US2023391734A1PendingUtilityA1
Substituted phenyl sulfonyl phenyl triazole thiones and uses thereof
Est. expiryOct 30, 2037(~11.3 yrs left)· nominal 20-yr term from priority
C07D 249/12A61P 25/28A61K 9/10A61P 3/00C07D 243/10A61K 31/18A61P 25/00A61K 31/4196A61K 31/5377A61K 31/454A61K 31/496A61K 47/36A61K 47/38A61K 47/32C07D 401/10C07D 403/10
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Claims
Abstract
The present disclosure relates to substituted phenyl sulfonyl phenyl triazole thiones, pharmaceutical compositions containing them, and methods of using them.
Claims
exact text as granted — not AI-modified1 - 23 . (canceled)
24 . A pharmaceutical composition comprising a at least one compound of Formula (I):
wherein
R 1 , R 2 , and R 3 are each independently hydrogen, hydroxy, halogen, optionally substituted C 1-4 alkyl, optionally substituted C 1-4 alkoxy, —CN, —C(O)R x , —C(O)OR x , —S(O) 2 R x , or —NR y R z ;
R x , R y , and R z are each independently H or optionally substituted C 1-4 alkyl, or R y and R z taken together with the nitrogen to which they are attached form an optionally substituted monocyclic heterocycloalkyl ring;
or a pharmaceutically acceptable salt thereof, and
(b) HPMC-AS.
25 . (canceled)
26 . The pharmaceutical composition of claim 24 , wherein the pharmaceutical composition is in the form of a spray dry dispersion (SDD).
27 - 30 . (canceled)
31 . The pharmaceutical composition of claim 24 , wherein R 1 is hydrogen.
32 . The pharmaceutical composition of claim 24 , wherein R 1 is —OCH 2 CH 2 —O—CH 2 CH 3 or —OCH 2 CH 2 OCH 3 .
33 . The pharmaceutical composition of claim 24 , wherein R 1 is —NHCH 2 CH 2 OH or —N(CH 2 CH 3 ) 2 .
34 . The pharmaceutical composition of claim 24 , wherein R 1 is morpholinyl, 4-methyl-piperazin-1-yl, piperidinyl, or pyrrolidinyl.
35 . The pharmaceutical composition of claim 24 , wherein R 2 is hydrogen, C 1-4 alkyl, or substituted C 1-4 alkyl.
36 . The pharmaceutical composition of claim 24 , wherein R 2 is CF 3 .
37 . The pharmaceutical composition of claim 24 , wherein R 2 is methyl.
38 . The pharmaceutical composition of claim 24 , wherein R 2 is optionally substituted C 1-4 alkoxy, —CN, or —NR y R z .
39 . The pharmaceutical composition of claim 24 , wherein R 2 is —N(CH 3 ) 2 .
40 . The pharmaceutical composition of claim 24 , wherein R 2 is morpholinyl.
41 . The pharmaceutical composition of claim 24 , wherein R 2 is methoxy, —OCH 2 CH 2 —O—CH 2 CH 3 , or —OCH 2 CH 2 OCH 3 .
42 . The pharmaceutical composition of claim 24 , wherein R 3 is halogen.
43 . The pharmaceutical composition of claim 24 , wherein R 3 is chloro.
44 . The pharmaceutical composition of claim 24 , wherein R 3 is hydrogen.
45 . The pharmaceutical composition of claim 24 , wherein R 3 is methyl.
46 . The pharmaceutical composition of claim 24 , wherein R 3 is —CN.
47 . The pharmaceutical composition of claim 24 , wherein R 3 is morpholinyl.
48 . The pharmaceutical composition of claim 24 , wherein R 3 is C 1-4 alkoxy.
49 . The pharmaceutical composition of claim 24 , wherein the compound is selected from the group consisting of
Compound
No.
Structure
Name
1
4-(4-((4-chloro-3- (trifluoromethyl)phenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione;
2
4-(4-((4-chloro-3- (trifluoromethyl)phenyl)sulfonyl)-2- morpholinophenyl)-2,4-dihydro-3H-1,2,4- triazole-3-thione;
3
4-(4-(phenylsulfonyl)phenyl)-2,4-dihydro- 3H-1,2,4-triazole-3-thione;
4
4-(4-((4-chlorophenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione;
5
4-(4-((4-chloro-3- methylphenyl)sulfonyl)phenyl)-2,4- dihydro-3H-1,2,4-triazole-3-thione;
6
4-((4-(5-thioxo-1,5-dihydro-4H-1,2,4- triazol-4-yl)phenyl)sulfonyl)benzonitrile;
7
4-(4-((4- morpholinophenyl)sulfonyl)phenyl)-2,4- dihydro-3H-1,2,4-triazole-3-thione;
8
4-(4-((4-methoxyphenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione;
9
4-(4-tosylphenyl)-2,4-dihydro-3H-1,2,4- triazole-3-thione;
10
4-(4-((4-fluorophenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione;
11
4-(4-((3- (trifluoromethyl)phenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione;
12
4-(4-((3-methoxyphenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione;
13
4-(4-((3-(2- ethoxyethoxy)phenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione;
14
3-((4-(5-thioxo-1,5-dihydro-4H-1,2,4- triazol-4-yl)phenyl)sulfonyl)benzonitrile;
15
4-(4-((3- (dimethylamino)phenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione;
16
4-(4-((3- morpholinophenyl)sulfonyl)phenyl)-2,4- dihydro-3H-1,2,4-triazole-3-thione;
17
4-(4-(m-tolylsulfonyl)phenyl)-2,4- dihydro-3H-1,2,4-triazole-3-thione;
18
4-(4-((4-chloro-3- (trifluoromethyl)phenyl)sulfonyl)-2-((2- hydroxyethyl)amino)phenyl)-2,4-dihydro- 3H-1,2,4-triazole-3-thione;
19
4-(4-((4-chloro-3- (trifluoromethyl)phenyl)sulfonyl)-2- (piperidin-1-yl)phenyl)-2,4-dihydro-3H- 1,2,4-triazole-3-thione;
20
4-(4-((4-chloro-3- (trifluoromethyl)phenyl)sulfonyl)-2-(4- methylpiperazin-1-yl)phenyl)-2,4- dihydro-3H-1,2,4-triazole-3-thione;
21
4-(4-((4-chloro-3- (trifluoromethyl)phenyl)sulfonyl)-2- (diethylamino)phenyl)-2,4-dihydro-3H- 1,2,4-triazole-3-thione;
22
4-(4-((4-chloro-3- (trifluoromethyl)phenyl)sulfonyl)-2-(2- ethoxyethoxy)phenyl)-2,4-dihydro-3H- 1,2,4-triazole-3-thione;
23
4-(4-((4-methyl-3- (trifluoromethyl)phenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione;
24
4-(4-((4-chloro-3- (trifluoromethyl)phenyl)sulfonyl)-2- (pyrrolidin-1-yl)phenyl)-2,4-dihydro-3H- 1,2,4-triazole-3-thione; and
25
4-(4-((3-(2- methoxyethoxy)phenyl)sulfonyl)phenyl)- 2,4-dihydro-3H-1,2,4-triazole-3-thione,
or a pharmaceutically acceptable salt thereof.
50 . The pharmaceutical composition of claim 24 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
51 . The pharmaceutical composition of claim 24 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.Join the waitlist — get patent alerts
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