912773-22-9

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromo-pyrazolo[1,5-a]pyridine-3-carbonitrile is used as a building block for the synthesis of various biologically active compounds. Its potential as a kinase inhibitor makes it an important tool in drug discovery and development, contributing to the creation of novel therapeutic agents.
Used in Organic Chemistry:
In the field of organic chemistry, 6-Bromo-pyrazolo[1,5-a]pyridine-3-carbonitrile serves as a valuable reagent for the development of novel synthetic methods and strategies. Its unique structure and properties facilitate the exploration of new chemical reactions and pathways, expanding the scope of synthetic chemistry.

InChI:InChI=1S/C7H4BrN3O2/c8-4-1-9-6-5(7(12)13)2-10-11(6)3-4/h1-3H,(H,12,13)

Upstream product

• 2065-75-0 2-Bromo-malonaldehyde 
• 41680-34-6 3-aminopyrazole-4-carboxylic acid 
• 41680-34-6 5-amino-1H-pyrazole-4-carboxylic acid 

Downstream Products

• 1204925-71-2 6-bromo-3-[((2S)-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]pyrazolo[1,5-a]pyrimidine 
• 1065080-92-3 N-(2-amino-2-oxoethyl)-6-{[3-(trifluoromethyl)phenyl]thio}pyrazolo[1,5-a]-pyrimidine-3-carboxamide 

Relevant academic research and scientific papers

Discovery of an Orally Bioavailable, Brain-Penetrating, in Vivo Active Phosphodiesterase 2A Inhibitor Lead Series for the Treatment of Cognitive Disorders

Herein, we describe the discovery of a potent, selective, brain-penetrating, in vivo active phosphodiesterase (PDE) 2A inhibitor lead series. To identify high-quality leads suitable for optimization and enable validation of the physiological function of PDE2A in vivo, structural modifications of the high-throughput screening hit 18 were performed. Our lead generation efforts revealed three key potency-enhancing functionalities with minimal increases in molecular weight (MW) and no change in topological polar surface area (TPSA). Combining these structural elements led to the identification of 6-methyl-N-((1R)-1-(4-(trifluoromethoxy)phenyl)propyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (38a), a molecule with the desired balance of preclinical properties. Further characterization by cocrystal structure analysis of 38a bound to PDE2A uncovered a unique binding mode and provided insights into its observed potency and PDE selectivity. Compound 38a significantly elevated 3′,5′-cyclic guanosine monophosphate (cGMP) levels in mouse brain following oral administration, thus validating this compound as a useful pharmacological tool and an attractive lead for future optimization.

PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS

Compounds of Formula (0), Formula (I), and Formula (II) and methods of use as Interleukin-1 Receptor Associated Kinase (IRAK4) inhibitors are described herein.

HETEROCYCLIC COMPOUND

A compound represented by the formula (I): wherein each symbol is as described in the SPECIFICATION, or a salt thereof has a PDE2A inhibitory action, and is useful as a prophylactic or therapeutic drug for schizophrenia, Alzheimer's disease and the like.

Design of pyrazolo-pyrimidines as 11β-HSD1 inhibitors through optimisation of molecular electrostatic potential

The inhibition of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) is a potentially attractive mechanism for the treatment of obesity and other elements of the metabolic syndrome. A series of pyrazolo-pyrimidine inhibitors of this enzyme were identified from directed library synthesis. Knowledge of how these compounds bind to the enzyme and the key hydrogen-bonding interactions was used to design further compounds. The hydrogen-bond acceptor strength was calculated from the molecular electrostatic potential using quantum mechanical theory. Compounds were designed to modulate the acceptor strength, thus optimising the potency and other drug-like properties. Compounds with enhanced CNS penetration were designed through further modification of the electrostatic potential and the hydrogen-bond properties.

PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS

Compounds of the formula I or II: wherein X, m, Ar, R1 and R2 are as defined herein. The subject compounds are useful for treatment of IRAK-mediated conditions.

Novel Derivatives

The present invention relates to novel piperazine derivatives; to processes for their preparation; to pharmaceutical compositions containing the derivatives; and to the use of the derivatives in therapy to treat diseases for which blocking the Cav2.2 calcium channels is beneficial.

PYRAZOLO [1,5-A]PYRIMIDINES AS INHIBITORS OF STEAROYL-COA DESATURASE

The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts thereof, which are useful as inhibitors of human stearoyl-CoA desaturase (SCD). The invention further relates to pharmaceutical compositions comprising these c