537705-08-1

Basic information

• Product Name: CP-724714
• Synonyms: CP-724714;2-Methoxy-N-[3-[4-[[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]phenyl]amino]-6-quinazolinyl]-2-propen-1-yl]acetamide;(E)-Ethyl (3-(4-((3-Methyl-4-((6-Methylpyridin-3-yl)oxy)phenyl)aMino)quinazolin-6-yl)allyl)carbaMate;acetaMide, 2-Methoxy-N-[3-[4-[[3-Methyl-4-[(6-Methyl-3-pyridinyl)oxy]phenyl]aMino]-6-quinazolinyl]-2-propen-1-yl]-;(E)-Ethyl (3-(4-((3-methyl-4-((6-methylpyridin-3-yl)-oxy)phenyl)amino)quinazolin-6-yl)allyl)carba;(E)-2-Methoxy-N-(3-(4-(3-Methyl-4-(6-Methylpyridin-3-yloxy)phenylaMino)quinazolin-6-yl)allyl)acetaMide;-Ethyl (3-(4-((3-methyl-4-((6-methylpyridin-3-yl);(E)-Ethyl (3-(4-((3-methyl-4-((6-methylpyridin-3-yl)-oxy)phenyl)amino)quinazolin-6-yl)allyl)ca
• CAS NO: 537705-08-1
• Molecular Formula: C27H27N5O3
• Molecular Weight: 469.53498
• EINECS: -0
• Product Categories: Inhibitors
• Mol File: 537705-08-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 687.304 °C at 760 mmHg
• Flash Point: 369.468 °C
• Appearance: /
• Density: 1.251 g/cm³
• Solubility: ≥23.5 mg/mL in DMSO; insoluble in H2O; ≥25.4 mg/mL in EtOH
• CAS DataBase Reference: CP-724714(CAS DataBase Reference)
• NIST Chemistry Reference: CP-724714(537705-08-1)
• EPA Substance Registry System: CP-724714(537705-08-1)

Safety Data

• Hazardous Substances Data: 537705-08-1(Hazardous Substances Data)

Usage

Description

CP-724714 is a potent and selective inhibitor of the HER2/ErbB2 protein, with an IC50 of 10 nM, and also exhibits inhibitory activity against the EGFR protein with an IC50 of 6.4 μM. It is a pharmaceutical compound that has potential applications in various industries due to its ability to target specific proteins involved in cellular processes.

Uses

Used in Pharmaceutical Industry:
CP-724714 is used as a targeted therapy agent for the treatment of cancer. Its high selectivity for HER2/ErbB2 and EGFR proteins makes it a promising candidate for the development of drugs that can specifically inhibit these proteins, which are often overexpressed in various types of cancer cells. This targeted approach can potentially lead to more effective treatments with fewer side effects compared to non-selective chemotherapy drugs.
Used in Cancer Research:
In the field of cancer research, CP-724714 can be used as a valuable tool to study the role of HER2/ErbB2 and EGFR proteins in cancer cell growth and progression. By inhibiting these proteins, researchers can gain insights into the molecular mechanisms underlying cancer development and identify potential therapeutic targets for the development of new cancer treatments.
Used in Drug Development:
CP-724714 can be utilized in the development of new drugs for the treatment of various types of cancer, particularly those that are driven by the overexpression or dysregulation of HER2/ErbB2 and EGFR proteins. Its potent and selective inhibition of these proteins can be leveraged to design drugs that specifically target cancer cells, potentially leading to improved treatment outcomes and reduced side effects for patients.
Used in Drug Delivery Systems:
Similar to gallotannin, CP-724714 can also benefit from the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles can be employed as carriers for CP-724714 delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

