257920-61-9

Upstream product

• 52128-85-5 1,2-dihydro-5-methyl-1,2-diphenyl-3H-pyrazol-3-one 
• 122-66-7 diphenyl hydrazine 
• 802934-48-1 4-nitroso-5-methyl-1,2-diphenyl-1,2-dihydro-3H-pyrazol-3-one 

Downstream Products

• 101735-76-6 chloro-acetic acid-(5-methyl-3-oxo-1,2-diphenyl-2,3-dihydro-1H-pyrazol-4-ylamide) 

Relevant academic research and scientific papers

Synthesis and evaluation of N-(5-methyl-3-oxo-1,2-diphenyl-2,3-dihydro-1H- pyrazol-4-yl)-N′-phenylureas as cholecystokinin antagonists

In the search for new cholecystokinin (CCK) ligands, ureidopyrazolines were identified in combinatorial libraries using 168 chemically diverse amines. The structure-activity relationship optimisation of this pyrazoline template 4a resulted in novel 3-oxo-1,2-diphenyl-2,3-dihydro-1H-pyrazol-4-yl)-N′- phenylureas 5a-5o. These novel CCK ligands have shown to act as mixed CCK-A/CCK-B ligands in a [125]I-CCK-8 receptor binding assay. The best pyrazoline 5e of this series displayed an IC50 of 20 and 25 nmol/L for the CCK-A, and CCK-B receptor, respectively. In a subsequent in vivo evaluation using various behavior pharmacological assays, an anxiolytic effect of these novel diphenylpyrazolinyl ureas was found in the elevated x-maze with an ED50 of 1.7 mg/kg. In the despair swimming test, a model for testing antidepressants, an ED50 of 0.69 mg/kg was determinated for urea 5e and the antidepressant effect had a magnitude comparable to desimipramine.

NOVEL UREIDO - AND AMIDO-PYRAZOLONE DERIVATIVES

The present invention provides compounds of formula (I); wherein each of R1 to R4 is independently selected from hydrogen, a halogen, a substituted or unsubstituted cyclic and heterocyclic moiety, substituted or unsubstituted, linear or branched alkyl, alkyloxy, alkylcarbonyl, alkyloxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl, alkynyloxycarbonyl, aryl, benzyl, arlyoxy, arylcarbonyl, aryloxycarbonyl and sulphur equivalents of said oxy, carbonyl and oxycarbonyl moieties, and A is NH, or (CH2)n, where n is preferably 0, 1 or 2. The invention also relates to methods for preparing the compounds and their uses as CCK receptor ligands and CCK antagonists.