348640-05-1

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE is used as a pharmaceutical intermediate for the development of new drugs. Its unique structure and reactivity make it a valuable component in the synthesis of various medicinal compounds, potentially leading to the discovery of novel therapeutic agents.
Used in Organic Chemistry Research:
In the field of organic chemistry, 4-CHLORO-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE serves as a building block for the synthesis of complex organic molecules. Its versatile chemical properties allow for further functionalization and modification, facilitating the exploration of new chemical reactions and the creation of innovative organic compounds.

InChI:InChI=1/C14H11ClN2O2S/c1-10-2-4-11(5-3-10)20(18,19)17-9-7-12-13(15)6-8-16-14(12)17/h2-9H,1H3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 55052-28-3 4-chloro-7-azaindole 

Downstream Products

• 348640-92-6 1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile 
• 882033-47-8 4-chloro-1-(toluene-4-sulfonyl)-2-tributylstannanyl-1H-pyrrolo[2,3-b]pyridine 
• 1346175-14-1 4-[4-(4-fluorophenyl)-1-(methoxymethyl)-2-phenyl-1H-imidazol-5-yl]-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine 
• 1310735-06-8 N-cyclohexyl-5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-amine 
• 1310730-49-4 N⁴-cyclohexyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine 

Relevant academic research and scientific papers

TRICYCLIC JANUS KINASE 1 INHIBITORS, AND COMPOSITIONS AND METHODS THEREOF

Provided are novel class of therapeutics that are safe and effective inhibitors of Janus kinase 1 and pharmaceutical composition and methods of preparation and use thereof in the treatment of various diseases and disorders (e. g., inflammatory diseases, immune-mediated diseases or cancer).

4-chloro-3-nitro-1-p-toluenesulfonyl-7-azaindole derivative as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and particularly relates to a 4-chloro-3-nitro-1-p-toluenesulfonyl-7-azaindole derivative as well as a preparation method and application thereof. The invention relates to a 4-chloro-3-nitro-1-p-toluenesulfonyl-7-azaindole derivative which is specifically named as (2S,3S,4R,5S)-2-(hydroxymethyl)-6-(8b-nitro-4-p-toluenesulfonyl-4,8b-dihydro-[1,2,3]triazolepyrrolo(4-chloro)-pyridyl)-tetrahydropyran-3,4,5-triol.

Cyano-substituted cyclic hydrazine derivatives and application thereof

The invention provides cyano-substituted cyclic hydrazine derivatives. The cyano-substituted cyclic hydrazine derivatives are characterized in that the cyano-substituted cyclic hydrazine derivatives are compounds as shown in the following structural formula shown in the specification or stereoisomers, geometrical isomers, tautomers, racemates, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof; the compounds are useful for the prevention, treatment, treatment or amelioration of autoimmune diseases or proliferative diseases in patients, and/or for the inhibition or modulation of protein kinase activity.

Development, Optimization, and Structure-Activity Relationships of Covalent-Reversible JAK3 Inhibitors Based on a Tricyclic Imidazo[5,4- d]pyrrolo[2,3- b]pyridine Scaffold

Janus kinases are major drivers of immune signaling and have been the focus of anti-inflammatory drug discovery for more than a decade. Because of the invariable colocalization of JAK1 and JAK3 at cytokine receptors, the question if selective JAK3 inhibition is sufficient to effectively block downstream signaling has been highly controversial. Recently, we discovered the covalent-reversible JAK3 inhibitor FM-381 (23) featuring high isoform and kinome selectivity. Crystallography revealed that this inhibitor induces an unprecedented binding pocket by interactions of a nitrile substituent with arginine residues in JAK3. Herein, we describe detailed structure-activity relationships necessary for induction of the arginine pocket and the impact of this structural change on potency, isoform selectivity, and efficacy in cellular models. Furthermore, we evaluated the stability of this novel inhibitor class in in vitro metabolic assays and were able to demonstrate an adequate stability of key compound 23 for in vivo use.

Design, synthesis, and SAR study of highly potent, selective, irreversible covalent JAK3 inhibitors

Here, we report the design and synthesis of pyrimidinyl heterocyclic compounds containing terminal electrophiles as irreversible covalent JAK3 inhibitors that exploit a unique cysteine (Cys909) residue in JAK3. Investigation of the structure–activity relationship utilizing kinase assays resulted in the identification of potent and selective JAK3 inhibitors such as T1, T8, T15, T22, and T29. Among them, T29 was verified as a promising JAK3 irreversible inhibitor that possessed the best bioactivity and selectivity against JAKs and kinases containing a cysteine in the residue analogous to Cys909 in JAK3, suggesting that covalent modification of this Cys residue allowed the identification of a highly selective JAK3 inhibitor. Moreover, T29 also displayed a significant anti-inflammatory effect in ICR mice through the inhibition of increased paw thickness, which is worth further optimization to increase its potency and medicinal properties.

BIARYL KINASE INHIBITORS

The present disclosure is directed to biaryl compounds of formula (I) which can inhibit AAKl (adaptor associated kinase 1), compositions comprising such compounds and their use for treating e.g. pain, Alzheimer's disease, Parkinson's disease and schizophrenia.

AMINOACYLINDAZOLE IMMUNOMODULATORS FOR TREATMENT OF AUTOIMMUNE DISEASES

2-Acylindazole compounds of formula I or formula II are disclosed. These compounds inhibit Coagulation Factor XIIa. They are useful to treat autoimmune diseases.

Compounds used as JAK inhibitor, and use of compounds

The invention provides compounds used as a JAK inhibitor, and a use of the compounds, and concretely provides compounds (represented by formula (I)) with JAK inhibition activity or a stereoisomer, a geometric isomer, a tautomer, a racemate, a nitrogen oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, and a medicinal composition including the compounds. The invention also discloses a use of the compounds or the medicinal composition thereof in the preparation of medicines used for treating autoimmune diseases or proliferative diseases.

JAK INHIBITOR

The present invention discloses a series of JAK inhibitors, and particularly discloses a compound of formula (I) or a pharmaceutically acceptable salt thereof and the use thereof in preparation of drugs for treating diseases related to JAK.

SUBSTITUTED INDAZOLE COMPOUNDS AS IRAK4 INHIBITORS

The present invention provides substituted indazole compound of formula (I) and pharmaceutically acceptable salts thereof, and their use to inhibit IRAK4 and/or for the treatment of diseases or disorders induced by IRAK4.