CAS: 854107-55-4; (Z)-5-((Z)-3-Chloro-4-((R)-2,3-Dihydroxypropoxy)Benzylidene)-2-(Propylimino)-3-(O-Tolyl)Thiazolidin-4-One

该化合物是选择性的硫磷-1-磷受体调节器,主要针对S1P1受体,旨在治疗自发性免疫疾病,特别是多发性硬化症,通过调制淋巴细胞循环,有效减少循环性淋巴细胞数量,从而减轻与自免疫条件相关的炎症反应. 蛋白质显示口服生物利用率高,而且有利于药用植物,允许一次日服.其化学结构包括一个火药核心,有助于其受体选择性和活性.该物质经过了各种临床试验,以评估其功效和安全性,表明有可能改善在自发性免疫紊乱症中的患者结果.与许多药剂一样,副作用可能发生,其使用应当由保健专业人员加以监测.

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MSDS等安全信息

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上下游产品

(2Z,5Z)-5-(3-Chloro-4-Hydroxybenzylidene)-2-Propylimino-3-O-Tolylthiazolidin-4-One 1029435-58-2

合成工艺路线路线简述

  • 22323-82-6 + 2420-16-8 = 854107-55-4
    反应条件:1.1 Reagents: Tributylphosphine,1,1′-(Azodicarbonyl)Dipiperidine Solvents: Toluene; Heated; 2 H,Rt; 18 H,60 °C2.1 Reagents: Sodium Acetate Solvents: Acetic Acid; 4 H,110 °C2.2 Solvents: Water; 1 H,100 °C2.3 Reagents: Sodium Methoxide Solvents: Methanol; 30 Min,40 °C
    标题:2-Imino-Thiazolidin-4-One Derivatives As Potent,Orally Active S1P1 Receptor Agonists
    作者:Bolli,Martin H.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2010 卷标:53(10) 页码:4198-4211]

    854107-53-2 + 854107-61-2 = 854107-55-4
    反应条件:1.1 Reagents: Sodium Acetate Solvents: Acetic Acid; 4 H,110 °C1.2 Solvents: Water; 1 H,100 °C1.3 Reagents: Sodium Methoxide Solvents: Methanol; 30 Min,40 °C
    标题:2-Imino-Thiazolidin-4-One Derivatives As Potent,Orally Active S1P1 Receptor Agonists
    作者:Bolli,Martin H.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2010 卷标:53(10) 页码:4198-4211]

    614-69-7 + 598-21-0 = 854107-55-4
    反应条件:1.1 Solvents: Dichloromethane; 20 °C; 15 Min,20 °C; 20 °C -> 0 °C1.2 < 5 °C; 15 Min,0 °C1.3 Reagents: Pyridine; 0 °C; 15 Min,0 °C; 0 °C -> 20 °C2.1 Reagents: Sodium Acetate Solvents: Acetic Acid; 4 H,110 °C2.2 Solvents: Water; 1 H,100 °C2.3 Reagents: Sodium Methoxide Solvents: Methanol; 30 Min,40 °C
    标题:2-Imino-Thiazolidin-4-One Derivatives As Potent,Orally Active S1P1 Receptor Agonists
    作者:Bolli,Martin H.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2010 卷标:53(10) 页码:4198-4211]

