Deuterated vercirnon
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. The compound of Formula I is useful for the treatment of a disease selected from the group consisting of inflammatory bowel disease (IBD), such as Crohn's disease or ulcerative colitis, and celiac disease.
1. A compound of Formula I:
or a pharmaceutically acceptable salt thereof, wherein:
each R is the same and is CH 3 , CDH 2 , CHD 2 , or 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;
Y 5 is hydrogen or deuterium;
Y 6 is hydrogen or deuterium; and
Y 7 is hydrogen or deuterium;
provided that if each R is CH 3 , and each Y 1 is hydrogen, and each Y 2 is hydrogen, and each Y 3 is hydrogen, and each Y 4 is hydrogen, and Y 5 is hydrogen, and Y 6 is hydrogen, then Y 7 is deuterium.
2. The compound of claim 1 , wherein the compound is an alkali metal salt of the compound of Formula I.
3. The compound of claim 2 , wherein the compound is
4. The compound of claim 1 , wherein each R is CD 3 .
5. The compound of claim 1 , wherein each Y 1 is hydrogen.
6. The compound of claim 1 , wherein each Y 1 is deuterium.
7. The compound of claim 1 , wherein each Y 2 is hydrogen.
8. The compound of claim 1 , wherein each Y 2 is deuterium.
9. The compound of claim 1 , wherein each Y 3 is hydrogen.
10. The compound of claim 1 , wherein each Y 3 is deuterium.
11. The compound of claim 1 , wherein each Y 4 is hydrogen.
12. The compound of claim 1 , wherein each Y 4 is deuterium.
13. 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 5 , Y 6 and Y 7 are each hydrogen:
each
each
each
each
Cmpd #
each R
Y 1
Y 2
Y 3
Y 4
100
CD 3
D
D
H
H
101
CD 3
D
D
D
H
102
CD 3
D
D
D
D
103
CD 3
D
D
H
D
104
CD 3
H
H
H
H
105
CD 3
H
H
D
H
106
CH 3
D
D
H
H
107
CH 3
D
D
D
H
108
CH 3
D
D
D
D
109
CH 3
D
D
H
D
111
CH 3
H
H
D
H
112
CD 3
H
H
D
D
113
CD 3
H
H
H
D
114
CH 3
H
H
D
D
115
CH 3
H
H
H
D
or a pharmaceutically acceptable salt thereof, wherein any atom not designated as deuterium is present at its natural isotopic abundance.
14. The compound of claim 1 , wherein any atom not designated as deuterium is present at its natural isotopic abundance.
15. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable carrier.
16. A method of treating a disease selected from the group consisting of IBD and celiac disease in a subject, comprising administering to the subject in need thereof a pharmaceutical composition of claim 15 .
17. The method of claim 16 , wherein the disease is MD.
18. The method of claim 17 , wherein the disease is Crohn's disease.
19. The method of claim 17 , wherein the disease is ulcerative colitis.