37801-57-3

Usage

Uses

Used in Medicinal Chemistry:
ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE is used as a key intermediate in the synthesis of biologically active molecules for medicinal chemistry. Its unique structure allows for the creation of new drugs with potential therapeutic applications.
Used in Pharmaceutical Research:
In pharmaceutical research, ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE is utilized as a building block for developing new pharmaceuticals. Its properties make it a valuable component in the formulation of drugs aimed at treating a range of diseases and disorders.
Used in Agrochemicals:
ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE is used in agrochemicals for its potential applications in developing new compounds that can enhance crop protection and yield.
Used in Materials Science:
In the field of materials science, ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE is employed for its potential to contribute to the development of new materials with specific properties, such as those used in high-tech applications or advanced manufacturing processes.

InChI:InChI=1/C10H10ClN3O2/c1-3-16-10(15)7-4-12-9-6(8(7)11)5-13-14(9)2/h4-5H,3H2,1-2H3

Upstream product

• 1192-21-8 5-Amino-1-methylpyrazole 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 37799-77-2 diethyl 2-[(1-methyl-1H-pyrazol-5-ylamino)methylene]malonate 

Downstream Products

• 675111-93-0 N-benzyl-4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 675111-88-3 4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid 

Relevant academic research and scientific papers

Identification of pyrazolopyrimidine arylsulfonamides as CC-chemokine receptor 4 (CCR4) antagonists

A novel 4-aminoindazole sulfonamide hit (13) was identified as a human CCR4 antagonists from testing a focussed library of compounds in the primary GTPγS assay. Replacing the indazole core with a pyrazolopyrimidine, and introduction of a methoxy group adjacent to the sulfonamide substituent, resulted in the identification of pyrazolopyrimidine 37a, which exhibited good binding affinity in the GTPγS assay (pIC50 = 7.2), low lipophilicity (c log P = 2.2, chromlog D7.4 = 2.4), high LE (0.41), high solubility (CLND solubility ≥581 μM), and an excellent PK profile in both the rat (F = 62%) and the dog (F = 100%). Further SAR investigation of the pyrazolopyrimidine suggested that substitution at N1 is tolerated, providing a suitable vector to modulate the properties, and increase the potency in a lead optimisation campaign.

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.

PYRAZOLO[3,4-B]PYRIDINE COMPOUNDS, AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS

The invention relates to a compound of formula (I) or a salt thereof: wherein:R1 is C1-4alkyl, C1-3fluoroalkyl, -CH2CH2OH or -CH2CH2CO2C1-2alkyl;R2 is a hydrogen atom (H), methyl or C1fluoroalkyl;R3 is optionally substituted C3-8cycloalkyl or optionally substituted mono-unsaturated-C5-7cycloalkenyl or an optionally substituted heterocyclic group of sub-formula (aa), (bb) or (cc); in which n1 and n2 independently are 1 or 2; and in which Y is O, S, SO2, or NR10; or R3 is a bicyclic group (dd) or (ee): ; and wherein X is NR4R5 or OR5a. The compounds are phosphodiesterase (PDE) inhibitors, in particular PDE4 inhibitors. Also provided is the use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment and/or prophylaxis of an inflammatory and/or allergic disease in a mammal such as a human, for example chronic obstructive pulmonary disease (COPD), asthma, or allergic rhinitis.

Discovery of new orally active phosphodiesterase (PDE4) inhibitors

A series of 4-anilinopyrazolopyridine derivatives were synthesized and biologically evaluated as inhibitors of phosphodiesterase (PDE4). Chemical modification of 3, a structurally new chemical lead that was found in our in-house library, was focused on 1- and 3-substituents. Full details of the discovery of a new orally active chemical lead 5 are presented. Structure-activity relationship data, pharmacological evaluation, and the subtype selectivity study are also presented.