US2004067877A1PendingUtilityA1

2', 3'-Dideoxynucleoside analogues for the treatment or prevention of Flaviviridae infections

Priority: Aug 1, 2002Filed: Aug 1, 2003Published: Apr 8, 2004
Est. expiryAug 1, 2022(expired)· nominal 20-yr term from priority
A61K 31/7072A61K 38/21C07H 19/06A61P 31/00A61K 38/2066A61K 31/58A61K 31/553A61K 31/513A61K 31/7068
56
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Claims

Abstract

A method for the treatment or prevention of Flaviviridae infections, in particular, hepatitis C virus infection, in a host, and in particular, a human, is provided that includes administering an effective amount of a β-L- or β-D-2′,3′-dideoxynucleoside or a pharmaceutically acceptable salt or prodrug thereof, optionally in a pharmaceutically acceptable diluent or excipient.

Claims

exact text as granted — not AI-modified
We claim  
     
         1 . A method for the treatment of an HCV infection in a host, comprising administering an effective treatment amount of a 2′,3′-dideoxynucleoside of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein 
 (i) X is O, S, S═O, SO 2 , NR 1 , N + R 1 R 2 , CH 2 , CHF and CR 3 R 4 ; 
 R 1  and R 2  are independently hydrogen, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, or C 3-8  cycloalkyl;  
 R 3  and R 4  are independently hydrogen, halogen (F, Cl, Br, or I), OH or OR 5 ;  
 R 5  is hydrogen or a hydroxyl-protecting group, such as alkyl, acyl or silyl;  
 
 (ii) Y is NH 2 , NHR 6 , NR 6 R 7 , OH or OR 8  
 each R 6 , R 7  and R 8  is independently H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, C 3-8  cycloalkyl, cyclopropyl, or C 2-6  acyl;  
 
 (iii) Z is chosen from hydrogen, halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; 
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl; and  
 
 (iv) R is hydrogen, phosphate; stabilized phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate; 
 R 10  is a C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, aryl, monophosphate, diphosphate, triphosphate, or —P(O)(OR 11 ) 2 ;  
 each R 11  is independently hydrogen, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl or a hydroxyl-protecting group;  
 optionally in a pharmaceutically acceptable carrier.  
 
 
     
     
         2 . The method of  claim 1 , wherein Z is not hydrogen.  
     
     
         3 . The method of  claim 1 , wherein Z is a halogen (F, Cl, Br, or I).  
     
     
         4 . The method of  claim 3 , wherein Z is F.  
     
     
         5 . The method of  claim 1 , wherein the 2′,3′-dideoxynucleoside is in the β-L-configuration.  
     
     
         6 . The method of  claim 5 , wherein the β-L-2′,3′-dideoxynucleoside is enantiomerically enriched.  
     
     
         7 . The method of  claim 5 , wherein the β-L-2′,3′-dideoxynucleoside is substantially free of the β-D-2′,3′-dideoxynucleoside.  
     
     
         8 . The method of  claim 5 , wherein the β-L-2′,3′-dideoxynucleoside is in isolated form.  
     
     
         9 . A method for the treatment of an HCV infection in a host, comprising administering an effective treatment amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein 
 Z′ is chosen from halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; and  
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl.  
 optionally in a pharmaceutically acceptable carrier.  
 
     
     
         10 . A method for the treatment of an HCV infection in a host, comprising administering an effective treatment amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein 
 (i) R 6  is H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, C 3-8  cycloalkyl, cyclopropyl, or C 2-6  acyl; and  
 (ii) R is hydrogen, phosphate; stabilized phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate;  
 (iii) Z′ is chosen from halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; and 
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl;  
 optionally in a pharmaceutically acceptable carrier.  
 
 
     
     
         11 . A method for the treatment of an HCV infection in a host, comprising administering an effective treatment amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.  
     
     
         12 . A method for the treatment of an HCV infection in a host, comprising administering an effective treatment amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, 
 (i) R 6  is H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, or C 3-8  cycloalkyl; and  
 (ii) R is hydrogen, phosphate; stabilized phosphate; acyl; —C(O)R 10 ; alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group which when administered in vivo is capable of providing a compound wherein R is H or phosphate;  
 optionally in a pharmaceutically acceptable carrier.  
 
     
     
         13 . The method of any one of claims  10 , wherein the β-L-2′,3′-dideoxynucleoside is enantiomerically enriched.  
     
     
         14 . The method of any one of claims  10 , wherein the β-L-2′,3′-dideoxynucleoside is substantially free of the β-D-2′,3′-dideoxynucleoside.  
     
