1082745-49-0

Basic information

• Product Name: 1H-Pyrazole-4-carbonitrile, 5-amino-1-(tetrahydro-2H-pyran-4-yl)-
• Synonyms: 1H-Pyrazole-4-carbonitrile, 5-amino-1-(tetrahydro-2H-pyran-4-yl)-;5-aMino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carbonitrile;5-AMino-1-(tetrahydro-pyran-4-yl)-1H-pyrazole-4-carbonitrile;EOS-62039
• CAS NO: 1082745-49-0
• Molecular Formula: C₉H₁₂N₄O
• Molecular Weight: 192.21778
• Mol File: 1082745-49-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 432.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 0.14±0.19(Predicted)
• CAS DataBase Reference: 1H-Pyrazole-4-carbonitrile, 5-amino-1-(tetrahydro-2H-pyran-4-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-4-carbonitrile, 5-amino-1-(tetrahydro-2H-pyran-4-yl)-(1082745-49-0)
• EPA Substance Registry System: 1H-Pyrazole-4-carbonitrile, 5-amino-1-(tetrahydro-2H-pyran-4-yl)-(1082745-49-0)

Safety Data

• Hazardous Substances Data: 1082745-49-0(Hazardous Substances Data)

Usage

General Description

The chemical "1H-Pyrazole-4-carbonitrile, 5-amino-1-(tetrahydro-2H-pyran-4-yl)-" is a compound with the molecular formula C11H13N3O, which consists of a pyrazole ring with a carbonitrile group and an amino group attached to a tetrahydro-2H-pyran-4-yl moiety. It is a heterocyclic compound that may have potential applications in medicinal chemistry and drug development due to its unique structure and potential biological activities. Further research and study are required to fully understand the properties and potential uses of this chemical.

InChI:InChI=1S/C9H12N4O/c10-5-7-6-12-13(9(7)11)8-1-3-14-4-2-8/h6,8H,1-4,11H2

Upstream product

• 672-81-1 2-(methoxymethylene)malononitrile 
• 123-06-8 Ethoxymethylenemalononitrile 
• 116312-69-7 tetrahydro-2H-pyran-4-yl-hydrazine 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 693287-79-5 N’-(tetrahydropyran-4-yl)hydrazinecarboxylic acid tert-butyl ester 
• 693287-78-4 N’-(tetrahydropyran-4-ylidene)hydrazinecarboxylic acid tert-butyl ester 

Downstream Products

• 1082745-50-3 5-amino-1-(tetrahydropyran-4-yl)-1H-pyrazole-4-carboxylic acid amide 
• 1082744-06-6 6-((3S,4S)-1-benzyl-4-ethylpyrrolidin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 1082743-98-3 6-((3S,4S)-1-(3-fluorobenzyl)-4-methylpyrrolidin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 1082744-05-5 6-((3S,4S)-1-(4-fluorobenzyl)-4-methylpyrrolidin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 1082744-10-2 6-((3S,4S)-1-(4-methoxybenzyl)-4-methylpyrrolidin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 1082744-20-4 6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 1189767-09-6 6-benzyl-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 1082743-70-1 6-((3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 1236858-52-8 PF-04449613 
• 1236858-84-6 4-[(1-{1-[4-oxo-1-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl]ethyl}azetidin-3-yl)oxy]benzonitrile 
• 1548588-46-0 6-(phenoxymethyl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of Dual-Target Inhibitors of Acetylcholinesterase (AChE) and Phosphodiesterase 9A (PDE9A) for the Treatment of Alzheimer's Disease

A series of dual-target AChE/PDE9A inhibitor compounds were designed, synthesized, and evaluated as anti-Alzheimer's Disease (AD) agents. Among these target compounds, 11a (AChE: IC50 = 0.048 μM; PDE9A: IC50 = 0.530 μM) and 11b (AChE: IC50 = 0.223 μM; PDE9A: IC50 = 0.285 μM) exhibited excellent and balanced dual-target AChE/PDE9A inhibitory activities. Meanwhile, those two compounds possess good blood-brain barrier (BBB) penetrability and low neurotoxicity. Especially, 11a and 11b could ameliorate learning deficits induced by scopolamine (Scop). Moreover, 11a could also improve cognitive and spatial memory in Aβ25-35-induced cognitive deficit mice in the Morris water-maze test. In summary, our research developed a series of potential dual-target AChE/PDE9A inhibitors, and the data indicated that 11a was a promising candidate drug for the treatment of AD.

PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE DERIVATIVES AS PDE9 INHIBITORS

A compound of the general formula (I) wherein R1 is selected from the group consisting of phenyl unsubstituted or substituted with 1 to 3 substituents selected from F, Cl, Br, I, CN, -O-C1-C3-alkyl, fluorinated -O-C1-C3-alkyl, -(CH2)mOH and 5-membered heterocyclic group with 1 or 2 heteroatoms selected from N, O and S; and 6- or 10-membered heteroaryl with 1 to 3 heteroatoms selected from O, N and S; R2 and R3 independently of each other represent H atom or straight or branched C1-C3 alkyl; R4 is selected from the group consisting of 4- to 6- membered cycloalkyl, wherein one of carbon atoms can be replaced by O atom, and which is unsubstituted or substituted with one or two halogen atoms,and straight or branched C1-C4 alkyl; Q represents a bond or C1-C3-alkylene, which can be optionally substituted by one to three C1-C3-alkyls; X is selected from the group consisting of O, NR5, and S(O)p; R5 represents H atom or C1-C3alkyl; m is 1, 2 or 3; p is 0, 1 or 2; and salts thereof, for use as a medicament, in particular for treating cognitive function disorders and neurodegenerative diseases.

Application of structure-based drug design and parallel chemistry to identify selective, brain penetrant, in vivo active phosphodiesterase 9A inhibitors

Phosphodiesterase 9A inhibitors have shown activity in preclinical models of cognition with potential application as novel therapies for treating Alzheimers disease. Our clinical candidate, PF-04447943 (2), demonstrated acceptable CNS permeability in rats with modest asymmetry between central and peripheral compartments (free brain/free plasma = 0.32; CSF/free plasma = 0.19) yet had physicochemical properties outside the range associated with traditional CNS drugs. To address the potential risk of restricted CNS penetration with 2 in human clinical trials, we sought to identify a preclinical candidate with no asymmetry in rat brain penetration and that could advance into development. Merging the medicinal chemistry strategies of structure-based design with parallel chemistry, a novel series of PDE9A inhibitors was identified that showed improved selectivity over PDE1C. Optimization afforded preclinical candidate 19 that demonstrated free brain/free plasma ≥1 in rat and reduced microsomal clearance along with the ability to increase cyclic guanosine monophosphosphate levels in rat CSF.