Antibacterial agents

Abstract

Antibacterial compounds of formula (I) are provided: as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

1 . A compound having the following formula (I): 
     
       
         
         
             
             
         
       
     
     or a stereoisomer, pharmaceutically acceptable salt, ester, or prodrug thereof,
 wherein:
 E is selected from the group consisting of:
 (1) H, 
 (2) substituted or unsubstituted C 1 -C 6 -alkyl, 
 (3) substituted or unsubstituted C 2 -C 6 -alkenyl, 
 (4) substituted or unsubstituted C 2 -C 6 -alkynyl, 
 (5) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (6) substituted or unsubstituted aryl, 
 (7) substituted or unsubstituted heterocyclyl, and 
 (8) substituted or unsubstituted heteroaryl; 
 
 L is absent or selected from the group consisting of:
 (1) substituted or unsubstituted C 1 -C 6 -alkyl, 
 (2) —(NR 3L ) 0-1 —(CH 2 ) 0-4 —NR 3L —(CH 2 ) 0-4 —, 
 (3) —(NR 3L ) 0-1 —C(R 1L ,R 2L )—NR 3L —C(R 1L ,R 2L )— 
 (4) —C(R 1L ,R 2L )—O—C(R 1L ,R 2L )—, 
 (5) —(CH 2 ) 0-4 —NR 3L —C(R 1L ,R 2L )—CONH—(CH 2 ) 0-4 —, 
 (6) —CO—C(R 1L ,R 2L )—NHCO—, 
 (7) —CONR 3L —, 
 (8) —NR 3L CO—, 
 (9) —NR 3L —, 
 (10) —SO 2 NR 3L —, 
 (11) —NR 3L —C(═O)—NR 3L —, 
 (12) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (13) substituted or unsubstituted aryl, 
 (14) substituted or unsubstituted heterocyclyl, and 
 (15) substituted or unsubstituted heteroaryl, 
 wherein:
 each R 1L , R 2L , and R 3L  is independently selected from the group consisting of: 
  (a) H, 
  (b) substituted or unsubstituted C 1 -C 6 -alkyl, 
  (c) C 1 -C 6 -alkyl substituted with aryl, 
  (d) C 1 -C 6 -alkyl substituted with heterocyclyl, and 
  (e) C 1 -C 6 -alkyl substituted with heteroaryl, 
 
 or R 1L  and R 3L , together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S; 
 
 D is absent or selected from the group consisting of:
 (1) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (2) substituted or unsubstituted aryl, 
 (3) substituted or unsubstituted heterocyclyl, and 
 (4) substituted or unsubstituted heteroaryl; 
 
 G is selected from the group consisting of:
 (1) —NR 1G C(═O)—, 
 (2) —C(═O)NR 1G —, 
 (3) —(CH 2 ) 0-4 NHCH 2 C(═O)NR 1G —, 
 (4) —CR 2G ═CR 2G —, 
 (5) —S(═O)—, 
 (6) —SO 2 —, 
 (7) —C(R 3G ) 2 —S(═O)—, 
 (8) —S(═O)—C(R 3G ) 2 —, 
 (9) —C(R 3G ) 2 —SO 2 —, 
 (10) —SO 2 —C(R 3G ) 2 — 
 (11) —CR 3G ═CR 3G —CR 3G ═CR 3G —, 
 (12) —C(R 3G ) 2 —, 
 (13) —CR 3G ═CR 3G —C≡C—, 
 (14) —C≡C—CR 3G ═CR 3G —, 
 (15) —C(═O)—C≡C—, 
 (16) —C≡C—C(═O)—, 
 (17) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (18) substituted or unsubstituted aryl, 
 (19) substituted or unsubstituted heterocyclyl, and 
 (20) substituted or unsubstituted heteroaryl, 
 wherein:
 R 1G  is substituted or unsubstituted C 1 -C 6 -alkyl; 
 each R 2G  is independently selected from the group consisting of H, a halogen atom, and substituted or unsubstituted C 1 -C 6 -alkyl, and at least one R 2G  is not H; and 
 R 3G  is selected from the group consisting of H, a halogen atom, and substituted or unsubstituted C 1 -C 6 -alkyl; 
 
 
 Y is absent or selected from the group consisting of:
 (1) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (2) substituted or unsubstituted aryl, 
 (3) substituted or unsubstituted heterocyclyl, and 
 (4) substituted or unsubstituted heteroaryl; 
 
