DEUTERIUM-ENRICHED TIPRANAVIR
The present application describes deuterium-enriched tipranavir, 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 33 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 33 is at least 3%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 33 is selected from at least 3%, at least 6%, at least 12%, at least 18%, at least 24%, at least 30%, at least 36%, at least 42%, at least 48%, at least 55%, at least 61%, at least 67%, at least 73%, at least 79%, at least 85%, at least 91%, at least 94%, 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 19 -R 20 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 2 and R 19 -R 20 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 3 -R 7 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 abundance of deuterium in R 8 -R 11 is selected from at least 25%, at least 50%, at least 75%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 12 -R 17 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 21 -R 26 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
10 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 27 -R 30 is selected from at least 25%, at least 50%, at least 75%, and 100%.
11 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 31 -R 33 is selected from at least 33%, at least 67%, and 100%.
12 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-10 of Table 1.
13 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 11-20 of Table 2.
14 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 33 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 33 is at least 3%.
15 . An isolated deuterium-enriched compound of claim 14 , wherein the compound is selected from compounds 1-10 of Table 1.
16 . An isolated deuterium-enriched compound of claim 14 , wherein the compound is selected from compounds 11-20 of Table 2.
17 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 33 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 33 is at least 3%.
18 . A mixture of deuterium-enriched compound of claim 17 , wherein the compound is selected from compounds 1-10 of Table 1.
19 . A mixture of deuterium-enriched compound of claim 17 , wherein the compound is selected from compounds 11-20 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 Human immunodeficiency virus infection 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.