Antibacterial Sulfone and Sulfoxide Substituted Heterocyclic Urea Compounds

• US 20100286169A1
• Filed: 07/23/2008
• Published: 11/11/2010
• Est. Priority Date: 07/23/2007
• Status: Active Grant

• Current Assignee: Crestone, Inc.
• Original Assignee: Crestone, Inc.
• Inventors: Rohloff, John C., Jarvis, Thale, Sun, Xicheng, Qiu, Jian, Strong, Sarah, Guiles, Joseph
• Granted Patent: US 8,293,919 B2
• Time in Patent Office: Days
• US Class Current: 514/255.05
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: C07D 277/48 by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
• CPC Class Codes: C07D 285/08 1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links

Abstract

The present invention provides novel sulfone and sulfoxide substituted heterocyclic urea compounds having useful antibacterial activity. Use of these compounds as pharmaceutical compositions and methods of production are provided.

Claims

1. A compound of the Formula (I):

2. The compound of claim 1, wherein R₁ is a substituted or unsubstituted phenyl or thiophene group.

3. The compound of claim 2, wherein R₁ is a phenyl group having one or more substituents selected from the group consisting of halogen, cyano, (C_1-6)alkyl, mono to perfluoro(C_1-3)alkyl, (C_3-7)cycloalkyl, (C_2-6)alkenyl, (C_1-6)alkoxy, (C_2-6)alkenoxy, hydroxy, amino, mono- or di-(C_1-6)alkylamino, acylamino, nitro, carboxy, (C_1-6)alkoxycarbonyl, (C_1-6)alkenyloxycarbonyl, (C_1-6)alkoxycarbonyl(C_1-6)alkyl, carboxy(C_1-6)alkyl, (C_1-6)alkylcarbonyloxy, carboxy(C_1-6)alkyloxy, (C_1-6)alkoxycarbonyl(C_1-6)alkoxy, (C_1-6)alkylthio, (C_1-6)alkylsulphinyl, (C_1-6)alkylsulphonyl, sulphamoyl, mono- and di-(C_1-6)-alkylsulphamoyl and carbamoyl.

4. The compound of claim 1, wherein R₁ is selected from the group consisting of 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-bromophenyl, 4-bromophenyl, 3-iodophenyl, 4-iodophenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3-methylphenyl, 4-methylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3,4-methylendioxyphenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,4-dibromophenyl, 3,4-dimethylphenyl, 3,4-(—

CH₂CH₂CH₂—

)phenyl, 3,4-(—

OCH₂CH₂O—

)phenyl, 3-chloro-4-fluorophenyl, benzo[1,3]dioxyl-5-yl, and 3-3-cyanophenyl, thiophen-2-yl, thiophen-3-yl, 4,5-di-bromo-thiophen-2yl, 5-chloro-thiophen-2yl, and 5-bromo-thiophen-2yl, 5-fluoro-thiophen-2-yl, and 3,5 difluorophenyl.

5. The compound of claim 1, wherein Y is an SO group.

6. The compound of claim 5, wherein X is a C.

7. The compound of claim 5, wherein X is a N.

8. The compound of claim 1, wherein Y is an SO₂ group.

9. The compound of claim 8, wherein X is a C.

10. The compound of claim 8, wherein X is a N.

11. The compound of claim 1, wherein R₂ is a substituted or unsubstituted alcohol, substituted or unsubstituted O-alkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted linear, cyclic or branched alkyl, or perfluoroalkyl group.

