361162-95-0

Basic information

• Product Name: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile
• Synonyms: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile;6-AMino-4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethyloxyquinoline;6-AMino-4-[(3-chloro-4-fluorophenyl)aMino]-7-ethoxy-3-quinolinecarbonitrile;3-Quinolinecarbonitrile, 6-aMino-4-[(3-chloro-4-fluorophenyl)aMino]-7-ethoxy-
• CAS NO: 361162-95-0
• Molecular Formula: C₁₈H₁₄ClFN₄O
• Molecular Weight: 357
• EINECS: 1312995-182-4
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 361162-95-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 533.385°C at 760 mmHg
• Flash Point: 276.382°C
• Appearance: /
• Density: 1.421g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: Refrigerator
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile(361162-95-0)
• EPA Substance Registry System: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile(361162-95-0)

Safety Data

• Hazardous Substances Data: 361162-95-0(Hazardous Substances Data)

Usage

Description

6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile is an organic compound characterized by its brown solid appearance. It is an intermediate in the preparation of Tyrosine Kinase Inhibitors, which are significant in the pharmaceutical industry due to their potential applications in cancer treatment and other therapeutic areas.

Uses

Used in Pharmaceutical Industry:
6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile is used as an intermediate for the synthesis of Tyrosine Kinase Inhibitors. These inhibitors play a crucial role in the development of targeted cancer therapies, as they can help regulate the activity of enzymes involved in cell signaling pathways that contribute to tumor growth and progression.
6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile's chemical structure allows it to be a valuable building block in the creation of more complex molecules with specific biological activities. Its use in the pharmaceutical industry is primarily driven by the need for novel and effective treatments for various types of cancer, where Tyrosine Kinase Inhibitors have shown promise in clinical trials and research studies.

InChI:InChI=1/C18H14ClFN4O/c1-2-25-17-7-16-12(6-15(17)22)18(10(8-21)9-23-16)24-11-3-4-14(20)13(19)5-11/h3-7,9H,2,22H2,1H3,(H,23,24)

Upstream product

• 367-21-5 3-chloro-4-fluorophenylamine 
• 106579-00-4 5-methoxy-2-methyl-4-nitroaniline 
• 116435-75-7 3-(ethyloxy)-4-nitroaniline 
• 361162-90-5 5-methoxy-2-methyl-4-nitroacetanilide 
• 361162-91-6 5-ethoxy-2-methyl-4-nitroacetanilide 
• 909513-02-6 (E)-2-Cyano-3-(3-ethoxy-phenylamino)-acrylic acid ethyl ester 
• 214476-09-2 4-Chloro-7-ethoxy-6-nitro-quinoline-3-carbonitrile 
• 214476-08-1 7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile 
• 492456-51-6 (E)-2-Cyano-3-(3-ethoxy-4-nitro-phenylamino)-acrylic acid ethyl ester 
• 1313378-64-1 N-[4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl]acetamide hydrochloride 
• 7439-89-6 iron 
• 915945-40-3 3-cyano-4-(3-chloro-4-fluoroanilino)-7-ethoxy-N-phthalimidyl-quinoline 
• 848655-77-6 N-(4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl)acetamide 
• 1201080-09-2 N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide 

Downstream Products

• 492456-86-7 N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxy-6-quinolinyl]-2-butenamide 
• 257933-82-7 pelitinib 
• 1245710-86-4 {(E)-3-[4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-ylcarbamoyl]-allyl}prop-2-ynyl carbamic acid tert-butyl ester 
• 915788-23-7 {(E)-3-[4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-ylcarbamoyl]-allyl}-methylcarbamic acid tert-butyl ester 
• 1245710-88-6 (E)-pent-2-en-4-ynoic acid [4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl]-amide 
• 1245711-05-0 (E)-4-(methylamino)-but-2-enoic acid [4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl]amide hydrochloride 
• 1245710-91-1 (E)-4-[(2-fluoroethyl)methylamino]-but-2-enoic acid [4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl]amide 
• 1245710-93-3 (E)-4-[(4-fluorobenzyl)methylamino]-but-2-enoic acid [4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl] amide 
• 1360430-63-2 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)acrylamide 
• 1360430-72-3 3-chloro-N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide 
• 1360430-64-3 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-(dimethylamino)propanamide 
• 1360430-65-4 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-piperidin-1-ylpropanamide 
• 1360430-66-5 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-morpholinopropanamide 

Relevant articles and documents

1,2-DITHIOLANE AND DITHIOL COMPOUNDS USEFUL IN TREATING MUTANT EGFR-MEDIATED DISEASES AND CONDITIONS

Compositions of the invention comprise 1,2-dithiolane, dithiol and related compounds useful as therapeutic agents for the treatment and prevention of diseases and conditions associated with aberrant EGFR activity.

Irreversible inhibition of epidermal growth factor receptor activity by 3-aminopropanamides

Irreversible epidermal growth factor receptor (EGFR) inhibitors contain a reactive warhead which covalently interacts with a conserved cysteine residue in the kinase domain. The acrylamide fragment, a commonly employed warhead, effectively alkylates Cys797 of EGFR, but its reactivity can cause rapid metabolic deactivation or nonspecific reactions with off-targets. We describe here a new series of irreversible inhibitors containing a 3-aminopropanamide linked in position 6 to 4-anilinoquinazoline or 4-anilinoquinoline-3- carbonitrile driving portions. Some of these compounds proved to be as efficient as their acrylamide analogues in inhibiting EGFR-TK (TK = tyrosine kinase) autophosphorylation in A549 lung cancer cells. Moreover, several 3-aminopropanamides suppressed proliferation of gefitinib-resistant H1975 cells, harboring the T790M mutation in EGFR, at significantly lower concentrations than did gefitinib. A prototypical compound, N-(4-(3-bromoanilino)quinazolin-6- yl)-3-(dimethylamino)propanamide (5), did not show covalent binding to cell-free EGFR-TK in a fluorescence assay, while it underwent selective activation in the intracellular environment, releasing an acrylamide derivative which can react with thiol groups.

USE OF CYANOQUINOLINES FOR TREATING OR INHIBITING COLONIC POLYPS

This invention provides a method of treating or inhibiting colonic polyps which comprises providing a compound of formula (1); wherein R1, R2, R3, R4, X, Y, and n are defined hereinbefore, or a pharmaceutically acceptable salt thereof.