 X is selected from the group consisting of:
 (1) —(C═O)NR 4 —, 
 (2) —C 1 -C 6 -alkyl-(C═O)NR 4 —, 
 (3) —C 2 -C 6 -alkenyl-(C═O)NR 4 —, 
 (4) —C 2 -C 6 -alkynyl-(C═O)NR 4 —, 
 (5) —CH 2 NR 4 —, 
 (6) —SO 2 NR 4 —, 
 (7) —S(═O)NR 4 —, 
 (8) —NR 4 C(═O)—, and 
 (9) —NR 4 —, 
 or X and A, together with the atoms to which they are attached can form a heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S, 
 or when Y is a bicyclic substituted or unsubstituted heterocyclyl or heteroaryl, then X is absent; 
 
 R 3  is H or substituted or unsubstituted C 1 -C 6 -alkyl, or R 3  and A, together with the atom to which they are attached can form a substituted or unsubstituted 3-10 membered cycloalkyl or a heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring are selected from N, O and S; 
 R 4  is (1) H or substituted or unsubstituted C 1 -C 6 -alkyl, or (2) R 4  and A, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S, or (3) R 4  and Y, together with the atoms to which they are attached, form a bicyclic substituted or unsubstituted heterocyclyl or heteroaryl; 
 n is an integer from 0-6; 
 A is selected from the group consisting of:
 (1) H, 
 (2) —(CH 2 ) 0-4 C(R 1a ,R 2a )(CH 2 ) 0-4 OR 3a , 
 (3) —(CH 2 ) 0-4 C(R 1a ,R 2a )N(R 4a ,R 5a ), 
 (4) —(CH 2 ) 0-4 C(R 1a ,R 2a )N(R 4a )COR 3a , 
 (5) —(CH 2 ) 0-4 C(R 1a ,R 2a )NHCON(R 4a ,R 5a ), 
 (6) —(CH 2 ) 0-4 C(R 1a ,R 2a )NHC(═NH)N(R 4a ,R 5a ), 
 (7) —CH(R 1a ,R 2a ), 
 (8) —C≡CH, 
 (9) —(CH 2 ) 0-4 C(R 1a ,R 2a )CN, 
 (10) —(CH 2 ) 0-4 C(R 1a ,R 2a )CO 2 R 3a , 
 (11) —(CH 2 ) 0-4 C(R 1a ,R 2a )CON(R 4a ,R 5a ), 
 (12) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (13) substituted or unsubstituted aryl, 
 (14) substituted or unsubstituted heterocyclyl, and 
 (15) substituted or unsubstituted heteroaryl, 
 wherein:
 each R 1a , R 2a , R 3a , R 4a , and R 5a  is independently selected from the group consisting of: 
  (a) H, 
  (b) a halogen atom, 
  (c) substituted or unsubstituted C 1 -C 6 -alkyl, 
  (d) substituted or unsubstituted aryl, 
  (e) substituted or unsubstituted heterocyclyl, and 
  (f) substituted or unsubstituted heteroaryl, 
 
 or R 4a  and R 5a  together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S; 
 
 Q is absent or selected from the group consisting of:
 (1) —C(═O)N(R 1 ,R 2 ), 
 (2) —NHC(═O)N(R 1 ,R 2 ), 
 (3) —N(OH)C(═O)N(R 1 ,R 2 ), 
 (4) —CH(OH)C(═O)N(R 1 ,R 2 ), 
 (5) —CH[N(R 2q , R 3q )]C(═O)N(R 1 ,R 2 ), 
 (6) —CHR 1q C(═O)N(R 1 , R 2 ), 
 (7) —CO 2 H, 
 (8) —C(═O)NHSO 2 R 4q , 
 (9) —SO 2 NH 2 , 
 (10) —N(OH)C(═O)R 1q , 
 (11) —N(OH)SO 2 R 4q , 
 (12) —NHSO 2 R 4q , 
 (13) —SH, 
 (14) —CH(SH)(CH 2 ) 0-1 C(═O)N(R 1 ,R 2 ), 
 (15) —CH(SH)(CH 2 ) 0-1 CO 2 H, 
 (16) —CH(OH)(CH 2 ) 0-1 CO 2 H, 
 (17) —CH(SH)CH 2 CO 2 R 1q , 
 (18) —CH(OH)(CH 2 )SO 2 NH 2 , 
 (19) —CH(CH 2 SH)NHCOR 1q , 
 (20) —CH(CH 2 SH)NHSO 2 R 4q , 
 (21) —CH(CH 2 SR 5q )CO 2 H, 
 (22) —CH(CH 2 SH)NHSO 2 NH 2 , 
 (23) —CH(CH 2 OH)CO 2 H, 
 (24) —CH(CH 2 OH)NHSO 2 NH 2 , 
 (25) —C(═O)CH 2 CO 2 H, 
 (26) —C(═O)(CH 2 ) 0-1 CONH 2 , 
 (27) —OSO 2 NHR 5q , 
 (28) —SO 2 NHNH 2 , 
 (29) —P(═O)(OH) 2 , 
 
