CAS: 84088-42-6; 4-Hydroxy-N,1-Dimethyl-2-Oxo-N-Phenyl-1,2-Dihydroquinoline-3-Carboxamide

该化合物是一种合成免疫性循环化合物,可能被用于治疗自发性免疫疾病和某些癌症,其行动机制包括调节细胞基生产,特别是抑制TNF-α和IL-1β等亲食性细胞基质,同时加强抗炎反应.Roquinimex在临床前研究中显示出其有效性,因为它能够抑制过度免疫活化,使它成为风湿类关节炎和多发性硬化症等疾病的候选体.其精美的药性皮肤特征和口服生物利用率进一步支持其治疗潜力.研究继续探索其更广泛的免疫监管效应和临床在肿瘤学和慢性炎病方面的适用性.

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物理性质

MSDS等安全信息

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ECHA物质C&L通报

上下游产品

CAS号57931-81-4 3-Quinolinecarb... | CAS号100-61-8 N-甲基苯胺 | CAS号10328-92-4 N-甲基靛红酸酐 | CAS号84088-88-0 methyl 3-(N-met... | CAS号57513-54-9 4-羟基-1-甲基-2-氧代-... | CAS号118-48-9 靛红酸酐 | CAS号118-92-3 邻氨基苯甲酸

合成工艺路线路线简述

  • 合成目标产物 Roquinimex 主要起始原料 N-Methylaniline And 3-Quinolinecarboxylic Acid, 1,2-Dihydro-4-Hydroxy-1-Methyl-2-Oxo-, Methyl Ester
  • 57513-54-9 = 84088-42-6
    反应条件:1.1 Solvents: Toluene; 4 H,Reflux
    标题:Structure-Activity Relationships Studies Of The Anti-Angiogenic Activities Of Linomide
    作者:Shi,Jiandong; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2003 卷标:13(6) 页码:1187-1189]

    105-53-3 + 10328-92-4 = 84088-42-6
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 2.5 H,120 °C2.1 Solvents: Toluene; 4 H,Reflux
    标题:Structure-Activity Relationships Studies Of The Anti-Angiogenic Activities Of Linomide
    作者:Shi,Jiandong; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2003 卷标:13(6) 页码:1187-1189]

    105-53-3 = 84088-42-6
    反应条件:1.1 Solvents: 1,4-Dioxane; 20 °C; 1 H,Rt1.2 Reagents: Sodium Hydride Solvents: Dimethylformamide; 5 °C; 5 H,Rt1.3 Reagents: Sodium Hydride Solvents: Dimethylformamide; 5 H,85 °C; Cooled1.4 Reagents: Water2.1 Solvents: Toluene; 6 H,Reflux
    标题:Synthesis And Biological Evaluation Of New 1,2-Dihydro-4-Hydroxy-2-Oxo-3-Quinolinecarboxamides For Treatment Of Autoimmune Disorders: Structure-Activity Relationship
    作者:Joensson,Stig; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2004 卷标:47(8) 页码:2075-2088]

    = 84088-42-6
    反应条件:1.1 Reagents: Barium Hydroxide Solvents: Methanol; 20 H,Rt2.1 Reagents: Oxalyl Chloride Solvents: Diethyl Ether,Dimethylformamide; 1 H,Rt2.2 1 H2.3 Reagents: Ammonium Chloride Solvents: Dichloromethane
    标题:Synthesis Of Dissymmetric Malonic Acid Monoamides From Symmetric Dithiomalonates
    作者:Wauke,Hisashi; Et Al
    参考文献:Chemistryselect 日期:2016 卷标:1(21) 页码:6830-6833]

    84088-50-6 = 84088-42-6
    反应条件:1.1 Reagents: Acetic Acid; Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,80 - 85 °C; 85 °C -> 63 °C1.3 Reagents: Methanol; 63 °C; 63 °C -> 13 °C2.1 Reagents: Dicyclohexylcarbodiimide Solvents: Toluene; 2 H,80 - 85 °C; 85 °C -> 10 °C
    标题:Using Doe To Achieve Reliable Drug Administration: A Case Study
    作者:Sjoevall,Sven; Et Al
    参考文献:Organic Process Research & Development 日期:2004 卷标:8(5) 页码:802-807]

