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US 8,716,320 B2Granted
Antibacteriall heterocyclic ureas
AssigneeReplidyne, Inc.
InventorsJoseph Guiles, Thale Jarvis, Sarah Strong, Xicheng Sun
Life of this patent
Estimating the term…
Abstract
The present invention provides novel heterocyclic urea compounds having useful antibacterial activity, pharmaceutical compositions comprising one or more of these compounds, methods of making the same, and methods of using the same.
Claims25
A compound of the Formula (I):
- in which:
- R1 is selected from the group consisting of substituted aryl, unsubstituted aryl, substituted arylalkyl, unsubstituted arylalkyl, substituted heteroaryl and unsubstituted heteroaryl;
- X and X′ are independently selected from the group consisting of a C and N atom;
- Y is selected from the group consisting of a O, S and N atom;
- R2 and R2′ are independently selected from the group consisting of H, substituted linear, cyclic, or branched alkyl, unsubstituted linear, cyclic or branched alkyl, and perfluoroalkyl;
- R3 and R3′ are independently selected from the group consisting of null, H, halogen, and
- wherein one of R3 or R3′, but not both, is
- wherein R3 or R3′ is null when X or X′, respectively, is N;
- R4 and R4′ are independently selected from the group consisting of H, substituted linear, cyclic, or branched alkyl, unsubstituted linear, cyclic, or branched alkyl, perfluoroalkyl;
- and
- wherein when Y is O or S, R6 is null, R5 is selected from the group consisting of null, H, O, OH, substituted O-alkyl, unsubstituted O-alkyl, substituted aryl, unsubstituted aryl, substituted arylalkyl, unsubstituted arylalkyl, substituted linear, cyclic, or branched alkyl, unsubstituted linear, cyclic or branched alkyl, and perfluoroalkyl;
- wherein when Y is N, R5 is selected from the group consisting of null, H, O, OH, substituted O-alkyl, unsubstituted O-alkyl, substituted aryl, unsubstituted aryl, substituted arylalkyl, unsubstituted arylalkyl, substituted linear, cyclic, or branched alkyl, unsubstituted linear, cyclic or branched alkyl, and perfluoroalkyl, R6 is selected from the group consisting of null, O, OH, substituted O-alkyl, unsubstituted O-alkyl, substituted aryl, unsubstituted aryl, substituted arylalkyl, unsubstituted arylalkyl, substituted linear, cyclic, or branched alkyl, unsubstituted linear, cyclic or branched alkyl, and perfluoroalkyl, R5 and R6 together can form a 4, 5, or 6 member saturated ring comprising carbon atoms or comprising at least one carbon atom and one or more heteroatoms selected from O and NR7,
- wherein R7 is selected from the group consisting of substituted or unsubstituted C(1-6)alkyl, substituted or unsubstituted C(1-6)acyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and
- wherein R5, R6, and NR7 together can form a 4,4-, 4,5-, 5,5-, 5,6-, or 6,6-saturated bicyclic ring system comprising carbon atoms or comprising at least one carbon atom and one or more heteroatoms selected from O and N.
11 more elements
A compound of Formula (Ia):
- in which:
- R5 is selected from the group consisting of Me-, MeO(CH2)2—, CH3(CH2)3—, PhO(CH2)2—, MeO(CH2)3—, EtO(CH2)2—, (CH3)2N(CH2)2—, CH3S(CH2)2—, CH3S(O)2(CH2)2—, (CH3)3CO(CH2)2—, HO(CH2)2—, AcNH(CH2)2, BocNH(CH2)2, H2N(CH2)2, Ph-, MeO(CH2)2O(CH2)2—, 4-Me-piperazin-1yl-(CH2)2—, 2-imidazol-1-yl-(CH2)2—, MeO(CH2)2O(CH2)2O(CH2)2—, (1-Me-1H-imidazol-2-yl)-S(CH2)2—, (4-Me-thiazol-5-yl)-(CH2)2—, Allyl-, HOCH2CH(OH)CH2—, (Pyridine-2-yl)-(CH2)3—, (Pyridine-3-yl)-(CH2)2—, (Octahydro-quinolizine-1-yl)CH2—, (Pyrrolidin-1-yl)-(CH2)2—, 1-Me-piperidin-4-yl, 2-oxooxazolidin-3-yl, (methylsulfonamido)-(CH2)2—, 3-methylcarboxylate-pyrazin-2-yl, 3-Me-pyrazin-2-yl, CH3S(O)2NH(CH2)2—, (CH3CH2O)2P(O)2NH(CH2)2—, CH3OC(O)NH(CH2)2—, CH3CH2NHC(O)NH(CH2)2— and Morpholin-4-yl-(CH2)2;
- and
- wherein R2 is selected from the group consisting of H and CH3;
- and
- 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, 3-cyanophenyl, thiophen-2-yl, thiophen-3-yl, 4,5-di-bromo-thiophen-2-yl, 5-chloro-thiophen-2-yl, and 5-bromo-thiophen-2-yl.
