NEW PROCESS FOR THE SYNTHESIS OF UP 269-6, A 1,2,4-TRIAZOLO[1,5-C]PYRIMIDINE DERIVATIVE AS A POTENT ORALLY ACTIVE ANGIOTENSIN II ANTAGONIST

Boyer T.; Nicolai E.; Teulon JM.; Fournel L.

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NEW PROCESS FOR THE SYNTHESIS OF UP 269-6, A 1,2,4-TRIAZOLO[1,5-C]PYRIMIDINE DERIVATIVE AS A POTENT ORALLY ACTIVE ANGIOTENSIN II ANTAGONIST

机译：合成269，1,2,4-三唑并[1,5-C]嘧啶衍生物作为强效口服活性血管紧张素II拮抗剂的新方法

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A new synthetic route to prepare the 2-hydroxy-5-methyl-7-n-propyl-8-[[2'-(1H-tetrazol-5-yl)biphenyl- 4-yl]methyl]-[1,2,4]triazolo[1,5-c]pyrimidine (UP 269-6, Ripisartan) is described. UP 269-6 is a non-peptide angiotensin II antagonist currently in phase II clinical trials for the treatment of hypertension and chronic heart failure. Its development needed a suitable process for industrial production. The laboratory scale synthesis was optimized and particularly two key steps: 4-hydrazinopyrimidine formation without isolation of the 4-chloro intermediate acid its cyclization into triazolo[1,5-c]pyrimidine derivative without isolation of the triazolo[4,3-c]pyrimidine isomer using urea in N-methylpyrrolidone at 160 degrees C. This cyclization process affords a new and efficient way to prepare directly 2-hydroxytriazolo[1 5-c]pyrimidine without isolation of the corresponding triazolo[4,3-c] pyrimidine. [References: 8]

机译：制备2-羟基-5-甲基-7-正丙基-8-[[2'-（1H-四唑-5-基）联苯-4-基]甲基]-[1,2]的新合成路线描述了，4]三唑并[1，5-c]嘧啶（UP 269-6，Ripisartan）。 UP 269-6是一种非肽类血管紧张素II拮抗剂，目前正处于II期临床试验中，用于治疗高血压和慢性心力衰竭。它的发展需要适合工业生产的工艺。优化了实验室规模的合成，尤其是两个关键步骤：在不分离4-氯中间酸的情况下形成4-肼基嘧啶，无需分离三唑并[4,3-c]，将其环化成三唑并[1,5-c]嘧啶衍生物。嘧啶异构体，是在160℃下在N-甲基吡咯烷酮中使用脲的。这种环化过程提供了一种直接制备2-羟基三唑并[1 5-c]嘧啶的新有效方法，而无需分离相应的三唑并[4,3-c]嘧啶。 [参考：8]

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《Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry》 |1996年第4期|共5页
作者
Boyer T.; Nicolai E.; Teulon JM.; Fournel L.;
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正文语种 eng
中图分类有机化学;
关键词
Receptor antagonist; Enalapril; Up-269-6;

机译：受体拮抗剂;依那普利;Up-269-6;

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1. NEW PROCESS FOR THE SYNTHESIS OF UP 269-6, A 1,2,4-TRIAZOLO[1,5-C]PYRIMIDINE DERIVATIVE AS A POTENT ORALLY ACTIVE ANGIOTENSIN II ANTAGONIST [J] . Boyer T., Nicolai E., Teulon JM., Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry . 1996,第4期

机译：合成269，1,2,4-三唑并[1,5-C]嘧啶衍生物作为强效口服活性血管紧张素II拮抗剂的新方法
2. Synthesis of novel pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives: Potent and selective adenosine A3 receptor antagonists [J] . BandaV., ChandrasekaranB., K?seM., Archiv der Pharmazie . 2013,第10期

机译：新型吡啶并[3,2-e] [1,2,4]三唑并[1,5-c]嘧啶衍生物的合成：强力和选择性腺苷A3受体拮抗剂
3. Pyrazolo(4,3-e)1,2,4-triazolo(1,5-c)pyrimidine derivatives as highly potent and selective human A(3) adenosine receptor antagonists: influence of the chain at the N(8) pyrazole nitrogen. [J] . Baraldi PG, Cacciari B, Romagnoli R, Journal of Medicinal Chemistry . 2000,第25期

机译：Pyrazolo（4,3-e）1,2,4-triazolo（1,5-c）嘧啶衍生物作为高效和选择性的人A（3）腺苷受体拮抗剂：在N（8）吡唑氮原子上的链影响。
4. DESIGN, SYNTHESIS AND CONFORMATIONAL ANALYSIS OF POTENT ANGIOTENSIN II LOSARTAN BASED ANTAGONIST [C] . Minos Matsoukas, Amalia Resvani, Konstantinos Kelaidonis the European Peptide Symposium . 2007

机译：高效血管紧张素II氯沙坦拮抗剂的设计，合成及构象分析
5. I. Catalytically active and recyclable zirconocene functionalized polymeric disks. II. Solid phase and solution phase synthesis of 2-arylcycloalka-2,4-dienone derivatives employing 1-phenylsulfanyl)methylphenylsulfone. [D] . Hok, Saphon. 2004

机译：I.催化活性和可回收的锆茂官能化的聚合物盘。二。使用1-苯基硫烷基）甲基苯基砜的2-芳基环烷基-2，4-二烯酮衍生物的固相和溶液相合成。
6. In vitro and in vivo effects of UP 269-6 a new potent orally active nonpeptide angiotensin II receptor antagonist on vascular smooth muscle cell proliferation [O] . A Virone-Oddos, V Desangle, D Provost, 1997

机译：新型有效口服活性非肽血管紧张素II受体拮抗剂UP 269-6对血管平滑肌细胞增殖的体外和体内作用
7. Heteroaromatization with 4-Hydroxycoumarin Part II: Synthesis of Some New Pyrano[2,3-d]pyrimidines, [1,2,4]triazolo[1,5-c]pyrimidines and Pyrimido[1,6-b]-[1,2,4]triazine Derivatives [O] . A. H. Bedair, A. H. Fakery, N. A. El-Hady, 2001

机译：4-羟基香豆素的异芳构化第二部分：一些新的吡喃并[2,3-d]嘧啶，[1,2,4]三唑并[1,5-c]嘧啶和嘧啶并[1,6-b] - [1]的合成，2,4]三嗪衍生物

NEW PROCESS FOR THE SYNTHESIS OF UP 269-6, A 1,2,4-TRIAZOLO[1,5-C]PYRIMIDINE DERIVATIVE AS A POTENT ORALLY ACTIVE ANGIOTENSIN II ANTAGONIST

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