N-(10-[2-hydroxybenzoyl]amino)decanoic acid | 183990-65-0

• 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: N-(10-[2-hydroxybenzoyl]amino)decanoic acid
• 英文别名: N-(10-[2-hydroxybenzoyl] amino)decanoic acid；N-(10-[2-hydroxybenzoyl]-amino)decanoic acid；10-(N-[2-hydroxybenzoyl]amino)decanoic acid；N-(8-[2-hydroxybenzoyl]-amino)decanoic acid；N-(10-(2-hydroxybenzoyl)amino)capricate；SNAD；10-((2-Hydroxybenzoyl)amino)decanoic acid；10-[(2-hydroxybenzoyl)amino]decanoic acid
• CAS: 183990-65-0
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: XUVPEOCUEJAFCI-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  533.9±25.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  N-(10-[2-hydroxybenzoyl]amino)decanoic acid 、 sodium hydroxide 在 氮 作用下， 以 乙醇 为溶剂， 25.0~45.0 ℃ 、13.51 MPa 条件下， 反应 0.25h， 生成 Disodium N-salicyloyl-10-aminodecanoate Ethanol
  参考文献：
  名称：

  DISODIUM SALTS, MONOHYDRATES, AND ETHANOL SOLVATES FOR DELIVERING ACTIVE AGENTS

  摘要：

  发明者们发现某些传递剂的二钠盐比相应的单钠盐具有更惊人的传递活性剂效果。此外，发明者们还发现这些传递剂的二钠盐与乙醇形成溶剂合物，与水形成水合物。传递剂的公式如下：其中R1、R2、R3和R4分别为氢、卤素、C1-C4烷基或C1-C4烷氧基；R5为取代或未取代的C2-C16烷基，取代或未取代的C2-C16烯基，取代或未取代的C1-C12烷基（芳基）或取代或未取代的芳基（C1-C12烷基）。本发明的水合物和溶剂合物也比其相应的单钠盐和自由酸具有更惊人的传递活性剂效果，例如肝素和降钙素。本发明提供了公式如上的传递剂的二钠盐的醇溶剂，例如乙醇溶剂。本发明还提供了公式如上的传递剂的二钠盐的水合物。优选的传递剂包括但不限于N-(5-氯水杨酰基)-8-氨基癸酸（5-CNAC）、N-(10-[2-羟基苯甲酰基]氨基)癸酸（SNAD）和N-(8-[2-羟基苯甲酰基]氨基)庚酸钠盐（SNAC）。本发明还提供了制备二钠盐、乙醇溶剂和水合物以及含有二钠盐、乙醇溶剂和/或水合物的组合物的方法。

  公开号：

  US20100099621A1
• 作为产物：
  描述：

  10-十一烯-1-醇 在 potassium permanganate 、 adogen 464 、 偶氮二甲酸二异丙酯 、 硫酸 、 一水合肼 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 N-(10-[2-hydroxybenzoyl]amino)decanoic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Compounds That Facilitate the Gastrointestinal Absorption of Heparin

  摘要：

  A family of novel compounds (delivery agents) that promote the gastrointestinal absorption of USP heparin in rats and primates has been discovered. The delivery agents in combination with heparin were administered either orally or intracolonically in an aqueous propylene glycol solution and caused dramatic increases in both plasma heparin concentrations (anti-Factor Xa) and clotting times (APTT). Using one of the most effective delivery agents in this series, an estimated relative bioavailability of 8% can be achieved following oral administration to cynomolgus monkeys. To establish a correlation between the in vivo data and an in vitro parameter, immobilized artificial membrane (IAM) chromatography was performed. Log relative k' values were correlated to the efficiency of oral heparin delivery.

  DOI：

  10.1021/jm970811m

文献信息

• Method of preparing alkylated salicylamides
  申请人：EMISPHERE TECHNOLOGIES, INC.

  公开号：US20020013497A1

  公开（公告）日：2002-01-31

  The present invention relates to a method of preparing an alkylated salicylamide from a protected and activated salicylamide (hereinafter referred to as a “protected/activated salicylamide”). The method comprises the steps of (a) alkylating the protected/activated salicylamide with an alkylating agent to form a protected/activated alkylated salicylamide, and (b) deprotecting and deactivating the protected/activated alkylated salicylamide, simultaneously or in any order, to form the alkylated salicylamide. The alkylated salicylamides prepared by this method are suitable for use in compositions for delivering active agents via oral or other routes of administration to animals.

  本发明涉及一种从受保护和活化的水杨酰胺（以下简称为“受保护/活化的水杨酰胺”）制备烷基化水杨酰胺的方法。该方法包括以下步骤：（a）用烷基化试剂烷基化受保护/活化的水杨酰胺，形成受保护/活化的烷基化水杨酰胺；以及（b）去保护和去活化受保护/活化的烷基化水杨酰胺，同时或以任何顺序，形成烷基化水杨酰胺。通过这种方法制备的烷基化水杨酰胺适用于用于通过口服或其他途径向动物传递活性药剂的组合物中。
• Compounds and compositions for delivering active agents
  申请人：Emishpere Technologies, Inc.

