Triazine derivatives having virus replication inhibitory activity and pharmaceutical composition comprising the same

Patent metadata

Field	Value
Publication number	US-12559474-B2
Application number	US-202217790358-A
Country	US
Kind code	B2
Filing date	Feb 17, 2022
Priority date	Apr 14, 2021
Publication date	Feb 24, 2026
Grant date	Feb 24, 2026

Abstract

A compound represented by Formula (I):

wherein Y is N or the like; R 1 is substituted or unsubstituted aromatic heterocyclyl or the like; R 2 is substituted or unsubstituted aromatic carbocyclyl or the like; R 3 is substituted or unsubstituted aromatic heterocyclyl or the like; —X— is —NH— or the like; m is 1 or the like; R 5a is each independently a hydrogen atom or the like; R 5b is each independently a hydrogen atom or the like; n is 1 or the like; R 4a is each independently a hydrogen atom or the like; and R 4b is each independently a hydrogen atom or the like, or a pharmaceutically acceptable salt thereof.

First claim

The invention claimed is:

1 . A compound represented by Formula (I):

wherein
Y is N, or CR 7 ;
R 7 is a hydrogen atom, or substituted or unsubstituted alkyl;
R 1 is substituted or unsubstituted aromatic heterocyclyl, substituted or unsubstituted non-aromatic heterocyclyl, or substituted or unsubstituted carbamoyl;
R 2 is 6 membered aromatic carbocyclyl substituted with one halogen or one cyano, and further substituted with 1, 2, 3 or 4 substituent(s) selected from substituent group G, or 6 membered aromatic heterocyclyl substituted with one halogen or one cyano, and further substituted with 1 or 2 substituent(s) selected from substituent group G;
substituent group G is selected from the group consisting of halogen, cyano, alkyl, alkenyl, alkynyl, haloalkyl, alkyloxy, alkenyloxy, alkynyloxy and haloalkyloxy;
R 3 is substituted or unsubstituted aromatic carbocyclyl, substituted or unsubstituted non-aromatic carbocyclyl, substituted or unsubstituted aromatic heterocyclyl, substituted or unsubstituted non-aromatic heterocyclyl, or substituted or unsubstituted alkyl;
—X— is —NR 6 —, —CR 6 R 6′ —, —O—, —S—, or a single bond;
R 6 and R 6′ are each independently a hydrogen atom, or substituted or unsubstituted alkyl;
m is 0, 1, or 2;
R 5a is each independently a hydrogen atom, or substituted or unsubstituted alkyl;
R 5b is each independently a hydrogen atom, or substituted or unsubstituted alkyl;
n is 1;
R 4a is each independently a hydrogen atom, or substituted or unsubstituted alkyl; and
R 4b is each independently a hydrogen atom, or substituted or unsubstituted alkyl,
or a pharmaceutically acceptable salt thereof.

2 . The compound according to claim 1 , wherein
Y is N, or a pharmaceutically acceptable salt thereof.

3 . The compound according to claim 1 , wherein
—X— is —NH—, or a pharmaceutically acceptable salt thereof.

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

5 . The compound according to claim 1 , wherein
R 4a is each independently a hydrogen atom or unsubstituted alkyl, and R 4b is each independently a hydrogen atom, or a pharmaceutically acceptable salt thereof.

6 . The compound according to claim 1 , wherein
R 5a is each independently a hydrogen atom, and R 5b is each independently a hydrogen atom, or a pharmaceutically acceptable salt thereof.

7 . The compound according to claim 1 , wherein
R 1 is substituted or unsubstituted aromatic heterocyclyl, or a pharmaceutically acceptable salt thereof.

8 . The compound according to claim 1 , wherein
R 1 is substituted or unsubstituted aromatic heterocyclyl, m is 1, R 5a is a hydrogen atom, and R 5b is a hydrogen atom, or pharmaceutically acceptable salt thereof.

9 . The compound according to claim 1 , wherein
R 1 is substituted or unsubstituted aromatic heterocyclyl, and m is 0, or a pharmaceutically acceptable salt thereof.

10 . The compound according to claim 1 , wherein
R 3 is substituted or unsubstituted 6 membered aromatic carbocyclyl, substituted or unsubstituted 3 to 10 membered non-aromatic carbocyclyl, substituted or unsubstituted 5 to 6 membered aromatic heterocyclyl, substituted or unsubstituted 9 to 10 membered aromatic heterocyclyl, substituted or unsubstituted 13 to 15 membered aromatic heterocyclyl, or substituted or unsubstituted 3 to 20 membered non-aromatic heterocyclyl, or a pharmaceutically acceptable salt thereof.

11 . The compound according to claim 1 , wherein
R 3 is substituted or unsubstituted 6 membered aromatic carbocyclyl, substituted or unsubstituted 9 to 10 membered aromatic heterocyclyl, or substituted or unsubstituted 9 to 13 membered non-aromatic heterocyclyl, or a pharmaceutically acceptable salt thereof.

12 . The compound according to claim 1 , wherein
Formula (I) is Formula (I′):

wherein
R 1′ is a group represented by Formula:

R 2′ is a group represented by Formula:

 and
R 3′ is a group represented by Formula:

or a pharmaceutically acceptable salt thereof.

13 . The compound according to claim 1 , wherein
Formula (I) is Formula (I′):

wherein
R 1′ is a group represented by Formula:

R 2′ is a group represented by Formula:

 and
R 3′ is a group represented by Formula:

or a pharmaceutically acceptable salt thereof.

14 . The compound according to claim 1 , wherein
the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

15 . A pharmaceutical composition comprising the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive, carrier or diluent.

16 . A method for inhibiting SARS-COV-2, comprising administering the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, to a subject.

17 . A method for treating an infection caused by SARS-COV-2, comprising administering the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, to a subject.

Assignees

• Shionogi & Co
• Univ Hokkaido Nat Univ Corp

Inventors

• Tachibana Yuki
• Uehara Shota
• UNOH Yuto
• Nakahara Kenji
• Taoda Yoshiyuki
• Kasamatsu Koji
• Yamatsu Yukiko
• Ando Shigeru
• SUTO Takahiro
• Sasaki Michihito

Classifications

• A61K31/53

  having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine (melarsoprol A61K31/555 {; with four nitrogen atoms A61K31/495}) · CPC title

• A61K47/542

  Carboxylic acids, e.g. a fatty acid or an amino acid · CPC title

• C07D498/04

  Ortho-condensed systems · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title