恩格列酮 | 109229-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 恩格列酮
• 英文名称: englitazone
• 英文别名: (S)-(3,4-dihydro-2-(phenyl-methyl)-2H-1-benzopyran-6-yl)methyl-thiazolidine-2,4-dione；5-[(2-benzyl-2,3-dihydrobenzopyran)-5-ylmethyl]thiazolidine-2,4-dione；5-[[(2R)-2-benzyl-6-chromanyl]methyl]-2,4-thiazolidinedione；5-[[(2R)-2-benzyl-3,4-dihydro-2H-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 109229-58-5；122228-35-7；142696-28-4
• 化学式: C₂₀H₁₉NO₃S
• 分子量: 353.442
• InChiKey: MVDXXGIBARMXSA-PYUWXLGESA-N

物化性质

• 沸点：
  562.7±19.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  恩格列酮 生成 englitazone
  参考文献：
  名称：

  降血糖药恩格列酮的光学活性2-苄基二氢苯并吡喃的合成

  摘要：

  两个合成的某些光学活性的2-苄基-2,3-二氢-4- ħ -benzopyrans和苯并吡喃-4-酮被呈现。从D-和L-苯丙氨酸开始的不对称合成用于提供2-苄基-6-（甲氧基羰基）-2,3-二氢-4 H-苯并吡喃-4-酮19的两种对映体。苯丙氨酸在硫酸水溶液中重氮化。酸转化为2-羟基-3-苯基丙酸6，将其在四个步骤中转化为1-溴-2-（4-甲氧基羰基苯氧基）-3-苯基丙烷11。（4 R，S）-苯甲酰氨基-2-苄基-2， 3-二氢-6-（甲氧基羰基）-4 H -1-苯并吡喃-4-羧酸16由11制备通过在甲磺酸溶液中用α-羟基马尿酸进行酰胺烷基化，然后将其螺烷基化为（4 R，S）-2-苄基-2,3-二氢-6-（甲氧基羰基）螺[4 H-苯并吡喃-4,4'-2 ′-苯恶唑烷] -5′-one 15.将苯恶唑烷-5-酮15水解为螺并苯甲酰胺基羧酸16后，用次氯酸钠氧化脱羧得到旋光的2-苄基-6-（甲氧羰基）-2

  DOI：

  10.1002/jhet.5570290223
• 作为产物：
  描述：

  5-<(2-benzyl-3,4-dihydro-2H-1-benzopyran-6-yl)methylene>thiazolidine-2,4-dione 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以68%的产率得到恩格列酮
  参考文献：
  名称：

  Substituted dihydrobenzopyran and dihydrobenzofuran thiazolidine-2,4-diones as hypoglycemic agents

  摘要：

  A series of dihydrobenzofuran and dihydrobenzopyran thiazolidine-2,4-diones (compounds 3-26) was synthesized from the corresponding aryl aldehydes 1 in two steps. These compounds represent conformationally restricted analogues of the novel hypoglycemic ciglitazone. The series was evaluated by hypoglycemic effects in vitro by measuring stimulation of 2-deoxyglucose uptake in L6 myocytes and stimulation of expression of the glucose transporter protein in 3T3-L1 adipocytes. In vivo hypoglycemic effects were evaluated in the genetically obese ob/ob mouse, and structure-activity relationships are discussed. On the basis of this in vivo potency, we have selected the 2(R)-benzylbenzopyran derivative to be further studied in a clinical setting.

  DOI：

  10.1021/jm00105a050

文献信息

• [EN] 5R- 5 -DEUTERATED GLITAZONES FOR RESPIRATORY DISEASE TREATMENT<br/>[FR] GLITAZONES 5R-5-DEUTÉRÉS POUR LE TRAITEMENT DE MALADIES RESPIRATOIRES
  申请人：PULMAGEN THERAPEUTICS INFLAMMATION LTD

  公开号：WO2010150014A1

  公开（公告）日：2010-12-29

  A composition comprising a 5R-5-deuterated glitazone or a salt thereof, in which composition the 5R-5 deuterated glitazone component includes less than 5% by weight in total of 5R-5-protonated glitazone, 5S-5-protonated glitazone and 5S-5- deuterated glitazone. The glitazone may be rosiglitazone or pioglitazone. Compositions may be for pulmonary inhalation for treatment of Pulmonary inflammatory disease.

