US2004180910A1PendingUtilityA1

Heterocycle carboxamides as antiviral agents

52
Priority: Jul 12, 2000Filed: Mar 29, 2004Published: Sep 16, 2004
Est. expiryJul 12, 2020(expired)· nominal 20-yr term from priority
A61P 31/22A61P 31/20A61P 31/12A61P 43/00C07D 217/26C07D 405/06C07D 217/14C07D 471/04
52
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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 1-7 alkyl which 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, aryl, or heteroaryl;  
 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 morpholine which may be optionally substituted by aryl or C 1-7 alkyl;  
 W is a heterocycle of formula W1, W3, or W4;  
                     
 A is CR 4  or nitrogen;  
 B is CR 5  or nitrogen;  
 C is CR 6  or nitrogen;  
 E and F are such that (a) one is oxygen and the other is C(═O); or 
 (b) E is C(═O) and F is NR 7 ;  
 
 J and K are such that (a) J is nitrogen and K is CR 8 ; or 
 (b) J is CR 6  and K is nitrogen;  
 
 with the provisos that when W is of formula W3 and J is nitrogen, then at least one of  
 A and B is nitrogen;  
 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 6  is (a) H, 
 (b) halo,  
 (c) aryl,  
 (d) het,  
 (e) OR 12 ,  
 (f) SR 12 ,  
 (g) 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 , aryl, halo, C 3-8 cycloalkyl optionally substituted by OR 12 , or het attached through a carbon atom,  
 (h) NR 10 R 11 ,  
 (i) 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 ,  
 (j) (C═O)R 9 ,  
 (k) S(O) m R 9 ,  
 (l) (C═O)OR 2 ,  
 (m) NHSO 2 R 9 ,  
 (n) nitro, or  
 (o) 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, or  
 (e) het;  
 
 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, 
 (b) NR 10 R 11 ,  
 (c) aryl, or  
 (d) 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, het, 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 ;  
 
 each m is independently 1 or 2;  
 aryl is a phenyl radical or an ortho-fused bicyclic carbocyclic radical wherein at least one ring is aromatic, and aryl maybe 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 a pharmaceutically acceptable salt 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 W1.2.  
     
     
         5 . A compound of  claim 2  wherein W is of the formula W1.3.  
     
     
         6 . A compound of  claim 2  wherein W is of the formula W1.4.  
     
     
         7 . A compound of  claim 2  wherein W is of the formula W1.5.  
     
     
         8 . A compound of  claim 2  wherein W is of the formula W1.6.  
     
     
         9 . A compound of  claim 2  wherein W is of the formula W1.7.  
     
     
         10 . A compound of  claim 2  wherein W is of the formula W1.8.  
     
     
         11 . A compound of  claim 2  wherein W is of the formula W1.9.  
     
     
         12 . A compound of  claim 2  wherein W is of the formula W1.10.  
     
     
         13 . A compound of  claim 2  wherein W is of the formula W1.11.  
     
     
         14 . A compound of  claim 2  wherein W is of the formula W1.12.  
     
     
         15 . A compound of  claim 2  wherein W is of the formula W1.13.  
     
     
         16 . A compound of  claim 2  wherein W is of the formula W1.14.  
     
     
         17 . A compound of  claim 2  wherein W is of the formula W1.15.  
     
     
         18 . A compound of  claim 2  wherein W is of the formula W1.16.  
     
     
         19 . A compound of  claim 2  wherein W is of the formula W1.17.  
     
     
         20 . A compound of  claim 2  wherein W is of the formula W1.18.  
     
     
         21 . A compound of  claim 2  wherein W is of the formula W1.19.  
     
     
         22 . A compound of  claim 2  wherein W is of the formula W1.20.  
     
     
         23 . A compound of  claim 2  wherein W is of the formula W1.21.  
     
     
         24 . A compound of  claim 2  wherein W is of the formula W1.22.  
     
     
         25 . A compound of  claim 2  wherein W is of the formula W1.23.  
     
     
         26 . A compound of  claim 1  wherein W is of the formula W3.  
     
     
         27 . A compound of  claim 26  wherein W is of the formula W3.1.  
     
     
         28 . A compound of  claim 26  wherein W is of the formula W3.2.  
     
     
         29 . A compound of  claim 26  wherein W is of the formula W3.3.  
     
     
         30 . A compound of  claim 26  wherein W is of the formula W3.4.  
     
     
         31 . A compound of  claim 26  wherein W is of the formula W3.5.  
     
     
         32 . A compound of  claim 26  wherein W is of the formula W3.6.  
     
