合成工艺路线路线简述 2648610-92-6 = 862189-95-5 反应条件:1.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] = 862189-95-5 反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 2 H,20 °C1.2 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C2.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C2.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C2.3 Solvents: Methanol; 2 H,65 °C2.4 Reagents: Sodium Ethoxide; 5 H,65 °C2.5 Solvents: Water; 2 H,65 °C2.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C3.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C3.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] 103-76-4 + 18167-33-4 = 862189-95-5 反应条件:1.1 Reagents: Thionyl Chloride,Chlorosulfonic Acid Solvents: Dimethylformamide; 0 °C; 5 - 10 °C; 25 °C; 4 H,25 °C1.2 Reagents: Triethylamine Solvents: Ethyl Acetate; 0 °C; 0.5 H,0 °C2.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 2 H,20 °C2.2 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C3.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C3.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C3.3 Solvents: Methanol; 2 H,65 °C3.4 Reagents: Sodium Ethoxide; 5 H,65 °C3.5 Solvents: Water; 2 H,65 °C3.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C4.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C4.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] 119-36-8 = 862189-95-5 反应条件:1.1 Reagents: Potassium Carbonate Catalysts: Sodium Iodide Solvents: Acetonitrile; 24 H,Reflux2.1 Reagents: Thionyl Chloride,Chlorosulfonic Acid Solvents: Dimethylformamide; 0 °C; 5 - 10 °C; 25 °C; 4 H,25 °C2.2 Reagents: Triethylamine Solvents: Ethyl Acetate; 0 °C; 0.5 H,0 °C3.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 2 H,20 °C3.2 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C4.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C4.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C4.3 Solvents: Methanol; 2 H,65 °C4.4 Reagents: Sodium Ethoxide; 5 H,65 °C4.5 Solvents: Water; 2 H,65 °C4.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C5.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C5.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] 2648610-93-7 = 862189-95-5 反应条件:1.1 Reagents: Ammonia Solvents: Methanol; Rt -> 40 °C; 1 H,40 °C; 5 H,40 °C2.1 Reagents: Sodium Solvents: Ethanol; 6 H,78 °C2.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 73.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 2 H,20 °C3.2 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C4.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C4.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C4.3 Solvents: Methanol; 2 H,65 °C4.4 Reagents: Sodium Ethoxide; 5 H,65 °C4.5 Solvents: Water; 2 H,65 °C4.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C5.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C5.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] 56-40-6 = 862189-95-5 反应条件:1.1 Reagents: Thionyl Chloride Solvents: Methanol; 0 °C; 0 °C -> 10 °C; 10 °C -> 65 °C; 3 H,65 °C2.1 Reagents: Triethylamine Solvents: Methanol; 1 H,Rt -> Reflux; Reflux -> 0 °C2.2 Reagents: Sodium Borohydride; 1 H,0 °C2.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 1,0 °C3.1 Catalysts: P-Toluenesulfonic Acid Solvents: Toluene; 10 H,112 °C3.2 Reagents: Ammonia Solvents: Methanol; Rt -> 40 °C; 1 H,40 °C; 5 H,40 °C3.3 Reagents: Sodium Solvents: Ethanol; 6 H,78 °C3.4 Reagents: Hydrochloric Acid Solvents: Water; Ph 74.1 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C5.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C5.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C5.3 Solvents: Methanol; 2 H,65 °C5.4 Reagents: Sodium Ethoxide; 5 H,65 °C5.5 Solvents: Water; 2 H,65 °C5.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C6.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C6.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] = 862189-95-5 反应条件:1.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C1.