US 12,735,398 B2Granted

Benzoazepine compound, and composition and use thereof

AssigneesXuzhou Medical University, Shanghaitech University

InventorsDong Guo, Xudong Cao, Wenzhong Yan, Jianjun Cheng, Ying Sun, Limin Su, Ying Ren, Ruoqi Wang, Haoran Zhang, Haoxing Yuan

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Abstract

A novel benzoazepine compound, comprising a pharmaceutically acceptable salt thereof. A pharmaceutical composition comprising the compound and a pharmaceutically acceptable salt thereof. The use of the compound and the composition in the prevention or treatment of diseases related to arginine vasopressin Vla receptor, arginine vasopressin V1b receptor, arginine vasopressin V2 receptor, sympathetic nervous system or renin-angiotensin-aldosterone system. A method for preventing and/or treating arginine vasopressin-related diseases. The compound is represented by formula (I), wherein the substituents are defined herein:

Claims14

Dependent claims

A compound of formula (I) or a stereoisomer thereof or a pharmaceutically acceptable salt thereof,

wherein
X is NH;
Y is selected from N, CH or S;
R1, R2 and R3 are each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-6 alkyl, C1-6 alkoxy, or C3-8 cycloalkyl;
R4 is selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, C1-6 alkyl, C1-6 alkoxy, C3-8 cycloalkyl, aryl, heteroaryl, heterocyclyl, heterocyclyl-(CH2)n-, aryl-C1-6 alkyl-, heteroaryl-C1-6 alkyl-, aryl-(CH2)n-O—, heteroaryl-(CH2)n-O—, C3-8 cycloalkyl-C(O)—, heterocyclyl-C(O)—, aryl-C(O)—, or heteroaryl-C(O), wherein each of C1-6 alkyl,C1-6 alkoxy, C3-8 cycloalkyl, aryl, heteroaryl, heterocyclyl, heterocyclyl-(CH2)n-, aryl-C1-6 alkyl-,heteroaryl-C1-6 alkyl-, aryl-(CH2)n-O—, heteroaryl-(CH2)n-O—, C3-8 cycloalkyl-C(O)—, heterocyclyl-C(O)—, aryl-C(O)—, or heteroaryl-C(O) is unsubstituted or substituted with at least one substituent selected from halogen, C1-6 alkyl, C1-6 cycloalkyl, or heterocyclyl;
R5 is selected from
m is 0, 1, 2, 3 or 4;
n is 0, 1, 2, 3 or 4.

5 more elements

A compound of stereoisomer thereof or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of:

1) N-(4-(7-chloro-5-((3-morpholinopropyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
2) N-(4-(7-chloro-5-((4-morpholinobutyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
3) N-(4-(7-chloro-5-((5-morpholinopentyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
4) N-(4-(7-chloro-5-((2-morpholinoethyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
5) N-(4-(7-chloro-5-((3-(pyridin-4-yl)propyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
6) N-(4-(7-chloro-5-((2-(pyridin-4-yl)ethyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
7) N-(4-(7-chloro-5-((4-(pyridin-4-yl)butyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
8) N-(4-(7-chloro-5-((5-(pyridin-4-yl)pentyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
9) N-(4-(7-chloro-5-((3-(piperidin-1-yl)propyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
10)N-(4-(7-chloro-5-((2-(piperidin-1-yl)ethyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
11)N-(4-(7-chloro-5-((4-(piperidin-1-yl)butyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
12)N-(4-(7-chloro-5-((5-(piperidin-1-yl)pentyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
13)N-(4-(7-chloro-5-((3-morpholino-3-oxopropyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
14)N-(4-(7-chloro-5-((4-morpholino-4-oxobutyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
15)N-(4-(7-chloro-5-((5-morpholino-5-oxopentyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
16)N-(4-(7-chloro-5-((6-morpholino-6-oxohexyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
17)N-(4-(7-chloro-5-((3-(4-methylpiperazin-1-yl)propyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
18)N-(4-(7-chloro-5-((2-(4-methylpiperazin-1-yl)ethyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
19)N-(4-(7-chloro-5-((4-(4-methylpiperazin-1-yl)butyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
20)N-(4-(7-chloro-5-((5-(4-methylpiperazin-1-yl)pentyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
21)N-(4-(7-chloro-5-((2-phenoxyethyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
22)N-(4-(7-chloro-5-((3-phenoxypropyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
23)N-(4-(7-chloro-5-((4-phenoxybutyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
24)N-(4-(7-chloro-5-((5-phenoxypentyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
25)N-(4-(7-chloro-5-((3-(diethylamino)propyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
26)N-(4-(7-chloro-5-((2-(diethylamino)ethyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
27)N-(4-(7-chloro-5-((4-(diethylamino)butyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;
and
28)N-(4-(7-chloro-5-((5-(diethylamino)pentyl)amino)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide.

26 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/271,523Filed 17 Dec 2021
Priority: CN 202110067206.619 Jan 2021
Published: US 2024/0076279 A17 Mar 2024
Granted: 15 Sep 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61P 13/12
Drugs for disorders of the urinary system: of the kidneys
C07D 223/16
Condensed with carbocyclic rings or ring systems: benzazepines; Hydrogenated benzazepines
C07D
Heterocyclic compounds