30720-25-3

Usage

Uses

Used in Pharmaceutical Research and Development:
4-CHLORO-1-ETHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLIC ACID ETHYL ESTER is used as a chemical intermediate for the synthesis of potential pharmaceutical agents due to its unique molecular structure and the possibility of its interaction with biological targets.
Used in Chemical Synthesis:
In the chemical synthesis industry, 4-CHLORO-1-ETHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLIC ACID ETHYL ESTER serves as a key component in the creation of more complex molecules, potentially leading to new materials or compounds with specific properties.
Used in Industrial Applications:
Depending on its stability, reactivity, and other physical-chemical properties, 4-CHLORO-1-ETHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLIC ACID ETHYL ESTER may be employed in various industrial processes, such as in the development of new dyes, pigments, or other specialty chemicals.

InChI:InChI=1/C11H12ClN3O2/c1-3-15-10-7(6-14-15)9(12)8(5-13-10)11(16)17-4-2/h5-6H,3-4H2,1-2H3

Upstream product

• 30720-04-8 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 26823-99-4 [[(1-ethyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester 
• 3528-58-3 5-Amino-1-ethylpyrazole 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 118231-42-8 ethyl 1-ethyl-4-hydroxyamino-1H-pyrazolo<3,4-b>pyridine-5-carboxylate 
• 106811-04-5 6-ethyl-3-phenyl-6H-isoxazolo<3,4-d>pyrazolo<3,4-b>pyridine 
• 261771-29-3 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 
• 59060-16-1 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 
• 53064-94-1 4-(2-amino-anilino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 53065-02-4 4-(4-chloro-2-nitro-anilino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 34966-41-1 4-(butylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 34966-24-0 1-ethyl-4-isobutylamino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 1049619-86-4 C₁₈H₂₀N₄O₃ 
• 34966-42-2 4-anilino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 1049619-87-5 C₁₈H₁₉FN₄O₂ 
• 1340592-14-4 1-ethyl-4-(4-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 
• 1340592-15-5 [1-ethyl-4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-methyl-amine 
• 1340591-74-3 2-(3,5-bis-trifluoromethyl-phenyl)-N-[1-ethyl-4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N-methyl-isobutyramide 

Relevant academic research and scientific papers

Dual functional cholinesterase and PDE4D inhibitors for the treatment of Alzheimer's disease: Design, synthesis and evaluation of tacrine-pyrazolo[3,4-b]pyridine hybrids

A series of tacrine-pyrazolo[3,4-b]pyridine hybrids were synthesised and evaluated as dual cholinesterase (ChE) and phosphodiesterase 4D (PDE4D) inhibitors for the treatment of Alzheimer's disease (AD). Compound 10j, which is tacrine linked with pyrazolo[

PYRRAZOLOPYRIDINE DERIVATIVES

The present invention relates to a compound of formula (I), wherein R1 is hydrogen, lower alkyl, lower alkyl substituted by halogen, benzyl, -C(0)-lower alkyl, -C(0)-CH2-lower alkoxy, -C(0)-C3-6-cycloalkyl, -(CH2)°-C(0)-NR,R', -(CH2)°S(0)2- lower alkyl or -S(0)2-NR,R'; o is 0 or 1; R,R' are independently from each other hydrogen or lower alkyl, or may form together with the N atom to which they are attached a 5 or 6 membered heterocycloalkyl ring; R2 is hydrogen or lower alkyl; R3 is halogen, lower alkoxy, lower alkyl substituted by halogen or lower alkoxy substituted by halogen; and may be the same or different in case n is 2; n is 1 or 2; Ar is phenyl optionally substituted by one or two substituents selected from lower alkyl, halogen, lower alkoxy, lower alkyl substituted by hydroxy or cyano, or is a five or six membered heteroaryl group, selected from thiophenyl or pyridinyl which are optionally substituted by lower alkyl or halogen; or to a pharmaceutically active acid addition salt. It has surprisingly been found that the compounds of formula I show a high affinity simultaneously to both the NK1 and the NK3 receptors (dual NK1/NK3 receptor antagonists), useful in the treatment of schizophrenia.

