E 352 | 177653-18-8

• 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: E 352
• 英文别名: 4-[4-[(2-Hydroxybenzoyl)amino]phenyl]butyric acid；4-[4-[(2-hydroxybenzoyl)amino]phenyl]butanoic acid
• CAS: 177653-18-8
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: CTSNJCQIDJAIJL-UHFFFAOYSA-N

物化性质

• 沸点：
  440.5±35.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-氨基苯基)丙酸 、 E 352 在 sodium hydroxide 作用下， 反应 2.5h， 生成 3-[4-[(2-Hydroxybenzoyl)amino]phenyl]propanoic acid
  参考文献：
  名称：

  4-[4-[(2-Hydroxybenzoyl)amino]phenyl]butyric Acid as a Novel Oral Delivery Agent for Recombinant Human Growth Hormone

  摘要：

  A series of N-acetylated, non-alpha, aromatic amino acids was prepared and shown to promote the absorption of recombinant human growth hormone (rhGH) from the gastrointestinal tract. Seventy compounds in this family were tested in vivo in rats. Of the compounds tested, 4-[4-[(2-hydroxybenzoyl)amino]phenyl]butyric acid was identified as a preclinical candidate and was used to demonstrate the oral delivery of rhGH in primates. A significant positive correlation was found between the relative log k' of the delivery agents, as determined by HPLC on an immobilized artificial membrane (IAM) column, and serum rhGH concentrations following oral or colonic dosing in rats. Structure-activity relationships have also been developed on the basis of electronic effects and hydrogen-bonding characteristics of the aromatic amide substituents.

  DOI：

  10.1021/jm960038f
• 作为产物：
  描述：

  邻乙酰水杨酰氯 在 sodium hydroxide 、 三乙胺 作用下， 反应 4.0h， 生成 E 352
  参考文献：
  名称：

  4-[4-[(2-Hydroxybenzoyl)amino]phenyl]butyric Acid as a Novel Oral Delivery Agent for Recombinant Human Growth Hormone

  摘要：

  A series of N-acetylated, non-alpha, aromatic amino acids was prepared and shown to promote the absorption of recombinant human growth hormone (rhGH) from the gastrointestinal tract. Seventy compounds in this family were tested in vivo in rats. Of the compounds tested, 4-[4-[(2-hydroxybenzoyl)amino]phenyl]butyric acid was identified as a preclinical candidate and was used to demonstrate the oral delivery of rhGH in primates. A significant positive correlation was found between the relative log k' of the delivery agents, as determined by HPLC on an immobilized artificial membrane (IAM) column, and serum rhGH concentrations following oral or colonic dosing in rats. Structure-activity relationships have also been developed on the basis of electronic effects and hydrogen-bonding characteristics of the aromatic amide substituents.

  DOI：

  10.1021/jm960038f

文献信息

• Oral GLP-1 Formulations
  申请人：Sarubbi Donald J.

  公开号：US20100016229A1

  公开（公告）日：2010-01-21

  The present invention provides pharmaceutical compositions comprising of at least one delivery agent and GLP-1. These pharmaceutical compositions facilitate the oral delivery of GLP-1, providing improved (e.g. increased) bioavailability of GLP-1 compared to administration of GLP-1 without a delivery agent.

  本发明提供了包含至少一种传递剂和GLP-1的药物组合物。这些药物组合物促进了GLP-1的口服给药，相比于没有传递剂的GLP-1给药，提高了GLP-1的生物利用度（例如，增加了生物利用度）。
• Pharmaceutical compositions of peptides having low solubility in physiological medium
  申请人：Applied Research Systems ARS Holding N.V.

  公开号：EP0880968A1

  公开（公告）日：1998-12-02

  Pharmaceutical compositions are described, which comprise: a) a peptide poorly soluble in aqueous physiological saline solution, as active ingredient; b) a non-ionic aromatic hydrotropic pharmaceutically acceptable agent; and c) a physiological aqueous solution.

  描述了药物组合物，其中包括：a) 作为活性成分的一种难溶于生理盐水水溶液的多肽；b) 一种非离子芳香族亲水药剂；以及 c) 生理水溶液。
• Method for administering GLP-1 molecules
  申请人：Emisphere Technologies, Inc.

  公开号：EP2409569A2

  公开（公告）日：2012-01-25

  The invention encompasses formulations that demonstrate the feasibility of oral absorption comprising GLP-1 compounds and specified delivery agents.

  本发明包括能证明口服吸收 GLP-1 化合物和特定给药剂可行性的制剂。
• Methods and compositions for inducing oral tolerance in mammals
  申请人：——

  公开号：US20020061311A1

  公开（公告）日：2002-05-23

  The present invention relates to methods and pharmaceutical formulations for orally delivering an antigen to induce tolerance. The antigen is combined with derivatized amino acids or salts thereof. The induction of oral tolerance may be applied clinically for the prevention or treatment of auto-immune diseases and clinical allergic hypersensitivities, and for the prevention of allograft rejection.

  本发明涉及口服递送抗原以诱导耐受的方法和药物制剂。抗原与衍生氨基酸或其盐结合。诱导口服耐受性可应用于临床，预防或治疗自身免疫性疾病和临床过敏性超敏反应，以及预防同种异体移植排斥反应。
• Solution Phase Preparation of Highly Pure Amide Mixtures via In-Situ Chlorotrimethylsilane Protection and Activation
  作者：Koc-Kan Ho、Nai Fang Wang、Christine Lercara、Doris C. O'Toole、Douglas M. Achan、Edmund A. Vuocolo、Andrea Leone-Bay

  DOI：10.1080/00397919708004209

  日期：1997.3

  Coupling of 4-(4-aminophenyl)butyric acid 1 with acyl halides in both organic and aqueous media were found to produce large amount of oligomeric materials. By using an in situ chlorotrimethylsilane protection/activation procedure, these oligomers were suppressed completely and the desired 4-(4-acylaminophenyl)butyric acids 3 were obtained in good yield and high purity. The method was also extended to a parallel synthesis of a three component mixture. H-1-NMR of the mixture indicated that each component was formed in a nearly stoichiometric quantity.