DEUTERIUM-ENRICHED SATAVAPTAN
The present application describes deuterium-enriched satavaptan, 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 42 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 42 is at least 2%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 42 is selected from at least 2%, at least 5%, at least 10%, at least 14%, at least 19%, at least 24%, at least 29%, at least 33%, at least 38%, at least 43%, at least 48%, at least 52%, at least 57%, at least 62%, at least 67%, at least 71%, at least 76%, at least 81%, at least 86%, at least 90%, at least 93%, at least 98%, and 100%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 is selected from at least 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 10 is selected from at least 11%, at least 22%, at least 33%, at least 44%, at least 56%, at least 67%, at least 78%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 11 -R 13 is selected from at least 33%, at least 67%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 43 -R 45 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 14 -R 15 and R 21 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 16 -R 20 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 22 -R 26 and R 39 -R 42 is selected from at least 11%, at least 22%, at least 33%, at least 44%, at least 56%, at least 67%, at least 78%, 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 38 is selected from at least 13%, at least 25%, at least 38%, at least 50%, at least 63%, at least 75%, at least 88%, 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 42 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 42 is at least 2%.
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 42 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 42 is at least 2%.
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 syndrome of inappropriate antidiuretic hormone secretion 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.