IP Library Granted Patent US 8,293,919
Granted Patent B2
US 8,293,919 · App. 12/669,597 · Granted Oct 23, 2012

Antibacterial sulfone and sulfoxide substituted heterocyclic urea compounds

Assignee: Crestone, Inc.
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Quick Facts
Patent No.
US 8,293,919
App. No.
12/669,597
Granted
Oct 23, 2012
Kind
B2
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 (111)

1. A compound of the Formula (I):

in which:

R 1 is selected from the group consisting of a substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl and substituted or unsubstituted heteroaryl;

X is selected from the group consisting of C and N atom;

Y is selected from the group consisting of SO and SO 2 ;

R 2 is selected from the group consisting of substituted or unsubstituted alcohol, substituted or unsubstituted O-alkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted linear, cyclic or branched alkyl, and perfluoroalkyl; and

R 3 is selected from the group consisting of H, halogen, alkyl, cyano and null, wherein R 3 is null when X is N.

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

3. The compound of claim 2 , wherein R 1 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 R 1 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-memethylendioxyphenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,4-dibromophenyl, 3,4-dimethylphenyl, 3,4-(-CH 2 CH 2 CH 2 -)phenyl, 3,4-(-OCH 2 CH 2 O-)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 SO 2 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 R 2 is substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted linear, cyclic or branched alkyl, or perfluoroalkyl group.

12. The compound of claim 11 , wherein R 2 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 R 3 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 R 2 -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.

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]dioxo5-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; and

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

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 .

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 .

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.

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.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2010
From: CARDIOVASCULAR SYSTEMS, INC.
To: CRESTONE, INC.
Reel/Frame 024657/0962 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2010
From: GUILES, JOSEPH; JARVIS, THALE CROSS; STRONG, SARAH; SUN, XICHENG; QIU, JIAN; ROHLOFF, JOHN C.
To: REPLIDYNE, INC.
Reel/Frame 024171/0245 →
CHANGE OF NAME Recorded Mar 31, 2010
From: REPLIDYNE, INC.
To: CARDIOVASCULAR SYSTEMS, INC.
Reel/Frame 024171/0310 →
Continuity (3)
Provisional Application 60961602 · Jul 23, 2007
Provisional Application 61022720 · Jan 22, 2008
Related Publication 20100286169A1 · Nov 11, 2010