533939-04-7

Usage

CAS Registry Number

63435-28-1

Type of Compound

Heterocyclic organic compound

Usage

Building block for various drugs and biologically active compounds in pharmaceutical and organic synthesis

Unique Value

Valuable component in the development of new therapeutic agents and drug discovery research due to its unique structure and properties.

InChI:InChI=1/C9H10N2/c1-2-8-4-3-7-5-6-10-9(7)11-8/h3-6H,2H2,1H3,(H,10,11)

Upstream product

• 1378685-98-3 C₉H₁₂N₂O 
• 4433-63-0 Ethyl boronic acid 
• 143468-07-9 6-Chloro-1-methoxycarbonyl-1H-pyrrolo<2,3-b>pyridine 
• 849068-50-4 ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate 

Downstream Products

• 533939-05-8 6-ethyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl-dimethyl-amine 
• 1420532-25-7 N-ethyl-N-(2-(6-ethyl-1H-pyrrolo[2,3-b]pyridin-1-yl)-5-(trifluoromethyl)benzyl)cyclopropanecarboxamide 
• 1420532-26-8 ?N-(2-(3-bromo-6-ethyl-1H-pyrrolo[2,3-b]pyridin-1-yl)-5-(trifluoromethyl)benzyl)-N-ethylcyclopropanecarboxamide 

Relevant academic research and scientific papers

Design and Synthesis of Potent and Selective PIM Kinase Inhibitors by Targeting Unique Structure of ATP-Binding Pocket

In the development of kinase inhibitors, one of the major concerns is selectivity. An effective strategy to achieve high selectivity is to utilize structural differences among kinases to inform inhibitor design. Here, we set out to improve the PIM (proviral integration site for Moloney murine leukemia virus) kinase-inhibitory selectivity of our previously reported 7-azaindole derivative 2, which has promising ADMET properties, by targeting a unique bulge in the ATP-binding pocket. 6-Substituted 7-azaindoles, especially the 6-chlorinated derivatives, proved to be potent and selective PIM kinase inhibitors and appear to be promising lead compounds for future drug discovery.

Structure-activity relationships (SAR) and structure-kinetic relationships (SKR) of bicyclic heteroaromatic acetic acids as potent CRTh2 antagonists II: Lead optimization

Extensive structure-activity relationship (SAR) and structure-kinetic relationship (SKR) studies in the bicyclic heteroaromatic series of CRTh2 antagonists led to the identification of several molecules that possessed both excellent binding and cellular potencies along with long receptor residence times. A small substituent in the bicyclic core provided an order of magnitude jump in dissociation half-lives. Selected optimized compounds demonstrated suitable pharmacokinetic profiles.

NEW CRTH2 ANTAGONISTS

The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

Discovery of [3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl] acetic acids as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications

Efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective [3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyridin-1-yl] acetic acid aldose reductase inhibitors. The lead candidate, [6-methyl-3-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyrrolo[2,3-b]pyri din-1-yl]acetic acid example 16, inhibits aldose reductase with an IC50 of 8 nM, while being inactive against aldehyde reductase (IC50 > 100 μM), a related enzyme involved in the detoxification of reactive aldehydes.

Substituted heteroarylalkanoic acids

Disclosed are substituted heteroarylalkanoic acids acids of the following formula D-A-C(O)R′, where D, A, and R′ are defined herein. These compounds are useful in the treatment of chronic complications arising from diabetes mellitus. Also disclosed are pharmaceutical compositions containing the compounds and methods of treatment employing the compounds, as well as methods for their synthesis.