US2016272589A1PendingUtilityA1

Dual mechanism inhibitors for the treatment of disease

Assignee: AERIE PHARMACEUTICALS INCPriority: May 1, 2009Filed: Mar 21, 2016Published: Sep 22, 2016
Est. expiryMay 1, 2029(~2.8 yrs left)· nominal 20-yr term from priority
A61P 9/12A61P 9/10A61P 9/00A61P 35/00A61P 43/00A61P 3/04A61P 29/00A61P 27/06A61P 27/00A61P 27/04A61P 27/02A61P 1/16A61P 11/00A61P 13/12A61P 19/08A61P 13/10A61P 17/14A61P 1/04A61P 19/02A61P 11/02A61P 15/18A61P 1/00A61P 1/18A61P 17/00C07D 217/02C07D 413/12C07D 217/24C07D 333/38C07D 417/12C07C 237/42C07D 405/12C07D 217/00C07D 217/04C07C 2601/08C07D 401/12C07C 237/20C07C 2601/14C07D 217/22C07D 333/40C07D 409/12
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Claims

Abstract

Provided are compounds that are inhibitors of both rho kinase and of a monoamine transporter (MAT) act to improve the disease state or condition. Further provided are compositions comprising the compounds. Further provided are methods for treating diseases or conditions, the methods comprising administering compounds according to the invention. One such disease may be glaucoma for which, among other beneficial effects, a marked reduction in intraocular pressure (IOP) may be achieved.

Claims

exact text as granted — not AI-modified
1 .- 39 . (canceled) 
     
     
         40 . A compound according to the Formula: 
       
         
           
           
               
               
           
         
         and salts thereof, 
         wherein R 1 , R 2 , and R 3  are independently hydrogen or C 1 -C 4  alkyl; 
         wherein A is C 1 -C 4  alkyl, or forms a ring structure with R 1 , R 2 , or R 3 ; 
         wherein B is hydrogen, an aryl group, a heteroaryl group, a cycloalkyl group, a heterocycloalkyl group, C 1 -C 22  alkyl, C 1 -C 22  alkyl aryl, C 1 -C 22  alkyl heteroaryl, C 2 -C 22  alkenyl, C 2 -C 22  alkynyl, C 1 -C 22  carbonyl, C 1 -C 22  carbonylamino, C 1 -C 22  alkoxy, C 1 -C 22  sulfonyl, C 1 -C 22  sulfonylamino, C 1 -C 22  thioalkyl, or C 1 -C 22  carboxyl; 
         wherein X 1 , X 2 , and X 3  are, independently, hydrogen, hydroxyl, halogen, C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, amino, aminocarbonyl, nitro, cyano, C 1 -C 4  carbonyl, C r  C 4  carbonylamino, C 1 -C 4  alkoxy, C 1 -C 4  sulfonyl, C 1 -C 4  sulfonylamino, C 1 -C 4  thioalkyl, or C 1 -C 4  carboxyl; 
         wherein the double circle 
       
       
         
           
           
               
               
           
         
       
       indicates an aromatic or heteroaromatic ring; and
 wherein each Z is independently a bond. 
 
     
     
         41 . A compound according to  claim 40 , wherein R 1  is hydrogen or C 1 -C 4  alkyl; B is C 1 -C 22  carbonyl; X 1 , X 2 , and X 3  are hydrogen; the double circle 
       
         
           
           
               
               
           
         
       
       indicates an aromatic or heteroaromatic ring; and Z is a bond, C 1 -C 4  alkyl, C 1 -C 4  heteroalkyl, or an O atom. 
     
     
         42 . A compound according to  claim 40 , wherein X 1 , X 2  and X 3  are each hydrogen. 
     
     
         43 . A compound according to  claim 40 , wherein R 1  and R 2  are independently hydrogen or methyl. 
     
     
         44 . A compound according to  claim 40 , wherein R 3  is C 1 -C 4  alkyl. 
     
     
         45 . A compound according to  claim 40 , wherein the double circle 
       
         
           
           
               
               
           
         
       
       is a phenyl ring. 
     
     
         46 . A compound according to  claim 40 , wherein R 1  and R 2  are hydrogen or methyl; R 3  is hydrogen; the double circle 
       
         
           
           
               
               
           
         
       
       is a phenyl ring; X 1 , X 2 , and X 3  are hydrogen; A is —CH 2 —; and B is C 1 -C 22  carbonyl. 
     
