tert-butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate

• 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: tert-butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate
• 英文别名: N-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]-5-methoxyphenyl]-N-methylcarbamic acid t-butyl ester；tert-butyl N-[2-[acetyl-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]amino]-5-methoxyphenyl]-N-methylcarbamate
• 化学式: C₂₅H₂₉N₃O₇S
• 分子量: 515.587
• InChiKey: SVBQQPIPKIYKJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-(2-amino-5-methoxyphenyl)-N-methylcarbamic acid t-butyl ester 、 碳酸氢钠 、 4-(2,4-二氧代噻唑啉-5-基甲基)苯氧乙酸 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 以85%的产率得到tert-butyl N-{2-{4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetylamino}-5-methoxyphenyl}-N-methylcarbamate
  参考文献：
  名称：

  Intermediates for the synthesis of benzimidazole derivatives and a process for the preparation thereof

  摘要：

  本发明提供了一种制备苯并咪唑衍生物(I)或其药学上可接受的盐的方法，其中R1为C1-C6烷基，C1-C6烷氧基等，R2为C1-C6烷基，R3为氢或保护基，具有出色的降血糖作用，该方法包括将胺衍生物(III)与羧酸衍生物(II)缩合得到化合物(IV)，然后在酸的存在下使化合物(IV)环化。

  公开号：

  US20030008907A1

文献信息

• Process for Producing Thiazolidinedione Compound and Production Intermediate Thereof
  申请人：Nakamura Yoshitaka

  公开号：US20080103185A1

  公开（公告）日：2008-05-01

  There are provided crystals of a thiazolidinedione derivative having excellent prophylactic and therapeutic effects on a disease caused by insulin resistance and a process for producing the thiazolidinedione derivative with a high purity. As described above, a process for producing a compound represented by the general formula (A) or a salt thereof, comprising converting 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid represented by the following formula into a compound of the general formula (I), wherein X=a halogen atom; then reacting the compound with a compound represented by the general formula (II), wherein R 1 , R 2 , R 3 and R 4 =a hydrogen atom, a hydroxyl group, C1-C6 alkyl, C1-C6 alkoxy, benzyloxy, acetoxy, trifluoromethyl or a halogen atom, R 5 =C1-C6 alkyl, and R 6 =a protecting group for an amino group, to produce a compound represented by the general formula (III); and subsequently cyclizing the compound into the final product, and crystals of a compound represented by the general formula (A) or a salt thereof.

  提供了一种噻唑烷二酮衍生物的晶体，具有对因胰岛素抵抗引起的疾病具有卓越的预防和治疗效果，并提供了一种高纯度制备噻唑烷二酮衍生物的方法。如上所述，提供了一种制备通式（A）化合物或其盐的方法，包括将以下式子所示的4-[(2,4-二氧噻唑烷-5-基)甲基]苯氧乙酸转化为通式（I）化合物，其中X为卤素原子; 然后将该化合物与通式（II）化合物反应，其中R1、R2、R3和R4为氢原子、羟基、C1-C6烷基、C1-C6烷氧基、苄氧基、乙酰氧基、三氟甲基或卤素原子，R5为C1-C6烷基，R6为氨基保护基，以制备通式（III）化合物; 然后将该化合物环化为最终产物，并提供了通式（A）化合物或其盐的晶体。
• Thiazolidinedione compound
  申请人：Nakamura Yoshitaka

  公开号：US20110092555A1

  公开（公告）日：2011-04-21

  A compound which is 5-4-[(6-methoxy-1-methyl-1H-benzimidazol-2-yl)methoxy]benzyl}thiazolidine-2,4-dione hydrochloride, in crystal form wherein a powder x-ray diffraction pattern obtained by irradiation with a Cu Kα line shows main peaks at interplanar spacings d=14.29, 7.12, 5.34, 4.97, 4.74, 3.95, 3.85, 3.75, 3.55, 3.51, 3.15, 2.84, 2.76, 2.52 and 2.37.

  这是一种晶体形式的5-4-[(6-甲氧基-1-甲基-1H-苯并咪唑-2-基)甲氧基]苄基}噻唑烷-2,4-二酮盐酸盐化合物，其通过Cu Kα线辐射获得的粉末X射线衍射图案显示出主要峰位于间隔距离d=14.29，7.12，5.34，4.97，4.74，3.95，3.85，3.75，3.55，3.51，3.15，2.84，2.76，2.52和2.37。
• INTERMEDIATES FOR THE SYNTHESIS OF BENZIMIDAZOLE COMPOUNDS AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Sankyo Company, Limited

  公开号：EP1191019A1

  公开（公告）日：2002-03-27

  This invention provides a process for the preparation of a benzimidazole derivative (I) or a pharmaceutically acceptable salt thereof, wherein R1 is C1-C6 alkyl, C1-C6 alkoxyl, etc., R2 is C1-C6 alkyl, and R3 is hydrogen or a protecting group, which exhibits excellent hyopoglycemic action, said process comprising condensation of an amine derivative (III) with a carboxylic acid derivatives (II) to afford a compound (IV), followed by cyclization of compound (IV) in the presence of an acid.

