US2017260178A1PendingUtilityA1
Antibacterial compounds

Assignee: SPERO GYRASE INCPriority: Mar 22, 2012Filed: Mar 27, 2017Published: Sep 14, 2017
Est. expiryMar 22, 2032(~5.7 yrs left)· nominal 20-yr term from priority
Inventors:Christopher James Lunniss James T. Palmer Gary Robert William Pitt Lorraine Claire Axford David Davies
A61P 7/00A61P 31/04C07D 417/14C07F 9/65583C07D 417/04A61P 17/00A61P 11/00A61P 15/00
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Claims
Abstract

The present invention provides a compound of the following formula, salts, racemates, diastereomers, enantiomers, esters, carbamates, phosphates, sulfates, deuterated forms and prodrugs thereof. Also provided is the use of these compounds as antibacterials, compositions comprising them and processes for their manufacture.
Claims

exact text as granted — not AI-modified
1 . A compound of Formula (I) 
       
         
           
           
               
               
           
         
         salts, racemates, diastereomers, enantiomers, esters, carbamates, phosphates, sulfates, deuterated forms and prodrugs thereof 
         wherein 
         X 1  is N or C—R 1  where R 1  is selected from H, OH, optionally substituted C 1-3 alkyl, optionally substituted C 2-3 alkenyl, optionally substituted C 2-3 alkynyl, optionally substituted C 1-3 alkoxyl, halo, haloC 1-3 alkyl, NH 2 , optionally substituted NHC 1-3 alkyl, optionally substituted N(C 1-3 alkyl) 2 , optionally substituted SC 1-3 alkyl and CN; 
       
       
         
           
           
               
               
           
         
       
       represents Ring A which is selected from saturated or unsaturated monocyclic C 3-7 cycloalkyl, saturated or unsaturated monocyclic 3-7 membered heterocycle, saturated or unsaturated fused bicyclic C 8-10 cycloalkyl, saturated or unsaturated fused bicyclic 8-10 membered-heterocyclyl, C 6-10 aryl and 5-10 membered heteroaryl and may be optionally substituted;
 Z 1  is a secondary or tertiary alcohol of general formula 
 
       
         
           
           
               
               
           
         
       
       an ester, carbamate, phosphate, sulfate or prodrug thereof as defined below or Z 1  is selected from H, OH, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted (CH 2 ) m OC 1-6 alkyl, optionally substituted (CH 2 ) m SC 1-6 alkyl, optionally substituted (CH 2 ) m S(═O)C 1-6 alkyl, halo, optionally substituted haloC 1-3 alkyl, CN and optionally substituted (CH 2 ) m NR a R b  where each R a  and R b  is independently selected from H, optionally substituted C 1-6 alkyl, optionally substituted C 3-6 cycloalkyl and optionally substituted 4-6-membered heterocycle or R a  and R b  join together to form an optionally substituted 4-6-membered heterocyclyl where each m is an integer independently selected from 0, 1, 2 and 3;
 X 2  is N or C—R 2  where R 2  is selected from H, OH, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted (CH 2 ) m OC 1-6 alkyl, optionally substituted (CH 2 ) m SC 1-6 alkyl, optionally substituted (CH 2 ) m S(═O)C 1-6 alkyl, optionally substituted (CH 2 ) m O(CH 2 ) m C 3-7 cycloalkyl, optionally substituted (CH 2 ) m C 3-7 cycloalkyl, optionally substituted (CH 2 ) m O(CH 2 ) m phenyl, optionally substituted (CH 2 ) m phenyl, optionally substituted (CH 2 ) m O(CH 2 ) m -5-10-membered heterocycle, optionally substituted (CH 2 ) m -5-10-membered heterocycle, halo, optionally substituted haloC 1-3 alkyl, CN, and optionally substituted (CH 2 ) m NR a R b ; 
 X 3  is N or C—R 3  where R 3  is selected from H, OH, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted (CH 2 ) m OC 1-6 alkyl, optionally substituted (CH 2 ) m SC 1-6 alkyl, optionally substituted (CH 2 ) m S(═O)C 1-6 alkyl, optionally substituted (CH 2 ) m O(CH 2 ) m C 3-7 cycloalkyl, optionally substituted (CH 2 ) m C 3-7 cycloalkyl, optionally substituted (CH 2 ) m O(CH 2 ) m phenyl, optionally substituted (CH 2 ) m phenyl, optionally substituted (CH 2 ) m O(CH 2 ) m -5-10-membered heterocycle, optionally substituted (CH 2 ) m -5-10-membered heterocycle, halo, haloC 1-3 alkyl, CN and optionally substituted (CH 2 ) m NR a R b  or R 3  is a group of formula 
 
