Deuterated idebenone
The present invention in one embodiment provides a compound of Formula I: or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula I are as defined in the specification.
1. A compound of Formula I:
or a pharmaceutically acceptable salt thereof, wherein:
each of R 1 , R 2 and R 3 is —CH 3 ;
each Y 1 is hydrogen;
each Y 2 is hydrogen;
each Y 3 is hydrogen;
each Y 4 is hydrogen;
each Y 5 is hydrogen;
each Y 6 is hydrogen;
each Y 7 is hydrogen;
each Y 8 is deuterium;
each Y 9 is deuterium; and
each Y 10 is deuterium.
2. The compound of claim 1 , wherein any atom not designated as deuterium is present at its natural isotopic abundance.
3. A pharmaceutical composition comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable carrier.
4. A method of reducing oxidative toxicity in mitochondria, comprising contacting mitochondria with a compound of claim 1 .
5. A method of treating a condition that is Duchenne's muscular dystrophy or multiple sclerosis, comprising administering to a subject in need of such treatment a compound of claim 1 .
6. The method of claim 5 , wherein the condition is primary progressive multiple sclerosis.
7. A method of treating a condition that is Duchene's muscular dystrophy or multiple sclerosis, comprising administering to a subject in need of such treatment a composition of claim 3 .
8. The compound of claim 1 , wherein the deuterium incorporation at each designated deuterium atom is at least 90%.
9. The compound of claim 1 , wherein the deuterium incorporation at each designated deuterium atom is at least 95%.
10. The compound of claim 1 , wherein the deuterium incorporation at each designated deuterium atom is at least 97%.