IP Library Granted Patent US 9,447,006
Granted Patent B2
US 9,447,006 · App. 11/445,582 · Granted Sep 20, 2016

Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers

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Quick Facts
Patent No.
US 9,447,006
App. No.
11/445,582
Granted
Sep 20, 2016
Kind
B2
Abstract

Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed, as well as compounds useful in the methods of the invention, such as alpha-tocopherol quinone. Methods and compounds useful in treating other disorders are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

Claims (64)

1. A method of treating a mitochondrial disorder, comprising administering to a subject suffering from the mitochondrial disorder a composition comprising a therapeutically effective amount of one or more compounds of the formula:

where R 11 , R 12 , and R 13 are independently selected from the group consisting of H, —C 1 -C 4 alkyl, —C 1 -C 4 haloalkyl, —CN, —F, —Cl, —Br, and —I, with the proviso that if any of R 11 , R 12 , or R 13 is H, then at least one of the other two substituents is neither H nor methyl; and all stereoisomers, and mixtures of stereoisomers thereof;

wherein said one or more compounds are the sole active pharmaceutical agent or agents present in a therapeutically effective amount in the composition;

and wherein the mitochondrial disorder is selected from the group consisting of Leber's Hereditary Optic Neuropathy (LHON); Friedreich's Ataxia (FA); Parkinson's disease; amyotrophic lateral sclerosis (ALS); and Huntington's Disease.

2. The method of claim 1 , wherein the one or more compounds are selected from compounds of the formula:

and all stereoisomers, and mixtures of stereoisomers thereof.

3. The method of claim 2 , wherein the one or more compounds is the compound:

4. The method of claim 1 , wherein none of R 11 , R 12 , and R 13 is H and at least one of R 11 , R 12 , and R 13 is not methyl, and all stereoisomers, and mixtures of stereoisomers thereof.

5. The method of claim 1 , wherein the mitochondrial disorder is Friedreich's Ataxia (FA).

6. The method of claim 1 , wherein the mitochondrial disorder is Leber's Hereditary Optic Neuropathy (LHON).

7. The method of claim 1 , wherein the mitochondrial disorder is Parkinson's disease.

8. The method of claim 1 , wherein the mitochondrial disorder is amyotrophic lateral sclerosis (ALS).

9. The method of claim 1 , wherein the mitochondrial disorder is Huntington's Disease.

10. The method of claim 2 , wherein the mitochondrial disorder is Friedreich's Ataxia (FA).

11. The method of claim 2 , wherein the mitochondrial disorder is Leber's Hereditary Optic Neuropathy (LHON).

12. The method of claim 2 , wherein the mitochondrial disorder is Parkinson's disease.

13. The method of claim 2 , wherein the mitochondrial disorder is amyotrophic lateral sclerosis (ALS).

14. The method of claim 2 , wherein the mitochondrial disorder is Huntington's Disease.

15. The method of claim 3 , wherein the mitochondrial disorder is Friedreich's Ataxia (FA).

16. The method of claim 3 , wherein the mitochondrial disorder is Leber's Hereditary Optic Neuropathy (LHON).

17. The method of claim 3 , wherein the mitochondrial disorder is Parkinson's disease.

18. The method of claim 3 , wherein the mitochondrial disorder is amyotrophic lateral sclerosis (ALS).

19. The method of claim 3 , wherein the mitochondrial disorder is Huntington's Disease.

20. The method of claim 2 , wherein the one or more compounds are the sole active pharmaceutical agent or agents in the composition.

21. The method of claim 3 , wherein the compound is the sole active pharmaceutical agent in the composition.

22. The method of claim 12 , wherein the one or more compounds are the sole active pharmaceutical agent or agents in the composition.

23. The method of claim 14 , wherein the one or more compounds are the sole active pharmaceutical agent or agents in the composition.

24. The method of claim 17 , wherein the compound is the sole active pharmaceutical agent in the composition.

25. The method of claim 19 , wherein the compound is the sole active pharmaceutical agent in the composition.

26. The method of claim 2 , wherein the method consists of administering the composition to the subject.

27. The method of claim 3 , wherein the method consists of administering the composition to the subject.

28. The method of claim 12 , wherein the method consists of administering the composition to the subject.

29. The method of claim 14 , wherein the method consists of administering the composition to the subject.

30. The method of claim 17 , wherein the method consists of administering the composition to the subject.

31. The method of claim 19 , wherein the method consists of administering the composition to the subject.

32. A method of treating a mitochondrial disorder, comprising administering to a subject suffering from the mitochondrial disorder a composition comprising a therapeutically effective amount of one or more compounds of the formula:

where R 11 , R 12 , and R 13 are independently selected from the group consisting of H, —C 1 -C 4 alkyl, —C 1 -C 4 haloalkyl, —CN, —F, —Cl, —Br, and —I, with the proviso that if any of R 11 , R 12 , and R 13 is H, then at least one of the other two substituents is neither H nor methyl; and all stereoisomers, and mixtures of stereoisomers thereof;

wherein the one or more compounds are the sole active pharmaceutical agent or agents used to treat the mitochondrial disorder;

and wherein the mitochondrial disorder is selected from the group consisting of Leber's Hereditary Optic Neuropathy (LHON); Friedreich's Ataxia (FA); Parkinson's disease; amyotrophic lateral sclerosis (ALS); and Huntington's Disease.

