Deuterated idebenone

Patent metadata

Field	Value
Publication number	US-10017445-B2
Application number	US-201314414039-A
Country	US
Kind code	B2
Filing date	Jul 12, 2013
Priority date	Jul 12, 2012
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

The present invention in one embodiment provides a compound of Formula I:(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 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.

2. The compound of claim 1 , wherein R 1 is CH 3 .

3. The compound of claim 1 , wherein R 1 is CD 3 .

4. The compound of claim 1 , wherein R 2 is CH 3 .

5. The compound of claim 1 , wherein R 2 is CD 3 .

6. The compound of claim 1 , wherein R 3 is CH 3 .

7. The compound of claim 1 , wherein R 3 is CD 3 .

8. The compound of claim 1 , 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.

9. The compound 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 :

TABLE

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, wherein any atom not designated as deuterium is present at its natural isotopic abundance.

10. The compound 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, wherein any atom not designated as deuterium is present at its natural isotopic abundance.

11. The compound 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

Assignees

• Concert Pharmaceuticals Inc

Inventors

• Tung Roger D

Classifications

• C07B59/001

  Acyclic or carbocyclic compounds · CPC title

• C07C50/28 Primary

  with monocyclic quinoid structure · CPC title

• C07B2200/05

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