Deuterium-enriched oxybutynin
The present application describes deuterium-enriched oxybutynin, 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 31 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 31 is at least 3% provided that the compound is other than:
a compound where only each of R 22-31 is D or a compound where only each of R 20-21 is D.
2. A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 31 is selected from at least 3%, at least 6%, at least 13%, 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 is 100%.
4. A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 , R 20 -R 21 , and R 22 -R 31 is selected from at least 8%, at least 15%, at least 23%, 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 20 -R 21 and R 22 -R 31 is selected from at least 8%, at least 17%, at least 25%, at least 33% at least 42%, at least 50%, at least 58%, at least 67%, at least 75%, at least 83%, at least 92%, and 100%.
6. A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 2 -R 6 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
7. A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 7 -R 17 is selected from at least 9%, at least 18%, at least 27%, at least 36%, at least 45% at least 56%, at least 64%, at least 73%, at least 82%, at least 91%, and 100%.
8. A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-8 of Table 1:
1
2
3
4
5
6
7
8
9. A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 9-16 of Table 2:
9
10
11
12
13
14
15
16
10. An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 31 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 31 is at least 3% provided that the compound is other than:
a compound where only each of R 22-31 is D or a compound where only each of R 20-21 is D.
11. An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 1 -R 31 is selected from at least 3%, at least 6%, at least 13%, 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 10 , wherein the abundance of deuterium in R 1 is 100%.
13. An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 1 , R 20 -R 21 , and R 22 -R 31 is selected from at least 8%, at least 15%, at least 23%, 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%.
14. An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 20 -R 21 and R 22 -R 31 is selected from at least 8%, at least 17%, at least 25%, at least 33%, at least 42%, at least 50%, at least 58%, at least 67%, at least 75%, at least 83%, at least 92%, and 100%.
15. An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 2 -R 5 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
16. An isolated deuterium-enriched compound of claim 10 , wherein the abundance of deuterium in R 7 -R 17 is selected from at least 9%, at least 18%, at least 27%, at least 36%, at least 45%, at least 56%, at least 64%, at least 73% at least 82%, at least 91%, and 100%.
17. An isolated deuterium-enriched compound of claim 10 , wherein the compound is selected from compounds 1-8 of Table 1:
1
2
3
4
5
6
7
8
18. An isolated deuterium-enriched compound of claim 10 , wherein the compound is selected from compounds 9-16 of Table 2:
9
10
11
12
13
14
15
16
19. A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 31 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 31 is at least 3% provided that the compound is other than:
a compound where only each of R 22-31 is D or a compound where only each of R 20-21 is D.
20. A mixture of deuterium-enriched compound of claim 19 , wherein the abundance of deuterium in R 1 -R 31 is selected from at least 3%, at least 6%, at least 13%, 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%.
21. A mixture of deuterium-enriched compound of claim 19 , wherein the abundance of deuterium in R 1 is 100%.
22. A mixture of deuterium-enriched compound of claim 19 , wherein the abundance of deuterium in R 1 , R 20 -R 21 , and R 22 -R 31 is selected from at least 8%, at least 15%, at least 23%, 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%.
23. A mixture of deuterium-enriched compound of claim 19 , wherein the abundance of deuterium in R 20 -R 21 and R 22 -R 31 is selected from at least 8%, at least 17%, at least 25%, at least 33%, at least 42%, at least 50%, at least 58%, at least 67%, at least 75%, at least 83%, at least 92%, and 100%.
24. A mixture of deuterium-enriched compound of claim 19 , wherein the abundance of deuterium in R 2 -R 6 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
25. A mixture of deuterium-enriched compound of claim 19 , wherein the abundance of deuterium in R 7 -R 17 is selected from at least 9%, at least 18%, at least 27%, at least 36%, at least 45% at least 56%, at least 64%, at least 73%, at least 82%, at least 91%, and 100%.
26. A mixture of deuterium-enriched compounds of claim 19 , wherein the compounds are selected from compounds 1-8 of Table 1:
1
2
3
4
5
6
7
8
27. A mixture of deuterium-enriched compounds of claim 19 , wherein the compounds are selected from compounds 9-16 of Table 2:
9
10
11
12
13
14
15
16
28. 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.