     
         15 . The method of any one of claims  10 , wherein the β-L-2′,3′-dideoxynucleoside is in isolated form.  
     
     
         16 . A method for reducing the biological activity of a Flaviviridae viral infection in a host comprising administering an effective treatment amount of a 2′,3′-dideoxynucleoside of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein 
 (i) X is O, S, S═O, SO 2 , NR 1 , N + R 1 R 2 , CH 2 , CHF or CR 3 R 4 ; 
 R 1  and R 2  are independently hydrogen, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, or C 3-8  cycloalkyl;  
 R 3  and R 4  are independently hydrogen, halogen (F, Cl, Br, or I), OH or OR 5 ;  
 R 5  is hydrogen or a hydroxyl protecting group such as alkyl, acyl or silyl;  
 
 (ii) Y is NH 2 , NHR 6 , NR 6 R 7 , OH or OR 8  
 each R 6 , R 7  and R 8  is independently H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, C 3-8  cycloalkyl, cyclopropyl, or C 2-6  acyl;  
 
 (iii) Z is chosen from hydrogen, halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; 
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl; and  
 
 (iv) R is hydrogen, phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate; 
 R 10  is a C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, aryl, monophosphate, diphosphate, triphosphate, or —P(O)(OR 11 ) 2 ;  
 each R 11  is independently hydrogen, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl or a hydroxyl-protecting group;  
 optionally in a pharmaceutically acceptable carrier.  
 
 
     
     
         17 . The method of  claim 16 , wherein Z is not hydrogen.  
     
     
         18 . The method of  claim 16 , wherein Z is a halogen (F, Cl, Br, or I).  
     
     
         19 . The method of  claim 18 , wherein Z is F.  
     
     
         20 . The method of  claim 16 , wherein the 2′,3′-dideoxynucleoside is in the β-L-configuration.  
     
     
         21 . A method for reducing the biological activity of a Flaviviridae viral infection in a host comprising administering an effective treatment amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein 
 Z′ is chosen from halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; and  
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl.  
 optionally in a pharmaceutically acceptable carrier.  
 
     
     
         22 . A method for reducing the biological activity of a Flaviviridae viral infection in a host comprising administering an effective treatment amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein 
 (i) R 6  is H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, C 3-8  cycloalkyl, cyclopropyl, or C 2-6  acyl; and  
 (ii) R is hydrogen, phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate;  
 (iii) Z′ is chosen from halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; and 
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl;  
 optionally in a pharmaceutically acceptable carrier.  
 
 
     
     
         23 . A method for reducing the biological activity of a Flaviviridae viral infection in a host comprising administering an effective treatment amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.  
     
     
         24 . A method for reducing the biological activity of a Flaviviridae viral infection in a host comprising administering an effective treatment amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, 
 (i) R 6  is H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, or C 3-8  cycloalkyl; and  
 (ii) R is hydrogen, phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate;  
 optionally in a pharmaceutically acceptable carrier.  
 
     
     
         25 . The method according to  claim 16 , wherein the Flaviviridae viral infection is an HCV infection.  
     
     
         26 . The method according to any one of claims  1  or  16 , further comprising administering in combination and/or alternation one or more other antiviral agent(s).  
     
     
         27 . The method according to  claim 26 , wherein the antiviral agent is selected from the group consisting of ribavirin, interferon, PEGASYS (pegylated interferon alfa-2a), INFERGEN (interferon alfacon-1), OMNIFERON (natural interferon), ALBUFERON, REBIF (interferon beta-1a), Omega Interferon, Oral Interferon Alpha, Interferon gamma-1b, Interleukin-10, IP-501, Merimebodib VX-497, AMANTADINE (Symmetrel), HEPTAZYME, IDN-6556, XTL-002, HCV/MF59, CIVACIR, LEVOVIRIN, VIRAMIDINE, ZADAXIN (thymosin alfa-1), CEPLENE (histamine dihydrochloride), VX 950/LY 570310, ISIS 14803, IDN-6556 and JTK 003.  
     
     
         28 . The method according to any one of claims  1  or  16 , wherein the host is a human.  
     
     
         29 . The method according to any one of claims  1  or  16 , wherein the host is also infected with HIV and/or HBV.  
     
     
         30 . The method according to  claim 29 , wherein the host is a human.  
     
