N-(2-hydroxy-5-chlorobenzoyl)-4-aminobutyric acid | 257952-20-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-hydroxy-5-chlorobenzoyl)-4-aminobutyric acid
• 英文别名: 4-[(5-Chloro-2-hydroxybenzoyl)amino]butanoic acid
• CAS: 257952-20-8
• 化学式: C₁₁H₁₂ClNO₄
• mdl: MFCD09935955
• 分子量: 257.674
• InChiKey: PBXLFIAZVDJUNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

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。
• 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。
• MANUFACTURE PROCESS OF ORGANIC COMPOUNDS
  申请人：Riss Bernhard

  公开号：US20090253811A1

  公开（公告）日：2009-10-08

  The present invention relates to a method of preparing N-substituted salicylamides or derivatives thereof, and their salts, hydrates and solvates. In particular, the present invention relates to a method of preparing N-(5-chlorosalicyloyl)-8-aminocaprylic acid (5-CNAC) and its corresponding disodium monohydrate.

  本发明涉及制备N-取代水杨酰胺或其衍生物及其盐、水合物和溶剂化合物的方法。具体而言，本发明涉及制备N-(5-氯水杨酰基)-8-氨基己酸(5-CNAC)及其相应的二钠一水合物的方法。
• DISODIUM SALTS, MONOHYDRATES, AND ETHANOL SOLVATES FOR DELIVERING ACTIVE AGENTS
  申请人：Bay William E.

  公开号：US20080269134A1

  公开（公告）日：2008-10-30

  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 wherein R 1 , R 2 , R 3 , and R 4 are independently hydrogen, halogen, C 1 -C 4 alkyl, or C 1 -C 4 alkoxy; and R 5 is a substituted 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.

  发明家发现某些传递剂的二钠盐与相应的单钠盐相比，具有更高的传递活性。此外，发明家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。这些传递剂的化学式如下：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比其相应的单钠盐和自由酸具有更高的传递活性，例如肝素和降钙素。本发明提供了上述化合物的二钠盐的醇类溶剂合物，例如乙醇溶剂合物，以及二钠盐的水合物。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]氨基)癸酸（SNAD）和N-(8-[2-羟基苯甲酰]氨基)癸酸钠盐（SNAC）。本发明还提供了制备二钠盐、醇类溶剂合物和水合物以及含有二钠盐、醇类溶剂合物和/或水合物的组合物的方法。
• Composition containing n-(5-chlorosalicyloyl)-8-aminocaprylic acid and salmon calcitonin
  申请人：Emisphere Technologies, Inc.

  公开号：EP1535625A1

  公开（公告）日：2005-06-01

  The present invention is directed to the use of a composition comprising a) N-(5-chlorosalicyloyl)-8-aminocaprylic acid, wherein N-(5-chlorosalicyloyl)-8-aminocaprylic acid comprises at least about 96% by weight of the disodium salt of N-(5-chlorosalicyloyl)-8-aminocaprylic acid; and b) salmon calcitonin, for the preparation of a medicament for orally administering salmon calcitonin to an animal.

  本发明涉及一种组合物的使用，该组合物包括 a) N-(5-氯代水杨酰)-8-氨基辛酸，其中 N-(5-氯代水杨酰)-8-氨基辛酸包含至少约 96% 的 N-(5-氯代水杨酰)-8-氨基辛酸二钠盐（按重量计）；以及 b) 鲑鱼降钙素，用于制备给动物口服鲑鱼降钙素的药物。