6-(4-fluoro-phenyl)-3-methyl-imidazo[2,1-b]thiazole-2-carboxylic acid methyl-phenyl amide | 933212-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(4-fluoro-phenyl)-3-methyl-imidazo[2,1-b]thiazole-2-carboxylic acid methyl-phenyl amide
• 英文别名: 6-(4-fluorophenyl)-N,3-dimethyl-N-phenylimidazo[2,1-b]thiazole-2-carboxamide；6-(4-fluorophenyl)-N,3-dimethyl-N-phenylimidazo[2,1-b][1,3]thiazole-2-carboxamide
• CAS: 933212-30-7
• 化学式: C₂₀H₁₆FN₃OS
• 分子量: 365.431
• InChiKey: HJUYWCBWHDMXBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-4-甲基噻唑-5-甲酸乙酯 在 lithium hydroxide 、 O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 6-(4-fluoro-phenyl)-3-methyl-imidazo[2,1-b]thiazole-2-carboxylic acid methyl-phenyl amide
  参考文献：
  名称：

  WO2008/58641

  摘要：

  公开号：

文献信息

• Imidazo[2,1-b]thiazoles and their use as pharmaceuticals
  申请人：ZOLLER Gerhard

  公开号：US20100004299A1

  公开（公告）日：2010-01-07

  The present invention relates to derivatives of imidazo[2,1-b]thiazoles of formula I, in which R, R1 to R3 and n have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of formula I, to pharmaceutical compositions comprising them, and to the use of compounds of formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  本发明涉及公式I的咪唑[2,1-b]噻唑衍生物，其中R、R1至R3和n具有所述权利要求中所示的含义，这些化合物调节内皮型一氧化氮（NO）合酶的转录，并具有药理活性。具体而言，公式I的化合物上调内皮型NO合酶酶的表达，并可用于需要增加该酶的表达或增加NO水平或恢复降低的NO水平的情况。本发明还涉及制备公式I化合物的方法，包括它们的制药组合物，并且涉及使用公式I化合物制造用于刺激内皮型NO合酶表达或治疗各种疾病的药物，包括心血管疾病，如动脉粥样硬化，血栓形成，冠状动脉疾病，高血压和心脏衰竭等。
• IMIDAZO[2, 1-B]THIAZOLES AND THEIR USE AS PHARMACEUTICALS
  申请人：Sanofi-Aventis

  公开号：EP2086537A1

  公开（公告）日：2009-08-12
• IMIDAZO[2,1-B]THIAZOLES AND THEIR USE AS PHARMACEUTICALS
  申请人：Sanofi-Aventis

  公开号：EP2086537B1

  公开（公告）日：2011-01-26
• US8080569B2
  申请人：——

  公开号：US8080569B2

  公开（公告）日：2011-12-20
• [EN] IMIDAZO[2, 1-B]THIAZOLES AND THEIR USE AS PHARMACEUTICALS<br/>[FR] IMIDAZO[2,1-B]THIAZOLES ET LEUR UTILISATION EN TANT QUE PRODUITS PHARMACEUTIQUES
  申请人：SANOFI AVENTIS

  公开号：WO2008058641A1

  公开（公告）日：2008-05-22

  [EN] The present invention relates to derivatives of imidazo[2,1-b]thiazoles of the formula (I), in which R, R1 to R3 and n have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.
  [FR] La présente invention concerne des dérivés des imidazo[2,1-b]thiazoles de formule (I), dans lesquels R, R1 à R3 et n ont les significations indiquées dans les revendications, qui modulent la transcription de l'oxyde nitrique (NO) synthase endothéliale et représentent des composés de valeur pharmacologiquement actifs. En particulier, les composés de formule I régulent à la hausse l'expression de l'enzyme de NO synthase endothéliale et peuvent être appliqués lorsque l'on souhaite augmenter l'expression de ladite enzyme, augmenter le niveau d'oxyde nitrique ou normaliser le niveau décroissant d'oxyde nitrique. L'invention concerne en outre des procédés de préparation des composés de formule (I), des compositions pharmaceutiques les renfermant, et l'utilisation des composés de formule (I) en vue de la fabrication d'un médicament destiné à stimuler l'expression de la NO synthase endothéliale ou à traiter diverses maladies dont les troubles cardiovasculaires tels que l'athérosclérose, la thrombose, les maladies coronariennes, l'hypertension et l'insuffisance cardiaque, par exemple.