DEUTERIUM-ENRICHED MOXIFLOXACIN
The present application describes deuterium-enriched moxifloxacin, 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 24 are independently selected from H and D; and the abundance of deuterium in R 1 —R 24 is at least 4%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 —R 24 is selected from at least 4%, at least 8%, at least 13%, at least 17%, at least 21%, at least 25%, at least 29%, at least 33%, at least 38%, at least 42%, at least 46%, at least 50%, at least 54%, at least 58%, at least 63%, at least 67%, at least 71%, at least 75%, at least 79%, at least 83%, at least 88%, at least 92%, at least 96%, 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 14 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%.
5 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 15 is selected from 100%.
6 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 16 —R 18 is selected from at least 33%, at least 67%, and 100%.
7 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 19 —R 23 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
8 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 24 is selected from 100%.
9 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-7 of Table 1:
10 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 8-14 of Table 2:
11 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 —R 24 are independently selected from H and D; and the abundance of deuterium in R 1 —R 24 is at least 4%.
12 . An isolated deuterium-enriched compound of claim 11 , wherein the abundance of deuterium in R 1 —R 24 is selected from at least 4%, at least 8%, at least 13%, at least 17%, at least 21%, at least 25%, at least 29%, at least 33%, at least 38%, at least 42%, at least 46%, at least 50%, at least 54%, at least 58%, at least 63%, at least 67%, at least 71%, at least 75%, at least 79%, at least 83%, at least 88%, at least 92%, at least 96%, and 100%.
13 . An isolated deuterium-enriched compound of claim 11 , wherein the abundance of deuterium in R 1 —R 2 is selected from at least 50% and 100%.
14 . An isolated deuterium-enriched compound of claim 11 , wherein the abundance of deuterium in R 3 —R 14 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 11 , wherein the abundance of deuterium in R 15 is selected from 100%.
16 . An isolated deuterium-enriched compound of claim 11 , wherein the abundance of deuterium in R 16 —R 18 is selected from at least 33%, at least 67%, and 100%.
17 . An isolated deuterium-enriched compound of claim 11 , wherein the abundance of deuterium in R 19 —R 23 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
18 . An isolated deuterium-enriched compound of claim 11 , wherein the abundance of deuterium in R 24 is selected from 100%.
19 . An isolated deuterium-enriched compound of claim 11 , wherein the compound is selected from compounds 1-7 of Table 1:
20 . An isolated deuterium-enriched compound of claim 11 , wherein the compound is selected from compounds 8-14 of Table 2:
21 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 —R 24 are independently selected from H and D; and the abundance of deuterium in R 1 —R 24 is at least 4%.
22 . A mixture of deuterium-enriched compounds of claim 21 , wherein the abundance of deuterium in R 1 —R 24 is selected from at least 4%, at least 8%, at least 13%, at least 17%, at least 21%, at least 25%, at least 29%, at least 33%, at least 38%, at least 42%, at least 46%, at least 50%, at least 54%, at least 58%, at least 63%, at least 67%, at least 71%, at least 75%, at least 79%, at least 83%, at least 88%, at least 92%, at least 96%, and 100%.
23 . A mixture of deuterium-enriched compounds of claim 21 , wherein the abundance of deuterium in R 1 —R 2 is selected from at least 50% and 100%.
24 . A mixture of deuterium-enriched compounds of claim 21 , wherein the abundance of deuterium in R 3 —R 14 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%.
25 . A mixture of deuterium-enriched compounds of claim 21 , wherein the abundance of deuterium in R 15 is selected from 100%.
26 . A mixture of deuterium-enriched compounds of claim 21 , wherein the abundance of deuterium in R 16 —R 18 is selected from at least 33%, at least 67%, and 100%.
27 . A mixture of deuterium-enriched compounds of claim 21 , wherein the abundance of deuterium in R 19 —R 23 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
28 . A mixture of deuterium-enriched compounds of claim 21 , wherein the abundance of deuterium in R 24 is selected from 100%.
29 . A mixture of deuterium-enriched compounds of claim 21 , wherein the compound is selected from compounds 1-7 of Table 1:
30 . A mixture of deuterium-enriched compounds of claim 21 , wherein the compound is selected from compounds 8-14 of Table 2:
31 . 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.
32 . A method for treating a disease selected from acute sinusitis, acute exacerbations of chronic bronchitis and community-acquired pneumonia, skin structure infections, complicated intra-abdominal infections, and conjunctival infections 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.