α-羟基取代双膦酸类化合物的合成研究进展
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摘要
α-羟基取代双膦酸类化合物为双膦酸类骨吸收抑制剂,在临床上用以治疗以骨质疏松症为代表的骨代谢疾病,有着良好的临床应用价值和广阔的市场前景。按起始物料的不同将合成方法分成了3类。论述了优点和缺点,对其合成研究进展进行了综述。
α-Hydroxy substituted bisphosphonic acid analogues are bisphosphonate bone resorption inhibitors, and are clinically used to treat bone metabolic diseases such as osteoporosis. These analogues have good clinical value and broad market prospect. These methods were categorized into three classes based on starting materials. The merits and disadvantages of these routes were discussed, and progress in synthesis was reviewed.
α-Hydroxy substituted bisphosphonic acid analogues are bisphosphonate bone resorption inhibitors, and are clinically used to treat bone metabolic diseases such as osteoporosis. These analogues have good clinical value and broad market prospect. These methods were categorized into three classes based on starting materials. The merits and disadvantages of these routes were discussed, and progress in synthesis was reviewed.
引文
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[6]陈婷,王涛,贺红武.双膦酸衍生物的合成[J].化学试剂,2003,25(5):267-270.
[7]路坦,李小伟,徐海斌.依替膦酸二钠预防髋臼骨折术后异位骨化的临床效果[J].广东医学,2011,32(21):2 849-2 851.
[8]徐明,许宋锋,于秀淳.帕米膦酸二钠治疗累及股骨近端多发性纤维结构不良的24例报告[J].中国骨与关节杂志,2014,3(5):378-384.
[9]周沛然,洪霞,夏维波,等.阿仑膦酸钠对绝经后骨质疏松症患者生活质量的影响[J].中华骨质疏松和骨矿盐疾病杂志,2013,6(3):207-212.
[10]郭郡浩,姚茹冰,赵智明,等.利塞膦酸钠胶囊治疗绝经后骨质疏松症[J].医学研究生学报,2009,22(2):154-157.
[11]段鹏,涂萍,吴和平,等.唑来膦酸在骨质疏松患者中的应用及疗效[J].中国骨质疏松杂志,2014,20(4):420-422.
[12]程蒙,崔彦芝,李颖,等.唑来膦酸在乳腺癌辅助治疗中的临床应用及机制探讨[J].中国肿瘤,2014,23(5):394-398.
[13]刘庆春,李森,曹金,等.伊班膦酸钠中间体3-(N-甲基戊胺基)丙酸盐酸盐的合成[J]精细化工中间体,2011,41(6):11-13.
[14]张秀立,张宇佳,王璐璐,等.利塞膦酸钠的合成研究[J].药学实践杂志,2013,31(6):448-450.
[15]李鹏.帕米膦酸二钠的合成[J].中国医药工业杂志,2009,40(6):406-407.
[16]李家明,童元峰,张永.高血钙症治疗药唑来膦酸的合成方法改进[J].中国药物化学杂志,2002,12(3):164-165.
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[19]Alanne A L,Hyvonen H,Lahtinen M,et al.Systematic study of the physicochemical properties of a homologous series of aminobisphosphonates[J].Molecules,2012,17(9):10 928-10 945.
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[22]朱君,赵会,徐瑞.伊班膦酸钠的合成[J].辽宁化工,2015,11(44):1 298-1 299.
[23]Martin K.Process for making zoledronic acid:US:2010/0130746[P].2010-05-27.
[24]程传玲,汪洋,郝二军,等.新药唑来膦酸钠的合成工艺改进[J].合成化学,2010,18(4):517-519.
[25]Bhushan K R,Tanaka E,Frangioni J V.Synthesis of conjugatable bisphosphonates for molecular imaging of large animals[J].Angewandte Chemie International Edition,2007,46(42):7 969-7971.
[26]Tromelin A,Manouni D E,Burgada R.α-Cetophosphonates et esters cycliques d'hydroxymethylenes diphosphonates syntheses,structures Et hydrolyse[J].Phosphorus and Sulfur and the Related Elements,1986,27(3):301-312.
