DEUTERIUM-ENRICHED MIGLUSTAT
The present application describes deuterium-enriched miglustat, 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 2 , are independently selected from H and D; and
the abundance of deuterium in R 1 -R 21 is at least 5%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 2 , is selected from at least 5%, at least 10%, at least 14%, at least 19%, at least 24%, at least 29%, at least 33%, at least 38%, at least 43%, at least 48%, at least 52%, (k) at least 57%, at least 62%, at least 67%, at least 71%, at least 76%, at least 81%, at least 86%, at least 90%, at least 95%, and 100%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 4 is selected from at least 25%, at least 50%, at least 75%, and 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 5 -R 12 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%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 13 -R 20 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%.
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 2 , are independently selected from H and D; and
the abundance of deuterium in R 1 -R 21 is at least 5%.
9 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 -R 21 is selected from at least 5%, at least 10%, at least 14%, at least 19%, at least 24%, at least 29%, at least 33%, at least 38%, at least 43%, at least 48%, at least 52%, (k) at least 57%, at least 62%, at least 67%, at least 71%, at least 76%, at least 81%, at least 86%, at least 90%, at least 95%, and 100%.
10 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 -R 4 is selected from at least 25%, at least 50%, at least 75%, and 100%.
11 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 5 -R 12 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%.
12 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 13 -R 20 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 . 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 2 , are independently selected from H and D; and
the abundance of deuterium in R 1 -R 21 is at least 5%.
16 . A mixture of deuterium-enriched compound of claim 15 , wherein the abundance of deuterium in R 1 -R 21 is selected from at least 5%, at least 10%, at least 14%, at least 19%, at least 24%, at least 29%, at least 33%, at least 38%, at least 43%, at least 48%, at least 52%, (k) at least 57%, at least 62%, at least 67%, at least 71%, at least 76%, at least 81%, at least 86%, at least 90%, at least 95%, and 100%.
17 . A mixture of deuterium-enriched compound of claim 15 , wherein the compound is selected from compounds I-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 Gaucher disease 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.