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【结 构 式】 
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【药物名称】GCC-AP0341 【化学名称】5-Amino-3-(4-chlorophenyl)-N-methyl-1,2,4-triazole-1-carbothioamide 【CA登记号】168893-29-6 【 分 子 式 】C10H10ClN5S 【 分 子 量 】267.7417 |
【开发单位】Mitsubishi Pharma (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS |
合成路线1
The reaction of 4-chlorobenzoylhydrazide (I) with S-methyl isothiourea sulfate in aqueous NaOH gave guanidine (II) which, on heating at 220 C, was converted into aminotriazole (III). Subsequent condensation with methyl isothiocyanate in DMF gave thiocarbonyl triazole (IV). Finally, cyclization with diethoxymethyl acetate at 90 C provided the target triazolotriazine.
| 【1】 Akahoshi, F.; et al.; Synthesis and pharmacological activity of triazolo[1,5-a]triazine derivatives inhibiting eosinophilia. J Med Chem 1998, 41, 16, 2985-2993. |
| 【2】 Naito, Y.; et al.; Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia. J Med Chem 1996, 39, 15, 3019-3029. |
| 【3】 Akahoshi, F.; Okada, T.; Takeda, S.; Naito, Y.; Fukaya, C.; Kuwahara, S.; Kajii, M.; Nishimura, H.; Sugiura, M. (Welfide Corporation); Triazole derivs. and pharmaceutical use thereof. EP 0710654; JP 1995082270; JP 1995097321; JP 1995101942; US 5750545; WO 9503286 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10272 | [[Amino(imino)methyl]sulfanyl]methane | 2986-19-8 | C2H6N2S | 详情 | 详情 | |
| (I) | 18216 | 4-chlorobenzohydrazide; p-chloro-benzoylhydrazine | 536-40-3 | C7H7ClN2O | 详情 | 详情 |
| (II) | 18217 | 2-(4-chlorobenzoyl)-1-hydrazinecarboximidamide | C8H9ClN4O | 详情 | 详情 | |
| (III) | 18218 | 5-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamine; 5-(4-chlorophenyl)-1H-1,2,4-triazol-3-amine | C8H7ClN4 | 详情 | 详情 | |
| (IV) | 18219 | 5-amino-3-(4-chlorophenyl)-N-methyl-1H-1,2,4-triazole-1-carbothioamide | C10H10ClN5S | 详情 | 详情 | |
| (V) | 17661 | Diethoxymethyl acetate | 14036-06-7 | C7H14O4 | 详情 | 详情 |
Extended Information