DEUTERIUM-ENRICHED SERTRALINE
The present application describes deuterium-enriched sertraline, 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 17 are independently selected from H and D; and the abundance of deuterium in R 1 -R 17 is at least 4%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 17 is selected from at least 6%, at least, at least 12%, at least 18%, at least 24%, at least 29%, at least 35%, at least 41%, at least 47%, at least 53%, at least 59%, at least 65%, at least 71%, at least 76%, at least 82%, at least 88%, at least 94%, and 100%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 is selected from at least 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 17 is selected from at least 6%, at least, at least 13%, at least 19%, at least 25%, at least 31%, at least 38%, at least 44%, at least 50%, at least 56%, at least 63%, at least 69%, at least 75%, at least 81%, at least 88%, at least 91%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 9 is selected from at least 25%. The abundance can also be at least 50%, and at least 75%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 11 -R 13 is selected from at least 33%. The abundance can also be at least 67%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 9 and R 11 -R 13 is selected from at least 14%. The abundance can also be at least 29%, at least 43%, at least 57%, at least 71%, at least 86%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 4 is selected from at least 33%. The abundance can also be at least 67%, and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 5 is 100%.
10 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 14 is selected from at least 6%. The abundance can also be at least 13%, at least 19%, at least 25%, at least 31%, at least 38%, at least 44%, at least 50%, at least 56%, at least 63%, at least 69%, at least 75%, at least 81%, at least 88%, at least 91 %, and 100%.
11 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-9 of Table 1.
12 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 10- 18 of Table 2.
13 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 17 are independently selected from H and D; and the abundance of deuterium in R 1 -R 17 is at least 6%.
14 . An isolated deuterium-enriched compound of claim 13 , wherein the compound is selected from compounds 1-9 of Table 1.
15 . An isolated deuterium-enriched compound of claim 13 , wherein the compound is selected from compounds 10-18 of Table 2.
16 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 17 are independently selected from H and D; and the abundance of deuterium in R 1 -R 17 is at least 6%.
17 . A mixture of deuterium-enriched compounds of claim 16 , wherein the compounds are selected from compounds 1-9 of Table 1.
18 . A mixture of deuterium-enriched compounds of claim 16 , wherein the compounds are selected from compounds 10-18 of Table 2.
19 . 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.
20 . A method for treating a disease selected from depression, anxiety, obsessive-compulsive disorder, post-traumatic stress disorder, premenstrual dysphoric disorder, panic disorder, and social phobia/social anxiety disorder 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.