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【结 构 式】

【药物名称】DD-612

【化学名称】N-[2-(1-Pyrrolidinyl)ethyl]-glycyl-N-cyclopropyl-glycyl-N2-(1-methylpropyl)glycinamide

【CA登记号】

【 分 子 式 】C19H35N5O3

【 分 子 量 】381.5225

【开发单位】DiverDrugs (Originator), Advancell (Licensee)

【药理作用】Cerebrovascular Diseases, Treatment of, Ischemic Stroke, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of

合成路线1

The title compound is prepared by solid phase synthesis employing a Rink amide resin. Acylation of the resin with chloroacetyl chloride (I) affords the chloroacetyl resin (II). Subsequent chloride displacement with s-butylamine (III) provides the aminoacid-bound resin (IV). A new acylation of (IV) with chloroacetyl chloride (I) yields the chloroacetamide (V), which is then displaced by cyclopropylamine (VI), yielding the dipeptide derivative (VII). Then, a further coupling of (VII) with acid chloride (I), followed by displacement of the resultant chloroacetamide resin (VIII) with N-(2-aminoethyl)pyrrolidine (IX) gives rise to the tripeptide resin (X). Finally, cleavage of the dipeptide amide from the solid support is accomplished by treatment with trifluoroacetic acid in CH2Cl2

1 Montoliu, C.; et al.; Prevention of in vivo excitotoxicity by a family of trialkylglycines, a novel class of neuroprotectants. J. Pharm. Exp. Ther. 2002, 301, 1, 29.
2 Felipo Orts, V.; Montoliu Felix, C.; Ferrer Montiel, A.; Planells Cases, R.; Merino Fernandez, J.M.; Perez Paya, E.; Sanchez Baeza, F.; Humet, M.; Messeguer Peypoch, A. (DiverDrugs SL); N-Alkylglycine trimeres capable of protecting neurons against excitotoxic aggressions and compsns. containing said trimeres. WO 0228885 .
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) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(II) 28964 2-chloroacetamide 79-07-2 C2H4ClNO 详情 详情
(III) 61462 sec-butyl amine; 2-Butanamine, (+-)-; 2-Aminobutane; 2-Butylamine; 2-Butanamine; 2-aminobutane base; butafume; deccotane; frucote; Butanamine; Methylpropylamine; SEC-BUTYLAMINE; (+/-)-sec-Butylamine; (+/-)-2-Aminobutane; Sec-Aminobutane; Sec-Butylamine; 2-Aminobutan; (+/-)-2-Butylamine; sec-Butylamine; Butylamine (sec); SBA; METHYL-n-PROPYLAMINE; (+/-)-2-Aminobutane 13952-84-6 C4H11N 详情 详情
(IV) 61463 2-(sec-butylamino)acetamide C6H14N2O 详情 详情
(V) 61464 2-[sec-butyl(2-chloroacetyl)amino]acetamide C8H15ClN2O2 详情 详情
(VI) 12263 Cyclopropylamine; Cyclopropanamine 765-30-0 C3H7N 详情 详情
(VII) 61465 2-{sec-butyl[2-(cyclopropylamino)acetyl]amino}acetamide C11H21N3O2 详情 详情
(VIII) 61466 2-(sec-butyl{2-[(2-chloroacetyl)(cyclopropyl)amino]acetyl}amino)acetamide C13H22ClN3O3 详情 详情
(IX) 18161 2-(1-pyrrolidinyl)ethylamine; 2-(1-pyrrolidinyl)-1-ethanamine; 1-Pyrrolidineethanamine 7154-73-6 C6H14N2 详情 详情
(X) 61467 2-(sec-butyl{2-[cyclopropyl(2-{[2-(1-pyrrolidinyl)ethyl]amino}acetyl)amino]acetyl}amino)acetamide C19H35N5O3 详情 详情
Extended Information