DEUTERIUM-ENRICHED LEVETIRACETAM
The present application describes deuterium-enriched levetiracetam, 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 14 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 14 is at least 7%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 14 is selected from at least 7%, at least 14%, at least 21%, at least 29%, at least 36%, at least 43%, at least 50%, at least 57%, at least 64%, at least 71%, at least 79%, at least 86%, at least 93%, and 100%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 2 is selected from at least 50% and 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 3 -R 8 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 9 -R 14 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-4 of Table 1.
7 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 5-8 of Table 2.
8 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 14 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 14 is at least 7%.
9 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 -R 14 is selected from at least 7%, at least 14%, at least 21%, at least 29%, at least 36%, at least 43%, at least 50%, at least 57%, at least 64%, at least 71%, at least 79%, at least 86%, at least 93%, and 100%.
10 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 -R 2 is selected from at least 50% and 100%.
11 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 3 -R 8 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
12 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 9 -R 14 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
13 . An isolated deuterium-enriched compound of claim 8 , wherein the compound is selected from compounds 1-4 of Table 1.
14 . An isolated deuterium-enriched compound of claim 8 , wherein the compound is selected from compounds 5-8 of Table 2.
15 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 14 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 14 is at least 7%.
16 . A mixture of deuterium-enriched compound of claim 15 , wherein the abundance of deuterium in R 1 -R 14 is selected from at least 7%, at least 14%, at least 21%, at least 29%, at least 36%, at least 43%, at least 50%, at least 57%, at least 64%, at least 71%, at least 79%, at least 86%, at least 93%, and 100%.
17 . A mixture of deuterium-enriched compound of claim 15 , wherein the compound is selected from compounds 1-4 of Table 1.
18 . A mixture of deuterium-enriched compound of claim 15 , wherein the compound is selected from compounds 5-8 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 epilepsy 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.