Granted Patent B2

US 12,667,583 · App. 17/905,142 · Granted Jun 30, 2026

Inventors: Junbiao Chang (Pingdingshan, CN); Jinfa Du (Pingdingshan, CN); Jiandong Jiang (Pingdingshan, CN); Yuhuan Li (Pingdingshan, CN)

Assignee: HENAN GENUINE BIOTECH CO., LTD.

A61K31/7068A61K31/706A61K31/7072A61K31/7076A61P31/14

Abstract

Claims (24)

1 . A method for treating a coronavirus infectious disease, comprising administering to a patient in need thereof a therapeutically or prophylactically effective amount of a compound represented by formula (I) or pharmaceutically acceptable salts thereof,

wherein in the formula (I),

R 1 is H, R 5 —CO—, or

wherein Ar is phenyl, substituted phenyl, naphthyl, or substituted naphthyl, wherein the substituents are selected from the group consisting of C 1-6 alkyl, F, Cl, Br, I, CN, N 3 , OH, NH 2 , OR 5 , and NHR 5 ;

R 2 is H, azido, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkynyl, C 2 -C 6 alkenyl, or halo C 1 -C 6 alkyl;

R 3 is H, unsubstituted or substituted R—CO—, unsubstituted or substituted R—O(C═O)—, or unsubstituted or substituted RNH—CO—, wherein R is C 1 -C 6 alkyl, wherein the substituents are selected from the group consisting of F Cl CN, N 3 , and OR 5 ;

R 4 is H, OH, halogen, C 1 -C 6 alkyl, or C 1 -C 6 alkoxy;

B is selected from the group consisting of:

wherein X 1 is —OH, —NH 2 , R 5 CONH—, R 5 COO—, or R 5 O(C═O) NH—;

X 2 is OH, SH, NH 2 , R 5 COO—, R 5 COS—, R 5 CONH 2 —, or R 5 O(C═O) NH—;

X 3 is H, F, OH, or NH 2 ;

Y is CH or N;

Z is H, OH, or F; and

R 5 is selected from the group consisting of H, C 1 -C 6 alkyl, C 2 -C 6 alkynyl, C 2 -C 6 alkenyl, halo C 1 -C 6 alkyl, phenyl, phenyl substituted with C 1-6 alkyl, C 1-6 alkoxy, CN, N 3 , OH, NH 2 , F, Cl, Br, I, and naphthyl substituted with C 1-6 alkyl, C 1-6 alkoxy, CN, N 3 , OH, NH 2 , or halogen;

wherein the coronavirus infectious disease is a disease caused by infection with a virus of COVID-19.

2 . The method for treating a coronavirus infectious disease according to claim 1 , wherein R 2 is H, azido, methyl, ethyl, methoxy, ethoxy, ethynyl, ethenyl, 2-chloroethyl, 2-fluoroethyl, or trifluoroethyl.

3 . The method for treating a coronavirus infectious disease according to claim 1 , wherein R is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, or isopentyl.

4 . The method for treating a coronavirus infectious disease according to claim 1 , wherein R 4 is H, OH, F, methyl ethyl, methoxy, or ethoxy.

5 . The method for treating a coronavirus infectious disease according to claim 1 , wherein R 5 is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, ethynyl, ethenyl, 2-chloroethyl, 2-fluoroethyl, trifluoroethyl, phenyl, phenyl substituted with C 1-6 alkyl, C 1-6 alkoxy, CN, N 3 , OH, NH 2 , F, Cl, Br, or I, naphthyl, or naphthyl substituted with C 1-6 alkyl, C 1-6 alkoxy, CN, N 3 , OH, NH 2 , F, Cl, Br, or I.

6 . The method for treating a coronavirus infectious disease according to claim 1 , wherein the compound represented by formula (I) is the following compound:

7 . The method for treating a coronavirus infectious disease according to claim 1 , wherein the pharmaceutically acceptable salts of the compound represented by formula (I) are salts formed by the compound of formula (I) and the following acids: hydrochloric acid, hydrobromic acid, sulfamic acid, sulfuric acid, phosphoric acid, nitric acid, formic acid, acetic acid, propionic acid, oxalic acid, glycolic acid, malonic acid, benzoic acid, lactic acid, gluconic acid, citric acid, tartaric acid, succinic acid, fumaric acid, maleic acid, mandelic acid, malic acid, methanesulfonic acid, ethanesulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, naphthalenesulfonic acid, naphthalene disulfonic acid, camphorsulfonic acid, scorbic palmitatic acid, salicylic acid, sulfosalicylic acid, 2-hydroxy-3-naphthoic acid, phthalic acid, lysine, arginine, glutamic acid, glycine, serine, threonine, alanine, isoleucine, or leucine.

8 . The method for treating a coronavirus infectious disease according to claim 1 , wherein the coronavirus infectious disease is a disease caused by infected humans or other animals.

9 . The method for treating a coronavirus infectious disease according to claim 1 , wherein the compound represented by formula (I) or the pharmaceutically acceptable salts thereof is provided in a dosage form selected from the group consisting of an immediate-release dosage form, a sustained-release dosage form, or a controlled-release dosage form.

10 . The method for treating a coronavirus infectious disease according to claim 9 , wherein the dosage form is a tablet, a hard or soft capsule, an aqueous or oily suspension, a granule, an emulsion, a syrup, an elixir, an injection, or a powder injection.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (48)