US2018009750A1PendingUtilityA1

5-methoxytryptophan and its derivatives and uses thereof

Assignee: NATIONAL HEALTH RES INSTPriority: Jan 13, 2015Filed: Jan 13, 2016Published: Jan 11, 2018
Est. expiryJan 13, 2035(~8.4 yrs left)· nominal 20-yr term from priority
A61P 29/00C07D 209/20A61K 31/405
31
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Claims

Abstract

A 5-methoxytryptophan and its derivatives are disclosed, wherein the 5-methoxytryptophan and its derivatives are represented by the following formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , and n are defined in the specification. In addition, the present invention also provides novel used of the 5-methoxytryptophan and its derivatives for treating inflammatory-related disease and cancers.

Claims

exact text as granted — not AI-modified
1 . A method for treating an inflammatory-related disease, comprising administering to a subject in need thereof and effective amount of a compound of formula (I): 
       
         
           
           
               
               
           
         
       
       Wherein
 R 1  is H, halogen atom, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 2  is C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 3  is H, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 4  is H, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, C 3 -C 20  cycloalkenyl, C(O)R a , or C(O)OR a ; in which R a  is H, C 1 -C 10  alkyl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, aryl, or heteroaryl; 
 R 5  is H, C 1 -C 10  alkyl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, aryl, or heteroaryl; and 
 n is 0-5. 
 
     
     
         2 . The method as claimed in  claim 1 , wherein each R 1  and R 2 , independently, is H or C 1 -C 10  alkyl. 
     
     
         3 . The method as claimed in  claim 2 , wherein R 1  is H, and R 2  is C 1 -C 3  alkyl. 
     
     
         4 . The method as claimed in  claim 1 , wherein R 3  is H, C 1 -C 10  alkyl, and R 4  is H, C 1 -C 10  alkyl, C(O)R a , or C(O)OR a , in which R a  is H, or C 1 -C 10  alkyl. 
     
     
         5 . The method as claimed in  claim 4 , wherein R 3  is H, and R 4  is H or C(O)R a , in which R a  is C 1 -C 3  alkyl. 
     
     
         6 . The method as claimed in  claim 1 , wherein R 5  is H or C 1 -C 10  alkyl. 
     
     
         7 . The method as claimed in  claim 6 , wherein R 5  is H or C 1 -C 3  alkyl. 
     
     
         8 . The method as claimed in  claim 1 , wherein n is 1 or 2. 
     
     
         9 . The method as claimed in  claim 1 , wherein the inflammatory-related disease is sepsis, Systemic Lupus Erythematosus (SLE), cardiovascular diseases, metabolic syndrome, cancer, septicemia and diverse inflammatory joint, gastrointestinal, or renal diseases. 
     
     
         10 . The method as claimed in  claim 9 , wherein the inflammatory-related disease is sepsis, SLE or cancer. 
     
     
         11 . The method as claimed in  claim 1 , wherein the compound is 
       
         
           
           
               
               
           
         
       
     
     
         12 . A method for treating a cancer, comprising administering to a subject in need thereof and effective amount of a compound of formula (I): 
       
         
           
           
               
               
           
         
       
       Wherein
 R 1  is H, halogen atom, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 2  is alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 3  is H, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 4  is H, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, C 3 -C 20  cycloalkenyl, C(O)R a , or C(O)OR a ; in which R a  is H, C 1 -C 10  alkyl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, aryl, or heteroaryl; 
 R 5  is H, C 1 -C 10  alkyl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, aryl, or heteroaryl; and 
 n is 0-5. 
 
     
     
         13 . The method as claimed in  claim 12 , wherein each R 1  and R 2 , independently, is H or C 1 -C 10  alkyl. 
     
     
         14 . The method as claimed in  claim 13 , wherein R 1  is H, and R 2  is C 1 -C 3  alkyl. 
     
     
         15 . The method as claimed in  claim 12 , wherein R 3  is H, C 1 -C 10  alkyl, and R 4  is H, C 1 -C 10  alkyl, C(O)R a , or C(O)OR a , in which R a  is H, or C 1 -C 10  alkyl. 
     
     
         16 . The method as claimed in  claim 15 , wherein R 3  is H, and R 4  is H or C(O)R a , in which R a  is C 1 -C 3  alkyl. 
     
     
         17 . The method as claimed in  claim 12 , wherein R 5  is H or C 1 -C 10  alkyl. 
     
     
         18 . The method as claimed in  claim 17 , wherein R 5  is H or C 1 -C 3  alkyl. 
     
     
         19 . The method as claimed in  claim 12 , wherein n is 1 or 2. 
     
     
         20 . The method as claimed in  claim 12 , wherein the cancer is a lung cancer, or a breast cancer. 
     
     
         21 . The method as claimed in  claim 1 , wherein the compound is 
       
         
           
           
               
               
           
         
       
     
     
         22 . A compound of formula (I): 
       
         
           
           
               
               
           
         
       
       Wherein
 R 1  is H, halogen atom, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 2  is C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 3  is H, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 4  is H, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, C 3 -C 20  cycloalkenyl, C(O)R a , or C(O)OR a ; in which R a  is H, C 1 -C 10  alkyl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, aryl, or heteroaryl; 
 R 5  is H, C 1 -C 10  alkyl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, aryl, or heteroaryl; and 
 n is 0-5, 
 with the proviso that R 1 , R 3 , R 4  and R 5  are not H when R 2  is C 1 -C 10  alkyl. 
 
     
     
         23 . The compound as claimed in  claim 22 , wherein each R 1  and R 2 , independently, is H or C 1 -C 10  alkyl. 
     
     
         24 . The compound as claimed in  claim 23 , wherein R 1  is H, and R 2  is C 1 -C 3  alkyl. 
     
     
         25 . The compound as claimed in  claim 22 , wherein R 3  is H, C 1 -C 10  alkyl, and R 4  is H, C 1 -C 10  alkyl, C(O)R a , or C(O)OR a , in which R a  is H, or C 1 -C 10  alkyl. 
     
     
         26 . The compound as claimed in  claim 25 , wherein R 3  is H, and R 4  is H or C(O)R a , in which R a  is C 1 -C 3  alkyl. 
     
     
         27 . The compound as claimed in  claim 22 , wherein R 5  is H or C 1 -C 10  alkyl. 
     
     
         28 . The compound as claimed in  claim 27 , wherein R 5  is H or C 1 -C 3  alkyl. 
     
     
         29 . The compound as claimed in  claim 22 , wherein n is 1 or 2. 
     
     
         30 . The compound as claimed in  claim 22 , which is 
       
         
           
           
               
               
           
         
       
     
     
         31 . A pharmaceutical composition, comprising a pharmaceutically acceptable carrier and a compound of formula (I): 
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is H, halogen atom, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 2  is C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 3  is H, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, or C 3 -C 20  cycloalkenyl; 
 R 4  is H, C 1 -C 10  alkyl, C 2 -C 10  alkenyl, C 2 -C 10  alkynyl, C 3 -C 20  cycloalkyl, C 3 -C 20  cycloalkenyl, C(O)R a , or C(O)OR a ; in which R a  is H, C 1 -C 10  alkyl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, aryl, or heteroaryl; 
 R 5  is H, C 1 -C 10  alkyl, C 3 -C 20  cycloalkyl, C 3 -C 20  heterocycloalkyl, aryl, or heteroaryl; and 
 n is 0-5, 
 with the proviso that R 1 , R 3 , R 4  and R 5  are not H when R 2  is C 1 -C 10  alkyl.

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