DEUTERIUM-ENRICHED FENOFIBRATE
The present application describes deuterium-enriched fenofibrate, 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 21 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 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%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 7 is selected from at least 14%, at least 29%, at least 43%, at least 57%, at least 71%, at least 86%, and 100%.
4 . deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 8 -R 13 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 14 -R 17 is selected from at least 25%, at least 50%, at least 75%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 18 -R 21 is selected from at least 25%, at least 50%, at least 75%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 13 is selected from at least 8%, at least 15%, at least 23%, at least 31%, at least 38%, at least 46%, at least 54%, at least 62%, at least 69%, at least 77%, at least 85%, at least 92%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-14 of Table 1:
9 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 15-28 of Table 2:
10 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 21 are independently selected from H and D; and the abundance of deuterium in R 1 -R 21 is at least 5%.
11 . An isolated deuterium-enriched compound of claim 10 , 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%.
12 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 1 -R 7 is selected from at least 14%, at least 29%, at least 43%, at least 57%, at least 71%, at least 86%, and 100%.
13 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 8 -R 13 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
14 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 14 -R 17 is selected from at least 25%, at least 50%, at least 75%, and 100%.
15 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 18 -R 21 is selected from at least 25%, at least 50%, at least 75%, and 100%.
16 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 1 -R 13 is selected from at least 8%, at least 15%, at least 23%, at least 31%, at least 38%, at least 46%, at least 54%, at least 62%, at least 69%, at least 77%, at least 85%, at least 92%, and 100%.
17 . An isolated deuterium-enriched compound of claim 10 , wherein the compound is selected from compounds 1-14 of Table 1:
18 . An isolated deuterium-enriched compound of claim 10 , wherein the compound is selected from compounds 15-28 of Table 2:
19 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 21 are independently selected from H and D; and the abundance of deuterium in R 1 -R 21 is at least 5%.
20 . A mixture of deuterium-enriched compound of claim 37 , 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%.
21 . A mixture of deuterium-enriched compound of claim 37 , wherein the abundance of deuterium in R 1 -R 7 is selected from at least 14%, at least 29%, at least 43%, at least 57%, at least 71%, at least 86%, and 100%.
22 . A mixture of deuterium-enriched compound of claim 37 , wherein the abundance of deuterium in R 8 -R 13 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
23 . A mixture of deuterium-enriched compound of claim 37 , wherein the abundance of deuterium in R 14 -R 17 is selected from at least 25%, at least 50%, at least 75%, and 100%.
24 . A mixture of deuterium-enriched compound of claim 37 , wherein the abundance of deuterium in R 18 -R 21 is selected from at least 25%, at least 50%, at least 75%, and 100%.
25 . A mixture of deuterium-enriched compound of claim 37 , wherein the abundance of deuterium in R 1 -R 13 is selected from at least 8%, at least 15%, at least 23%, at least 31%, at least 38%, at least 46%, at least 54%, at least 62%, at least 69%, at least 77%, at least 85%, at least 92%, and 100%.
26 . A mixture of deuterium-enriched compound of claim 37 , wherein the compound is selected from compounds 1 - 14 of Table 1:
27 . A mixture of deuterium-enriched compound of claim 37 , wherein the compound is selected from compounds 15-28 of Table 2:
28 . 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.
29 . A method for treating a disease selected from hypercholesterolemia, hypertriglyceridemia, and cardiovascular 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.