富马酸喹硫平的合成研究进展
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摘要
富马酸喹硫平是一种非典型抗精神病药,临床作为精神分裂症的一线治疗药物。本文综述了富马酸喹硫平自1987年发现至今的合成研究进展。
Quetiapine hemifumarate is an atypical antipsychotic drug and clinically used as the first-line drug for the treatment of schizophrenia. This paper has reviewed the synthetic progress of quetiapine hemifumarate since it was discovered in 1987.
Quetiapine hemifumarate is an atypical antipsychotic drug and clinically used as the first-line drug for the treatment of schizophrenia. This paper has reviewed the synthetic progress of quetiapine hemifumarate since it was discovered in 1987.
引文
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[7]梁伟周,刘涛,陈延蕾,等.半富马酸喹硫平的合成研究[J].中国医药工业杂志,2004,35(12):705—707.
[8]胡金星,张凯,刘海城,等.半富马酸喹硫平的合成工艺研究[J].中国药物化学杂志,2015,(3):194—198.
[9]吕雪皓,陶明,李桂芹,等.2-氨基二苯硫醚的制备方法:中国,102603584[P].2012-07-25.
[10]Wang C,Ma Z,Sun XL,et al.Synthesis and characterization of titanium(Ⅳ)complexes bearing monoanionic[O-NX](X=O,S,Se)tridentate ligands and their behaviors in ethylene homo-and copolymerizaton with 1-hexene[J].Organometallics,2006,25(13):3259—3266.
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[12]Gogoi P,Hazarika S,Sarma MJ,et al.Nickel-Schiff base complex catalyzed C-S cross-coupling of thiols with organic chlorides[J].Tetrahedron,2015,46(10):7484—7489.
[13]Salam N,Kundu SK,Roy AS,et al.Cu-grafted mesoporous organic polymer:a new recyclable nanocatalyst for multicomponent,N-arylation and S-arylation reactions[J].Catal Sci Technol,2013,3(12):3303—3316.
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[16]Kao HL,Chen CK,Wang YJ,et al.An efficient coppercatalyzed cross-coupling reaction of thiols with aryl iodides[J].Eur J Org Chem,2011,(9):1776—1781.
[17]Feng Y,Wang H,Sun F,et al.A highly efficient and widely functional-group-tolerant catalyst system for copper(I)-catalyzed S-arylation of thiols with aryl halides[J].Tetrahedron,2009,65(47):9737—9741.
[18]Kwak BS,Lee SI,Hwang HJ,et al.Process for the preparation of 11-[4-[2-(2-hydroxyethoxyethyl)-1-piperazinyl]dibenzo[b,f][1,4]thiazepine:WO,2006001619[P].2006-01-05.
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[20]畅水平.一种半富马酸喹硫平的制备方法:中国,104016945[P].2014-09-03.
[21]Kandula VR,Fondekar KP.An efficient one pot synthesis of dibenzo[b,f][1,4]thiazepin-11[10H]-one:A key intermediate for synthesis of quetiapine an antipsychotic drug[J].Org Chem Indian J,2015,11(6):211—214.
[22]谭云,邵江勇,赵敏,等.喹硫平的合成改进研究[J].中国新药杂志,2007,16(11):867—868.
[23]Wadsworth H,Jones PA,Chau WF,et al.Exploration of the structure-activity relationship of the diaryl anilide class of ligands for translocator protein-potential novel positron emitting tomography imaging agents[J].Bioorg Med Chem Lett,2012,22(18):5795—5800.
[24]Xiang J,Zhang Z,Mu Y,et al.Discovery of novel tricyclic thiazepine derivatives as anti-drug-resistant cancer agents by combining diversity-oriented synthesis and converging screening approach[J].Acs Comb Sci,2016,18(5):230—235.
[25]Bardin VV,Adonin NY.Reactions of aromatic compounds with xenon difluoride[J].Russ J Org Chem,2016,52(10):1400—1407.
[26]Chatterjee N,Bhatt D,Goswami A.A novel transition metal free,[bis-(trifluoroacetoxy)iodo]benzene(PIFA)mediated oxidative ipso nitration of organoboronic acids[J].Org Biomol Chem,2015,13(17):4828—4832.
