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              藥物詳細合成路線

              Name Felodipine;H-154/82;CGH-869;Prevex;Perfudal;Lexxel(Comb. with enalapril);Logimax;Splendil;Munobal;Modip;Flodil;Plendil;Hydac
              Chemical Name (±)-4-(2,3-Dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid ethyl methyl diester;(±)-4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3-ethoxycarbonyl-5-methoxycarbonylpyridine
              CAS 86189-69-7
              Related CAS 72509-76-3 (undefined stereoch.)
              Formula C18H19Cl2NO4
              Structure
              Formula Weight 384.26243
              Stage 上市-1988
              Company Asta Medica (Originator), AstraZeneca (Originator), Aventis Pharma (Originator), Kissei (Licensee), Merck & Co. (Licensee), Novartis (Licensee), Promed (Licensee)
              Activity/Mechanism Angina pectoris, Treatment of, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Calcium Channel Blockers
              Syn. Route 3
              Route 1
              by cyclization of methyl 2,3-dichlorobenzyldeneacetoacetate (i) with ethyl 3-aminocrotonate (ii) in tert-butanol at room temperature.
              List of intermediates No.
              1-([[1-(1-hydroxy-2,2,6,6-tetramethyl-4-piperidinyl)-2-oxohydrazino]carbonyl]oxy)-2,5-pyrrolidinedione (ii)
              (3s,3ar,4s,4as,8ar,9as)-3-methyl-4-[(e)-2-[(2r,6s)-6-methylpiperidinyl]ethenyl]decahydronaphtho[2,3-c]furan-1(3h)-one (i)
              Reference 1:
                  carter, r.e.; berntsson, p.; determination of te conformation of felodipine by 1h nmr-spinlattice relaxation time measurements. acta pharm suec 1981, 18, 221-226.
              Reference 2:
                  bernston, p.b.; carlsson, s.a.i.; gaarder, j.o.; ljung, b.r. (astrazeneca ab); 2,6-dimethyl-4-2,3-disubstituted phenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid-3,5-asymmetric diesters having hypotensive properties, as well as method for treating hypertensive conditions and pharmaceutical preparations containing same. ca 1117530; ep 0007293; jp 55009083; us 4264611 .
              Reference 3:
                  blancafort, p.; serradell, m.n.; sneddon, j.m.; castaner, j.; felodipine. drugs fut 1982, 7, 3, 160.

              Route 2
              by cyclization of 2,3-dichlorobenzaldehyde (i) with 3-aminocrotonic acid ethyl ester (ii) and acetylacetic acid methyl ester (iii) in refluxing ethanol.
              List of intermediates No.
              7-ethynyl-4,4-dimethyl-3,4-dihydro-1(2h)-naphthalenone (iii)
              1-([[1-(1-hydroxy-2,2,6,6-tetramethyl-4-piperidinyl)-2-oxohydrazino]carbonyl]oxy)-2,5-pyrrolidinedione (ii)
              tert-butyl (1s)-1-[[(2,5-dioxo-2,5-dihydro-1h-pyrrol-1-yl)oxy]carbonyl]-2-methylpropylcarbamate (i)
              Reference 1:
                  bernston, p.b.; carlsson, s.a.i.; gaarder, j.o.; ljung, b.r. (astrazeneca ab); 2,6-dimethyl-4-2,3-disubstituted phenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid-3,5-asymmetric diesters having hypotensive properties, as well as method for treating hypertensive conditions and pharmaceutical preparations containing same. ca 1117530; ep 0007293; jp 55009083; us 4264611.

              Route 3
              by cyclization of 2-(2,3-dichlorobenzylidene)acetyl acetic acid methyl ester (iv) with acetylacetic acid ethyl ester (v) and ammonia (vi) in tert-butanol.
              List of intermediates No.
              5-[4-hydroxy-2-(3-hydroxypentyl)-3,5,6-trimethylphenoxy]-2,2-dimethylpentanoic acid (v)
              (3s,3ar,4s,4as,8ar,9as)-3-methyl-4-[(e)-2-[(2r,6s)-6-methylpiperidinyl]ethenyl]decahydronaphtho[2,3-c]furan-1(3h)-one (iv)
              Reference 1:
                  bernston, p.b.; carlsson, s.a.i.; gaarder, j.o.; ljung, b.r. (astrazeneca ab); 2,6-dimethyl-4-2,3-disubstituted phenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid-3,5-asymmetric diesters having hypotensive properties, as well as method for treating hypertensive conditions and pharmaceutical preparations containing same. ca 1117530; ep 0007293; jp 55009083; us 4264611.

              來源:藥化網

              作者:藥化小編

              摘要:本文合成路線介紹的是藥物中文名非洛地平;英文名Felodipine;H-154/82;CGH-869;Prevex;Perfudal;Lexxel(Comb. with enalapril);Logimax;Splendil;Munobal;Modip;Flodil;Plendil;Hydac;CAS[86189-69-7]

               
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