3 more elements
A compound of Formula (Ib):
- in which:
- R5 is selected from the group consisting of MeO(CH2)2, t-BuOC(O)NHCH2CH2, NH2CH2CH2, MeOCH2CH2, (CH3)3COC(O)CH2, HOC(O)CH2, CH3—, (CH3CH2)2NCH2CH2—, (CH3)2NCH2(CH2)2—, 1,1-dioxo-tetrahydro-1-lambda6-thiophen-3-yl, 4-hydroxy-1,1-dioxo-tetrahydro-1-lambda6-thiophen-3-yl, HOCH2CH(OH)CH2—, N-(1,1-dioxo-tetrahydro-1lambda6-thiophen-3-yl)-acetamide, o-tolyl-, pyridin-2-yl, (3,5-dimethylisoxazol-4-yl)-CH2—, 2,4-dimethoxy-benzyl, 3-(hydroxymethyl)-5-methylisoxazol-4-yl)-CH2—, 2,3,4-trimethoxy-benzyl-, 2,4-dimethoxy-benzyl, HO(CH2)2—, 3-Me-pyrazin-2-yl and (CH3)2NCH2CH2;
- wherein R6 is selected from the group consisting of CH3, MeOCH2CH2, H, and CH2CH3;
- and
- 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, 3-cyanophenyl, thiophen-2-yl, thiophen-3-yl, 4,5-di-bromo-thiophen-2-yl, 5-chloro-thiophen-2-yl, and 5-bromo-thiophen-2-yl.
2 more elements
A compound of Formula (Ic):
- in which:
- is selected from the group consisting of 4-formyl-piperazin-1-yl, 4-methylpiperazin-1-yl-, 4-ethylpiperazin-1-yl-, 4-phenylpiperazin-1-yl-, 4-pyrimidin-2-yl-piperazin-1-yl, hexahydro-pyrrolo[1,2-a]imidazole-1-yl, morpholin-4-yl, 4-hydroxyisoxazolidin-2-yl, and 1,1-dioxo-1-lambda6-thiomorpholin-4-yl
- and 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, 3-cyanophenyl, thiophen-2-yl, thiophen-3-yl, 4,5-di-bromo-thiophen-2-yl, 5-chloro-thiophen-2-yl, and 5-bromo-thiophen-2-yl.
A compound of Formula (Id):
- in which:
- R4 and R4′ are independently selected from the group consisting of H, O, and null;
- wherein Y is selected from the group consisting of N and O;
- and
- wherein R5 and R6 are independently selected from the group consisting of O, OEt, OH, H, Et, CH3, MeO(CH2)2—, and null;
- and
- 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, 3-cyanophenyl, thiophen-2-yl, thiophen-3-yl, 4,5-di-bromo-thiophen-2-yl, 5-chloro-thiophen-2-yl, and 5-bromo-thiophen-2-yl.
4 more elements
A compound of Formula (Ie):
- in which:
- R5 is selected from the group consisting of 4-MeO-Ph, 4-F-Ph, 4-acetamido-Ph, 3,4-dimethoxy-Ph, (Pyrazin-2-yl)-(CH2)2—, 4-methyl-4H-1,2,4-triazol-3-yl, 1,3,4-thiadiazol-2-yl, thiazol-2-yl, 1-methyl-1H-tetrazol-5-yl, and 4,5-dimethyl-4H-1,2,4-triazol-3-yl.