12. The compound of claim 11, wherein R₂ is selected from the group consisting of methyl, ethyl, n-propyl, cyclopropyl, n-butyl, allyl, 4-methylphenyl, 4-methylbenzyl, 4-acetamidophenyl, 4-tert-butylphenyl, 3,4-dimethylphenyl, 4-chlorophenyl, 4-chlorobenzyl, p-tolylmethyl, 4-fluorophenyl, 4-fluorobenzyl, 3-methylbutane-1-yl, 4-methoxyphenyl, 4-methoxybenzyl, 2-phenylethyl, 3,4-dimethoxyphenyl, (4-methoxyphenyl)methyl, 3,5-dimethylisoxazole-4-yl, 2-(pyrazin-2-yl)ethyl, (4-chlorophenyl)methyl, 3,3,3-trifluoropropyl, 2-(methylsulfonyl)ethyl, 3-methylphenyl, thiazole-2-yl, 2-methylpropyl, 2-methoxyethyl, 2,6-dimethylphenyl, 4-trifluoromethoxyphenyl, benzo[1,3]dioxole-5, 2,4-dimethoxyethyl, 2-(pyridin-2-yl)ethyl, 2-hydroxypropyl, 5-(methoxymethyl)-1,3,4-thiadiazole-2-yl, 2-methylbutane-1-yl, 2-methyl-tetrahydro-furan-3-yl, furan-2-ylmethyl, [1,3,4]thiadiazole-2-yl, cyclopentyl, 1-methyl-1H-imidazole-2-yl, pyridine-3-yl, benzo[1,3]dioxole-5-yl, 2-amino-ethyl, 4-methoxy-benzene, 2,4-dimethoxy-phenyl, 4-nitro-benzyl, 4-amino-benzyl, 6-methoxy-pyridine-3-yl, 2-methoxy-pyrimidine-5-yl, 2,2-difluoro-benzo[1,3]dioxole-5-yl, N-trifluoromethyl-4-carbamoyl-phenyl, 5-methoxy-pyrazine-2-yl, 5-oxo-4,5-dihydro-pyrazine-2-yl, 2-oxo-1,2-dihydro-pyrimidine-5-yl, 6-oxo-1,6-dihydro-pyridine-3-yl, pyrimidine-2-yl, 2-methylamino-pyrimidine-5-yl, 2-Dimethylamino-pyrimidine-5-yl, 4-carbamoyl-phenyl, N-methyl-4-carbamoyl-phenyl, 2-Amino-pyrimidine-5-yl, 6-methylamino-pyridine-3-yl, 2-methyl-1H-benzoimidazole-5-yl, and 2-hydroxyethyl.

13. The compound of claim 1, wherein R₃ is selected from the group consisting of H, methyl, ethyl, 2-hydroxyethyl, 2-hydroxymethyl, 2-methoxyethyl, 2-aminoethyl, propyl, cyclopropyl, isopropyl, 2,4-dimethoxybenzyl, and 2-methanesulfonylaminoethyl.

