5219-15-8

Upstream product

• 141-97-9 ethyl acetoacetate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 141-78-6 ethyl acetate 
• 587-88-2 ethyl 2-(4-fluorophenyl)acetate 
• 108-24-7 acetic anhydride 

Downstream Products

• 1068515-21-8 4-(4-fluorophenyl)-3-methyl-1-(pyridin-2-yl)-1H-pyrazol-5-ol 

Relevant academic research and scientific papers

IMIDAZO [1,5-A]PYRIMIDINYL CARBOXAMIDE COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted imidazo[1,5-a]pyrimidinyl carboxamide and related organic compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted imidazo[1,5-a]pyrimidinyl carboxamide compounds described herein include substituted 2-heterocyclyl-4-alkyl-imidazo[1,5-a]pyrirnidine-8-carboxamide compounds and variants thereof.

Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)?H Functionalization/Annulation Reactions

Rhodium-catalyzed C(sp2)?H functionalization reactions of 4-aryl-5-pyrazolones followed by [3+2] annulation reactions with alkynes provide rapid access to highly enantioenriched five-membered-ring 4-spiro-5-pyrazolones. The use of a chiral SCpRh catalyst enabled the synthesis of a large range of spiropyrazolones with all-carbon quaternary stereogenic centers in up to 99 % yield and 98 % ee from readily available substrates.

Synthesis and biological evaluation of substituted pyrazoles as blockers of divalent metal transporter 1 (DMT1)

Three distinct series of substituted pyrazole blockers of divalent metal transporter 1 (DMT1) were elaborated from the high-throughput screening pyrazolone hit 1. Preliminary hit-to-lead efforts revealed a preference for electron-withdrawing substituents in the 4-amido-5-hydroxypyrazole series 6a-l. In turn, this preference was more pronounced in a series of 4-aryl-5- hydroxypyrazoles 8a-j. The representative analogs 6f and 12f were found to be efficacious in a rodent model of acute iron hyperabsorption. These three series represent promising starting points for lead optimization efforts aimed at the discovery of DMT1 blockers as iron overload therapeutics.

PYRAZOLE AND PYRROLE COMPOUNDS USEFUL IN TREATING IRON DISORDERS

This invention is directed to pyrazole and pyrrole compounds, for example, compounds of formula (I): wherein R1, R2, R3 and R4 are as defined herein, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of iron disorders. This invention is also directed to pharmaceutical compositions comprising the compounds and methods of using the compounds to treat iron disorders.