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C1.3 Solvents: Methanol; 2 H,65 °C1.4 Reagents: Sodium Ethoxide; 5 H,65 °C1.5 Solvents: Water; 2 H,65 °C1.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C2.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C2.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] = 862189-95-5 反应条件:1.1 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C2.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C2.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C2.3 Solvents: Methanol; 2 H,65 °C2.4 Reagents: Sodium Ethoxide; 5 H,65 °C2.5 Solvents: Water; 2 H,65 °C2.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C3.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C3.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] = 862189-95-5 反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 2 H,20 °C2.1 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C3.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C3.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C3.3 Solvents: Methanol; 2 H,65 °C3.4 Reagents: Sodium Ethoxide; 5 H,65 °C3.5 Solvents: Water; 2 H,65 °C3.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C4.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C4.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] 2648610-94-8 = 862189-95-5 反应条件:1.1 Reagents: Sodium Solvents: Ethanol; 6 H,78 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 72.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 2 H,20 °C2.2 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C3.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C3.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C3.3 Solvents: Methanol; 2 H,65 °C3.4 Reagents: Sodium Ethoxide; 5 H,65 °C3.5 Solvents: Water; 2 H,65 °C3.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C4.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C4.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] 63744-92-3 + 53386-64-4 = 862189-95-5 反应条件:1.1 Catalysts: P-Toluenesulfonic Acid Solvents: Toluene; 10 H,112 °C1.2 Reagents: Ammonia Solvents: Methanol; Rt -> 40 °C; 1 H,40 °C; 5 H,40 °C1.3 Reagents: Sodium Solvents: Ethanol; 6 H,78 °C1.4 Reagents: Hydrochloric Acid Solvents: Water; Ph 72.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 2 H,20 °C2.2 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C3.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C3.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C3.3 Solvents: Methanol; 2 H,65 °C3.4 Reagents: Sodium Ethoxide; 5 H,65 °C3.5 Solvents: Water; 2 H,65 °C3.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C4.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C4.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] 5680-79-5 + 100-52-7 = 862189-95-5 反应条件:1.1 Reagents: Triethylamine Solvents: Methanol; 1 H,Rt -> Reflux; Reflux -> 0 °C1.2 Reagents: Sodium Borohydride; 1 H,0 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 1,0 °C2.1 Catalysts: P-Toluenesulfonic Acid Solvents: Toluene; 10 H,112 °C2.2 Reagents: Ammonia Solvents: Methanol; Rt -> 40 °C; 1 H,40 °C; 5 H,40 °C2.3 Reagents: Sodium Solvents: Ethanol; 6 H,78 °C2.4 Reagents: Hydrochloric Acid Solvents: Water; Ph 73.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 2 H,20 °C3.2 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C4.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C4.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C4.3 Solvents: Methanol; 2 H,65 °C4.4 Reagents: Sodium Ethoxide; 5 H,65 °C4.5 Solvents: Water; 2 H,65 °C4.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C5.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C5.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39] 109-94-4 = 862189-95-5 反应条件:1.1 Reagents: Sodium Solvents: Ethanol; 24 H,35 °C1.2 Reagents: Hydrochloric Acid Solvents: Ethanol,Water; Ph 7,Cooled2.1 Catalysts: P-Toluenesulfonic Acid Solvents: Toluene; 10 H,112 °C2.2 Reagents: Ammonia Solvents: Methanol; Rt -> 40 °C; 1 H,40 °C; 5 H,40 °C2.3 Reagents: Sodium Solvents: Ethanol; 6 H,78 °C2.4 Reagents: Hydrochloric Acid Solvents: Water; Ph 73.