Claims
1. A compound of formula I

wherein
R! is H or halogen;
R2 is the group M;
R.J is H or halogen;
M is one of the groups MA and Ml! represented below


R'

M'

M1

10

wherein A represents a bond or C=C;
R1A is H or halogen;
R is H, (C]-C;,)alkoxy or halogen;
R1A is H, (C]-C:,)alkoxy, hydroxy(C2-C,.i)alkoxy, hydroxy(C]-C4)alkyl, 1,2-dihydroxycthyl,
di(Ci-C;,)alkylamino, l-hydroxymethyl-cycloprop-l-yl, l-((dimcthylglycyl)oxy)mcthyl-

cycloprop-1-yi, 3-hydroxyoxctan-3-yl, morpholin-4-yl-(Ci-C2)alkyl or morpholin-4-yl(C2-C\)aikoxy; and
R1B is hydroxy(C,-COaikyi, amino(CrCOalkyI, [di(Ci~C;)alkylamino]-(C]-C,)alkyl,
1,2-dihydroxyprop-3~y I, 1 -amino-cy cloprop-1 -yl, 1 -hydroxym ethyl-cycloprop-1 -y 1,
l-((phosphonooxy)methyl)cycloprop-l-yl, fr'ans-2-hydroxymethyl-cycloprop-l-yl,
rr#m--2-aminomcthyl-cycloprop-l-yl, l-fiuoro-2-hydroxymethyI-cycloprop-l-yl,
^-a/75-2-hydroxymcthyl-l-mcthyi-cycloprop-l-yl, 2-fluoro-2-hydroxymcthyI-cycloprop-
1 -yl, trans-2-b.ydroxymethy1-2-methy 1-cycloprop-1 -y 1, 1 -(1,2-dihydroxycthyl)-cyeloprop-
1 -yl, /VYW5-2-(l?2-dihydroxyethyr)-cycloprop--l-yl, l-(hydroxymethyl)cyciobul-l-yl,
3~hydroxyoxetan-3-yl, 3-(hydroxy(Ci-C3)aIkyi)oxetan-3-yl, 3-hydroxythietan-3-yl,
/r«/?.s'-(67'v-3,4-dihydroxy)-cyclopcnt~l~yl, 3-(2-aminoacctamido)cyciopentyl;
3-hydroxymethylbicyclo[l,l,l]pcntan-l-yl or 3-hydroxyoxetan-3-ylmethyl;
or a sait of this compound.
wherein
R1 is H or haiogen; R2 is the group M; R"' is H or halogen;

