依匹哌唑的合成研究进展
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摘要
综述了依匹哌唑的合成方法,详细阐述并比较了依匹哌唑中间体4-(1-哌嗪)苯并[b]噻吩的合成工艺。并对依匹哌唑合成方法的发展进行了展望。
The synthetic progress of Brexpiprazole was briefly reviewed,and the divergent methods for the preparation of its key intermediate 1-( benzo[b]thiophen-4-yl) piperazine were described and compared in detail. The future development of Brexpiprazole was prospected as well.
The synthetic progress of Brexpiprazole was briefly reviewed,and the divergent methods for the preparation of its key intermediate 1-( benzo[b]thiophen-4-yl) piperazine were described and compared in detail. The future development of Brexpiprazole was prospected as well.
引文
[1]徐磊,封宇飞.5-羟色胺-多巴胺受体部分激动剂依匹哌唑的药理作用与临床评价[J].中国新药杂志,2016,25(5):481-483.
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[17]TILSTAM U.A continuous protodecarboxylation of heteroaromatic carboxylic acids in sulfolane[J].Org Process Res Dev,2012,16(8):1149-1454.
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[22]LIU K,JIA F,XI H,et al.Direct benzothiophene formation via oxygen-triggered intermolecular cyclization of thiophenols and alkynes assisted by manganese/Ph CO2H[J].Org Lett,2013,15(14):2026-2029.
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[24]WANG G,BEIGILMAN L,TRUONG A,et al.Compounds for the treatment of paramoxyvirus viral infections:WO 2014031784[P].2014.
[25]LI C Y,SU C,WANG H H,et al.Design and development of cyclometalated ruthenium complexes containing thiophenyl-pyridne ligand for dye-sensitized solar cells[J].Dyes Pigm,2014,100(1):57-65.
[26]NICULESU D D,NICULESCU D Z I,SUILKERBUIJK B M J M,et al.Potent BRAF kinase inhibitors based on 2,4,5-trisubstituted imidazole with naphthyl and benzothiophene 4-substituents[J].Bioorg Med Chem,2013,21(8):1284-1304.
[27]张健,田广辉.布瑞哌唑类似物的制备方法:CN201510061026[P].2015.
[28]WU C H,CHEN W M,JIANG D H,et al.An improved synthesis of 4-(1-piperazinyl)benzo[b]thiophene dihydrochloride[J].Org Process Res Dev,2015,19(3):555-558.
[29]MATUSNAGA N,KAKUT,ITOH F,et al.C17,20-lyase inhibitors I.Structure-based de novo design and SAR study of C17,20-lyase inhibitors[J].Bioorg Med Chem,2004,12(8):2251-2273.
[30]Yi IN H,CHENG K.Modulators of TLR3/DSRNA complex and uses thereof:WO 2012099785[P].2012.
[31]CHENG K,WANG X H,YIN H.Small-molecule inhibitors of the TLR3/DSRNA complex[J].J Am Chem Soc,2011,133(13):3764-3767.
[32]彭锦安,周革文.一种Brexpiprazole的制备方法:CN 201410853528[P].2014.
[33]赵爱明,倪秋洋.依匹哌唑中间体7-羟基喹啉-(1H)-2-酮的合成[J].精细石油化工,2017,34(2):55-58.
[34]XIE S S,WANG X B,JIANG N,et al.Multi-target tacrinecoumarin hybirds:Cholinesterase and monoamine oxidase B inhibition properties against Alzheimer’s disease[J].Eur J Org Chem,2015,95(3):153-165.
[35]EMMERSON J,PHILIP J.Triazolo-pyrazine derivatives useful in the treatment of disorders of the central nervous system:WO 2014085284[P].2014.
[36]SHI Z H,LIN G,SHI Q P,et al.Synthesis and structure:Activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors[J].Bioorg Med Chem Lett,2013,23(15):1206-1211.
[2]马帅,温颖玲,周伟澄.2015年美国FDA批准上市的新药简介[J].中国医药工业杂杂志,2016,47(1):99-105.
[3]CORREL C U,SKUBAN A,OUYANG J,et al.Efficacy and safety of brexpiprazole for the treatment of acute schizophrenia:A 6-week randomized,doubleblind,place-bo-controlled trial[J].Am J Psychiatry,2015,17(2):870-880.
[4]MAEDA K,LERDRUP L,SUGINO H,et al.Brexpiprazole II:Antipsychotic-like and pro-cognitive effects of a novel serotonin-dopamine activity modulator[J].J Pharmacol Exp Ther,2014,350(4):605-614.
[5]山下博司,松原淳,大岛邦生,等.用于治疗精神疾病的哌嗪取代的苯并噻吩:CN 200680011923[P].2006.
[6]YAMASHITA H,MATSUBARA J.Priperazine substituted benzothiophenes for treatment of mental disorder:WO 2006112464[P].2006.
[7]SHINHAMA K,UTSUMI N.Method for producing benzo[b]thiophene compound:WO 201315456[P].2013.
[8]新滨光一,宇积尚登,曾田正博,等.制造苯并[b]噻吩化合物的方法:CN 201280037121[P].2012.
[9]郑永勇,金华,周峰,等.依匹哌唑的制备方法:CN201510880966[P].2015.
