CAS: 740780-79-4; (R)-Quinuclidin-3-Yl (R)-1-Phenyl-3,4-Dihydroisoquinoline-2(1H)-Carboxylate

该化合物是一种化学化合物,主要用作治疗过活性膀胱的药物,是一种抗氨酸剂,它抑制膀胱肌肉内肌肉受体的乙酰胆碱酯酶作用,从而减少非自愿收缩,增加膀胱受体容量.该化合物的特征是其特定的立体化学学(1R,3R)配置,这对其生物活动至关重要.该化合物通常以其氨酸盐的形式施用,提高其溶解性和生物利用率.该物质以相对较长的半衰期闻名,允许每日一次施用.常见副作用包括干口,凝固和模糊视力,这是抗胆碱药物的典型特征.该化合物的药性皮肤化学学涉及广泛的肝代谢,主要通过细胞化P450酶.

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ethyl (R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (R)-quinuclidin-3-ol (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline 1-phenyl-3,4-dihydroisoquinoline (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate p-toluenesulfonate (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (-)-(2S,3S)-tartrate (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (-)-L-phenylalaninate (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate methanesulfonate

合成工艺路线路线简述

  • 25333-42-0 + 180468-41-1 = 740780-79-4 + 110-15-6 [标题:Reaction Conditions
    标题:Synthesis And Spectral Characterization Of Potential Impurities Of Solifenacin Succinate
    作者:Chavakula,Ramadas; Et Al
    参考文献:Organic Chemistry: An Indian Journal 日期:2014 卷标:10(4) 页码:152-156
📜1-苯基-3,4-二氢异喹啉置于sodium Tetrahydroborate,Sodium Hydride,Potassium Carbonate体系中,用 乙醇,二氯甲烷,甲苯 作为反应溶剂,化学反应 60.0H,反应生成 (1R,3R)-索利那新杂质2
参考文献:Synthesis And Antimuscarinic Properties Of Quinuclidin-3-Yl 1,2,3,4-Tetrahydroisoquinoline-2-Carboxylate Derivatives As Novel Muscarinic Receptor Antagonists
标题:Synthesis And Antimuscarinic Properties Of Quinuclidin-3-Yl 1,2,3,4-Tetrahydroisoquinoline-2-Carboxylate Derivatives As Novel Muscarinic Receptor Antagonists
摘要:In The Course Of Continuing Efforts To Develop Potent And Bladder-Selective Muscarinic M-3 Receptor Antagonists,Quinuclidin-3-Yl 1-Aryl-1,2,3,4-Tetrahydroisoquinoline-2-Carboxylate Derivatives And Related Compounds Were Designed As Conformationally Restricted Analogues Of Quinuclidin-3-Yl Benzhydrylcarbamate (8). Binding Assays With Rat Muscarinic Receptor Subtypes Revealed That The Quinuclidin-3-Yl 1-Aryl-1,2,3,4-Tetrahydroisoquinoline-2-Carboxylate Derivatives Showed High Affinities For The M3 Receptor,And Selectivity For The M3 Receptor Over The M-2 Receptor. Of These Derivatives,(+)-(1S,3'R)-Quinuclidin-3'-Yl 1-Phenyl-1,2,3,4-Tetrahydroisoquinoline-2-Carboxylate Monohydrochloride (9B) Exhibited Almost The Same Inhibitory Activity Against Bladder Contraction To That Of Oxybutynin (1),And More Than 10-Fold Selectivity For Bladder Contraction Versus Salivary Secretion,Demonstrating That 9B May Be Useful For The Treatment Of Symptoms Associated With Overactive Bladder Without Having Side Effects Such As Dry Mouth.
DOI:10.1021/jm050099Q

海关参考信息

专利信息


专利号:US-7741489-B2
优先权日:2007-03-30
标题:Process for the synthesis of solifenacin
发明人:PUIG SERRANO JORDI; CAMPS PELAYO
权利人:MEDICHEM SA
摘要:The present invention provides an improved synthetic strategy for the preparation of solifenacin and pharmaceutically acceptable salts thereof.

专利号:US-2009326230-A1
优先权日:2006-07-19
标题 :Process for preparing solifenacin and its salts
发明人:MATHAD VIJAYAVITTHAL THIPPANNACHAR; LILAKAR JAYDEEPKUMAR DAHYABHAI; GILLA GOVERDHAN; KIKKURU SRIRAMIREDDY; CHINTA RAVEENDRA REDDY; DUDIPALA SWAROOPA
权利人:REDDYS LAB LTD DR; REDDYS LAB INC DR
摘要:The present invention relates to solifenacin in solid form and a process for its preparation and to a process for the preparation of (1S)-1-Phenyl-1,2,3,4-tetrahydro-isoquinoline, a key intermediate in the synthesis of solifenacin and its salts.

专利号:US-2008242697-A1
优先权日:2007-03-30
标题 :Process for the synthesis of solifenacin

专利号:JP-2010523539-A
优先权日:2007-03-30
标 题:Improved synthesis of solifenacin

专利号:CA-2682381-A1
优先权日:2007-03-30
标题:An improved process for the synthesis of solifenacin

专利号:KR-20100016116-A
优先权日:2007-03-30
标 题 :Advanced Synthesis of Solifenacin

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合成参考文献


参考文献:10.1021/jm050099q
摘要:Naito R, Yonetoku Y, Okamoto Y, Toyoshima A, Ikeda K, Takeuchi M. Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists. J Med Chem. 2005 Oct 20;48(21):6597–606. doi: 10.1021/jm050099q.
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