    85-91-6 + 60657-74-1 = 84088-42-6
    反应条件:1.1 Reagents: Oxalyl Chloride Solvents: Diethyl Ether,Dimethylformamide; 1 H,Rt1.2 1 H1.3 Reagents: Ammonium Chloride Solvents: Dichloromethane
    标题:Synthesis Of Dissymmetric Malonic Acid Monoamides From Symmetric Dithiomalonates
    作者:Wauke,Hisashi; Et Al
    参考文献:Chemistryselect 日期:2016 卷标:1(21) 页码:6830-6833]

    57513-54-9 = 84088-42-6
    反应条件:1.1 Solvents: Toluene; 6 H,Reflux
    标题:Synthesis And Biological Evaluation Of New 1,2-Dihydro-4-Hydroxy-2-Oxo-3-Quinolinecarboxamides For Treatment Of Autoimmune Disorders: Structure-Activity Relationship
    作者:Joensson,Stig; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2004 卷标:47(8) 页码:2075-2088]

    57931-81-4 = 84088-42-6
    反应条件:1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Toluene; 2 H,80 - 85 °C; 85 °C -> 10 °C
    标题:Using Doe To Achieve Reliable Drug Administration: A Case Study
    作者:Sjoevall,Sven; Et Al
    参考文献:Organic Process Research & Development 日期:2004 卷标:8(5) 页码:802-807]

    16854-73-2 = 84088-42-6
    反应条件:1.1 Reagents: Oxygen Catalysts: [2-(Hydroxy-Ko)-4-Methoxybenzoato(2-)-Ko]Copper Solvents: Acetonitrile; 1.5 H,Reflux2.1 Reagents: Barium Hydroxide Solvents: Methanol; 20 H,Rt3.1 Reagents: Oxalyl Chloride Solvents: Diethyl Ether,Dimethylformamide; 1 H,Rt3.2 1 H3.3 Reagents: Ammonium Chloride Solvents: Dichloromethane
    标题:Synthesis Of Dissymmetric Malonic Acid Monoamides From Symmetric Dithiomalonates
    作者:Wauke,Hisashi; Et Al
    参考文献:Chemistryselect 日期:2016 卷标:1(21) 页码:6830-6833]

    108-59-8 + 10328-92-4 = 84088-42-6
    反应条件:1.1 Reagents: Sodium Methoxide Solvents: Dimethylformamide; Rt; 90 Min,80 - 90 °C; 90 °C -> 83 °C1.2 10 Min,83 °C; 83 °C -> 96 °C; 96 °C -> 40 °C1.3 Reagents: Water; 40 °C -> 20 °C; 1.5 H,20 °C1.4 Reagents: Hydrochloric Acid Solvents: Water; Ph 1,20 °C -> 9 °C; Overnight,9 °C2.1 Reagents: Acetic Acid; Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,80 - 85 °C; 85 °C -> 63 °C2.3 Reagents: Methanol; 63 °C; 63 °C -> 13 °C3.1 Reagents: Dicyclohexylcarbodiimide Solvents: Toluene; 2 H,80 - 85 °C; 85 °C -> 10 °C
    标题:Using Doe To Achieve Reliable Drug Administration: A Case Study
    作者:Sjoevall,Sven; Et Al
    参考文献:Organic Process Research & Development 日期:2004 卷标:8(5) 页码:802-807]