[27]Dhingra SK,Nag P,Saxena R.Highly efficient and greener approach for fluorinating organic compounds[J].Chem Sci Trans,2015,4(4):1176—1180.
[28]王士玉.硝基苯氯化物的分离及综合利用方法:中国,101613286[P].2009-12-30.
[29]郭振伟,刘文波.邻氟硝基苯的生产工艺:中国,101838203[P].2010-09-22.
[30]邹新琢,赵玉林,程浩.一种芳香族氟化物的制备方法:中国,104370671[P].2015-02-25.
[31]罗军,蔡春,吕春绪.微波促进聚乙二醇催化卤素交换氟化反应[J].精细化工,2002,19(10):593—595.
[32]Grumann A,Muceniece D,Soidinsalo O.Process for the preparation of quetiapine:WO,2009095529[P].2009-08-06.
[33]李文军,陶长戈,彭超,等.一种硫氮杂?类化合物的合成方法:中国,103772319[P].2014-05-07.
[34]姚金忠,周宏伟,陈佃鹏.一种喹硫平的合成方法:中国,105859653[P].2016-04-29.
[35]Gootles J,Funcke AB,Tersteege HM,et al.The effect of alkylsub stitution indrugs.XVII.Synthes is and pharmacological porperties of alkyl-substituted benzhydryl derivatives of piperazine[J].Arzneimittelforschung,1966,16(11):1557—1560.
[36]Henri M.Piperzaine derivatives:US,2988551[P].1961-06-13.
[37]陶伟锋,童小兵,季海杰,等.一种高纯度1-[2-(2-羟乙氧基)乙基]哌嗪的制备方法:中国,103254153[P].2013-08-21.
[38]郑国友.二乙醇胺法制备1-[2-(2-羟基乙氧基)乙基]-哌嗪新工艺:中国,103224476A[P].2013-07-31.
[39]Bou Chedid R,Melder J,Abel U,et al.Process for the preparation of a mono-N-alkylpiperazine:US,20130324732[P].2013-12-05.
[40]Warawa EJ,Migler BM.Thiazepine compounds:EP,0240228[P].1987-10-07.
[41]Barker AC,Copeland RJ.Process for the preparation of a thiazepine compound:EP,0282236[P].1988-09-14.
[42]Czibula L,Dobay L,Feher K,et al.Synthesis for the preparation of quetiapine:WO,2008152434[P].2008-12-18.
[43]Niphade NC,Mali AC,Pandit BS,et al.An improved and single pot process for the production of quetiapine hemifumarate substantially free from potential impurities[J].Org Process Res Dev,2009,13(4):792—797.
[44]Gant TG,Sarshar S.Preparation of dibenzothiazepine as modulators of dopamine,alpha adrenergic,and serotonin receptors for treatment of disorders:US,20100069356[P].2010-03-18.
[45]邓莉平,陶伟锋,吕建国,等.一种富马酸喹硫平的制备工艺:中国,101619047[P].2010-01-06.
[46]翁意意,苏为科,童小兵,等.一种Vilsmeier试剂参与的11-氯二苯并[b,f][1,4]硫氮杂?的制备方法:中国,103804320[P].2014-05-21.
[47]Mahmoodi NO,Pourhossein Parizad M,Hosseini K.Pyrophosphoryl chloride:A green,reductive chlorination reagent utilized in the one-pot synthesis of quetiapine[J].Phosphorus,Sulfur Silicon Relat Elem,2015,190(7):1029—1034.
[48]蚩晓娜,谷志勇,吕亚军,等.一种结晶性二苯并硫氮杂?衍生物的制备方法:中国,105085435[P].2015-11-25.
[49]Ponnaiah R,Prasad A,Panchasara DR,et al.A process for preparing quetiapine fumarate:WO,2010070510[P].2010-06-24.
[50]吴南林,唐焕宇.制备药物纯富马酸喹硫平的生产方法:中国,101190902[P].2008-06-04.
[51]Malik GM,Tailora JH,Zadafiyaa SK,et al.Synthesis and biological activity of triazolo derivative of dibenzothiazepine[J].Brit J Exp Pathol,2015,8(2):106—109.
[52]Kandula M.Compositions and methods for the treatment of neurological diseases and its associated complications:WO,2014057439[P].2014-04-17.
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