       
         
           
           
               
               
           
         
       
       where * represents the point of attachment to the carbon ring atom; n is an integer selected from 0, 1, 2 and 3; 
       
         
           
           
               
               
           
         
       
       represents Ring B which is selected from saturated or unsaturated monocyclic C 3-7 cycloalkyl, saturated or unsaturated monocyclic 3-7 membered heterocycle, saturated or unsaturated fused bicyclic C 8-10 cycloalkyl, saturated or unsaturated fused bicyclic 8-10 membered-heterocyclyl, C 6-10 aryl and 5-10 membered heteroaryl and may be optionally substituted; and
 Z 2  is a secondary or tertiary alcohol of general formula 
 
       
         
           
           
               
               
           
         
       
       an ester, carbamate, phosphate, sulfate or prodrug thereof as defined below or Z 2  is selected from H, OH, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, (CH 2 ) m OC 1-6 alkyl, optionally substituted (CH 2 ) m SC 1-6 alkyl, optionally substituted (C 2 ) m S(═O)C 1-6 alkyl, halo, optionally substituted haloC 1-3 alkyl, CN, optionally substituted (CH 2 ) m NR a R b , optionally substituted (CH 2 ) p -4-6-membered heterocycylic ring, optionally substituted (CH 2 ) p -spiro-bicyclic-7-11-membered heterocycylic ring and optionally substituted 
       
         
           
           
               
               
           
         
       
       where p is an integer selected from 0, 1, 2 and 3 and 
       
         
           
           
               
               
           
         
       
       represents an optionally substituted 4-6 membered heterocyclic ring or an optionally substituted spiro bicyclic 7-11-membered heterocyclic ring; and
 Alk is optionally substituted C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl; and 
 with the proviso that Z 1  or Z 2  is a secondary or tertiary alcohol of general formula 
 
       
         
           
           
               
               
           
         
       
       an ester, carbamate, phosphate, sulfate or prodrug thereof wherein q is an integer selected from 0, 1, 2 and 3;
 R 4  is H or is selected from optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted (CH 2 ) t OC 1-6 alkyl, optionally substituted (CH 2 ) t OC(═O)C 1-6 alkyl, optionally substituted (CH 2 ) t SC 1-6 alkyl, optionally substituted (CH 2 ) t S(═O)C 1-6 alkyl, halo, optionally substituted haloC 1-3 alkyl and optionally substituted (CH 2 ) t NR a R b ; 
 R 5  is selected from optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted C 3-7 cycloalkyl ring, optionally substituted phenyl, optionally substituted 4-6-membered heterocyclyl ring, optionally substituted 5-6-membered heteroaryl ring, optionally substituted (CH 2 ) t OC 1-6 alkyl, optionally substituted (CH 2 ) t OC(═O)C 1-6 alkyl, optionally substituted (CH 2 ) t SC 1-6 alkyl, optionally substituted (CH 2 ) t S(═O)C 1-6 alkyl, halo, optionally substituted haloC 1-3 alkyl and optionally substituted (CH 2 ) m NR a R b ; 
 t is an integer selected from 1, 2, 3, 4, 5 and 6; 
 or R 4  and R 5  together with the carbon atom to which they are attached form an optionally substituted 4-6-membered heterocyclic ring or C 3-7 cycloalkyl ring; and 
 * represents the point of attachment to Ring A or Ring B respectively; and further wherein each (CH 2 ) entity when present may be independently optionally substituted. 
 
     
     
         2 . A compound according to  claim 1  wherein Z 1  is a secondary or tertiary alcohol of general formula 
       
         
           
           
               
               
           
         
       
       or an ester, carbamate, phosphate, sulfate or prodrug thereof wherein q, R 4 , R 5  and * are as defined in  claim 1 . 
     
     
         3 . A compound according to  claim 1  or  claim 2  wherein Z 1  is a chiral alcohol of general formula 
       
         
           
           
               
               
           
         
         or an ester, carbamate, phosphate, sulfate or prodrug thereof wherein q, R 4 , R 5  and * are as defined in  claim 1  provided that R 4  and R 5  are different. 
       
     
     
         4 . A compound according to any one of  claims 1  to  3  wherein X 1  is C—R 1 , X 2  is C—R 2  and X 3  is C—R 3 . 
     
     
         5 . A compound according to any one of  claims 1  to  4  wherein ring A is an optionally substituted 5-6-membered heteroaryl. 
     
     
         6 . A compound according to any one of  claims 1  to  5  wherein X 1  is C—R 1  and R 1  is H or halo. 
     
