DEUTERIUM-ENRICHED CETIRIZINE
The present application describes deuterium-enriched cetirizine, 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 25 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 25 is at least 4%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 25 is selected from at least 4%, at least 8%, at least 12%, at least 16%, at least 20%, at least 24%, at least 28%, at least 32%, at least 36%, at least 40%, at least 44%, at least 48%, at least 52%, at least 56%, at least 60%, at least 64%, at least 68%, at least 72%, at least 76%, at least 80%, at least 84%, at least 88%, at least 92%, at least 96%, and 100%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 is 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 3 is selected from at least 50% and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 16 , R 17 , and R 20 is selected from at least 33%, at least 66%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 18 , R 19 , and R 21 -R 24 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 4 -R 15 and R 25 is selected from at least 8%, at least 15%, at least 23%, at least 31%, at least 38%, at least 46%, at least 54%, at least 62%, at least 69%, at least 77%, at least 85%, at least 92%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 , R 2 , and R 3 is selected from at least 33%, at least 66, and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 , R 16 , R 17 , and R 20 is selected from at least 25%, at least 50%, at least 75%, and 100%.
10 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 , R 18 , R 19 , and R 21 -R 24 is selected from at least 14%, at least 29%, at least 43%, at least 57%, at least 71%, at least 86%, and 100%.
11 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 and R 4 -R 15 is selected from at least 7%, at least 14%, at least 21%, at least 29%, at least 36%, at least 43%, at least 50%, at least 57%, at least 64%, at least 71%, at least 79%, at least 86%, at least 93%, and 100%.
12 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 3 , R 16 -R 17 , and R 20 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 2 -R 3 , R 18 , R 19 , and R 21 -R 24 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%.
14 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 3 , R 4 -R 15 , and R 25 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%.
15 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-31 of Table 1.
16 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 32-62 of Table 2.
17 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 25 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 25 is at least 4%.
18 . An isolated deuterium-enriched compound of claim 17 , wherein the compound is selected from compounds 1-31 of Table 1.
19 . An isolated deuterium-enriched compound of claim 17 , wherein the compound is selected from compounds 32-62 of Table 2.
20 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 25 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 25 is at least 4%.
21 . A mixture of deuterium-enriched compounds of claim 20 , wherein the compounds are selected from compounds 1-31 of Table 1.
22 . A mixture of deuterium-enriched compounds of claim 20 , wherein the compounds are selected from compounds 32-62 of Table 2.
23 . 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.
24 . A method for treating a disease selected from allergies, hay fever, angioedema, and hives, 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.