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              藥物詳細合成路線

              Name Tariquidar;XR-9576
              Chemical Name N-[2-[N-[4-[2-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]phenyl]carbamoyl]-4,5-dimethoxyphenyl]quinoline-3-carboxamide
              CAS 206873-63-4
              Related CAS
              Formula C38H38N4O6
              Structure
              Formula Weight 646.74976
              Stage II 期臨床
              Company Xenova (Originator), QLT PhotoTherapeutics (Licensee)
              Activity/Mechanism Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS, P-Glycoprotein (MDR-1) Inhibitors
              Syn. Route 1
              Route 1
              4,5-dimethoxy-2-nitrobenzoic acid (i) was converted to the corresponding acid chloride (ii) upon treatment with socl2, and this was further coupled to aniline (iii), producing amide (iv). catalytic hydrogenation of the nitro group of (iv) afforded amine (v). acid chloride (vii) --obtained by chlorination of 3-quinolinecarboxylic acid (vi) with socl2-- was then condensed with amine (v) to furnish the title diamide.
              List of intermediates No.
              o-ethyl s-(2-oxobutyl) carbonodithioate (iii)
              (3ar,7as)-7a-methyl-1-[(1r,3e)-6,6,6-trifluoro-5-hydroxy-1-methyl-5-(trifluoromethyl)-3-hexenyl]-3,3a,5,6,7,7a-hexahydro-4h-inden-4-one (i)
              (1r,5r)-3-[2-((3as,7as)-7a-methyl-1-[(1r,3e)-6,6,6-trifluoro-1-methyl-5-(trifluoromethyl)-5-[(trimethylsilyl)oxy]-3-hexenyl]-3,3a,5,6,7,7a-hexahydro-4h-inden-4-ylidene)ethylidene]-5-[[tert-butyl(dimethyl)silyl]oxy]cyclohexyl tert-butyl(dimethyl)sily; [((1r,5r)-3-[2-((3as,7as)-7a-methyl-1-[(1r,3e)-6,6,6-trifluoro-1-methyl-5-(trifluoromethyl)-5-[(trimethylsilyl)oxy]-3-hexenyl]-3,3a,5,6,7,7a-hexahydro-4h-inden-4-ylidene)ethylidene]-5-[[tert-butyl(dimethyl)silyl]oxy]cyclohexyl)oxy](tert-butyl)dimeth (ii)
              Reference 2:
                  ryder, h.; ashworth, p.a.; roe, m.j.; brumwell, j.e.; hunjan, s.; folkes, a.j.; sanderson, j.t.; williams, s.; maximen, l.m. (xenova group plc); anthranilic acid derivs. as multi drug resistance modulators. ep 0934276; gb 2334521; jp 2001502683; us 6218393; wo 9817648 .
              Reference 1:
                  roe, m.; et al.; reversal of p-glycoprotein mediated multidrug resistance by novel anthranilamide derivatives. bioorg med chem lett 1999, 9, 4, 595.

              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Tariquidar;英文名Tariquidar;XR-9576;CAS[206873-63-4]

               
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