5-[(2,4-Dioxothiazolidin-5-yl)methyl]-2-methoxybenzoic acid | 185808-79-1

• 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: 5-[(2,4-Dioxothiazolidin-5-yl)methyl]-2-methoxybenzoic acid
• 英文别名: 5-[(2.4-dioxothiazolidin-5-yl)methyl]-2-methoxybenzoic acid；5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxybenzoic acid
• CAS: 185808-79-1
• 化学式: C₁₂H₁₁NO₅S
• 分子量: 281.289
• InChiKey: KDTDAIJOPUUSTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(三氟甲基)苄胺 、 5-[(2,4-Dioxothiazolidin-5-yl)methyl]-2-methoxybenzoic acid 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-[(2,4-二氧代噻唑啉-5-基)甲基]-2-甲氧基-N-[[4-(三氟甲基)苯基]甲基]苯甲酰胺
  参考文献：
  名称：

  (3-Substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents

  摘要：

  A series of 3-[(2,4-dioxothiazolidin-5-yl)methyl]benzamide derivatives was prepared as part of a search for antidiabetic agents. A structure-activity relationship study of these compounds led to the identification of 5-[(2,4-dioxothiazolidin-5-yl)methyl] -2-methoxy-N-[[4-trifluoromethyl)phenyl]methyl]benzamide (KRP-297) as a candidate drug for the treatment of diabetes mellitus. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00039-6
• 作为产物：
  描述：

  methyl 5-(2,4-dioxothiazolidin-5-yl)methyl-2-methoxy-benzoate 在 环丁砜 、 盐酸 作用下， 生成 5-[(2,4-Dioxothiazolidin-5-yl)methyl]-2-methoxybenzoic acid
  参考文献：
  名称：

  (3-Substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents

  摘要：

  A series of 3-[(2,4-dioxothiazolidin-5-yl)methyl]benzamide derivatives was prepared as part of a search for antidiabetic agents. A structure-activity relationship study of these compounds led to the identification of 5-[(2,4-dioxothiazolidin-5-yl)methyl] -2-methoxy-N-[[4-trifluoromethyl)phenyl]methyl]benzamide (KRP-297) as a candidate drug for the treatment of diabetes mellitus. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00039-6

文献信息

• Alkali metal salt of thiazolidine-2,4-dione derivative
  申请人：——

  公开号：US20030013749A1

  公开（公告）日：2003-01-16

  The invention provides alkali metal salt of 5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide and its hydrate. A method has been found, wherein, upon preparing KRP-297, the alkali metal salt of KRP-297 and its hydrate are formed in the reaction system and, after separation and purification, they are freed again from salt, thereby KRP-297 can be advantageously purified industrially for preparation.

  本发明提供了5-[(2,4-二氧代噻唑啉-5-基)甲基]-2-甲氧基-N-[[[4-(三氟甲基)苯基]甲基]苯甲酰胺的碱金属盐及其水合物。发现了一种方法，即在制备KRP-297时，在反应体系中形成了KRP-297的碱金属盐及其水合物，经过分离和纯化后，它们再次从盐中释放出来，从而可以优化地从工业上净化KRP-297以进行制备。
• Novel stable crystal of thiazolidinedione derivative and process for producing the same
  申请人：——

  公开号：US20030101925A1

  公开（公告）日：2003-06-05

  A homogeneous crystal having excellent stability which is suitable for the industrial-scale production of 5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide (KRP-297). The novel crystal of KRP-297 is produced through recrystallization from an alcohol solvent. It is characterized by having diffraction angles (2&thgr;) at at least 9.7°, 15.0°, and 22.5° in X-ray powder diffractometry.

  具有优异稳定性的同质晶体，适用于工业规模生产5-[(2,4-二氧噻唑啉-5-基)甲基]-2-甲氧基-N-[[4-(三氟甲基)苯基]甲基]苯甲酰胺（KRP-297）。 KRP-297的新型晶体通过从醇溶剂中重结晶制备而成。它的X射线粉末衍射仪中的衍射角（2θ）至少为9.7°、15.0°和22.5°。
• Stable crystal of thiazolidinedione derivative and process for producing the same
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US06770133B2

  公开（公告）日：2004-08-03

  A homogeneous crystal having excellent stability which is suitable for the industrial-scale production of 5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide (KRP-297). The novel crystal of KRP-297 is produced through recrystallization from an alcohol solvent. It is characterized by having diffraction angles (2&thgr;) at at least 9.7°, 15.0°, and 22.5° in X-ray powder diffractometry.

  具有出色稳定性的均质晶体，适合于工业规模生产5-[(2,4-二氧噻唑啉-5-基)甲基]-2-甲氧基-N-[[4-(三氟甲基)苯基]甲基]苯甲酰胺（KRP-297）。KRP-297的新型晶体通过醇溶剂重结晶制备。其特征是在X射线粉末衍射测定中，至少具有2θ为9.7°、15.0°和22.5°的衍射角。
• Substituted benzylthiazolidine-2,4-dione derivatives
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US06780431B1

  公开（公告）日：2004-08-24

  The invention relates to substituted benzylthiazolidine-2,4-dione derivatives represented by a general formula (1) wherein R1 denotes a chlorine atom, bromine atom, nitro group, trifluoromethoxy group, ethoxy group, propoxy group or isopropoxy group, and R2 denotes a hydrogen atom or chlorine atom, their medicinally acceptable salts, their hydrates and a process for preparing them.

  本发明涉及一种由通式（1）所表示的取代苯甲基噻唑啉-2,4-二酮衍生物，其中R1表示氯原子、溴原子、硝基、三氟甲氧基、乙氧基、丙氧基或异丙氧基，R2表示氢原子或氯原子，它们的医学上可接受的盐、它们的水合物以及制备它们的方法。
• ALKALI METAL SALT OF THIAZOLIDINE-2,4-DIONE DERIVATIVE
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP1253145A1

  公开（公告）日：2002-10-30

  The invention provides alkali metal salt of 5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[4-(trifluoromethyl) phenyl]methyl]benzamide and its hydrate. A method has been found, wherein, upon preparing KRP-297, the alkali metal salt of KRP-297 and its hydrate are formed in the reaction system and, after separation and purification, they are freed again from salt, thereby KRP-297 can be advantageously purified industrially for preparation.

  本发明提供 5-[(2,4-二氧代噻唑啉-5-基)甲基]-2-甲氧基-N-[[4-(三氟甲基)苯基]甲基]苯甲酰胺的碱金属盐及其水合物。现已发现一种方法，在该方法中，制备 KRP-297 时，KRP-297 的碱金属盐及其水合物在反应体系中形成，经过分离和纯化后，它们又从盐中释放出来，因此 KRP-297 可有利地进行工业纯化制备。