US2004029879A1PendingUtilityA1
Heterocycle carboxamides as antiviral agents

Priority: Jul 12, 2000Filed: Jul 31, 2003Published: Feb 12, 2004
Est. expiryJul 12, 2020(expired)· nominal 20-yr term from priority
Inventors:David John Anderson Thomas Beauchamp Gordon L. Bundy Fred Lawrence Ciske John Farrell David R. Graber Michael James Genin Thomas Judge Malcolm W. Moon Mark Edward Schnute Joseph Walter Strohbach Suvit Thaisrivongs Atli Thorarensen Steven Ronald Turner Valerie A. Vaillancourt Allison Wolf
A61P 31/12A61P 43/00A61P 31/22C07D 471/06
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References
Claims
Abstract

The present invention provides a compound of formula I which is useful as antiviral agents, in particular, as agents against viruses of the herpes family.
Claims

exact text as granted — not AI-modified
What is claimed is:  
     
         1 . A compound of formula I,  
       
         
           
           
               
               
           
         
       
       wherein, 
 X is Cl, Br, F, CN or NO 2 ;  
 G is 
 (a) C 1-4 alkyl which is fully saturated or partially unsaturated and is substituted by hydroxy, or  
 (b) C 1-4 alkyl substituted by NR 1 R 2  or 4-tetrahydropyran;  
 
 R 1  is C 2-7 alkyl substituted by hydroxy, C 1-4 alkoxy, or aryl;  
 R 2  is hydrogen or C 1-7 alkyl;  
 or R 1  and R 2  together with the nitrogen to which they are attached form (a) a morpholine which may be optionally substituted by aryl or C 1-7 alkyl; or (b) a pyrrolidine ring substituted by hydroxy;  
 W is a heterocycle of formula W1, W2, W3, W4, W5, W6, W7 or W8 
                     
 A is CR 4  or nitrogen;  
 B is CR 5  or nitrogen;  
 D is 
 (a) —(CR 13 R 14 ) a —, where a is 2 or 3  
 (b) —(CR 15 R 16 ) 4 —,  
 (c) —Y—CR 13 R 14 —CR 13 R 14 —,  
 (d) —CR 13 R 14 —Y—CR 13 R 14 —,  
 (e) —Y—CR 13 R 14 —Y—,  
 (f) —CR 13 R 14 —CR 13 R 14—Y—,    
 (g) —Y—(CR 15 R 16 ) n —,  
 (h) —Y—CR 15 ═CR 15 —,  
 (i) —Y—CR 15 ═N—,  
 (j) —CR 15 ═CR 15 —N—,  
 (k) —N═CR 15 —Y—,  
 (l) —(CR 15 R 16 ) b —N═CR 15 —, where b is 0 or 1  
 (m) —CR 15 ═N—(CR 15 R 16 ) b —, where b is 0 or 1  
 (n) —N═N—,  
 (o) —N═CR 15 —(CR 15 R 16 ) b —, where b is 0 or 1  
 (p) —CR 15 ═CR 15 —,  
 (q) —N═N—Y—,  
 (r) —Y—N═N—,  
 (s) —Y—N═CR 15 —, or  
 (t) —CR 15 R 16 —Y—CR 15 R 16 —CR 15 R 16 —;  
 
 E is CR 8  or nitrogen;  
 J is CR 15  or nitrogen;  
 K is 
 (a) —(CR 15 R 16 ) a —, where a is 2 or 3, or  
 (b) —CR 15 ═CR 15 —;  
 
 L is 
 (a) —(CR 15 R 16 ) a —, where a is 2 or 3, or  
 (b) —Y—(CR 15 R 16 )—(CR 15 R 16 )—;  
 
 Y is oxygen, S(O) m , or NR 7 ;  
 with the provisos that: 
 when W is of formula W1; G is C 1-4 alkyl which is fully saturated and is substituted by hydroxy or morpholinyl, in which morpholinyl is attached through nitrogen; A is CR 4 ; B is CR 5 ; and R 8  is hydrogen then at least one of R 13 , R 14 , or R 7  is not hydrogen or C 1-7 alkyl;  
 when W is of formula W1, A is CR 4 , B is CR 5 , D is —Y—CR 13 R 14 —CR 13 R 14 —, and R 8  is hydrogen then Y is not oxygen;  
 when W is of formula W1, A is CR 4 , and B is CR 5  then D is not —CR 15 ═CR 15 —;  
 