     
         47 . A compound according to  claim 46 , wherein B is —CH 2 C(O)R and R is aryl or alkyl. 
     
     
         48 . A compound according to  claim 47 , wherein R is phenyl. 
     
     
         49 . A compound according to  claim 47 , wherein R is C 1-4  alkyl. 
     
     
         50 . A compound according to Formula IV: 
       
         
           
           
               
               
           
         
         and salts thereof, 
         wherein R 1  and R 2  are independently hydrogen or C 1 -C 4  alkyl; 
         wherein R 3  is a hydrogen or C 1 -C 4  alkyl; 
         wherein X 1 , X 2 , and X 3  are, independently, hydrogen, hydroxyl, halogen, C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, amino, aminocarbonyl, nitro, cyano, C 1 -C 4  carbonyl, C 1 -C 4  carbonylamino, C 1 -C 4  alkoxy, C 1 -C 4  sulfonyl, C 1 -C 4  sulfonylamino, C 1 -C 4  thioalkyl, or C 1 -C 4  carboxyl; 
         wherein B is hydrogen, C 1 -C 18  alkyl, C 1 -C 18  alkyl aryl, C 1 -C 18  alkyl heteroaryl, C 1 -C 18  carbonyl, C 1 -C 18  carbonylamino, C 1 -C 18  sulfonyl, C 1 -C 18  sulfonylamino, or C 1 -C 18  carboxyl; and 
         wherein Z is a bond. 
       
     
     
         51 . A compound according to  claim 50 , wherein R 1  and R 2  are hydrogen or methyl; X 1 , X 2 , and X 3  are hydrogen; and B is C 1-18  carbonyl. 
     
     
         52 . A compound according to  claim 51 , wherein B is —CH 2 C(O)R and R is aryl or alkyl. 
     
     
         53 . A compound according to  claim 52 , wherein R is phenyl. 
     
     
         54 . A compound according to  claim 52 , wherein R is C 1-4  alkyl. 
     
     
         55 . A compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         56 . A compound selected from the group consisting of: 
       
         
           
                 
               
                     
                 
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                 
                 
                 
                 
               
                   Example 
                   X 
                   R 
                 
                     
                 
                   279 
                   O 
                   Ph 
                 
                   280 
                   OH 
                   Ph 
                 
                   281 
                   O 
                   -4-MeOPh 
                 
                   282 
                   O 
                   -3-MeOPh. 
                 
                     
                 
             
                
               
               
                
                
               
            
             
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         57 . A compound selected from the group consisting of: 
       
         
           
                 
                 
               
                     
                     
                 
                     
                   
                     
                       
                       
                           
                           
                       
                     
                   
                 
                     
                     
                 
                 
                 
                 
                 
                 
               
                     
                   Example 
                   X 
                   R1 
                   R2 
                 
                     
                     
                 
                     
                   283 
                   O 
                   -2-F—Ph 
                   Me 
                 
                     
                   284 
                   O 
                   -2,4 diCl—Ph 
                   H 
                 
                     
                   285 
                   O 
                   -3-MePh 
                   H 
                 
                     
                   286 
                   OH 
                   -4-MeOPh 
                   H 
                 
                     
                   287 
                   OH 
                   -2-MeOPh 
                   H 
                 
                     
                   288 
                   OH 
                   -3-MePh 
                   Me. 
                 
                     
                     
                 
             
                
               
               
                
                
               
            
             
                
                
                
                
                
                
                
                
                
               
            
           
         
       
     
     
         58 . A pharmaceutical composition comprising a compound according to  claim 40  and a pharmaceutically acceptable carrier. 
     
     
         59 . A method for treating a disease in a subject comprising administering to a subject an effective amount of a compound according to  claim 40 ; wherein the disease comprises eye disease. 
     
     
         60 . The method of  claim 59 , wherein the eye disease comprises glaucoma or neurodegenerative eye disease. 
     
     
         61 . A method of modulating kinase activity comprising contacting a cell with an compound according to  claim 40  in an amount effective to modulate kinase activity. 
     
     
         62 . The method of  claim 61 , wherein the cell is in a subject. 
     
     
         63 . A method of reducing intraocular pressure comprising contacting a cell with a compound according to  claim 40  in an amount effective to reduce intraocular pressure. 
     
     
         64 . The method of  claim 63 , wherein the cell is in a subject.

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