[27]Mallard I,Benech J M,Lecouvey M,et al.Substituted benzyl hydroxy bisphosphonates:synthesis and hydrolysis[J].Phosphorus and Sulfur and the Related Elements,2000,162:15-23.
[28]Griffiths D V,Hugh J M,Brown J W,et al.The synthesis of 1-amino-2-hydroxy-and 2-amino-1-hydroxy-substituted ethylene-1,1-bisphosphonic acids and their N-methylated derivatives[J].Tetrahedron,1997,53(52):17 815-17 822.
[29]Lecouvey M,Mallard I,Bailly T,et al.A mild and efficient one-pot synthesis of 1-hydroxymethylene-1,1-bisphosphonic acids.Preparation of new tripod ligands[J].Tetrahedron Letters,2001,42(48):8 475-8 478.
[30]Manouni D E,Leroux Y,Burgada R.Synthesis ofα-cetophosphonates et esters hydroxy methylene diphosphonates III[J].Phosphorus and Sulfur and the Related Elements,1989,42(1-2):73-83.
[31]王腾飞,吕高超,林建国,等.帕米膦酸酯的制备与表征[J].应用化工,2016,45(7):1 220-1 223.
[32]Mckenna C E,Kashemirov B A,Li Z M.Synthetic approaches to biologically active bisphosphonates and phosphonocarboxylates[J].Phosphorus and Sulfur and the Related Elements,1999,144-146(1):313-316.
[33]Bosch I L J.Process for producing 4-amino-1-hidroxybutylidene-1,1-bisphosphonic acid and its trihydrated monosodic salt:WO,01/10874[P].2001-02-15.
[34]孙伶俐.羟基乙叉二膦酸合成新方法的研究[J].广东化工,2014,41(15):54-55.
[35]Jozsef N.Industrial process for the synthesis of 2-substituted 1-(hydroxy-ethylidene)-1,1-bisphosphonic acids of high purity and the salts thereof:WO,2004/067541[P].2004-08-12.
[36]Pierre N P.Method for the synthesis of ethane-1-hydroxy-1,1-diphosphonic acid:WO,2015/059288[P].2015-04-30.
[2]蒋利华.骨质疏松症药物治疗进展[J].中国药业,2006,15(4):325.
[3]徐东红,齐燕,李佩岚,等.骨质疏松症的药物治疗进展[J].医学理论与实践,2014,27(11):1 428-1 430.
[4]赵文新,李金恒.骨质疏松症的药物治疗进展[J].医学研究生学报,2003,16(5):386-388.
[5]Fleisch H,Russell R G G,Francis M D.Diphosphonates inhibit hydroxyl apatite dissolution in vitro and bone resorption in tissue culture and invivo[J].Science,1969,165(899):1 262-1 264.
[6]陈婷,王涛,贺红武.双膦酸衍生物的合成[J].化学试剂,2003,25(5):267-270.
[7]路坦,李小伟,徐海斌.依替膦酸二钠预防髋臼骨折术后异位骨化的临床效果[J].广东医学,2011,32(21):2 849-2 851.
[8]徐明,许宋锋,于秀淳.帕米膦酸二钠治疗累及股骨近端多发性纤维结构不良的24例报告[J].中国骨与关节杂志,2014,3(5):378-384.
[9]周沛然,洪霞,夏维波,等.阿仑膦酸钠对绝经后骨质疏松症患者生活质量的影响[J].中华骨质疏松和骨矿盐疾病杂志,2013,6(3):207-212.
[10]郭郡浩,姚茹冰,赵智明,等.利塞膦酸钠胶囊治疗绝经后骨质疏松症[J].医学研究生学报,2009,22(2):154-157.
[11]段鹏,涂萍,吴和平,等.唑来膦酸在骨质疏松患者中的应用及疗效[J].中国骨质疏松杂志,2014,20(4):420-422.
[12]程蒙,崔彦芝,李颖,等.唑来膦酸在乳腺癌辅助治疗中的临床应用及机制探讨[J].中国肿瘤,2014,23(5):394-398.
[13]刘庆春,李森,曹金,等.伊班膦酸钠中间体3-(N-甲基戊胺基)丙酸盐酸盐的合成[J]精细化工中间体,2011,41(6):11-13.
