US2012059026A1PendingUtilityA1

Antimicrobial agents

Individually held — no corporate assignee on recordPriority: Apr 30, 2009Filed: Apr 30, 2010Published: Mar 8, 2012
Est. expiryApr 30, 2029(~2.8 yrs left)· nominal 20-yr term from priority
C07D 455/03C07D 217/02C07D 217/12C07D 217/10C07D 405/04A61P 31/04
49
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Claims

Abstract

The invention provides a compound of formula (I): or a salt or prodrug thereof, wherein Y, W, Z, Z 1 , Z 2 , Z 3 , Z 4 , and R 1 -R 12 have any of the values described in the specification, as well as compositions comprising a compound of formula (I). The compounds are useful as antibacterial agents.

Claims

exact text as granted — not AI-modified
1 . A compound of formula I: 
       
         
           
           
               
               
           
         
       
       wherein:
 the dashed line between Y and W represents a single or double bond; 
 when Y is —CR 2 —, Z is —(CR 13   2 ) 2 — or —CR 14 ═CR 14 — and R 12  is a bond; W is N or (NR a ) + X − ; 
 when Y is —CR 2 — and Z is absent; W is NR b  or (NR c R d ) + X − ; 
 when Y is —C═, Z is —(CR 13   2 ) 2 — or —CR 14 ═CR 14 — and R 12  is a bond; W is N + X − ; or 
 when Y is —C═and Z is absent; W is N or (NR a ) + X − ; 
 X −  is a pharmaceutically suitable counterion; 
 Z 1 , Z 2 , Z 3  and Z 4  are each independently O, S or NR e ; or R 8 —Z 1 —, R 9 —Z 2 —, R 10 —Z 3 —, and R 11 —Z 4 — can each independently be H, optionally substituted aryl or optionally substituted heteroaryl; 
 R 1  is H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio; and R 2  is H or (C 1 -C 6 )alkyl, wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 1  and R 2  is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 1  and R 2  is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; or R 1  and R 2  together with the carbon to which they are attached form a carbonyl group; 
 at least one of R 3 , R 4 , R 5 , R 6  and R 7  is hydroxyl, carboxy, cyano, alkoxy, CF 3 SO 3 —, alkyl, substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted arylalkyl, optionally substituted heteroarylalkyl, optionally substituted aryl, optionally substituted arylalkanoyl, R k , or optionally substituted heteroaryl, wherein substituted alkyl is an alkyl group with 1 to 5 substituent groups independently selected from cycloalkyl, substituted cycloalkyl, alkoxycarbonyl, cyano, halo, hydroxyl, oxo, carboxy, aryloxy, heteroaryloxy, heterocyclooxy, nitro, sulfo, —S(O) 2 NR n R p , —N(R n )S(O) 2 R p , and —NR n R p , wherein R n  and R p  may be the same or different and are chosen from hydrogen, alkyl, arylalkyl, heteroarylalkyl, cycloalkyl, substituted cycloalkyl, aryl, heteroaryl and heterocyclic; and the remainder of R 3 , R 4 , R 5 , R 6  and R 7  are independently H, halo, nitro, sulfo, —S(O) 2 NR n R p , —N(R n )S(O) 2 R p , —NR h R i  optionally substituted alkyl, optionally substituted arylalkyl, optionally substituted heteroarylalkyl, optionally substituted aryl, or optionally substituted heteroaryl; or R 3  is —Z 13 —R 13  wherein Z 13  is O, S or NR e  and R 13  is (C 1 -C 6 )alkyl, substituted (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g  or R 13  and R 9  together with the atoms to which they are attached form a 5 to 7 membered ring; or R 6  and R 7  together with the atoms to which they are attached form a 5 to 6 membered heterocycle wherein the heterocycle is optionally fused with an optionally substituted aryl. 
 when Z is absent R 12  is H, alkyl, halo, —NR h R i , NO 2 , aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl wherein alkyl, aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl are optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 R 8  and R 9  are each independently, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g  or R 8  and R 9  together with the atoms to which they are attached form a 5 to 7 membered ring; or R 8 —Z 1 — and R 9 —Z 2 — can each independently be H; 
 R 10  and R 11  are each independently, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g  or R 10  and R 11  together with the atoms to which they are attached form a 5 to 7 membered ring; or R 10 —Z 3 —, and R 11 —Z 4 — can each independently be H; 
 each R 13  is independently H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 13  is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 13  is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 each R 14  is independently H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 14  is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 14  is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 R a  is (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 R b  is H or (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 R c  and R d  are each independently selected from (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 each R e  is independently H or (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more halo; 
 R f  and R g  are each independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 ) alkyl or heteroaryl(C 1 -C 6 ) alkyl; or R f  and R g  together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino; 
 R h  and R i  are each independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 ) alkyl or heteroaryl(C 1 -C 6 ) alkyl; or R h  and R i together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino; 
 each R k  is independently selected from an aryl optionally substituted with one or more R m , an alkyl substituted with one or more heterocycle, and an alkyl substituted with one or more substituted heterocycle; 
 each R m  is independently, alkoxy, substituted alkoxy, heteroaryl, heterocycle, or —S(O) 2 NR u R v ; and 
 each R u  and R v  is independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, or heteroaryl(C 1 -C 6 )alkyl; or R m  and R n  together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino; 
 or a salt or prodrug thereof. 
 
