1240912-01-9

Upstream product

• 1479-24-9 ethyl 2-fluorobenzoylacetate 
• 1240912-19-9 ethyl 2-diazo-3-(2-fluorophenyl)-3-oxopropanoate 
• 219568-43-1 ethyl 4-oxo-1,4-dihydrocinnoline-3-carboxylate 

Downstream Products

• 1240912-02-0 ethyl 1-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-4-thioxo-1,4-dihydrocinnoline-3-carboxylate 

Relevant academic research and scientific papers

2,5-Disubstituted Pyrazolo[4,3-c]cinnolin-3-ones

Complementary strategies to 2,5-disubstituted pyrazolo[4,3-c]cinnolin-3-ones are reported herein, providing late stage substituent introduction at either the 2- or the 5-position. Treating a readily prepared 4-thiocinnoline ester with substituted hydrazines afforded late stage access to the 2-position, while late stage substituent introduction at the 5-position was achieved via two different strategies: alkylation of 4-hydrazonopyrazol-3-ones, followed by a ring-closing intramolecular SNAr tactic and direct reaction of 5-(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-ones with aryl diazonium salts, followed by cyclization. The strategies described herein provide practical and general methods to prepare 2,5-disubstituted pyrazolo[4,3-c]cinnolin-3-ones.

PYRAZOLO [4,3-c] CINNOLIN-3-ONE M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS

The present invention is directed to pyrazolo [4,3-c] cinnolin-3-one compounds of formula (I) which are M1 receptor positive allosteric modulators and that are useful in the treatment of diseases in which the M1 receptor is involved, such as Alzheimer's disease, schizophrenia, pain or sleep disorders. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases mediated by the M1 receptor.