DEUTERIUM-ENRICHED FLUTICASONE PROPIONATE
The present application describes deuterium-enriched fluticasone propionate, 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 8 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 8 is at least 13%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 8 is selected from (a) at least 25%, (b) at least 38%, (c) at least 50%, (d) at least 63%, (e) at least 75%, (f) at least 88%, and (g) 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 (a) at least 50% and (b) 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 4 -R 8 is selected from (a) at least 20%, (b) at least 40%, (c) at least 60%, (d) at least 80%, and (e) 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-4 of Table 1:
7 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 5-8 of Table 2:
8 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 8 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 8 is at least 13%.
9 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 -R 8 is selected from (a) at least 25%, (b) at least 38%, (c) at least 50%, (d) at least 63%, (e) at least 75%, (f) at least 88%, and (g) 100%%.
10 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 is 100%.
11 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 2 -R 3 is selected from (a) at least 50% and (b) 100%.
12 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 4 -R 9 is selected from (a) at least 20%, (b) at least 40%, (c) at least 60%, (d) at least 80%, and (e) 100%.
13 . An isolated deuterium-enriched compound of claim 8 , wherein the compound is selected from compounds 1-4 of Table 1:
14 . An isolated deuterium-enriched compound of claim 8 , wherein the compound is selected from compounds 5-8 of Table 2:
15 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 8 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 8 is at least 13%.
16 . A mixture of deuterium-enriched compound of claim 15 , wherein the abundance of deuterium in R 1 -R 5 is selected from (a) at least 25%, (b) at least 38%, (c) at least 50%, (d) at least 63%, (e) at least 75%, (f) at least 88%, and (g) 100%%.
17 . A mixture of deuterium-enriched compound of claim 15 , wherein the abundance of deuterium in R 1 is 100%.
18 . A mixture of deuterium-enriched compound of claim 15 , wherein the abundance of deuterium in R 2 -R 3 is selected from (a) at least 50% and (b) 100%.
19 . A mixture of deuterium-enriched compound of claim 15 , wherein the abundance of deuterium in R 4 -R 8 is selected from (a) at least 20%, (b) at least 40%, (c) at least 60%, (d) at least 80%, and (e) 100%.
20 . A mixture of deuterium-enriched compound of claim 15 , wherein the compound is selected from compounds I-4 of Table 1:
21 . A mixture of deuterium-enriched compound of claim 15 , wherein the compound is selected from compounds 5-8 of Table 2:
22 . 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.
23 . A method for treating a disease selected from asthma, allergic rhinitis, eczema, and psoriasis 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.