US2021040049A1PendingUtilityA1

Anti-hcmv compositions and methods

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Assignee: EVRYS BIO LLCPriority: Nov 10, 2014Filed: Jun 21, 2020Published: Feb 11, 2021
Est. expiryNov 10, 2034(~8.3 yrs left)· nominal 20-yr term from priority
Y02A50/30C07D 241/44A61K 31/4035C07D 209/04C07D 215/40C07C 235/38C07C 217/62A61K 31/522A61K 31/47A61P 31/12C07D 209/08A61P 31/20
54
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Claims

Abstract

This document relates to compounds useful as agents for preventing or treating human cytomegalovirus (HCMV) infections.

Claims

exact text as granted — not AI-modified
1 . A composition comprising a compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         X is NH or O, provided that when m is 1, X is NH; 
         R 1  and R 2  are independently selected from H, halo, lower straight chain or branched alkyl, and OR 6 ; 
         R 3 , R 4 , and R 5  are independently selected from H, halo, —CN, lower straight chain or branched alkyl, and OR 6 ; 
         each R 6  is independently selected from H, lower straight chain or branched alkyl; 
         m is 0 or 1; 
         n is 0, 1, 2 or 3, provided that when m is 1, n is not 3; and 
         Ar is 
       
       
         
           
           
               
               
           
         
         substituted with 0, 1 or 2 groups independently selected from halo, —CN, lower straight chain or branched alkyl and wherein:
 R 9  is selected from H, lower straight chain or branched alkyl, —C(O)R 10  or —SO 2 R 10  and R 10  is selected from lower straight chain or branched alkyl 
 
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         2 . The composition of  claim 1 , wherein Ar is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein: 
         R 8  is selected from H, halo and —CN; 
         R 9  is selected from H, lower straight chain or branched alkyl, —C(O)R 10  or —SO 2 R 10  and R 10  is selected from lower straight chain or branched alkyl. 
       
     
     
         3 . The composition of  claim 2 , wherein at least one of R 3 , R 4 , or R 5  is in the ortho position and selected from the group consisting of halo, —CN, a straight chain or branched alkyl of 1 to 4 carbon atoms, and a straight or branched alkoxy of 1 to 4 carbon atoms. 
     
     
         4 . The composition of  claim 2 , wherein at least two of R 3 , R 4 , or R 5  is in the ortho position and selected from the group consisting of halo, —CN, a straight chain or branched alkyl of 1 to 4 carbon atoms, and a straight or branched alkoxy of 1 to 4 carbon atoms. 
     
     
         5 . The composition of  claim 2 , wherein R 2  is selected from halo, lower straight chain or branched alkyl, and OR 6 . 
     
     
         6 . The composition of  claim 2 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and pharmaceutically acceptable salts thereof. 
     
     
         7 . A pharmaceutical composition comprising a compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         X is NH or O, provided that when m is 1, X is NH; 
         R 1  and R 2  are independently selected from H, halo, lower straight chain or branched alkyl, and OR 6 ; 
         R 3 , R 4 , and R 5  are independently selected from H, halo, —CN, lower straight chain or branched alkyl, and OR 6 ; 
         each R 6  is independently selected from H, lower straight chain or branched alkyl; 
         m is 0 or 1; 
         n is 0, 1, 2 or 3, provided that when m is 1, n is not 3; and 
         Ar is 
       
       
         
           
           
               
               
           
         
         substituted with 0, 1 or 2 groups independently selected from halo, —CN, lower straight chain or branched alkyl and wherein:
 R 9  is selected from H, lower straight chain or branched alkyl, —C(O)R 10  or —SO 2 R 10  and R 10  is selected from lower straight chain or branched alkyl, 
 
         or a pharmaceutically acceptable salt thereof, and 
         a pharmaceutically acceptable carrier. 
       
     
     
         8 . The pharmaceutical composition of  claim 7 , wherein Ar is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein: 
         R 8  is selected from H, halo and —CN; 
         R 9  is selected from H, lower straight chain or branched alkyl, —C(O)R 10  or —SO 2 R 10  and R 10  is selected from lower straight chain or branched alkyl. 
       
     
     
         9 . The pharmaceutical composition of  claim 8 , wherein at least one of R 3 , R 4 , or R 5  is in the ortho position and selected from the group consisting of halo, —CN, a straight chain or branched alkyl of 1 to 4 carbon atoms, and a straight or branched alkoxy of 1 to 4 carbon atoms. 
     
