(S)-afoxolaner | 1096103-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-afoxolaner
• 英文别名: esafoxolaner；Esafoxolaner；4-[(5S)-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxamide
• CAS: 1096103-99-9
• 化学式: C₂₆H₁₇ClF₉N₃O₃
• 分子量: 625.878
• InChiKey: OXDDDHGGRFRLEE-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.8
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  4-[3-[3-chloro-5-(trifluoromethyl)phenyl]-4,4,4-trifluoro-1-oxo-2-buten-1-yl]-N-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide 在 C₄₈H₄₉N₂O₅⁽¹⁺⁾*Cl^(1-) 、 羟胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 以83.6%的产率得到(S)-afoxolaner
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED ISOXAZOLINE COMPOUNDS - CRYSTALLINE TOLUENE SOLVATE OF (S)-AFOXOLANER
  [FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS D'ISOXAZOLINE ÉNANTIOMÉRIQUEMENT ENRICHIS ET DE SOLVATE DE TOLUÈNE CRISTALLIN DE (S)-AFOXOLANER

  摘要：

  这项发明涉及使用奎宁基手性相转移催化剂制备富含一个对映体的抗寄生虫异噁唑烷化合物的过程。该发明还涉及新型奎宁基相转移催化剂以及(S)-氧氟咪唑的结晶甲苯溶剂化合物形式。

  公开号：

  WO2017176948A1

文献信息

• [EN] PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED ISOXAZOLINE COMPOUNDS - CRYSTALLINE TOLUENE SOLVATE OF (S)-AFOXOLANER<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS D'ISOXAZOLINE ÉNANTIOMÉRIQUEMENT ENRICHIS ET DE SOLVATE DE TOLUÈNE CRISTALLIN DE (S)-AFOXOLANER
  申请人：MERIAL INC

  公开号：WO2017176948A1

  公开（公告）日：2017-10-12

  This invention relates to processes for the preparation of antiparasitic isoxazoline compounds enriched in an enantiomer using quinine- based chiral phase transfer catalysts. The invention also relates to novel quinine-based phase transfer catalysts and to a crystalline toluene solvate form of (S)-afoxolaner.

  这项发明涉及使用奎宁基手性相转移催化剂制备富含一个对映体的抗寄生虫异噁唑烷化合物的过程。该发明还涉及新型奎宁基相转移催化剂以及(S)-氧氟咪唑的结晶甲苯溶剂化合物形式。
• ANTIPARASITIC ISOXAZOLINE COMPOUNDS, LONG-ACTING INJECTABLE FORMULATIONS COMPRISING THEM, METHODS AND USES THEREOF
  申请人：MERIAL INC.

  公开号：US20170239218A1

  公开（公告）日：2017-08-24

  This invention relates to long-acting injectable compositions for combating parasites in animals, comprising at least one isoxazoline active agent, a liquid PEG and/or a neutral oil, optionally a co-solvent, and optionally a pharmaceutically acceptable additive or excipient. This invention also provides new isoxazoline active agents with long-lasting efficacy against ectoparasites. The invention also provides for improved methods for eradicating, controlling, and preventing parasite infections and infestations in an animal comprising administering the novel isoxazoline compounds and long-acting injectable compositions of the invention to the animal in need thereof.

  该发明涉及一种用于对抗动物寄生虫的长效注射剂组合物，包括至少一种异唑啉类活性剂、液态PEG和/或中性油、可选的共溶剂以及可选的药用添加剂或赋形剂。该发明还提供了新的异唑啉类活性剂，具有长效抗外寄生虫的功效。该发明还提供了改进的方法，用于根除、控制和预防动物寄生虫感染和寄生，包括向需要该组合物的动物注射该发明的新异唑啉类化合物和长效注射剂组合物。
• Process for the preparation of isoxazoline compounds
  申请人：MERIAL INC.

  公开号：US10433552B2

  公开（公告）日：2019-10-08

  This invention relates to processes for the preparation of antiparasitic isoxazoline compounds enriched in an enantiomer using quinine-based chiral phase transfer catalyst. The invention also relates to novel quinine-based phase transfer catalysts and to a toluene solvent form of the isoxazoline compound of the invention.

  本发明涉及使用基于奎宁的手性相转移催化剂制备富含对映体的抗寄生虫异噁唑啉化合物的工艺。本发明还涉及新型奎宁基相转移催化剂和本发明异噁唑啉化合物的甲苯溶剂形式。
• Long-acting injectable formulations comprising an isoxazoline active agent, methods and uses thereof
  申请人：BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

  公开号：US10561641B2

  公开（公告）日：2020-02-18

  This invention relates to long-acting injectable formulations for combating parasites in animals, comprising at least one isoxazoline active agent, a poloxamer, and a co-solvent. This invention also provides for improved methods for eradicating, controlling, and preventing parasite infections and infestations in an animal comprising administering the long-acting injectable formulations of the invention to the animal in need thereof.

  本发明涉及用于防治动物体内寄生虫的长效注射制剂，该制剂包括至少一种异噁唑啉活性剂、一种聚氧乙烯醚和一种助溶剂。本发明还提供了根除、控制和预防动物体内寄生虫感染和侵扰的改进方法，包括向需要的动物施用本发明的长效注射制剂。
• Crystalline forms of (S)-afoxolaner
  申请人：BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

  公开号：US10662163B2

  公开（公告）日：2020-05-26

  The present invention provides crystalline forms of compound of formula (Ia) and processes of making the crystalline forms. Also provided are compositions comprising the crystalline forms and methods of use of the crystalline forms

  本发明提供了式(Ia)化合物的结晶形式以及结晶形式的制造工艺。本发明还提供了包含结晶形式的组合物和结晶形式的使用方法