     
         7 . A compound according to any one of  claims 1  to  6  wherein X 2  is C—R 2  where R 2  is selected from H, OH, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted OC 1-6 alkyl, optionally substituted SC 1-6 alkyl, optionally substituted S(═O)C 1-6 alkyl, an optionally substituted 5-6-membered heterocycle, halo, haloC 1-3 alkyl, CN and optionally substituted (CH 2 ) m NR a R b . 
     
     
         8 . A compound according to any one of  claims 1  to  7  wherein X 3  is C—R 3  and R 3  is H. 
     
     
         9 . A compound according to any one of  claims 1  to  7  wherein X 3  is C—R 3  and R 3  is selected from optionally substituted C 1-3 alkyl, optionally substituted OC 1-3 alkyl, optionally substituted (CH 2 ) m NH 2 , optionally substituted (CH 2 ) m NHC 1-3 alkyl and optionally substituted (CH 2 ) m N(C 1-3 alkyl) 2  where m is as defined in  claim 1 . 
     
     
         10 . A compound according to any one of  claims 1  to  7  wherein X 3  is C—R 3  and R 3  is a group of formula 
       
         
           
           
               
               
           
         
       
       as defined in  claim 1 . 
     
     
         11 . A compound according to  claim 10  wherein the compound is of Formula (II): 
       
         
           
           
               
               
           
         
         salts, racemates, diastereomers, enantiomers, esters, carbamates, phosphates, sulfates, deuterated forms and prodrugs thereof 
         wherein X 1 , X 2 , Alk, Ring A, Ring B, Z 2 , R 4 , R 5  and q are as defined in  claim 1 . 
       
     
     
         12 . A compound according to any one of  claims 1  to  11  wherein ring B is an optionally substituted 5-6 membered heteroaryl. 
     
     
         13 . A compound according to any one of  claims 1  to  12  wherein Z 2  is H. 
     
     
         14 . A compound according to any one of  claims 1  to  12  wherein Z 2  is selected from OH, optionally substituted C 1-6 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted (CH 2 ) m OC 1-6 alkyl, optionally substituted (CH 2 ) m SC 1-6 alkyl, optionally substituted (CH 2 ) m S(═O)C 1-6 alkyl, halo, optionally substituted haloC 1-3 alkyl, (CH 2 ) m NH 2 , optionally substituted (CH 2 ) m NHC 1-6 alkyl, optionally substituted (CH 2 ) m N(C 1-6 alkyl) 2 , optionally substituted (CH 2 ) p -4-6-membered heterocyclic ring, optionally substituted (CH 2 ) p -spiro-bicyclic-7-11-membered heterocyclic ring and optionally substituted 
       
         
           
           
               
               
           
         
       
     
     
         15 . A compound according to  claim 1  wherein the compound is of general formula (III): 
       
         
           
           
               
               
           
         
         salts, racemates, diastereomers, enantiomers, esters, carbamates, phosphates, sulfates, deuterated forms and prodrugs thereof 
         wherein X 1 , X 2 , Alk, R 4 , R 5  and q are as defined in  claim 1 ; 
         X 4  is N, CH, C-halo or C—C 1-3 alkoxy; 
         X 5 , X 6 , X 7  and X 8  are each independently selected from N, C—H or C—Z 2  where Z 2  is as defined in  claim 1  provided that no more than one of X 5 , X 6 , X 7  or X 8  is N. 
       
     
     
         16 . A compound according to any one of  claims 1  to  15  wherein q is 0. 
     