[14]张秀立,张宇佳,王璐璐,等.利塞膦酸钠的合成研究[J].药学实践杂志,2013,31(6):448-450.
[15]李鹏.帕米膦酸二钠的合成[J].中国医药工业杂志,2009,40(6):406-407.
[16]李家明,童元峰,张永.高血钙症治疗药唑来膦酸的合成方法改进[J].中国药物化学杂志,2002,12(3):164-165.
[17]焦建宇,冯怡民,史守镛,等.阿仑膦酸钠的合成[J].中国医药工业杂志,1998,29(5):202-203.
[18]吴明书,陈茹玉,黄有.双膦酸及其酯类化合物的合成研究进展[J].有机化学,2004,24(5):485-497.
[19]Alanne A L,Hyvonen H,Lahtinen M,et al.Systematic study of the physicochemical properties of a homologous series of aminobisphosphonates[J].Molecules,2012,17(9):10 928-10 945.
[20]Gore Vinayak G.Novel process:US,2009/0198062[P].2009-08-06.
[21]Dana A M,Boris A K,Charlies E M.Microwave-assisted synthesis of nitrogen-containing 1-hydroxymethylenebisphosphonate drugs[J].Tetrahedron Letters,2011,52(18):2 285-2 287.
[22]朱君,赵会,徐瑞.伊班膦酸钠的合成[J].辽宁化工,2015,11(44):1 298-1 299.
[23]Martin K.Process for making zoledronic acid:US:2010/0130746[P].2010-05-27.
[24]程传玲,汪洋,郝二军,等.新药唑来膦酸钠的合成工艺改进[J].合成化学,2010,18(4):517-519.
[25]Bhushan K R,Tanaka E,Frangioni J V.Synthesis of conjugatable bisphosphonates for molecular imaging of large animals[J].Angewandte Chemie International Edition,2007,46(42):7 969-7971.
[26]Tromelin A,Manouni D E,Burgada R.α-Cetophosphonates et esters cycliques d'hydroxymethylenes diphosphonates syntheses,structures Et hydrolyse[J].Phosphorus and Sulfur and the Related Elements,1986,27(3):301-312.
[27]Mallard I,Benech J M,Lecouvey M,et al.Substituted benzyl hydroxy bisphosphonates:synthesis and hydrolysis[J].Phosphorus and Sulfur and the Related Elements,2000,162:15-23.
[28]Griffiths D V,Hugh J M,Brown J W,et al.The synthesis of 1-amino-2-hydroxy-and 2-amino-1-hydroxy-substituted ethylene-1,1-bisphosphonic acids and their N-methylated derivatives[J].Tetrahedron,1997,53(52):17 815-17 822.
[29]Lecouvey M,Mallard I,Bailly T,et al.A mild and efficient one-pot synthesis of 1-hydroxymethylene-1,1-bisphosphonic acids.Preparation of new tripod ligands[J].Tetrahedron Letters,2001,42(48):8 475-8 478.
[30]Manouni D E,Leroux Y,Burgada R.Synthesis ofα-cetophosphonates et esters hydroxy methylene diphosphonates III[J].Phosphorus and Sulfur and the Related Elements,1989,42(1-2):73-83.
[31]王腾飞,吕高超,林建国,等.帕米膦酸酯的制备与表征[J].应用化工,2016,45(7):1 220-1 223.
[32]Mckenna C E,Kashemirov B A,Li Z M.Synthetic approaches to biologically active bisphosphonates and phosphonocarboxylates[J].Phosphorus and Sulfur and the Related Elements,1999,144-146(1):313-316.
[33]Bosch I L J.Process for producing 4-amino-1-hidroxybutylidene-1,1-bisphosphonic acid and its trihydrated monosodic salt:WO,01/10874[P].2001-02-15.
[34]孙伶俐.羟基乙叉二膦酸合成新方法的研究[J].广东化工,2014,41(15):54-55.
[35]Jozsef N.Industrial process for the synthesis of 2-substituted 1-(hydroxy-ethylidene)-1,1-bisphosphonic acids of high purity and the salts thereof:WO,2004/067541[P].2004-08-12.
[36]Pierre N P.Method for the synthesis of ethane-1-hydroxy-1,1-diphosphonic acid:WO,2015/059288[P].2015-04-30.