Ethanol or 1,2-ethanediol cyclohexyl antibiotic derivatives

1. A compound of formula I

wherein

R 1 represents (C 1 -C 4 )alkoxy;

one or two of U, V, W and X represent(s) N, and the remaining represent each independently CH or, in the case of V or X, may also represent CR a ;

R a represents halogen;

R 2 represents H or OH;

A represents CH 2 , CO, CH 2 CH═CH or COCH═CH;

D represents a phenyl group optionally substituted one or two times by halogen atoms, or D represents a group of the formula

 in which Q is oxygen or sulfur;

or a salt of said compound.

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

or a salt of said compound.

3. The compound of formula I according to claim 1 , wherein one or two of U, V, W and X represent(s) N, and the remaining represent each independently CH or, in the case of V or X, may also represent CR a , where R a represents fluorine;

or a salt of said compound.

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

wherein

D is a phenyl group optionally substituted one or two times by halogen atoms;

or a salt of said compound.

5. The compound of formula I according to claim 4 , wherein D represents 3-fluorophenyl or 2,5-difluorophenyl;

or a salt of said compound.

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

wherein

D is a group of the formula

in which Q is oxygen or sulfur;

or a salt of said compound.

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

-6-({trans-4-[(1R)-1-hydroxy-2-(3-methoxy-quinolin-5-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

-6-({trans-4-[(1S)-1-hydroxy-2-(3-methoxy-quinolin-5-yl)-ethyl]-cyclohexylamino }-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid trans-{4-[(1R,2R)-1,2-dihydroxy-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexyl}-amide;

-6-(trans-{4-[(1R,2R)-1,2-dihydroxy-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid trans-{4-[(1S)-1-hydroxy-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexyl}-amide;

-6-(trans-{4-[(1S)-1-hydroxy-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

-6({trans-4-[(1R,2R)-1,2-dihydroxy-2-(3-methoxy-quinoxalin-5-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

- 6-(trans-{4[(1S,2S)-1,2-dihydroxy-2-(3-methoxy-quinoxalin-5-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one ;

-6-({trans-4-[(1S,2S)-1,2-dihydroxy-2-(3-methoxy-quinoxalin-5-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one;

-6-(trans-{4-[(1S,2S)-1,2-dihydroxy-2-(3-methoxy-quinoxalin-5-yl)-ethyl]-cyclohexylaminol}-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one;

-(1R,2R)-1-{trans-4-[(E)-3-(2,5-difluoro-phenyl)-allylamino]-cyclohexyl}-2-(3-methoxy -quinoxalin-5-yl)ethane-1,2-diol;

-6-(trans-{4-[(1R)-1-hydroxy-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[3,2-b][1,4]thiazin-3-one ;

-6-(trans {4-[(1R)-1-hydroxy-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexylamino }-methyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one;

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

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

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

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

-(1R,2R)-1-{4-trans-[(E)-3-(2,5-difluoro-phenyl)-allylaminol]-cyclohexyl}-2-(6-methoxy -[1,5]naphthyridin-4-yl)-ethane-1,2-diol;

-(1R,2R)-1-{trans-4-[(E)-3-(2,5-difluoro-phenyl) -allylamino]-cyclohexyl}-2-(8-fluoro -6-methoxy-quinolin-4-yl)-ethane-1,2-diol;

-(E)-3-(2,5-difluoro-phenyl)-N-{trans-4-[(1R,2R)-2-(8-fluoro-6-methoxy-quinolin-4-yl) -1,2-dihydroxy-ethyl]-cyclohexyl }-acrylamide;

-6-({trans-4-[(1R,2R)-2-(8-fluoro-6-methoxy-quinolin-4-yl)-1,2-dihydroxy-ethyl]-cyclohexylamino}-methyl)-4H-pyrido[--3,2-b][1,4]thiazin-3-one;

-3-(2,5-difluoro-phenyl)-N-{4-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl) -1,2-dihydroxy-ethyl]-cyclohexyl}-acrylamide;

-(1R,2R)-1-{ trans-4-[(E)-3-(2,5-difluoro-phenyl)-allylamino]-cyclohexyl)-2-(3-fluoro -6-methoxy-[1,5]naphthyridin-4-ye-ethane-1,2-diol;

-(1R,2R)-1-(3-fluoro-6-methoxy-[1,5]naphthyridin-4-yl)-2-{trans-4-[(E)-3-(3-fluoro -phenyl)-allylamino]-cyclohexyl}-ethane-1,2-diol;

or a salt of said compound.

8. A medicament comprising the compound of formula I as defined in claim 1 or a pharmaceutically acceptable salt of said compound.

9. A pharmaceutical composition comprising, as active principle, the compound of formula I as defined in claim 1 or a pharmaceutically acceptable salt of said compound, and at least one therapeutically inert excipient.

10. A method for treating a bacterial infection comprising administering the compound of formula I as defined in claim I to a patient in need thereof, wherein the bacterial infection is caused by Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, Staphylococcus aureus, Enterococcus faecalis, Enterococcus faecium, Enterococcus casseliflavus, Staphylococcus epidermidis , Streptococcus haemolyticus, Staphylococcus haemolyticus, Peptostreptococcus, Streptococcus pyogenes , Groups C and G streptococci, Corynebacterium diphtheriae, Actinobacillus haemolyticum, Mycoplasma pneumoniae, Legionella pneumophila, Chlamydia pneumoniae, Enterococcus durans , coagulase-negative staphylococci, Streptococcus agalactiae, Streptococcal groups C-F, viridans streptococci, Corynebacterium minutissimum, Clostridium, Bartonella henselae, Enterococcus, Chlamydia trachomatis, Haemophilus ducreyi, Treponema pallidum, Ureaplasma urealyticum, Neiserria gonorrhea , Groups A, B, and C streptococci, Helicobacter pylori, Borrelia recurrentis, Borrelia burgdorferi, Chlamydia trachomatis, Listeria, Mycobacterium avium, Mycobacterium intracellulare, Mycobacterium tuberculosis. Mycobacterium leprae, Mycobacterium paratuberculosis, Mycobacterium kansasii, Mycobacterium chelonei, Campylobacter jejuni. Cryptosporidium spp., Bordetella pertussis, Clostridium perfringens, or Bacteroide.

11. The method of claim 10 , wherein the bacterial infection is caused by E. coli, Klebsiella pneumoniae and other Enterobacteriaceae, Acinetobacter, Stenothrophomonas maltophilia, Neisseria meningitidis, Bacillus cereus, Bacillus anthracis, Corynebacterium, Propionibacterium acnes , or Bacteroide.

12. The method of claim 10 , wherein the bacterial infection is caused by Staphylococcus aureus.

13. The method of claim 10 , wherein the bacterial infection is caused by Streptococcus pneumoniae.

14. The method of claim 10 , wherein the bacterial infection is caused by Moraxella catarrhalis.

15. A method for treating a protozoal infection comprising administering the compound of formula I as defined in claim 1 to a patient in need thereof, wherein the protozoal infection is caused by Plasmodium malaria, Plasmodium falciparum, Toxoplasma gondii, Pneumocystis carinii, Trypanosoma brucei , or Leishmania.