US2017128444A1PendingUtilityA1

Polycyclic-carbamoylpyridone compounds and their pharmaceutical use

Assignee: GILEAD SCIENCES INCPriority: Jul 12, 2013Filed: Sep 6, 2016Published: May 11, 2017
Est. expiryJul 12, 2033(~7 yrs left)· nominal 20-yr term from priority
A61P 31/18A61P 31/00C07D 471/14A61K 31/4985C07D 471/18
60
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Claims

Abstract

Compounds for use in the treatment of human immunodeficiency virus (HIV) infection are disclosed. The compounds have the following Formula (I): including stereoisomers and pharmaceutically acceptable salts thereof, wherein L, R 5 , W, X, Y 1 , Y 2 , and Z are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A method of treating an HIV infection in a human having or at risk of having an HIV infection by administering to the human a therapeutically effective amount of a compound having the following Formula (I): 
       
         
           
           
               
               
           
         
       
       or a stereoisomer or pharmaceutically acceptable salt thereof,
 wherein:
 Y 1  and Y 2  are each, independently, hydrogen, C 1-3 alkyl or C 1-3 haloalkyl; 
 R 1  is phenyl substituted with one to three halogens; 
 X is —CHR 2 —; 
 W is a bond; 
 Z is —CHR 4 —; 
 R 2  and R 4  are each, independently, hydrogen or C 1-3 alkyl; 
 R 5  is hydrogen, C 1-3 alkyl or C 1-3 haloalkyl; 
 L is —C(R a ) 2 C(R a ) 2 C(R a ) 2 —; and 
 each R a  is, independently, hydrogen, halo, hydroxy or C 1-4 alkyl. 
 
 
     
     
         2 - 6 . (canceled) 
     
     
         7 . The method of  claim 1  wherein the compound of Formula I is represented by Formula (IV): 
       
         
           
           
               
               
           
         
       
     
     
         8 . The method of  claim 7  wherein the compound of Formula I is represented by Formula (IV-A): 
       
         
           
           
               
               
           
         
       
     
     
         9 - 11 . (canceled) 
     
     
         12 . The method of  claim 1  wherein each R a  is hydrogen. 
     
     
         13 . The method of  claim 1  wherein R 1  is substituted with one halogen. 
     
     
         14 . The method of  claim 13  wherein R 1  is 4-fluorophenyl or 2-fluorophenyl. 
     
     
         15 . The method of  claim 1  wherein R 1  is substituted with two halogens. 
     
     
         16 . The method of  claim 15  wherein R 1  is 2,4-difluorophenyl, 2,3-difluorophenyl, 2,6-difluorophenyl, 3-fluoro-4-chlorophenyl, 3,4-difluorophenyl, 2-fluoro-4-chlorophenyl, or 3,5-difluorophenyl. 
     
     
         17 . The method of  claim 15  wherein R 1  is 2,4-difluorophenyl, 2,3-difluorophenyl, 2,6-difluorophenyl, 3-fluoro-4-chlorophenyl, 3,4-difluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, or 3,5-difluorophenyl. 
     
     
         18 . The method of  claim 16  wherein R 1  is 2,4-difluorophenyl. 
     
     
         19 . The method of  claim 1  wherein R 1  is substituted with three halogens. 
     
     
         20 . The method of  claim 19  wherein R 1  is 2,4,6-trifluorophenyl or 2,3,4-trifluorophenyl. 
     
     
         21 . The method of  claim 20  wherein R 1  is 2,4,6-trifluorophenyl. 
     
     
         22 . The method of  claim 1  wherein R 5  is hydrogen or C 1-3 alkyl. 
     
     
         23 . The method of  claim 1  wherein R 5  is hydrogen. 
     
     
         24 . The method of  claim 1  wherein R 5  is methyl. 
     
     
         25 . The method of  claim 1  wherein the compound is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         26 - 30 . (canceled) 
     
     
         31 . A method of inhibiting integrase activity in a human comprising administering to the human a therapeutically effective amount of a compound having the following Formula (I): 
       
         
           
           
               
               
           
         
       
       or a stereoisomer or pharmaceutically acceptable salt thereof,
 wherein:
 Y 1  and Y 2  are each, independently, hydrogen, C 1-3 alkyl or C 1-3 haloalkyl; 
 R 1  is phenyl substituted with one to three halogens; 
 X is —CHR 2 —; 
 W is a bond; 
 Z is —CHR 4 —; 
 R 2  and R 4  are each, independently, hydrogen or C 1-3 alkyl; 
 R 5  is hydrogen, C 1-3 alkyl or C 1-3 haloalkyl; 
 L is —C(R a ) 2 C(R a ) 2 C(R a ) 2 —; and 
 each R a  is, independently, hydrogen, halo, hydroxy or C 1-4 alkyl. 
 
 
     
     
         32 . The method of  claim 31  wherein the human is infected with human immunodeficiency virus. 
     
     
         33 . The method of  claim 32  wherein the compound of Formula I is represented by Formula (IV): 
       
         
           
           
               
               
           
         
       
     
     
         34 . The method of  claim 33  wherein the compound of Formula I is represented by Formula (IV-A): 
       
         
           
           
               
               
           
         
       
     
     
         35 . The method of  claim 32  wherein each R a  is hydrogen. 
     
     
         36 . The method of  claim 32  wherein R 1  is substituted with one halogen. 
     
     
         37 . The method of  claim 36  wherein R 1  is 4-fluorophenyl or 2-fluorophenyl. 
     
     
         38 . The method of  claim 32  wherein R 1  is substituted with two halogens. 
     
     
         39 . The method of  claim 38  wherein R 1  is 2,4-difluorophenyl, 2,3-difluorophenyl, 2,6-difluorophenyl, 3-fluoro-4-chlorophenyl, 3,4-difluorophenyl, 2-fluoro-4-chlorophenyl, or 3,5-difluorophenyl. 
     
     
         40 . The method of  claim 38  wherein R 1  is 2,4-difluorophenyl, 2,3-difluorophenyl, 2,6-difluorophenyl, 3-fluoro-4-chlorophenyl, 3,4-difluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, or 3,5-difluorophenyl. 
     
     
         41 . The method of  claim 39  wherein R 1  is 2,4-difluorophenyl. 
     
     
         42 . The method of  claim 32  wherein R 1  is substituted with three halogens. 
     
     
         43 . The method of  claim 42  wherein R 1  is 2,4,6-trifluorophenyl or 2,3,4-trifluorophenyl. 
     
     
         44 . The method of  claim 43  wherein R 1  is 2,4,6-trifluorophenyl. 
     
     
         45 . The method of  claim 32  wherein R 5  is hydrogen or C 1-3 alkyl. 
     
     
         46 . The method of  claim 32  wherein R 5  is hydrogen. 
     
     
         47 . The method of  claim 32  wherein R 5  is methyl. 
     
     
         48 . The method of  claim 32  wherein the compound is selected from:

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