     
         31 . A pharmaceutical composition for the treatment and/or prophylaxis of an HCV infection in a host, comprising an effective treatment amount of a 2′,3′-dideoxynucleoside of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, wherein 
 (i) X is O, S, S═O, SO 2 , NR 1 , N + R 1 R 2 , CH 2 , CHF or CR 3 R 4 ; 
 R 1  and R 2  are independently hydrogen, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, or C 3-8  cycloalkyl;  
 R 3  and R 4  are independently hydrogen, halogen (F, Cl, Br, or I), OH or OR 5 ;  
 R 5  is hydrogen or a hydroxyl protecting group such as alkyl, acyl or silyl;  
 
 (ii) Y is NH 2 , NHR 6 , NR 6 R 7 , OH or OR 8  
 each R 6 , R 7  and R 7  is independently H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, C 3-8  cycloalkyl, cyclopropyl, or C 2-6  acyl;  
 
 (iii) Z is chosen from hydrogen, halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; 
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl; and  
 
 (iv) R is hydrogen, phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate; 
 R 10  is a C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, aryl, monophosphate, diphosphate, triphosphate, or —P(O)(OR 11 ) 2 ;  
 each R 11  is independently hydrogen, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl or a hydroxyl-protecting group;  
 together with pharmaceutically acceptable carrier.  
 
 
     
     
         32 . The pharmaceutical composition of  claim 31 , wherein Z is not hydrogen.  
     
     
         33 . The pharmaceutical composition of  claim 31 , wherein Z is a halogen (F, Cl, Br, or I).  
     
     
         34 . The pharmaceutical composition of  claim 33 , wherein Z is F.  
     
     
         35 . The pharmaceutical composition of  claim 31 , wherein the 2′,3′-dideoxynucleoside is in the β-L-configuration.  
     
     
         36 . The pharmaceutical composition of  claim 35 , wherein the β-L-2′,3′-dideoxynucleoside is enantiomerically enriched.  
     
     
         37 . The pharmaceutical composition of  claim 35 , wherein the β-L-2′,3′-dideoxynucleoside is substantially free of the β-D-2′,3′-dideoxynucleoside.  
     
     
         38 . The pharmaceutical composition of  claim 35 , wherein the β-L-2′,3′-dideoxynucleoside is in isolated form.  
     
     
         39 . A pharmaceutical composition for the treatment and/or prophylaxis of an HCV infection in a host, comprising an effective amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, wherein 
 Z′ is chosen from halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; and  
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl.  
 together with a pharmaceutically acceptable carrier.  
 
     
     
         40 . A pharmaceutical composition for the treatment and/or prophylaxis of an HCV infection in a host, comprising an effective amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, wherein 
 (i) R 6  is H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, C 3-8  cycloalkyl, cyclopropyl, or C 2-6  acyl; and  
 (ii) R is hydrogen, phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate;  
 (iii) Z′ is chosen from halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; and 
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl;  
 together with a pharmaceutically acceptable carrier.  
 
 
     
     
         41 . A pharmaceutical composition for the treatment and/or prophylaxis of an HCV infection in a host, comprising an effective amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, together with a pharmaceutically acceptable carrier.  
     
     
         42 . A pharmaceutical composition for the treatment and/or prophylaxis of an HCV infection in a host, comprising an effective amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, 
 (i) R 6  is H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, or C 3-8  cycloalkyl; and  
 (ii) R is hydrogen, phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate;  
 together with a pharmaceutically acceptable carrier.  
 
     
     
         43 . The pharmaceutical composition of any one of claims  40 , wherein the β-L-2′,3′-dideoxynucleoside is enantiomerically enriched.  
     
     
         44 . The pharmaceutical composition of any one of claims  40 , wherein the β-L-2′,3′-dideoxynucleoside is substantially free of the β-D-2′,3′-dideoxynucleoside.  
     
     
         45 . The pharmaceutical composition of any one of claims  40 , wherein the β-L-2′,3′-dideoxynucleoside is in an isolated form.  
     
