利奥西呱合成路线图解
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摘要
<正>利奥西呱(riociguat,1),化学名N-[4,6-二氨基-2-[1-[(2-氟苯基)甲基]-1H-吡唑并[3,4-b]吡啶-3-基]-5-嘧啶基]-N-甲胺基甲酸甲酯,是拜耳公司研发的可溶性鸟苷酸环化酶(soluble guanylate cyclase,s GC)激活剂,2013年10月由FDA批准上市,商品名Adempas,适应证包括慢性血栓栓塞
引文
[1]US Food and Drug Administration.FDA approves Adempas to treat pulmonary hypertension.Press release.Oct.8,2013.http://www.fda.gov/newsevents/newsroom/pressannouncements/ucm370866.htm
[2]Ghofrani HA,GalièN,Grimminger F,et al.Riociguat for the treatment of pulmonary arterial hypertension[J].New Engl J Med,2013,369(4):330—340.
[3]Mittendorf J,Weigand S,Alonso-Alija C,et al.Discovery of riociguat(BAY 63-2521):a potent,oral stimulator of soluble guanylate cyclase for the treatment of pulmonary hypertension[J].Chem Med Chem,2009,9(5):853—865.
[4]李亮,李行舟,刘雅丹,等.肺动脉高压治疗药riociguat的合成[J].中国药物化学杂志,2011,21(2):120—125.
[5]王宏博,邓乾亚,袁博.利奥西呱的合成[J].中国医药工业杂志,2016,47(6):675—678.
[6]Branum ST,Colburn RW,Dax SL,et al.Sulfonamides as TRPM8 modulators:WO,2009012430[P].2009-01-22.
[7]Schirok H,Griebenow N,Fürstner C,et al.Use of3-(trifluoromethyl)-1H-pyrazolo-[3,4-b]pyridine as a versatile building block[J].Tetrahedron,2015,71(49):5597—5601.
[8]Li J,Yang X,Zhu J,et al.Method for synthesizing1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-formamidine hydrochloride:WO,2013086935[P].2013-06-20.
[9]Teixeira FC,Lucas C,Curto MJM,et al.New 1-hydroxy-1,1-bisphosphonates derived from 1H-pyrazolo[3,4-b]pyridine:synthesis and characterization[J].J Brazil Chem Soc,2013,24(8):1295—1306.
[10]Huang S,Lin R,Yu Y,et al.Synthesis of 3-(1Hbenzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1,2-b]-pyridine,a potent cyclin dependent kinase 1(CDK1)inhibitor[J].Bioorg Med Chem Lett,2007,17(5):1243—1245.
[11]Arava V,Gogireddy SR.An expeditious synthesis of riociguat,a pulmonary hypertension drug[J].Der Pharma Chemica,2013,5(4):232—239.
[12]毛影,毕天昊,李锦华,等.一种利奥西呱的制备方法:中国,105294686[P].2016-02-03.
[13]葛德培,吴其华,刘涛.一种利奥西呱的合成方法:中国,104530044[P].2015-04-22.
[14]黄悦,张涛.一种化合物及其在制备利奥西呱中的应用:中国,105367567[P].2016-03-02.
[15]申屠晓波,黄悦.一种制备利奥西呱的方法:中国,105367568[P].2016-03-02.
[16]黄悦,张涛.一种化合物及其作为利奥西呱中间体的应用:中国,105367569[P].2016-03-02.
[17]Ferris JP,Orgel LE.The reactions of bromomalononitrile with bases[J].J Org Chem,1965,30(7):2365—2367.
[18]许学农.利奥西呱中间体及其制备方法:中国,104892459[P].2015-09-09.
[2]Ghofrani HA,GalièN,Grimminger F,et al.Riociguat for the treatment of pulmonary arterial hypertension[J].New Engl J Med,2013,369(4):330—340.
[3]Mittendorf J,Weigand S,Alonso-Alija C,et al.Discovery of riociguat(BAY 63-2521):a potent,oral stimulator of soluble guanylate cyclase for the treatment of pulmonary hypertension[J].Chem Med Chem,2009,9(5):853—865.
[4]李亮,李行舟,刘雅丹,等.肺动脉高压治疗药riociguat的合成[J].中国药物化学杂志,2011,21(2):120—125.
[5]王宏博,邓乾亚,袁博.利奥西呱的合成[J].中国医药工业杂志,2016,47(6):675—678.
[6]Branum ST,Colburn RW,Dax SL,et al.Sulfonamides as TRPM8 modulators:WO,2009012430[P].2009-01-22.
[7]Schirok H,Griebenow N,Fürstner C,et al.Use of3-(trifluoromethyl)-1H-pyrazolo-[3,4-b]pyridine as a versatile building block[J].Tetrahedron,2015,71(49):5597—5601.
[8]Li J,Yang X,Zhu J,et al.Method for synthesizing1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-formamidine hydrochloride:WO,2013086935[P].2013-06-20.
[9]Teixeira FC,Lucas C,Curto MJM,et al.New 1-hydroxy-1,1-bisphosphonates derived from 1H-pyrazolo[3,4-b]pyridine:synthesis and characterization[J].J Brazil Chem Soc,2013,24(8):1295—1306.
[10]Huang S,Lin R,Yu Y,et al.Synthesis of 3-(1Hbenzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1,2-b]-pyridine,a potent cyclin dependent kinase 1(CDK1)inhibitor[J].Bioorg Med Chem Lett,2007,17(5):1243—1245.
[11]Arava V,Gogireddy SR.An expeditious synthesis of riociguat,a pulmonary hypertension drug[J].Der Pharma Chemica,2013,5(4):232—239.
[12]毛影,毕天昊,李锦华,等.一种利奥西呱的制备方法:中国,105294686[P].2016-02-03.
[13]葛德培,吴其华,刘涛.一种利奥西呱的合成方法:中国,104530044[P].2015-04-22.
[14]黄悦,张涛.一种化合物及其在制备利奥西呱中的应用:中国,105367567[P].2016-03-02.
[15]申屠晓波,黄悦.一种制备利奥西呱的方法:中国,105367568[P].2016-03-02.
[16]黄悦,张涛.一种化合物及其作为利奥西呱中间体的应用:中国,105367569[P].2016-03-02.
[17]Ferris JP,Orgel LE.The reactions of bromomalononitrile with bases[J].J Org Chem,1965,30(7):2365—2367.
[18]许学农.利奥西呱中间体及其制备方法:中国,104892459[P].2015-09-09.