 R 4  is H, halogen, or C 1-4 alkyl optionally substituted by one to three halogens;  
 R 5  is 
 (a) H,  
 (b) halo,  
 (c) OR 12 ,  
 (d) SR 12 ,  
 (e) C 1-7 alkyl which may be partially unsaturated and optionally substituted by one or more substituents selected from OR 12 , SR 12 , NR 10 R 11 , or halo,  
 (f) C 3-8 cycloalkyl which may be partially unsaturated and is optionally substituted by one or more substituents selected from halogen, OR 12 , SR 12 , or NR 10 R 11 ,  
 (g) (C═O)R 9 ,  
 (h) S(O) m R 9 ,  
 (i) (C═O)OR 2 ,  
 (j) NHSO 2 R 9 ,  
 (k) nitro, or  
 (l) cyano;  
 
 R 7  is 
 (a) H,  
 (b) C 1-7 alkyl which may be partially unsaturated and optionally substituted by one or more substituents selected from OR 12 , SR 12 , NR 10 R 11 , or halo,  
 (c) C 3-8 cycloalkyl which may be partially unsaturated and is optionally substituted by one or more substituents selected from halogen, OR 12 , SR 12 , or NR 10 R 11 ,  
 (d) aryl,  
 (e) het,  
 (f) (C═O)R 9 , or  
 (g) S(O) m R 9 ;  
 
 R 8  is 
 (a) H,  
 (b) C 1-7 alkyl which may be partially unsaturated and optionally substituted by one or more substituents selected from OR 12 , SR 12 , NR 10 R 11 , or halo,  
 (c) OR 12 , or  
 (d) SR 12 ;  
 
 R 9  is 
 (a) C 1-7 alkyl optionally substituted by OR 12  or NR 2 R 2 ,  
 (b) C 3-8 cycloalkyl optionally substituted by OR 12  or NR 2 R 2 ,  
 (c) NR 10 R 11 ,  
 (d) aryl, or  
 (e) het, wherein said het is bound through a carbon atom;  
 
 R 10  and R 11  are independently 
 (a) H,  
 (b) aryl,  
 (c) C 1-7 alkyl which may be partially unsaturated and is optionally substituted by one or more substituents selected from CONR 2 R 2 , CO 2 R 2 , het, aryl, cyano, or halo,  
 (d) C 2-7 alkyl which may be partially unsaturated and is substituted by one or more substituents selected from NR 2 R 2 , OR 2 , or SR 2 ,  
 (e) C 3-8 cycloalkyl which may be partially unsaturated and is optionally substituted by one or more substituents selected from halogen, OR 2 , SR 2 , or NR 2 R 2 , or  
 (f) R 10  and R 11  together with the nitrogen to which they are attached form a het;  
 
 R 12  is 
 (a) H,  
 (b) aryl,  
 (c) het  
 (d) C 1-7 alkyl optionally substituted by aryl, or halogen,  
 (e) C 2-7 alkyl substituted by OR 2 , SR 2 , or NR 2 R 2 , or  
 (f) C 3-8 cycloalkyl which may be partially unsaturated and is optionally substituted by one or more substituents selected from halogen, OR 2 , SR 2 , or NR 2 R 2 ;  
 
 R 13 , R 14 , R 15 , and R 16  are independently 
 (a) H  
 (b) C 1-7 alkyl which may be partially unsaturated and optionally substituted by one or more OR 12 , SR 12 , NR 10 R 11 , or halo groups,  
 (c) C 3-8 cycloalkyl which may be partially unsaturated and is optionally substituted by one or more substituents selected from halogen, OR 12 , SR 12 , or NR 10 R 11 ,  
 (d) aryl,  
 (e) het, wherein said het is bound through a carbon atom,  
 (f) OR 12 ,  
 (g) SR 12 ,  
 (h) NR 10 R 11 ;  
 (i) (C═O)OR 2 , or  
 (j) R 13  and R 14  or R 15  and R 16  together with the carbon to which they are attached form (C═O);  
 
