US2015272962A1PendingUtilityA1

Methods for treating or preventing cancer and neurodegenerative diseases

Assignee: SLOAN KETTERING INST CANCERPriority: Dec 22, 2008Filed: Jun 10, 2015Published: Oct 1, 2015
Est. expiryDec 22, 2028(~2.4 yrs left)· nominal 20-yr term from priority
A61P 35/02A61P 43/00A61P 35/00A61P 25/28A61P 25/16A61P 25/00A61P 21/00A61K 31/5513A61K 31/381C07D 333/34C07D 409/12
42
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Claims

Abstract

Provided are methods of treating or preventing a neurodegenerative disease comprising administering to a subject having a neurodegenerative disease an effective amount of a compound of Formula I: where X, R 1 , R 2 , subscript m, subscript n and subscript v are as defined herein.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A method for treating or preventing cancer, comprising administering to a subject in need of treatment or prevention of the cancer an effective amount of a compound of Formula I 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein:
 X is H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 R 2  is 
 
       
         
           
           
               
               
           
         
         each R 3  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
         Z 1  is NH, O, or CH 2 ; 
         Z 2  is —(C 1 -C 6  alkylene)-, —(C 2 -C 6  alkenylene)-, or —(O—(C 2 -C 6  alkylene))-; 
         m is 3; 
         n is 1; 
         p is an integer from 1 to 5; 
         q is 0 or 1; and 
         v is an integer from 1 to 3. 
       
     
     
         2 . The method of  claim 1 , wherein the compound of Formula I has the following Formula Ia 
       
         
           
           
               
               
           
         
       
       wherein:
 X is H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 3  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 Z 1  is NH, O, or CH 2 ; 
 Z 2  is —(C 1 -C 6  alkylene)-, —(C 2 -C 6  alkenylene)-, or —(O—(C 2 -C 6  alkylene))-; 
 m is 3; 
 p is an integer from 1 to 5; 
 q is 0 or 1; and 
 v is an integer from 1 to 3. 
 
     
     
         3 . The method of  claim 2 , wherein the compound of Formula Ia has the following Formula Iaa 
       
         
           
           
               
               
           
         
       
       wherein:
 X is halo; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 each R 3  is independently H, halo, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 Z 2  is —(C 1 -C 6  alkylene)-, —(C 2 -C 6  alkenylene)-, or —(O—(C 2 -C 6  alkylene))-; 
 m is 3; 
 p is an integer from 1 to 5; 
 q is 0 or 1; and 
 v is an integer from 1 to 3. 
 
     
     
         4 . The method of any one of  claims 1  to  3 , wherein each R 1  is H. 
     
     
         5 . The method of any one of  claims 1  to  4 , wherein q is 0. 
     
     
         6 . The method of any one of  claims 1  to  5 , wherein v is 1 and X is in the 5-position of the thiopheno group. 
     
     
         7 . The method of any one of  claims 1  to  6 , wherein p is 1 and R 3  is in the 4-position of the phenyl group. 
     
     
         8 . The method of  claim 3 , wherein the compound of Formula Iaa has the structure: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         9 . The method of  claim 3 , wherein the compound of Formula Iaa has the structure: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         10 . A method for treating or preventing cancer, comprising administering to a subject in need of treatment or prevention of the cancer an effective amount of a compound of Formula II 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein:
 X is H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 R 4  is 
 
       
         
           
           
               
               
           
         
         each R 3  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
         R 5  is H, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
         Z 1  is NH, O, or CH 2 ; 
         Z 2  is —(C 1 -C 6  alkylene)- or —(C 2 -C 6  alkenylene)-; 
         m is 3; 
         n is 1; 
         p is 5; 
         t is 4; 
         q is 0 or 1; and 
         v is an integer from 1 to 3. 
       
     
     
         11 . The method of  claim 10 , wherein the compound of Formula II has the following Formula IIa 
       
         
           
           
               
               
           
         
       
       wherein:
 X is H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 3  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 R 5  is H, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 Z 1  is NH, O or CH 2 ; 
 Z 2  is —(C 1 -C 6  alkylene)- or —(C 2 -C 6  alkenylene)-; 
 m is 3; 
 p is 5; 
 t is 4; 
 q is 0 or 1; and 
 v is an integer from 1 to 3. 
 
     
     
         12 . The method of  claim 11 , wherein the compound of Formula IIa has the following Formula IIaa 
       
         
           
           
               
               
           
         
       
       wherein:
 X is halo; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 each R 3  is independently H, halo, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 Z 2  is —(C 1 -C 6  alkylene)- or —(C 2 -C 6  alkenylene)-; 
 R 5  is H, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 m is 3; 
 p is 5; 
 t is 4; 
 q is 0 or 1; and 
 v is an integer from 1 to 3. 
 
     
     
         13 . The method of any one of  claims 10  to  12 , wherein each R 1  is H. 
     
     
         14 . The method of any one of  claims 10  to  13 , wherein R 5  is H or methyl. 
     
     
         15 . The method of any one of  claims 10  to  14 , wherein R 5  is methyl. 
     
     
         16 . The method of any one of  claims 10  to  15 , wherein q is 0. 
     
     
         17 . The method of any one of  claims 10  to  16 , wherein v is 1 and X is in the 5-position of the thiopheno group. 
     
