2-heteroaryl-3-oxo-2,3-dihydropyridazine-4-carboxamides for the treatment of cancer

Patent metadata

Field	Value
Publication number	US-11795164-B2
Application number	US-202217819602-A
Country	US
Kind code	B2
Filing date	Aug 12, 2022
Priority date	Feb 9, 2017
Publication date	Oct 24, 2023
Grant date	Oct 24, 2023

Abstract

The present invention covers 2-heteroaryl-3-oxo-2,3-dihydropyridazine-4-carboxamide compounds of general formula (1):

in which X, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of cancer or conditions with dysregulated immune responses or other disorders associated with aberrant AHR signaling, as a sole agent or in combination with other active ingredients.

First claim

The invention claimed is:

1. A compound having the structure:

or a hydrate or solvate thereof, or a pharmaceutically acceptable salt of any of the foregoing.

2. The compound of claim 1 , which is

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , which is

or a pharmaceutically acceptable salt thereof.

4. A composition, comprising 6-(4-chlorophenyl)-N-(1-hydroxypropan-2-yl)-2-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

5. The composition of claim 4 , comprising a racemic mixture of: 6-(4-chlorophenyl)-N-[(2S)-1-hydroxypropan-2-yl]-2-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxamide, or a pharmaceutically acceptable salt thereof; and 6-(4-chlorophenyl)-N-[(2R)-1-hydroxypropan-2-yl]-2-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

6. The composition of claim 4 , comprising 6-(4-chlorophenyl)-N-[(2S)-1-hydroxypropan-2-yl]-2-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydropyridazine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

7. A pharmaceutical composition, comprising a compound of claim 2 , or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable excipient.

8. A pharmaceutical composition, comprising a compound of claim 3 , or a pharmaceutically acceptable salt thereof.

Assignees

• Bayer Ag
• Bayer Pharma AG
• Deutsches Krebsforsch

Inventors

• Gutcher Ilona
• Schmees Norbert
• Röse Lars
• Bader Benjamin
• Kober Christina
• Carretero Rafael
• Stöckigt Detlef
• Irlbacher Horst
• Platten Michael

Classifications

• C07D237/14

  Oxygen atoms · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• A61K31/506

  not condensed and containing further heterocyclic rings · CPC title

• A61K31/501

  not condensed and containing further heterocyclic rings · CPC title

• C07D417/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title