A compound of Formula (If):
- in which:
- Y is selected from the group consisting of N and O;
- and
- wherein R5 is selected from the group consisting of MeO(CH2)2—, 1,1-dioxo-tetrahydro-1-lambda6-thiophen-3-yl, 3,5-Dimethyl-isoxazol-4-ylmethyl-, CH3S(O)2(CH2)2—, and CH3S(O)(CH2)2—;
- and
- wherein R6 is selected from the group consisting of H, CH3, and null when Y is O;
- and
- 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, 3-cyanophenyl, thiophen-2-yl, thiophen-3-yl, 4,5-di-bromo-thiophen-2-yl, 5-chloro-thiophen-2-yl, and 5-bromo-thiophen-2-yl.
5 more elements
A compound selected from the group consisting of:
- 1-(3,4-dichlorobenzyl)-3-(4-(methoxymethyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-methoxyethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-(butoxymethyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-phenoxyethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((3-methoxypropoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-ethoxyethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(dimethylamino)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(methylthio)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(2-methanesulfinyl-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(methylsulfonyl)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(3-fluoro-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-[4-(2-tert-butoxy-ethoxymethyl)-thiazol-2-yl]-3-(3,4-dichloro-benzyl)-urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(2-hydroxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-phenoxymethyl-thiazol-2-yl)-urea;
- 1-(3-fluoro-benzyl)-3-[4-(2-methanesulfonyl-ethoxymethyl)-thiazol-2-yl]-urea;
- 5-{2-[3-(3,4-dichloro-benzyl)-ureido]-thiazol-4-yl}-pyrrolidin-3-yl ester-urea;
- Ethyl 2-(2-(3-(3,4-dichlorobenzyl)ureido)thiazol-4-yl)acetate-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-(2-hydroxyethyl)thiazol-2-yl)urea;
- 1-(3-fluorobenzyl)-3-(4-(2-hydroxyethyl)thiazol-2-yl)urea;
- Ethyl 2-(3-(3,4-dichlorobenzyl)ureido)thiazole-4-carboxylate-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-(hydroxymethyl)thiazol-2-yl)urea;
- 1-(3-bromo-benzyl)-3-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3-chloro-benzyl)-3-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3-fluoro-benzyl)-3-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3-chloro-4-fluoro-benzyl)-3-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3,4-dimethyl-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3-bromo-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(4-chloro-3-trifluoromethyl-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-benzo[1,3]dioxol-5-ylmethyl-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3-chloro-4-fluoro-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3-chloro-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3-iodo-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(4-bromobenzyl)-3-(4-((2-methoxyethoxy)methyl)thiazol-2-yl)urea;
- 1-(1-(4-bromophenyl)ethyl)-3-(4-((2-methoxyethoxy)methyl)thiazol-2-yl)urea;
- 1-(4-chloro-3-fluoro-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3-bromo-4-chloro-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3,5-difluoro-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-3-(3,4,5-trifluoro-benzyl)-urea;
- 1-(4,5-dibromo-thiophen-2-ylmethyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3-chloro-5-fluoro-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-3-thiophen-3-ylmethyl-urea;
- 1-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-3-thiophen-2-ylmethyl-urea;
- 1-(5-bromo-thiophen-2-ylmethyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(5-chloro-thiophen-2-ylmethyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(4-fluoro-benzyl)-3-[4-(2-methoxy-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3-chloro-benzyl)-3-[4-(2-methanesulfonyl-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3-bromo-benzyl)-3-[4-(2-methanesulfonyl-ethoxymethyl)-thiazol-2-yl]-urea;
