IP Library › Granted Patent US 12,686,665
Granted Patent B2
US 12,686,665 · App. 18/696,807 · Granted Jul 21, 2026

Bicyclic fused ring derivative or salt thereof and pharmaceutical composition comprising same

Inventors: Eun-Kyung Kim (Seongnam-si, KR); Cheol-Hee Lim (Suwon-si, KR); Kang-Yo Lee (Seoul, KR); Hyun-Ho Choi (Yongin-si, KR)
Assignee: YUHAN CORPORATION
C07D235/14A61K31/4184A61K31/4192A61K31/4439A61K31/454A61K31/496A61K31/506A61K31/52A61K31/5377A61K31/675C07D249/18C07D403/10C07D403/12C07D487/04C07F9/65068C07F9/65188
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Quick Facts
Patent No.
US 12,686,665
App. No.
18/696,807
Filed
Mar 28, 2024
Granted
Jul 21, 2026
Kind
B2
Art Unit
1625
USPC
514/80
Abstract

Provided are a bicyclic fused ring, such as for example, benzo[d]imidazole, benzo[d][1,2,3]triazole, or 8-oxo-8,9-dihydro-7H-purine derivative, or pharmaceutically acceptable salt thereof, a process for the preparation thereof, a pharmaceutical composition comprising the same and a use thereof, wherein the bicyclic fused ring derivative or pharmaceutically acceptable salt thereof has an inhibitory activity against the lysyl oxidase family and can be usefully applied for preventing or treating various diseases associated with the lysyl oxidase family, such as idiopathic pulmonary fibrosis (IPF), non-alcoholic steatohepatitis (NASH), chronic kidney disease (CKD), or liver cirrhosis.

Claims (356)

1 . A compound of Formula 1 or pharmaceutically acceptable salt thereof:

wherein,

A is —CR 1 ═, —N═, or —C(O)—,

R is absent where A is —CR 1 ═ or —N═, and R is C 1-6 alkyl where A is —C(O)—,

Q is N or CR 2 ,

W is N or CR 3 ,

Y is N or CR 4 ,

X is a heterocyclic ring or a benzene ring,

the heterocyclic ring or the benzene ring is optionally substituted with 1 or 2 substituents selected from the group consisting of C 1-6 alkyl, hydroxy-C 1-6 alkyl, halogen, trifluoromethyl, C 1-6 alkoxy, C 1-6 alkylcarbonyl, C 1-6 alkoxybenzylaminosulfonyl, C 1-6 alkylsulfonyl, di-C 1-6 alkylphosphoryl, di-C 1-6 alkoxyphosphoryl, mono- or di-C 1-6 alkylaminosulfonyl, cyclopropylaminosulfonyl, pyrrolidinylsulfonyl, morpholinylsulfonyl, piperidinylsulfonyl, 3,3-difluoropyrrolidinylsulfonyl, C 1-3 alkyl-piperazinylsulfonyl, and trifluoromethylsulfonyl,

R 1 is hydrogen, trifluoromethyl, or C 1-6 alkyl,

R 2 , R 3 , and R 4 are, independently each other, selected from the group consisting of hydrogen, halogen, trifluoromethyl, cyano, nitro, hydroxycarbonyl, C 1-6 alkoxycarbonyl and —C(O)NR 5 R 6 , and

R 5 and R 6 are, independently each other, hydrogen, C 1-6 alkyl, or C 1-6 alkoxy; or form a 3- to 7-membered N-containing cyclic ring together with the nitrogen atom to which they are bonded.

2 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein

A is —CR 1 ═ or —N═,

R is absent, compound or pharmaceutically

Q and Y are —CH═, and

W is CR 3 .

3 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein

A is —C(O)—,

R is C 1-6 alkyl,

Q and Y are —N═, and

W is —CH═.

4 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein X is a benzene ring, a pyridine ring, a pyrimidine ring, or a pyrazole ring.

