US2022119386A1PendingUtilityA1

Fused ring derivative used as fgfr4 inhibitor

Assignee: JACOBIO PHARMACEUTICALS CO LTDPriority: Jul 27, 2018Filed: Sep 9, 2021Published: Apr 21, 2022
Est. expiryJul 27, 2038(~12 yrs left)· nominal 20-yr term from priority
A61P 35/00C07D 471/04A61K 31/4375C07D 519/00A61K 31/541A61K 31/496
68
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Claims

Abstract

A compound represented by formula I or a pharmaceutically acceptable salt thereof and a use thereof in preparing a drug for treating, stopping or preventing a disease or disorder mediated by FGFR4 activity.

Claims

exact text as granted — not AI-modified
1 - 50 . (canceled) 
     
     
         51 . A compound of formula (I), or a pharmaceutically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is selected from: 
       
       
         
           
           
               
               
           
         
         R 2  and R 3  are H; 
       
       
         
           
           
               
               
           
         
       
       is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         52 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 51 , wherein R 1  is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         53 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 52 , wherein R 1  is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         54 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 51 , wherein 
       
         
           
           
               
               
           
         
       
       is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         55 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 54 , wherein 
       
         
           
           
               
               
           
         
       
       is selected from: 
       
         
           
           
               
               
           
         
       
     
     
         56 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 51 , which is selected from: 
       
         
           
                 
                 
                 
               
                     
                 
                   Com- 
                     
                     
                 
                   pound 
                     
                     
                 
                   No. 
                   Chemical Name 
                   Structure Formula 
                 
                     
                 
                     
                 
                 
                 
                 
               
                   1 
                   N-(5-cyano-4-((2-(methylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6-((4- methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   4 
                   (R)-N-(5-cyano-4-((1-(methylthio)propan-2-yl)amino)pyridin-2-yl)-7- formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   6 
                   N-(5-cyano-4-((2-methyl-2-(methylthio)propyl)amino)pyridin-2-yl)-7- formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   7 
                   (R)-N-(5-cyano-4-((1-(methylthio)propan-2-yl)amino)pyridin-2-yl)-7- formyl-6-((2-oxopyrrolidine-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   8 
                   (R)-N-(5-cyano-4-((2-(methylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6- ((3-methoxy-2-oxopyrrolidin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   9 
                   N-(5-cyano-4-(((R)-1-(methylthio)propan-2-yl)amino)pyridin-2-yl)-7- formyl-6-(((R)-3-methoxy-2-oxopyrrolidin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   13 
                   (S)-N-(5-cyano-4-((2-(methylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6- ((3-methoxy-2-oxopyrrolidin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   14 
                   N-(5-cyano-4-((2-(methylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6-((5- oxo-6-oxa-4-azaspiro[2.4]heptan-4-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   15 
                   N-(5-cyano-4-((2-(methylthio)ethyl)amino)pyridin-2-yl)-6-((4-cyclopropyl- 2-oxopiperazin-1-yl)methyl)-7-formyl-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   16 
                   N-(5-cyano-4-((2-(methylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6-((2- oxo-1,3-oxazepan-3-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)- carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   19 
                   N-(5-cyano-4-((2-((methyl-d3)thio)ethyl)amino)pyridin-2-yl)-7-formyl-6- ((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   23 
                   N-(5-cyano-4-((2-(methylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6-((2- oxopyrrolidin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carbox- amide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   27 
                   N-(5-cyano-4-((2-(methylsulfinyl)ethyl)amino)pyridin-2-yl)-7-formyl-6- ((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   31 
                   N-(5-cyano-4-((2-(methylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6-((4- methyl-2-oxopiperazin-1-yl)methyl-d2)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   62 
                   N-(5-cyano-4-((2-((trifluoromethyl)thio)ethyl)amino)pyridin-2-yl)-7-formyl- 6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   64 
                   N-(5-cyano-4-((3-(methylthio)propyl)amino)pyridin-2-yl)-7-formyl-6- ((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   69 
                   N-(5-cyano-4-(((2R)-1-(methylsulfinyl)propan-2-yl)amino)pyridin-2-yl)- 7-formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   70 
                   (R)-N-(5-cyano-4-((1-(methylthio)propan-2-yl)amino)pyridin-2-yl)-7- formyl-6-((2-oxo-1,3-oxozepan-3-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   71 
                   N-(5-cyano-4-((2-(ethylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6-((4- methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)- carboxamide hydrochloride 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   72 
                   N-(5-cyano-4-((2-(methylsulfonyl)ethyl)amino)pyridin-2-yl)-7-formyl-6- ((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide hydrochloride 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   82 
                   N-(5-cyano-4-((1-(methylthio)propan-2-yl)amino)pyridin-2-yl)-7-formyl- 6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                   83 
                   N-(5-cyano-4-(((2R)-1-(methylsulfonyl)propan-2-yl)amino)pyridin-2-yl)- 7-formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
                
