DEUTERIUM-ENRICHED FINASTERIDE
The present application describes deuterium-enriched finasteride, 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 36 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 36 is at least 3%, provided that when R 34 -R 36 are D, then at least one other R is D.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 36 is selected from at least 3%, provided that when R 34 -R 36 are D, then at least one other R is D. The abundance can also be 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%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 2 is selected from at least 50% and 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 3 -R 16 and R 26 -R 36 is selected from at least 4%, at least 6%, at least 14%, at least 19%, at least 26%, at least 32%, at least 39%, at least 45%, at least 52%, at least 58%, at least 65%, at least 71%, at least 77%, at least 84%, at least 90%, at least 97%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 17 -R 25 is selected from at least 11%, at least 22%, at least 33%, at least 44%, at least 56%, at least 67%, at least 78%, and 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 36 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 36 is at least 3%, provided that when R 34 -R 36 are D, then at least one other R is D.
9 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 -R 36 is selected from at least 3%, provided that when R 34 -R 36 are D, then at least one other R is D. The abundance can also be 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%.
10 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 -R 2 is selected from at least 50% and 100%.
11 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 3 -R 16 and R 26 -R 36 is selected from at least 4%, at least 6%, at least 14%, at least 19%, at least 26%, at least 32%, at least 39%, at least 45%, at least 52%, at least 58%, at least 65%, at least 71%, at least 77%, at least 84%, at least 90%, at least 97%, and 100%.
12 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 17 -R 25 is selected from at least 11%, at least 22%, at least 33%, at least 44%, at least 56%, at least 67%, at least 78%, and 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 36 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 36 is at least 3%, provided that when R 34 -R 36 are D, then at least one other R is D.
16 . A mixture of deuterium-enriched compound of claim 15 , wherein the abundance of deuterium in R 1 -R 36 is selected from at least 3%, provided that when R 34 -R 36 are D, then at least one other R is D. The abundance can also be 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%.
17 . A mixture of deuterium-enriched compound of claim 15 , wherein the compound is selected from compounds 1-4 of Table 1.
18 . A mixture of deuterium-enriched compound of claim 15 , wherein the compound is selected from compounds 5-8 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 a disease selected from benign prostatic hyperplasia and/or prostate cancer 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.