DEUTERIUM-ENRICHED AZITHROMYCIN
The present application describes deuterium-enriched azithromycin, 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 13 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 13 is at least 8%.
2 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 13 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%.
3 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 1 -R 5 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
4 . A deuterium-enriched compound of claim 1 , wherein the abundance of deuterium in R 6 -R 13 is selected from at least 13%, at least 25%, at least 38%, at least 50%, at least 63%, at least 75%, at least 88%, and 100%.
5 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 1-3 of Table 1:
6 . A deuterium-enriched compound of claim 1 , wherein the compound is selected from compounds 4-6 of Table 2:
7 . An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 13 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 13 is at least 8%.
8 . An isolated deuterium-enriched compound of claim 7 , wherein the abundance of deuterium in R 1 -R 13 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%.
9 . An isolated deuterium-enriched compound of claim 7 , wherein the abundance of deuterium in R 1 -R 5 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
10 . An isolated deuterium-enriched compound of claim 7 , wherein the abundance of deuterium in R 6 -R 13 is selected from at least 13%, at least 25%, at least 38%, at least 50%, at least 63%, at least 75%, at least 88%, and 100%.
11 . An isolated deuterium-enriched compound of claim 7 , wherein the compound is selected from compounds 1-3 of Table 1:
12 . An isolated deuterium-enriched compound of claim 7 , wherein the compound is selected from compounds 4-6 of Table 2:
13 . A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof:
wherein R 1 -R 13 are independently selected from H and D; and
the abundance of deuterium in R 1 -R 13 is at least 8%.
14 . A mixture of deuterium-enriched compound of claim 13 , wherein the abundance of deuterium in R 1 -R 13 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%.
15 . A mixture of deuterium-enriched compound of claim 13 , wherein the abundance of deuterium in R 1 -R 5 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%.
16 . A mixture of deuterium-enriched compound of claim 13 , wherein the abundance of deuterium in R 6 -R 13 is selected from at least 13%, at least 25%, at least 38%, at least 50%, at least 63%, at least 75%, at least 88%, and 100%.
17 . A mixture of deuterium-enriched compound of claim 13 , wherein the compound is selected from compounds 1-3 of Table 1:
18 . A mixture of deuterium-enriched compound of claim 13 , wherein the compound is selected from compounds 4-6 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 bacterial infections, middle ear infections, tonsillitis, throat infections, laryngitis, bronchitis, pneumonia, sinusitis, non-gonococcal urethritis, and cervicitis, 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.