Deuterium-enriched bupropion

Abstract

The present application describes deuterium-enriched bupropion, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.

1 . A deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein R 1 -R 18  are independently selected from H and D; and 
         the abundance of deuterium in R 1 -R 18  is at least 6%. 
       
     
     
         2 . A deuterium-enriched compound of  claim 1 , wherein the abundance of deuterium in R 1 -R 18  is selected from at least 6% , at least 11%, at least 17%, at least 22%, at least 28%, at least 33%, at least 39%, at least 44%, at least 50%, at least 56%, at least 61%, at least 67%, at least 72%, at least 78%, at least 83%, at least 89%, at least 94%, and 100%. 
     
     
         3 . A deuterium-enriched compound of  claim 1 , wherein the abundance of deuterium in R 1  is 100%. 
     
     
         4 . A deuterium-enriched compound of  claim 1 , wherein the abundance of deuterium in R 2  is 100%. 
     
     
         5 . A deuterium-enriched compound of  claim 1 , wherein the abundance of deuterium in R 3 -R 5  is selected from at least 33%, at least 67%, and 100%. 
     
     
         6 . A deuterium-enriched compound of  claim 1 , wherein the abundance of deuterium in R 6 -R 9  is selected from at least 25%, at least 50%, at least 75%, and 100%. 
     
     
         7 . A deuterium-enriched compound of  claim 1 , wherein the abundance of deuterium in R 10 -R 18  is selected from at least 11%, at least 22%, at least 33%, at least 44%, at least 56%, at least 67%, at least 78%, 100%. 
     
     
         8 . A deuterium-enriched compound of  claim 1 , wherein the compound is selected from compounds 1-6 of Table 1: 
     
     
         9 . A deuterium-enriched compound of  claim 1 , wherein the compound is selected from compounds 7-12 of Table 2: 
     
     
         10 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein R 1 -R 18  are independently selected from H and D; and 
         the abundance of deuterium in R 1 -R 18  is at least 6%. 
       
     
     
         11 . An isolated deuterium-enriched compound of  claim 10 , wherein the abundance of deuterium in R 1 -R 18  is selected from at least 6%, at least 11%, at least 17%, at least 22%, at least 28%, at least 33%, at least 39%, at least 44%, at least 50%, at least 56%, at least 61%, at least 67%, at least 72%, at least 78%, at least 83%, at least 89%, at least 94%, and 100%. 
     
     
         12 . An isolated deuterium-enriched compound of  claim 10 , wherein the abundance of deuterium in R 1  is 100%. 
     
     
         13 . An isolated deuterium-enriched compound of  claim 10 , wherein the abundance of deuterium in R 2  is 100%. 
     
     
         14 . An isolated deuterium-enriched compound of  claim 10 , wherein the abundance of deuterium in R 3 -R 5  is selected from at least 33%, at least 67%, and 100%. 
     
     
         15 . An isolated deuterium-enriched compound of  claim 10 , wherein the compound is selected from compounds 1-6 of Table 1: 
     
     
         16 . An isolated deuterium-enriched compound of  claim 10 , wherein the compound is selected from compounds 7-12 of Table 2: 
     
     
         17 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein R 1 -R 18  are independently selected from H and D; and 
         the abundance of deuterium in R 1 -R 18  is at least 6%. 
       
     
     
         18 . A mixture of deuterium-enriched compounds of  claim 16 , wherein the compound is selected from compounds 1-6 of Table 1: 
     
     
         19 . A mixture of deuterium-enriched compounds of  claim 16 , wherein the compound is selected from compounds 7-12 of Table 2: 
     
     
         20 . A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of  claim 1  or a pharmaceutically acceptable salt form thereof. 
     
     
         21 . A method for treating a disease selected from antidepressant and/or as a smoking cessation aid comprising: administering, to a patient in need thereof, a therapeutically effective amount of a compound of  claim 1  or a pharmaceutically acceptable salt form thereof.