 each m is independently 0, 1 or 2;  
 each n is independently 1 or 3;  
 aryl is a phenyl radical or an ortho-fused bicyclic carbocyclic radical wherein at least one ring is aromatic, and aryl may be optionally substituted with one or more substituents selected from halo, OH, cyano, NR 2 R 2 , CO 2 R 2 , CF 3 , C 1-6 alkoxy, and C 1-6  alkyl which maybe further substituted by one to three SR 2 , NR 2 R 2 , OR 2 , or CO 2 R 2  groups;  
 het is a four- (4), five- (5), six- (6), or seven- (7) membered saturated or unsaturated heterocyclic ring having 1, 2, or 3 heteroatoms selected from oxygen, sulfur, or nitrogen, which is optionally fused to a benzene ring, or any bicyclic heterocycle group, and het may be optionally substituted with one or more substituents selected from halo, OH, cyano, phenyl, CO 2 R 2 , CF 3 , C 1-6 alkoxy, oxo, oxime, and C 1-6  alkyl which may be further substituted by one to three SR 2 , NR 2 R 2 , OR 2 , or CO 2 R 2  groups;  
 halo or halogen is F, Cl, Br, I;  
 1 represents the point of attachment between W and G;  
 2 represents the point of attachment between W and the carbonyl group of Formula (I);  
 and pharmaceutically acceptable salts thereof.  
 
     
     
         2 . A compound of  claim 1  wherein W is of the formula W1.  
     
     
         3 . A compound of  claim 2  wherein W is of the formula W1.1.  
     
     
         4 . A compound of  claim 2  wherein W is of the formula W1.3.  
     
     
         5 . A compound of  claim 2  wherein W is of the formula W1.5.  
     
     
         6 . A compound of  claim 2  wherein W is of the formula W1.6.  
     
     
         7 . A compound of  claim 2  wherein W is of the formula W1.7.  
     
     
         8 . A compound of  claim 2  wherein W is of the formula W1.8.  
     
     
         9 . A compound of  claim 2  wherein W is of the formula W1.9.  
     
     
         10 . A compound of  claim 2  wherein W is of the formula W1.10.  
     
     
         11 . A compound of  claim 2  wherein W is of the formula W1.11.  
     
     
         12 . A compound of  claim 2  wherein W is of the formula W1.14.  
     
     
         13 . A compound of  claim 2  wherein W is of the formula W1.15.  
     
     
         14 . A compound of  claim 2  wherein W is of the formula W1.17.  
     
     
         15 . A compound of  claim 2  wherein W is of the formula W1.18.  
     
     
         16 . A compound of  claim 2  wherein W is of the formula W1.19.  
     
     
         17 . A compound of  claim 2  wherein W is of the formula W1.20.  
     
     
         18 . A compound of  claim 2  wherein W is of the formula W1.23.  
     
     
         19 . A compound of  claim 2  wherein W is of the formula W1.24.  
     
     
         20 . A compound of  claim 2  wherein W is of the formula W1.25.  
     
     
         21 . A compound of  claim 2  wherein W is of the formula W1.26.  
     
     
         22 . A compound of  claim 2  wherein W is of the formula W1.52.  
     
     
         23 . A compound of  claim 1  wherein W is of the formula W2.  
     
     
         24 . A compound of  claim 1  wherein W is of the formula W3.  
     
     
         25 . A compound of  claim 24  wherein W is of the formula W3.1.  
     
     
         26 . A compound of  claim 1  wherein W is of the formula W4.  
     
     
         27 . A compound of  claim 26  wherein W is of the formula W4.1.  
     
     
         28 . A compound of  claim 1  wherein W is of the formula W5.  
     
     
         29 . A compound of  claim 1  wherein W is of the formula W6.  
     
     
         30 . A compound of  claim 1  wherein W is of the formula W7.  
     
     
         31 . A compound of  claim 1  wherein W is of the formula W8.  
     
     
         32 . The compound according to  claim 1 , wherein X is Cl.  
     
     
         33 . The compound according to  claim 1  wherein G is 4-morpholinylmethyl.  
     
     
         34 . The compound according to  claim 1  wherein G is 3-hydroxypropyl.  
     
     
         35 . The compound according to  claim 1  wherein G is 3-hydroxy-1-propynyl.  
     