    614-69-7 = 854107-55-4
    反应条件:1.1 Solvents: Methanol; 30 °C; 3.5 H,Rt1.2 Reagents: Pyridine; 16 H,Rt1.3 Reagents: Hydrochloric Acid Solvents: Water1.4 Reagents: Sodium Bicarbonate Solvents: Water; Ph 82.1 Reagents: Sodium Acetate Solvents: Acetic Acid; 4 H,110 °C2.2 Solvents: Water; 1 H,100 °C2.3 Reagents: Sodium Methoxide Solvents: Methanol; 30 Min,40 °C
    标题:2-Imino-Thiazolidin-4-One Derivatives As Potent,Orally Active S1P1 Receptor Agonists
    作者:Bolli,Martin H.; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2010 卷标:53(10) 页码:4198-4211
📜(2Z,5Z)-5-(3-Chloro-4-Hydroxybenzylidene)-2-Propylimino-3-O-Tolylthiazolidin-4-One,(R)-(-)-3-氯-1,2-丙二醇置于(R)-(-)-3-氯-1,2-丙二醇体系中,用84的收率获得产物珀奈莫德;
参考文献: Process For The Preparation Of|(2Z,5Z)-5-(3-Chloro-4-((R)-2,3-Dihydroxypropoxy)Benzylidene)-2-(Propylimino)-3-|(O-Tolyl)Thiazolidin-4-One And Intermediate Used In Said Process[fr] Procédé De Préparation De (2Z,5Z)-5-(3-Chloro-4-((R)-2,3-Dihydroxypropoxy)Benzylidene)-2-(Propylimino)-3-|(O-Tolyl)Thiazolidin-4-One Et Intermédiaire Utilisé Dans Ledit Procédé
标题: Process For The Preparation Of|(2Z,5Z)-5-(3-Chloro-4-((R)-2,3-Dihydroxypropoxy)Benzylidene)-2-(Propylimino)-3-|(O-Tolyl)Thiazolidin-4-One And Intermediate Used In Said Process[fr] Procédé De Préparation De (2Z,5Z)-5-(3-Chloro-4-((R)-2,3-Dihydroxypropoxy)Benzylidene)-2-(Propylimino)-3-|(O-Tolyl)Thiazolidin-4-One Et Intermédiaire Utilisé Dans Ledit Procédé
摘要:本发明涉及一种制备(2Z,5Z)-5-(3-氯-4-((R)-2,3-二羟丙氧基)苯甲醛基)-2-(丙基亚胺基)-3-(O-甲苯基)噻唑啉-4-酮的新工艺,以及在该工艺中使用的新中间体(R)-3-氯-4-(2,3-二羟丙氧基)苯甲醛.(2Z,5Z)-5-(3-氯-4-((R)-2,3-二羟丙氧基)苯甲醛基)-2-(丙基亚胺基)-3-(O-甲苯基)噻唑啉-4-酮在wo 2005/054215中被描述为免疫抑制剂.本发明还涉及一种制备(R)-3-氯-4-(2,3-二羟丙氧基)苯甲醛的新工艺.

海关参考信息

专利信息


专利号:US-10906888-B2
优先权日:2016-07-14
标 题:Pyrimidine carboxamides as inhibitors of Vanin-1 enzyme
发明人：CASIMIRO-GARCIA AGUSTIN; STROHBACH JOSEPH WALTER; HEPWORTH DAVID; LOVERING FRANK ELDRIDGE; CHOI CHULHO; ALLAIS CHRISTOPHE PHILIPPE; WRIGHT STEPHEN WAYNE
权利人:PFIZER
摘要:Compounds, pharmaceutically acceptable salts thereof, are disclosed wherein the compounds have the structure of (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

专利号:US-10308615-B2
优先权日:2015-05-29
标 题:Heterocyclic compounds as inhibitors of Vanin-1 enzyme
发明人：CASIMIRO-GARCIA AGUSTIN; CONDON JEFFREY SCOTT; FLICK ANDREW CHRISTOPHER; GOPALSAMY ARIAMALA; KIRINCICH STEVEN J; MATHIAS JOHN PAUL; STROBACH JOSEPH WALTER; XIANG JASON SHAOYUN; XING LI HUANG; WANG XIAOLUN
权利人:PFIZER
摘要:Compounds, pharmaceutically acceptable salts thereof, are disclosed wherein the compounds have the structure of n nas defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

