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【结 构 式】 
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【药物名称】Trimetrexate glucuronate, NSC-352122, NeuTrexin 【化学名称】2,4-Diamino-6-(3,4,5-trimethoxyphenylaminomethyl)-5-methylquinazoline mono-D-glucuronic acid salt 【CA登记号】82952-64-5 【 分 子 式 】C25H33N5O10 【 分 子 量 】563.56926 |
【开发单位】Pfizer (Originator), Ipsen (Licensee), Lilly (Licensee), MedImmune Oncology (Licensee) 【药理作用】ANTIINFECTIVE THERAPY, Colorectal Cancer Therapy, Gastric Cancer Therapy, Oncolytic Drugs, Pneumocystis carinii Pneumonia, Agents for, Prostate Cancer Therapy, Treatment of Protozoal Diseases, Dihydrofolate Reductase (DHFR) Inhibitors |
合成路线1
The reaction of 2,4,6-triamino-5-methylquinazoline (I) with NaNO2 and aqueous HCl gives the corresponding diazonium salt (II), which by a Sandmeyer reaction with cuprous cyanide in hot water yields 2,4-diamino-5-methylquinazoline-6-carbonitrile (III). Finally, this compound is reductocondensed with 3,4,5-trimethoxyaniline (IV) by means of H2 over Raney-Ni in acetic acid.
| 【1】 Elslager, E.F.; Werbel, L.M. (Pfizer Inc.); Quinazoline compounds and processes for their production. GB 1345502 . |
| 【2】 Hillier, K.; Castañer, J.; Serradell, M.N.; Blancafort, P.; JB-11. Drugs Fut 1981, 6, 5, 282. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 32222 | 2,4-diamino-5-methyl-6-quinazolinylamine; 5-methyl-2,4,6-quinazolinetriamine | C9H11N5 | 详情 | 详情 | |
| (II) | 32223 | 2,4-diamino-5-methyl-6-quinazolinediazonium chloride | C9H9ClN6 | 详情 | 详情 | |
| (III) | 32224 | 2,4-diamino-5-methyl-6-quinazolinecarbonitrile | C10H9N5 | 详情 | 详情 | |
| (IV) | 31545 | 3,4,5-trimethoxyaniline; 3,4,5-trimethoxyphenylamine；3,4,5-Trimethoxybenzenamine；[3,4,5-Tris(methyloxy)phenyl]amine | 24313-88-0 | C9H13NO3 | 详情 | 详情 |