  一种组合物，包括5R-5-氘代格利吡嗪或其盐，其中该组合物中的5R-5-氘代格利吡嗪成分总重量中含有少于5%的5R-5-质子化格利吡嗪、5S-5-质子化格利吡嗪和5S-5-氘代格利吡嗪。格利吡嗪可能是罗格列酮或派格列酮。该组合物可能用于治疗肺部炎症性疾病的肺部吸入。
• Combination of FBPase Inhibitors and Insulin Sensitizers for the Treatment of Diabetes
  申请人：Erion D. Mark

  公开号：US20080004226A1

  公开（公告）日：2008-01-03

  Pharmaceutical compositions containing an FBPase inhibitor and an insulin sensitizer are provided as well as methods for treating diabetes and diseases responding to increased glycemic control, an improvement in insulin sensitivity, a reduction in insulin levels, or an enhancement of insulin secretion.

  提供含有FBPase抑制剂和胰岛素增敏剂的药物组合物，以及治疗糖尿病和对增加血糖控制、改善胰岛素敏感性、降低胰岛素水平或增强胰岛素分泌有反应的疾病的方法。
• RESPIRATORY DISEASE TREATMENT
  申请人：Finch Harry

  公开号：US20110053986A1

  公开（公告）日：2011-03-03

  There is provided a pharmaceutical composition that is adapted for pulmonary administration by inhalation, which composition comprises a glitazone, such as pioglitazone or rosiglitazone, and one or more pharmaceutically acceptable carriers and/or excipients, and wherein the glitazone content of the composition consists of at least 95% by weight of the 5R enantiomer and less than 5% by weight of the 5S enantiomer. There is also provided a use and kit.

  提供了一种适用于肺部吸入的药物组合物，该组合物包括一种格列吡嗪，例如派格列酮或罗格列酮，以及一种或多种药用载体和/或赋形剂，其中该组合物的格列吡嗪含量由至少95%的5R对映体和少于5%的5S对映体组成。还提供了使用和工具包。
• Respiratory Disease Treatment
  申请人：FINCH Harry

  公开号：US20120264787A1

  公开（公告）日：2012-10-18

  There is provided a pharmaceutical composition that is adapted for pulmonary administration by inhalation, which composition comprises a glitazone, such as pioglitazone or rosiglitazone, and one or more pharmaceutically acceptable carriers and/or excipients, and wherein the glitazone content of the composition consists of at least 95% by weight of the 5R enantiomer and less than 5% by weight of the 5S enantiomer. There is also provided a use and kit.

  提供了一种适用于通过吸入进行肺部给药的制剂，该制剂包括一种glitazone，例如pioglitazone或rosiglitazone，以及一种或多种药学上可接受的载体和/或赋形剂，其中该制剂中的glitazone含量由至少95%的5R对映体和少于5%的5S对映体组成。还提供了一种用途和工具包。
• Peroxisome proliferator-activated receptor gamma ligand eluting medical device
  申请人：Medtronic AVE, Inc.

  公开号：EP1236478A1

  公开（公告）日：2002-09-04

  Implantable medical devices having an anti-restenotic coatings are disclosed. Specifically, implantable medical devices having coatings of peroxisome proliferator-activated receptor gamma (PPARy) agonists are disclosed. The anti-restenotic PPARy ligands include thiazolidinedione compounds including ciglitazone. The anti-restenotic medial devices include stents, catheters, micro-particles, probes and vascular grafts. The medical devices can be coated using any method known in the art including compounding the thiazolidinedione with a biocompatible polymer prior to applying the coating. Moreover, medical devices composed entirely of biocompatible polymer-thiazolidinedione blends are disclosed. Additionally, medical devices having a coating comprising at least one thiazolidinedione in combination with at least one additional therapeutic agent are also disclosed. Furthermore, related methods of using and making the anti-restenotic implantable devices are also disclosed.

  本研究公开了具有抗血管狭窄涂层的植入式医疗器械。具体来说，公开了具有过氧化物酶体增殖激活受体γ（PPARy）激动剂涂层的植入式医疗器械。抗子宫收缩 PPARy 配体包括噻唑烷二酮化合物，包括西格列酮。抗血管狭窄的医疗器械包括支架、导管、微颗粒、探针和血管移植物。这些医疗器械可以使用本领域已知的任何方法进行涂层，包括在涂敷涂层之前将噻唑烷二酮与生物相容性聚合物复合。此外，还公开了完全由生物相容性聚合物-噻唑烷二酮混合物组成的医疗器械。此外，还公开了具有包含至少一种噻唑烷二酮和至少一种额外治疗剂的涂层的医疗器械。此外，还公开了使用和制造抗再狭窄植入装置的相关方法。