[10]徐奎,陶俊珏,刘经星.一种依匹哌唑新的制备:CN 201610006862[P].2016.
[11]胡清文,李乐祥,曹燕.7-(4-(4-(苯并[b]噻基)-1-哌嗪基)丁氧基)-2-(1H)-喹啉酮:CN201410714069[P].2014.
[12]罗绪,付廷印,张华娇,等.一种依匹哌唑的制备方法:CN 201510177350[P].2015.
[13]叶天健,陆修伟,郁光亮,等.一种依匹哌唑的制备方法及其中间体和中间体的合成方法:CN201610080468[P].2016.
[14]MASAHIRO M,MASAMICHI S,KOICHI T,et al.Safe and efficient decarboxylation process:A practical synthetic route to 4-chlorobenzzo[b]-thiphene[J].Org Process Res Dev,2016,20(1):86-89.
[15]ALLEN D,CALLAGHAN O,CORDIER F L,et al.An improved synthesis of substituted benzo[b]thiophenes using microwave irradiation[J].Tetrahedron Lett,2004,45(36):9645-9647.
[16]OWTON W M.Synthesis of substituted 3-trifluoromethylbenzo[b]thiophenes[J].Tetrahedron Lett,2003,44(30):7147-7149.
[17]TILSTAM U.A continuous protodecarboxylation of heteroaromatic carboxylic acids in sulfolane[J].Org Process Res Dev,2012,16(8):1149-1454.
[18]CADOT S,RAMEAU N,MANGEMATIN S,et al.Preparation of functional styrenes from biosourced carboxylic acids by copper catalyzed decarboxylation in PEG[J].Green Chem,2014,16(16):3089-3097.
[19]DUPUY S,NOLAN S P.Gold(I)-catalyzed protodecarboxylation of heteroaromatic carboxylic acids[J].Chem Eur J,2013,19(49):14034-14038.
[20]LU P,SANCHEZ C,CORNELLA J,et al.Silver-catalyzed protodecarboxylation of heteroaromatic carboxylic acids[J].Org Lett,2009,11(26):5710-5713.
[21]MAEHARA A,TSURUGI H,SATOH T,et al.Regioselective C—H functionalization directed by a removable carboxyl group:Palladium-catalyzed vinylation at the unusual position of indole and related heteroaromatic rings[J].Org Lett,2008,10(8):1159-1162.
[22]LIU K,JIA F,XI H,et al.Direct benzothiophene formation via oxygen-triggered intermolecular cyclization of thiophenols and alkynes assisted by manganese/Ph CO2H[J].Org Lett,2013,15(14):2026-2029.
[23]TOY X Y,ROSLAN I B,CHUAH G K,et al.Protod-ecarboxylation of carboxylic acids over heterogeneous silver catalysts[J].Cata Sci Technol,2014,4(3):516-523.
[24]WANG G,BEIGILMAN L,TRUONG A,et al.Compounds for the treatment of paramoxyvirus viral infections:WO 2014031784[P].2014.
[25]LI C Y,SU C,WANG H H,et al.Design and development of cyclometalated ruthenium complexes containing thiophenyl-pyridne ligand for dye-sensitized solar cells[J].Dyes Pigm,2014,100(1):57-65.
[26]NICULESU D D,NICULESCU D Z I,SUILKERBUIJK B M J M,et al.Potent BRAF kinase inhibitors based on 2,4,5-trisubstituted imidazole with naphthyl and benzothiophene 4-substituents[J].Bioorg Med Chem,2013,21(8):1284-1304.
[27]张健,田广辉.布瑞哌唑类似物的制备方法:CN201510061026[P].2015.
[28]WU C H,CHEN W M,JIANG D H,et al.An improved synthesis of 4-(1-piperazinyl)benzo[b]thiophene dihydrochloride[J].Org Process Res Dev,2015,19(3):555-558.
[29]MATUSNAGA N,KAKUT,ITOH F,et al.C17,20-lyase inhibitors I.Structure-based de novo design and SAR study of C17,20-lyase inhibitors[J].Bioorg Med Chem,2004,12(8):2251-2273.
[30]Yi IN H,CHENG K.Modulators of TLR3/DSRNA complex and uses thereof:WO 2012099785[P].2012.
[31]CHENG K,WANG X H,YIN H.Small-molecule inhibitors of the TLR3/DSRNA complex[J].J Am Chem Soc,2011,133(13):3764-3767.
[32]彭锦安,周革文.一种Brexpiprazole的制备方法:CN 201410853528[P].2014.
[33]赵爱明,倪秋洋.依匹哌唑中间体7-羟基喹啉-(1H)-2-酮的合成[J].精细石油化工,2017,34(2):55-58.
[34]XIE S S,WANG X B,JIANG N,et al.Multi-target tacrinecoumarin hybirds:Cholinesterase and monoamine oxidase B inhibition properties against Alzheimer’s disease[J].Eur J Org Chem,2015,95(3):153-165.
[35]EMMERSON J,PHILIP J.Triazolo-pyrazine derivatives useful in the treatment of disorders of the central nervous system:WO 2014085284[P].2014.
[36]SHI Z H,LIN G,SHI Q P,et al.Synthesis and structure:Activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors[J].Bioorg Med Chem Lett,2013,23(15):1206-1211.