     
         17 . A compound according to  claim 1  selected from the group consisting of:
 1) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 2) 1-ethyl-3-[7-[4-[(3-hydroxy-3-methyl-azetidin-1-yl)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 3) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-6-(tetrahydrofuran-2-ylmethoxy)-1,3-benzothiazol-2-yl]urea; 
 4) 1-ethyl-3-[6-fluoro-5-[6-[hydroxy(3-pyridyl)methyl]-3-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 5) 1-(2-hydroxyethyl)-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 6) 1-ethyl-3-[5-[5-(1-hydroxyethyl)pyrazin-2-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 7) 1-[5-[2-[(1S*,2R*)-1,2-dihydroxypropyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea (mixture 1-[5-[2-[(1S,2R)-1,2-dihydroxypropyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea; and 1-[5-[2-[(1R,2S)-1,2-dihydroxypropyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea); 
 8) 1-[5-[2-[(3R*,4S*)-3,4-dihydroxytetrahydropyran-4-yl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea (mixture 1-[5-[2-[(3R,4S)-3,4-dihydroxytetrahydropyran-4-yl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea; and 1-[5-[2-[(3S,4R)-3,4-dihydroxytetrahydropyran-4-yl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea); 
 9) 1-ethyl-3-[5-[4-(1-hydroxyethyl)triazol-1-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 10) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-pyrimidin-2-yl-1,3-benzothiazol-2-yl]urea; 
 11) 1-ethyl-3-[5-[4-(1-hydroxy-1-methyl-ethyl)imidazol-1-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 12) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-methoxy-1,3-benzothiazol-2-yl]urea; 
 13) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(methoxymethyl)-1,3-benzothiazol-2-yl]urea; 
 14) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[(6-methyl-3-pyridyl)methoxy]-1,3-benzothiazol-2-yl]urea; 
 15) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-(methylsulfanylmethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 16) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-(methylsulfinylmethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 17) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 18) 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl 4-methylpiperazine-1-carboxylate; 
 19) 4-[1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethoxy]-4-oxo-butanoic acid; 
 20) O4-[1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] O1-methyl butanedioate; 
 21) 4-[1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethoxy]-4-oxo-butanoic acid; 
 22) 1-ethyl-3-[5-[2-[(1R)-1-hydroxyethyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 23) 1-ethyl-3-[5-[2-[(1S)-1-hydroxyethyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 24) 1-ethyl-3-[5-[6-[hydroxy-(1-methylimidazol-2-yl)methyl]-3-pyridyl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 25) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[5-(morpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 26) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(pyrrolidin-1-ylmethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 27) 1-ethyl-3-[5-[6-(1-hydroxy-1-methyl-ethyl)-3-pyridyl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 28) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(morpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 29) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[(3-hydroxypyrrolidin-1-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 30) 1-ethyl-3-[7-[4-[(3-hydroxyazetidin-1-yl)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 31) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[(3-methoxyazetidin-1-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 32) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(2-morpholinoethoxy)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 33) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(1-morpholinoethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 34) 1-[7-[4-[(3,3-difluoropyrrolidin-1-yl)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 35) 1-ethyl-3-[7-[4-[[(3S)-3-fluoropyrrolidin-1-yl]methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 36) 1-ethyl-3-[7-[4-[[(3R)-3-fluoropyrrolidin-1-yl]methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 37) 1-[7-[4-[(3,3-difluoro-1-piperidyl)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 38) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(3-morpholinopropoxy)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 39) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-pyrazin-2-yl-1,3-benzothiazol-2-yl]urea; 
 40) 1-[5-[2-(1,2-dihydroxyethyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 41) 1-[7-(dimethylaminomethyl)-6-hydroxy-5-[6-(1-hydroxy-1-methyl-ethyl)-3-pyridyl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 42) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[[(3R)-3-methoxypyrrolidin-1-yl]methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 43) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(6-methylpyrimidin-4-yl)-1,3-benzothiazol-2-yl]urea; 
 44) 1-ethyl-3-[6-hydroxy-5-[6-(1-hydroxy-1-methyl-ethyl)-3-pyridyl]-7-(morpholinomethyl)-1,3-benzothiazol-2-yl]urea; 
 45) 1-[6-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]-3-pyridyl]-4-methyl-piperidine-4-carboxylic acid; 
 46) 2-[6-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]-3-pyridyl]acetic acid; 
 47) 1-ethyl-3-[5-[2-(1-hydroxycyclohexyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 48) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)thiazol-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 49) 1-ethyl-3-[5-[5-(1-hydroxy-1-methyl-ethyl)pyrazin-2-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 50) 1-[2-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]-4-pyridyl]-4-methyl-piperidine-4-carboxylic acid; 
