5-amino-2-(1-hydroxy-ethyl)-tetrahydropyran derivatives

1. A compound of formula I

wherein

R 1 represents alkoxy;

R 2 represents H or F;

each of R 3 , R 4 , R 5 , and R 6 represents independently H or D;

V represents CH and W represents CH or N, or V represents N and W represents CH;

Y represents CH or N;

Z represents O, S, or CH 2 ; and

A represents CH 2 , CH 2 CH 2 , or CD 2 CD 2 ;

or a salt thereof.

2. The compound according to claim 1 , wherein each of R 3 , R 4 , R 5 , and R 6 represents H, and A represents CH 2 or CH 2 CH 2 ; or a salt thereof.

3. The compound according to claim 1 , wherein:

R 1 represents (C 1 -C 3 )alkoxy; and

at most one of R 3 , R 4 , R 5 , and R 6 represents D and A represents CH 2 or CH 2 CH 2 , or each of R 3 , R 4 , R 5 , and R 6 represents H and A represents CH 2 , CH 2 CH 2 , or CD 2 CD 2 ;

or a salt thereof.

4. The compound according to claim 1 , which is a compound of formula I p

wherein

R 1 represents alkoxy;

R 2 represents H or F;

W represents CH or N;

Y represents CH or N;

Z represents O, S, or CH 2 ; and

n represents 0 or 1;

or a salt thereof.

5. The compound according to claim 1 , wherein R 1 is methoxy; or a salt thereof.

6. The compound according to claim 1 , wherein R 2 represents H; or a salt thereof.

7. The compound according to claim 1 , wherein R 2 represents F; or a salt thereof.

8. The compound according to claim 1 , wherein W represents N; or a salt thereof.

9. The compound according to claim 1 , wherein W represents CH; or a salt thereof.

10. The compound according to claim 1 , wherein Y represents CH; or a salt thereof.

11. The compound according to claim 1 , wherein Y represents N; or a salt thereof.

12. The compound according to claim 1 , which is:

(1S)-1-{(2S,5R)-5-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethanol;

(1S)-1-{(2S,5R)-5-[(6,7-dihydro-[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethanol;

(1S)-1-{(2S,5R)-5-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-ethanol;

(1S)-1-{(2S,5R)-5-[(6,7-dihydro-[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-ethanol;

(1S)-1-{(2S,5R)-5-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(7-fluoro-2-methoxy-quinolin-8-yl)ethanol;

(1S)-1-{(2S,5R)-5-[(2,3-dihydro-4-oxa1- thia-6-aza-naphthalen-7-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-ethanol;

(1S)-1-{(2S,5R)-5-[(2,3-dihydro-4-oxa-1-thia-6-aza-naphthalen-7-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(7-fluoro-2-methoxy-quinolin-8-yl)-ethanol;

(1S)-2-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-1-{(2S,5R)-5-[(3-oxa-1-thia-5-aza-indan-6-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-ethanol;

(1S)-2-(7-fluoro-2-methoxy-quinolin-8-yl)-1-{(2S,5R)-5-[(3-oxa-1-thia-5-aza-indan-6-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-ethanol;

(1S)-1-{(2S,5R)-5-[(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-ethanol;

(1S)-1-{(2S,5R)-5-[(6,7-dihydro-8-oxa-5-thia-1,2-diaza-naphthalen-3-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-ethanol;

(1S)-1-{(2S,5R)-5-[(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(6-fluoro-3-methoxy-quinoxalin-5-yl)-ethanol;

(1S)-1-{(2S,5R)-5-[(6,7-dihydro-[1,4]dioxino[2,3-c]pyridazin-3-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(6-fluoro-3-methoxy-quinoxalin-5-yl-ethanol;

(1S)-1-{(2S,5R)-5-[(2,3-dihydro-4-oxa-1-thia-6-aza-naphthalen-7-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(6-fluoro-3-methoxy-quinoxalin-5-yl)-ethanol;

(1S)-1-{(2S,5R)-5-[(6,7-dihydro-8-oxa-5-thia-1,2-diaza-naphthalen-3-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(6-fluoro-3-methoxy-quinoxalin-5-yl)-ethanol;

(1S)-1-((2S,5R)-5-(((2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methyl-d1)amino)tetrahydro-2H-pyran-2-yl)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethanol;

(1S)-1-((2S,5R)-5-(((2,3-dihydro[1,4]dioxino-2,2,3,3-d4-[2,3-c]pyridin-7-yl)methyl)amino)tetrahydro-2H-pyran-2-yl)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethanol;

(1S)-1-(2S,5R)-5(((2,3-dihydro-[1,4]dioxino[2,3-c] pyridin-7-yl)methyl)amino)tetrahydro-2H-pyran-2-yl)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethanol-1-d1;

(S)-1-((2S,5R)-5-(((2,3-dihydro-[1,4]oxathiino[2,3-c]pyridin-7-yl)methyl-d1)amino)tetrahydro-2H-pyran-2-yl)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethanol;

(1S)-1-((2S,5R)-5-(((2,3-dihydro-[1,4]dioxino-[2,3-c]pyridin-7-yl)methyl)amino)tetrahydro-2H-pyran-2-yl)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethanol-2-d1;

(S)-1-((2S,5R)-5-(((2,3-dihydro-[1,4]oxathiino[2,3-c]pyridin-7-yl)methyl)amino)tetrahydro-2H-pyran-2-yl)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethanol-2-d1;

(S)-1-((2S,5R)-5-4(2,3-dihydro-[1,4]oxathiino[2,3-c]pyridin-7-yl)methyl)amino)tetrahydro-2H-pyran-2-yl)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethanol-1-d1;

(S)-1-{(2S,5R)-5-[(6,7-dihydro-8-oxa-5-thia-1,2-diaza-naphthalen-3-ylmethyl-d1)-amino]-tetrahydro-pyran-2-yl}-2-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-ethanol; or

(1S)-1-((2S,5R)-5-(((2,3-dihydro-[1,4]dioxino [2,3-c]pyridin-7-yl)methyl-d2)amino)tetrahydro-2H-pyran-2-yl)-2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)ethanol;

or a salt thereof.

13. A pharmaceutical composition comprising, as an active principle, the compound 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 caused by Staphylococcus aureus comprising administering to a subject in need thereof, the compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

15. A compound according to claim 1 , which is (1S)-1-{(2S,5R)-5-[(6,7-dihydro-8-oxa-5-thia-1,2-diaza-naphthalen-3-ylmethyl)-amino]-tetrahydro-pyran-2-yl}-2-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-ethanol; or a salt thereof.

16. A pharmaceutical composition comprising, as an active principle, the compound according to claim 15 , or a pharmaceutically acceptable salt thereof, and at least one therapeutically inert excipient.

17. A method for treating a bacterial infection caused by Staphylococcus aureus comprising administering to a subject in need thereof, the compound according to claim 15 , or a pharmaceutically acceptable salt thereof.