Deuterated idebenone

Patent metadata

Field	Value
Publication number	US-10843993-B2
Application number	US-201916414462-A
Country	US
Kind code	B2
Filing date	May 16, 2019
Priority date	Jul 12, 2012
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

The present invention in one embodiment provides a method of treating Leber's hereditary optic neuropathy, comprising administering to a subject in need of such treatment a compound of Formula I:

or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula I are as defined in the specification.

First claim

What is claimed is:

1. A method of treating Leber's hereditary optic neuropathy, comprising administering to a subject in need of such treatment a compound of Formula I, or a pharmaceutical composition comprising a compound of Formula I:

or a pharmaceutically acceptable salt thereof, wherein:
each of R 1 , R 2 and R 3 is independently selected from CH 3 and CD 3 ;
each Y 1 is the same and is hydrogen or deuterium;
each Y 2 is the same and is hydrogen or deuterium;
each Y 3 is the same and is hydrogen or deuterium;
each Y 4 is the same and is hydrogen or deuterium;
each Y 5 is the same and is hydrogen or deuterium;
each Y 6 is the same and is hydrogen or deuterium;
each Y 7 is the same and is hydrogen or deuterium;
each Y 8 is the same and is deuterium;
each Y 9 is the same and is deuterium; and
each Y 10 is the same and is deuterium,
wherein any atom not designated as deuterium is present at its natural isotopic abundance.

2. The method of claim 1 , wherein in the compound of Formula I, R 1 is CH 3 .

3. The method of claim 1 , wherein in the compound of Formula I, R 1 is CD 3 .

4. The method of claim 1 , wherein in the compound of Formula I, R 2 is CH 3 .

5. The method of claim 1 , wherein in the compound of Formula I, R 2 is CD 3 .

6. The method of claim 1 , wherein in the compound of Formula I, R 3 is CH 3 .

7. The method of claim 1 , wherein in the compound of Formula I, R 3 is CD 3 .

8. The method of claim 1 , wherein in the compound of Formula I, each Y 1 is deuterium; each Y 2 is deuterium; each Y 3 is deuterium; each Y 4 is deuterium; each Y 5 is deuterium; each Y 6 is deuterium; and each Y 7 is deuterium.

9. The method of claim 1 , wherein the compound is selected from the group consisting of the compounds (Cmpd) set forth in the table below, wherein 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; and R 3 is CH 3 :

Cmpd No.
R 1
R 2
each Y 10
each Y 9
each Y 8

107
CH 3
CH 3
D
D
D

115
CH 3
CD 3
D
D
D

123
CD 3
CH 3
D
D
D

131
CD 3
CD 3
D
D
D

or a pharmaceutically acceptable salt thereof.

10. The method of claim 1 , wherein the compound is selected from the group consisting of the compounds (Cmpd) set forth in the table below, wherein 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; and R 3 is CD 3 :

Cmpd No.
R 1
R 2
each Y 10
each Y 9
each Y 8

207
CH 3
CH 3
D
D
D

215
CH 3
CD 3
D
D
D

223
CD 3
CH 3
D
D
D

231
CD 3
CD 3
D
D
D

or a pharmaceutically acceptable salt thereof.

11. The method of claim 1 , wherein the compound is selected from the group consisting of the compounds (Cmpd) set forth in the table below, wherein each Y 1 is deuterium; each Y 2 is deuterium; each Y 3 is deuterium; each Y 4 is deuterium; each Y 5 is deuterium; each Y 6 is deuterium; each Y 7 is deuterium; each Y 8 is deuterium; each Y 9 is deuterium; and each Y 10 is deuterium:

Cmpd No.
R 1
R 2
R 3

300
CH 3
CH 3
CH 3

301
CH 3
CH 3
CD 3

302
CH 3
CD 3
CH 3

303
CH 3
CD 3
CD 3

304
CD 3
CH 3
CH 3

305
CD 3
CH 3
CD 3

306
CD 3
CD 3
CH 3

307
CD 3
CD 3
CD 3

or a pharmaceutically acceptable salt thereof.

Assignees

• Concert Pharmaceuticals Inc

Inventors

• Tung Roger D

Classifications

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title

• C07B59/001

  Acyclic or carbocyclic compounds · CPC title

• C07C50/28 Primary

  with monocyclic quinoid structure · CPC title