5 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 4 , wherein

A is —CR 1 ═ or —N═,

R is absent,

Q and Y are —CH═, and

W is CR 3 ,

X is a benzene ring, a pyridine ring, a pyrimidine ring, or a pyrazole ring,

the benzene ring, the pyridine ring, the pyrimidine ring, or the pyrazole ring is optionally substituted with 1 or 2 substituents selected from the group consisting of C 1-6 alkyl, hydroxy-C 1-6 alkyl, halogen, trifluoromethyl, C 1-6 alkoxy, C 1-6 alkylcarbonyl, C 1-6 alkoxybenzylaminosulfonyl, C 1-6 alkylsulfonyl, di-C 1-6 alkylphosphoryl, di-C 1-6 alkoxyphosphoryl, mono- or di-C 1-6 alkylaminosulfonyl, cyclopropylaminosulfonyl, pyrrolidinylsulfonyl, morpholinylsulfonyl, piperidinylsulfonyl, 3,3-difluoropyrrolidinylsulfonyl, C 1-3 alkyl-piperazinylsulfonyl, and trifluoromethylsulfonyl,

R 1 is hydrogen, trifluoromethyl or C 1-6 alkyl,

R 3 is selected from the group consisting of hydrogen, halogen, trifluoromethyl, cyano, hydroxycarbonyl, C 1-6 alkoxycarbonyl and —C(O)NR 5 R 6 ,

R 5 and R 6 are, independently each other, hydrogen, C 1-6 alkyl, or C 1-6 alkoxy; or form a 3- to 7-membered N-containing cyclic ring together with the nitrogen atom to which they are bonded.

6 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , which is selected from the group consisting of:

(Z)-3-fluoro-4-(6-fluoro-4-(3-fluorophenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(6-fluoro-4-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(6-fluoro-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-fluoro-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-fluoro-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-fluoro-4-(6-fluoro-4-(4-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(6-fluoro-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(6-fluoro-4-(4-(morpholinosulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-fluoro-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-fluoro-1H-benzo[d]imidazol-4-yl)-N-methylbenzenesulfonamide;

(Z)-3-fluoro-4-(4-(3-fluorophenyl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(6-(trifluoromethyl)-4-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(3-(methylsulfonyl)phenyl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-fluoro-4-(4-(4-(methylsulfonyl)phenyl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(4-(morpholinosulfonyl)phenyl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N-methylbenzenesulfonamide;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)-4-methoxyphenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-((3,3-difluoropyrrolidin-1-yl)sulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-methoxy-5-(N-methylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N,N-diethylsulfamoyl)-2-methoxyphenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N-cyclopropylsulfamoyl)-2-methoxyphenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-isopropylsulfamoyl)-4-methoxyphenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-cyclopropylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-methylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-(4-methoxybenzyl)sulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(piperidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(ethylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-methyl-5-((trifluoromethyl)sulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-(tert-butyl)sulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-diethylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(dimethylphosphoryl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(4-(dimethylphosphoryl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(diethoxyphosphoryl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-((3,3-difluoropyrrolidin-1-yl)sulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylic acid;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylic acid;

