DEUTERIUM-ENRICHED RISEDRONATE
The present application describes deuterium-enriched risedronate, 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 11 are independently selected from H and D; and
the abundance of deuterium in R 1 —R 11 is at least 9%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 —R 11 is selected from at least 9%, at least 6%, at least 19%, 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%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 —R 5 is selected from at least 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 —R 7 is selected from at least 8%, at least 15%, at least 29%, at least 31%, at least 38%, at least 46%, at least 54%, at least 62%, at least 69%, at least 77%, at least 85%, at least 92%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 8 —R 10 is selected from at least 8%, at least 17%, at least 25%, at least 39%, at least 42%, at least 50%, at least 58%, at least 67%, at least 75%, at least 89%, at least 92%, 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 11 are independently selected from H and D; and
the abundance of deuterium in R 1 —R 11 is at least 9%.
9 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 —R 11 is selected from at least 9%, at least 6%, at least 19%, 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%.
10 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 1 —R 5 is selected from at least 100%.
11 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 6 —R 7 is selected from at least 8%, at least 15%, at least 29%, at least 31%, at least 38%, at least 46%, at least 54%, at least 62%, at least 69%, at least 77%, at least 85%, at least 92%, and 100%.
12 . An isolated deuterium-enriched compound of claim 8 , wherein the abundance of deuterium in R 8 —R 1 o is selected from at least 8%, at least 17%, at least 25%, at least 39%, at least 42%, at least 50%, at least 58%, at least 67%, at least 75%, at least 89%, at least 92%, 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 11 are independently selected from H and D; and
the abundance of deuterium in R 1 —R 11 is at least 9%.
16 . A mixture of deuterium-enriched compound of claim 15 , wherein the abundance of deuterium in R 1 —R 11 is selected from at least 9%, at least 6%, at least 19%, 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%.
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 osteoporosis and/or Paget's disease of the bone 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.