N-[1-Oxo-6-(thiazol-2-ylsulfanyl)-indan-5-yl]-methanesulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: N-[1-Oxo-6-(thiazol-2-ylsulfanyl)-indan-5-yl]-methanesulfonamide
• 英文别名: N-[1-oxo-6-(1,3-thiazol-2-ylsulfanyl)-2,3-dihydroinden-5-yl]methanesulfonamide
• 化学式: C₁₃H₁₂N₂O₃S₃
• 分子量: 340.448
• InChiKey: DXXOQPYKXLLPNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-Amino-6-(2-thiazolylthio)-1-indanone 在 sodium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-[1-Oxo-6-(thiazol-2-ylsulfanyl)-indan-5-yl]-methanesulfonamide
  参考文献：
  名称：

  Cyclooxygenase-2 Inhibitors. Synthesis and Pharmacological Activities of 5-Methanesulfonamido-1-indanone Derivatives

  摘要：

  The recent discovery of an alternative form cyclooxygenase (cyclooxygenase-2, COX-2), which has been proposed to play a significant role in inflammatory conditions, may provide an opportunity to develop anti-inflammatory drugs with fewer side effects than existing nonsteroidal anti-inflammatory drugs (NSAIDs). We have now identified 6-[(2,4-difluorophenyl)thio]-5-methanesulfonamido-1-indanone (20) (L-745,337) as a potent, selective, and orally active COX-2 inhibitor. The structure-activity relationships in this series have been extensively studied. Ortho- and para-substituted B-phenyl substitutents are optimal for in vitro potency. Replacement of this phenyl ring by a variety of heterocycles gave compounds that were less active. The methanesulfonamido group seems to be the optimal group at the 5-position of the indanone system. Compound 20 has an efficacy profile that is superior or comparable to that of the nonselective COX inhibitor indomethacin in animal models of inflammation, pain, and fever and appears to be nonulcerogenic within the dosage ranges required for functional efficacy. Although 20 and its oxygen linkage analog 2 (flosulide) are equipotent in the in vitro assays, compound 20 is more potent in the rat paw edema assay, has a longer t(1/2) in squirrel monkeys, and seems less ulcergenic than 2 in rats.

  DOI：

  10.1021/jm00025a007

文献信息

• PHARMACEUTICAL COMPOSITIONS CONTAINING A COX-II INHIBITOR AND A MUSCLE RELAXANT
  申请人：Osmotica Corp.

  公开号：EP1362585A2

  公开（公告）日：2003-11-19

  The present invention provides a pharmaceutical composition and dosage form containing in combination a COX-II inhibitor and a muscle relaxant. The pharmaceutical composition is useful for the treatment of pain and pain related disorders and symptoms. The combination provides an improved therapeutic response as compared to either drug alone. The pharmaceutical composition can be included in any dosage form.

  本发明提供了一种药物组合物和剂型，其中含有一种 COX-II 抑制剂和一种肌肉松弛剂。该药物组合物可用于治疗疼痛及疼痛相关疾病和症状。与单独使用其中一种药物相比，该组合物可提供更好的治疗反应。该药物组合物可以包含在任何剂型中。
• Pharmaceutical formulation containing muscle relaxant and COX-II inhibitor
  申请人：Sen Nilendu

  公开号：US20050100594A1

  公开（公告）日：2005-05-12

  Disclosed is an extended release pharmaceutical formulation comprising a muscle relaxant drug, such as tizanidine, in combination with a cyclooxygenase-2 inhibitor, such as valdecoxib. The formulations are useful in the treatment and management of painful inflammatory conditions associated with, for example, skeletal muscle spasms.

  本发明公开了一种缓释药物制剂，该制剂由肌肉松弛剂药物（如替扎尼丁）与环氧化酶-2 抑制剂（如伐地昔布）组合而成。该制剂可用于治疗和控制与骨骼肌痉挛等相关的疼痛性炎症。
• Topical pharmaceutical compositions
  申请人：Krishnan Anandi

  公开号：US20050096371A1

  公开（公告）日：2005-05-05

  A hydroalcoholic topical pharmaceutical composition is provided comprising a therapeutically effective amount of a therapeutic agent comprising one or more selective cyclooxygenase-2 (COX-2) inhibitors or pharmaceutically acceptable salts or esters thereof solubilized in a solubilizing amount of a penetration vehicle system comprising a skin penetration enhancing effective amount of at least one monohydric alcohol and at least two non-volatile organic compounds selected from the group consisting of pyrrolidones, polyol ethers, polyols and mixtures thereof. Also provided is a process for its preparation.

  本发明提供了一种水醇局部药物组合物，该组合物包含治疗有效量的治疗剂，该治疗剂包含一种或多种选择性环氧化酶-2 (COX-2) 抑制剂或其药学上可接受的盐或酯，该治疗剂溶解在渗透载体系统的溶解量中，该渗透载体系统包含皮肤渗透增强有效量的至少一种一元醇和至少两种非挥发性有机化合物，这些非挥发性有机化合物选自由吡咯烷酮、多元醇醚、多元醇及其混合物组成的组。此外，还提供了一种制备方法。
• COX-2 INHIBITORS IN COMBINATION WITH NMDA-BLOCKERS FOR TREATING PAIN
  申请人：Algos Pharmaceutical Corporation

  公开号：EP1146905A1

  公开（公告）日：2001-10-24
• Pharmaceutical compositions containing a COX-II inhibitor and a muscle relaxant
  申请人：——

  公开号：US20040204413A1

  公开（公告）日：2004-10-14

  The present invention provides a pharmaceutical composition and dosage form containing in combination a COX-II inhibitor and a muscle relaxant. The pharmaceutical composition is useful for the treatment of pain and pain related disorders and symptoms. The combination provides an improved therapeutic response as compared to either drug alone. The pharmaceutical composition can be included in any dosage form.