DEUTERIUM-ENRICHED TIRAPAZAMINE
The present application describes deuterium-enriched tirapazamine, 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 6 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 6 is at least 17%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 6 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, 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 3 -R 6 is selected from at least 25%, at least 50%, at least 75%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-3 of Table 1.
6 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 4-6 of Table 2.
7 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 6 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 6 is at least 17%.
8 . An isolated deuterium-enriched compound of claim 7 , wherein the abundance of deuterium in R 1 -R 6 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
9 . An isolated deuterium-enriched compound of claim 7 , wherein the abundance of deuterium in R 1 -R 2 is selected from at least 50% and 100%.
10 . An isolated deuterium-enriched compound of claim 7 , wherein the abundance of deuterium in R 3 -R 6 is selected from at least 25%, at least 50%, at least 75%, and 100%.
11 . An isolated deuterium-enriched compound of claim 7 , wherein the compound is selected from compounds 1-3 of Table 1.
12 . An isolated deuterium-enriched compound of claim 7 , wherein the compound is selected from compounds 4-6 of Table 2.
13 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 6 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 6 is at least 17%.
14 . A mixture of deuterium-enriched compound of claim 13 , wherein the abundance of deuterium in R 1 -R 6 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
15 . A mixture of deuterium-enriched compound of claim 13 , wherein the abundance of deuterium in R 1 -R 2 is selected from at least 50% and 100%.
16 . A mixture of deuterium-enriched compound of claim 13 , wherein the abundance of deuterium in R 3 -R 6 is selected from at least 25%, at least 50%, at least 75%, and 100%.
17 . A mixture of deuterium-enriched compound of claim 13 , wherein the compound is selected from compounds 1-3 of Table 1.
18 . A mixture of deuterium-enriched compound of claim 13 , wherein the compound is selected from compounds 4-6 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 cancer 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.