专利号:US-2018230127-A1
优先权日:2015-08-13
标题 :Bicyclic-Fused Heteroaryl Or Aryl Compounds
发明人：ANDERSON DAVID RANDOLPH; CURRAN KEVIN JOSEPH; GAVRIN LORI KRIM; GOLDBERG JOEL ADAM; LEE ARTHUR; LOWE MICHAEL DENNIS; PATNY AKSHAY; PIERCE BETSY SUSAN; SAIAH EDDINE; TRZUPEK JOHN DAVID
权利人:PFIZER
摘要:Compounds, tautomers and pharmaceutically acceptable salts of the compounds of Formula (Ia) are disclosed which are inhibitors of Interleukin-1 receptor associated kinase (IRAK4). Methods of treatment, methods of synthesis, and intermediates are also disclosed as defined in the specification.

专利号:US-2023119606-A1
优先权日:2020-02-18
标 题:Immune cell modulators
发明人：SHERDEN NATHANIEL; YU SHEN; STONER ISAAC
权利人:OCTAGON THERAPEUTICS INC
摘要:Disclosed are immune cell-selective small molecule compounds that modulate certain immune cell-specific receptors and enzymes, and methods of their synthesis and use to treat proliferative disorders.

专利号:US-10316018-B2
优先权日:2015-08-27
标题 :Bicyclic-fused heteroaryl or aryl compounds as IRAK4 modulators
发明人：LEE KATHERINE LIN; ALLAIS CHRISTOPHE PHILIPPE; DEHNHARDT CHRISTOPH MARTIN; GAVRIN LORI KRIM; HAN SEUNGIL; HEPWORTH DAVID; LEE ARTHUR; LOVERING FRANK ELDRIDGE; MATHIAS JOHN PAUL; OWEN DAFYDD RHYS; PAPAIOANNOU NIKOLAOS; SAIAH EDDINE; STROHBACH JOSEPH WALTER; TRZUPEK JOHN DAVID; WRIGHT STEPHEN WAYNE; ZAPF CHRISTOPH WOLFGANG
权利人:PFIZER
摘要:Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, n nas defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

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主要参考文献


1: Juif PE, Hoch M, D'Ambrosio D, Dingemanse J. Biocomparison of Three Formulations of the S1P1 Receptor Modulator Ponesimod in Healthy Subjects. Drugs R D. 2015 Jun;15(2):203-10. doi: 10.1007/s40268-015-0095-7.
2: Scherz MW, Brossard P, D'Ambrosio D, Ipek M, Dingemanse J. Three different up-titration regimens of ponesimod, an S1P1 receptor modulator, in healthy subjects. J Clin Pharmacol. 2015 Jun;55(6):688-97. doi: 10.1002/jcph.467. Epub 2015 Feb 10. doi: 10.3109/08923973.2014.993084. doi: 10.1159/000368837. Epub 2014 Nov 14. doi: 10.1111/bcpt.12336. Epub 2014 Nov 8. doi: 10.3109/00498254.2014.955832. Epub 2014 Sep 4. doi: 10.1016/S0140-6736(14)60803-5. Epub 2014 Aug 10. doi: 10.1016/S0140-6736(14)61039-4. Epub 2014 Aug 10. doi: 10.1016/j.ejps.2014.07.005. Epub 2014 Jul 19. doi: 10.1007/s10928-014-9362-4. Epub 2014 Jun 15. doi: 10.1136/jnnp-2013-307282. Epub 2014 Mar 21.
12: Brossard P, Scherz M, Halabi A, Maatouk H, Krause A, Dingemanse J. Multiple-dose tolerability, pharmacokinetics, and pharmacodynamics of ponesimod, an S1P1 receptor modulator: favorable impact of dose up-titration. J Clin Pharmacol. 2014 Feb;54(2):179-88. doi: 10.1002/jcph.244. Epub 2014 Jan 9. doi: 10.1007/s00228-013-1625-2. Epub 2013 Dec 22. doi: 10.1371/journal.pone.0077296. eCollection 2013.
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