wherein A represents a bond or C=C;
R1A is H or halogen;
R is H, (Ci-C^alkoxy or halogen;
R3A is H, (C]-Q)alkoxy, hydi"Oxy(C2-C^)alkoxy, hydroxy(Ci-C4)alkyl, 1,2-dihydroxycthyl,
di(Cj~CV)alkylamino, i-hydroxymethyl-cycloprop-1-yl, l-((dimcthylgIycyi)oxy)methyl-
cycloprop-l-yl, 3-hydroxyoxctan-3-yI, morpholin-4-yl-(Ci-C2)alkyl or morpholin-
4-yl(C2-C3)alkoxy; and
R1B is hydroxy(Ci-C:,)aIkyI, amino(Ci-Ci)aikyl, dimcthyiamino-(CrCV)alkyl,
l,2-dihydroxyprop~3-yl, 1-amino-cycloprop-l-yl, J-hydroxymethyl-cycloprop-1-yl,
1 -((phosphonooxy)methyl)cycloprop-1 -yl, /'rs,-2-(l,2-dihydroxyethyl)-cycioprop-]-yl, r;r/m--(m-3,4-dihydroxy)-cyclopent-l-yl or 3-hydroxymethylbicyclo[ 1,1,1 jpentan-1 -yl;
or a salt this compound.
TLA compound of formula I according to claim 1, which is selected from the following:
- (j^)-4-(7-(2-fluoro-4-mcthoxyphenyl)-4-oxoquinazolin-3(4//)-yl)-A'-hydroxy-2-methyl-2-(mcthylsulfonyl)butanamide;
- (/?)-A^-hydroxy-2-methyl-2-(methylsulfonyl)-4-(4-oxo-7-phenylquinazolin~ 3(4//)-yl)butanamide;
-(^)-;V4iydroxy-4-(7-(((;S,^)-2-(hydroxymethyl)cyclopropyl)buta-13-diyn-l-yl)-4-oxoquinazolin-3(4i/)-yl)-2-methyl-2-(methylsulfonyl)butanamide;
- (i?)-AMiydroxy-4-(7-((3-hydroxyoxetan-3-yl)buta-1 ,3-diyn-1 -yl)-4-oxoquinazolin-
3(4/y)-yl)-2-mcthyl-2-(methylsulfonyl)butanamidc;
-(/?)-A^-hydroxy-4-(7-(((^,^)-2-(hydroxymethyl)cyclopropyI)buta-l,3-diyn-l-yl)-4-oxoquinazolin-3(4//)-yl)-2-methyl-2-(methylsuIfonyl)butanamidc;
- (/?)-/V-hydroxy-4-(7-(( 1 -(hydroxymethyl)cyclopropyl)buta-1,3-diyn-l -yl)-4-oxoquinazolin-3(4/7)-yl)-2-methyl-2-(methy!sulfonyl)butanamide;
- (7?)-4-(7-(5-amino-5-methylhexa-l,3-diy^-l-yl)-4-oxoquinazolin-3(4/-/)-yi)-A/-hydroxy-2-methyl-2-(methyIsulfonyl)butanamidc;
- (^)-A^-hydroxy-4-(7-((4-(2-hydroxycthyl)phcnyl)ethynyl)"4-oxoquinazolin-3(4//)-yJ)-2-methy]-2-(methylsulfonyl)butanamide;
-(/?)-4-(6-fluoro-7-(((/1S,25)-2-(hydroxymethyl)cyclopropyr)buta-l,3-diyn-l-yl)-4-oxoquinazolin-3(4/f)-yl)-jV~hydroxy-2-methyl-2-(methylsulfonyl)butanamide; -(^)-4-(7-((^)-5,6-dihydroxyhcxa-],3-diyn-l-yl)-4-oxoquinazolin~3(4//)-yl)-A/-hydroxy-2-methyl-2-(methylsulfonyI)butanamidc;
-(^)-4-(6-fluoro-7-(((//?,2/?)-2-(hydroxymcthyl)cyclopropyl)buta-K3-diyn-l-yl)-4~oxoquinazolin-3(4/f)-yl)--'V-hydroxy-2-mcthyl-2-(methylsuIfonyl)butanamide;
- (/?)-4-(6-fluoro-7~(( 1 -(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1 -yl)-4-oxoquinazolin~
3(4/7)-yr)-A?-hydroxy-2-methyl-2~(methylsulfonyl)butanamide;