     
         46 . A pharmaceutical composition for reducing the biological activity of a Flaviviridae viral infection in a host comprising an effective amount of a 2′,3′-dideoxynucleoside of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, wherein 
 (i) X is O, S, S═O, SO 2 , NR 1 , N + R 1 R 2 , CH 2 , CHF or CR 3 R 4 ; 
 R 1  and R 2  are independently hydrogen, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, or C 3-8  cycloalkyl;  
 R 3  and R 4  are independently hydrogen, halogen (F, Cl, Br, or I), OH or OR 5 ;  
 R 5  is hydrogen or a hydroxyl protecting group such as alkyl, acyl or silyl;  
 
 (ii) Y is NH 2 , NHR 6 , NR 6 R 7 , OH or OR 8  
 each R 6 , R 7  and R 7  is independently H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, C 3-8  cycloalkyl, cyclopropyl, or C 2-6  acyl;  
 
 (iii) Z is chosen from hydrogen, halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; 
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl; and  
 
 (iv) R is hydrogen, phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate; 
 R 10  is a C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, aryl, monophosphate, diphosphate, triphosphate, or —P(O)(OR 11 ) 2 ;  
 each R 11  is independently hydrogen, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl or a hydroxyl-protecting group;  
 together with a pharmaceutically acceptable carrier.  
 
 
     
     
         47 . The pharmaceutical composition of  claim 46 , wherein Z is not hydrogen.  
     
     
         48 . The pharmaceutical composition of  claim 46 , wherein Z is a halogen (F, Cl, Br, or I).  
     
     
         49 . The pharmaceutical composition of  claim 48 , wherein Z is F.  
     
     
         50 . The pharmaceutical composition of  claim 46 , wherein the 2′,3′-dideoxynucleoside is in the β-L-configuration.  
     
     
         51 . A pharmaceutical composition for reducing the biological activity of a Flaviviridae viral infection in a host comprising an effective amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, wherein 
 Z′ is chosen from halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; and  
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl.  
 together with a pharmaceutically acceptable carrier.  
 
     
     
         52 . A pharmaceutical composition for reducing the biological activity of a Flaviviridae viral infection in a host comprising an effective amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, wherein 
 (i) R 6  is H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, C 3-8  cycloalkyl, cyclopropyl, or C 2-6  acyl; and  
 (ii) R is hydrogen, phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate;  
 (iii) Z′ is chosen from halogen (F, Cl, Br, or I), C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, CN, CF 3 , N 3 , NO 2 , aryl, heteroaryl and COR 9 ; and 
 R 9  is chosen from H, OH, SH, C 1-6  alkyl, C 1-6  aminoalkyl, C 1-6  alkoxy and C 1-6  thioalkyl;  
 together with a pharmaceutically acceptable carrier.  
 
 
     
     
         53 . A pharmaceutical composition for reducing the biological activity of a Flaviviridae viral infection in a host comprising an effective amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, together with a pharmaceutically acceptable carrier.  
     
     
         54 . A pharmaceutical composition for reducing the biological activity of a Flaviviridae viral infection in a host comprising an effective amount of a compound of the formula:  
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt or prodrug thereof, 
 (i) R 6  is H, C 1-6  alkyl, C 2-6  alkenyl, C 2-6  alkynyl, or C 3-8  cycloalkyl; and  
 (ii) R is hydrogen, phosphate; acyl; —C(O)R 10 , alkyl; sulfonate ester; sulfonyl; a lipid; an amino acid; a carbohydrate; a peptide; a cholesterol; or other pharmaceutically acceptable leaving group, which, when administered in vivo, is capable of providing a compound wherein R is H or phosphate;  
 together with a pharmaceutically acceptable carrier.  
 
     
     
         55 . The pharmaceutical composition according to  claim 52 , wherein the Flaviviridae viral infection is an HCV infection.  
     
     
         56 . The pharmaceutical composition according to any one of claims  31  or  46 , further comprising one or more other antiviral agent(s).  
     
     
         57 . The pharmaceutical composition according to  claim 56 , wherein the antiviral agent is selected from the group consisting of ribavirin, interferon, PEGASYS (pegylated interferon alfa-2a), INFERGEN (interferon alfacon-1), OMNIFERON (natural interferon), ALBUFERON, REBIF (interferon beta-1a), Omega Interferon, Oral Interferon Alpha, Interferon gamma-1b, Interleukin-10, IP-501, Merimebodib VX-497, AMANTADINE (Symmetrel), HEPTAZYME , IDN-6556, XTL-002, HCV/MF59, CIVACIR, LEVOVIRIN, VIRAMIDINE, ZADAXIN (thymosin alfa-1), CEPLENE (histamine dihydrochloride), VX 950/LY 570310, ISIS 14803, IDN-6556 and JTK 003.  
     
     
         58 . The pharmaceutical composition according to any one of claims  31  or  46 , wherein the host is a human.  
     
     
         59 . The pharmaceutical composition according to any one of claims  32  or  46 , wherein the host is also infected with HIV and/or HBV.  
     
     
         60 . The pharmaceutical composition according to  claim 59 , wherein the host is a human.

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