Methyl 5-acetylamino-2-acetyloxybenzoate | 122228-38-0

• 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 5-acetylamino-2-acetyloxybenzoate
• 英文别名: methyl 5-acetamido-2-acetoxybenzoate；Methyl 2-acetoxy-5-acetamidobenzoate；methyl 5-acetamido-2-acetyloxybenzoate
• CAS: 122228-38-0
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: YGSQESDSVCYABW-UHFFFAOYSA-N

物化性质

• 沸点：
  417.7±35.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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 5-acetylamino-2-acetyloxybenzoate 在 ammonium hydroxide 作用下， 以2.0 g的产率得到5-乙酰氨基-2-羟基苯甲酰胺
  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：

  5-氨基水杨酸 在 氯化亚砜 、 硫酸 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 Methyl 5-acetylamino-2-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

• Benzoic acid derivatives and use thereof
  申请人：DAK-Laboratoriet

  公开号：US04933330A1

  公开（公告）日：1990-06-12

  A pharmaceutical composition for use in the treatment of psoriasis comprises 4-aminosalicylic acid (4-ASA) or 5-aminosalicylic acid (5-ASA) or a functional derivative thereof, said pharmaceutical composition being in a form suitable for topical administration. Furthermore, 4- or 5-ASA or a functional derivative thereof are used for the manufacture of pharmaceutical compositions for treating psoriasis, atopic dermatitis, allergic dermatitis, contact dermatitis, seborrhoic dermatitis, or acne diseases. The derivatives have the formulae: ##STR1## where W is COOX, wherein X is H, Li, Na, K, Mg.sub.0.5, Ca.sub.0.5, Zn.sub.0.5, Al.sub.0.33, Fe(II).sub.0.5, Fe(III).sub.0.33, NH.sub.4, NH.sub.3 R.sup.1, NH.sub.2 R.sup.1.sub.2, NHR.sup.1.sub.3, NR.sup.1.sub.4, or R.sup.1, where R.sup.1 is substituted or unsubstituted C.sub.1-6 -alkyl, aryl-C.sub.1-4 -alkyl, or heteroaryl-C.sub.1-4 -alkyl; or COX, where X is NR.sup.1 R.sup.1', where R.sup.1' has the same meaning as R.sup.1 defined above and R.sup.1 and R.sup.1' may be identical or different; Y is H or R.sup.1 CO, where R.sup.1 is defined as above; Z.sup.1 and Z.sup.2, which may be identical or non-identical are H, R.sup.1 or R.sup.1 CO, where R.sup.1 is defined as above, or Z.sup.1 and Z.sup.2 represent R.sup.2, where R.sup.2 is substituted or unsubstituted C.sub.1-6 -alkylidene or aryl-C.sub.1-6 -alkylidene, or heteroaryl-C.sub.1-6 -alkylidene, or Z.sup.1, Z.sup.2 together with the nitrogen atom to which they are attached may represent a 3 to 7 membered saturated or unsaturated heterocyclic ring, or may represent a group of the formula --N.dbd.N--R.sup.3 where R.sup.3 is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.

  一种用于治疗牛皮癣的药物组合物包括4-氨基水杨酸（4-ASA）或5-氨基水杨酸（5-ASA）或其功能衍生物，所述药物组合物以适合局部给药的形式存在。此外，4-或5-ASA或其功能衍生物被用于制造治疗牛皮癣、特应性皮炎、过敏性皮炎、接触性皮炎、脂溢性皮炎或痤疮疾病的药物组合物。这些衍生物的化学式为：其中W为COOX，其中X为H、Li、Na、K、Mg0.5、Ca0.5、Zn0.5、Al0.33、Fe(II)0.5、Fe(III)0.33、NH4、NH3R1、NH2R12、NHR13、NR14或R1，其中R1为取代或未取代的C1-6-烷基、芳基-C1-4-烷基或杂环芳基-C1-4-烷基；或COX，其中X为NR1R1'，其中R1'具有与上述定义的R1相同的含义，R1和R1'可以相同也可以不同；Y为H或R1CO，其中R1如上定义；Z1和Z2，可能相同也可能不同，为H、R1或R1CO，其中R1如上定义，或Z1和Z2代表R2，其中R2为取代或未取代的C1-6-烷基亚甲基或芳基-C1-6-烷基亚甲基，或杂环芳基-C1-6-烷基亚甲基，或Z1、Z2与它们连接的氮原子一起可能代表3至7成员的饱和或不饱和杂环环，或可能代表具有化学式--N.dbd.N--R3的基团，其中R3为取代或未取代的芳基或取代或未取代的杂环芳基。
• Aminosalicylic-acid derivatives for the treatment of psoriasis
  申请人：DAK-LABORATORIET A/S

