Antibacterial 1

1. A compound of formula I

wherein

X represents N or CH;

R 1 represents H or halogen;

R 2 represents (C 3 -C 4 )alkynyloxy or the group M;

R 3 represents H or halogen;

M is one of the groups M A and M B represented below

wherein A represents a bond, CH 2 CH 2 , CH═CH or C≡C;

R 1A represents H or halogen;

R 2A represents H, (C 1 -C 3 )alkoxy or halogen;

R 3A represents H, (C 1 -C 3 )alkoxy, hydroxy(C 1 -C 4 )alkoxy, (C 1 -C 3 )alkoxy(C 2 -C 3 )alkoxy, (C 1 -C 3 )thioalkoxy, trifluoromethoxy, amino, hydroxy(C 1 -C 4 )alkyl, 2-hydroxyacetamido, 1-aminocyclopropyl, 1-hydroxymethyl-cycloprop-1-yl, 1-((phosphonooxy)methyl)cyclopropyl, 1-(((dimethylglycyl)oxy)methyl)cyclopropyl, trans-2-hydroxymethyl-cycloprop-1-yl, 1,2-dihydroxyethyl, 3-hydroxyoxetan-3-yl, 3-(hydroxy(C 1 -C 3 )alkyl)oxetan-3-yl, 3-aminooxetan-3-yl, 3-hydroxythietan-3-yl, morpholin-4-yl(C 2 -C 3 )alkoxy, morpholin-4-yl-(C 1 -C 2 )alkyl, oxazol-2-yl or [1,2,3]triazol-2-yl; and

R 1B represents hydroxy(C 1 -C 3 )alkyl, dihydroxy(C 1 -C 4 )alkyl, amino(C 1 -C 3 )alkyl, (dimethylamino)methyl, 1-hydroxymethyl-cycloprop-1-yl, trans-2-(1,2-dihydroxyethyl)cycloprop-1-yl, 1-methyl-2-hydroxymethyl-cycloprop-1-yl, 2-(hydroxymethyl)-2-methylcyclopropyl, 1-aminomethyl-cycloprop-1-yl, trans-2-hydroxymethyl-cycloprop-1-yl, 1-fluoro-2-(hydroxymethyl)cyclopropyl, 2-fluoro-2-(hydroxymethyl)cyclopropyl, 1-(hydroxymethyl)cyclobutyl, 3-hydroxyoxetan-3-yl, 3-hydroxymethyl-oxetan-3-yl, 3-hydroxythietan-3-yl, 1-(2-hydroxyacetyl)azetidin-3-yl, 1-(2-aminoacetyl)azetidin-3-yl, 1-glycylazetidin-3-yl, 1-(2-amino-2-methylpropanoyl)azetidin-3-yl, 3-(2-aminoacetamido)cyclopentyl, trans-(cis-3,4-dihydroxy)-cyclopent-1-yl, 3-hydroxymethylbicyclo[1,1,1]pentan-1-yl, 3-hydroxymethylbicyclo[1,1,1]pentan-1-yl, piperidin-4-yl, 1-(2-hydroxyacetyl)piperidin-4-yl, 4-hydroxytetrahydro-2H-pyran-4-yl, 5-aminotetrahydro-2H-pyran-2-yl, (1s,3r)-(1-hydroxy-3-(hydroxymethyl)cyclobutyl)methyl or 3-hydroxyoxetan-3-ylmethyl;

or a salt thereof.

2. The compound of formula I according to claim 1 , which is a compound of formula I P

wherein

X represents N or CH;

R 1 represents H or halogen;

R 2 represents (C 3 -C 4 )alkynyloxy or the group M;

R 3 represents H or halogen;

M is one of the groups M A and M B represented below

wherein A represents a bond, CH 2 CH 2 , CH═CH or C≡C;

R 1A represents H or halogen;

R 2A represents H, (C 1 -C 3 )alkoxy or halogen;

R 3A represents H, (C 1 -C 3 )alkoxy, hydroxy(C 1 -C 4 )alkoxy, (C 1 -C 3 )thioalkoxy, trifluoromethoxy, amino, hydroxy(C 1 -C 4 )alkyl, 2-hydroxyacetamido, 1-hydroxymethyl-cycloprop-1-yl, trans-2-hydroxymethyl-cycloprop-1-yl, 1,2-dihydroxyethyl, 3-hydroxyoxetan-3-yl, 3-(hydroxy(C 1 -C 3 )alkyl)oxetan-3-yl, 3-aminooxetan-3-yl, 3-hydroxythietan-3-yl, morpholin-4-yl(C 2 -C 3 )alkoxy, morpholin-4-yl-(C 1 -C 2 )alkyl, oxazol-2-yl or [1,2,3]triazol-2-yl; and

R 1B represents 3-hydroxyoxetan-3-yl, 3-hydroxythietan-3-yl, hydroxy(C 1 -C 3 )alkyl, amino(C 1 -C 3 )alkyl, 1-hydroxymethyl-cycloprop-1-yl or trans-2-hydroxymethyl-cycloprop-1-yl;

or a salt thereof.