14. The compound of claim 1, wherein R₂—

Y together form a group selected from 4-methylbenzene-1-sulfonyl, 4-acetamidobenzene-1-sulfonyl, 4-tert-butylbenzene-1-sulfonyl, 3,4-dimethylbenzene-1-sulfonyl, 4-chlorobenzene-1-sulfonyl, p-tolylmethanesulfonyl, 4-fluorobenzene-1-sulfonyl, 3-methylbutane-1-sulfonyl, propane-1-sulfonyl, 4-methoxybenzene-1-sulfonyl, 2-phenylethanesulfonyl, 3,4-dimethoxybenzene-1-sulfonyl, (4-methoxyphenyl)methanesulfonyl, 3,5-dimethylisoxazole-4-sulfonyl, 2-(pyrazin-2-yl)ethanesulfonyl, 3-methylbenzene-1-sulfonyl, 3,5-dimethylisoxazole-4-sulfonyl, (4-chlorophenyl)methanesulfonyl, cyclopropane-1-sulfonyl, butane-2-sulfonyl, 3,3,3-trifluoropropane-1-sulfonyl, 2-(methylsulfonyl)ethanesulfonyl, ethane-1-sulfonyl, methanesulfonyl. thiazole-2-sulfonyl, 2-methylpropane-1-sulfonyl, 2-methoxyethanesulfonyl, 2,6-dimethylbenzene-1-sulfonyl, 4-trifluoromethoxybenzene-1-sulfonyl, benzo[1,3]dioxole-5-sulfonyl, 2,4-dimethoxyethanesulfonyl, 2-(pyridin-2-yl)ethanesulfonyl, 2-hydroxypropane-1-sulfonyl, prop-2-ene-1-sulfonyl, 5-(methoxymethyl)-1,3,4-thiadiazole-2-sulfonyl, 2-methylbutane-1-sulfonyl, propane-2-sulfonyl, 2-methyl-tetrahydro-furan-3-sulfonyl, furan-2-ylmethanesulfonyl, [1,3,4]thiadiazole-2-sulfonyl, cyclopentanesulfonyl, 1-methyl-1H-imidazole-2-sulfonyl, benzo[1,3]dioxole-5-sulfonyl, 2-amino-ethanesulfonyl, 4-methoxy-benzenesulfonyl, 2,4-dimethoxyphenylsulfonyl, pyridine-3-sulfonyl, 4-nitro-benzenesulfonyl, 4-amino-benzenesulfonyl, 6-methoxy-pyridine-3-sulfonylmethyl, 2-methoxy-pyrimidine-5-sulfonyl, 2,2-difluoro-benzo[1,3]dioxole-5-sulfonyl, N-trifluoromethyl-4-carbamoyl-phenyl-sulfonyl, 5-methoxy-pyrazine-2-sulfonyl, 5-oxo-4,5-dihydro-pyrazine-2-sulfonyl, 2-oxo-1,2-dihydro-pyrimidine-5-sulfonyl, 6-oxo-1,6-dihydro-pyridine-3-sulfonyl, pyrimidine-2-sulfonyl, 2-methylamino-pyrimidine-5-sulfonyl, 2-dimethylamino-pyrimidine-5-sulfonyl, 4-carbamoyl-phenyl-sulfonyl, N-methyl-4-carbamoyl-phenyl-sulfonyl, 2-amino-pyrimidine-5-sulfonyl, 6-methylamino-pyridine-3-sulfonyl, 2-methyl-1H-benzoimidazole-5-sulfonyl, 2-methyl-5-(sulfonyl)-1H-benzoimidazole-1-sulfonic acid, 2-hydroxyethylsulfonyl, 4-methylbenzene-1-sulfinyl, 4-acetamidobenzene-1-sulfinyl, 4-tert-butylbenzene-1-sulfinyl, 3,4-dimethylbenzene-1-sulfinyl, 4-chlorobenzene-1-sulfinyl, p-tolylmethanesulfinyl, 4-fluorobenzene-1-sulfinyl, 3-methylbutane-1-sulfinyl, propane-1-sulfinyl, 4-methoxybenzene-1-sulfinyl, 2-phenylethanesulfinyl, 3,4-dimethoxybenzene-1-sulfinyl, (4-methoxyphenyl)methanesulfinyl, 3,5-dimethylisoxazole-4-sulfinyl, 4-tert-butylbenzene-1-sulfinyl, 2-(pyrazin-2-yl)ethanesulfinyl, 3-methylbenzene-1-sulfinyl, (4-chlorophenyl)methanesulfinyl, cyclopropane-1-sulfinyl, butane-2-sulfinyl, 3,3,3-trifluoropropane-1-sulfinyl, 2-(methylsulfinyl)ethanesulfinyl, ethane-1-sulfinyl, methanesulfinyl, thiazole-2-sulfinyl, 2-methylpropane-1-sulfinyl, 2-methoxyethanesulfinyl, 2,6-dimethylbenzene-1-sulfinyl, 4-trifluoromethoxybenzene-1-sulfinyl, benzo[1,3]dioxole-5-sulfinyl, 2,4-dimethoxyethanesulfinyl, 2-(pyridin-2-yl)ethanesulfinyl, 2-hydroxypropane-1-sulfinyl, prop-2-ene-1-sulfinyl, 5-(methoxymethyl)-1,3,4-thiadiazole-2-sulfinyl, and 2-methylbutane-1-sulfinyl, propane-2-sulfinyl, (2-methyl-tetrahydro-furan-3-sulfinyl, furan-2-ylmethanesulfinyl, [1,3,4]thiadiazole-2-sulfinyl, cyclopentanesulfinyl, 1-methyl-1H-imidazole-2-sulfinyl, benzo[1,3]dioxole-5-sulfinyl, 2-amino-ethanesulfinyl, 4-methoxy-benzenesulfinyl, 2,4-dimethoxyphenylsulfinyl, pyridine-3-sulfinyl, 4-nitro-benzenesulfinyl, 4-amino-benzenesulfinyl, 6-methoxy-pyridine-3-sulfinylmethyl, 2-methoxy-pyrimidine-5-sulfinyl, 2,2-difluoro-benzo[1,3]dioxole-5-sulfinyl, N-trifluoromethyl-4-carbamoyl-phenyl-sulfinyl, 5-methoxy-pyrazine-2-sulfinyl, 5-oxo-4,5-dihydro-pyrazine-2-sulfinyl, 2-oxo-1,2-dihydro-pyrimidine-5-sulfinyl, 6-oxo-1,6-dihydro-pyridine-3-sulfinyl, pyrimidine-2-sulfinyl, 2-methylamino-pyrimidine-5-sulfinyl, 2-dimethylamino-pyrimidine-5-sulfinyl, 4-carbamoyl-phenyl-sulfinyl, N-methyl-4-carbamoyl-phenyl-sulfinyl, 2-amino-pyrimidine-5-sulfinyl, 6-methylamino-pyridine-3-sulfinyl, 2-methyl-1H-benzoimidazole-5-sulfinyl, 2-methyl-5-(sulfinyl)-1H-benzo[d]imidazole-1-sulfonic acid, and 2-hydroxyethylsulfinyl.

16. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt of a compound of claim 1.

18. A method for protecting a patient from a bacterial infection comprising administering a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt of a compound of claim 1 to a patient in need thereof.

15. A compound selected from the group consisting of:

1-(3,4-dichlorobenzyl)-3-(4-(tosylmethyl)thiazol-2-yl)urea;

N-(4-((2-(3-(3,4-dichlorobenzyl)ureido)thiazol-4-yl)methylsulfonyl)phenyl)acetamide;

1-(3,4-dichlorobenzyl)-3-(4-((4-(trifluoromethyl)phenylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((3,4-dimethylphenylsulfonyl)methyl)thiazol-2-yl)urea;

1-(4-((4-chlorophenylsulfonyl)methyl)thiazol-2-yl)-3-(3,4-dichlorobenzyl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((4-methylbenzylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((4-fluorophenylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-(isopentylsulfonylmethyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-(propylsulfonylmethyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((4-methoxyphenylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-(phenethylsulfonylmethyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((3,4-dimethoxyphenylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((4-methoxybenzylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((3,5-dimethylisoxazol-4-ylsulfonyl)methyl)thiazol-2-yl)urea;

1-(4-((4-tert-butylphenylsulfonyl)methyl)thiazol-2-yl)-3-(3,4-dichlorobenzyl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((2-(pyrazin-2-yl)ethylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-(m-tolylsulfonylmethyl)thiazol-2-yl)urea;

1-(4-((3,5-dimethylisoxazol-4-ylsulfonyl)methyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea;

1-(4-((4-chlorobenzylsulfonyl)methyl)thiazol-2-yl)-3-(3,4-dichlorobenzyl)urea;

1-(3-fluorobenzyl)-3-(4-(propylsulfonylmethyl)thiazol-2-yl)urea;

1-(4-(cyclopropylsulfonylmethyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea;

1-(4-(sec-butylsulfonylmethyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea;

1-(3-fluorobenzyl)-3-(4-((3,3,3-trifluoropropylsulfonyl)methyl)thiazol-2-yl)urea;

1-(4-(butylsulfonylmethyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((2-(methylsulfonyl)ethylsulfonyl)methyl)thiazol-2-yl)urea;

1-(4-(ethylsulfonylmethyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea;

1-(3-fluorobenzyl)-3-(4-(m-tolylsulfonylmethyl)thiazol-2-yl)urea;

1-(4-((3,4-dimethoxyphenylsulfonyl)methyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea;

1-(3-fluorobenzyl)-3-(4-(methylsulfonylmethyl)thiazol-2-yl)urea;

1-(3-fluorobenzyl)-3-(4-(tosylmethyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((thiazol-2-ylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3-fluorobenzyl)-3-(4-(isobutylsulfonylmethyl)thiazol-2-yl)urea;

N-(4-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methylsulfonyl)phenyl)acetamide;

1-(3,4-dichlorobenzyl)-3-(4-((2-methoxyethylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((2,6-dimethylphenylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((4-(trifluoromethoxy)phenylsulfonyl)methyl)thiazol-2-yl)urea;

1-(4-((benzo[d][1,3]dioxol-5-ylsulfonyl)methyl)thiazol-2-yl)-3-(3,4-dichlorobenzyl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((2,4-dimethoxyphenylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((2-(pyridin-2-yl)ethylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3-fluorobenzyl)-3-(4-((2-hydroxypropylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3,5-difluorobenzyl)-3-(4-(propylsulfonylmethyl)thiazol-2-yl)urea;

1-(4-(allylsulfonylmethyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((5-(methoxymethyl)-1,3,4-thiadiazol-2-ylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3-fluorobenzyl)-3-(4-((2-methylbutylsulfonyl)methyl)thiazol-2-yl)urea;

1-(3-fluorobenzyl)-3-(4-(isopropylsulfonylmethyl)thiazol-2-yl)urea;

1-(3-Fluoro-benzyl)-3-[4-(2-methyl-tetrahydro-furan-3-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-(furan-2-ylmethanesulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-([1,3,4]thiadiazole-2-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(4-Cyclopentanesulfonylmethyl-thiazol-2-yl)-3-(3-fluoro-benzyl)-urea;

