ethyl 5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-1-oxo-3-quinolinecarboxylate | 675574-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-1-oxo-3-quinolinecarboxylate
• 英文别名: ethyl 5-ethyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate；1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester；ethyl 5-ethyl-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxylate
• CAS: 675574-87-5
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: UQNHXZNQUZCGSX-UHFFFAOYSA-N

物化性质

• 沸点：
  419.4±45.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-1-oxo-3-quinolinecarboxylate 在 盐酸 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 10.5h， 生成 帕奎莫德
  参考文献：
  名称：

  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
• 作为产物：
  描述：

  5-Ethyl-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 在 sodium methylate 作用下， 以 正庚烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ethyl 5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-1-oxo-3-quinolinecarboxylate
  参考文献：
  名称：

  [EN] METHOD FOR MANUFACTURING OF QUINOLINE-3-CARBOXAMIDES
  [FR] PROCÉDÉ POUR LA FABRICATION DE QUINOLÉINE-3-CARBOXAMIDES

  摘要：

  一种制备式（I）化合物的方法，通过反应适当的烷基酯和苯胺衍生物，在含有沸点在68-191°C范围内的脂肪溶剂或脂肪溶剂混合物的回流混合物中，将回流混合物的蒸汽凝结；用醇清除剂或醇清除剂混合物处理凝结的蒸汽；并将凝结的蒸汽返回到反应混合物中。

  公开号：

  WO2012004338A1

文献信息

• Development and evaluation of a non-peptidic ligand for the molecular imaging of inflammatory processes using S100A9 (MRP14) as a novel target
  作者：A. Faust、T. Völler、F. Busch、M. Schäfers、J. Roth、S. Hermann、T. Vogl

  DOI：10.1039/c5cc07019h

  日期：——

  We describe the development and first evaluation of a novel S100A9 specific molecular imaging probe (Cy5.5-CES271) for optical imaging of local inflammatory activity in vivo.

  我们描述了一种新型的S100A9特异性分子成像探针（Cy5.5-CES271），用于体内局部炎症活动的光学成像的开发和首次评估。
• Quinoline derivatives
  申请人：Active Biotech AB

  公开号：US06077851A1

  公开（公告）日：2000-06-20

  The invention relates to compounds of general formula (I) ##STR1## wherein R is selected from ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl and allyl; R.sub.4 is selected from hydrogen and pharmaceutically acceptable inorganic and organic cations; R.sub.5 is selected from methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, chloro, bromo, CF.sub.3, and OCH.sub.x F.sub.y ; wherein x=0-2, y=1-3 with the proviso that x+y=3; R.sub.6 is hydrogen; or R.sub.5 and R.sub.6 taken together are methylenedioxy; and any tautomer hereof. The invention also relates to pharmaceutical compositions containing a compound of the general formula (I) together with a pharmaceutically acceptable carrier. Included are also processes for the preparation of the compounds of formula (I), as well as methods of treating mammals suffering from diseases resulting from autoimmunity and pathological inflammation by administering a compound having the formula (I) to said mammal.

  本发明涉及一般式（I）的化合物：##STR1## 其中R选择自乙基，正丙基，异丙基，正丁基，异丁基，仲丁基和烯丙基；R.sub.4选择自氢和药学上可接受的无机和有机阳离子；R.sub.5选择自甲基，乙基，正丙基，异丙基，甲氧基，乙氧基，氯，溴，CF.sub.3和OCH.sub.x F.sub.y；其中x=0-2，y=1-3，但x+y=3；R.sub.6为氢；或R.sub.5和R.sub.6共同为亚甲二氧基；以及其任何互变异构体。本发明还涉及含有一般式（I）的化合物和药学上可接受的载体的制药组合物。还包括制备式（I）化合物的过程，以及通过给所述哺乳动物注射具有式（I）的化合物来治疗由自身免疫和病理性炎症引起的疾病的方法。
• [EN] METHOD FOR THE PREPARATION OF 2-AMINO-6-ETHYLBENZOIC ACID<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACIDE 2-AMINO-6-ÉTHYLBENZOÏQUE
  申请人：ACTIVE BIOTECH AB

  公开号：WO2011054874A1

  公开（公告）日：2011-05-12

  The present invention relates to a novel method for the production of 2- amino-6-ethylbenzoic acid wherein7-amino-3-methylphtalide or 7-amino-3- hydroxy-3-methylphtalide is reduced to 2-amino-6-ethylbenzoic acid in water or in a mixture of a water miscible solvent and water at a pH of 7 or higher using a hydrogenation catalyst selected from Raney nickel and palladium based catalysts and using a hydrogen source selected from the group consisting of hydrogen gas, formic acid derivatives and cyclohexen. The invention also relates to 2-amino-6-ethylbenzoic acid produced with this method, and to use of such 2-amino-6-ethylbenzoic acid in the production of paquinimod.

  本发明涉及一种生产2-氨基-6-乙基苯甲酸的新方法，其中7-氨基-3-甲基邻苯二甲酸酰胺或7-氨基-3-羟基-3-甲基邻苯二甲酸酰胺在水或水可溶溶剂和水的混合物中，在pH为7或更高的条件下，使用Raney镍和基于钯的催化剂选择的氢化催化剂和选择的氢源来还原为2-氨基-6-乙基苯甲酸。本发明还涉及使用该方法生产的2-氨基-6-乙基苯甲酸，以及在生产帕奎尼莫德时使用这种2-氨基-6-乙基苯甲酸的用途。
• METHOD FOR MANUFACTURING OF QUINOLINE-3-CARBOXAMIDES
  申请人：Active Biotech AB

  公开号：EP2590949B1

  公开（公告）日：2015-11-25
• QUINOLINE-3-CARBOXAMIDE COMPOUNDS AND THEIR USE IN DIAGNOSIS
  申请人：Westfaelische Wihelms-Universitaet Muenster

  公开号：US20170333577A1

  公开（公告）日：2017-11-23

  The present application provides quinoline-3-carboxamide compounds covalently linked to a label for use in the diagnosis of an inflammatory disease at local site. The above mentioned compounds can be used to detect or image accumulation of S100A9 in the body of a subject at sites of inflammation, using in vivo non-invasive molecular imaging techniques for the detection of said compounds. Accordingly, labeled quinoline-3-carboxamide compounds can be applied to evaluate the risk of a subject of developing an inflammatory disease and to follow the progress of the disease.