The present application describes deuterium-enriched sildenafil, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.
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What is claimed is: 1. A deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof: wherein R1-R30 are independently selected from H and D; and the abundance of deuterium in R1-R30 is at least 3%. 2. A deuterium-enriched compound of claim 1, wherein the abundance o
What is claimed is: 1. A deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof: wherein R1-R30 are independently selected from H and D; and the abundance of deuterium in R1-R30 is at least 3%. 2. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R1-R30 is selected from at least 3%, at least 7%, , at least 13%, etc. at least 20%, at least 27%, at least 33%, at least 40%, at least 47%, at least 53%, at least 60%, at least 67%, at least 73%, at least 80%, at least 87%, at least 93%, and 100%. 3. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R1 is 100%. 4. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R5-R6 is selected from at least 50% and at least 100%. 5. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R2-R3 and R7-R30 is selected from at least 4%, at least 8%, at least 15%, at least 23%, at least 31%, at least 38%, at least 46%, at least 50%, at least 58%, at least 65%, at least 73%, at least 81%, at least 88%, at least 96%, and 100%. 6. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R1 and R5-R6 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 R1, R2-R3, and R7-R30 is selected from at least 4%, at least 7%, at least 15%, at least 22%, at least 30%, at least 37%, at least 44%, at least 52%, at least 59%, at least 67%, at least 74%, at least 81%, at least 89%, at least 96%, and 100%. 8. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R2-R3, R5-R6, and R7-R30 is selected from at least 4%, at least 7%, at least 14%, at least 21%, at least 29%, at least 36%, at least 43%, at least 50%, at least 57%, at least 64%, at least 71%, at least 79%, at least 86%, at least 92%, and 100%. 9. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R2-R4 is selected from at least 50%, and 100%. 10. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R5-R11 is selected from at least 14%, at least 29%, at least 43%, at least 57%, at least 71%, at least 86%, and 100%. 11. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R12-R14 is selected from at least 33%, at least 67%, and 100%. 12. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R26-R30 is selected from at least 20%, at least 40%, at least 60%, at least 80%, and 100%. 13. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R15-R22 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%. 14. A deuterium-enriched compound of claim 1, wherein the abundance of deuterium in R23-R25 is selected from at least 33%, at least 67%, and 100%. 15. A deuterium-enriched compound of claim 1, wherein the compound is selected from compounds 1-13 of Table 1. 16. A deuterium-enriched compound of claim 1, wherein the compound is selected from compounds 14-26 of Table 2. 17. An isolated deuterium-enriched compound of formula I or a pharmaceutically acceptable salt thereof: wherein R1-R30 are independently selected from H and D; and the abundance of deuterium in R1-R30 is at least 3%. 18. An isolated deuterium-enriched compound of claim 17, wherein the compound is selected from compounds 1-3 of Table 1. 19. An isolated deuterium-enriched compound of claim 17, wherein the compound is selected from compounds 14-26 of Table 2. 20. A mixture of deuterium-enriched compounds of formula I or a pharmaceutically acceptable salt thereof: wherein R1-R30 are independently selected from H and D; and the abundance of deuterium in R1-R30 is at least 3%. 21. A mixture of deuterium-enriched compounds of claim 20, wherein the compounds are selected from compounds 1-13 of Table 1. 22. A mixture of deuterium-enriched compounds of claim 20, wherein the compounds are selected from compounds 14-26 of Table 2. 23. 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. 24. A method for treating a disease selected from male erectile dysfunction and pulmonary arterial hypertension 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.
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