DEUTERIUM-ENRICHED ALFUZOSIN
The present application describes deuterium-enriched alfuzosin, 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 27 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 27 is at least 4%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 27 is selected from at least 4%, at least 7%, at least 15%, at least 22%, at least 30%, at least 37%, at least 44%, at least 52%, at least 59%, at least 67%, at least 74%, at least 81%, at least 89%, at least 96%, 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 21 is selected from 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 3 and R 21 is selected from at least 25%, at least 50%, at least 75%, and 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 4 -R 5 is selected from at least 50% and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 11 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 12 -R 14 is selected from at least 33%, at least 67%, and 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 15 -R 20 is selected from at least 17%, at least 33%, at least 50%, at least 67%, at least 83%, and 100%.
10 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 21 -R 27 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 compound is selected from compounds 1-9 of Table 1.
12 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 10-18 of Table 2.
13 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 27 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 27 is at least 4%.
14 . An isolated deuterium-enriched compound of claim 13 , wherein the compound is selected from compounds 1-9 of Table 1.
15 . An isolated deuterium-enriched compound of claim 13 , wherein the compound is selected from compounds 10-18 of Table 2.
16 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 27 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 27 is at least 4%.
17 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 1-9 of Table 1.
18 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 10-18 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 benign prostatic hyperplasia 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.