     
         33 . A compound of  claim 26  wherein W is of the formula W3.7.  
     
     
         34 . A compound of  claim 26  wherein W is of the formula W3.8.  
     
     
         35 . A compound of  claim 26  wherein W is of the formula W3.9.  
     
     
         36 . A compound of  claim 26  wherein W is of the formula W3.10.  
     
     
         37 . A compound of  claim 26  wherein W is of the formula W3.11.  
     
     
         38 . A compound of  claim 26  wherein W is of the formula W3.12.  
     
     
         39 . A compound of  claim 26  wherein W is of the formula W3.13.  
     
     
         40 . A compound of  claim 26  wherein W is of the formula W3.14.  
     
     
         41 . A compound of  claim 1  wherein W is of-the formula W4.  
     
     
         42 . The compound according to  claim 1 , wherein X is Cl.  
     
     
         43 . The compound according to  claim 1  wherein G is 4-morpholinylmethyl.  
     
     
         44 . The compound according to  claim 1  wherein G is 3-hydroxy-1-propynyl.  
     
     
         45 . The compound according to  claim 1  wherein G is tetrahydro-2H-pyran-4-ylmethyl.  
     
     
         46 . The compound according to  claim 1  which is 
 N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-2-oxo-2H-pyrano[2,3-c]pyridine-3-carboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-1-oxo-1H-isochromene-3-carboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-1-oxo-6-(tetrahydro-2H-pyran-4-ylmethyl)-1H-isochromene-3-carboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-1-oxo-1H-isochromene-3-carboxamide;  
 N-(4-chlorobenzyl)-5-hydroxy-3-(3-hydroxy-1-propynyl)-8-oxo-7,8-dihydro[1,7]-naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-1-oxo-1,2-dihydro-3-isoquinolinecarboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-1-oxo-1,2-dihydro-3-isoquinolinecarboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)[1,7]naphthyridine-3-carboxamide;  
 N-(4-chlorobenzyl)-8-ethoxy-4-hydroxy-6-(3-hydroxy-1-propynyl)[1,7]-naphthyridine-3-carboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)[1,7]naphthyridine-3-carboxamide;  
 N-(4-chlorobenzyl)-8-ethoxy-4-hydroxy-6-(4-morpholinylmethyl)[1,7]naphthyridine-3-carboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)[1,5]naphthyridine-3-carboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)[1,5]naphthyridine-3-carboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(tetrahydro-2H-pyran-4-ylmethyl)[1,5]-naphthyridine-3-carboxamide;  
 N-(4-chlorobenzyl)-8-hydroxy-2-(3-hydroxy-1-propynyl)pyrido[3,2-d]pyrimidine-7-carboxamide;  
 N-(4-chlorobenzyl)-8-hydroxy-2-(4-morpholinylmethyl)pyrido[3,2-d]pyrimidine-7-carboxamide;  
 N-(4-chlorobenzyl)-5-hydroxy-3-(4-morpholinylmethyl)[1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-5-hydroxy-3-(3-hydroxy-1-propynyl)[1,7]naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-5-hydroxy-3-(tetrahydro-2H-pyran-4-ylmethyl)[1,7]-naphthyridine-6-carboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-isoquinolinecarboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-isoquinolinecarboxamide;  
 N-(4-chlorobenzyl)-4-hydroxy-6-(tetrahydro-2H-pyran-4-ylmethyl)-3-isoquinoline-carboxamide; or  
 a pharmaceutically acceptable salt thereof.  
 
     
     
         47 . A pharmaceutical composition comprising a compound of  claim 1  and a pharmaceutically acceptable carrier.  
     
     
         48 . A method of treating or preventing a viral infection, comprising administering to a mammal in need of such treatment, a compound of formula (I),  
       
         
           
           
               
               
           
         
       
       wherein, 
 X is Cl, Br, F, CN or NO 2 ;  
 G is (a) C 3-7 alkyl which is partially unsaturated and is substituted by hydroxy, 
 (b) C 1-7 alkyl which is fully saturated and is substituted by hydroxy, or  
 (c) 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, aryl, or heteroaryl;  
 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 morpholine which may be optionally substituted by aryl or C 1-7 alkyl;  
 W is a heterocycle of formula W1, W3, or W4;  
                     
 A is CR 4  or nitrogen;  
 B is CR 5  or nitrogen;  
 C is CR 6  or nitrogen;  
 E and F are such that (a) one is oxygen and the other is C(═O); or 
 (b) E is C(═O) and F is NR 7 ;  
 
