Methyl 3-acetylamino-4-acetyloxybenzoate | 17903-97-8

• 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 3-acetylamino-4-acetyloxybenzoate
• 英文别名: Methyl 3-acetamido-4-acetoxybenzoate；Methyl 3-acetamido-4-acetyloxybenzoate
• CAS: 17903-97-8
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: YOEJUNCLPHHZLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-acetylamino-4-acetyloxybenzoate 、 甲胺 以 水 为溶剂， 生成 3-Acetylamino-4-hydroxy-N-methylbenzamide
  参考文献：
  名称：

  Identification of urinary metabolites of ecabapide in rat

  摘要：

  1. C-14-Ecabapide, 3-[[[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl]methyl]amino-N-methyl[C-14]benzamide, was dosed orally to rat (100mg/kg). Within 48h after dosing, 36.7+/-5.4 and 55.7+/-11.8% of the administered radioactivity was recovered from urine and faeces respectively.2. The unchanged drug was the major compound excreted in the urine and accounted for 37% of the urinary radioactivity. Seven urinary metabolites were purified by preparative hplc and their structures were elucidated by mass and H-1-nmr spectrometry.3. The major metabolic pathway of ecabapide was found to be the formation of 3-amino-N-methylbenzamide produced by N-dealkylation of the secondary amine at the 3-position of the benzamide moiety followed by acetylation.4. Further metabolic pathways of the N-methylbenzamide moiety were N-demethylation via the carbinolamine derivatives, and/or aromatic hydroxylation followed by glucuronidation.

  DOI：

  10.3109/00498259509061869
• 作为产物：
  描述：

  3-氨基-4-羟基苯甲酸 在 硫酸 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 Methyl 3-acetylamino-4-acetyloxybenzoate
  参考文献：
  名称：

  Identification of urinary metabolites of ecabapide in rat

  摘要：

  1. C-14-Ecabapide, 3-[[[2-(3,4-dimethoxyphenyl)ethyl]carbamoyl]methyl]amino-N-methyl[C-14]benzamide, was dosed orally to rat (100mg/kg). Within 48h after dosing, 36.7+/-5.4 and 55.7+/-11.8% of the administered radioactivity was recovered from urine and faeces respectively.2. The unchanged drug was the major compound excreted in the urine and accounted for 37% of the urinary radioactivity. Seven urinary metabolites were purified by preparative hplc and their structures were elucidated by mass and H-1-nmr spectrometry.3. The major metabolic pathway of ecabapide was found to be the formation of 3-amino-N-methylbenzamide produced by N-dealkylation of the secondary amine at the 3-position of the benzamide moiety followed by acetylation.4. Further metabolic pathways of the N-methylbenzamide moiety were N-demethylation via the carbinolamine derivatives, and/or aromatic hydroxylation followed by glucuronidation.

  DOI：

  10.3109/00498259509061869

文献信息

• [EN] INDOLE DERIVATIVES AS cGMP-PDE INHIBITORS<br/>[FR] DERIVES D'INDOLE UTILISES EN TANT QU'INHIBITEURS DE CGMP-PDE
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1996032379A1

  公开（公告）日：1996-10-17

  (EN) This invention relates to new indole derivatives of formula (I), wherein R1 is hydrogen, halogen, nitro, carboxy, protected carboxy, acyl, etc., R2 is hydrogen, halogen, lower alkenyl, acyl, etc., R3 is lower alkenyl or lower alkyl, both of which are optionally substituted with aryl optionally substituted with one or more substituent(s) selected from the group consisting of halogen, aryl, lower alkoxy, etc., and R4 is carboxy, protected carboxy, acyl, etc., in addition to their significances above, R1 and R2, together with the carbon atoms to which they are attached, represent a 4- to 7-membered carboxylic ring optionally substituted with oxo, or its pharmaceutically acceptable salt, which is useful as a medicament; and to new use of cyclic nucleotide-PDE inhibitors.(FR) La présente invention concerne de nouveaux dérivés d'indole de formule (I), R1 représentant hydrogène, halogène, nitro, carboxy, carboxy protégé, acyle, etc.; R2 représentant hydrogène, halogène, alcényle inférieur, acyle, etc.; R3 alcényle inférieur ou alkyle inférieur, tous deux étant éventuellement substitués avec aryle éventuellement substitué avec un ou plusieurs substituants choisis dans le groupe comprenant halogènes, aryle, alcoxy inférieur, etc., et R4 représente carboxy, carboxy protégé, acyle, etc.; outre leurs significations ci-dessus, R1 et R2, avec les atomes de carbone auxquels ils sont fixés, représentent ensemble un noyau carbocyclique de 4 à 7 éléments, éventuellement substitué avec oxo; ou son sel acceptable sur le plan pharmaceutique, qui est utile comme médicament. L'invention concerne aussi un nouvel emploi d'inhibiteurs de PDE de nucléotides cycliques.

  该发明涉及公式（I）的新的吲哚衍生物，其中R1是氢，卤素，硝基，羧基，保护羧基，酰基等；R2是氢，卤素，较低的烯基，酰基等；R3是较低的烯基或较低的烷基，两者都可以选择性地用取代芳基取代，所述取代基可以选择性地来自卤素，芳基，较低的烷氧基等，R4是羧基，保护羧基，酰基等。除了上述含义外，R1和R2与它们连接的碳原子一起表示一个4到7个成员的羧酸环，该环可以选择性地用氧代取代，或其在药学上可接受的盐，作为药物使用；以及环核苷酸-PDE抑制剂的新用途。
• INDOLE DERIVATIVES AS cGMP-PDE INHIBITORS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0820441A1

  公开（公告）日：1998-01-28
• US6069156A
  申请人：——

  公开号：US6069156A

  公开（公告）日：2000-05-30
• US6358992B1
  申请人：——

  公开号：US6358992B1

  公开（公告）日：2002-03-19