 51) 1-[6-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]-2-pyridyl]-4-methyl-piperidine-4-carboxylic acid; 
 52) 1-[4-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid; 
 53) 1-[7-[4-[(cyclopropylamino)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 54) 4-[[2-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]-4-pyridyl]amino]-1-methyl-cyclohexanecarboxylic acid; 
 55) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-(morpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 56) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[5-(2-morpholinoethoxy)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 57) 1-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-propyl-urea; 
 58) 1-[5-[2-[cyclopropyl(hydroxy)methyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 59) 1-ethyl-3-[5-[2-(1-hydroxypropyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 60) 1-ethyl-3-[5-[2-(1-hydroxy-2,2-dimethyl-propyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 61) 1-ethyl-3-[5-[2-(1-hydroxybutyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea 
 62) [(1R)-1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl] (2R)-2-amino-3-methyl-butanoate; 
 63) [(1S)-1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl] (2R)-2-amino-3-methyl-butanoate; 
 64) 1-ethyl-3-[7-[4-[[(3S)-3-fluoropyrrolidin-1-yl]methyl]-2-pyridyl]-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 65) 1-ethyl-3-[7-[4-[(3-hydroxyazetidin-1-yl)methyl]-2-pyridyl]-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 66) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-[(3-hydroxy-3-methyl-azetidin-1-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 67) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[(3-hydroxy-3-methyl-pyrrolidin-1-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 68) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-[(3-methylmorpholin-4-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 69) 1-[7-[4-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-2-pyridyl]-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 70) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-[(2,2,3,3,5,5,6,6-octadeuteriomorpholin-4-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 71) 1-[7-[4-[(2,5-dimethylmorpholin-4-yl)methyl]-2-pyridyl]-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 72) (2S)-1-[[2-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]-4-pyridyl]methyl]pyrrolidine-2-carboxylic acid; 
 73) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-(6-oxa-2-azaspiro[3.3]heptan-2-ylmethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 74) 1-[5-[2-(ethylcarbamoylamino)-7-[4-(1-hydroxy-1-methyl-ethyl)-2-pyridyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid; 
 75) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-(2-morpholinoethoxy)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 76) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-[(3-methoxyazetidin-1-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 77) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-[[(3R)-3-hydroxypyrrolidin-1-yl]methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 78) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(2-methoxyethylamino)pyrimidin-2-yl]-1,3-benzothiazol-2-yl]urea; 
 79) 1-ethyl-3-[7-[4-(4-ethylpiperazin-1-yl)pyrimidin-2-yl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 80) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(2-methoxyethoxy)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 81) 1-ethyl-3-[5-[2-(1-hydroxy-2-morpholino-ethyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 82) 1-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-methyl-urea; 
 83) 1-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-methyl-urea; 
 84) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-[(3-hydroxy-3-methyl-pyrrolidin-1-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 85) 1-ethyl-3-[7-[4-(2-hydroxyethylamino)pyrimidin-2-yl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 86) 1-ethyl-3-[7-[4-(3-hydroxy-3-methyl-azetidin-1-yl)pyrimidin-2-yl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 87) 1-[6-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]pyrimidin-4-yl]-4-methyl-piperidine-4-carboxylic acid; 
 88) 1-[5-[2-(ethylcarbamoylamino)-7-[4-(1-hydroxyethyl)-2-pyridyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid; 
 89) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 4-methylpiperazine-1-carboxylate; 
 90) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-(4-hydroxy-2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 91) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(2-morpholinoethylamino)pyrimidin-2-yl]-1,3-benzothiazol-2-yl]urea; 
 92) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-(2-methoxyethoxy)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 93) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-(3-methoxyazetidin-1-yl)pyrimidin-2-yl]-1,3-benzothiazol-2-yl]urea; 
 94) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-(4-morpholinopyrimidin-2-yl)-1,3-benzothiazol-2-yl]urea; 
 95) 1-ethyl-3-[5-[6-(1-hydroxyethyl)-3-pyridyl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 96) 1-ethyl-3-[7-(2-pyridyl)-5-[6-(2,2,2-trifluoro-1-hydroxy-ethyl)-3-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 97) 1-[2-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]pyrimidin-4-yl]-4-methyl-piperidine-4-carboxylic acid; 
 98) 1-ethyl-3-[5-[2-(1-ethyl-1-hydroxy-propyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 99) 1-[5-[2-(ethylcarbamoylamino)-7-[5-(1-hydroxy-1-methyl-ethyl)-2-pyridyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid; 
 100) 1-[7-[4-(diethoxyphosphorylmethyl)-2-pyridyl]-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 101) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(morpholinomethyl)pyrimidin-2-yl]-1,3-benzothiazol-2-yl]urea; 
