DEUTERIUM-ENRICHED ELETRIPTAN
The present application describes deuterium-enriched eletriptan, 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 26 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 26 is at least 4%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 26 is selected from at least 4%, at least 8%, at least 12%, at least 15%, at least 19%, at least 23%, at least 27%, at least 31%, at least 35%, at least 38%, at least 42%, at least 46%, at least 50%, at least 54%, at least 58%, at least 62%, at least 65%, at least 69%, at least 73%, at least 77%, at least 81%, at least 85%, 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 20 -R 21 is selected from at least 50% and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 3 -R 5 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 2 -R 7 and R 15 -R 26 is selected from at least 6%, at least 11%, at least 17%, at least 22%, at least 28%, at least 33%, at least 39%, at least 44%, at least 50%, at least 56%, at least 61%, at least 67%, at least 72%, at least 78%, at least 83%, at least 89%, at least 94%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 and R 20 -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 1 and R 3 -R 5 is selected from at least 25%, at least 50%, at least 75%, and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 , R 2 -R 7 , and R 15 -R 26 is selected from at least 5%, at least 11%, at least 16%, at least 21%, at least 26%, at least 32%, at least 37%, at least 42%, at least 47%, at least 53%, at least 58%, at least 63%, at least 68%, at least 74%, at least 79%, at least 84%, at least 89%, at least 95%, and 100%.
10 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 20 -R 21 and R 3 -R 5 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
11 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 , R 20 -R 21 and R 3 -R 5 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
12 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-11 of Table 1.
13 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 12-22 of Table 2.
14 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 26 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 26 is at least 4%.
15 . An isolated deuterium-enriched compound of claim 14 , wherein the compound is selected from compounds 1-11 of Table 1.
16 . An isolated deuterium-enriched compound of claim 14 , wherein the compound is selected from compounds 12-22 of Table 2.
17 . 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%.
18 . A mixture of deuterium-enriched compounds of claim 17 , wherein the compounds are selected from compounds 1-11 of Table 1.
19 . A mixture of deuterium-enriched compounds of claim 17 , wherein the compounds are selected from compounds 12-22 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 migraine headaches 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.