     
     
         2 . The compound of  claim 1  wherein:
 the dashed line between Y and W represents a single or double bond; 
 when Y is —CR 2 —, Z is —(CR 13   2 ) 2 — or CR 14 ═CR 14 — and R 12  is a bond; W is N or (NR a ) + X − ; 
 when Y is —CR 2 — and Z is absent; W is NR b  or (NR c R d ) + X − ; 
 when Y is —C═, Z is —(CR 13   2 ) 2 — or —CR 14 ═CR 14 — and R 12  is a bond; W is N + X − ; or 
 when Y is —C═and Z is absent; W is N or (NR a ) + X − ; 
 X −  is a pharmaceutically suitable counterion; 
 Z 1 , Z 2 , Z 3  and Z 4  are each independently O, S or NR e ; 
 R 1  is H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio; and R 2  is H or (C 1 -C 6 )alkyl, wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 1  and R 2  is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 1  and R 2  is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; or R 1  and R 2  together with the carbon to which they are attached form a carbonyl group; 
 at least one of R 3 , R 4 , R 5 , R 6  and R 7  is aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl and the remainder are each independently H, alkyl, halo, —NR h R i , NO 2 , aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl wherein the alkyl, aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl of R 3 , R 4 , R 5 , R 6  and R 7  is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 when Z is absent R 12  is H, alkyl, halo, —NR h R i , NO 2 , aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl wherein alkyl, aryl, heteroaryl, aryl(C 1 -C 6 )alkyl, heteroaryl(C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkanoyl or heteroaryl(C 1 -C 6 )alkanoyl are optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 R 8  and R 9  are each independently, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g  or R 8  and R 9  together with the atoms to which they are attached form a 5 to 7 membered ring; 
 R 10  and R 11  are each independently, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl or —C(═O)NR f R g  or R 10  and R 11  together with the atoms to which they are attached form a 5 to 7 membered ring; 
 each R 13  is independently H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 13  is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i , and wherein any aryloxy, or arylthio of R 13  is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 each R 14  is independently H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, aryloxy or arylthio wherein any (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, and (C 1 -C 6 )alkylthio of R 14  is optionally substituted with one or more groups selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and NR h R i , and wherein any aryloxy, or arylthio of R 14  is optionally substituted with one or more groups selected from halo, cyano, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 R a  is (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 R b  is H or (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (═O), (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 R c  and R d  are each independently selected from (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more groups independently selected from halo, cyano, oxo (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, carboxy, NO 2 , hydroxy, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, and —NR h R i ; 
 each R e  is independently H or (C 1 -C 6 )alkyl wherein (C 1 -C 6 )alkyl is optionally substituted with one or more halo; 
 R f  and R g  are each independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 ) alkyl or heteroaryl(C 1 -C 6 ) alkyl; or R f  and R g  together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino; and 
 R h  and R i  are each independently H, (C 1 -C 6 )alkyl, aryl, heteroaryl, aryl(C 1 -C 6 ) alkyl or heteroaryl(C 1 -C 6 ) alkyl; or R f  and R g  together with the nitrogen to which they are attached form a morpholino, piperazino, pyrrolidino or piperidino; 
 or a pharmaceutically acceptable salt or prodrug thereof. 
 
     
     
         3 . The compound of  claim 1  which is a compound of the following formula: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         4 . The compound of  claim 1  which is a compound of the following formula: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         5 . The compound of  claim 1  which is a compound of the following formula: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         6 . The compound of  claim 1  which is a compound of the following formula: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         7 . The compound of  claim 1  which is a compound of the following formula: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         8 . The compound of  claim 1  which is a compound of the following formula: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         9 . The compound of  claim 1  which is a compound of the following formula: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         10 . The compound of  claim 1  which is a compound of formula Ih: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         11 . The compound of  claim 1  which is a compound of formula Ij: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         12 . The compound of  claim 1  which is a compound of formula Ik: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         13 . The compound of  claim 1  which is a compound of formula Im: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         14 . The compound of  claim 1  which is a compound of formula In: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         15 . The compound of  claim 1  which is a compound of formula Ip: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         16 . The compound of  claim 1  which is a compound of formula Ir: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         17 - 38 . (canceled) 
     
     
         39 . The compound of  claim 1  which is selected from: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       or a salt or prodrug thereof. 
     
     
         40 . The compound of  claim 1  which is selected from: 
       
         
           
           
               
               
           
         
       
       or a prodrug thereof. 
     
     
         41 . The compound of  claim 1  which is selected from: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       or a salt or prodrug thereof. 
     
     
         42 . The compound of  claim 1  which is selected from: 
       
         
           
           
               
               
           
         
       
       or a salt or prodrug thereof. 
     
     
         43 . The compound of  claim 1  which is selected from: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       or a salt or prodrug thereof. 
     
     
         44 . The compound of  claim 1  which is selected from: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       or a salt or prodrug thereof. 
     
     
         45 - 46 . (canceled) 
     
     
         47 . A composition comprising a compound of formula I as described in  claim 1 , or a pharmaceutically acceptable salt or prodrug thereof, and a pharmaceutically acceptable vehicle. 
     
     
         48 . A method for inhibiting FtsZ polymerization in a bacterium comprising contacting the bacterium with an amount of a compound of formula I as described in  claim 1 , or a pharmaceutically acceptable salt or prodrug thereof, effective to inhibit FtsZ polymerization. 
     
     
         49 . A method for inhibiting FtsZ Z-ring formation in a bacterium comprising contacting the bacterium with an amount of a compound of formula I as described in  claim 1 , or a pharmaceutically acceptable salt or prodrug thereof, effective to inhibit FtsZ Z-ring formation. 
     
     
         50 . A method for inhibiting the recruitment of divisome proteins in a bacterium comprising contacting the bacterium with an amount of a compound of formula I as described in  claim 1 , or a pharmaceutically acceptable salt or prodrug thereof, effective to inhibit the recruitment of divisome proteins. 
     
     
         51 . A method for treating a bacterial infection in a mammal comprising administering to the mammal an effective amount of a compound of formula I as described in as described in  claim 1 , or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
         52 - 60 . (canceled)

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