(Z)-3-fluoro-4-(4-(3-fluorophenyl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(2-(trifluoromethyl)-4-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-fluoro-4-(4-(3-(methylsulfonyl)phenyl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-fluoro-4-(4-(4-(methylsulfonyl)phenyl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N-(tert-butyl)benzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N-methylbenzenesulfonamide;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-fluoro-4-(2-methyl-4-(4-(morpholinosulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-fluoro-4-(2-methyl-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(2-methyl-4-(4-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-fluoro-4-(2-methyl-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-1H-benzo[d]imidazol-4-yl)-N-(tert-butyl)benzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-1H-benzo[d]imidazol-4-yl)-N-methylbenzenesulfonamide;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(4-(N,N-dimethylsulfamoyl)phenyl)-2-methyl-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-4-(4-(morpholinosulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-2-methyl-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-4-(4-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(4-(N-cyclopropylsulfamoyl)phenyl)-2-methyl-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(4-(N-(tert-butyl)sulfamoyl)phenyl)-2-methyl-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-cyclopropylsulfamoyl)phenyl)-2-methyl-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-4-(3-(N-methylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(4-(N,N-dimethylsulfamoyl)phenyl)-N,N,2-trimethyl-1H-benzo[d]imidazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N,N,2-trimethyl-4-(4-(morpholinosulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-N,N,2-trimethyl-1H-benzo[d]imidazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N,N,2-trimethyl-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N,N,2-trimethyl-4-(4-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(4-(N-cyclopropylsulfamoyl)phenyl)-N,N,2-trimethyl-1H-benzo[d]imidazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-cyclopropylsulfamoyl)phenyl)-N,N,2-trimethyl-1H-benzo[d]imidazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N,N,2-trimethyl-4-(3-(N-methylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxamide;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-ethyl-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-4-(2-ethyl-4-(4-(morpholinosulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-ethyl-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-4-(2-ethyl-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-4-(2-ethyl-4-(4-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-ethyl-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-4-(2-ethyl-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-ethyl-1H-benzo[d]imidazol-4-yl)-N-(tert-butyl)benzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-ethyl-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-ethyl-1H-benzo[d]imidazol-4-yl)-N-methylbenzenesulfonamide;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-isopropyl-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-fluoro-4-(2-isopropyl-4-(4-(morpholinosulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-isopropyl-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-fluoro-4-(2-isopropyl-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(2-isopropyl-4-(4-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-isopropyl-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-fluoro-4-(2-isopropyl-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-isopropyl-1H-benzo[d]imidazol-4-yl)-N-(tert-butyl)benzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-isopropyl-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-isopropyl-1H-benzo[d]imidazol-4-yl)-N-methylbenzenesulfonamide;

(Z)-5-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-2-methoxy-N,N-dimethylbenzenesulfonamide;

(Z)-4-(4-(3-((3,3-difluoropyrrolidin-1-yl)sulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-3-fluoro-4-(4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-4-methoxy-N-methylbenzenesulfonamide;

(Z)-3-fluoro-4-(4-(3-(methylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N,N-diethyl-4-methoxybenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-cyclopropyl-4-methoxybenzenesulfonamide;

(Z)-5-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-isopropyl-2-methoxybenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-methylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-fluoro-4-(4-(2-methoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)-4-methoxyphenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-((3,3-difluoropyrrolidin-1-yl)sulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-methoxy-5-(N-methylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N,N-diethylsulfamoyl)-2-methoxyphenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N-cyclopropylsulfamoyl)-2-methoxyphenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-isopropylsulfamoyl)-4-methoxyphenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-cyclopropylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-methylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-(4-methoxybenzyl)sulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(piperidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(ethylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-methyl-5-((trifluoromethyl)sulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-(tert-butyl)sulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-diethylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(diethoxyphosphoryl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)-4-methoxyphenyl)-N-methoxy-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N-methoxy-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N-methoxy-4-(2-methoxy-5-(N-methylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N,N-diethylsulfamoyl)-2-methoxyphenyl)-N-methoxy-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N-cyclopropylsulfamoyl)-2-methoxyphenyl)-N-methoxy-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N-methoxy-N-methyl-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N,N-diethylsulfamoyl)-2-methoxyphenyl)-N-methoxy-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-N-methoxy-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-9-(4-amino-2-fluorobut-2-en-1-yl)-7-methyl-6-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-7,9-dihydro-8H-purin-8-one;

(Z)-3-(9-(4-amino-2-fluorobut-2-en-1-yl)-7-methyl-8-oxo-8,9-dihydro-7H-purin-6-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(9-(4-amino-2-fluorobut-2-en-1-yl)-7-methyl-8-oxo-8,9-dihydro-7H-purin-6-yl)-N-methylbenzenesulfonamide;

(Z)-9-(4-amino-2-fluorobut-2-en-1-yl)-7-methyl-6-(3-(methylsulfonyl)phenyl)-7,9-dihydro-8H-purin-8-one;

