US2020291059A1PendingUtilityA1
Compositions and methods for treating cns disorders
Est. expiryDec 8, 2037(~11.4 yrs left)· nominal 20-yr term from priority
C07J 43/003C07J 7/0085C07J 7/002C07J 1/0059C07J 13/007C07J 7/007A61P 25/00A61K 31/58A61P 25/24C07B 2200/05
72
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Claims
Abstract
Provided herein is a deuterated compound of Formula (I) Formula (I) or a pharmaceutically acceptable salt thereof, wherein R 3a , R 5 , R 6a , R 6b , R 17 , R 21a , R 21 b, R m , R n , R 16a , R 16 b , R 7a , R 7b , R 12a , R 12b , R 11a , R 11b , R 2a , R2 b , R 19 , R 4a , and R 4b are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I) and methods of using the compounds, e.g., in the treatment of CNS-related disorders.
Claims
exact text as granted — not AI-modified1 . A compound of Formula (I)
or a pharmaceutically acceptable salt thereof, wherein
R 3a is C 1 -C 6 alkyl optionally substituted with 1 or more independent occurrences of deuterium or X 2 —OX 3 , wherein each of X 2 and X 3 is independently a C 1 -C 6 alkylene optionally substituted with 1 more occurrences of deuterium; and
each of R 5 , R 6a , R 6b , R 17 , R 21a , R 21b , R m , R n , R 16a , R 16b , R 7a , R 7b , R 12a , R 12b , R 11a , R 11b , R 2a , R 2b , R 19 , R 4a , and R 4b is independently selected from the group consisting of hydrogen and deuterium,
provided that
(a) if R 3a is C 1 -C 6 alkyl with no occurrences of deuterium or X 2 —OX 3 , wherein each of X 2 and X 3 is independently an C 1 -C 6 alkylene with no occurrences of deuterium, then at least one of R 5 , R 6a , R 6b , R 17 , R 21a , R 21b , R m , and R n , R 16a , R 16b , R 7a , R 7b , R 12a , R 12b , R 11a , R 11b , R 2a , R 2b , R 19 , R 4a , and R 4b is deuterium, or
(b) if all of R 5 , R 6a , R 6b , R 17 , R 21a , R 21b , R m , R n , R 16a , R 16b , R 7a , R 7b , R 12a , R 12b , R 11a , R 11b , R 2a , R 2b , R 19 , R 4a , and R 4b are hydrogen, then R 3a is C 1 -C 6 alkyl substituted with 1 or more independent occurrences of deuterium or X 2 —OX 3 , wherein X 2 and X 3 must be substituted with at least one occurrence of deuterium.
2 . The compound of claim 1 , wherein R 3a is C 1 -C 3 alkyl substituted with 0-7 independent occurrences of deuterium or X 2a —OX 3a , wherein X 2a is C 1 -C 3 alkylene substituted with 0-7 independent occurrences of deuterium and X 3a is C 1 -C 3 alkylene substituted with 0-7 independent occurrences of deuterium.
3 . The compound of claim 1 or 2 , wherein if R 3a is —CH 3 , then at least one of R 5 , R 6a , R 6b , R 17 , R 21a , R 21b , R m , and R n is deuterium, or if all of R 5 , R 6a , R 6b , R 17 , R 21a , R 21b , R m , and R n are hydrogen, then R 3a is a methyl group substituted with 1-3 independent occurrences of deuterium.
4 . The compound of claim 1 , wherein R 3a is selected from the group consisting of —CH 3 and CD 3 .
5 . The compound of claim 1 or 2 , wherein R 3a is —CH 3 .
6 . The compound of claim 1 or 2 , wherein R 3a is —CD 3 .
7 . The compound any one of claims 1 - 6 , wherein at least one of R 5 , R 6a , R 6b , R 17 , R 21a , R 21b , R m , R n , R 16a , R 16b , R 7a , R 7b , R 12a , R 12b , R 11a , R 11b , R 2a , R 2b , R 19 , R 4a , and R 4b is deuterium.
8 . The compound of claim any one of claims 1 - 7 , wherein at least one of R 5 , R 6a , R 6b , R 17 , R 21a , R 21b , R m , and R n is deuterium.
