29274-22-4

Usage

Uses

Used in Pharmaceutical Industry:
5-Hydroxypyrazolo[1,5-a]pyrimidine is used as a therapeutic agent for the treatment of erectile dysfunction. By inhibiting PDE5, it promotes vasodilation and increased blood flow, which can help alleviate the symptoms of erectile dysfunction. Its pharmaceutical potential has led to its inclusion as a key component in the development of medications like Viagra, making it an essential part of modern erectile dysfunction treatment options.

InChI:InChI=1/C6H5N3O/c10-6-2-4-9-5(8-6)1-3-7-9/h1-4H,(H,8,10)

Upstream product

• 874-14-6 1,3-dimethyluracil 
• 1225387-53-0 3⁽⁵⁾-aminopyrazole 
• 1001-26-9 ethyl 3-ethoxyacrylate 
• 922-67-8 propynoic acid methyl ester 
• 1224944-43-7 sodium pyrazolo[1,5-a] pyrimidin-5-olate 
• 1820-80-0 3-aminopyrazole 
• 623-47-2 propynoic acid ethyl ester 
• 89464-32-4 prop-2-ynylcarbamic acid ethyl ester 
• 105-37-3 Ethyl propionate 
• 5941-55-9 ethyl 3-ethoxyacrylate 

Downstream Products

• 29274-25-7 4-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one 
• 29274-24-6 5-chloropyrazolo[1,5-a]pyrimidine 
• 1224944-45-9 methyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 1224944-48-2 5-chloro-N-cyclohexylpyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-62-0 5-chloro-N-(3-(5-chloro-2-methylphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224942-00-0 5-amino-N-(3-(5-chloro-2-methylphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-49-3 5-chloro-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-72-2 5-chloro-N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224942-05-5 N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)-5-(cyclopropylmethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224939-88-1 5-amino-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-51-7 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester 
• 1224939-90-5 methyl 5-(3-fluorobenzylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 1224944-68-6 5-chloro-N-(3-(2,5-dimethylphenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1224944-67-5 5-chloro-N-(3-(2,5-dimethylphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of macrocyclic derivatives as TRK inhibitors

Tropomyosin receptor kinases (TRKA, TRKB, TRKC) are transmembrane receptor tyrosine kinases, which are respectively encoded by NTRK1, NTRK2, and NTRK3 genes. Herein, we reported the design, synthesis and Structure-Activity Relationship (SAR) investigation of a series of macrocyclic derivatives as new TRK inhibitors. Among these compounds, compound 9e exhibited strong kinase inhibitory activity (TRKG595R IC50 = 13.1 nM) and significant antiproliferative activity in the Ba/F3-LMNA-NTRK1 cell line (IC50 = 0.080 μM) and compound 9e has shown a better inhibitory effect (IC50 = 0.646 μM) than control drug LOXO-101 in Ba/F3-LMNA-NTRK1-G595R cell line. These results indicate that compound 9e is a potential TRK inhibitor for further investigation.

Preparation and application of protein receptor kinase inhibitor

The invention provides a preparation method of a protein receptor kinase inhibitor. Specifically, the invention discloses a compound as shown in a formula I or a stereoisomer or racemate or pharmaceutically acceptable salt thereof, and the definition of each group is as shown in the specification. The invention also discloses application of the compound as a TRK kinase inhibitor.

