DEUTERIUM-ENRICHED CICLESONIDE
The present application describes deuterium-enriched ciclesonide, 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 44 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 44 is at least 2%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 44 is selected from at least 2%, at least 5%, at least 9%, at least 14%, at least 18%, at least 23%, at least 27%, at least 32%, at least 36%, at least 41%, at least 45%, at least 50%, at least 55%, at least 59%, at least 64%, at least 68%, at least 73%, at least 77%, at least 80%, at least 84%, at least 89%, at least 93%, at least 97%, 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 15 -R 17 and R 43 -R 44 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 18 -R 35 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%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 17 -R 23 is selected from at least 14%, at least 29%, at least 43%, at least 57%, at least 71%, at least 86%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 25 -R 35 is selected from at least 9%, at least 18%, at least 27%, at least 36%, at least 45%, at least 56%, at least 64%, at least 73%, at least 82%, at least 91%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-6 of Table 1.
9 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 7-12 of Table 2.
10 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 44 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 44 is at least 2%.
11 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 1 -R 44 is selected from at least 2%, at least 5%, at least 9%, at least 14%, at least 18%, at least 23%, at least 27%, at least 32%, at least 36%, at least 41%, at least 45%, at least 50%, at least 55%, at least 59%, at least 64%, at least 68%, at least 73%, at least 77%, at least 80%, at least 84%, at least 89%, at least 93%, at least 97%, and 100%.
12 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 1 is selected from 100%.
13 . An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 15 -R 17 and R 43 -R 44 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
14 . An isolated deuterium-enriched compound of claim 10 , wherein the compound is selected from compounds I-6 of Table 1.
15 . An isolated deuterium-enriched compound of claim 10 , wherein the compound is selected from compounds 7-12 of Table 2.
16 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 44 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 44 is at least 2%.
17 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 1-6 of Table 1.
18 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 7-12 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 persistent asthma 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.