methyl 2-bromo-3-(3-methoxycarbonyl-4-fluorophenyl)propionate | 185808-81-5

• 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: methyl 2-bromo-3-(3-methoxycarbonyl-4-fluorophenyl)propionate
• 英文别名: methyl 5-(2-bromo-3-methoxy-3-oxopropyl)-2-fluorobenzoate
• CAS: 185808-81-5
• 化学式: C₁₂H₁₂BrFO₄
• 分子量: 319.127
• InChiKey: SDOFGRJGTWBMPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-bromo-3-(3-methoxycarbonyl-4-fluorophenyl)propionate 在 环丁砜 、 盐酸 、 氰基磷酸二乙酯 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-trifluoromethylbenzyl)-5-(2,4-dioxothiazolidin-5-yl)methyl-2-fluorobenzamide
  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：

  2-氟-5-氨基苯甲酸甲酯 、 丙烯酸甲酯（MA） 在 copper(I) oxide 、 氢溴酸 、 sodium nitrite 作用下， 生成 methyl 2-bromo-3-(3-methoxycarbonyl-4-fluorophenyl)propionate
  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

• N-benzyldioxothiazolidylbenzamide derivatives and processes for
  申请人：Kyorin Pharameuticals Co., Ltd.

  公开号：US06001862A1

  公开（公告）日：1999-12-14

  The present invention provides novel N-benzyldioxothiazolidylbenzamide derivatives that improve the insulin resistance and have potent hypoglycemic and lipid-lowering effects and processes for preparing the same, and relates to N-benzyldioxothiazolidylbenzamide derivatives characterized by being represented by a general formula (1) ##STR1## [wherein R.sup.1 and R.sup.2 denote identically or differently hydrogen atoms, lower alkyl groups with carbon atoms of 1 to 4, lower alkoxy groups with carbon atoms of 1 to 3, lower haloalkyl groups with carbon atoms of 1 to 3, lower haloalkoxy groups with carbon atoms of 1 to 3, halogen atoms, hydroxyl groups, nitro groups, amino groups which may be substituted with lower alkyl group(s) with carbon atoms of 1 to 3 or hetero rings, or R.sup.1 and R.sup.2 link to form a methylenedioxy group, R.sup.3 denotes a lower alkoxy group with carbon atoms of 1 to 3, hydroxyl group or halogen atom, and dotted line indicates double bond or single bond in combination with solid line], and processes for preparing the same.

  本发明提供了新型N-苄基二氧噻唑基苯甲酰胺衍生物，其改善胰岛素抵抗并具有强效的降血糖和降脂作用，并提供了制备它们的方法。涉及到的N-苄基二氧噻唑基苯甲酰胺衍生物的特征在于由通式（1）表示： 其中R^1和R^2表示相同或不同的氢原子，具有1到4个碳原子的低碳基，具有1到3个碳原子的低碳氧基，具有1到3个碳原子的低卤代烷基，具有1到3个碳原子的低卤代氧基，卤素原子，羟基，硝基，氨基（可以用具有1到3个碳原子的低碳基或杂环代替的氨基），或R^1和R^2连接形成亚甲二氧基基团，R^3表示具有1到3个碳原子的低碳氧基，羟基或卤素原子，虚线表示双键或与实线结合的单键。同时还提供了制备它们的方法。
• N-benzyldioxothiazolidylbenzamide derivatives and process for producing
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US06030990A1

  公开（公告）日：2000-02-29

  The present invention provides novel N-benzyldioxothiazolidylbenzamide derivatives that improve the insulin resistance and have potent hypoglycemic and lipid-lowering effects and processes for preparing the same, and relates to N-benzyldioxothiazolidylbenzamide derivatives characterized by being represented by a general formula (1) ##STR1## wherein R.sup.1 and R.sup.2 denote identically or differently hydrogen atoms, lower alkyl groups with carbon atoms of 1 to 4, lower alkoxy groups with carbon atoms of 1 to 3, lower haloalkyl groups with carbon atoms of 1 to 3, lower haloalkoxy groups with carbon atoms of 1 to 3, halogen atoms, hydroxyl groups, nitro groups, amino groups which may be substituted with lower alkyl group(s) with carbon atoms of 1 to 3 or hetero rings, or R.sup.1 and R.sup.2 link to form a methylenedioxy group, R.sup.3 denotes a lower alkoxy group with carbon atoms of 1 to 3, hydroxyl group or halogen atom, and dotted line indicates double bond or single bond in combination with solid line, and processes for preparing the same.

  本发明提供了一种新型的N-苯甲酰基二氧噻唑基苯甲酰胺衍生物，其改善胰岛素抵抗，并具有强效的降血糖和降脂作用，以及制备该衍生物的过程。该N-苯甲酰基二氧噻唑基苯甲酰胺衍生物的特征在于其由一般式（1）所表示，其中R1和R2表示相同或不同的氢原子，具有1到4个碳原子的低碳基，具有1到3个碳原子的低烷氧基，具有1到3个碳原子的低卤代烷基，具有1到3个碳原子的低卤代烷氧基，卤素原子，羟基，硝基，氨基，可以用具有1到3个碳原子的低碳基或杂环取代的氨基，或R1和R2连接形成亚甲二氧基基团，R3表示具有1到3个碳原子的低烷氧基，羟基或卤素原子，虚线表示与实线相结合的双键或单键，以及制备该衍生物的过程。
• N-BENZYLDIOXOTHIAZOLIDYLBENZAMIDE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP0846693A1

  公开（公告）日：1998-06-10

  The present invention provides novel N-benzyldioxothiazolidylbenzamide derivatives that improve the insulin resistance and have potent hypoglycemic and lipid-lowering effects and processes for preparing the same, and relates to N-benzyldioxothiazolidylbenzamide derivatives characterized by being represented by a general formula (1) [wherein R1 and R2 denote identically or differently hydrogen atoms, lower alkyl groups with carbon atoms of 1 to 4, lower alkoxy groups with carbon atoms of 1 to 3, lower haloalkyl groups with carbon atoms of 1 to 3, lower haloalkoxy groups with carbon atoms of 1 to 3, halogen atoms, hydroxyl groups, nitro groups, amino groups which may be substituted with lower alkyl group(s) with carbon atoms of 1 to 3 or hetero rings, or R1 and R2 link to form a methylenedioxy group, R3 denotes a lower alkoxy group with carbon atoms of 1 to 3, hydroxyl group or halogen atom, and dotted line indicates double bond or single bond in combination with solid line], and processes for preparing the same.

  本发明提供了改善胰岛素抵抗、具有强效降血糖和降血脂作用的新型N-苄基二氧代噻唑烷基苯甲酰胺衍生物及其制备工艺，涉及N-苄基二氧代噻唑烷基苯甲酰胺衍生物，其特征在于由通式(1)表示 [其中 R1 和 R2 表示相同或不同的氢原子、碳原子数为 1 至 4 的低级烷基、碳原子数为 1 至 3 的低级烷氧基、碳原子数为 1 至 3 的低级卤代烷基、碳原子数为 1 至 3 的低级卤代烷氧基、卤素原子、羟基、硝基、可被碳原子数为 1 至 3 的低级烷基或杂环取代的氨基，或 R1 和 R2 连接形成亚甲基二氧基，R3 表示碳原子数为 1 至 3 的低级烷氧基、羟基或卤素原子，虚线表示双键或与实线结合的单键]，以及制备上述物质的工艺。
• US6001862A
  申请人：——

  公开号：US6001862A

  公开（公告）日：1999-12-14
• US6030990A
  申请人：——

  公开号：US6030990A

  公开（公告）日：2000-02-29