 
 
     
       
         
         
             
             
         
       
       
         
           (33) —N(OH)C(═O)CR 1 R 2 , 
           wherein:
 R 1  is selected from the group consisting of: 
  (1) —H, 
  (2) —OH, 
  (3) —OC 1 -C 6 -alkyl, 
  (4) —N(R 2q , R 3q ), and 
  (5) substituted or unsubstituted C 1 -C 6 -alkyl; 
 R 2  is selected from the group consisting of: 
  (1) H, 
  (2) substituted or unsubstituted C 1 -C 6 -alkyl, 
  (3) substituted or unsubstituted C 2 -C 6 -alkenyl, 
  (4) substituted or unsubstituted C 2 -C 6 -alkenyl, 
  (5) substituted or unsubstituted aryl, 
  (6) substituted or unsubstituted heterocyclyl, and 
  (7) substituted or unsubstituted heteroaryl, 
 or R 1  and R 2 , together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring are selected from N, O and S; and 
 each R 1q , R 2q , R 3q , R 4q , and R 5q  is independently selected from the group consisting of H and C 1 -C 6  alkyl. 
 
         
       
     
   
   
       2 . A compound of  claim 1  wherein G is selected from the group consisting of:
 (1) —CR 3G ═CR 3G —C≡C—, and   (2) —C≡C—CR 3G ═CR 3G —.   
   
   
       3 . A compound of  claim 2  wherein G is selected from the group consisting of:
 (1) —CH═CH—C≡C—, and   (2) —C≡C—CH≡CH—.   
   
   
       4 - 6 . (canceled) 
   
   
       7 . A compound of  claim 3  wherein G has the following structure: 
     
       
         
         
             
             
         
       
     
   
   
       8 . (canceled) 
   
   
       9 . A compound of  claim 3  wherein G has the following structure: 
     
       
         
         
             
             
         
       
     
   
   
       10 . A compound of  claim 1  wherein X is —(C═O)NR 4 —. 
   
   
       11 . A compound of  claim 10  wherein X is —(C═O)NH—. 
   
   
       12 . A compound of  claim 1  wherein Q is —(C═O)NR 1 ,R 2 ). 
   
   
       13 . A compound of  claim 12  wherein Q is —(C═O)NHOH. 
   
   
       14 . A compound of  claim 1  wherein n is 0. 
   
   
       15 . A compound of  claim 1  wherein R 3  is H. 
   
   
       16 . A compound of  claim 1  wherein Y is substituted or unsubstituted aryl. 
   
   
       17 . A compound of  claim 16  wherein Y is substituted or unsubstituted phenyl. 
   
   
       18 . (canceled) 
   
   
       19 . A compound of  claim 1  wherein A is selected from the group consisting of:
 (1) —(CH 2 ) 0-4 C(R 1a ,R 2a )(CH 2 ) 0-4 OR 3a ,   (2) —(CH 2 ) 0-4 C(R 1a ,R 2a )N(R 4a ,R 5a ), and   (3) —CH(R 1a ,R 2a ).   
   