Biological Activity

cp-724714 is an inhibitor of erbb2 and egfr kinases with ic50 values of 10±3 nmol/l and 6,400±2,100 nmol/l, respectively [1].in the in vitro cell cycle assay, cp-724714 cause a g1 block of the her2-amplified bt-474 breast cancer cells due to its inhibition of erbb2. cp-724714 at 1 ?mol/l can also reduce the level of phospho-erbb2 in these cells. in in vivo assay, cp-724714 cause a concentration-dependent reduction of tumor erbb2 receptor phosphorylation in athymic mice bearing fre-erbb2xenografts. cp-724714 treatments also resulted in a time- and dose-dependent induction of tumor cell apoptosis. in two human breast carcinoma models, bt-474 and mda-mb-453, which are her2 amplified and highly overexpress erbb2, cp-724714 is found to produce a dose-dependent inhibition of xenograft growth. in addition, cp-724,714 treatments induce reduction of downstream erbb2 rtk signaling. on the basis of these, cp-724,714 was advanced to phase i clinical trials and is potentially another option for her2-driven breast cancer [1].

references

[1] jitesh p. jani, richard s. finn, mary campbell, et al. discovery and pharmacologic characterization of cp-724714, a selective erbb2 tyrosine kinase inhibitor. cancer research. 2007 (67): 9887-9893.

Upstream product

• 38870-89-2 Methoxyacetyl chloride 
• 537705-05-8 6-iodo-N-(3-methyl-4-((6-methylpyridin-3-yl)oxy)phenyl)quinazolin-4-amine 
• 537705-07-0 N-propargyl-2-methoxyacetamide 
• 1121-78-4 5-Hydroxy-2-methylpyridine 
• 13290-74-9 1-chloro-2-methyl-4-nitrobenzene 
• 697299-78-8 2-methyl-5-(2-methyl-4-nitrophenoxy)pyridine 
• 537705-06-9 3-(2-methyl-4-aminophenoxy)-6-methylpyridine 
• 98556-31-1 4-chloro-6-iodoquinazoline 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 16064-08-7 6-iodo-4-hydroxyquinazoline 
• 486393-59-3 N-allyl-2-methoxyacetamide 
• 537705-10-5 (6-iodoquinazolin-4-yl)-[3-methyl-4-(6-methylpyridin-3-yloxy)phenyl]amine hydrochloride 
• 625-45-6 2-methoxyacetic acid 
• 383433-14-5 (3-{4-[3-methyl-4-(6-methylpyridin-3-yloxy)phenylamino]quinazolin-6-yl}prop-2-ynyl)carbamic acid tert-butyl ester 

Relevant articles and documents

Highly functionalised sulfur-based silica scavengers for the efficient removal of palladium species from active pharmaceutical ingredients

The use of multidentate sulfur-based silica scavengers 1,2, and 3 as highly effective adsorbents for the removal of precious metals, specifically palladium residues in this paper, from highly functionalised synthetic intermediates and APIs is described. The synthesis and purification of the polar and electron-rich reaction products, containing multiple functional groups, from palladium-catalysed removals of commonly used protecting groups such as benzyl, benzyloxycarbonyl, and allyloxycarbonyl and Sonogashira, Suzuki, Heck, and Buchwald-Hartwig coupling reactions is reported. The significant levels of residual palladium species, typically associated with these reaction products, are successfully and rapidly removed to below acceptable regulatory levels, of less than 5 ppm, by simple, unoptimised treatment with the designed silica scavengers at room temperature. Performance aspects, including broad solvent compatibility, excellent stability, and high metal affinity, combined with large-scale availability, ease of handling, and minimal loss of API make these silica scavengers particularly useful to process development groups.

Evaluation of kilogram-scale Sonagashira, Suzuki, and Heck coupling routes to oncology candidate CP-724,714

The synthesis of the anti-cancer compound 2-methoxy-N-(3-{4-[3-methyl-4-(6- methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetainide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings to this synthesis was investigated to identify a safe, environmentally friendly, and robust process for the production of this drug candidate. A convergent and selective synthesis of the candidate was identified which utilizes a Heck coupling of a protected allylamine to install the critical olefin.

Selective erbB2 inhibitor/anti-erbB antibody combinations in the treatment of cancer

This invention relates to a method of treatment of cancer with a combination of an erbB2 ligand and an antibody, in mammals. More particularly, this invention relates to a method of treating cancer by administering an erbB2 ligand in combination with an erbB antibody. This invention also relates to a kit useful in the treatment of abnormal cell growth in mammals, especially humans.