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药物详细合成路线

Name Gefitinib;ZD-1839;Iressa
Chemical Name 4-(3-Chloro-4-fluorophenylamino)-7-methoxy-6-[3-(4-morpholinyl)propoxy]quinazoline
CAS 184475-35-2
Related CAS 184475-56-7 (diHCl), 184475-55-6 (mono HCl salt)
Formula C22H24ClFN4O3
Structure
Formula Weight 446.91298
Stage 上市-2002
Company AstraZeneca (Originator), EORTC (Not Determined), M.D. Anderson Cancer Center (Not Determined), National Cancer Institute (Not Determined)
Activity/Mechanism Astrocytoma Therapy, Bladder Cancer Therapy , Brain Cancer Therapy, Breast Cancer Therapy, Colorectal Cancer Therapy, Gastric Cancer Therapy, Glioblastoma MultiformeTherapy, Head and Neck Cancer Therapy, Liver Cancer Therapy, Lung Cancer Therapy, Non-Small Cell Lung Cancer Therapy, Oncolytic Drugs, Ovarian Cancer Therapy, Prostate Cancer Therapy, Solid Tumors Therapy, Squamous Cell Carcinoma Therapy, EGFR (erbB1) Inhibitors, Inhibitors of Signal Transduction Pathways, Tyrphostins
Syn. Route 1
Route 1
monodemethylation of 6,7-dimethoxyquinazolin-4(3h)-one (i) in refluxing methanesulfonic acid in the presence of l-methionine provides 6-hydroxy-7-methoxyquinazolin-4(3h)-one (ii), which is acetylated with acetic anhydride and pyridine at 100 c to give the acetate (iii). treatment of compound (iii) with refluxing socl2 and a catalytic amount of dmf yields chloride (iv), which by condensation with 3-chloro-4-fluoroaniline (v) in boiling isopropanol affords the anilinoquinazoline (vi). hydrolysis of the acetate group of (vi) by treatment with nh4oh in refluxing meoh gives the 6-hydroxyquinazoline derivative (vii), which finally is alkylated with 3-(4-morpholinyl)-propyl chloride (viii) or 3-(4-morpholinyl)propyl bromide (ix).
List of intermediates No.
diethyl (2s)-2-([4-[(3-[[(2,2-dimethylpropanoyl)oxy]methyl]-2-methyl-4-oxo-4,6,7,8-tetrahydro-3h-cyclopenta[g]quinazolin-6-yl)amino]benzoyl]amino)pentanedioate (i)
diethyl (2s)-2-([4-[(3-[[(2,2-dimethylpropanoyl)oxy]methyl]-2-methyl-4-oxo-4,6,7,8-tetrahydro-3h-cyclopenta[g]quinazolin-6-yl)(2-propynyl)amino]benzoyl]amino)pentanedioate (ii)
(2s)-2-([4-[(2-methyl-4-oxo-4,6,7,8-tetrahydro-3h-cyclopenta[g]quinazolin-6-yl)(2-propynyl)amino]benzoyl]amino)pentanedioic acid (iii)
8-(difluoromethoxy)-6,7-difluoro-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (iv)
8-(difluoromethoxy)-1-ethyl-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (v)
1,2,3-trimethoxy-5-methylbenzene; 2,3-dimethoxy-5-methylphenyl methyl ether; 3,4,5-trimethoxytoluene (vi)
ethyl 10-chloro-10-oxodecanoate (vii)
10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)-10-oxodecanoic acid (viii)
Reference 1:
    gibson, k.h.; grundy, w.; barker, a.j.; et al.; studies leading to the identification of zd1839 (iressa(tm)): an orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer. bioorg med chem lett 2001, 11, 14, 1911.
Reference 2:
    dsouza, n.; casta?er, j.; levin, m.; iressa. drugs fut 2002, 27, 4, 339.
Reference 3:
    gibson, k.h. (astrazeneca plc); quinazoline derivs.. ep 0823900; jp 1999504033; us 5770599; wo 9633980 .

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名吉非替尼;英文名Gefitinib;ZD-1839;Iressa;CAS[184475-35-2]

 
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