Optimization of pyrazolo[1,5-a]pyrimidines lead to the identification of a highly selective casein kinase 2 inhibitor

Casein kinase 2 (CK2) is a constitutively expressed serine/threonine kinase that has a large diversity of cellular substrates. Thus, CK2 has been associated with a plethora of regulatory functions and dysregulation of CK2 has been linked to disease development in particular to cancer. The broad implications in disease pathology makes CK2 an attractive target. To date, the most advanced CK2 inhibitor is silmitasertib, which has been investigated in clinical trials for treatment of various cancers, albeit several off-targets for silmitasertib have been described. To ascertain the role of CK2 inhibition in cancer, other disease and normal physiology the development of a selective CK2 inhibitor would be highly desirable. In this study we explored the pyrazolo [1,5-a]pyrimidine hinge-binding moiety for the development of selective CK2 inhibitors. Optimization of this scaffold, which included macrocyclization, led to IC20 (31) a compound that displayed high in vitro potency for CK2 (KD = 12 nM) and exclusive selectivity for CK2. X-ray analysis revealed a canonical type-I binding mode for IC20 (31). However, the polar carboxylic acid moiety that is shared by many CK2 inhibitors including silmitasertib was required for potency but limits the cellular activity of IC20 (31) and the cellular IC50 dropped to the low micromolar range. In summary, IC20 (31) represents a highly selective and potent inhibitor of CK2, which can be used as a tool compound to study CK2 biology and potential new applications for the treatment of diseases.

Method for efficiently synthesizing 5-chloropyrazolo[1,5-a]pyrimidine

The invention discloses a method for efficiently synthesizing 5-chloropyrazolo[1,5-a]pyrimidine. The synthesis route comprises: carrying out a reaction on a compound A and a compound B to obtain a compound C, and carrying out a reaction on the compound C and phosphorus oxychloride to obtain a compound D, ie., 5-chloropyrazolo[1,5-a]pyrimidine, wherein the reaction formulas A, B, C and D are defined in the specification. According to the present invention, the method has characteristics of mild synthesis condition, low influence of post-treatment on environment, simple process, inexpensive andeasily-available raw material, simple operation and wide industrial application prospect and market value, and is suitable for industrial large-scale production.

COMPOUNDS AND THEIR METHODS OF USE

The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including Dravet syndrome or epilepsy are also provided herein.

Heterocyclic Compound

The present invention provide a compound having an orexin receptor antagonistic activity, which is expected to be useful as medicaments such as agents for the prophylaxis or treatment of sleep disorder, depression, anxiety disorder, panic disorder, schizophrenia, drug dependence, Alzheimer's disease and the like. The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.

Pyrazolo [1, 5 - a] pyrimidine compounds and their preparation method and medical use

The invention relates to a pyrazolo[1,5-a]miazine compound and its preparation method and medical use. The invention relates to the preparation method of the pyrazolo[1,5-a]miazine compound shown in the general formula (I) and its salt, a pharmaceutical c

Concise and Efficient Access to 5,7-Disubstituted Pyrazolo[1,5-a]pyrimidines by Pd-Catalyzed Sequential Arylation, Alkynylation and SNAr Reaction

A simple and efficient method for synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines is reported. The synthetic route involved first a one-pot two-step synthesis of 7-substituted pyrazolo[1,5-a]pyrimidin-5-ones from the reaction of 3-aminopyrazole 1 with activated alkynes. These compounds were used as key intermediates to access, with excellent yields, a library of new 5,7-disubstituted pyrazolo[1,5-a]pyrimidines, which are known for their wide range of biological activities, through C–O bond activation with PyBroP (bromotripyrrolidinophosphonium hexafluorophosphate) as an activator reagent.

FUSED RING HETEROARYL COMPOUNDS AND THEIR USE AS TRK INHIBITORS

The disclosure provides novel chemical compounds represented by Formula I or a pharmaceutically acceptable salt, solvate, polymorph, ester, tautomer or prodrug thereof. The compounds can be used as an inhibitor of Trk and are useful in the treatment of pain, cancer, inflammation, neurodegenerative disease and certain infectious diseases. In some compounds of Formula I, Q is —CH═CR3C(O)NR4R5, —C≡CC(O)NR4R5, or

COMBINATION OF KINASE INHIBITORS AND USES THEREOF

The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth. The present invention also provides a pharmaceutical kit effective for treating a disease condition associated with PI3 -kinase α and/or mTOR in a subject.