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water; 2 H,20 °C3.2 Reagents: 1-Hydroxybenzotriazole,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dimethylformamide; 14 H,25 °C4.1 Reagents: Acetic Anhydride Solvents: Ethyl Acetate; 25 °C; 1 H,25 °C4.2 Reagents: Ethyl Chloroformate Solvents: Tetrahydrofuran; 2 H,65 °C4.3 Solvents: Methanol; 2 H,65 °C4.4 Reagents: Sodium Ethoxide; 5 H,65 °C4.5 Solvents: Water; 2 H,65 °C4.6 Reagents: Hydrochloric Acid Solvents: Water; Ph 7,65 °C5.1 Reagents: Sodium Solvents: Ethanol; 20 H,78 °C5.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 7 标题:Improved Synthesis Of Mirodenafil 作者:Sun,Zhao-Zhu; Et Al 参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2015 卷标:25(1) 页码:35-39 海关参考信息 2905121000-正丙醇 2921211000-乙二胺 2922110001-单乙醇胺 2922192100-二甲氨基乙醇 💡 提示:海关信息按照顺序优先匹配,如需确认的海关信息,请参考相关资料。 详情请参考: 📖 海关编码查询和海关进出口税则
专利信息 专利号:WO-2022244943-A1 优先权日:2021-05-21 标题 :Method for predicting recurrence of lung cancer, and pharmaceutical composition for recurrence inhibition 发明人:LEE HO-YOUNG 权利人:SEOUL NAT UNIV R&DB FOUNDATION 摘要:The present invention relates to: a method for providing information necessary in predicting the recurrence of lung cancer; a pharmaceutical composition for inhibiting the recurrence of lung cancer; and the like. Since the present inventors have identified that in slow-cycling cancer cells responsible for lung cancer recurrence, RGS2 is significantly increased and ATF4 is reduced, it is expected that by measuring the level of expression or activity of RGS2 and ATF4, the likelihood of lung cancer recurrence can be easily and quickly predicted. In addition, since the present inventors have identified that the growth of slow-cycling cancer cells can be inhibited and the apoptosis thereof can be induced by eliminating the expression of RGS2 or blocking the protein synthesis inhibitory action of RGS2, the present invention is expected to be also variously usable in the drug development of lung cancer recurrence inhibiting therapeutic agents for inhibiting the expression or activity of RGS2. 专利号:WO-2012172449-A1 优先权日:2011-06-13 标题:Lactams as beta secretase inhibitors 发明人:BRODNEY MICHAEL AARON 权利人:PFIZER; BRODNEY MICHAEL AARON 摘要:Compound and pharmaceutically acceptable salts of the compound are disclosed, wherein the compound has the structure (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed. The compound of formula I is useful as beta secretase inhibitor for use in the treatment of Alzheimer's and other neurodegenerative and/or neurological disorders.全部 工厂 研发
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主要参考文献 1: Cho MC, Paick JS. A review of the efficacy and safety of mirodenafil in the management of erectile dysfunction. Ther Adv Urol. 2016 Apr;8(2):100-17. doi: 10.1177/1756287215625408. Epub 2016 Jan 19. Review. 2: Shim JS, Bae JH. Drug Concentration in Rat Plasma, Bladder, and Prostate After Mirodenafil Administration in a Chronic Pelvic Ischemia Model. Urology. 2016 May;91:244.e1-5. doi: 10.1016/j.urology.2016.02.017. Epub 2016 Feb 23. doi: 10.1517/14740338.2016.1131818. Epub 2016 Jan 9. Review. doi: 10.5213/inj.2015.19.1.19. Epub 2015 Mar 26. 5: Peak TC, Yafi FA, Sangkum P, Hellstrom WJ. Emerging drugs for the treatment of erectile dysfunction. Expert Opin Emerg Drugs. 2015 Jun;20(2):263-75. doi: 10.1517/14728214.2015.1021682. Epub 2015 Mar 5. Review. doi: 10.5534/wjmh.2014.32.3.145. Epub 2014 Dec 29.
合成参考文献 摘要:Leonardi R, Alemanni M. The management of erectile dysfunction: innovations and future perspectives. Arch Ital Urol Androl. 2011 Mar;83(1):60–2. 参考文献:10.1016/j.juro.2012.08.276 摘要:Gacci M. Editorial comment. J Urol. 2013 Mar;189(3):1013. doi: 10.1016/j.juro.2012.08.276. 参考文献:10.5534/wjmh.2014.32.1.18 摘要:Park HJ, Moon KH, Lee SW, Lee WK, Kam SC, Lee JH, Park NC. Mirodenafil for the treatment of erectile dysfunction: a systematic review of the literature. World J Mens Health. 2014 Apr;32(1):18–27.