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Usage

Uses

Used in Pharmaceutical Industry:
1H-Pyrazolo[4,3-b]pyridine is used as a bioactive agent for its potential antimicrobial, antiviral, and anticancer properties. It is being investigated for its ability to target and combat various pathogens and cancer cells, offering a promising avenue for the development of new drugs.
Used in Organic Synthesis:
1H-Pyrazolo[4,3-b]pyridine serves as a building block in organic synthesis, contributing to the creation of complex molecular structures and novel compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.
Used as a Precursor in Chemical Synthesis:
1H-Pyrazolo[4,3-b]pyridine is utilized as a precursor for the synthesis of other bioactive compounds, enabling the development of a diverse range of chemical entities with potential therapeutic and industrial applications. Its unique structure and reactivity make it a valuable component in the synthesis of innovative and effective molecules.

InChI:InChI=1/C6H5N3/c1-2-5-6(7-3-1)4-8-9-5/h1-4H,(H,8,9)

Upstream product

• 25976-65-2 2-pyridinecarboxaldehyde hydrazone 
• 372-47-4 3-Fluoropyridine 
• 52090-62-7 1-(1H-pyrazolo[4,3-b]pyridin-1-yl)-ethan-1-one 
• 31224-43-8 3-fluoropyridine-2-carbaldehyde 

Downstream Products

• 1259851-62-1 C₁₁H₁₂IN₃O₂ 
• 1294514-46-7 C₃₀H₄₀N₄O₅Si 
• 1432112-05-4 2-(2-chloro-4-{[1-(4-methoxybenzyl)-1H-pyrazolo[4,3b]pyridin-3-yl]amino}phenyl)-4-methyl-1H-isoindole-1,3(2H)-dione 
• 1432112-10-1 N-(2-chlorophenyl)-4-{[1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]amino}benzenesulfonamide 
• 1432112-20-3 N-(3,4-dichlorophenyl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-3-amine 
• 1432111-98-2 3-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridine 
• 1432135-75-5 N-(2-chloro-4-{[1-(4-methoxybenzyl)-1H-pyrazolo[4.3-b]pyridin-3-yl]amino}phenyl)acetamide 
• 1432112-24-7 2-chloro-N⁴-[1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]benzene-1,4-diamine 
• 1432112-27-0 2-(2-chloro-4-{[1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]amino}phenyl)-1H-pyrrolo[3,4-c] pyridine-1,3(2H)-dione 
• 1432111-05-1 2-[2-chloro-4-(1H-pyrazolo[4,3-b]pyridin-3-ylamino)phenyl]-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione 
• 1432112-28-1 2-chloro-N-(2-chloro-4-{[1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]amino}phenyl)-4-fluorobenzamide 
• 1432112-01-0 N-(4-chloro-3-methoxyphenyl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-3-amine 

Relevant academic research and scientific papers

Palladium-Catalyzed C3-Arylations of 1H- and 2H-Pyrazolo[4,3- b]pyridines on Water

Direct C3-arylation of 1H-pyrazolo[4,3-b]pyridines and direct C3-arylation of 2H-pyrazolo[4,3-b]pyridines in water has been developed. A new protocol for a sequential C3-arylation procedure on a mixture of 1H- and 2H-pyrazolo[4,3-b]pyridines followed by in situ PMB cleavage has also been achieved. This procedure led to unprotected (NH) C3-arylated 1H-pyrazolo[4,3-b]pyridines in good yields.

Palladium-Catalyzed Regioselective C?H Arylation of 4-Azaindazole at C3, C5 and C7 Positions

Direct and site-selective C5 and C7 palladium-catalyzed C?H arylations of 4-azaindazole N-oxide have been achieved. A bidentate ligand and Pd(OAc)2 catalyst in toluene promoted the activation of C5 position, while a phosphine ligand and PdCl2 catalyst in DMA directed the arylation at C7 position. Using this new method, the synthesis of C5, C7-diarylated 4-azaindazole N-oxides as well as the C3, C5, C7-triarylated 4-azaindazoles was achieved towards future medicinal compounds development. (Figure presented.).

PYRIDINE AND PYRIMIDINE DERIVATIVES AND THEIR USE IN TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA

Provided herein is a compound of formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer,or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing influenza.

PYRIMIDINE AND PYRIDINE DERIVATIVES AND USE IN TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA THEREOF

Provided herein is a compound of formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing influenza.

Discovery, Synthesis, and Preclinical Characterization of N-(3-Chloro-4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine (VU0418506), a Novel Positive Allosteric Modulator of the Metabotropic Glutamate Receptor 4 (mGlu4)

The efficacy of positive allosteric modulators (PAMs) of the metabotropic glutamate receptor 4 (mGlu4) in preclinical rodent models of Parkinson's disease has been established by a number of groups. Here, we report an advanced preclinically characterized mGlu4 PAM, N-(3-chloro-4-fluorophenyl)-1H-pyrazolo[4,3-b]pyridin-3-amine (VU0418506). We detail the discovery of VU0418506 starting from a common picolinamide core scaffold and evaluation of a number of amide bioisosteres leading to the novel pyrazolo[4,3-b]pyridine head group. VU0418506 has been characterized as a potent and selective mGlu4 PAM with suitable in vivo pharmacokinetic properties in three preclinical safety species.

PYRROLOPYRAZINE KINASE INHIBITORS

The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

Optimisation of ITK inhibitors through successive iterative design cycles

Based on a hit cluster of compounds inhibiting interleukin-2 inducible T-cell kinase (ITK) in the submicromolar range a series of ITK inhibitor libraries were synthesized. Through iterative design cycles including kinase crystal structure information, indolylindazole libraries were identified which showed low nanomolar activity in enzymatic and cellular assays. The potential of these novel lead series was confirmed through in vivo tests in an anti-CD3-IL2 mouse model. The intravenous administration of highly potent ITK inhibitor 11o resulted in dose-dependent, efficient suppression of IL-2.

PYRAZOLOPYRIDINE, PYRAZOLOPYRAZINE, PYRAZOLOPYRIMIDINE, PYRAZOLOTHIOPHENE AND PYRAZOLOTHIAZOLE COMPOUNDS AS MGLUR4 ALLOSTERIC POTENTIATORS, COMPOUNDS, AND METHODS OF TREATING NEUROLOGICAL DYSFUNCTION

Pyrazolopyridine, pyrazolopyrazine, pyrazolopyrimidine, pyrazolothiophene and pyrazolothiazole compounds which are useful as allosteric potentiators/positive allosteric modulators of the metabotropic glutamate receptor subtype 4 (mGluR4); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds, for example, in treating neurological and psychiatric disorders or other disease state associated with glutamate dysfunction.

Identification of potent ITK inhibitors through focused compound library design including structural information

A series of novel compound libraries inhibiting interleukin-2 inducible T cell kinase (ITK) were designed, synthesized and evaluated. In the first design cycle two library scaffolds were identified showing low micromolar inhibition of ITK. Further iterative design cycles including crystal structure information of ITK and structurally related kinases led to the identification of indolylindazole and indolylpyrazolopyridine compounds with low nanomolar ITK inhibition.