DEUTERIUM-ENRICHED FEXOFENADINE
The present application describes deuterium-enriched fexofenadine, 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 39 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 39 is at least 7%, provided that when R 33 -R 38 are D, then at least one other R is D.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 39 is selected from at least 3%, provided that when R 33 -R 38 are D, then at least one other R is D. at least 5%, at least 10%, at least 15%, at least 21%, at least 26%, at least 31%, at least 36%, at least 41%, at least 46%, at least 51%, at least 56%, at least 62%, at least 67%, at least 72%, at least 77%, at least 82%, at least 87%, at least 92%, at least 97%, and 100%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 3 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 4 -R 8 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 9 -R 13 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 14 -R 21 and R 39 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%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 22 -R 28 is selected from at least 14%, at least 29%, at least 43%, at least 57%, at least 71%, at least 86%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 29 -R 32 is selected from at least 25%, at least 50%, at least 75%, and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-7 of Table 1.
10 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 8-14 of Table 2.
11 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 39 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 39 is at least 7%, provided that when R 33 -R 38 are D, then at least one other R is D.
12 . An isolated deuterium-enriched compound of claim 11 , wherein the abundance of deuterium in R 1 -R 39 is selected from at least 3%, provided that when R 33 -R 38 are D, then at least one other R is D. at least 5%, at least 10%, at least 15%, at least 21%, at least 26%, at least 31%, at least 36%, at least 41%, at least 46%, at least 51%, at least 56%, at least 62%, at least 67%, at least 72%, at least 77%, at least 82%, at least 87%, at least 92%, at least 97%, and 100%.
13 . An isolated deuterium-enriched compound of claim 11 , wherein the abundance of deuterium in R 1 -R 3 is selected from at least 33%, at least 67%, and 100%.
14 . An isolated deuterium-enriched compound of claim 11 , wherein the compound is selected from compounds I-7 of Table 1.
15 . An isolated deuterium-enriched compound of claim 11 , wherein the compound is selected from compounds 8-14 of Table 2.
16 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 39 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 39 is at least 7%, provided that when R 33 -R 38 are D, then at least one other R is D.
17 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds I-7 of Table 1.
18 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 8-14 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 allergies 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.