162142-14-5

Basic information

• Product Name: 1-CYCLOPENTYL-3-ETHYL-1,4,5,6-TETRAHYDRO-7H-PYRAZOLO[3,4-C]PYRIDIN-7-ONE
• Synonyms: 1-CYCLOPENTYL-3-ETHYL-1,4,5,6-TETRAHYDRO-7H-PYRAZOLO[3,4-C]PYRIDIN-7-ONE
• CAS NO: 162142-14-5
• Molecular Formula: C₁₃H₁₉N₃O
• Molecular Weight: 233.31
• Mol File: 162142-14-5.mol

Chemical Properties

• Melting Point: 145-146 °C
• Boiling Point: 501.8±49.0 °C(Predicted)
• Appearance: /
• Density: 1.34±0.1 g/cm3(Predicted)
• PKA: 14.58±0.20(Predicted)
• CAS DataBase Reference: 1-CYCLOPENTYL-3-ETHYL-1,4,5,6-TETRAHYDRO-7H-PYRAZOLO[3,4-C]PYRIDIN-7-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CYCLOPENTYL-3-ETHYL-1,4,5,6-TETRAHYDRO-7H-PYRAZOLO[3,4-C]PYRIDIN-7-ONE(162142-14-5)
• EPA Substance Registry System: 1-CYCLOPENTYL-3-ETHYL-1,4,5,6-TETRAHYDRO-7H-PYRAZOLO[3,4-C]PYRIDIN-7-ONE(162142-14-5)

Safety Data

• Hazardous Substances Data: 162142-14-5(Hazardous Substances Data)

Upstream product

• 162142-22-5 3-hydroxy-1-(4-methoxyphenyl)-2-oxo-4-propionyl-1,2,5,6-tetrahydropyridine 
• 179171-55-2 3-methoxy-1-(4-methoxyphenyl)-2-oxo-4-propionyl-1,2,5,6-tetrahydropyridine 
• 30414-44-9 5-ethyltetrahydrofuran-2-ol 
• 695-06-7 hexan-4-olide 
• 208646-48-4 ethyl (4-methoxyphenylamino)propyl ketone 
• 162141-77-7 1-Cyclopentyl-3-ethyl-6-(4-methoxy-phenyl)-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one 

Downstream Products

• 185954-27-2 Tofimilast 

Relevant articles and documents

Process research and large-scale synthesis of a novel 5,6-dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-a]pyridine PDE-IV inhibitor

An efficient synthesis of the PDE IV inhibitor, 9H-cyclopentyl-7-ethyl-3-(thiophen-2-yl)-pyrazolo[3,4-c]-1,2,4-triazolo-5,6- dihydro-[4,3-a]pyridine 1 is described. Starting from commercially available γ-caprolactone, the synthesis was carried out in 10 steps. Key transformations were the selective O-methylation of diketone, 3-hydroxy-1-(4-methoxybenzyl)-4-propionyl-5,6-dihydro-1H-pyridin-2-one, with dimethyl sulfate and cesium carbonate in dimethylformamide, a one-pot pyrazole formation with subsequent acidic deprotection to provide lactam, 1-cyclopentyl-3-ethyl-1,4,5,6-tetrahydropyrazolo[3,4-c]pyridin-7-one, and finally the utilization of imidate, 1-cyclopentyl-7-ethoxy-3-ethyl-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine for the introduction of the triazole moiety. This process avoided the use of harsh reaction conditions, undesirable reagents and overcame the environmental concerns in the original synthesis.

Tricyclic 5,6-dihydro-9H-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridines

A compound of the formula wherein R1, R2, R3, R9 and R10 are as defined above. The compound of formula I and the pharmaceutically acceptable salts thereof are useful in inhibiting phosphodiesterase (PDE) type IV and the production of tumor necrosis factor (TNF) and in the treatment of asthma, arthritis, bronchitis, chronic obstructive airways disease, psoriasis, allergic rhinitis, dermatitis and other inflammatory diseases characterized by phosphodiesterase (PDE) Type IV activity as well as AIDS, sepsis, septic shock and other diseases, such as cachexia, involving the production of TNF

7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridines as novel inhibitors of human eosinophil phosphodiesterase

High-throughput file screening against inhibition of human lung PDE4 led to the discovery of 3-ethyl-1-(4-fluorophenyl)-6-phenyl-7-oxo-4,5,6,7,- tetrahydro-1H-pyrazolo[3,4-c]pyridine (11) as a novel PDE4 inhibitor. Subsequent SAR development, using an eosinophil PDE assay, led to analogues up to 50-fold more potent than 11 with IC50 values of 0.03-1.6 μM. One such compound, CP-220,629 (22) (IC50 = 0.44 μM), was efficacious in the guinea pig aerosolized antigen induced airway obstruction assay (ED50 2.0 mg/kg, po) and demonstrated a significant reduction in eosinophil (55%), neutrophil (65%), and IL-1β (82%) responses to antigen challenge in atopic monkeys (10 mg/kg, po).