Tariquidar, XR-9576, -Drug Synthesis Database

【结构式】

【药物名称】Tariquidar, XR-9576

【化学名称】N-[2-[N-[4-[2-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]phenyl]carbamoyl]-4,5-dimethoxyphenyl]quinoline-3-carboxamide

【CA登记号】206873-63-4

【分子式】C₃₈H₃₈N₄O₆

【分子量】646.74976

【开发单位】Xenova (Originator), QLT PhotoTherapeutics (Licensee)

【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS, P-Glycoprotein (MDR-1) Inhibitors

合成路线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.

参考文献中间体

【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 .
【1】 Roe, M.; et al.; Reversal of P-glycoprotein mediated multidrug resistance by novel anthranilamide derivatives. Bioorg Med Chem Lett 1999, 9, 4, 595.

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)	31789	4,5-dimethoxy-2-nitrobenzoic acid	4998-07-6	C₉H₉NO₆	详情	详情
(II)	31790	4,5-dimethoxy-2-nitrobenzoyl chloride		C₉H₈ClNO₅	详情	详情
(III)	19194	4-[2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]aniline; 4-[2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]phenylamine		C₁₉H₂₄N₂O₂	详情	详情
(IV)	59595	N-(4-{2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl}phenyl)-4,5-dimethoxy-2-nitrobenzamide		C₂₈H₃₁N₃O₇	详情	详情
(V)	59596	2-amino-N-(4-{2-[6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]ethyl}phenyl)-4,5-dimethoxybenzamide		C₂₈H₃₃N₃O₅	详情	详情
(VI)	59597	3-Quinolinecarboxylic acid; Quinoline-3-carboxylic acid	6480-68-8	C₁₀H₇NO₂	详情	详情
(VII)	59598	3-quinolinecarbonyl chloride		C₁₀H₆ClNO	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)