   
       20 - 37 . (canceled) 
   
   
       38 . A compound having the following formula (I): 
     
       
         
         
             
             
         
       
     
     or a stereoisomer, pharmaceutically acceptable salt, ester, or prodrug thereof,
 wherein:
 E is selected from the group consisting of:
 (1) H, 
 (2) substituted or unsubstituted C 1 -C 6 -alkyl, 
 (3) substituted or unsubstituted C 2 -C 6 -alkenyl, 
 (4) substituted or unsubstituted C 2 -C 6 -alkynyl, 
 (5) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (6) substituted or unsubstituted aryl, 
 (7) substituted or unsubstituted heterocyclyl, and 
 (8) substituted or unsubstituted heteroaryl; 
 
 L is absent or selected from the group consisting of:
 (1) substituted or unsubstituted C 1 -C 6 -alkyl, 
 (2) —(NR 3L ) 0-1 —(CH 2 ) 0-4 —NR 3L —(CH 2 ) 0-4 —, 
 (3) —(NR 3L ) 0-4 —C(R 1L ,R 2L )—NR 3L —C(R 1L ,R 2L )—, 
 (4) —C(R 1L ,R 2L )—O—C(R 1L ,R 2L )—, 
 (5) —(CH 2 ) 0-4 —NR 3L —C(R 1L ,R 2L )—CONH—(CH 2 ) 0-4 —, 
 (6) —CO—C(R 1L ,R 2L )—NHCO—, 
 (7) —CONR 3L —, 
 (8) —NR 3L CO—, 
 (9) —NR 3L —, 
 (10) —SO 2 NR 3L —, 
 (11) —NR 3L —C(═O)—NR 3L —, 
 (12) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (13) substituted or unsubstituted aryl, 
 (14) substituted or unsubstituted heterocyclyl, and 
 (15) substituted or unsubstituted heteroaryl, 
 wherein:
 each R 1L , R 2L , and R 3L  is independently selected from the group consisting of: 
  (a) H, 
  (b) substituted or unsubstituted C 1 -C 6 -alkyl, 
  (c) C 1 -C 6 -alkyl substituted with aryl, 
  (d) C 1 -C 6 -alkyl substituted with heterocyclyl, and 
  (e) C 1 -C 6 -alkyl substituted with heteroaryl, 
 
 or R 1L  and R 3L , together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S; 
 
 D is absent or selected from the group consisting of:
 (1) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (2) substituted or unsubstituted aryl, 
 (3) substituted or unsubstituted heterocyclyl, and 
 (4) substituted or unsubstituted heteroaryl; 
 
 G is selected from the group consisting of:
 (1) —(CH 2 ) 0-4 —O—(CH 2 ) 0-4 —, 
 (2) —(CH 2 ) 0-4 —S—(CH 2 ) 0-4 —, 
 (3) —(CH 2 ) 0-4 —NR 1G —(CH 2 ) 0-4 —, 
 (4) —C(═O)—, 
 (5) —NR 1G C(═O)—, 
 (6) —C(═O)NR 1G —, 
 (7) —(CH 2 ) 0-4 NHCH 2 C(═O)NR 1G —, 
 (8) —C≡C—, 
 (9) —C≡C—C≡C—, 
 (10) —CR 2G ═CR 2G —, 
 (11) —S(═O)—, 
 (12) —SO 2 —, 
 (13) —C(R 3G ) 2 —S(═O)—, 
 (14) —S(═O)—C(R 3G ) 2 —, 
 (15) —C(R 3G ) 2 —SO 2 —, 
 (16) —SO 2 —C(R 3G ) 2 — 
 (17) —CR 3G ═CR 3G —CR 3G ═CR 3G —, 
 (18) —C(R 3G ) 2 —, 
 (19) —CR 3G ═CR 3G —C≡C—, 
 (20) —C≡C—CR 3G ═CR 3G —, 
 (21) —C(═O)—C≡C—, 
 (22) —C≡C—C(═O)—, 
 (23) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (24) substituted or unsubstituted aryl, 
 (25) substituted or unsubstituted heterocyclyl, and 
 (26) substituted or unsubstituted heteroaryl, 
 wherein:
 R 1G  is substituted or unsubstituted C 1 -C 6 -alkyl; 
 each R 2G  and R 3G  is independently selected from the group consisting of H, a halogen atom, and substituted or unsubstituted C 1 -C 6 -alkyl; 
 
 
 Y is absent or selected from the group consisting of:
 (1) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (2) substituted or unsubstituted aryl, 
 (3) substituted or unsubstituted heterocyclyl, and 
 (4) substituted or unsubstituted heteroaryl; 
 