33. The method of claim 32 , wherein the one or more compounds are selected from compounds of the formula:

and all stereoisomers, and mixtures of stereoisomers thereof.

34. The method of claim 32 , wherein the one or more compounds is the compound:

35. The method of claim 33 , wherein the mitochondrial disorder is Friedreich's Ataxia (FA).

36. The method of claim 33 , wherein the mitochondrial disorder is Leber's Hereditary Optic Neuropathy (LHON).

37. The method of claim 33 , wherein the mitochondrial disorder is Parkinson's disease.

38. The method of claim 33 , wherein the mitochondrial disorder is amyotrophic lateral sclerosis (ALS).

39. The method of claim 33 , wherein the mitochondrial disorder is Huntington's Disease.

40. The method of claim 34 , wherein the mitochondrial disorder is Friedreich's Ataxia (FA).

41. The method of claim 34 , wherein the mitochondrial disorder is Leber's Hereditary Optic Neuropathy (LHON).

42. The method of claim 34 , wherein the mitochondrial disorder is Parkinson's disease.

43. The method of claim 34 , wherein the mitochondrial disorder is amyotrophic lateral sclerosis (ALS).

44. The method of claim 34 , wherein the mitochondrial disorder is Huntington's Disease.

45. A method of treating a mitochondrial disorder, comprising administering to a subject suffering from the mitochondrial disorder a composition comprising a therapeutically effective amount of one or more compounds of the formula:

where R 11 , R 12 , and R 13 are independently selected from the group consisting of H, —C 1 -C 4 alkyl, —C 1 -C 4 haloalkyl, —CN, —F, —Cl, —Br, and —I, with the proviso that if any of R 11 , R 12 , or R 13 is H, then at least one of the other two substituents is neither H nor methyl; and all stereoisomers, and mixtures of stereoisomers thereof;

and wherein the mitochondrial disorder is selected from the group consisting of Leber's Hereditary Optic Neuropathy (LHON); Friedreich's Ataxia (FA); and amyotrophic lateral sclerosis (ALS).

46. The method of claim 45 , wherein the one or more compounds are selected from compounds of the formula:

and all stereoisomers, and mixtures of stereoisomers thereof.

47. The method of claim 45 , wherein the one or more compounds is the compound:

48. The method of claim 46 , wherein the mitochondrial disorder is Friedreich's Ataxia (FA).

49. The method of claim 46 , wherein the mitochondrial disorder is Leber's Hereditary Optic Neuropathy (LHON).

50. The method of claim 46 , wherein the mitochondrial disorder is amyotrophic lateral sclerosis (ALS).

51. The method of claim 47 , wherein the mitochondrial disorder is Friedreich's Ataxia (FA).

52. The method of claim 47 , wherein the mitochondrial disorder is Leber's Hereditary Optic Neuropathy (LHON).

53. The method of claim 47 , wherein the mitochondrial disorder is amyotrophic lateral sclerosis (ALS).

Assignments (7)
TERMINATION AND RELEASE OF PATENT SECURITY AGREEMENT @ REEL 061803 AND FRAME 0878 Recorded Oct 20, 2023
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
To: PTC THERAPEUTICS, INC.
Reel/Frame 065303/0163 →
SECURITY INTEREST Recorded Oct 28, 2022
From: PTC THERAPEUTICS, INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 061803/0878 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 14, 2020
From: BIOELECTRON TECHNOLOGY CORPORATION
To: PTC THERAPEUTICS, INC.
Reel/Frame 053210/0036 →
CHANGE OF NAME Recorded Feb 8, 2017
From: EDISON PHARMACEUTICALS, INC.
To: BIOELECTRON TECHNOLOGY CORPORATION
Reel/Frame 041660/0644 →
RELEASE OF SECURITY INTEREST IN EXCLUSIVELY LICENSED PATENTS RECORDED AT REEL/FRAME 25572/731 Recorded Jul 11, 2011
From: JPMORGAN CHASE BANK N.A., AS ADMINISTRATIVE AGENT
To: PENWEST PHARMACEUTICALS CO.
Reel/Frame 026571/0792 →
CONFIRMATORY GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS (EXCLUSIVELY LICENSED PATENTS) Recorded Dec 30, 2010
From: PENWEST PHARMACEUTICALS CO.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 025572/0731 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2006
From: MILLER, GUY M.; HECHT, SIDNEY M.
To: EDISON PHARMACEUTICALS, INC.
Reel/Frame 018126/0367 →