Therapeutic agents, and methods of making and using the same

Abstract

In part, the present invention is directed to antibacterial compounds.

1 . A compound of formula I: 
       
         
           
           
               
               
           
         
         wherein, independently for each occurrence, 
         A is a monocyclic ring of 4-7 atoms containing 0-2 heteroatoms, a bicyclic ring of 8-12 atoms containing 0-4 heteroatoms or a tricyclic ring of 8-12 atoms containing 0-6 heteroatoms wherein the rings are independently aliphatic, aromatic, heteroaryl or heterocyclic in nature, the heteroatoms are selected from N, S or O and the rings are optionally substituted with one or more groups selected from C 1-4  alkyl, OR″, CN, OCF 3 , F, Cl, Br, I; wherein R″ is H, alkyl, aralkyl, or heteroaralkyl; 
         R is 
       
       
         
           
           
               
               
           
         
         wherein, independently for each occurrence,
 R 1  is H, alkyl, or aryl, or R 1  and R 2  taken together form a fused ring; 
 R 2  is H, alkyl, or aryl, or R 2  and R 1  taken together form a fused ring, or R 2  and R 3  taken together form a spirocyclic ring; 
 R 3  is H, alkyl, or aryl, or R 3  and R 2  taken together form a spirocyclic ring; 
 R 4  is H, alkyl, aryl, hydroxy substituted alkyl, or —C(O)ONa; 
 R 5  is H, alkyl, or aryl; 
 R 6  is H, alkyl, or aryl; and 
 L 1  is O or H 2 ; 
 
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         2 . The compound of  claim 1 , wherein A is selected from the following: 
       
         
           
           
               
               
           
         
         wherein, independently for each occurrence, 
         R 7  is H, C 1-4  alkyl, C 1-4  haloalkyl, C 1-4  alkenyl, OR″, CN, OCF 3 , F, Cl, Br, I; wherein R″ is H, alkyl, aralkyl, or heteroaralkyl; and 
         L is O, S, or NR 5 . 
       
     
     
         3 . The compound of  claim 1 , wherein A is selected from the following: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         4 . The compound of  claim 2 , wherein the compound has formula Ia: 
       
         
           
           
               
               
           
         
         wherein: 
         A is selected from the following: 
       
       
         
           
           
               
               
           
         
       
     
     
         5 . The compound of  claim 2 , wherein the compound has formula Ib: 
       
         
           
           
               
               
           
         
         wherein: 
         A is selected from the following: 
       
       
         
           
           
               
               
           
         
       
     
     
         6 . The compound of  claim 2 , wherein the compound has formula Ic: 
       
         
           
           
               
               
           
         
         wherein: 
         A is selected from the following: 
       
       
         
           
           
               
               
           
         
       
     
     
         7 . The compound of  claim 2 , wherein the compound has formula Id: 
       
         
           
           
               
               
           
         
         wherein: 
         A is 
       
       
         
           
           
               
               
           
         
       
     
     
         8 . The compound of  claim 2 , wherein the compound has formula Ie: 
       
         
           
           
               
               
           
         
         wherein: 
         A is selected from the following: 
       
       
         
           
           
               
               
           
         
       
     
     
         9 . The compound of  claim 2 , wherein the compound has formula If: 
       
         
           
           
               
               
           
         
       
     
     