 J and K are such that (a) J is nitrogen and K is CR 8 ; or 
 (b) J is CR 6  and K is nitrogen;  
 
 with the provisos that when W is of formula W3 and J is nitrogen, then at least one of  
 A and B is nitrogen;  
 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 6  is (a) H, 
 (b) halo,  
 (c) aryl,  
 (d) het,  
 (e) OR 12 ,  
 (f) SR 12 ,  
 (g) 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 , aryl, halo, C 3-8 cycloalkyl optionally substituted by OR 12 , or het attached through a carbon atom,  
 (h) NR 10 R 11 ,  
 (i) 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 ,  
 (j) (C═O)R 9 ,  
 (k) S(O) m R 9 ,  
 (l) (C═O)OR 2 ,  
 (m) NHSO 2 R 9 ,  
 (n) nitro, or  
 (o) 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, or  
 (e) het;  
 
 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, 
 (b) NR 10 R 11 ,  
 (c) aryl, or  
 (d) 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, het, 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 ;  
 
 each m is independently 1 or 2;  
 aryl is a phenyl radical or an ortho-fused bicyclic carbocyclic radical wherein at least one ring is aromatic, and aryl maybe 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 a pharmaceutically acceptable salt thereof;  
 
     
     
         49 . The method according to  claim 48  wherein said viral infection is a herpes virus infection.  
     
     
         50 . The method according to  claim 48  wherein said mammal is a human.  
     
     
         51 . The method according to  claim 48  wherein said mammal is a food animal or companion animal.  
     
     
         52 . The method according to  claim 48  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.  
     
     
         53 . The method according to  claim 48  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.  
     
     
         54 . The method according to  claim 48  wherein the amount administered is from about 0.1 to about 300 mg/kg of body weight.  
     
     
         55 . The method according to  claim 48  wherein the amount administered is from about 1 to about 30 mg/kg of body weight.  
     
     
         56 . The method according to  claim 48  wherein the compound is administered parenterally, topically, intravaginally, orally, or rectally.  
     
     
         57 . A method for inhibiting a viral DNA polymerase, comprising contacting the polymerase with an effective inhibitory amount of a compound of the formula (I)  
       
         
           
           
               
               
           
         
       
       wherein, 
 X is Cl, Br, F, CN or NO 2 ;  
 G is (a) C 3-7 alkyl which is partially unsaturated and is substituted by hydroxy, 
 (b) C 1-7 alkyl which is fully saturated and is substituted by hydroxy, or  
 (c) 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, aryl, or heteroaryl;  
 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 morpholine which may be optionally substituted by aryl or C 1-7 alkyl;  
 W is a heterocycle of formula W1, W3, or W4;  
                     
 A is CR 4  or nitrogen;  
 B is CR 5  or nitrogen;  
 C is CR 6  or nitrogen;  
 E and F are such that (a) one is oxygen and the other is C(═O); or 
 (b) E is C(═O) and F is NR 7 ;  
 
 J and K are such that (a) J is nitrogen and K is CR 8 ; or 
 (b) J is CR 6  and K is nitrogen;  
 
 with the provisos that when W is of formula W3 and J is nitrogen, then at least one of  
 A and B is nitrogen;  
 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 -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 9 ,  
 (j) NHSO 2 R 9 ,  
 (k) nitro, or  
 (l) cyano;  
 
 R 6  is (a) H, 
 (b) halo,  
 (c) aryl,  
 (d) het,  
 (e) OR 12 ,  
 (f) SR 12 ,  
 (g) 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 , aryl, halo, C 3-8 cycloalkyl optionally substituted by OR 12 , or het attached through a carbon atom,  
 (h) NR 10 R 11 ,  
 (i) 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 ,  
 (j) (C═O)R 9 ,  
 (k) S(O) m R 9 ,  
 (l) (C═O)OR 9 ,  
 (m) NHSO 2 R 9 ,  
 (n) nitro, or  
 (o) 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, or  
 (e) het;  
 
 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, 
 (b) NR 10 R 11 ,  
 (c) aryl, or  
 (d) 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 -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 2  is (a) H, 
 (b) aryl,  
 (c) het  
 (d) C 1-7 alkyl optionally substituted by aryl, het, 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 ;  
 
 each m is independently 1 or 2;  
 aryl is a phenyl radical or an ortho-fused bicyclic carbocyclic radical wherein at least one ring is aromatic, and aryl maybe 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 a pharmaceutically acceptable salt thereof;  
 
     
     
         58 . The method of  claim 57  wherein the polymerase and the compound are contacted in vitro.  
     
     
         59 . The method of  claim 57  wherein the polymerase and the compound are contacted in vivo.

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