 X is selected from the group consisting of:
 (1) —(C═O)NR 4 —, 
 (2) —C 1 -C 6 -alkyl-(C═O)NR 4 —, 
 (3) —C 2 -C 6 -alkenyl-(C═O)NR 4 —, 
 (4) —C 2 -C 6 -alkynyl-(C═O)NR 4 —, 
 (5) —CH 2 NR 4 —, 
 (6) —SO 2 NR 4 —, 
 (7) —S(═O)NR 4 —, 
 (8) —NR 4 C(═O)—, and 
 (9) —NR 4 —, 
 or X and A, together with the atoms to which they are attached can form a heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S, 
 or when Y is a bicyclic substituted or unsubstituted heterocyclyl or heteroaryl, then X is absent; 
 
 R 3  is H or substituted or unsubstituted C 1 -C 6 -alkyl, or R 3  and A, together with the atom to which they are attached can form a substituted or unsubstituted 3-10 membered cycloalkyl or a heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring are selected from N, O and S; 
 R 4  is (1) H or substituted or unsubstituted C 1 -C 6 -alkyl, or (2) R 4  and A, together with the atoms to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S, or (3) R 4  and Y, together with the atoms to which they are attached, form a bicyclic substituted or unsubstituted heterocyclyl or heteroaryl; 
 n is an integer from 0-6; 
 A is selected from the group consisting of:
 (1) —C(R 1a ,R 2a )OR 3a , 
 (2) —C(R 1a ,R 2a )N(R 4a ,R 5a ), 
 (3) substituted or unsubstituted C 3 -C 10 -cycloalkyl, 
 (4) substituted or unsubstituted aryl, 
 (5) substituted or unsubstituted heterocyclyl, and 
 (6) substituted or unsubstituted heteroaryl, 
 wherein:
 each R 1a  and R 2a  is independently selected from the group consisting of substituted or unsubstituted C 1 -C 6 -alkyl; 
 each R 3a , R 4a , and R 5a  is independently selected from the group consisting of: 
  (a) H, 
  (b) a halogen atom, 
  (c) substituted or unsubstituted C 1 -C 6 -alkyl, 
  (d) substituted or unsubstituted aryl, 
  (e) substituted or unsubstituted heterocyclyl, and 
  (f) substituted or unsubstituted heteroaryl, 
 
 or R 4a  and R 5a  together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 5 to 8 ring atoms, wherein 1-2 ring atoms of the heterocyclic ring are selected from N, O and S; and
 when A is —C(R 1a ,R 2a )OR 3a , the compound is not 2-{[(4′-ethyl-1,1′-biphenyl-4-yl)carbonyl]amino}-3-hydroxy-3-methylbutanoic acid, 4′-ethyl-N-{2-hydroxy-1-[(hydroxyamino) carbonyl]-2-methylpropyl}-1,1′-biphenyl-4-carboxamide or N-{2-hydroxy-1-[(hydroxyamino)carbonyl]-2-methylpropyl}-4-(phenylethynyl)benzamide; 
 
 
 Q is absent or selected from the group consisting of:
 (1) —C(═O)N(R 1 ,R 2 ), 
 (2) —NHC(═O)N(R 1 ,R 2 ), 
 (3) —N(OH)C(═O)N(R 1 ,R 2 ), 
 (4) —CH(OH)C(═O)N(R 1 ,R 2 ), 
 (5) —CH[N(R 2q , R 3q )]C(═O)N(R 1 ,R 2 ), 
 (6) —CHR 1q C(═O)N(R 1 , R 2 ), 
 (7) —CO 2 H, 
 (8) —C(═O)NHSO 2 R 4q , 
 (9) —SO 2 NH 2 , 
 (10) —N(OH)C(═O)R 1q , 
 (11) —N(OH)SO 2 R 4q , 
 (12) —NHSO 2 R 4q , 
 (13) —SH, 
 (14) —CH(SH)(CH 2 ) 0-1 C(═O)N(R 1 ,R 2 ), 
 (15) —CH(SH)(CH 2 ) 0-1 CO 2 H, 
 (16) —CH(OH)(CH 2 ) 0-1 CO 2 H, 
 (17) —CH(SH)CH 2 CO 2 R 1q , 
 (18) —CH(OH)(CH 2 )SO 2 NH 2 , 
 (19) —CH(CH 2 SH)NHCOR 1q , 
 (20) —CH(CH 2 SH)NHSO 2 R 4q , 
 (21) —CH(CH 2 SR 5q )CO 2 H, 
 (22) —CH(CH 2 SH)NHSO 2 NH 2 , 
 (23) —CH(CH 2 OH)CO 2 H, 
 (24) —CH(CH 2 OH)NHSO 2 NH 2 , 
 (25) —C(═O)CH 2 CO 2 H, 
 (26) —C(═O)(CH 2 ) 0-1 CONH 2 , 
 (27) —OSO 2 NHR 5q , 
 (28) —SO 2 NHNH 2 , 
 (29) —P(═O)(OH) 2 , 
 