  公开号：US06346242B1

  公开（公告）日：2002-02-12

  The present invention provides a compound having the formula or a salt thereof which facilitates the delivery of active agents. Compositions and dosage unit forms comprising the compound of the present invention and at least one active agent, such as a peptide, mucopolysaccharide, carbohydrate, or a lipid, are also provided. Methods of administration and preparation of the compounds and compositions of the invention are provided as well.

  本发明提供了具有以下化学式或其盐的化合物，有助于传递活性剂。还提供了包括本发明化合物和至少一种活性剂（如肽、粘多糖、碳水化合物或脂质）的组合物和剂量单位形式。同时还提供了本发明化合物和组合物的给药方法和制备方法。
• Disodium salts, monohydrates, and ethanol solvates for delivering active agents
  申请人：Emisphere Technologies, Inc.

  公开号：US20040106825A1

  公开（公告）日：2004-06-03

  The inventors have discovered that the disodium salt of certain delivery agents has surprisingly greater efficacy for delivering active agents than the corresponding monosodium salt. Furthermore, the inventors have discovered that the disodium salts of these delivery agents form solvates with ethanol and hydrates with water. The delivery agents have the formula 1 wherein R 1 , R 2 , R 3 , and R 4 are indepedently hydrogen, halogen, C 1 -C 4 alkyl, or C 1 -C 4 alkoxy; and R 5 is a substitued or unsubstituted C 2 -C 16 alkylene, substituted or unsubstituted C 2 -C 16 alkenylene, substituted or unsubstituted C 1 -C 12 alkyl(arylene), or substituted or unsubstituted aryl(C 1 -C 12 alkylene). The hydrates and solvates of present invention also have surprisingly greater efficacy for delivering active agents, such as heparin and calcitonin, than their corresponding monosodium salts and free acids. The present invention provides an alcohol solvate, such as ethanol solvate, of a disodium salt of a delivery agent of the formula above. The invention also provides a hydrate of a disodium salt of a delivery agent of the formula above. Preferred delivery agents include, but are not limited to, N-(5-chlorosalicyloyl)-8-aminocaprylic acid (5-CNAC), N-(10-[2-hydroxybenzoyl]amino)decanoic acid (SNAD), and sodium N-(8-[2-hydroxybenzoyl]amino)caprylate (SNAC). The invention also provides methods of preparing the disodium salt, ethanol solvate, and hydrate and compositions containing the disodium salt, ethanol solvate, and/or hydrate.

  发明者发现，某些传递剂的二钠盐比相应的单钠盐具有更出色的传递活性剂的功效。此外，发明者还发现这些传递剂的二钠盐与乙醇形成溶剂合物，与水形成水合物。传递剂的公式为1，其中R1、R2、R3和R4分别为氢、卤素、C1-C4烷基或C1-C4烷氧基；R5是取代或未取代的C2-C16烷基、取代或未取代的C2-C16烯基、取代或未取代的C1-C12烷基（芳基）或取代或未取代的芳基（C1-C12烷基）。本发明的水合物和溶剂合物比它们的相应单钠盐和自由酸具有更出色的传递活性剂的功效，例如肝素和降钙素。本发明提供了公式如上的传递剂的二钠盐的醇溶剂，例如乙醇溶剂。本发明还提供了公式如上的传递剂的二钠盐的水合物。优选的传递剂包括但不限于N-(5-氯水杨酰基)-8-氨基己酸（5-CNAC）、N-(10-[2-羟基苯甲酰基]氨基)癸酸（SNAD）和N-(8-[2-羟基苯甲酰基]氨基)癸酸钠（SNAC）。本发明还提供了制备二钠盐、醇溶剂和水合物以及含有二钠盐、醇溶剂和/或水合物的组合物的方法。
• Compositions for delivering bisphosphonates
  申请人：——

  公开号：US20040147484A1

  公开（公告）日：2004-07-29

  Compounds and compositions for the delivery of bisphosphonates are provided. Methods of preparation, administration and treatment are provided as well.

  提供用于输送双磷酸盐的化合物和组合物。同时提供制备、管理和治疗的方法。
• Method of preparing alkylated salicylamides via a dicarboxylate intermediate
  申请人：Bernadino N. Joseph

  公开号：US20060084646A1

  公开（公告）日：2006-04-20

  The present invention relates to a method of preparing an alkylated salicylamide from a protected and activated salicylamide via a dicarboxylated salicylamide intermediate. The present invention also relates to dicarboxylic salicylamide delivery agent compounds for the delivery of active agents. Methods of administration are provided as well.

  本发明涉及一种从受保护和活化的水杨酰胺经过二羧基化的水杨酰胺中间体制备烷基化水杨酰胺的方法。本发明还涉及用于传递活性剂的二羧基水杨酰胺传递剂化合物。本发明还提供了给药方法。