     
         10 . The pharmaceutical composition of  claim 8 , wherein at least two of R 3 , R 4 , or R 5  is in the ortho position and selected from the group consisting of halo, —CN, a straight chain or branched alkyl of 1 to 4 carbon atoms, and a straight or branched alkoxy of 1 to 4 carbon atoms. 
     
     
         11 . The pharmaceutical composition of  claim 8 , wherein R 2  is selected from halo, lower straight chain or branched alkyl, and OR 6 . 
     
     
         12 . The pharmaceutical composition of  claim 8 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and pharmaceutically acceptable salts thereof. 
     
     
         13 . A method for treating or preventing an HCMV infection in a subject, the method comprising administering to the subject a therapeutically effective amount of a compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         X is NH or O, provided that when m is 1, X is NH; 
         R 1  and R 2  are independently selected from H, halo, lower straight chain or branched alkyl, and OR 6 ; 
         R 3 , R 4 , and R 5  are independently selected from H, halo, —CN, lower straight chain or branched alkyl, and OR 6 ; 
         each R 6  is independently selected from H, lower straight chain or branched alkyl; 
         m is 0 or 1; 
         n is 0, 1, 2 or 3, provided that when m is 1, n is not 3; and
 Ar is a bicyclic aryl group having between 8 and 12 ring atoms, wherein 0, 1 or 2 ring atoms are heteroatoms independently selected from N, O, S and the bicyclic aryl group is substituted with 0, 1 or 2 groups independently selected from halo, —CN, lower straight chain or branched alkyl; 
 
         or a pharmaceutically acceptable salt form thereof, with the proviso that the compound is not 
       
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         14 . The method of  claim 13 , wherein Ar is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein: 
         R 8  is selected from H, halo and —CN; 
         R 9  is selected from H, lower straight chain or branched alkyl, —C(O)R 10  or —SO 2 R 10  and R 10  is selected from H, lower straight chain or branched alkyl. 
       
     
     
         15 . The method of  claim 14 , wherein at least one of R 3 , R 4 , or R 5  is in the ortho position and selected from the group consisting of halo, —CN, a straight chain or branched alkyl of 1 to 4 carbon atoms, and a straight or branched alkoxy of 1 to 4 carbon atoms. 
     
     
         16 . The method of  claim 14 , wherein at least two of R 3 , R 4 , or R 5  is in the ortho position and selected from the group consisting of halo, —CN, a straight chain or branched alkyl of 1 to 4 carbon atoms, and a straight or branched alkoxy of 1 to 4 carbon atoms. 
     
     
         17 . The method of  claim 13 , wherein R 2  is selected from halo, lower straight chain or branched alkyl, and OR 6 . 
     
     
         18 . The method of  claim 14 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and pharmaceutically acceptable salts thereof. 
     
     
         19 . A method of inhibiting HCMV production comprising contacting an HCMV-infected cell with a therapeutically effective amount of a compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         X is NH or O, provided that when m is 1, X is NH; 
         R 1  and R 2  are independently selected from H, halo, lower straight chain or branched alkyl, and OR 6 ; 
         R 3 , R 4 , and R 5  are independently selected from H, halo, —CN, lower straight chain or branched alkyl, and OR 6 ; 
         each R 6  is independently selected from H, lower straight chain or branched alkyl; 
         m is 0 or 1; 
         n is 0, 1, 2 or 3, provided that when m is 1, n is not 3; and
 Ar is a bicyclic aryl group having between 8 and 12 ring atoms, wherein 0, 1 or 2 ring atoms are heteroatoms independently selected from N, O, S and the bicyclic aryl group is substituted with 0, 1 or 2 groups independently selected from halo, —CN, lower straight chain or branched alkyl; 
 
         or a pharmaceutically acceptable salt form thereof, with the proviso that the compound is not 
       
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         20 . The method of  claim 19 , wherein Ar is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein: 
         R 8  is selected from H, halo and —CN; 
         R 9  is selected from H, lower straight chain or branched alkyl, —C(O)R 10  or —SO 2 R 10  and R 10  is selected from lower straight chain or branched alkyl. 
       
     
     
         21 . (canceled) 
     
     
         22 . (canceled) 
     
     
         23 . (canceled) 
     
     
         24 . The method of  claim 20 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and pharmaceutically acceptable salts thereof. 
     
     
         25 . (canceled) 
     
     
         26 . (canceled) 
     
     
         27 . (canceled)

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