                
                
                
               
               
                
               
            
             
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         57 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 56 , which is: 
       
         
           
                 
                 
                 
               
                     
                 
                   6 
                   N-(5-cyano-4-((2-methyl-2-(methylthio)propyl)amino)pyridin-2-yl)-7- formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         58 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 56 , which is: 
       
         
           
                 
                 
                 
               
                     
                 
                   9 
                   N-(5-cyano-4-(((R)-1-(methylthio)propan-2-yl)amino)pyridin-2-yl)-7- formyl-6-(((R)-3-methoxy-2-oxopyrrolidin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         59 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 56 , which is: 
       
         
           
                 
                 
                 
               
                     
                 
                   62 
                   N-(5-cyano-4-((2-((trifluoromethyl)thio)ethyl)amino)pyridin-2-yl)-7- formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         60 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 56 , which is: 
       
         
           
                 
                 
                 
               
                     
                 
                   64 
                   N-(5-cyano-4-((3-(methylthio)propyl)amino)pyridin-2-yl)-7-formyl-6- ((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         61 . The compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 56 , which is: 
       
         
           
                 
                 
                 
               
                     
                 
                   71 
                   N-(5-cyano-4-((2-(ethylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6-((4- methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)- carboxamide hydrochloride 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         62 . A pharmaceutical composition comprising the compound of formula (I) or pharmaceutically acceptable salt thereof according to  claim 51 , and at least one pharmaceutically acceptable excipient. 
     
     
         63 . The pharmaceutical composition according to  claim 62 , wherein the compound of formula (I) is: 
       
         
           
                 
                 
                 
               
                     
                 
                   6 
                   N-(5-cyano-4-((2-methyl-2-(methylthio)propyl)amino)pyridin-2-yl)-7- formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         64 . The pharmaceutical composition according to  claim 62 , wherein the compound of formula (I) is: 
       
         
           
                 
                 
                 
               
                     
                 
                   9 
                   N-(5-cyano-4-(((R)-1-(methylthio)propan-2-yl)amino)pyridin-2-yl)-7- formyl-6-(((R)-3-methoxy-2-oxopyrrolidin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         65 . The pharmaceutical composition according to  claim 62 , wherein the compound of formula (I) is: 
       
         
           
                 
                 
                 
               
                     
                 
                   62 
                   N-(5-cyano-4-((2-((trifluoromethyl)thio)ethyl)amino)pyridin-2-yl)-7- formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         66 . The pharmaceutical composition according to  claim 62 , wherein the compound of formula (I) is: 
       
         
           
                 
                 
                 
               
                     
                 
                   64 
                   N-(5-cyano-4-((3-(methylthio)propyl)amino)pyridin-2-yl)-7-formyl-6- ((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine- 1(2H)-carboxamide 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         67 . The pharmaceutical composition according to  claim 62 , wherein the compound of formula (I) is: 
       
         
           
                 
                 
                 
               
                     
                 
                   71 
                   N-(5-cyano-4-((2-(ethylthio)ethyl)amino)pyridin-2-yl)-7-formyl-6-((4- methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)- carboxamide hydrochloride 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
             
                
               
               
                
                
               
            
           
         
       
     
     
         68 . A method for the treatment or prevention of a disease or condition mediated by FGFR4 activity, comprising administering to a subject a therapeutically effective amount of the compound of formula (I) or pharmaceutically acceptable salt thereof according to claim  51 . 
     
     
         69 . The method according to  claim 68 , wherein the disease or condition mediated by FGFR4 activity is selected from one or more of liver cancer, head and neck cancer, esophageal cancer, stomach cancer, prostate cancer, ovarian cancer, lung cancer, breast cancer, colorectal cancer, rhabdomyoma, and a combination thereof. 
     
     
         70 . The method according to  claim 68 , wherein the compound of formula (I) is: 
       
         
           
                 
                 
                 
               
                     
                 
                   4 
                   (R)-N-(5-cyano-4-((1-(methylthio)propan-2-yl)amino)pyridin-2-yl)-7- formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8- naphthyridine-1(2H)-carboxamide

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