DEUTERIUM-ENRICHED GABAPENTIN
The present application describes deuterium-enriched gabapentin, 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 6%.
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 8%, 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 -R 3 is selected from at least 33%, at least 67%, and 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 4 -R 5 is selected from at least 50%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 3 and R 4 -R 5 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 abundance of deuterium in R 1 -R 3 and R 6 -R 17 is selected from at least 7%, at least 13%, at least 20%, at least 27%, at least 33%, at least 40%, at least 47%, at least 53%, at least 60%, at least 67%, at least 73%, at least 80%, at least 87%, at least 93%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 4 -R 5 and R 6 -R 17 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%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 17 is selected from at least 8%, at least 17%, at least 25%, at least 33%, at least 42%, at least 50%, at least 58%, at least 67%, at least 75%, at least 83%, at least 92%, and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 7 is selected from at least 50% and 100%.
10 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 8 -R 17 is selected from at least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, and 100%.
11 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 7 and R 12 -R 15 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
12 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 10 -R 17 is selected from at least 13%, at least 25%, at least 38%, at least 50%, at least 63%, at least 75%, at least 88%, and 100%.
13 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 10 -R 11 and R 16 -R 17 is selected from at least 25%, at least 50%, at least 75%, and 100%.
14 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 12 -R 15 is selected from at least 25%, at least 50%, at least 75%, and 100%.
15 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 7 and R 8 -R 9 is selected from at least 25%, at least 50%, at least 75%, and 100%.
16 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 8 -R 9 is selected from at least 50% and 100%.
17 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-15 of Table 1.
18 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 16-30 of Table 2.
19 . 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%.
20 . An isolated deuterium-enriched compound of claim 19 , wherein the compound is selected from compounds 1-15 of Table 1.
21 . An isolated deuterium-enriched compound of claim 19 , wherein the compound is selected from compounds 16-30 of Table 2.
22 . 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%.
23 . A mixture of deuterium-enriched compounds of claim 22 , wherein the compounds are selected from compounds 1- 15 of Table 1.
24 . A mixture of deuterium-enriched compounds of claim 22 , wherein the compounds are selected from compounds 16-30 of Table 2.
25 . 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.
26 . 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.