(Z)-3-(9-(4-amino-2-fluorobut-2-en-1-yl)-7-methyl-8-oxo-8,9-dihydro-7H-purin-6-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)-4-methoxyphenyl)-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-((3,3-difluoropyrrolidin-1-yl)sulfonyl)phenyl)-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N-methyl-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-methoxy-5-(N-methylsulfamoyl)phenyl)-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N-methyl-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N,N-diethylsulfamoyl)-2-methoxyphenyl)-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-cyclopropylsulfamoyl)-4-methoxyphenyl)-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-isopropylsulfamoyl)-4-methoxyphenyl)-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-cyclopropylsulfamoyl)phenyl)-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N-methyl-4-(3-(N-methylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(ethylsulfonyl)phenyl)-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-5-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(pyrrolidin-1-carbonyl)-1H-benzo[d][1,2,3]triazol-4-yl)-2-methoxy-N,N-dimethylbenzenesulfonamide;

(Z)-(1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-((3,3-difluoropyrrolidin-1-yl)sulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-yl)(pyrrolidin-1-yl)methanone;

(Z)-(1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-yl)(pyrrolidin-1-yl)methanone;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(pyrrolidin-1-carbonyl)-1H-benzo[d][1,2,3]triazol-4-yl)-4-methoxy-N-methylbenzenesulfonamide;

(Z)-(1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-yl)(pyrrolidin-1-yl)methanone;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(pyrrolidin-1-carbonyl)-1H-benzo[d][1,2,3]triazol-4-yl)-N,N-diethyl-4-methoxybenzenesulfonamide;

(Z)-5-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(pyrrolidin-1-carbonyl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-cyclopropyl-2-methoxybenzenesulfonamide;

(Z)-5-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(pyrrolidin-1-carbonyl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-isopropyl-2-methoxybenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(pyrrolidin-1-carbonyl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(pyrrolidin-1-carbonyl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-methylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(pyrrolidin-1-carbonyl)-1H-benzo[d][1,2,3]triazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-(1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(ethylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-yl)(pyrrolidin-1-yl)methanone;

(Z)-1-(3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-4-fluorophenyl)ethan-1-one;

(Z)-(3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-4-fluorophenyl)methanol;

(Z)-(3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-2-chlorophenyl)methanol;

(Z)-3-fluoro-4-(4-(pyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(5-fluoropyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(4-(5-chloropyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)-3-fluoro-but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(pyrimidin-5-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(1-methyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl-amine;

(Z)-4-(4-(1-ethyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl]-3-fluoro-but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(1-isopropyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-2-(4-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-1H-pyrazol-1-yl)ethan-1-ol;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-cyano-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-cyano-1H-benzo[d]imidazol-4-yl)-4-methoxy-N-methylbenzenesulfonamide;

(Z)-4-(5-acetyl-2-fluorophenyl)-1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-fluoro-5-(hydroxymethyl)phenyl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluoro-2-but-1-yl)-4-(2-chloro-3-(hydroxymethyl)phenyl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(pyridin-3-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-fluoropyridin-3-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-chloropyridin-3-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(pyrimidin-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-methyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-ethyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1,3-dimethyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-(2-hydroxyethyl)-1H-pyrazol-3-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-1-(3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl)-4-fluorophenyl)ethan-1-one;

(Z)-(3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl)-4-fluorophenyl)methanol;

(Z)-(3-(1-(4-amino-2-fluoro-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl)-2-chlorophenyl)methanol;

(Z)-3-fluoro-4-(4-(5-fluoropyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

(Z)-4-(4-(5-chloropyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-3-fluoro-4-(4-(pyrimidin-5-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

(Z)-4-(4-(1-ethyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-4-[4-(1,3-dimethyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl]-3-fluorobut-2-en-1-amine;

(Z)-2-(4-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl]-1H-pyrazol-1-yl)ethan-1-ol;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-[2-fluoro-5-(hydroxymethyl)phenyl]-1H-benzo[d][1,2,3]triazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-[2-chloro-3-(hydroxymethyl)phenyl-1H-benzo[d][1,2,3]triazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-fluoropyridin-3-yl)-1H-benzo[d][1,2,3]triazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-chloropyridin-3-yl)-1H-benzo[d][1,2,3]triazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(pyrimidin-5-yl)-1H-benzo[d][1,2,3]triazol-6-carbonitrile; and

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-methyl-1H-pyrazol-5-yl)-1H-benzo[d][1,2,3]triazol-6-carbonitrile.