3. The compound of formula I according to claim 1 , which is a compound of formula I CE

wherein

X represents N or CH;

R 1 represents H or halogen;

R 2 represents (C 3 -C 4 )alkynyloxy or the group M;

R 3 represents H or halogen;

M is one of the groups M A and M B represented below

wherein A represents a bond, CH 2 CH 2 , CH═CH or C≡C;

R 1A represents H or halogen;

R 2A represents H or (C 1 -C 3 )alkoxy;

R 3A represents H, (C 1 -C 3 )alkoxy, hydroxy(C 1 -C 4 )alkoxy, (C 1 -C 3 )thioalkoxy, trifluoromethoxy, amino, hydroxy(C 1 -C 4 )alkyl, 2-hydroxyacetamido, 1-hydroxymethyl-cycloprop-1-yl, 1-((phosphonooxy)methyl)cyclopropyl, 1-(((dimethylglycyl)oxy)methyl)cyclopropyl, trans-2-hydroxymethyl-cycloprop-1-yl, 1,2-dihydroxyethyl, 3-hydroxyoxetan-3-yl, 3-(hydroxy(C 1 -C 3 )alkyl)oxetan-3-yl, 3-hydroxythietan-3-yl, morpholin-4-yl-(C 1 -C 2 )alkyl or [1,2,3]triazol-2-yl; and

R 1B represents 3-hydroxyoxetan-3-yl, 3-hydroxythietan-3-yl, hydroxy(C 1 -C 3 )alkyl, dihydroxy(C 2 -C 4 )alkyl, amino(C 1 -C 3 )alkyl, 1-hydroxymethyl-cycloprop-1-yl, 1-aminomethyl-cycloprop-1-yl, trans-2-hydroxymethyl-cycloprop-1-yl, trans-(cis-3,4-dihydroxy)-cyclopent-1-yl or 3-hydroxymethylbicyclo[1,1,1]pentan-1-yl;

or a salt thereof.

4. The compound of formula I according to claim 1 , wherein R 1 represents H or fluorine, R 3 represents H or fluorine, R 1A represents H or fluorine and R 2A represents H;

or a salt thereof.

5. The compound of formula I according to claim 1 , wherein R 2 represents the group M A ;

or a salt thereof.

6. The compound of formula I according to claim 5 , wherein A represents a bond;

or a salt thereof.

7. The compound of formula I according to claim 5 , wherein A represents C≡C;

or a salt thereof.

8. The compound of formula I according to claim 7 , wherein R 1A represents H or fluorine, R 2A represents H and R 3A represents hydroxy(C 1 -C 4 )alkyl, trans-2-hydroxymethyl-cycloprop-1-yl, 1,2-dihydroxyethyl, 3-hydroxyoxetan-3-yl or 3-hydroxythietan-3-yl;

or a salt thereof.

9. The compound of formula I according to claim 1 , wherein R 2 represents the group M B ;

or a salt thereof.

10. The compound of formula I according to claim 9 , wherein R 1B represents 3-hydroxyoxetan-3-yl, 2-aminoprop-2-yl, 1-hydroxymethyl-cycloprop-1-yl or trans-2-hydroxymethyl-cycloprop-1-yl;

or a salt thereof.

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

(R)-4-(5-(but-2-yn-1-yloxy)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-(2-fluoro-3-methoxyphenyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-(E)-N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(5-styryl-1H-indazol-1-yl)butanamide;

(R)—N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(5-phenethyl-1H-indazol-1-yl)butanamide;

(R)—N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(5-((4-(morpholinomethyl)phenyl)ethynyl)-1H-indazol-1-yl)butanamide 4-toluenesulfonic acid salt;

(R)-4-(5-((4-aminophenyl)ethynyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(5-(4-(trifluoromethoxy)phenyl)-1H-indazol-1-yl)butanamide;

(R)-4-(5-(4-(2H-1,2,3-triazol-2-yl)phenyl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide formate;

(R)—N-hydroxy-2-methyl-2-(methylsulfonyl)-4-(5-(4-(trifluoromethoxy)phenyl)-1H-indol-1-yl)butanamide;