     
         36 . The compound according to  claim 1  wherein G is tetrahydro-2H-pyran-4-ylmethyl.  
     
     
         37 . A compound of  claim 2  where R 8  is hydrogen.  
     
     
         38 . A compound of  claim 37  where A is CR 4  and B is CR 5 .  
     
     
         39 . A compound of  claim 38  where R 4  is hydrogen and R 5  is hydrogen.  
     
     
         40 . The compound according to  claim 1  which is selected from the group consisting of 
 N-(4-chlorobenzyl)-8-(4-morpholinylmethyl)-6-oxo-6H-imidazo[4,5,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-8-(3-hydroxy-1-propynyl)-6-oxo-6H-imidazo[4,5,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-8-(3-hydroxypropyl)-6-oxo-6H-imidazo[4,5,1-ij]quinoline-5-carboxamide;  
 1-amino-N-(4-chlorobenzyl)-8-(3-hydroxy-1-propynyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide;  
 1-amino-N-(4-chlorobenzyl)-8-(3-hydroxypropyl)-6-oxo-1,2-dihydro-6H-pyrrolo-[3,2,1-ij]quinoline-5-carboxamide;  
 1-amino-N-(4-chlorobenzyl)-8-(4-morpholinylmethyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-2-(hydroxymethyl)-8-(3-hydroxy-1-propynyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-8-(3-hydroxyprop-1-ynyl)-2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-7-oxo-2,3-dihydro-7H-[1,3,4]-oxadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(tetrahydro-2H-pyran4-ylmethyl)-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxyprop-1-ynyl)-3-methyl-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-7-oxo-2,3-dihydro-7H-[1,3,4]thiadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-7-oxo-2,3-dihydro-7H-[1,3,4]-thiadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-7H-[1,3,4]thiadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(tetrahydro-2H-pyran-4-ylmethyl)-7-oxo-2,3-dihydro-7H-[1,3,4]thiadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-3-methyl-9-(morpholin-4-ylmethyl)-7-oxo-7H-[1,4]thiazino-[2,3,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-3-methyl-7-oxo-9-(tetrahydro-2H-pyran-4-ylmethyl)-7H-[1,4]-thiazino[2,3,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-3-methyl-7-oxo-7H-[1,4]thiazino[2,3,4-ij]-quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxyprop-1-ynyl)-3-methyl-7-oxo-7H-[1,4]thiazino [2,3,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(morpholin-4-ylmethyl)-7-oxo-2-pyridin-3-yl-7H-[1,4]thiazino-[2,3,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-7-oxo-3-phenyl-1H,7H-[1,3]oxazino-[5,4,3-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-7-oxo-3-phenyl-1H,7H-[1,3]oxazino[5,4,3-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-7-oxo-3-phenyl-9-(tetrahydro-2H-pyran-4-ylmethyl)-1H,7H-[1,3]oxazino[5,4,3-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-3-phenyl-1H,7H-[1,3]oxazino-[5,4,3-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-1-methyl-7-oxo-3-phenyl-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-1-methyl-7-oxo-3-phenyl-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(tetrahydro-2H-pyran-4-ylmethyl)-1-methyl-7-oxo-3-phenyl-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-1-methyl-7-oxo-3-phenyl-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-2,3,7-trioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-2,3,7-trioxo-2,3-dihydro-1H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-2,3,7-trioxo-2,3-dihydro-1H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-3,7-dioxo-2,3-dihydro-1H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-3,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-3,7-dioxo-2,3-dihydro-1H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-1-methyl-7-oxo-2,3-dihydro-1H,7H-[1,2,4]triazino[5,6, 1-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-1-methyl-7-oxo-2,3-dihydro-1H,7H-[1,2,4]triazino[5,6, 1-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-1-methyl-7-oxo-2,3-dihydro-1H,7H-[1,2,4]triazino[5,6, 1-ij]quinoline-6-carboxamide;  
 3-benzyl-N-(4-chlorobenzyl)-9-(tetrahydro-2H-pyran-4-ylmethyl)-1-methyl-7-oxo-2,3-dihydro-1H,7H-[1,2,4]triazino[5,6, 1-ij]quinoline-6-carboxamide;  
 1-benzyl-N-(4-chlorobenzyl)-5-(3-hydroxy-1-propynyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[3,2, 1-ij]cinnoline-8-carboxamide;  
 1-benzyl-N-(4-chlorobenzyl)-5-(3-hydroxypropyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]cinnoline-8-carboxamide;  
 1-benzyl-N-(4-chlorobenzyl)-5-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]cinnoline-8-carboxamide;  
 1-benzyl-N-(4-chlorobenzyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]cinnoline-8-carboxamide;  
 N-(4-Chlorobenzyl)-5-(3-hydroxyprop-1-ynyl)-1-methyl-7-oxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]cinnoline-8-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-7-oxo-3-phenyl-1H,7H-[1,3]thiazino-[5,4,3-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-7-oxo-3-phenyl-1H,7H-[1,3]thiazino[5,4,3-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(tetrahydro-2H-pyran-4-ylmethyl)-7-oxo-3-phenyl-1H,7H-[1,3]thiazino[5,4,3-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-3-phenyl-1H,7H-[1,3]thiazino-[5,4,3-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-2-methyl-7-oxo-3-phenyl-2,3-dihydro-1H,7H-pyrido[3,2, 1-ij]quinazoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-2-methyl-7-oxo-3-phenyl-2,3-dihydro-1H,7H-pyrido[3,2, 1-ij]quinazoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-2-methyl-7-oxo-3-phenyl-2,3-dihydro-1H,7H-pyrido[3,2, 1-ij]quinazoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(tetrahydro-2H-pyran-4-ylmethyl)-2-methyl-7-oxo-3-phenyl-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]quinazoline-6-carboxamide;  