    = 84088-42-6
    反应条件:1.1 Solvents: Diethyl Ether; 0 °C; 16 H,0 °C -> Rt2.1 Reagents: Oxygen Catalysts: [2-(Hydroxy-Ko)-4-Methoxybenzoato(2-)-Ko]Copper Solvents: Acetonitrile; 1.5 H,Reflux3.1 Reagents: Barium Hydroxide Solvents: Methanol; 20 H,Rt4.1 Reagents: Oxalyl Chloride Solvents: Diethyl Ether,Dimethylformamide; 1 H,Rt4.2 1 H4.3 Reagents: Ammonium Chloride Solvents: Dichloromethane
    标题:Synthesis Of Dissymmetric Malonic Acid Monoamides From Symmetric Dithiomalonates
    作者:Wauke,Hisashi; Et Al
    参考文献:Chemistryselect 日期:2016 卷标:1(21) 页码:6830-6833
📜靛红酸酐置于sodium Hydride体系中,用 N,N-二甲基甲酰胺,甲苯 作为反应溶剂,化学反应 16.0H,反应生成 罗喹美克
参考文献:Synthesis And Biological Evaluation Of New 1,2-Dihydro-4-Hydroxy-2-Oxo-3-Quinolinecarboxamides For Treatment Of Autoimmune Disorders: Structure−activity Relationship
标题:Synthesis And Biological Evaluation Of New 1,2-Dihydro-4-Hydroxy-2-Oxo-3-Quinolinecarboxamides For Treatment Of Autoimmune Disorders: Structure−activity Relationship
摘要:Roquinimex-Related 3-Quinolinecarboxamide Derivatives Were Prepared And Evaluated For Treatment Of Autoimmune Disorders. The Compounds Were Tested In Mice For Their Inhibitory Effects On Disease Development In The Acute Experimental Autoimmune Encephalomyelitis Model And Selected Compounds In The Beagle Dog For Induction Of Proinflammatory Reaction. Structure-Activity Relationships Are Discussed. Compound 8C,Laquinimod,Showed Improved Potency And Superior Toxicological Profile Compared To The Lead Compound Roquinimex (1B,Linomide) And Was Selected For Clinical Studies (Currently In Phase Ii).
DOI:10.1021/jm031044W

海关参考信息

专利信息


专利号:US-2012177593-A1
优先权日:2009-07-20
标 题 :Synthesis of dendrimer conjugates
发明人：BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH
权利人:BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH; UNIV MICHIGAN
摘要:The present invention relates to novel methods of synthesis of therapeutic and diagnostic dendrimers. In particular, the present invention is directed to novel dendrimer conjugates, novel methods of synthesizing the same, compositions comprising the conjugates, as well as systems and methods utilizing the conjugates (e.g., in diagnostic and/or therapeutic settings (e.g., for the delivery of therapeutics, imaging, and/or targeting agents (e.g., in disease (e.g., cancer, inflammatory disease) diagnosis and/or therapy, pain therapy, etc.)). Accordingly, dendrimer conjugates of the present invention may further comprise at least two different components for targeting, imaging, sensing, and/or providing a therapeutic or diagnostic material and/or monitoring response to therapy. Furthermore, the novel synthesis methods of certain embodiments of the present invention provide significant advantages with regard to total reaction time and simplicity.

专利号:US-2022233673-A1
优先权日:2019-06-04
标 题:METHODS OF PRODUCING SHIGA TOXIN B-SUBUNIT (STxB) MONOMERS AND OLIGOMERS, AND USES THEREOF
发明人：BILLET ANNE; SCHMIDT FRÉDÉRIC; JOHANNES LUDGER; SERVENT DENIS; MOURIER GILLES; TARTOUR ÉRIC; KAY MICHAEL; FULCHER JAMES M
权利人:INST CURIE; CENTRE NAT RECH SCIENT; INST NAT SANTE RECH MED; COMMISSARIAT A LENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES CEA; APHP ASSIST PUBLIQUE HOPITAUX DE PARIS; UNIV PARIS; UNIV OF UTAH RESEARCH FOUDATION; UNIV UTAH RES FOUND
摘要:A method of producing a monomer of a Shiga toxin B-subunit (STxB) protein or of a variant thereof by peptide chemical synthesis, as well as to a method of producing a pentamer of the STxB protein or of the variant thereof. The methods are particularly advantageous as they overcome major issues typically observed in peptide chemical synthesis, including solubility and purity issues.