(R)-4-(5-(2-fluoro-4-(methylthio)phenyl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(6-fluoro-5-(2-fluoro-4-methoxyphenyl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(4-fluoro-5-(2-fluoro-4-methoxyphenyl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(4-fluoro-5-((4-(3-hydroxyoxetan-3-yl)phenyl)ethynyl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-(2-fluoro-4-(methylthio)phenyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-(2-fluoro-4-methoxyphenyl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-(2-fluoro-4-methoxyphenyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(hydroxymethyl)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((3-hydroxyoxetan-3-yl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-(4-(2H-1,2,3-triazol-2-yl)phenyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-(5-hydroxy-5-methylhexa-1,3-diyn-1-yl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(2-hydroxypropan-2-yl)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(hydroxymethyl)phenyl)ethynyl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(3-hydroxyoxetan-3-yl)phenyl)ethynyl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((3-hydroxyoxetan-3-yl)buta-1,3-diyn-1-yl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(3-hydroxyoxetan-3-yl)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((3-hydroxythietan-3-yl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(2-hydroxyethyl)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(6-fluoro-5-((4-(3-hydroxyoxetan-3-yl)phenyl)ethynyl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-((R)-1-hydroxyethyl)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-(((1S,2S)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-(((1R,2R)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-((1S,2S)-2-(hydroxymethyl)cyclopropyl)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-((1R,2R)-2-(hydroxymethyl)cyclopropyl)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-((4-((R)-1,2-dihydroxyethyl)phenyl)ethynyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-((4-((S)-1,2-dihydroxyethyl)phenyl)ethynyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-((S)-1-hydroxyethyl)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-(5-amino-5-methylhexa-1,3-diyn-1-yl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(1-(hydroxymethyl)cyclopropyl)phenyl)ethynyl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-(((1S,2S)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(2-hydroxyethoxy)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(2-hydroxyacetamido)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(2-hydroxypropan-2-yl)phenyl)ethynyl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(4-fluoro-5-((4-(3-hydroxyoxetan-3-yl)phenyl)ethynyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(4-fluoro-5-(((1S,2S)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl) butanamide;

(R)—N-hydroxy-4-(5-((3-hydroxythietan-3-yl)buta-1,3-diyn-1-yl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-((1S,2S)-2-(hydroxymethyl)cyclopropyl)phenyl)ethynyl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((1-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-((S)-1-hydroxyethyl)phenyl)ethynyl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(4-fluoro-5-((4-(2-hydroxyethyl)phenyl)ethynyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(4-fluoro-5-((4-((R)-1-hydroxyethyl)phenyl)ethynyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(4-fluoro-5-((3-hydroxyoxetan-3-yl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(4-fluoro-5-((1-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl) butanamide;

(R)-4-(4-fluoro-5-((4-(3-(hydroxymethyl)oxetan-3-yl)phenyl)ethynyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl) butanamide;

(R)-4-(6-fluoro-5-((2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-(((1R,2R)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-((2-fluoro-4-(hydroxymethyl)phenyl)ethynyl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-((4-((R)-1,2-dihydroxyethyl)phenyl)ethynyl)-1H-indol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(2-hydroxyethyl)phenyl)ethynyl)-1H-indol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(6-fluoro-5-(((1S,2S)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl) butanamide;

(R)-4-(6-fluoro-5-((4-(2-hydroxyethyl)phenyl)ethynyl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-(1-(4-((1-(4-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-4-oxobutyl)-1H-indazol-5-yl)ethynyl)phenyl)cyclopropyl)methyl dihydrogen phosphate;

(R)-(1-(4-((1-(4-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-4-oxobutyl)-1H-indazol-5-yl)ethynyl)phenyl)cyclopropyl)methyl dimethylglycinate;

(R)-4-(5-((R)-6,7-dihydroxyhepta-1,3-diyn-1-yl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)-4-(5-(((1s,3R,4S)-3,4-dihydroxycyclopentyl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((4-(1-(hydroxymethyl)cyclopropyl)phenyl)ethynyl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide;

(R)—N-hydroxy-4-(5-((3-(hydroxymethyl)bicyclo[1.1.1]pentan-1-yl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-2-methyl-2-(methylsulfonyl)butanamide; or

(R)-4-(5-((1-(aminomethyl)cyclopropyl)buta-1,3-diyn-1-yl)-1H-indazol-1-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;

or a salt thereof.

12. The compound of formula I according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is formulated as a medicament.

13. A pharmaceutical composition comprising, as active principle, 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 of treating or preventing a bacterial infection comprising administering to a subject in need thereof the compound according to claim 1 .

15. The method according to claim 14 , wherein the bacterial infection is a Gram-negative bacterial infection.