         10 . The compound of  claim 1 , wherein the compound is selected from the following:
 (E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(2-ethoxy-3-trifluoromethoxybenzyl)acrylamide hydrochloride;   (E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(2-propoxy-3-trifluoromethoxybenzyl)acrylamide hydrochloride;   (E)-N-(3-Chloro-2-ethoxybenzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide;   (E)-N-(3-Chloro-2-propoxybenzyl)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methylacrylamide hydrochloride;   (E)-N-(2-Isobutoxy-3-methoxybenzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide;   (E)-N-(3-Isopropyl-2-propoxybenzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide;   (E)-N-(2-Ethoxy-3-isopropylbenzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide;   (E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(3-isopropyl-2-propoxybenzyl)-N-methylacrylamide hydrochloride;   (E)-N-(3-Isopropyl-2-propoxybenzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide;   (S)-(+)-(E)-N-Methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(10-oxo-2,3,4,9,10,10a-hexahydro-1H-3a,8,9-triazabenzo[f]azulen-6-yl)acrylamide hydrochloride;   (R)-(−)-(E)-N-Methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(10-oxo-2,3,4,9,10,10a-hexahydro-1H-3a,8,9-triazabenzo[f]azulen-6-yl)acrylamide hydrochloride;   (E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(2-isobutoxy-3-methoxybenzyl)-N-methylacrylamide hydrochloride;   (E)-3-(6-amino-pyridin-3-yl)-N-(3-chloro-4-fluoro-benzo[b]thiophen-2-ylmethyl)-N-methylacrylamide hydrochloride;   (E)-3-(6-amino-pyridin-3-yl)-N-(3-chloro-7-fluoro-benzo[b]thiophen-2-ylmethyl)-N-methylacryl amide hydrochloride;   (E)-6-{2-[methyl-(3-methyl-b enzo[b]thiophen-2-ylmethyl)-carbamoyl]-vinyl}-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid sodium salt;   (E)-spiro[2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-3,1′-cyclopentane]-7-yl-N-(3-methyl-benzofuran-2-ylmethyl)-N-methylacrylamide hydrochloride;   (E)-spiro[2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-3,1′-cyclopentane]-7-yl-N-(3-methoxy-2-propoxybenzyl)-N-methylacrylamide hydrochloride;   (E)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3,-e][1,4]diazepin-7-yl)acrylamide hydrochloride;   (E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]dizepin-7-yl)-N-methyl-N-(3-propyl-benzofuran-2-ylmethyl)acrylamide hydrochloride;   (E)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(3-ethyl-benzofuran-2-ylmethyl)-N-methylacrylamide hydrochloride;   (E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide hydrochloride;   (E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-(3-methoxy-2-propoxybenzyl)-N-methylacrylamide hydrochloride;   (E)-3-(3,3-Dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide hydrochloride;   (E)-N-Methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochloride;   (E)-3-(2,2-Dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide;   (E)-3-(2,2-Dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methyl-benzofuran-2-ylmethyl)-acrylamide hydrochloride;   (E)-3-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide hydrochloride;   (E)-N-(2-Ethoxy-3-isopropylbenzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide hydrochloride;   (E)-N-(2-Isobutoxy-3-methoxybenzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochloride;   (E)-3-[6-Amino-5-(1-hydroxy-1-methyl-ethyl)-pyridin-3-yl]-N-methyl-N-(3-methyl-benzofuran-2-ylmethyl)-acrylamide;   (E)-3-[6-Amino-5-(1-hydroxy-1-methyl-ethyl)-pyridin-3-yl]-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-acrylamide;   (E)-3-[6-Amino-5-(1-hydroxy-1-methyl-ethyl)-pyridin-3-yl]-N-methyl-N-(2-methyl-benzofuran-3-ylmethyl)-acrylamide;   (E)-3-(6-amino-pyridin-3-yl)-N-(3-cyano-1H-indol-2-ylmethyl)-N-methyl-acrylamide;   (E)-N-(3-cyano-1H-indol-2-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide;   (E)-N-Methyl-N-(3-methyl-benzofuran-2-ylmethyl)-3-(3-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide hydrochloride;   (E)-N-(1,2-Dimethyl-1H-indol-3-ylmethyl)-N-methyl-3-(3-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide;   (E)-N-Methyl-N-(2-methyl-benzofuran-3-ylmethyl)-3-(4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide hydrochloride;   (E)-N-Methyl-N-(3-methyl-benzofuran-2-ylmethyl)-3-(4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide hydrochloride;   (E)-N-(3-Methoxy-2-propoxy-benzyl)-N-methyl-3-(4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide hydrochloride;   (E)-N-Methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide;   (E)-N-(3-Methoxy-2-propoxy-benzyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide;   (E)-N-Methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide;   (E)-3-(6-Amino-pyridin-3-yl)-N-(3-chloro-benzofuran-2-ylmethyl)-N-methyl-acrylamide hydrochloride;   (E)-N-(3-Chloro-benzofuran-2-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide;   (E)-N-(3-Chloro-benzofuran-2-ylmethyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide hydrochloride;   (E)-N-(1H-Indol-5-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide;   (E)-N-Methyl-N-(1-methyl-1H-indol-5-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide;   (E)-N-(3-tert-Butyl-2-propoxy-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide;   (E)-N-Methyl-N-(1-methyl-1H-indol-6-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide;   (E)-N-(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-6-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide;   (E)-N-(2,2-Dimethyl-2,3-dihydro-benzofuran-7-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide;   (E)-N-(1H-Indol-4-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylamide;   (E)-3-(2,2-Dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-acrylamide;   (E)-3-(2,2-Dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(2-methyl-benzofuran-3-ylmethyl)-acrylamide;   (E)-3-(2,2-Dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-(3-methoxy-2-propoxy-benzyl)-N-methyl-acrylamide;   (E)-3-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-(2-methyl-benzo furan-3-ylmethyl)-acrylamide hydrochloride;   (E)-N-Methyl-N-(2-methyl-benzofuran-3-ylmethyl)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-acrylamide;   (E)-N-Methyl-N-(3-methyl-benzofuran-2-ylmethyl)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-acrylamide;   (E)-N-(3-Chloro-benzofuran-2-ylmethyl)-3-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-acrylamide;   (E)-N-methyl-(1H-indol-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]napthyridin-3-yl)acrylamide;   (E)-3-(2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide hydrochloride;   (E)-3-(6-aminopyridin-3-yl)-N-((5-fluoro-3-methylbenzo[b]thiophen-2-yl)methyl)-N-methylacrylamide hydrochloride;   (E)-N-((3-chlorobenzofuran-2-yl)methyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-(3-methoxy-2-propoxybenzyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-((3-isopropylbenzofuran-2-yl)methyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-((3-ethylbenzofuran-2-yl)methyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-((5-fluoro-3-methylbenzo[b]thiophen-2-yl)methyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-((5-fluoro-3-methylbenzo[b]thiophen-2-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-((5-fluoro-1-methyl-1H-indol-2-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-((3-ethylbenzofuran-2-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-((3-isopropylbenzofuran-2-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-(benzofuran-5-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-(benzo[b]thiophen-5-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-methyl-N-((1-methyl-1H-indol-4-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-((1-ethyl-1H-indol-4-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-((1H-benzo[d]imidazol-5-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamide;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochloride;   (E)-3-((6-aminopyridin-3-yl)-N-methyl-N-((3-methyl-1H-indol-2-yl)methyl)acrylamide;   (E)-N-methyl-N-((3-methyl-1H-indol-2-yl)methyl)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-((3,7-dimethyl-1H-indol-2-yl)methyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-methyl-N-((3-methyl-7-(trifluoromethyl)-1H-indol-2-yl)methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-((3,7-dimethyl-1H-indol-2-yl)methyl)-N-methyl-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamide;   (E)-N-((3-ethyl-1H-indol-2-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-((3-ethyl-1H-indol-2-yl)methyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-((3-vinyl-1H-indol-2-yl)methyl)acrylamide;   (E)-N-((1,3-dimethyl-1H-indol-2-yl)methyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-((1,3-dimethyl-1H-indol-2-yl)methyl)-N-methyl-3-(2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide;   (E)-N-methyl-N-((3-methyl-7-(trifluoromethyl)-1H-indol-2-yl)methyl)-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-methyl-N-((3-methyl-7-(trifluoromethyl)-1H-indol-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-((7-ethyl-3-methyl-1H-indol-2-yl)methyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)acrylamide;   (E)-N-((7-ethyl-3-methyl-1H-indol-2-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide;   (E)-N-((3,6-dimethyl-1H-indol-5-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3yl)acrylamide;   (E)-N-((3,6-dimethyl-1H-indol-5-yl)methyl)-N-methyl-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-yl)acrylamide;   (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-7,8-dihydro-1,8-naphthyridin-3-yl)acrylamide; or   (E)-3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide.   
     
     
         11 .- 13 . (canceled) 
     
     
         14 . A pharmaceutical composition comprising a compound of  claim 1  and a pharmaceutically acceptable carrier or excipient. 
     
     
         15 .- 32 . (canceled) 
     
     
         33 . A method of treating a subject with a bacterial illness comprising administering to the subject the pharmaceutical composition of  claim 14 . 
     
     
         34 . The method of claim  32 , wherein the compound inhibits the Fab I activity of a microbe with an IC 50  at least 1 order of magnitude lower than the IC 50  for inhibiting enoyl CoA hydratase of a mammal. 
     
     
         35 . The method of  claim 33 , wherein the mammal is a human. 
     
     
         36 . The method of claim  32 , wherein the compound inhibits the Fab I activity of a microbe with a K i  at least 1 order of magnitude lower than the K i  for inhibiting enoyl CoA hydratase of a mammal. 
     
     
         37 . The method of  claim 35 , wherein the mammal is a human. 
     
     
         38 - 39 . (canceled)