 2-benzyl-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]quinazoline-6-carboxamide;  
 2-benzyl-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-3,7-dioxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]quinazoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-2-(4-morpholinyl)-7-oxo-7H-[1,3,4]-thiadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-2-(4-morpholinyl)-7-oxo-7H-[1,3,4]-thiadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-2-(4-morpholinyl)-9-(4-morpholinylmethyl)-7-oxo-7H-[1,3,4]-thiadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-2-(4-morpholinyl)-7-oxo-9-(tetrahydro-2H-pyran-4-ylmethyl)-7H-[1,3,4]thiadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-7-oxo-2,3-dihydro-1H,7H-pyrazino[3,2,1-ij][1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-1H,7H-pyrazino-[3,2,1-ij][1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-7-oxo-2,3-dihydro-1H,7H-pyrazino-[3,2,1-ij][1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-7-oxo-2,3-dihydro-7H-[1,4]thiazino[2,3,4-ij][1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-7H-[1,4]thiazino-[2,3,4-ij][1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-7-oxo-2,3-dihydro-7H-[1,4]thiazino-[2,3,4-ij][1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino-[2,3,4-ij][1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino-[2,3,4-ij][1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij][1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-3,7-dioxo-3H,7H-pyrido[1,2,3-de]-quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-3,7-dioxo-3H,7H-pyrido[1,2,3-de]-quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-3,7-dioxo-3H,7H-pyrido[1,2,3-de]-quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-2-[(4-chlorobenzyl)amino]-9-(4-morpholinylmethyl)-7-oxo-3H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 2-(benzylamino)-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-3H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-10-(3-hydroxypropyl)-2,4,8-trioxo-1,2,3,4-tetrahydro-8H-[1,4]-diazepino[3,2,1-ij]quinoline-7-carboxamide;  
 N-(4-chlorobenzyl)-10-(3-hydroxy-1-propynyl)-2,4,8-trioxo-1,2,3,4-tetrahydro-8H-[1,4]diazepino[3,2,1-ij]quinoline-7-carboxamide;  
 N-(4-chlorobenzyl)-10-(4-morpholinylmethyl)-2,4,8-trioxo-1,2,3,4-tetrahydro-8H-[1,4]diazepino[3,2,1-ij]quinoline-7-carboxamide;  
 N-(4-chlorobenzyl)-10-(4-morpholinylmethyl)-2,8-dioxo-1,2,3,4-tetrahydro-8H-[1,4]diazepino[3,2,1-ij]quinoline-7-carboxamide;  
 N-(4-chlorobenzyl)-8-(4-morpholinylmethyl)-2,6-dioxo-1,2-dihydro-6H-imidazo-[4,5,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-8-(3-hydroxy-1-propynyl)-2,6-dioxo-1,2-dihydro-6H-imidazo-[4,5,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-8-(3-hydroxypropyl)-2,6-dioxo-1,2-dihydro-6H-imidazo[4,5,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-8-(4-morpholinylmethyl)-2,6-dioxo-1-[2-(1-piperidinyl)ethyl]-1,2-dihydro-6H-imidazo[4,5,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-1-[2-(4-methyl-1-piperazinyl)ethyl]-8-(4-morpholinylmethyl)-2,6-dioxo-1,2-dihydro-6H-imidazo[4,5,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-10-(4-morpholinylmethyl)-8-oxo-3,4-dihydro-2H,8H-[1,4]-oxazepino[2,3,4-ij]quinoline-7-carboxamide;  
 N-(4-chlorobenzyl)-3-methyl-9-(morpholin-4-ylmethyl)-7-oxo-7H-[1,4]oxazino-[2,3,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-3-methyl-7-oxo-9-(tetrahydro-2H-pyran-4-ylmethyl)-7H-[1,4]-oxazino[2,3,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxypropyl)-3-methyl-7-oxo-7H-[1,4]oxazino[2,3,4-ij]-quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxyprop-1-ynyl)-3-methyl-7-oxo-7H-[1,4]oxazino [2,3,4-ij]quinoline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(morpholin-4-ylmethyl)-7-oxo-2-pyridin-3-yl-7H-[1,4]oxazino-[2,3,4-ij]quinoline-6-carboxamide;  
 2-benzyl-N-(4-chlorobenzyl)-10-(4-morpholinylmethyl)-3,8-dioxo-1,2,3,4-tetrahydro-8H-[1,4]diazepino[6,7,1-ij]quinoline-7-carboxamide;  
 N-(4-chlorobenzyl)-5-(3-hydroxypropyl)-4,7-dioxo-1,2-dihydro-4H,7H-imidazo-[1,2,3-ij][1,8]naphthyridine-8-carboxamide;  
 N-(4-chlorobenzyl)-5-(4-morpholinylmethyl)-4,7-dioxo-1,2-dihydro-4H,7H-imidazo-[1,2,3-ij][1,8]naphthyridine-8-carboxamide;  
 N-(4-chlorobenzyl)-5-(3-hydroxy-1-propynyl)-4,7-dioxo-1,2-dihydro-4H,7H-imidazo[1,2,3-ij][1,8]naphthyridine-8-carboxamide;  
 N-(4-chlorobenzyl)-6-(4-morpholinylmethyl)-3-oxo-9,10-dihydro-3H,8H-pyrido [3,2,1-ij]quinoline-2-carboxamide;  
 N-(4-chlorobenzyl)-3-methyl-9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide hydrobromide;  
 and pharmaceutically acceptable salts thereof.  
 