7 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , which is selected from the group consisting of:

(Z)-3-fluoro-4-(6-fluoro-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(6-fluoro-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-fluoro-1H-benzo[d]imidazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-fluoro-1H-benzo[d]imidazol-4-yl)-N-methylbenzenesulfonamide;

(Z)-3-fluoro-4-(4-(3-(methylsulfonyl)phenyl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N-methylbenzenesulfonamide;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)-4-methoxyphenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-((3,3-difluoropyrrolidin-1-yl)sulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-methoxy-5-(N-methylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N,N-diethylsulfamoyl)-2-methoxyphenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N-cyclopropylsulfamoyl)-2-methoxyphenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-isopropylsulfamoyl)-4-methoxyphenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-cyclopropylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-methylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-(4-methoxybenzyl)sulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(piperidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(ethylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-methyl-5-((trifluoromethyl)sulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-diethylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(dimethylphosphoryl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-N-methylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-fluoro-4-(2-methyl-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-2-methyl-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-2-methyl-4-(3-(N-methylsulfamoyl)phenyl)-1H-benzo[d]imidazol-6-carboxylate;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-N,N,2-trimethyl-1H-benzo[d]imidazol-6-carboxamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-2-ethyl-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-5-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-2-methoxy-N,N-dimethylbenzenesulfonamide;

(Z)-4-(4-(3-((3,3-difluoropyrrolidin-1-yl)sulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-3-fluoro-4-(4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-4-methoxy-N-methylbenzenesulfonamide;

(Z)-3-fluoro-4-(4-(3-(methylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-cyclopropyl-4-methoxybenzenesulfonamide;

(Z)-5-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-isopropyl-2-methoxybenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-cyclopropylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N-methylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d][1,2,3]triazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-fluoro-4-(4-(2-methoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)-4-methoxyphenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-((3,3-difluoropyrrolidin-1-yl)sulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-methoxy-5-(N-methylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(methylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N,N-diethylsulfamoyl)-2-methoxyphenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N-cyclopropylsulfamoyl)-2-methoxyphenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-isopropylsulfamoyl)-4-methoxyphenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-cyclopropylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-methylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N-(4-methoxybenzyl)sulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(ethylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

methyl (Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-methyl-5-((trifluoromethyl)sulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxylate;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)-4-methoxyphenyl)-N-methoxy-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N-methoxy-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N-methoxy-4-(2-methoxy-5-(N-methylsulfamoyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N,N-diethylsulfamoyl)-2-methoxyphenyl)-N-methoxy-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N-cyclopropylsulfamoyl)-2-methoxyphenyl)-N-methoxy-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-N-methoxy-N-methyl-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-(N,N-diethylsulfamoyl)-2-methoxyphenyl)-N-methoxy-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(N,N-dimethylsulfamoyl)phenyl)-N-methoxy-N-methyl-1H-benzo[d][1,2,3]triazol-6-carboxamide;

(Z)-1-(3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-4-fluorophenyl)ethan-1-one;

(Z)-3-fluoro-4-(4-(pyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(5-fluoropyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-4-(4-(5-chloropyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)-3-fluoro-but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(pyrimidin-5-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(1-methyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-yl-amine;

(Z)-4-(4-(1-ethyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl]-3-fluoro-but-2-en-1-amine;

(Z)-3-fluoro-4-(4-(1-isopropyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-3-fluoro-4-(4-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]-6-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)but-2-en-1-amine;

