Nitrendipine, Bay-e-5009, Baylotensin, Baypress, Bayotensin, -Drug Synthesis Database

【结构式】

【药物名称】Nitrendipine, Bay-e-5009, Baylotensin, Baypress, Bayotensin

【化学名称】(±)-2,6-Dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid ethyl methyl diester

【CA登记号】39562-70-4

【分子式】C₁₈H₂₀N₂O₆

【分子量】360.3699

【开发单位】Bayer (Originator), Almirall Prodesfarma (Licensee), Mitsubishi Pharma (Licensee)

【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Calcium Channel Blockers

合成路线1 合成路线2

合成路线1

1) The condensation of ethyl acetoacetate (I) with 3-nitrobenzaldehyde (II) in toluene gives ethyl 2-(3-nitrobenzylidene)acetoacetate (III), which is then cyclized with methyl 3-aminocrotonate (IV) [prepared from methyl acetoacetate (V) with NH3 and p-toluenesulfonic acid]; the reaction is carried out in refluxing ethanol.

参考文献中间体

【1】 Wehinger, E.; Stoepel, K.; Vater, W.; Meyer, H.; Bossert, F.; Synthesis and comparative pharmacological studies of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylates with non-identical estes function. Arzneim-Forsch Drug Res 1981, 31, 3, 407-409.
【2】 Serradell, M.N.; Castaner, J.; Grau, M.; Blancafort, P.; Nitrendipine. Drugs Fut 1983, 8, 6, 508.

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)	11819	ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate	141-97-9	C₆H₁₀O₃	详情	详情
(II)	12646	3-Nitrobenzaldehyde	99-61-6	C₇H₅NO₃	详情	详情
(III)	30721	ethyl (Z)-2-acetyl-3-(3-nitrophenyl)-2-propenoate		C₁₃H₁₃NO₅	详情	详情
(IV)	11372	Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate		C₅H₉NO₂	详情	详情
(V)	11791	methyl 3-oxobutanoate; Methyl acetoacetate	105-45-3	C₅H₈O₃	详情	详情

合成路线2

2) This compound can also be obtained by direct cyclization of ethyl acetoacetate (I) with 3-nitrobenzaldehyde (II) and 3-aminocrotonate (IV) in refluxing ethanol.

参考文献中间体

【1】 Meyer, H.; Bossert, F. (Bayer AG); Verfahren zur Herstellung con neuen unsymmetrischen 1,4-Dihydropyridindicarbosaureestern. CA 934758; CH 571492; DD 104520; DE 2117573; NL 7204695 .
【2】 Serradell, M.N.; Castaner, J.; Grau, M.; Blancafort, P.; Nitrendipine. Drugs Fut 1983, 8, 6, 508.

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)	11819	ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate	141-97-9	C₆H₁₀O₃	详情	详情
(II)	12646	3-Nitrobenzaldehyde	99-61-6	C₇H₅NO₃	详情	详情
(IV)	11372	Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate		C₅H₉NO₂	详情	详情

Extended Information