 102) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[6-(morpholinomethyl)pyrazin-2-yl]-1,3-benzothiazol-2-yl]urea; 
 103) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[(2-hydroxy-2-methyl-propyl)amino]pyrimidin-2-yl]-1,3-benzothiazol-2-yl]urea; 
 104) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-(tetrahydrofuran-2-ylmethoxy)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 105) 1-ethyl-3-[7-[4-(3-hydroxyazetidin-1-yl)pyrimidin-2-yl]-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 106) 1-ethyl-3-[7-(5-fluoro-4-morpholino-pyrimidin-2-yl)-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 107) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[4-(2-methoxyethyl)piperazin-1-yl]pyrimidin-2-yl]-1,3-benzothiazol-2-yl]urea; 
 108) 1-ethyl-3-[7-[4-(morpholinomethyl)-2-pyridyl]-5-[6-(2,2,2-trifluoro-1-hydroxy-ethyl)-3-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 109) 1-[6-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]pyrimidin-4-yl]-4-methyl-piperidine-4-carboxylic acid; 
 110) 1-[2-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]-4-pyridyl]piperidine-4-carboxylic acid; 
 111) 1-ethyl-3-[5-[2-(4-hydroxytetrahydropyran-4-yl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 112) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-[4-(2-oxa-7-azaspiro[3.5]nonan-7-ylmethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 113) 1-ethyl-3-[5-[2-(3-hydroxyoxetan-3-yl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 114) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[(3-methoxy-3-methyl-azetidin-1-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 115) 1-ethyl-3-[5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-7-pyrimidin-2-yl-1,3-benzothiazol-2-yl]urea; 
 116) 1-ethyl-3-[7-[4-(2-morpholinoethoxy)-2-pyridyl]-5-[6-(2,2,2-trifluoro-1-hydroxy-ethyl)-3-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 117) 1-[2-[2-(ethylcarbamoylamino)-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-7-yl]pyrimidin-4-yl]-4-methyl-piperidine-4-carboxylic acid; 
 118) 1-[5-[2-[(1R*,2R*)-1,2-dihydroxypropyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea (mixture 1-[5-[2-[(1R,2R)-1,2-dihydroxypropyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea; and 1-[5-[2-[(1S,2S)-1,2-dihydroxypropyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea); 
 119) 1-ethyl-3-[5-[2-(1-hydroxycyclopentyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 120) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[5-(morpholinomethyl)pyrimidin-2-yl]-1,3-benzothiazol-2-yl]urea; 
 121) 1-ethyl-3-[5-[2-[(1R)-1-hydroxyethyl]pyrimidin-5-yl]-7-[4-(morpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 122) 1-ethyl-3-[5-[2-[(1S)-1-hydroxyethyl]pyrimidin-5-yl]-7-[4-(morpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 123) 4-[3-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]oxetan-3-yl]oxy-4-oxo-butanoic acid; 
 124) 4-[2-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-2-hydroxy-propoxy]-4-oxo-butanoic acid; 
 125) 1-ethyl-3-[5-[2-(4-hydroxytetrahydropyran-4-yl)pyrimidin-5-yl]-7-[4-(morpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 126) 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl 2-aminoacetate; 
 127) 1-ethyl-3-[5-[2-(4-hydroxytetrahydrothiopyran-4-yl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 128) 1-ethyl-3-[5-[2-(4-hydroxy-1-methyl-4-piperidyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 129) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 2-(2-aminoethylamino)acetate; 
 130) 1-[5-[2-[(1R*,2S*)-3,3-difluoro-1,2-dihydroxy-propyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea (mixture 1-[5-[2-[(1R,2S)-3,3-difluoro-1,2-dihydroxy-propyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea; and 1-[5-[2-[(1S,2R)-3,3-difluoro-1,2-dihydroxy-propyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea); 
 131) 1-ethyl-3-[7-(2-pyridyl)-5-[2-[(1R*,2S*)-3,3,3-trifluoro-1,2-dihydroxy-propyl]pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea (mixture 1-ethyl-3-[7-(2-pyridyl)-5-[2-[(1R,2S)-3,3,3-trifluoro-1,2-dihydroxy-propyl]pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; and 1-ethyl-3-[7-(2-pyridyl)-5-[2-[(1S,2R)-3,3,3-trifluoro-1,2-dihydroxy-propyl]pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea); 
 132) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] (2S)-2-aminopropanoate; 
 133) 4-[(1S)-1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethoxy]-4-oxo-butanoic acid; 
 134) 4-[(1R)-1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethoxy]-4-oxo-butanoic acid; 
 135) 1-[5-[2-(1,2-dihydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(morpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 136) 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl 2-amino-2-methyl-propanoate; 
 137) 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl 3-aminopropanoate; 
 138) tert-butyl 4-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-hydroxy-piperidine-1-carboxylate; 
 139) 1-ethyl-3-[5-[2-(4-hydroxy-1-oxo-thian-4-yl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 140) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 2-(dimethylamino)acetate; 
 141) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-l-methyl-ethyl] 2-morpholinoacetate; 
 142) 1-[7-[4-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-2-pyridyl]-5-[2-[(1R)-1-hydroxyethyl]pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 143) 1-[7-[4-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-2-pyridyl]-5-[2-[(1S)-1-hydroxyethyl]pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 144) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 5-aminopentanoate; 
 145) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 5-(dimethylamino)pentanoate; 
 146) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 2-aminoacetate; 