- tert-butyl 2-((2-(3-(3,4-dichlorobenzyl)ureido)thiazol-4-yl)methoxy)-ethylcarbamate;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-aminoethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(2-morpholin-4-yl-ethoxymethyl)-thiazol-2-yl]-urea;
- N-(2-{2-[3-(3,4-dichloro-benzyl)-ureido]-thiazol-4-ylmethoxy}-ethyl)-acetamide;
- 1-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(4-((2-(methylthio)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(4-((2-(methylsulfoxyl)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(4-((2-(methylsulfone)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(2-methoxyethoxy)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(4-methylpiperazin-1-yl)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(2-imidazol-1-yl-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(2-(2-methoxyethoxy)ethoxy)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-{4-[2-(1-methyl-1H-imidazol-2-ylsulfanyl)-ethoxymethyl]-thiazol-2-yl}-urea;
- 1-(3,4-dichloro-benzyl)-3-{4-[2-(4-methyl-thiazol-5-yl)-ethoxymethyl]-thiazol-2-yl}-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-(allyloxymethyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2,3-dihydroxypropoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(3-pyridin-2-yl-propoxymethyl)-thiazol-2-yl]-urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(2-pyridin-3-yl-ethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(octahydro-quinolizin-1-ylmethoxymethyl)-thiazol-2-yl]-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(pyrrolidin-1-yl)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(1-methyl-piperidin-4-yloxymethyl)-thiazol-2-yl]-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(2-oxooxazolidin-3-yl)ethoxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(methylsulfonamido)ethoxy)methyl)thiazol-2-yl)urea;
- methyl 3-((2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)methoxy)pyrazine-2-carboxylate-urea;
- 1-(3-fluorobenzyl)-3-(4-((3-methylpyrazin-2-yloxy)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(4-formyl-piperazin-1-ylmethyl)-thiazol-2-yl]-urea;
- [2-({2-[3-(3,4-dichloro-benzyl)-ureido]-thiazol-4-ylmethyl}-methyl-amino)-ethyl]-carbamic acid tert-butyl ester-urea;
- 1-(4-{[(2-amino-ethyl)-methyl-amino]-methyl}-thiazol-2-yl)-3-(3,4-dichloro-benzyl)-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((4-methylpiperazin-1-yl)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((4-ethylpiperazin-1-yl)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((4-phenylpiperazin-1-yl)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-thiazol-2-yl]-urea;
- 1-(4-{[bis-(2-methoxy-ethyl)-amino]-methyl}-thiazol-2-yl)-3-(3,4-dichloro-benzyl)-urea;
- ({2-[3-(3,4-dichloro-benzyl)-ureido]-thiazol-4-ylmethyl}-methyl-amino)-acetic acid tert-butyl ester-urea;
- ({2-[3-(3,4-dichloro-benzyl)-ureido]-thiazol-4-ylmethyl}-methyl-amino)-acetic acid;
- 1-(3,4-dichloro-benzyl)-3-[4-(hexahydro-pyrrolo[1,2-a]imidazol-1-ylmethyl)-thiazol-2-yl]-urea;
- 1-(3,4-dichloro-benzyl)-3-{4-[(2-methoxy-ethylamino)-methyl]-thiazol-2-yl}-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-morpholin-4-ylmethyl-thiazol-2-yl)-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-{[ethyl-(2-methoxy-ethyl)-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((dimethylamino)methyl)thiazol-2-yl)urea;
- 1-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(4-(((2-methoxyethyl)(methyl)amino)methyl)thiazol-2-yl)urea;
- 1-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(4-(((2-(dimethylamino)ethyl)(methyl)amino)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-(4-{[(2-diethylamino-ethyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-{[(3-dimethylamino-propyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-{[(1,1-dioxo-tetrahydro-1-lambda6-thiophen-3-yl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-{[(4-hydroxy-1,1-dioxo-tetrahydro-1-lambda6-thiophen-3-yl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3,4-dichloro-benzyl)-3-{4-[(4-hydroxy-1,1-dioxo-tetrahydro-1-lambda6-thiophen-3-ylamino)-methyl]-thiazol-2-yl}-urea;