  本发明提供了一种苯并咪唑衍生物(I)或其药学上可接受的盐的制备方法、 其中，R1 为 C1-C6 烷基、C1-C6 烷氧基等，R2 为 C1-C6 烷基，R3 为氢或保护基团，具有优异的降血糖作用，所述工艺包括胺衍生物 (III) 与羧酸衍生物 (II) 缩合得到化合物 (IV)，然后化合物 (IV) 在酸存在下环化。
• Intermediates for the synthesis of benzimidazole compounds and process for the preparation thereof
  申请人：Sankyo Company Limited

  公开号：EP1607385A1

  公开（公告）日：2005-12-21

  This invention provides a process for the preparation of a benzimidazole derivative (9) or a pharmaceutically acceptable salt thereof, by condensation of a compound of formula (6) with a compound of formula (7) in the presence of a condensing agent to afford a compound of formula (8), followed by, if necessary removal of the amino protecting group of compound (8), and then cyclization of compound (8) in the presence of an acid, wherein R1e, R2e, R3e and R4e are each independently hydrogen, hydroxyl, alkyl, alkoxy, benzyloxy, acetoxy, trifluoromethyl or halogen, R7e is alkyl and R8e is hydrogen or an amino protecting group, wherein R1e, R2e, R3e, R4e, R7e and R8e are as defined above, wherein R1e, R2e, R3e, R4e, and R7e are as defined above.

  本发明提供了一种制备苯并咪唑衍生物（9）或其药学上可接受的盐的工艺，其方法是：在缩合剂存在下，将式（6）化合物与式（7）化合物缩合，得到式（8）化合物，然后必要时去除化合物（8）的氨基保护基，再在酸存在下将化合物（8）环化、 其中 R1e、R2e、R3e 和 R4e 各自独立地为氢、羟基、烷基、烷氧基、苄氧基、乙酰氧基、三氟甲基或卤素，R7e 为烷基，R8e 为氢或氨基保护基、 其中 R1e、R2e、R3e、R4e、R7e 和 R8e 如上定义、 其中 R1e、R2e、R3e、R4e 和 R7e 如上定义。
• PROCESS FOR PRODUCING THIAZOLIDINEDIONE COMPOUND AND PRODUCTION INTERMEDIATE THEREOF
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1894929A1

  公开（公告）日：2008-03-05

  There are provided crystals of a thiazolidinedione derivative having excellent prophylactic and therapeutic effects on a disease caused by insulin resistance and a process for producing the thiazolidinedione derivative with a high purity. A process for producing a compound represented by the general formula (A) or a salt thereof, comprising converting 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid represented by the following formula into a compound of the general formula (I), wherein X = a halogen atom; then reacting the compound with a compound represented by the general formula (II), wherein R1, R2, R3 and R4 = a hydrogen atom, a hydroxyl group, C1-C6 alkyl, C1-C6 alkoxy, benzyloxy, acetoxy, trifluoromethyl or a halogen atom, R5 = C1-C6 alkyl, and R6 = a protecting group for an amino group, to produce a compound represented by the general formula (III); and subsequently cyclizing the compound into the final product, and crystals of a compound represented by the general formula (A) or a salt thereof.

  本发明提供了一种对胰岛素抵抗引起的疾病具有良好预防和治疗效果的噻唑烷二酮衍生物晶体，以及一种高纯度噻唑烷二酮衍生物的生产工艺。一种生产通式(A)所代表的化合物或其盐的工艺，包括将下式所代表的 4-[(2,4-二氧代噻唑烷-5-基)甲基]苯氧乙酸转化为通式(I)的化合物，其中 X＝卤素原子；然后将该化合物与通式 (II) 所代表的化合物反应，其中 R1、R2、R3 和 R4 = 氢原子、羟基、C1-C6 烷基、C1-C6 烷氧基、苄氧基、乙酰氧基、三氟甲基或卤原子，R5 = C1-C6 烷基，R6 = 氨基的保护基团，生成通式 (III) 所代表的化合物；然后将该化合物环化成最终产物，以及通式 (A) 所代表的化合物或其盐的结晶。