 147) 1-[7-[4-[(3,3-difluoroazetidin-1-yl)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 148) 1-[7-[4-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-2-pyridyl]-5-[2-(3-hydroxyoxetan-3-yl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 149) 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl dihydrogen phosphate; 
 150) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-6-(2-methoxyethylamino)-1,3-benzothiazol-2-yl]urea; 
 151) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-morpholino-1,3-benzothiazol-2-yl]urea; 
 152) [(1R)-1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl] dihydrogen phosphate; 
 153) [(1S)-1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl] dihydrogen phosphate; 
 154) 1-ethyl-3-[5-[2-(3-hydroxyoxetan-3-yl)pyrimidin-5-yl]-7-[4-(morpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 155) 1-ethyl-3-[7-[4-[(3-methoxyazetidin-1-yl)methyl]-2-pyridyl]-5-[6-[2,2,2-trifluoro-1-hydroxy-ethyl]-3-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 156) 1-[7-[4-[(4,4-difluoro-1-piperidyl)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 157) 1-[5-[2-[1,2-dihydroxy-1-methyl-ethyl]pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 158) 1-ethyl-3-[5-[2-[1-hydroxyethyl]pyrimidin-5-yl]-7-(5-methyl-2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 159) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[(4-methylpiperazin-1-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 160) [(1S)-1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl] (2S)-pyrrolidine-2-carboxylate; 
 161) [(1R)-1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]ethyl] (2S)-pyrrolidine-2-carboxylate; 
 162) tert-butyl 3-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-3-hydroxy-azetidine-1-carboxylate; 
 163) 1-ethyl-3-[5-[2-(3-hydroxyazetidin-3-yl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 164) 1-[7-[4-1[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 165) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 2-[[(2S)-pyrrolidine-2-carbonyl]amino]acetate; 
 166) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] (2S)-pyrrolidine-2-carboxylate; 
 167) 4-[3-[5-[7-[4-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-2-pyridyl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]oxetan-3-yl]oxy-4-oxo-butanoic acid; 
 168) 1-ethyl-3-[7-[5-(1-hydroxyethyl)-2-pyridyl]-5-[2-(1-hydroxyethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 169) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 2-(2-morpholinoethylamino)acetate; 
 170) 2-[[2-[1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethoxy]-2-oxo-ethyl]amino]acetic acid; 
 171) (2S)-2-amino-4-[1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethoxy]-4-oxo-butanoic acid; 
 172) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 4-aminobutanoate; 
 173) 1-ethyl-3-[5-[2-(4-hydroxy-1,1-dioxo-thian-4-yl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 174) 1-ethyl-3-[5-[2-(4-hydroxy-4-piperidyl)pyrimidin-5-yl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 175) 1-[7-[4-[(3-ethoxyazetidin-1-yl)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 176) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-6-methoxy-1,3-benzothiazol-2-yl]urea; 
 177) 1-ethyl-3-[6-fluoro-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 178) 1-ethyl-3-[7-(3-fluoro-4-methoxy-2-pyridyl)-5-[2-[1-hydroxyethyl]pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 179) 3-[[2-[1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethoxy]-2-oxo-ethyl]amino]propanoic acid; 
 180) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] (3R)-pyrrolidine-3-carboxylate; 
 181) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] (3R)-morpholine-3-carboxylate; 
 182) 1-[6-(cyclopropylmethoxy)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 183) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-6-(2-methoxyethoxy)-1,3-benzothiazol-2-yl]urea; 
 184) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] 2-(2-phosphonooxyethylamino)acetate; 
 185) 1-ethyl-3-[5-[2-[1-hydroxyethyl]pyrimidin-5-yl]-7-[4-(thiomorpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 186) 1-ethyl-3-[6-(2-hydroxyethoxy)-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 187) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-(thiomorpholinomethyl)-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 188) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[(1-oxo-1,4-thiazinan-4-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 189) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-6-[2-methoxyethyl(methyl)amino]-1,3-benzothiazol-2-yl]urea; 
 190) [1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-1-methyl-ethyl] dihydrogen phosphate; 
 191) 1-[7-[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 192) 1-[6-[(3,4-dimethoxyphenyl)methoxy]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 193) 1-ethyl-3-[5-[2-[1-hydroxyethyl]pyrimidin-5-yl]-6-(tetrahydrofuran-2-ylmethoxy)-1,3-benzothiazol-2-yl]urea; 
 194) 1-ethyl-3-[5-[2-[1-hydroxyethyl]pyrimidin-5-yl]-6-morpholino-1,3-benzothiazol-2-yl]urea; 
 195) 1-[7-[(3S)-3-aminopyrrolidin-1-yl]-5-[2-(l-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]-3-ethyl-urea; 
 196) 1-ethyl-3-[7-[4-[(2-hydroxyethylamino)methyl]-2-pyridyl]-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-1,3-benzothiazol-2-yl]urea; 
 197) 1-ethyl-3-[5-[5-(1-hydroxyethyl)-3-pyridyl]-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 198) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-[4-[(2,2,3,3,5,5,6,6-octadeuteriomorpholin-4-yl)methyl]-2-pyridyl]-1,3-benzothiazol-2-yl]urea; 
 199) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-6-(2-morpholinoethoxy)-1,3-benzothiazol-2-yl]urea; 
 200) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-6-(2-methoxyethylsulfanyl)-1,3-benzothiazol-2-yl]urea; 
 201) 1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-6-(2-methoxyethylsulfinyl)-1,3-benzothiazol-2-yl]urea; and 
 202) 1-ethyl-3-[5-[2-[(1R)-1-hydroxyethyl]pyrimidin-5-yl]-7-(5-methoxy-2-pyridyl)-1,3-benzothiazol-2-yl]urea; 
 
