DEUTERIUM-ENRICHED ODIPARCIL
The present application describes deuterium-enriched odiparcil, 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 16 are independently selected from H and D; and the abundance of deuterium in R 1 -R 16 is at least 6%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 16 is selected from at least 6%. The abundance can also be (a) at least 13%, (b) at least 19%, (c) at least 25%,(d) at least 31%, (e) at least 38%, (f) at least 44%, (g) at least 50%, (h) at least 56%, (i) at least 63%, (j) at least 69%, (k) at least 75%, (l) at least 81%, (m) at least 88%, (n) at least 94%, and (o) 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%. The abundance can also be (a) at least 67%, and (b) 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 13 -R 16 is selected from at least 33%. The abundance can also be (a) at least 67%, and (b) 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 3 and R 13 -R 16 is at least 17%. The abundance can also be (a) at least 33%, (b) at least 50%, (c) at least 67%, (d) at least 83%, and (e) 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 4 -R 9 is at least 17%. The abundance can also be (a) at least 33%, (b) at least 50%, (c) at least 67%, (d) at least 83%, and (e) 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 10 -R 12 is selected from at least 33%. The abundance can also be (a) at least 67%, and (b) 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 13 -R 15 is selected from at least 33%. The abundance can also be (a) at least 67%, and (b) 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 16 is selected from 100%.
10 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-8 of Table 1.
11 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 9-16 of Table 2.
12 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 16 are independently selected from H and D; and the abundance of deuterium in R 1 -R 16 is at least 6%.
13 . An isolated deuterium-enriched compound of claim 12 , wherein the abundance of deuterium in R 1 -R 16 is selected from at least 6%. The abundance can also be (a) at least 13%, (b) at least 19%, (c) at least 25%,(d) at least 31%, (e) at least 38%, (f) at least 44%, (g) at least 50%, (h) at least 56%, (i) at least 63%, (j) at least 69%, (k) at least 75%, (l) at least 81%, (m) at least 88%, (n) at least 94%, and (o) 100%.
14 . An isolated deuterium-enriched compound of claim 12 , wherein the compound is selected from compounds 1-8 of Table 1.
15 . An isolated deuterium-enriched compound of claim 12 , wherein the compound is selected from compounds 9-16 of Table 2.
16 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 16 are independently selected from H and D; and the abundance of deuterium in R 1 -R 16 is at least 6%.
17 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 1-8 of Table 1.
18 . A mixture of deuterium-enriched compound of claim 16 , wherein the compound is selected from compounds 9-16 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 prevention of venous thromboembolism 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.