专利号:US-8734846-B2
优先权日:2008-06-16
标 题 :Methods for the preparation of targeting agent functionalized diblock copolymers for use in fabrication of therapeutic targeted nanoparticles
发明人：ALI MIR M; HRKACH JEFF; ZALE STEPHEN E; ALVAREZ DE CIENFUEGOS LUIS
权利人:BIND BIOSCIENCES INC
摘要:This application provides nanoparticles and methods of making nanoparticles using pre-functionalized poly(ethylene glycol)(also referred to as PEG) as a macroinitiator for the synthesis of diblock copolymers. Ring opening polymerization yields the desired poly(ester)-poly (ethylene glycol)-targeting agent polymer that is used to impart targeting capability to therapeutic nanoparticles. This “polymerization fromâ€? approach typically employs precursors of the targeting agent wherein the reactivity of functional groups of the targeting agent is masked using protecting groups. Also described is a “coupling toâ€? that utilized the poly(ethylene glycol)-targeting agent conjugate where the targeting agent remains in its native un-protected form. This method uses “orthogonalâ€? chemistry that exhibit no cross reactivity towards functional groups typically found within targeting agents of interest.

专利号:US-2013035307-A1
优先权日:2010-01-26
标 题:Methods for treating or preventing the spread of cancer using semi-synthetic glycosaminoglycosan ethers
发明人：PRESTWICH GLENN D; KENNEDY THOMAS P
权利人:UNIV UTAH RES FOUND; PRESTWICH GLENN D; KENNEDY THOMAS P
摘要:Described herein are methods for the treatment and prevention of tumor metastasis using alkylated and fluoroalkylated semi-synthetic glycosaminoglycan ethers (“SAGEsâ€?). The synthesis of sulfated alkylated and fluoroalkylated SAGEs is also described.

专利号:US-2008214827-A1
优先权日:2004-02-03
标 题:Synthesis of Cyanoimino-Benzoimidazoles
发明人：GOEHRING R RICHARD; WHITEHEAD JOHN; SHAO BIN
权利人:EURO CELTIQUE SA
摘要:Disclosed in certain embodiments is a process for synthesizing a compound of formula (V) and salts thereof.

专利号:US-9220714-B2
优先权日:2006-03-16
标 题 :Nitrofuran compounds for the treatment of cancer and angiogenesis
发明人：SAULNIER SHOLLER GISELLE L; SWAMY NARASIMHA; KALKUNTE STAYAN; SINGH RAKESH K; BRARD LAURENT; KIM KYU KWANG
权利人:WOMEN AND INFANTS HOSPITAL OF RHODE ISLAND; UNIV BROWN; WOMEN AND INFANTS HOSPITAL RHODE ISLAND
摘要:The invention is directed to the synthesis and use of nitrofuran compounds, especially Nifurtimox, as medicaments to treat cancer, especially neuroblastoma, and to inhibit angiogenesis. The invention also provides compositions, unit dosage forms, and kits comprising the compounds.

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主要参考文献


1: Hasan AM, Gatea FK. Novel effect of topical Roquinimex and its combination with Clobetasol on an imiquimod-induced model of psoriasis in mice. Naunyn Schmiedebergs Arch Pharmacol. 2024 Jul;397(7):5219-5232. doi: 10.1007/s00210-024-02947-6. Epub 2024 Jan 24. 245(Pt 1):114896. doi: 10.1016/j.ejmech.2022.114896. Epub 2022 Nov 4. 23(3):1773. doi: 10.3390/ijms23031773.
4: Priolkar RNS, Shingade S, Palkar M, Desai SM. Design, Synthesis, and Characterization of Novel Linomide Analogues and their Evaluation for Anticancer Activity. Curr Drug Discov Technol. 2020;17(2):203-212. doi: 10.2174/1570163815666181008151037.
125:400-410. doi: 10.1016/j.ejmech.2016.09.062. Epub 2016 Sep 21. 9(1):49-57. doi: 10.1586/17512433.2016.1108189. Epub 2015 Nov 4.

合成参考文献


参考文献:10.1007/s10637-011-9716-3
摘要:Rodrigues JR, Charris J, Ferrer R, Gamboa N, Angel J, Nitzsche B, Hoepfner M, Lein M, Jung K, Abramjuk C. Effect of quinolinyl acrylate derivatives on prostate cancer in vitro and in vivo. Invest New Drugs. 2012 Aug;30(4):1426–33. doi: 10.1007/s10637-011-9716-3.
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