       salts, racemates, diastereomers, enantiomers, esters, carbamates, phosphates, sulfates, deuterated forms and prodrugs thereof. 
     
     
         18 . A method for the treatment of a bacterial infection comprising administration of a compound as defined in any one of  claims 1  to  17  or a pharmaceutically acceptable salt, racemate, diastereomer, enantiomer, ester, carbamate, phosphate, sulfate, deuterated form or prodrug thereof to a subject suffering from said infection. 
     
     
         19 . A compound as defined in any one of  claims 1  to  17  or a pharmaceutically acceptable salt, racemate, diastereomer, enantiomer, ester, carbamate, phosphate, sulfate, deuterated form or prodrug thereof for use in the treatment of a bacterial infection. 
     
     
         20 . Use of a compound as defined in any one of  claims 1  to  17  or a pharmaceutically acceptable salt, racemate, diastereomer, enantiomer, ester, carbamate, phosphate, sulfate, deuterated form or prodrug thereof in the preparation of a medicament for the treatment of a bacterial infection in a subject. 
     
     
         21 . A method according to  claim 18 , a compound according to  claim 19  or a use according to  claim 20  wherein the bacterial infection is a Gram-positive infection, Gram-negative infection, community acquired bacterial pneumonia (CABP), hospital acquired bacterial pneumonia (HABP), or ventilator acquired bacterial pneumonia (VABP). 
     
     
         22 . A method according to  claim 18 , a compound according to  claim 19  or a use according to  claim 20  wherein the bacterial infection is a respiratory infection, a skin or skin structure infection, a urinary tract infection, an intra-abdominal infection or a blood stream infection. 
     
     
         23 . An antibacterial agent comprising a compound as defined in any one of  claims 1  to  17  or a pharmaceutically acceptable salt, racemate, diastereomer, enantiomer, ester, carbamate, phosphate, sulfate, deuterated form or prodrug thereof. 
     
     
         24 . A pharmaceutical composition comprising a compound as defined in any one of  claims 1  to  17  or a pharmaceutically acceptable salt, racemate, diastereomer, enantiomer, ester, carbamate, phosphate, sulfate, deuterated form or prodrug thereof and an excipient or carrier. 
     
     
         25 . A compound as defined in any one of  claims 1  to  17  or a pharmaceutically acceptable salt, racemate, diastereomer, enantiomer, ester, carbamate, phosphate, sulfate, deuterated form or prodrug thereof for use as a gyrase inhibitor. 
     
     
         26 . A process for the manufacture of a compound as defined in any one of  claims 1  to  17  comprising the step(s) of:
 coupling an intermediate of formula (i-a) with a precursor of formula (ii-a): 
 
       
         
           
           
               
               
           
         
         or alternatively coupling an intermediate of formula (i-b) with a precursor of formula (ii-b): 
       
       
         
           
           
               
               
           
         
         under coupling conditions wherein 
         W 1  and W 2  are selected from halo, boronic acid or a boronate ester thereof, a stannylated moiety and triflate; 
         Y 1  and Y 2  are selected from H, halo, boronic acid or a boronate ester thereof, a stannylated moiety and triflate; and 
         ring A, ring B, Alk, X 1 , X 2 , X 3 , R 4 , R 5  and q are as defined in  claim 1 .
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