(+/-)-Pivalopril | 93132-64-0

• 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: (+/-)-Pivalopril
• 英文别名: N-Cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1-oxopropyl]glycine；(DL)-[N-(3-trimethylacetylthio-2-methylpropanoyl)-N-(cyclopentyl)glycine]；Pivalopril；2-[cyclopentyl-[3-(2,2-dimethylpropanoylsulfanyl)-2-methylpropanoyl]amino]acetic acid
• CAS: 93132-64-0
• 化学式: C₁₆H₂₇NO₄S
• 分子量: 329.461
• InChiKey: XRKXJJYSKUIIEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(3-mercapto-2-methyl propanoyl)-N-cyclopentyl glycine-t-butyl ester 在 碘代三甲硅烷 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (+/-)-Pivalopril
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives

  摘要：

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00379a013

文献信息

• Prodrug derivatives of acids using alcohols with homotopic hydroxy groups and methods for their preparation and use
  申请人：deLong A. Mitchell

  公开号：US20070254920A1

  公开（公告）日：2007-11-01

  This invention relates to novel homotopic prodrugs and medicaments and methods for their preparation, testing and use. In one embodiment, the homotopic prodrug has the general formula wherein is a biologically-active moiety comprising a carboxylic acid functional group, and R b is a homotopically-symmetrical alcohol bonded to the biologically-active moiety through the carboxylic acid functional group to form an ester linkage, as well as optical isomers, enantiomers, pharmaceutically acceptable salts, biohydrolyzable amides, esters, and imides thereof and combinations thereof.

  这项发明涉及新型同位素前药、药物以及其制备、测试和使用方法。在一个实施例中，同位素前药具有一般公式 其中 是包含羧酸官能团的生物活性基团，而 R b 是通过羧酸官能团与生物活性基团形成酯键的同位对称醇，以及其光学异构体、对映异构体、药用可接受盐、生物水解酰胺、酯、亚酰胺及其组合物。
• Bile-acid derived compounds for enhancing oral absorption and systemic bioavailability of drugs
  申请人：——

  公开号：US20030130246A1

  公开（公告）日：2003-07-10

  Disclosed are compounds that exhibit high transport across the intestinal wall of an animal. The compounds may optionally be linked to drugs that are poorly absorbed or poorly transported across the intestinal wall after oral administration to provide for enhanced therapeutic, and optionally prolonged therapeutic, systemic blood concentrations of the drugs upon oral administration of the drug-compound conjugate. Also disclosed are pharmaceutical compositions containing and methods of using such compounds.

  本文披露了一种在动物肠壁上具有高透过性的化合物。这些化合物可以选择性地与那些口服后吸收或透过肠壁运输效果不佳的药物结合，以提高药物-化合物共轭物口服后的治疗效果，并在口服药物-化合物共轭物时实现药物在全身血液中的浓度增加，可选择性地延长药物的治疗效果。还披露了含有这些化合物的药物组合物及使用这些化合物的方法。
• Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof
  申请人：——

  公开号：US20030171303A1

  公开（公告）日：2003-09-11

  The present invention provides a method for synthesizing 1-(acyloxy)-alkyl derivatives from 1-acyl-alkyl derivatives, which typically proceeds stereospecifically, in high yield, does not require the use of activated intermediates and/or toxic compounds and is readily amenable to scale-up. The current invention also provides 1-acyl-alkyl derivatives of known drug compounds and methods for synthesizing these 1-acyl-alkyl derivatives.

  本发明提供了一种从1-酰基-烷基衍生物合成1-(酰氧基)-烷基衍生物的方法，该方法通常具有立体特异性，产率高，不需要使用活化中间体和/或有毒化合物，并且易于扩大生产规模。本发明还提供了已知药物化合物的1-酰基-烷基衍生物以及合成这些1-酰基-烷基衍生物的方法。
• Ophthamological drugs
  申请人：Toone J. Eric

  公开号：US20060135609A1

  公开（公告）日：2006-06-22

  The present invention relates generally to ophthamological drugs. More specifically, the inventon relates to a method of modifying (derivatizing) ophthamological drugs so as to increase their penetration through the cornea. The invention also relates to drugs modified (derivatized) in accordance with the instant method and to the use of same in treating conditions associated with elevated intraocular pressure, particularly, glaucoma.

  本发明一般涉及眼科药物。更具体地，本发明涉及一种修改（衍生化）眼科药物的方法，以增加它们通过角膜的渗透性。本发明还涉及根据本方法修改（衍生化）的药物，以及将其用于治疗与眼内压升高相关的疾病，特别是青光眼。
• Compounds for sustained release of orally delivered drugs
  申请人：——

  公开号：US20020098999A1

  公开（公告）日：2002-07-25

  Disclosed are methods for providing sustained systemic blood concentrations of orally delivered drugs. Still further, disclosed are compounds and pharmaceutical compositions that are used in such methods.

  揭示了提供口服药物持续系统血浆浓度的方法。此外，还揭示了在这些方法中使用的化合物和药物组合物。