 
 
     
       
         
         
             
             
         
       
       
         
           (33) —N(OH)C(═O)CR 1 R 2 , 
           wherein:
 R 1  is selected from the group consisting of: 
  (1) —H, 
  (2) —OH, 
  (3) —OC 1 -C 6 -alkyl, 
  (4) —N(R 2q , R 3q ), and 
  (5) substituted or unsubstituted C 1 -C 6 -alkyl; 
 R 2  is selected from the group consisting of: 
  (1) H, 
  (2) substituted or unsubstituted C 1 -C 6 -alkyl, 
  (3) substituted or unsubstituted C 2 -C 6 -alkenyl, 
  (4) substituted or unsubstituted C 2 -C 6 -alkenyl, 
  (5) substituted or unsubstituted aryl, 
  (6) substituted or unsubstituted heterocyclyl, and 
  (7) substituted or unsubstituted heteroaryl, 
 or R 1  and R 2 , together with the N atom to which they are attached can form a substituted or unsubstituted heterocyclic ring, having from 3 to 10 ring atoms, wherein 1-4 ring atoms of the heterocyclic ring are selected from N, O and S; and 
 each R 1q , R 2q , R 3q , R 4q , and R 5q  is independently selected from the group consisting of H and C 1 -C 6  alkyl. 
 
         
       
     
   
   
       39 . A compound of  claim 38  wherein A is —C(R 1a ,R 2a )N(R 4a ,R 5a ). 
   
   
       40 . A compound of  claim 39  wherein A is —C(CH 3 ) 2 NH 2 . 
   
   
       41 . A compound of  claim 38  wherein A is —C(R 1a ,R 2a )OR 3a . 
   
   
       42 . A compound of  claim 38  wherein A is selected from the group consisting of:
 (1) substituted or unsubstituted C 3 -C 10 -cycloalkyl,   (2) substituted or unsubstituted aryl,   (3) substituted or unsubstituted heterocyclyl, and   (4) substituted or unsubstituted heteroaryl.   
   
   
       43 .- 44 . (canceled) 
   
   
       45 . A compound of  claim 38  wherein G is selected from the group consisting of:
 (1) —C≡C—,   (2) —C≡C—C≡C—,   (3) —CR 3G ═CR 3G —C≡C—, and   (4) —C≡C—CR 3G ═CR 3G —.   
   
   
       46 . A compound of  claim 45  wherein G is selected from the group consisting of:
 (1) —C≡C—,   (2) —C≡C—C≡C—,   (3) —CH═CH—C≡C—, and   (4) —C≡C—CH═CH—.   
   
   
       47 - 52 . (canceled) 
   
   
       53 . A compound of  claim 38  wherein X is —(C═O)NR 4 —. 
   
   
       54 . A compound of  claim 53  wherein X is —(C═O)NH—. 
   
   
       55 . A compound of  claim 38  wherein Q is —(C═O)N(R 1 ,R 2 ). 
   
   
       56 . A compound of  claim 55  wherein Q is —(C═O)NHOH. 
   
   
       57 . A compound of  claim 38  wherein n is 0. 
   
   
       58 . A compound of  claim 38  wherein R 3  is H. 
   
   
       59 . A compound of  claim 38  wherein Y is substituted or unsubstituted aryl. 
   
   
       60 . A compound of  claim 59  wherein Y is substituted or unsubstituted phenyl. 
   
   
       61 - 73 . (canceled) 
   
   
       74 . A pharmaceutical composition comprising a compound of  claim 1  and a pharmaceutically acceptable carrier or diluent. 
   
   
       75 . A method for treating a subject with a gram-negative bacterial infection comprising administering to the subject in need thereof an antibacterially effective amount of a compound of  claim 1 . 
   
   
       76 . (canceled) 
   
   
       77 . A pharmaceutical composition comprising a compound of  claim 38  and a pharmaceutically acceptable carrier or diluent. 
   
   
       78 . A method for treating a subject with a gram-negative bacterial infection comprising administering to the subject in need thereof an antibacterially effective amount of a compound of  claim 38 .