- 1-(4-{[(1,1-Dioxo-tetrahydro-1lambda6-thiophen-3-yl)-methyl-amino]-methyl}-thiazol-2-yl)-3-(3-fluoro-benzyl)-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-{[(2,3-dihydroxy-propyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((4-hydroxyisoxazolidin-2-yl)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-[4-(1,1-dioxo-1-lambda6-thiomorpholin-4-ylmethyl)-thiazol-2-yl]-urea;
- 2-({2-[3-(3,4-dichloro-benzyl)-ureido]-thiazol-4-ylmethyl}-methyl-amino)-N-(1,1-dioxo-tetrahydro-1lambda6-thiophen-3-yl)-acetamide;
- 1-(3-fluoro-benzyl)-3-{4-[(methyl-o-tolyl-amino)-methyl]-thiazol-2-yl}-urea;
- 1-(3-fluoro-benzyl)-3-{4-[(methyl-pyridin-2-yl-amino)-methyl]-thiazol-2-yl}-urea;
- 1-(3,4-dichloro-benzyl)-3-(4-methylaminomethyl-thiazol-2-yl)-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((((3,5-dimethylisoxazol-4-yl)methyl)(methyl)amino)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-(4-{[(2,4-dimethoxy-benzyl)-methyl-amino]-methyl}-thiazol-2-yl)-urea;
- 1-(3-fluorobenzyl)-3-(4-((((3-(hydroxymethyl)-5-methylisoxazol-4-yl)methyl)(methyl)amino)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-{4-[(2,3,4-trimethoxy-benzylamino)-methyl]-thiazol-2-yl}-urea;
- 1-(3,4-dichloro-benzyl)-3-{4-[(2,4-dimethoxy-benzylamino)-methyl]-thiazol-2-yl}-urea;
- 1-(3,4-dichloro-benzyl)-3-{4-[(2-hydroxy-ethylamino)-methyl]-thiazol-2-yl}-urea;
- 2-(3-(3,4-dichlorobenzyl)ureido)-N-(2-methoxyethyl)-N-methylthiazole-4-carboxamide;
- 1-(3-fluorobenzyl)-3-(4-((methyl(3-methylpyrazin-2-yl)amino)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(methylsulfonamido)ethoxy)methyl)thiazol-2-yl)urea;
- Diethyl 2-((2-(3-(3,4-dichlorobenzyl)ureido)thiazol-4-yl)methoxy)ethylphosphor-amidate;
- (2-{2-[3-(3,4-dichloro-benzyl)-ureido]-thiazol-4-ylmethoxy}-ethyl)-carbamic acid methyl ester;
- 1-(3,4-dichloro-benzyl)-3-{4-[2-(3-ethyl-ureido)-ethoxymethyl]-thiazol-2-yl}-urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((4-methoxyphenylthio)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((4-fluorophenylthio)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((4-acetamidophenylthio)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((3,4-dimethoxyphenylthio)methyl)-thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((2-(pyrazin-2-yl)ethylthio)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((4-methyl-4H-1,2,4-triazol-3-ylthio)methyl)thiazol-2-yl)urea;
- 1-(4-((1,3,4-thiadiazol-2-ylthio)methyl)thiazol-2-yl)-3-(3,4-dichlorobenzyl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((thiazol-2-ylthio)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((1-methyl-1H-tetrazol-5-ylthio)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichlorobenzyl)-3-(4-((4,5-dimethyl-4H-1,2,4-triazol-3-ylthio)methyl)thiazol-2-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-(3-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-[1,2,4]thiadiazol-5-yl)-urea;
- 1-(3-fluoro-benzyl)-3-(3-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-[1,2,4]thiadiazol-5-yl)-urea;
- 1-(3-fluorobenzyl)-3-(3-((2-methoxyethoxy)methyl)-1,2,4-thiadiazol-5-yl)urea;
- 1-(3,4-dichloro-benzyl)-3-[3-(2-methoxy-ethoxymethyl)-[1,2,4]thiadiazol-5-yl]-urea;
- 1-(3,4-dichloro-benzyl)-3-(3-{[(1,1-dioxo-tetrahydro-1l6-thiophen-3-yl)-methyl-amino]-methyl}-[1,2,4]thiadiazol-5-yl)-urea;
- 1-(3-{[(1,1-dioxo-tetrahydro-1l6-thiophen-3-yl)-methyl-amino]-methyl}-[1,2,4]thiadiazol-5-yl)-3-(3-fluoro-benzyl)-urea;
- 1-(3-{[(3,5-dimethyl-isoxazol-4-ylmethyl)-methyl-amino]-methyl}-[1,2,4]thiadiazol-5-yl)-3-(3-fluoro-benzyl)-urea;
- 1-(3-fluorobenzyl)-3-(3-((2-(methylsulfonyl)ethoxy)methyl)-1,2,4-thiadiazol-5-yl)urea;
- 1-(3-fluorobenzyl)-3-(3-((2-(methylsulfinyl)ethoxy)methyl)-1,2,4-thiadiazol-5-yl)urea;
- and
- 1-(5-Bromo-4-((2-methoxyethoxy)methyl)thiazol-2-yl)-3-(3,4-dichlorobenzyl)urea.
134 more elements
A method to protect a patient from a bacterial infection which comprises administering a therapeutically effective amount of a compound of Formula (I) or a pharmaceutically acceptable salt of a compound of Formula (I) to a patient in need thereof.
Dependencies are inferred from the claim text.