- (^)-iV-hydroxy-4-(7-((3-(hydroxymcthyl)bicyclo[l.1 . l]pcntan-l-yi)buta-l,3-diyn-l-yl 4-oxoquinazolin-3(4//)-yl)-2-methyl-2-(methyLsulfonyl)butanamidc;
- (/?)-A/-hydroxy-4-(7-((4-(2-hydroxycthoxy)plicayl)ethynyl)-4-oxoquinazolin-3(4//)-yr 2-methyl-2-(mcthylsiilfonyl)butanamidc;
- (/?)-4-(7-(((/i-,5^,^5)-3,4-dihydroxycyciopentyl)buta-l,3-diyn-l-yl)-4-oxoquinazolin-3(4/f)-yl)-A^-hydroxy-2-methyl-2-(methy{suIfonyl)butanamidc;
- (^)-A'-hydroxy-4-(7-((4-(l-(hydroxymcthyl)cyclopropyl)phenyl)cthynyl)-4-oxoquinazolin-3(4i1/)-yl)-2-mcthyl-2-(mcthylsulfonyl)butanamide;
- (^)-A^-hydroxy-4-(7-(((/1S,2^)~2-(hydroxymethyl)-2-mcthylcyclopropyl)buta~ 1,3-diyn-l-yl)-4-oxoquinazolin-3(4//)-yr)-2-methyl-2-fmethyIsulfonyl)butanamide; -(^H-(7-((4-((/?)-l,2-dihydroxyethyl)phenyl)ethynyl)-4~oxoquinazolin-3(4//)-yi)-jY~hydroxy-2-methyi-2-(methylsuifonyl)biitanamide;
- (2i?)-4-(7-(( 1 -(1,2-dihydroxycthyl)cyclopropyl)buta-l ,3-diyn-1 -yl)-4~oxoquinazoiin-3(4//)-yl)-A'-hydroxy~2-melhyl-2-(meihylsuifonyl)butanamide;
- (i?)-A?-hydroxy-4-(7-(((/ff,2/?)-2-(hydroxymelhyl)-l-mcthylcyclopropyl)buta-l,3-diyn-l~yl)-4-oxoquinazolin-3(4//)-yl)-2-mctliyl-2-(mediylsulfony])butanamide; -(/?)-4-(8-fluoro-7-(((/^,2^)-2-(hydroxymcthy!)cyclopropyl)buta-],3-diyn-l-yl)-4-oxoquinazolin-3(4//)-yl)-/^-hydroxy-2~mcthyi-2-(mctliylsiilfonyl)butanamide;
- (i?)-(l-(4-((3-(4-(hydroxyamino)-3-rncthyl-3-(mcthylsiilfotiyl)-4-oxobutyl)-4-oxo-3,4-dihydroquinazolin~7-yI)ethynyI)phcnyl)cyclopropyl)methyl dimetbylglycinate; -(^^-(S-fluoro^-^ty^^^-thydroxymelhyOcyclopropyljbuta-l^-diyn-l-yl)-4-oxoqiiinazolin-3(4//)~yl)~A/--hydroxy-2--methyl-2-(mcthylsiilfony[)biitanamide;
- (i?)-7V4iydroxy-4-(7-(((/A,25')-2-(hydroxymethyi)-2-mcthyicyclopropyi)buta-l;3-diyn-l-yi)-4-oxoquinazolin-3(4//)-yl)-2-mcthyi-2-(mcthyIsuIfonyl)butanamide;
- (^)-4-(7-((l-aminocycIopropyr)bu(a-l,3"diyn-I-yi)-4-oxoquinazolin-3(4//)-yl)-A/-hydroxy-2-methyI-2-(methylsulfonyr)butanamide;
-(i?)-4-(7-(((7i2,^)-2-((5)-l,2-dihydroxyethyl)cyclopropyl)buta-l,3-diyn-l-yl)-4-oxoqiiinazolin-3(4//)-y3)-.^bydroxy--2--methyl--2-(methylsulfonyl)biitanamide;
- (^)-4-(7-((3-(2-aminoacetamido)cyciopentyI)buta-l,3-diyn-l-yl)-6-fluoro-4-oxoqiiinazolin-3(4//)-yl)-AMiydroxy-2-methyl-2-(methylsuIfonyl)bii(anamide;
- (^)-4-(7-(((77?,„97f)-2-(aminomcthyl)cyclopropyi)buta-1,3-diyn-1 -yl)-6-fluoro-4-oxoquinazolin-3(4/^)-yl)-.'V-hydroxy-2-methyl-2-(mcthylsulfonyr)butanamide;