(Z)-2-(4-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)-1H-pyrazol-1-yl)ethan-1-ol;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(3-(pyrrolidin-1-ylsulfonyl)phenyl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-cyano-1H-benzo[d]imidazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-cyano-1H-benzo[d]imidazol-4-yl)-4-methoxy-N-methylbenzenesulfonamide;

(Z)-4-(5-acetyl-2-fluorophenyl)-1-(4-amino-2-fluorobut-2-en-1-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(2-fluoro-5-(hydroxymethyl)phenyl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluoro-2-but-1-yl)-4-(2-chloro-3-(hydroxymethyl)phenyl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(pyridin-3-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-fluoropyridin-3-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-chloropyridin-3-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(pyrimidin-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-methyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-ethyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1,3-dimethyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-(2-hydroxyethyl)-1H-pyrazol-3-yl)-1H-benzo[d]imidazol-6-carbonitrile;

(Z)-3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl)-N,N-dimethylbenzenesulfonamide;

(Z)-1-(3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl)-4-fluorophenyl)ethan-1-one;

(Z)-(3-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl)-4-fluorophenyl)methanol;

(Z)-(3-(1-(4-amino-2-fluoro-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl)-2-chlorophenyl)methanol;

(Z)-3-fluoro-4-(4-(5-fluoropyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

(Z)-4-(4-(5-chloropyridin-3-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-3-fluoro-4-(4-(pyrimidin-5-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl)but-2-en-1-amine;

(Z)-4-(4-(1-ethyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl)-3-fluorobut-2-en-1-amine;

(Z)-4-[4-(1,3-dimethyl-1H-pyrazol-5-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-yl]-3-fluorobut-2-en-1-amine;

(Z)-2-(4-(1-(4-amino-2-fluorobut-2-en-1-yl)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-4-yl]-1H-pyrazol-1-yl)ethan-1-ol;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-[2-fluoro-5-(hydroxymethyl)phenyl]-1H-benzo[d][1,2,3]triazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-[2-chloro-3-(hydroxymethyl)phenyl-1H-benzo[d][1,2,3]triazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-fluoropyridin-3-yl)-1H-benzo[d][1,2,3]triazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(5-chloropyridin-3-yl)-1H-benzo[d][1,2,3]triazol-6-carbonitrile;

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(pyrimidin-5-yl)-1H-benzo[d][1,2,3]triazol-6-carbonitrile; and

(Z)-1-(4-amino-2-fluorobut-2-en-1-yl)-4-(1-methyl-1H-pyrazol-5-yl)-1H-benzo[d][1,2,3]triazol-6-carbonitrile.

8 . A process for preparing a compound of Formula 1 or pharmaceutically acceptable salt thereof, the process of which comprises reacting a compound of Formula 2 with a compound of Formula 3 to obtain a compound of Formula 1a; deprotecting the compound of Formula 1a to obtain a compound of Formula 1; and optionally converting the compound of Formula 1 to a pharmaceutically acceptable salt thereof:

wherein, A, R, Q, W, Y, and X are the same as defined in claim 1 ; Pr is an amine protecting group; and B is boronic acid (B(OH) 2 ) or boronic acid pinacol ester.

9 . A pharmaceutical composition for inhibiting lysyl oxidase family comprising the compound or pharmaceutically acceptable salt thereof as claimed in claim 1 as an active ingredient.

10 . A method for inhibiting lysyl oxidase family in a mammal, which comprises administering a therapeutically effective amount of the compound or pharmaceutically acceptable salt thereof as claimed in claim 1 to the mammal in need thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2024
From: KIM, EUN-KYUNG; LIM, CHEOL-HEE; LEE, KANG-YO; CHOI, HYUN-HO
To: YUHAN CORPORATION
Reel/Frame 066938/0779 →
Priority Claims (1)
KR 10-2021-0130916 · Oct 1, 2021 · national
Continuity (1)
Related Publication 20250066308A1 · Feb 27, 2025
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