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【结 构 式】 
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【药物名称】 【化学名称】N-[N-[3-(2,3-Diphenylpropionamidomethyl)benzyl]amidino]-N'-[tetrahydrofuran-2(R)-ylmethyl]urea 【CA登记号】 【 分 子 式 】C30H35N5O3 【 分 子 量 】513.64515 |
【开发单位】Alanex (Originator) 【药理作用】Antiobesity Drugs, METABOLIC DRUGS, Treatment of Nutritional Disorders, Neuropeptide Y1 (NPY Y1) Antagonists |
合成路线1
The reaction of m-xylene-alpha,alpha'-diamine (I) with N,N'-bis(tert-butoxycarbonyl)pyrazole-1-carboxamidine (II) in THF gives the protected guanidine (III), which is acylated at the free amino group with 2,3-diphenylpropionyl chloride (IV) and triethylamine in dichloromethane affording the amide (V). The condensation of (V) with tetrahydrofuran-2-ylmethylamine (VI) in refluxing THF affords the protected amidinourea (VII), which is finally treated with TFA in dichloromethane.
| 【1】 Biftu, T.; et al.; Synthesis and SAR of oxodiazole benzenesulfonamides as selective beta3 adrenergic receptor agonist antiobesity agents. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 138. |
| 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) | 19167 | 3-(aminomethyl)benzylamine; [3-(aminomethyl)phenyl]methanamine | 1477-55-0 | C8H12N2 | 详情 | 详情 |
| (II) | 29482 | N,N-bis-Boc-1-guanylpyrazole; tert-butyl (E)-[(tert-butoxycarbonyl)amino](1H-pyrazol-1-yl)methylidenecarbamate | 152120-54-2 | C14H22N4O4 | 详情 | 详情 |
| (III) | 29483 | tert-butyl (Z)-[[3-(aminomethyl)benzyl]amino][(tert-butoxycarbonyl)amino]methylidenecarbamate | C19H30N4O4 | 详情 | 详情 | |
| (IV) | 29484 | 2,3-diphenylpropanoyl chloride | C15H13ClO | 详情 | 详情 | |
| (V) | 29485 | tert-butyl (Z)-[(tert-butoxycarbonyl)amino][(3-[[(2,3-diphenylpropanoyl)amino]methyl]benzyl)amino]methylidenecarbamate | C34H42N4O5 | 详情 | 详情 | |
| (VI) | 27335 | Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine | 4795-29-3 | C5H11NO | 详情 | 详情 |
| (VII) | 29486 | tert-butyl (Z)-[(3-[[(2,3-diphenylpropanoyl)amino]methyl]benzyl)amino]([[(tetrahydro-2-furanylmethyl)amino]carbonyl]amino)methylidenecarbamate | C35H43N5O5 | 详情 | 详情 |