IP Library › Granted Patent US 9,676,790
Granted Patent B2
US 9,676,790 · App. 14/915,527 · Granted Jun 13, 2017

Substituted thienotriazolodiazapines

Inventor: Scott L. Harbeson (Cambridge, MA)
Assignee: Concert Pharmaceuticals, Inc.
C07D495/14
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Quick Facts
Patent No.
US 9,676,790
App. No.
14/915,527
Granted
Jun 13, 2017
Kind
B2
Abstract

The present invention in one embodiment provides a compound of Formula I: (I), or a pharmaceutically acceptable salt thereof, wherein Y 1 , Y 2 and Y 3 are each independently selected from hydrogen and deuterium; R 1 , R 2 , and R 3 are each methyl and are independently substituted with 0 to 3 deuterium; and R 4 is t-butyl and is substituted with 0 to 9 deuterium; provided that if R 1 , R 2 and R 3 are each —CH 3 , and R 4 is —C(CH 3 ) 3 , then at least one of Y 1 and Y 2 is deuterium.

Claims (218)

1. A compound of Formula I:

or a pharmaceutically acceptable salt thereof, wherein

Y 1 , Y 2 and Y 3 are each independently selected from hydrogen and deuterium;

R 1 , R 2 , and R 3 are each methyl and are independently substituted with 0 to 3 deuterium; and

R 4 is t-butyl and is substituted with 0 to 9 deuterium;

provided that if R 1 , R 2 and R 3 are each CH 3 , and R 4 is —C(CH 3 ) 3 , then at least one of Y 1 and Y 2 is deuterium.

2. The compound of claim 1 , wherein Y 1 and Y 2 are the same and are each hydrogen.

3. The compound of claim 1 , wherein Y 1 and Y 2 are the same and are each deuterium.

4. The compound of claim 1 , wherein Y 3 is hydrogen.

5. The compound of claim 1 , wherein Y 3 is deuterium.

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

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

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

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

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

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

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

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

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

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

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

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

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

19. The compound of claim 2 , wherein R 4 is —C(CH 3 ) 3 .

20. The compound of claim 2 , wherein R 4 is —C(CD 3 ) 3 .

21. The compound of claim 1 , wherein the compound is selected from any one of the compounds (Cmpd) set forth in the table below wherein Y 1 ═Y 2 =hydrogen:

Compound

Y 3

R 1

R 2

R 3

R 4

101

H

—CH 3

—CH 3

—CH 3

—C(CD 3 ) 3

102

H

—CD 3

—CH 3

—CH 3

—C(CD 3 ) 3

103

H

—CH 3

—CD 3

—CH 3

—C(CD 3 ) 3

104

H

—CH 3

—CH 3

—CD 3

—C(CD 3 ) 3

105

D

—CH 3

—CH 3

—CH 3

—C(CD 3 ) 3

106

D

—CD 3

—CH 3

—CH 3

—C(CD 3 ) 3

107

D

—CH 3

—CD 3

—CH 3

—C(CD 3 ) 3

108

D

—CH 3

—CH 3

—CD 3

—C(CD 3 ) 3

109

H

—CD 3

—CD 3

—CH 3

—C(CD 3 ) 3

110

H

—CH 3

—CD 3

—CD 3

—C(CD 3 ) 3

111

H

—CD 3

—CH 3

—CD 3

—C(CD 3 ) 3

112

D

—CD 3

—CD 3

—CH 3

—C(CD 3 ) 3

113

D

—CH 3

—CD 3

—CD 3

—C(CD 3 ) 3

114

D

—CD 3

—CH 3

—CD 3

—C(CD 3 ) 3

115

H

—CD 3

—CD 3

—CD 3

—C(CD 3 ) 3

116

D

—CD 3

—CD 3

—CD 3

—C(CD 3 ) 3

117

H

—CD 3

—CH 3

—CH 3

—C(CH 3 ) 3

118

H

—CH 3

—CD 3

—CH 3

—C(CH 3 ) 3

119

H

—CH 3

—CH 3

—CD 3

—C(CH 3 ) 3

120

D

—CD 3

—CH 3

—CH 3

—C(CH 3 ) 3

121

D

—CH 3

—CD 3

—CH 3

—C(CH 3 ) 3

122

D

—CH 3

—CH 3

—CD 3

—C(CH 3 ) 3

123

H

—CD 3

—CD 3

—CH 3

—C(CH 3 ) 3

124

H

—CH 3

—CD 3

—CD 3

—C(CH 3 ) 3

125

H

—CD 3

—CH 3

—CD 3

—C(CH 3 ) 3

126

D

—CD 3

—CD 3

—CH 3

—C(CH 3 ) 3

127

D

—CH 3

—CD 3

—CD 3

—C(CH 3 ) 3

128

D

—CD 3

—CH 3

—CD 3

—C(CH 3 ) 3

129

H

—CD 3

—CD 3

—CD 3

—C(CH 3 ) 3

130

D

—CD 3

—CD 3

—CD 3

—C(CH 3 ) 3

or a pharmaceutically acceptable salt thereof, wherein any atom not designated as deuterium is present at its natural isotopic abundance.

22. The compound of claim 1 , wherein any atom not designated as deuterium is present at its natural isotopic abundance.

23. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

24. A method of reducing fertility in a subject comprising the step of administering to the subject an effective amount of a composition of claim 23 .

25. The compound of claim 1 or 21 , wherein the deuterium incorporation at each designated deuterium atom is at least 90%.

26. The compound of claim 25 , wherein the deuterium incorporation at each designated deuterium atom is at least 95%.

Assignments (2)
MERGER Recorded Sep 14, 2023
From: CONCERT PHARMACEUTICALS, INC.
To: SUN PHARMACEUTICAL INDUSTRIES, INC.
Reel/Frame 064907/0514 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 5, 2016
From: HARBESON, SCOTT L.
To: CONCERT PHARMACEUTICALS, INC.
Reel/Frame 039941/0827 →
Continuity (2)
Provisional Application 61872200 · Aug 30, 2013
Related Publication 20160214995A1 · Jul 28, 2016