PYRRAZOLOPYRIDINE COMPOUNDS AS DUAL NK1/NK3 RECEPTOR ANTAGONISTS

The present invention relates to a compound of formula I wherein R1, R2, R3, Ar, and n are as defined herein or to a pharmaceutically active acid addition salt. Compounds of formula I show a high affinity simultaneously to

The identification a novel, selective, non-steroidal, functional glucocorticoid receptor antagonist

The identification of novel, potent, non-steroidal/small molecule functional GR antagonist GSK1564023A selective over PR is described. Associated structure-activity relationships and the process of optimisation of an initial HTS hit are also described.

SUBSTITUTED PYRAZOLO [3,4-B]PYRIDINES AS PHOSPHODIESTERASE INHIBITORS

The present invention relates to phosphodiesterase (PDE) type IV selective inhibitors. Processes for the preparation of disclosed compounds, pharmaceutical compositions containing the disclosed compounds and their use as PDE type IV selective inhibitors are provided. Prepared compounds correspond to structure XIV.

Overall synthesis of GSK356278: Quick delivery of a PDE4 inhibitor using a fit-for-purpose approach

The family of phosphodiesterase (PDE) enzymes hydrolyse cyclic nucleotides, cAMP and cGMP, leading to their inactivation as intracellular second messengers. Inhibition of these enzymes leads to an elevation of levels of cyclic nucleotides in the cell and prolongs their action on downstream signaling pathways. PDE4, of which there are four subtypes, is widely expressed throughout the brain but is also abundant in the periphery in inflammatory and immune cells, in the gastrointestinal tract, and in cardiac myocytes. GSK356278 1 is a potent, selective, and competitive inhibitor of PDE4 enzymes currently under investigation for the treatment of CNS disorders. The initial synthetic route developed by Medicinal Chemistry Department, used several hazardous and/or expensive reagents and harsh conditions and gave relatively low yields. By targeted process of research and development plus application of analytical techniques to identify byproduct and extensive route scouting, a novel synthetic route for 1 has been developed. This contribution reports the optimisation of the chemical synthesis of 1 to develop a large-scale process suitable for its synthesis.

PYRAZOLO [3, 4-B] PYRIDINE DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS

The present invention relates to phosphodiesterase (PDE) type 4, phosphodiesterase (PDE) type 7 and dual PDE type 4 /PDE type 7 inhibitors. Compounds disclosed hereinf having the structure of Formula 1: can be useful in the treatment, prevention, inhibiti

PYRAZOLO (3, 4-B) PYRIDINE DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS

The present invention relates to phosphodiesterase (PDE) type 4, phosphodiesterase (PDE) type 7 and dual PDE type 4 /PDE type 7 inhibitors. Compounds disclosed herein having the structure of Formura 1: can be useful in the treatment, prevention, inhibitio

Pyrazolopyridines as a novel structural class of potent and selective PDE4 inhibitors

Optimisation of a high-throughput screening hit resulted in the discovery of 4-(substituted amino)-1-alkyl-pyrazolo[3,4-b]pyridine-5-carboxamides as potent and selective inhibitors of Phosphodiesterase 4 (PDE4). Herein, we describe early SAR studies around this novel template highlighting preferred substituents and rationalization of SAR through X-ray crystal structures of analogues bound to the PDE4 active site. Pyrazolopyridine 20a was found to be a potent and selective PDE4 inhibitor which also inhibits LPS induced TNF-α production from isolated human peripheral blood mononuclear cells and has an encouraging rat PK profile suitable for oral dosing.

SUBSTITUTED PYRAZOLO [3,4-B] PYRIDINES AS PHOSPHODIESTERASE INHIBITORS

The present invention relates to phosphodiesterase (PDE) type IV selective inhibitors. Processes for the preparation of disclosed compounds, pharmaceutical compositions containing the disclosed compounds and their use as PDE type IV selective inhibitors are provided. Prepared compounds correspond to structure XIV. Formula (XIV).