formula I according to claim 1 , wherein G is

wherein Z represent CH or N and Q represents O or S;

or a salt thereof.

9. The compound of formula I according to claim 1 , wherein G represents 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl; 3-oxo-3,4,4a,8a-tetrahydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl; 3-oxo-3,4,4a,8a-tetrahydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl; 2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl; or 2-(2,5-difluoro-phenyl)-vinyl;

or a salt thereof.

10. The compound of formula I according to claim 1 , which is:

6-(trans-{4-[(1R)-1-amino-2-(7-methoxy-2-oxo-2H-quinolin-1-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

6-(trans-{4-[(1R)-1-amino-2-(7-methoxy-2-oxo-2H-quinolin-1-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-quinolin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one;

1-((2S)-2-amino-2-{(2S,5R)-5-[(E)-3-(2,5-difluoro-phenyl)-allylamino]-tetrahydro-pyran-2-yl}-ethyl)-7-methoxy-1H-quinolin-2-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-quinolin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-[1,5]naphthyridin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-[1,5]naphthyridin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-[1,5]naphthyridin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-benzo[1,4]oxazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-quinoxalin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-[1,8]naphthyridin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-[1,8]naphthyridin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one;

1-((1S)-2-amino-2-{(2S,5R)-5-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-ethyl)-7-methoxy-1H-[1,8]naphthyridin-2-one; or

1-((1R)-2-amino-2-{4-[(E)-3-(2,5-difluoro-phenyl)-allylamino]-cyclohexyl}-ethyl)-7-methoxy-1H-quinolin-2-one;

or a salt thereof.

11. The compound of formula I according to claim 1 , which is:

6-(trans-{4-[(1R)-1-amino-2-(7-methoxy-2-oxo-2H-quinolin-1-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

6-(trans-{4-[(1R)-1-amino-2-(7-methoxy-2-oxo-2H-quinolin-1-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-quinolin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one;

1-((2S)-2-amino-2-{(2S,5R)-5-[(E)-3-(2,5-difluoro-phenyl)-allylamino]-tetrahydro-pyran-2-yl}-ethyl)-7-methoxy-1H-quinolin-2-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-quinolin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-[1,5]naphthyridin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-[1,5]naphthyridin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one;

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-[1,5]naphthyridin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-benzo[1,4]oxazin-3-one; or

6-({(3R,6S)-6-[(1S)-1-amino-2-(7-methoxy-2-oxo-2H-quinoxalin-1-yl)-ethyl]-tetrahydro-pyran-3-ylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

or a salt thereof.

12. A pharmaceutical composition, comprising the compound of formula I according to claim 1 , or a pharmaceutically acceptable salt thereof.

13. A pharmaceutical composition comprising, as an active ingredient, the compound of formula I according to claim 1 , or a pharmaceutically acceptable salt thereof, and at least one therapeutically inert excipient.

14. A method for treating a bacterial infection comprising administering the medicament of claim 12 .

15. A method for treating a bacterial infection comprising administering the pharmaceutical composition of claim 13 to a subject in need thereof.