β-(p-fluorophenyl)-γ-aminobutyric acid | 52237-19-1

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 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: β-(p-fluorophenyl)-γ-aminobutyric acid
• 英文别名: 4-amino-3-(4-fluorophenyl)butanoic acid；4-amino-3-(4-fluorophenyl)butyric acid；β-(4-fluorophenyl)-GABA；F-phenibut；d,l-4-amino-3-(4-fluorophenyl)-butyric acid
• CAS: 52237-19-1
• 化学式: C₁₀H₁₂FNO₂
• 分子量: 197.209
• InChiKey: QWHXHLDNSXLAPX-UHFFFAOYSA-N

物化性质

• 沸点：
  329.1±32.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-(p-fluorophenyl)-γ-aminobutyric acid 在 盐酸 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Krauss; Spahn; Mutschler, Arzneimittel-Forschung/Drug Research, 1988, vol. 38, # 10, p. 1533 - 1536

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-4-氨基-2-丁烯酸 、 4-fluorobenzenediazonium tetrafluoroborate 在 盐酸 、 titanium(III) chloride 作用下， 以 水 为溶剂， 反应 0.58h， 以50%的产率得到β-(p-fluorophenyl)-γ-aminobutyric acid
  参考文献：
  名称：

  Radiochemical 18F-fluoroarylation of unsaturated α-, β- and γ-amino acids, application to a radiolabelled analogue of baclofen

  摘要：

  Unsaturated alpha-, beta- and gamma-amino acids have been investigated as substrates for the reductive Meerwein arylation. Radical reactions of this type have been shown to be a valuable tool for the fast and efficient introduction of the 4-[F-18]fluorophenyl group into precursor molecules allowing short-time syntheses of potential PET radiotracers, which would be more difficult to access by other methods. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.117

文献信息

• METHOD OF MAKING 1-(ACYLOXY)-ALKYL CARBAMATE COMPOUNDS
  申请人：XENOPORT, INC.

  公开号：US20140243544A1

  公开（公告）日：2014-08-28

  Methods of preparing carbamate prodrugs of amine-containing drugs are provided. Carbonates useful in the synthesis of the carbamate prodrugs are also provided.

  提供了制备胺类药物的氨基甲酸酯前药的方法。还提供了在合成氨基甲酸酯前药中有用的碳酸盐。
• Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use
  申请人：Gallop A. Mark

  公开号：US20060111325A1

  公开（公告）日：2006-05-25

  Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, pharmaceutical compositions comprising acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, methods of making prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, methods of using prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof and pharmaceutical compositions thereof for treating or preventing diseases or disorders such as spasticity or gastroesophageal reflux disease are disclosed. Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof and sustained release oral dosage forms thereof, which are suitable for oral administration, are also disclosed.

  3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的酰氧烷基氨基甲酸酯前药，包括3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的酰氧烷基氨基甲酸酯前药的药物组合物，制备3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的前药的方法，使用3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的前药的方法，以及用于治疗或预防痉挛或胃食管反流病等疾病或紊乱的药物组合物。还公开了适用于口服的酰氧烷基氨基甲酸酯前药、3-氨基丙基膦酸、3-氨基丙基膦酸和其类似物的持续释放口服剂型。
• Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use
  申请人：Gallop A. Mark

  公开号：US20060111439A1

  公开（公告）日：2006-05-25

  Acyloxyalkyl carbamate prodrugs of 3-aminopropylsulfinic acid and analogs thereof, pharmaceutical compositions of 3-aminopropylsulfinic acid and analogs thereof, methods of making prodrugs of 3-aminopropylsulfinic acid and analogs thereof, methods of using prodrugs of 3-aminopropylsulfinic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing diseases or disorders such as spasticity or gastroesophageal reflux disease are disclosed. Acyloxyalkyl carbamate prodrugs of 3-aminopropylsulfinic acid and analogs thereof and sustained release oral dosage forms thereof, which are suitable for oral administration, are also disclosed.

  3-氨基丙磺酸及其类似物的酰氧烷基氨基甲酸酯前药，3-氨基丙磺酸及其类似物的药物组合物，制备3-氨基丙磺酸及其类似物的前药的方法，使用3-氨基丙磺酸及其类似物的前药的方法，以及用于治疗或预防痉挛性或胃食管反流病等疾病或紊乱的药物组合物已被披露。此外，还披露了适用于口服的3-氨基丙磺酸及其类似物的酰氧烷基氨基甲酸酯前药和持续释放口服剂型。
• METHODS OF TREATING FRAGILE X SYNDROME, DOWN'S SYNDROME, AUTISM AND RELATED DISORDERS
  申请人：Wustrow David J.

  公开号：US20120016021A1

  公开（公告）日：2012-01-19

  Disclosed herein are methods of treating fragile X syndrome, fragile X-associated tremor/ataxia syndrome, Down's syndrome and other forms of mental retardation, and/or autism comprising administering a GABA B agonist prodrug to a subject suffering therefrom. The GABA B agonist prodrugs can be compounds of Formula (I), (II) or (III) as disclosed herein.

  本文披露了治疗脆性X综合症、脆性X相关性震颤/共济失调综合症、唐氏综合症和其他形式智力障碍和/或自闭症的方法，包括向患者施用GABAB受体激动剂前药。GABAB受体激动剂前药可以是公式(I)、(II)或(III)中所披露的化合物。
• Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
  申请人：Gallop A. Mark

  公开号：US20050107334A1

  公开（公告）日：2005-05-19

  The disclosures herein relate generally to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, pharmaceutical compositions thereof, methods of making prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, methods of using prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing common diseases and/or disorders such as spasticity and/or acid reflux disease. The disclosures herein also relate to acyloxyalkyl carbamate prodrugs of (±)-4-amino-3-(4-chlorophenyl)butanoic acid and analogs thereof which are suitable for oral administration and to sustained release oral dosage forms thereof.

  本文涉及的内容通常与(±)-4-氨基-3-(4-氯苯基)丁酸及其类似物的酰氧基烷基氨基甲酸酯前药、其制药组合物、制备(±)-4-氨基-3-(4-氯苯基)丁酸及其类似物的前药的方法、使用(±)-4-氨基-3-(4-氯苯基)丁酸及其类似物的前药的方法，以及治疗或预防常见疾病和/或疾病，如痉挛和/或酸反流病的制药组合物。本文还涉及适用于口服和口服缓释剂型的(±)-4-氨基-3-(4-氯苯基)丁酸及其类似物的酰氧基烷基氨基甲酸酯前药。