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【结 构 式】 
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【药物名称】BIBO-3304 【化学名称】Nalpha-(2,2-Diphenylacetyl)-D-arginine 4-(ureidomethyl)benzylamide trifluoroacetate 【CA登记号】191868-14-1 【 分 子 式 】C31H36F3N7O5 【 分 子 量 】643.67167 |
【开发单位】Boehringer Ingelheim (Originator) 【药理作用】Angina pectoris, Treatment of, Antiobesity Drugs, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, METABOLIC DRUGS, PHARMACOLOGICAL TOOLS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Treatment of Nutritional Disorders, Neuropeptide Y1 (NPY Y1) Antagonists |
合成路线1
The reaction of Nomega'-nitro-D-arginine (I) with 2,2-diphenylacetyl chloride (II) by means of NaOH in THF/water gives the expected Nalpha-diphenylacetyl derivative (III), which is condensed with 4-(ureidomethyl)benzylamine (IV) by means of TBTU and DIEA in THF to yield the corresponding amide (V). Finally, this compound is hydrogenated with H2 over Pd/C in aqueous acetic acid in order to eliminate the Nomega'-nitro group and treated with trifluoroacetic acid to provide the target compound.
| 【1】 Engel, W.; Eberlein, W.; Rudolf, K.; Doods, H.; Wieland, H.-A.; Willim, K.-D.; Entzeroth, M.; Wienen, W. (Dr. Karl Thomae GmbH); Amino acid derivs., pharmaceutical compsns. containing these cpds. and processes for preparing them. DE 19544687; EP 0885186; WO 9719911 . |
| 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) | 25103 | N-omega'-nitro-D-arginine | C6H13N5O4 | 详情 | 详情 | |
| (II) | 23800 | Diphenylacetyl chloride; 2,2-diphenylacetyl chloride | 1871-76-7 | C14H11ClO | 详情 | 详情 |
| (III) | 25104 | N-alpha-(2,2-diphenylacetyl)-N-omega'-nitro-D-arginine | C20H23N5O5 | 详情 | 详情 | |
| (IV) | 25105 | N-[4-(aminomethyl)benzyl]urea | C9H13N3O | 详情 | 详情 | |
| (V) | 25106 | N-alpha-(2,2-diphenylacetyl)-N-omega'-nitro-N1-[4-(ureidomethyl)benzyl]-D-arginine | C29H34N8O5 | 详情 | 详情 |