(2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorophenyl)methanesulfonic acid L-arginine cocrystal | 813446-39-8

• 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: (2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorophenyl)methanesulfonic acid L-arginine cocrystal
• 英文别名: (5-chloro-2-{2-[4-(4-fluorobenzyl)-2R,5S-dimethylpiperazin-1-yl]-2-oxo ethoxy}-phenyl)-methanesulfonic acid (L)-arginine salt；L-Arginine, 5-chloro-2-(2-((2R,5S)-4-((4-fluorophenyl)methyl)-2,5-dimethyl-1-piperazinyl)-2-oxoethoxy)benzenemethanesulfonate (1:1)；(2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid;[5-chloro-2-[2-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-2-oxoethoxy]phenyl]methanesulfonic acid
• CAS: 813446-39-8
• 化学式: C₆H₁₄N₄O₂*C₂₂H₂₆ClFN₂O₅S
• 分子量: 659.179
• InChiKey: YDCPKICEZNHJHA-SHUTYENTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  223
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,5-dimethyl-piperazine 在 sodium tetrahydroborate 、 甲酸 、 thioacetate 、 四丁基溴化铵 、 双氧水 、 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 2-甲基四氢呋喃 、 甲醇 、 丙醇 、 环己烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 34.42h， 生成 (2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorophenyl)methanesulfonic acid L-arginine cocrystal
  参考文献：
  名称：

  Route Development and Bulk Synthesis of CP-865,569

  摘要：

  The synthesis of zwitterionic CP-865,569 by three different synthetic routes is described. The first two routes differ in the method of introducing the sulfonic acid at the penultimate step: by sulfite displacement of a benzylic chloride and by oxidation of a benzylic thioacetate. The third route is a convergent route to the drug candidate. The synthesis strategy was primarily driven by the need to introduce the sulfonic acid functionality at the final stage of the synthesis due to the high water solubility and low organic solubility of the desired product.

  DOI：

  10.1021/op7000386

文献信息

• [EN] AMORPHOUS UND CRYSTAL FORMS OF (5-CHLORO-2-{2-<br/>[FR] FORMES AMORPHES ET CRISTALLINES DE SELS DE L'ACIDE (5-CHLORO-2-{2-[4-(4-FLUORO-BENZYL)-(2R,5S)-2,5-DIMÉTHYL-PIPÉRAZIN-1-YL]-2-OXO-ÉTHOXY}-PHÉNYL)-MÉTHANE SULFONIQUE
  申请人：PFIZER PROD INC

  公开号：WO2004113311A1

  公开（公告）日：2004-12-29

  This invention relates to amorphous and crystal salt forms of (5-chloro-2-2-[4-(4-fluoro­-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy)-phenyl)-methanesulfonic acid, useful in treating or preventing a disorder or condition by antagonizing the CCR1 receptor, and to their methods of preparation and use.

  本发明涉及无定形和晶体盐形式的(5-氯-2-2-[4-(4-氟苯基)- (2R,5S)-2,5-二甲基哌嗪-1-基]-2-氧代乙氧基}-苯基)-甲磺酸，其通过拮抗CCR1受体在治疗或预防疾病或病症中有用，并且涉及其制备和使用方法。
• Salt and crystal forms of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-methanesulfonic acid
  申请人：Berliner A. Martin

  公开号：US20050119275A1

  公开（公告）日：2005-06-02

  This invention relates to salt and crystal forms of (5-chloro-2-2-[4-(4-fluorobenzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-methanesulfonic acid, useful in treating or preventing a disorder or condition by antagonizing the CCR1 receptor, and to their methods of preparation and use.

  本发明涉及(5-氯-2-2-[4-(4-氟苄基)-(2R,5S)-2,5-二甲基-哌嗪-1-基]-2-氧代-乙氧基}-苯基)-甲磺酸的盐和晶体形式，通过拮抗CCR1受体来治疗或预防疾病或病症，以及它们的制备和使用方法。
• Route Development and Bulk Synthesis of CP-865,569
  作者：Katherine Belecki、Martin Berliner、Richard Todd Bibart、Cliff Meltz、Karl Ng、James Phillips、David H. Brown Ripin、Michael Vetelino

  DOI：10.1021/op7000386

  日期：2007.7.1

  The synthesis of zwitterionic CP-865,569 by three different synthetic routes is described. The first two routes differ in the method of introducing the sulfonic acid at the penultimate step: by sulfite displacement of a benzylic chloride and by oxidation of a benzylic thioacetate. The third route is a convergent route to the drug candidate. The synthesis strategy was primarily driven by the need to introduce the sulfonic acid functionality at the final stage of the synthesis due to the high water solubility and low organic solubility of the desired product.