957881-03-7

Basic information

• Product Name: AZD1152
• Synonyms: 3-[[7-[3-[Ethyl[2-(phosphonooxy)ethyl]amino]propoxy]-4-quinazolinyl]amino]-N-(3-fluorophenyl)-1H-pyrazole-5-acetamide;AZD1152 (Barasertib);2-(ETHYL(3-((4-((5-(2-((3-FLUOROPHENYL)AMINO)-2-OXOETHYL)-1H-PYRAZOL-3-YL)AMINO)QUINAZOLIN-7-YL)OXY)PROPYL)AMINO)ETHYL DIHYDROGEN PHOSPHATE
• CAS NO: 957881-03-7
• Molecular Formula: C₂₆H₃₁FN₇O₆P
• Molecular Weight: 586.5318642
• EINECS: -0
• Product Categories: Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 957881-03-7.mol

Chemical Properties

• Appearance: /
• Density: 1.463
• CAS DataBase Reference: AZD1152(CAS DataBase Reference)
• NIST Chemistry Reference: AZD1152(957881-03-7)
• EPA Substance Registry System: AZD1152(957881-03-7)

Safety Data

• Hazardous Substances Data: 957881-03-7(Hazardous Substances Data)

Usage

Uses

Used in Oncology:
AZD1152 is used as an anticancer agent for the treatment of patients with advanced solid tumors. Its mechanism of action involves the inhibition of Aurora kinases, which play a crucial role in the regulation of the cell cycle and are often overexpressed or mutated in cancer cells. This inhibition can lead to the prevention of tumor growth and the reduction of cancer cell proliferation.

Upstream product

• 722544-46-9 2-(5-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-2H-pyrazol-3-yl)-N-(3-fluorophenyl)acetamide 
• 174891-10-2 (5-amino-2H-pyrazol-3-yl)acetic acid 
• 722544-51-6 N-(3-fluorophenyl)-2-{3-[(7-{3-[ethyl(2-hydroxyethyl)amino]propoxy}quinazolin-4-yl)amino]-1H-pyrazol-5-yl}acetamide 
• 722544-50-5 di-tert-butyl 2-[[3-({4-[(5-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-3-yl)amino]quinazolin-7-yl}oxy)propyl](ethyl)amino]ethyl phosphate 
• 557770-89-5 4-(3-phenylpropylamino)-7-(2-chloroethoxy)quinazoline 
• 557770-90-8 4-chloro-7-(3-chloropropoxy)quinazoline 
• 557770-91-9 2-(3-((7-(3-chloropropoxy)quinazolin-4-yl)amino)-1H-pyrazol-5-yl)acetic acid 
• 16499-57-3 7-fluoro-3H-quinazolin-4-one 
• 446-32-2 4-fluoroanthranilic acid 
• 372-19-0 meta-fluoroaniline 

Relevant articles and documents

PROCESS AND INTERMEDIATE

The invention relates to a new process useful in the preparation of pharmaceutical compounds such as 2-{ethyl[3-({4-[(5-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazol-3-yl)amino]quinazolin-7-yl}oxy)propyl]amino}ethyl dihydrogen phosphate (AZD1152) and intermediates used therein.

MALEATE CO-CRYSTAL OF AZD1152

The present invention relates to a novel co-crystal of 2-{cthyl[3-( {4-[(5- {2-[(3-fluorophenyl)amino]-2-oxoethyl}-IH-pyrazol-3-yl)amino]quinazolin-7- yl}oxy)propyl]amino} ethyl dihydrogen phosphate (AZDl 152) which is an aurora kinase inhibitor that is useful in the treatment of hyperproliferative diseases such as cancer.

COMBINATION THERAPY FOR THE TREATMENT OF CANCER

A combination comprising an aurora kinase inhibitor and an efflux transporter inhibitor wherein the aurora kinase inhibitor is a compound of formula (I) or pharmaceutically acceptable salt thereof for use in the treatment of hyperproliferative diseases such as cancer.

Discovery, synthesis, and in vivo activity of a new class of pyrazoloquinazolines as selective inhibitors of aurora B kinase

The Aurora kinases have been the subject of considerable interest as targets for the development of new anticancer agents. While evidence suggests inhibition of Aurora B kinase gives rise to the more pronounced antiproliferative phenotype, the most clinically advanced agents reported to date typically inhibit both Aurora A and B. We have discovered a series of pyrazoloquinazolines, some of which show greater than 1000-fold selectivity for Aurora B over Aurora A kinase activity, in recombinant enzyme assays. These compounds have been designed for parenteral administration and achieve high levels of solubility by virtue of their ability to be delivered as readily activated phosphate derivatives. The prodrugs are comprehensively converted to the des-phosphate form in vivo, and the active species have advantageous pharmacokinetic properties and safety pharmacology profiles. The compounds display striking in vivo activity, and compound 5 (AZD1152) has been selected for clinical evaluation and is currently in phase 1 clinical trials.