DEUTERIUM-ENRICHED TENOFOVIR
The present application describes deuterium-enriched tenofovir, 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 14 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 14 is at least 7%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 14 is selected from at least 7%, at least 14%, at least 21%, at least 29%, at least 36%, at least 43%, at least 50%, at least 57%, at least 64%, at least 71%, at least 79%, at least 86%, at least 93%, 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 33%, at least 67%, and 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 5 -R 6 is selected from at least 50% and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 7 -R 12 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 13 -R 14 is selected from at least 50% and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-5 of Table 1:
8 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 6-10 of Table 2:
9 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 14 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 14 is at least 7%.
10 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 1 -R 14 is selected from at least 7%, at least 14%, at least 21%, at least 29%, at least 36%, at least 43%, at least 50%, at least 57%, at least 64%, at least 71%, at least 79%, at least 86%, at least 93%, and 100%.
11 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 1 -R 4 is selected from at least 33%, at least 67%, and 100%.
12 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 5 -R 6 is selected from at least 50% and 100%.
13 . An isolated deuterium-enriched compound of claim 9 , wherein the abundance of deuterium in R 7 -R 12 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 9 , wherein the abundance of deuterium in R 13 -R 14 is selected from at least 50% and 100%.
15 . An isolated deuterium-enriched compound of claim 9 , wherein the compound is selected from compounds 1-5 of Table 1:
16 . An isolated deuterium-enriched compound of claim 9 , wherein the compound is selected from compounds 6-10 of Table 2:
17 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 14 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 14 is at least 7%.
18 . A mixture of deuterium-enriched compounds of claim 17 , wherein the abundance of deuterium in R 1 -R 14 is selected from at least 7%, at least 14%, at least 21%, at least 29%, at least 36%, at least 43%, at least 50%, at least 57%, at least 64%, at least 71%, at least 79%, at least 86%, at least 93%, and 100%.
19 . A mixture of deuterium-enriched compounds of claim 17 , wherein the abundance of deuterium in R 1 -R 4 is selected from at least 33%, at least 67%, and 100%.
20 . A mixture of deuterium-enriched compounds of claim 17 , wherein the abundance of deuterium in R 5 -R 6 is selected from at least 50% and 100%.
21 . A mixture of deuterium-enriched compounds of claim 17 , wherein the abundance of deuterium in R 7 -R 12 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
22 . A mixture of deuterium-enriched compounds of claim 17 , wherein the abundance of deuterium in R 13 -R 14 is selected from at least 50% and 100%.
23 . A mixture of deuterium-enriched compounds of claim 17 , wherein the compound is selected from compounds 1-5 of Table 1:
24 . A mixture of deuterium-enriched compounds of claim 17 , wherein the compound is selected from compounds 6-10 of Table 2:
25 . 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.
26 . A method for treating a disease selected from HIV and/or hepatitis B 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.