     
     
         41 . The compound according to  claim 40  which is selected from the group consisting of 
 N-(4-chlorobenzyl)-10-(4-morpholinylmethyl)-8-oxo-3,4-dihydro-2H,8H-[1,4]-oxazepino [2,3,4-ij]quinoline-7-carboxamide;  
 N-(4-chlorobenzyl)-8-(4-morpholinylmethyl)-2,6-dioxo-1,2-dihydro-6H-imidazo-[4,5,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-2-[(4-chlorobenzyl)amino]-9-(4-morpholinylmethyl)-7-oxo-3H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-2-(hydroxymethyl)-8-(3-hydroxy-1-propynyl)-6-oxo-1,2-dihydro-6H-pyrrolo[3,2, 1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-8-(3-hydroxyprop-1-ynyl)-2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamide;  
 N-(4-chlorobenzyl)-6-(morpholin-4-ylmethyl)-3-oxo-9,10-dihydro-3H,8H-pyrido-[3,2,1-ij]quinoline-2-carboxamide;  
 N-(4-chlorobenzyl)-3-methyl-9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide hydrobromide;  
 N-(4-chlorobenzyl)-10-(4-morpholinylmethyl)-2,8-dioxo-1,2,3,4-tetrahydro-8H-[1,4]diazepino[3,2,1-ij]quinoline-7-carboxamide;  
 2-(benzylamino)-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-3H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 2-benzyl-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]quinazoline-6-carboxamide;  
 2-benzyl-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-3,7-dioxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]quinazoline-6-carboxamide;  
 2-benzyl-N-(4-chlorobenzyl)-10-(4-morpholinylmethyl)-3,8-dioxo-1,2,3,4-tetrahydro-8H-[1,4]diazepino[6,7,1-ij]quinoline-7-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxyprop-1-ynyl)-3-methyl-7-oxo-2,3-dihydro-7H-[1,3,4]oxadiazino[6,5,4-ij]quinoline-6-carboxamide;  
 N-(4-Chlorobenzyl)-5-(3-hydroxyprop-1-ynyl)-1-methyl-7-oxo-2,3-dihydro-1H,7H-pyrido[3,2,1-ij]cinnoline-8-carboxamide;  
 and pharmaceutically acceptable salts thereof.  
 
