DEUTERIUM-ENRICHED ESZOPICLONE
The present application describes deuterium-enriched eszopiclone, 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 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 6 is 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 7 -R 14 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%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 7 -R 17 is selected from at least 9%, at least 18%, at least 27%, at least 36%, at least 45%, at least 56%, at least 64%, at least 73%, at least 82%, at least 91%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 15 -R 17 is selected from at least 33%, at least 67%, and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-10 of Table 1:
10 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 11-20 of Table 2:
11 . 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%.
12 . An isolated deuterium-enriched compound of claim 12 , wherein the abundance of deuterium in R 1 -R 17 is selected from at least 6%, 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%.
13 . An isolated deuterium-enriched compound of claim 12 , wherein the abundance of deuterium in R 1 -R 3 is selected from at least 33%, at least 67%, and 100%.
14 . An isolated deuterium-enriched compound of claim 12 , wherein the abundance of deuterium in R 4 -R 5 is selected from at least 50% and 100%.
15 . An isolated deuterium-enriched compound of claim 12 , wherein the abundance of deuterium in R 6 is 100%.
16 . An isolated deuterium-enriched compound of claim 12 , wherein the abundance of deuterium in R 7 -R 14 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%.
17 . An isolated deuterium-enriched compound of claim 12 , wherein the abundance of deuterium in R 7 -R 17 is selected from at least 9%, at least 18%, at least 27%, at least 36%, at least 45%, at least 56%, at least 64%, at least 73%, at least 82%, at least 91%, and 100%.
18 . An isolated deuterium-enriched compound of claim 12 , wherein the abundance of deuterium in R 15 -R 17 is selected from at least 33%, at least 67%, and 100%.
19 . An isolated deuterium-enriched compound of claim 12 , wherein the compound is selected from compounds 1-10 of Table 1:
20 . An isolated deuterium-enriched compound of claim 12 , wherein the compound is selected from compounds 11-20 of Table 2:
21 . 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%.
22 . A mixture of deuterium-enriched compound of claim 21 , wherein the abundance of deuterium in R 1 -R 17 is selected from at least 6%, 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%.
23 . A mixture of deuterium-enriched compound of claim 21 , wherein the abundance of deuterium in R 1 -R 3 is selected from at least 33%, at least 67%, and 100%.
24 . A mixture of deuterium-enriched compound of claim 21 , wherein the abundance of deuterium in R 4 -R 5 is selected from at least 50% and 100%.
25 . A mixture of deuterium-enriched compound of claim 21 , wherein the abundance of deuterium in R 6 is 100%.
26 . A mixture of deuterium-enriched compound of claim 21 , wherein the abundance of deuterium in R 7 -R 14 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%.
27 . A mixture of deuterium-enriched compound of claim 21 , wherein the abundance of deuterium in R 7 -R 17 is selected from at least 9%, at least 18%, at least 27%, at least 36%, at least 45%, at least 56%, at least 64%, at least 73%, at least 82%, at least 91%, and 100%.
28 . A mixture of deuterium-enriched compound of claim 21 , wherein the abundance of deuterium in R 15 -R 17 is selected from at least 33%, at least 67%, and 100%.
29 . A mixture of deuterium-enriched compound of claim 21 , wherein the compound is selected from compounds 1-10 of Table 1:
30 . A mixture of deuterium-enriched compound of claim 21 , wherein the compound is selected from compounds 11-20 of Table 2:
31 . 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.
32 . A method for treating insomnia 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.