1-(3-Fluoro-benzyl)-3-[4-(1-methyl-1H-imidazole-2-sulfonylmethyl)-thiazol-2-yl]-urea;

1-[4-(Propane-1-sulfonylmethyl)-thiazol-2-yl]-3-thiophen-3-ylmethyl-urea;

1-(5-Fluoro-thiophen-2-ylmethyl)-3-[4-(propane-1-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(5-Chloro-thiophen-2-ylmethyl)-3-[4-(propane-1-sulfonylmethyl)-thiazol-2-yl]-urea;

N-(3-{2-[3-(3-Fluoro-benzyl)-ureido]-thiazol-4-ylmethanesulfonyl}-phenyl)-acetamide;

1-(3-Fluoro-benzyl)-3-[4-(pyridine-3-sulfonylmethyl)-thiazol-2-yl]-urea;

1-[4-(Benzo[1,3]dioxole-5-sulfonylmethyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea;

1-[4-(2-Amino-ethanesulfonylmethyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea;

1-(3-Fluoro-benzyl)-3-[4-(4-methoxy-benzenesulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-(4-nitro-benzenesulfonylmethyl)-thiazol-2-yl]-urea;

1-[4-(4-Amino-benzenesulfonylmethyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea;

1-(3-Fluoro-benzyl)-3-[4-(6-methoxy-pyridine-3-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-(2-methoxy-pyrimidine-5-sulfonylmethyl)-thiazol-2-yl]-urea;

1-[4-(2,2-Difluoro-benzo[1,3]dioxole-5-sulfonylmethyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea;

2,2,2-Trifluoro-N-(4-{2-[3-(3-fluoro-benzyl)-ureido]-thiazol-4-ylmethanesulfonyl}-phenyl)-acetamide;

1-(3-Fluoro-benzyl)-3-[4-(5-methoxy-pyrazine-2-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-(5-oxo-4,5-dihydro-pyrazine-2-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-(2-oxo-1,2-dihydro-pyrimidine-5-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-(6-oxo-1,6-dihydro-pyridine-3-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-(pyrimidine-2-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-(2-methylamino-pyrimidine-5-sulfonylmethyl)-thiazol-2-yl]-urea;

1-[4-(2-Dimethylamino-pyrimidine-5-sulfonylmethyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea;

4-{2-[3-(3-Fluoro-benzyl)-ureido]-thiazol-4-ylmethanesulfonyl}-benzamide;

4-{2-[3-(3-Fluoro-benzyl)-ureido]-thiazol-4-ylmethanesulfonyl}-N-methyl-benzamide;

1-[4-(2-Amino-pyrimidine-5-sulfonylmethyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea;

1-(3-Fluoro-benzyl)-3-[4-(6-methylamino-pyridine-3-sulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-Fluoro-benzyl)-3-[4-(2-methyl-1H-benzoimidazole-5-sulfonylmethyl)-thiazol-2-yl]-urea;

5-{2-[3-(3-Fluoro-benzyl)-ureido]-thiazol-4-ylmethanesulfonyl}-2-methyl-benzoimidazole-1-sulfonic acid;

1-(3-Fluoro-benzyl)-3-[5-fluoro-4-(4-methoxy-benzenesulfonylmethyl)-thiazol-2-yl]-urea;

1-(3-((3,5-dimethylisoxazol-4-ylsulfonyl)methyl)-1,2,4-thiadiazol-5-yl)-3-(3-fluorobenzyl)urea;

1-(3-fluorobenzyl)-3-(3-(propylsulfonylmethyl)-1,2,4-thiadiazol-5-yl)urea;

1-(3-fluorobenzyl)-3-(3-((2-hydroxyethylsulfonyl)methyl)-1,2,4-thiadiazol-5-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-(propylsulfinylmethyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((2,6-dimethylphenylsulfinyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((4-methoxybenzylsulfinyl)methyl)thiazol-2-yl)urea;

1-(3,4-dichlorobenzyl)-3-(4-((4-fluorophenylsulfinyl)methyl)thiazol-2-yl)urea;

1-(4-((4-chlorophenylsulfinyl)methyl)thiazol-2-yl)-3-(3,4-dichlorobenzyl)urea.

17. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 15 or a pharmaceutically acceptable salt of a compound of claim 15.

19. A method for protecting a patient from a bacterial infection comprising administering a therapeutically effective amount of a compound of claim 15 or a pharmaceutically acceptable salt of a compound of claim 15 to a patient in need thereof.