     
     
         42 . The compound according to  claim 41  which is selected from the group consisting of 
 N-(4-chlorobenzyl)-10-(4-morpholinylmethyl)-8-oxo-3,4-dihydro-2H,8H-[1,4]-oxazepino [2,3,4-ij]quinoline-7-carboxamide;  
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-3-methyl-9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide hydrobromide;  
 N-(4-chlorobenzyl)-10-(4-morpholinylmethyl)-2,8-dioxo-1,2,3,4-tetrahydro-8H-[1,4]diazepino[3,2, 1-ij]quinoline-7-carboxamide;  
 2-(benzylamino)-N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-3H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-9-(3-hydroxy-1-propynyl)-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide;  
 and pharmaceutically acceptable salts thereof.  
 
     
     
         43 . The compound according to  claim 42  which is selected from the group consisting of 
 N-(4-chlorobenzyl)-9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido-[1,2,3-de]quinoxaline-6-carboxamide;  
 N-(4-chlorobenzyl)-3-methyl-9-(4-morpholinylmethyl)-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide hydrobromide;  
 and pharmaceutically acceptable salts thereof.  
 
     
     
         44 . A pharmaceutical composition comprising a compound of  claim 1  and a pharmaceutically acceptable carrier.  
     
     
         45 . A method of treating or preventing a viral infection, comprising administering to a mammal in need of such treatment, a compound of  claim 1 .  
     
     
         46 . The method according to  claim 45  wherein said viral infection is a herpes virus infection.  
     
     
         47 . The method according to  claim 45  wherein said mammal is a human.  
     
     
         48 . The method according to  claim 45  wherein said mammal is a livestock or companion animal.  
     
     
         49 . The method according to  claim 47  wherein the infection is herpes simplex virus type 1 or 2, human herpes virus type, 6, 7, or 8, varicella zoster virus, human cytomegalovirus, or Epstein-Barr virus.  
     
     
         50 . The method according to  claim 47  wherein the infection is herpes simplex virus type 1 or 2, human herpes virus type 8, varicella zoster virus, human cytomegalovirus, or Epstein-Barr virus.  
     
     
         51 . The method according to  claim 45  wherein the amount administered is from about 0.1 to about 300 mg/kg of body weight.  
     
     
         52 . The method according to  claim 51  wherein the amount administered is from about 1 to about 30 mg/kg of body weight.  
     
     
         53 . The method according to  claim 45  wherein the compound is administered parenterally, topically, intravaginally, orally, or rectally.  
     
     
         54 . A method for inhibiting a viral DNA polymerase, comprising contacting the polymerase with an effective inhibitory amount of a compound of  claim 1 .  
     
     
         55 . The method of  claim 54  wherein the polymerase and the compound are contacted in vitro.  
     
     
         56 . The method of  claim 54  wherein the polymerase and the compound are contacted in vivo.  
     
     
         57 . The compound of any one of  claim 1  for use in medical treatment.  
     
     
         58 . The compound of  claim 57  wherein the treatment is the treatment or prevention of a herpes viral infection.  
     
     
         59 . The use of a compound or composition of any one of  claim 1  to prepare a medicament for treating or preventing a herpes viral infection in a mammal.
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