     
         18 . The method of  claim 12 , wherein the compound of Formula IIaa has the structure: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         19 . The method of  claim 12 , wherein the compound of Formula IIaa has the structure: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         20 . A method for treating or preventing a neurodegenerative disease, comprising administering to a subject in need of treatment or prevention of the neurodegenerative disease an effective amount of a compound of Formula I 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein:
 X is H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 R 2  is 
 
       
         
           
           
               
               
           
         
         each R 3  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
         Z 1  is NH, O, or CH 2 ; 
         Z 2  is —(C 1 -C 6  alkylene)-, —(C 2 -C 6  alkenylene)-, or —(O—(C 2 -C 6  alkylene))-; 
         m is 3; 
         n is 1; 
         p is an integer from 1 to 5; 
         q is 0 or 1; and 
         v is an integer from 1 to 3. 
       
     
     
         21 . The method of  claim 20 , wherein the compound of Formula I has the following Formula Ia 
       
         
           
           
               
               
           
         
       
       wherein:
 X is H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 3  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 Z 1  is NH, O, or CH 2 ; 
 Z 2  is —(C 1 -C 6  alkylene)-, —(C 2 -C 6  alkenylene)-, or —(O—(C 2 -C 6  alkylene))-; 
 m is 3; 
 p is an integer from 1 to 5; 
 q is 0 or 1; and 
 v is an integer from 1 to 3. 
 
     
     
         22 . The method of  claim 21 , wherein the compound of Formula Ia has the following Formula Iaa 
       
         
           
           
               
               
           
         
       
       wherein:
 X is halo; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 each R 3  is independently H, halo, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 Z 2  is —(C 1 -C 6  alkylene)-, —(C 2 -C 6  alkenylene)-, or —(O—(C 2 -C 6  alkylene))-; 
 m is 3; 
 p is an integer from 1 to 5; 
 q is 0 or 1; and 
 v is an integer from 1 to 3. 
 
     
     
         23 . The method of any one of  claims 20  to  22 , wherein each R 1  is H. 
     
     
         24 . The method of any one of  claims 20  to  23 , wherein q is 0. 
     
     
         25 . The method of any one of  claims 20  to  24 , wherein v is 1 and X is in the 5-position of the thiopheno group. 
     
     
         26 . The method of any one of  claims 20  to  25 , wherein p is 1 and R 3  is in the 4-position of the phenyl group. 
     
     
         27 . The method of  claim 22 , wherein the compound of Formula Iaa has the structure: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         28 . The method of  claim 22 , wherein the compound of Formula Iaa has the structure: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         29 . The method of any one of  claims 20  to  28 , wherein the neurodegenerative disease is Alzheimer's disease, Parkinson's disease, ALS, or MS. 
     
     
         30 . The method of any one of  claims 20  to  29 , wherein the neurodegenerative disease is Alzheimer's disease. 
     
     
         31 . A method for treating or preventing a neurodegenerative disease, comprising administering to a subject in need of treatment or prevention of the neurodegenerative disease an effective amount of a compound of Formula II 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein:
 X is H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 3  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 R 4  is 
 
       
         
           
           
               
               
           
         
         R 5  is H, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
         Z 1  is NH, O, or CH 2 ; 
         Z 2  alkylene)- or —(C 2 -C 6  alkenylene)-; 
         m is 3; 
         n is 1; 
         p is 5; 
         t is 4; 
         q is 0 or 1; and 
         v is an integer from 1 to 3. 
       
     
     
         32 . The method of  claim 31 , wherein the compound of Formula II has the following Formula IIa 
       
         
           
           
               
               
           
         
       
       wherein:
 X is H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 each R 3  is independently H, halo, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  alkoxy, or cyano; 
 R 5  is H, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 Z 1  is NH, O or CH 2 ; 
 Z 2  alkylene)- or —(C 2 -C 6  alkenylene)-; 
 m is 3; 
 p is 5; 
 t is 4; 
 q is 0 or 1; and 
 v is an integer from 1 to 3. 
 
     
     
         33 . The method of  claim 32 , wherein the compound of Formula IIa has the following Formula IIaa 
       
         
           
           
               
               
           
         
       
       wherein:
 X is halo; 
 each R 1  is independently H, halo, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 each R 3  is independently H, halo, C 1 -C 6  alkyl, or C 1 -C 6  haloalkyl; 
 Z 2  is —(C 1 -C 6  alkylene)- or —(C 2 -C 6  alkenylene)-; 
 m is 3; 
 p is 5; 
 t is 4; 
 q is 0 or 1; and 
 v is an integer from 1 to 3. 
 
     
     
         34 . The method of any one of  claims 31  to  33 , wherein each R 1  is H. 
     
     
         35 . The method of any one of  claims 31  to  34 , wherein R 5  is H or methyl. 
     
     
         36 . The method of any one of  claims 31  to  35 , wherein R 5  is methyl. 
     
     
         37 . The method of any one of  claims 31  to  36 , wherein q is 0. 
     
     
         38 . The method of any one of  claims 31  to  37 , wherein v is 1 and X is in the 5-position of the thiopheno group. 
     
     
         39 . The method of  claim 33 , wherein the compound of Formula IIaa has the structure: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         40 . The method of  claim 33 , wherein the compound of Formula IIaa has the structure: 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof. 
     
     
         41 . The method of any one of  claims 31  to  40 , wherein the neurodegenerative disease is Alzheimer's disease, Parkinson's disease, ALS, or MS. 
     
     
         42 . The method of any one of  claims 31  to  41 , wherein the neurodegenerative disease is Alzheimer's disease.

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