DEUTERIUM-ENRICHED MODAFINIL
The present application describes deuterium-enriched modafinil, 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 15 are independently selected from H and D; and the abundance of deuterium in R 1 -R 15 is at least 7%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 15 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%.
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 5 is selected from at least 33%, at least 67%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 10 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 15 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-5 of Table 1.
8 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 6-10 of Table 2.
9 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 15 are independently selected from H and D; and the abundance of deuterium in R 1 -R 15 is at least 7%.
10 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 1 -R 15 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%.
11 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 1 -R 2 is selected from at least 50% and 100%.
12 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 3 -R 5 is selected from at least 33%, at least 67%, and 100%.
13 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 6 -R 10 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
14 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 11 -R 15 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
15 . An isolated deuterium-enriched compound of claim 9 , wherein the compound is selected from compounds 1-5 of Table 1.
16 . An isolated deuterium-enriched compound of claim 9 , wherein the compound is selected from compounds 6-10 of Table 2.
17 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 15 are independently selected from H and D; and the abundance of deuterium in R 1 -R 15 is at least 7%.
18 . A mixture of deuterium-enriched compound of claim 17 , wherein the compound is selected from compounds 1-5 of Table 1.
19 . A mixture of deuterium-enriched compound of claim 17 , wherein the compound is selected from compounds 6-10 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 narcolepsy, obstructive sleep apnea/hypopnea, and/or shift work sleep 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.