DEUTERIUM-ENRICHED VINFLUNINE
The present application describes deuterium-enriched vinflunine, 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 54 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 54 is at least 2%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 54 is selected from at least 2%, at least 4%, at least 10%, at least 16%, at least 22%, at least 27%, at least 33%, at least 39%, at least 45%, at least 51%, at least 57%, at least 63%, at least 69%, at least 75%, at least 80%, at least 86%, at least 92%, at least 98%, 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 33%, at least 67%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 9 -R 19 is selected from at least 9%, at least 18%, at least 27%, at least 36%, at least 45%, at least 56%, at least 64%, at least 73%, at least 82%, at least 91%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 22 -R 24 is selected from at least 33%, at least 67%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 25 -R 27 is selected from at least 33%, at least 67%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 28 and R 54 is selected from at least 50% and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 29 -R 31 is selected from at least 33%, at least 67%, and 100%.
10 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 33 -R 35 is selected from at least 33%, at least 67%, and 100%.
11 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 37 -R 39 is selected from at least 33%, at least 67%, and 100%.
12 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 20 -R 44 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
13 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 32 , R 36 , and R 4 5 -R 52 is selected from at least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, and 100%.
14 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-12 of Table 1.
15 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 13-24 of Table 2.
16 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 54 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 54 is at least 2%.
17 . An isolated deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 1-12 of Table 1.
18 . An isolated deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 13-24 of Table 2.
19 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 54 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 54 is at least 2%.
20 . A mixture of deuterium-enriched compound of claim 19 , wherein the compound is selected from compounds 1-12 of Table 1.
21 . A mixture of deuterium-enriched compound of claim 19 , wherein the compound is selected from compounds 13-24 of Table 2.
22 . 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.
23 . 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.