9 . The compound of any one of claims 1 - 6 , wherein R 3a is —CH 3 and at least one of R 5 , R 6a , R 6b , R 17 , R 21a , R 21b , R m , R n , R 16a , R 16b , R 7a , R 7b , R 12a , R 12b , R 11a , R 11b , R 2a , R 2b , R 19 , R 4a , and R 4b is deuterium.
10 . The compound of any one of claims 1 - 9 , wherein R 3a is —CH 3 and at least one of R 5 , R 6a , R 6b , R 17 , R 21a , R 21b , R m , and R n is deuterium.
11 . The compound of any one of claims 1 - 10 , wherein R 5 and R 6a are hydrogen.
12 . The compound of any one of claims 1 - 10 , wherein R 5 and R 6a are deuterium.
13 . The compound of any one of claims 1 - 12 , wherein R 17 is hydrogen.
14 . The compound of any one of claims 1 - 12 , wherein R 17 is deuterium.
15 . The compound of any one of claims 1 - 14 , wherein each of R 21a and R 21b is independently selected from the group consisting of hydrogen and deuterium.
16 . The compound of any one of claims 1 - 15 , wherein R 21a and R 21b are hydrogen.
17 . The compound of any one of claims 1 - 15 , wherein R 21a and R 21b are deuterium.
18 . The compound of any one of claims 1 - 17 , wherein R m and R n are hydrogen.
19 . The compound of any one of claims 1 - 17 , wherein R m and R n are deuterium.
20 . The compound of any one of claims 1 - 13 , wherein R 21a , R 21b , R m , and R n are deuterium.
21 . The compound of any one of claims 1 - 10 , wherein R 17 and R 16a are deuterium and R 16b is hydrogen.
22 . The compound of any one of claims 1 - 21 , wherein R 19 is hydrogen.
23 . The compound of any one of claims 1 - 23 , wherein the compound of Formula (I) is the compound of Formula (I-A)
24 . The compound of any one of claims 1 - 10 , wherein the compound of Formula (I) is the compound of Formula (I-B)
25 . The compound of claim 1 , wherein the compound of Formula (I) is the compound of Formula (I-C)
26 . The compound of claim 23 , wherein the compound of Formula (I-C) is selected from the group consisting of the compounds identified in the table below:
Compound
Number
R 3a
R 5
R 6a
R 6b
R 17
R 21a
R 21b
R m
R n
1
—CD 3
H
H
H
H
H
H
H
H
2
—CH 3
D
D
H
H
H
H
H
H
3
—CH 3
H
H
H
D
H
H
H
H
4
—CH 3
H
H
H
H
D
D
H
H
5
—CH 3
H
H
H
H
H
H
D
D
6
—CD 3
H
H
H
H
D
D
D
D
7
—CH 3
H
H
H
H
D
D
D
D
8
—CD 3
H
H
H
H
H
H
D
D
wherein any atom not labeled as deuterium is present at its natural isotopic abundance.
27 . A pharmaceutically acceptable salt of a compound of any one of the preceding claims.
28 . A pharmaceutical composition comprising a compound of any one of claims 1 - 24 or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.
29 . A method of treating a CNS-related disorder in a subject in need thereof, comprising administering to the subject an effective amount of a compound of any one of claims 1 - 24 or a pharmaceutically acceptable salt thereof.
30 . The method of claim 29 , wherein the CNS-related disorder is a sleep disorder, a mood disorder, a schizophrenia spectrum disorder, a convulsive disorder, a disorder of memory and/or cognition, a movement disorder, a personality disorder, autism spectrum disorder, pain, traumatic brain injury, a vascular disease, a substance abuse disorder and/or withdrawal syndrome, tinnitus, or status epilepticus.
31 . The method of claim 29 , wherein the CNS-related disorder is depression.
32 . The method of claim 29 , wherein the CNS-related disorder is postpartum depression.
33 . The method of claim 29 , wherein the CNS-related disorder is major depressive disorder.
34 . The method of claim 31 , wherein the major depressive disorder is moderate major depressive disorder.
35 . The method of claim 31 , wherein the major depressive disorder is severe major depressive disorder.Join the waitlist — get patent alerts
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