- (7?)-4-(6-fluoro-7-(5-hydroxy-5-mcthylhcxa-l,3-diyn-l-yl)-4-oxoquinazoIin-3(4//)-yl)-7V-hydroxy-2-methyI-2-(methylsulfonyl)butanamide;
- (i?)-4-(7-(2-fluoro-4-(3-morpholinopropoxy)phcnyl)-4-oxoquinazolin-3(4//)-yl)-
iV-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;
- (/?)-yV-hydroxy-2-mcthyI-2-(methylsu1fonyl)-4-(7-(4-(3-Tnorpholinopropoxy)phcnyl)-4-oxoquinazolin-3(4#)-yl)butanamide;
- (^)-4-(7-(2-fluoro-4-(2-morphoiinocthoxy)phcnyl)-4-oxoquinazolin-3(4i1/)-yl)-A?-hydroxy-2-methyl-2-(methyLsulfonyl)butanamide;
- (/?)~4-(7-(2-fluoro-3-mcthoxyphenyl)-4-oxoquinazoIin-3(4ii/)-yl)-iV-hydroxy-2-mcthyl-2-(methylsulfonyl)butanamidc;
- (/?)-4-(7-(3-fluoro-4-methoxyphenyl)-4-oxoquinazolin-3(4//)-yI)~A^-hydroxy-2-methyl-2-(methylsulfonyl)butanamidc;
-(^)-4-(7-(4-(dimethylamino)phenyf)-4-oxoquinazolin-3(4//)-yl)-A/-hydroxy-2-methyl-2-(methylsulfonyl)butanamide;
- (/?)-A/-hydroxy-4-(7-(4-(hydroxymethyl)phenyl)-4-oxoquinazolin-3(4//;)~yI)-2-mc£hyl-2-(mcthylsulftmyI)biitanamide;
- (y?)-A/-hydroxy-2-methyl-2-(niethylsuIfonyl)-4-(7-(4-(morpholinomethyl)phcnyl)-4-oxoquinazolin-3(4//)-yl)butanamide;
- (^,)-4-(6-fluoro-4-oxo-7-phcnylquinazolin-3(4//)-yl)-A^-hydroxy-2-mcthyl" 2-mcthytsulfonyl)butanamide;
■ (^)-A/-hydroxy-4-(7-((4-(hydroxymethyl)phenyl)elhynyl)-4-oxoquinazoIin-3(4/f)-yl)-2-methyl-2-(mcthylsulfonyl)butanamide;
- (/?)-A^-hydroxy-4-(7-((4-(3-hydroxyoxetan-3-yl)phenyl)cthynyl)-4-oxoquinazolin-3(4//)-yI)-2-mcthyl-2-(methylsuIfonyl)butanamidc;
- (7?)-/V-hydroxy-2-mcthyi-2-(mcthylsulfonyl)-
4-(7-((4~(morphoIinomcthyl)phcnyl)cthynyi)-4-oxoquinazolin-3(4i^)-yl)butanamide; -(/?)-4-(7-(((//?*,2/?*)-l-fluoro-2-(hydroxymethyl)cyclopropyl)buta-ls3-diyn-l-yl)-4-oxoquinazolin-3(4//)-yl)-A'-hydroxy-2-methyl-2-(methylsulfonyI)butanarnide;
- (R)-4-(7-(((lK*,2R*)-1 -fluoro-2-(hydroxymethyl)cyclopropyl)biita-1,3-diyn-3-yI)-4-oxoquinazoIin-3(4/f)~yl)-AMiydroxy-2-methyl-2-(methylsulfonyl)butanamide;
- (/?)-(l-((3-(4-(hydroxyamino)-3-mcthyl-3-(mcthylsulfonyl)-4-oxobutyl)-4-oxo-3,4-dihydroquinazoIin-7-yl)buta-l,3-diyn-J-yl)cyclopropyl)methyl dihydrogen phosphate

- (y?)-4-(7-(5-(dimcthylamino)pcnta-],3-diyn-l-yl)-6-fluoro-4-oxoquinazolin-3(4//)-yr)-
Ar-hydroxy-2-methyl-2-(methylsuIfonyl)butanamidc;
-(i?)-4-(7-(((l^*,2i?*)-2-fluoro-2-(hydroxymethyl)cyclopropyl)buta-l,3-diyn-I-yl)-4-oxoquinazolin-3(4//}-yi)-7V-hydroxy-2-mcthyl-2-(mcthylsulfonyl)butanamidc;
- (/?)-4-(6-fluoro-7-((l-(hydroxytnethyl)cyclobutyl)buta-l,3-diyn-l»yl)-4-oxoquinazolin-3(4/7)-yl)-A'-hydroxy-2-methyI-2-(methylsulfonyl)butanamide; and
- (i?)-4-(6-fluoro-7-(5-(3-hydroxyoxctan-3-yI)pcnta-l,3-diyri-l-yl)-4-oxoquinazolin-3(4//)-yl)-AMrydroxy-2-mcthyl-2-(methylsu!fonyl)butanamide;
or a salt of this compound.
12. A compound of formula I as defined in one of claims 1 to 11, or a pharmaceutically acceptable salt thereof, for use as a medicament.
13. A pharmaceutical composition containing, as active principle, a compound of formula I as defined in one of claims 1 to 11, or a pharmaceutically acceptable salt thereof, and at least one therapeutically inert excipient.
14. A compound of formula 1 as defined in one of claims .1 to 11, or a pharmaceutically acceptable salt thereof, for the prevention or treatment of a bacterial infection.
15. A compound or pharmaceutically acceptable salt according to claim 14, which is for the prevention or treatment of a Gram-negative bacterial infection.