DEUTERIUM-ENRICHED PANTOPRAZOLE
The present application describes deuterium-enriched pantoprazole, 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 15 are independently selected from H and D; and the abundance of deuterium in R 1 -R 15 is at least 7%, provided that if any of R 8 -R 13 is D, then at least one of R 2 -R 7 is a D.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 15 is selected from at least 7%, at least 13%, at least 20%, at least 27%, at least 33%, at least 40%, at least 47%, at least 53%, at least 60%, at least 67%, at least 73%, at least 80%, at least 87%, at least 93%, and 100%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 is selected from 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 7 is selected from at least 50% and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 5 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 8 -R 15 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%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 and R 6 -R 7 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 1 -R 5 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 1 and R 8 -R 15 is selected from at least 11%, at least 22%, at least 33%, at least 44%, at least 56%, at least 67%, at least 78%, 100%.
10 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 7 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
11 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 15 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%.
12 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 5 and R 8 -R 15 is selected from at least 8%, at least 17%, at least 25%, at least 33%, at least 42%, at least 50%, at least 58%, at least 67%, at least 75%, at least 83%, at least 92%, and 100%.
13 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 4 is selected from at least 33%, at least 67%, and 100%.
14 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 5 is selected from 100%.
15 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 14 -R 15 is selected from at least 50% and 100%.
16 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-14 of Table 1.
17 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 15-28 of Table 2.
18 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 15 are independently selected from H and D; and the abundance of deuterium in R 1 -R 15 is at least 7%, provided that if any of R 8 -R 13 is D, then at least one of R 2 -R 7 is a D.
19 . An isolated deuterium-enriched compound of claim 18 , wherein the compound is selected from compounds 1-14 of Table 1.
20 . An isolated deuterium-enriched compound of claim 18 , wherein the compound is selected from compounds 15-28 of Table 2.
21 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 15 are independently selected from H and D; and the abundance of deuterium in R 1 -R 15 is at least 7%, provided that if any of R 8 -R 13 is D, then at least one of R 2 -R 7 is a D.
22 . A mixture of deuterium-enriched compound of claim 21 , wherein the compound is selected from compounds 1-14 of Table 1.
23 . A mixture of deuterium-enriched compound of claim 21 , wherein the compound is selected from compounds 15-28 of Table 2.
24 . 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.
25 . A method for treating gastroesophageal reflux disease 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.