DEUTERIUM-ENRICHED BROMFENAC
The present application describes deuterium-enriched bromfenac, 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 12 are independently selected from H and D; and the abundance of deuterium in R 1 -R 12 is at least 8%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 12 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%.
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 11 -R 12 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 11 -R 12 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 R4-R 7 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 8 -R 10 is selected from at least 33%, at least 67%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-6 of Table 1.
9 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 7-12 of Table 2.
10 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 12 are independently selected from H and D; and the abundance of deuterium in R 1 -R 12 is at least 8%.
11 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 1 -R 12 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%.
12 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 1 -R 3 is selected from at least 33%, at least 67%, and 100%.
13 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 11 -R 12 is selected from at least 50% and 100%.
14 . An isolated deuterium-enriched compound of claim 10 , wherein the compound is selected from compounds 1-6 of Table 1.
15 . An isolated deuterium-enriched compound of claim 10 , wherein the compound is selected from compounds 7-12 of Table 2.
16 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 12 are independently selected from H and D; and the abundance of deuterium in R 1 -R 12 is at least 8%.
17 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 1-6 of Table 1.
18 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 7-12 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 postoperative inflammation in patients who have undergone cataract extraction 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.