IP Library Granted Patent US 12686676
Granted Patent B2
US 12686676 · App. 18/566,804 · Granted Jul 21, 2026

Compound, endothelin-A receptor antagonist, and pharmaceutical composition

Inventors: Keigo Tanaka (Tsukuba, JP); Tomohisa Ninomiya (Tsukuba, JP); Yoshihide Tomata (Tsukuba, JP)
Assignee: ALCHEMEDICINE, INC.
C07D413/14A61K31/4439A61K31/497A61P9/12C07D405/14
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Quick Facts
Patent No.
US 12686676
App. No.
18/566,804
Granted
Jul 21, 2026
Kind
B2
Abstract

An object of the present invention is to provide a compound having an ETA receptor antagonistic effect, etc. The object can be attained by a compound represented by the following formula (1): wherein variables are as described herein, or a pharmaceutically acceptable salt thereof.

Claims (33)

1 . A compound represented by the following formula (1):

wherein

R 1 and R 2 are each independently hydrogen or alkyl,

R 3 and R 4 are each independently hydrogen or alkyl, or

R 3 and R 4 together form oxo,

R 5 to R 7 are each independently hydrogen, alkyl, haloalkyl, halogen, alkoxy or haloalkoxy, each R 8 is independently alkyl, haloalkyl or halogen,

n is an integer of 0 to 3, and

Ar is represented by the following formula (Ar1) or (Ar2):

wherein

X and Y are nitrogen and oxygen, respectively, or oxygen and nitrogen, respectively,

R 9 and R 10 are each independently hydrogen, alkyl, haloalkyl or halogen,

each R 11 is independently alkyl, haloalkyl, halogen, alkoxy or haloalkoxy, and

m is an integer of 0 to 3,

or a pharmaceutically acceptable salt thereof.

2 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein each of R 1 and R 2 is hydrogen.

3 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein each of R 5 and R 7 is hydrogen, and R 6 is alkyl.

4 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein n is 0.

5 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein Ar is represented by formula (Ar1).

6 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein each of R 9 and R 10 is alkyl.

7 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein X and Y are nitrogen and oxygen, respectively.

8 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein X and Y are oxygen and nitrogen, respectively.

9 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein Ar is represented by formula (Ar2).

10 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein each R 11 is independently alkyl or alkoxy.

11 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein m is 2.

12 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is selected from the group consisting of the following compounds:

13 . A method for inhibiting an endothelin A receptor, comprising administering an effective amount of the compound or the pharmaceutically acceptable salt thereof according to claim 1 to a patient in need thereof.

14 . The method according to claim 13 , wherein the method selectively inhibits the endothelin A receptor in contrast to an endothelin B receptor.

15 . A pharmaceutical composition comprising the compound or the pharmaceutically acceptable salt thereof according to claim 1 .

16 . A method for preventing or treating pulmonary hypertension, nephropathy, hypertension, hepatitis, cancer, pain, heart failure, or vasospasm, comprising administering an effective amount of the compound or the pharmaceutically acceptable salt thereof according to claim 1 to a patient in need thereof.

17 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is

18 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is

19 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is

20 . The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is