  公开号：EP0291159A2

  公开（公告）日：1988-11-17

  A pharmaceutical composition for use in the treatment of psoriasis comprises 4-aminosalicylic acid (4-ASA) or 5-aminosalicylic acid (5-ASA) or a functional derivative thereof, said pharmaceutical composition being in a form suitable for topical administration. Furthermore, 4-or 5-ASA or a functional derivative thereof are used for the manufacture of pharmaceutical compositions for treating psoriasis, atopic dermatitis, allergic dermatitis, contact dermatitis, seborrhoic dermatitis, or acne diseases. The derivatives have the formulae: where W is COOX, wherein X is H, Li, Na, K, Mg0.5, Ca0.5, Zn0.5, Al0.33, Fe(II)0.5, Fe(III)0.33, NH₄, NH₃R¹, NH₂R¹₂, NHR¹₃, NR¹₄, or R¹, where R¹ is substituted or unsubstituted C1-6-alkyl, aryl-C1-4-alkyl, or heteroaryl-C1-4-alkyl; or COX, where X is NR¹R1ʹ, where R1ʹ has the same meaning as R¹ defined above and R¹ and R¹ʹ may be identical or different; Y is H or R¹CO, where R¹ is defined as above; Z¹ and Z², which may be identical or non-identical are H, R¹ or R¹CO, where R¹ is defined as above, or Z¹ and Z² represent R², where R² is substituted or unsubstituted C1-6-alkylidene or aryl-C1-6-alkylidene, or heteroaryl-C1-6-alkylidene, or Z¹, Z² together with the nitrogen atom to which they are attached may represent a 3 to 7 membered saturated or unsaturated heterocyclic ring, or may represent a group of the formula - N=N-R³ where R³ is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.

  一种用于治疗牛皮癣的药物组合物包含 4-氨基水杨酸（4-ASA）或 5-氨基水杨酸（5-ASA）或其功能衍生物，所述药物组合物为适合局部用药的形式。此外，4-ASA 或 5-ASA 或其功能衍生物可用于制造治疗牛皮癣、特应性皮炎、过敏性皮炎、接触性皮炎、脂溢性皮炎或痤疮的药物组合物。这些衍生物的化学式如下 其中 W 是 COOX，其中 X 是 H、Li、Na、K、Mg0.5、Ca0.5、Zn0.5、Al0.33、Fe(II)0.5、Fe(III)0.33、NH₄、NH₃R¹、NH₂R¹₂、NHR¹₃、NR¹₄或 R¹，其中 R¹ 是取代或未取代的 C1-6-烷基、芳基-C1-4-烷基或杂芳基-C1-4-烷基；或 COX，其中 X 是 NR¹R1ʹ，其中 R1ʹ与上文定义的 R¹ 意义相同，且 R¹ 和 R¹ʹ 可以相同或不同；Y 是 H 或 R¹CO，其中 R¹ 定义如上；Z¹和Z²可以是相同或不相同的H、R¹或R¹CO，其中R¹定义如上，或者Z¹和Z²代表R²，其中R²是取代或未取代的C1-6-亚烷基或芳基-C1-6-亚烷基，或杂芳基-C1-6-亚烷基，或Z¹、Z²与所连接的氮原子一起可代表 3 至 7 个成员的饱和或不饱和杂环，或代表式 - N=N-R³ 的基团，其中 R³ 是取代或未取代的芳基或取代或未取代的杂芳基。
• US4933330A
  申请人：——

  公开号：US4933330A

  公开（公告）日：1990-06-12
• Identification of urinary metabolites of ecabapide in rat
  作者：Y. Fujimaki、T. Hosokami、K. Ono

  DOI：10.3109/00498259509061869

  日期：1995.1

  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.