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