1-oxy-3',4',5',6'-tetrahydro-2'H-[2,4'-bipyridine]-1'-carboxylic acid tert-butyl ester | 279250-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-oxy-3',4',5',6'-tetrahydro-2'H-[2,4'-bipyridine]-1'-carboxylic acid tert-butyl ester
• 英文别名: 1-oxy-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester；2-[1-(tert-butoxycarbonyl)piperidin-4-yl]pyridinium N-oxide；Tert-butyl 4-(1-oxidopyridin-1-ium-2-yl)piperidine-1-carboxylate
• CAS: 279250-32-7
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: QRJVNEQOKQYTBN-UHFFFAOYSA-N

物化性质

• 沸点：
  455.8±38.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 储存条件：
  应存于室温、密封、干燥处。

反应信息

• 作为反应物：
  描述：

  1-oxy-3',4',5',6'-tetrahydro-2'H-[2,4'-bipyridine]-1'-carboxylic acid tert-butyl ester 在 盐酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 甲苯 为溶剂， 反应 4.75h， 生成 2-(1-{[(3-methylbenzoyl)amino]methyl}-4-piperidinyl)pyridinium N-oxide
  参考文献：
  名称：

  Discovery of 3-Methyl-N-(1-oxy-3‘,4‘,5‘,6‘-tetrahydro-2‘H-[2,4‘-bipyridine]-1‘-ylmethyl)benzamide (ABT-670), an Orally Bioavailable Dopamine D₄ Agonist for the Treatment of Erectile Dysfunction

  摘要：

  The goal of this study was to identify a structurally distinct D-4-selective agonist with superior oral bioavailability to our first-generation clinical candidate 1a (ABT-724) for the potential treatment of erectile dysfunction. Arylpiperazines such as (heteroarylmethyl) piperazine 1a, benzamide 2, and acetamides such as 3a,b exhibit poor oral bioavailability. Structure-activity relationship (SAR) studies with the arylpiperidine template provided potent partial agonists such as 4d and 5k that demonstrated no improvement in oral bioavailability. Further optimization with the (N-oxy-2-pyridinyl) piperidine template led to the discovery of compound 6b (ABT-670), which exhibited excellent oral bioavailability in rat, dog, and monkey (68%, 85%, and 91%, respectively) with comparable efficacy, safety, and tolerability to 1a. The N-oxy-2-pyridinyl moiety not only provided the structural motif required for agonist function but also reduced metabolism rates. The SAR study leading to the discovery of 6b is described herein.

  DOI：

  10.1021/jm060662k
• 作为产物：
  描述：

  3,6-二氢-2H-[2,4]联吡啶-1-羧酸叔丁基酯 在 palladium 10% on activated carbon 氢气 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 4.0h， 生成 1-oxy-3',4',5',6'-tetrahydro-2'H-[2,4'-bipyridine]-1'-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  [EN] FUSED BICYCLIC AROMATIC COMPOUNDS THAT ARE USEFUL IN TREATING SEXUAL DYSFUNCTION
  [FR] COMPOSES AROMATIQUES BICYCLIQUES CONDENSES UTILES DANS LE TRAITEMENT DE DYSFONCTIONNEMENT SEXUEL

  摘要：

  本发明涉及使用化合物(I)的治疗性功能障碍，并涉及含有化合物(I)的组合物用于治疗性功能障碍。

  公开号：

  WO2003101994A1

文献信息

• Acetamides and benzamides that are useful in treating sexual dysfunction
  申请人：——

  公开号：US20040029887A1

  公开（公告）日：2004-02-12

  The present invention relates to the use of compounds of formula (I) 1 for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式(I)的化合物治疗性功能障碍，以及含有式(I)化合物的组合物用于治疗性功能障碍。
• Fused bicyclic aromatic compounds that are useful in treating sexual dysfunction
  申请人：Cowart D. Marlon

  公开号：US20060172995A1

  公开（公告）日：2006-08-03

  The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction, wherein A, L, D and B, are as described in the specification.

  本发明涉及使用公式(I)化合物的用途，用于治疗性功能障碍，以及包含用于治疗性功能障碍的公式(I)化合物的组合物，其中A、L、D和B如说明书中所述。
• Oximes and hydrazones that are useful in treating sexual dysfunction
  申请人：Kolasa Teodzyj

  公开号：US20050176727A1

  公开（公告）日：2005-08-11

  The present invention relates to oximes and hydrazones of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及用于治疗性功能障碍的肟和腙的公式（I）化合物，以及含有用于治疗性功能障碍的公式（I）化合物的组合物。
• Fused Bicyclic Aromatic Compounds that are Useful in Treating Sexual Dysfunction
  申请人：Cowart D. Marlon

  公开号：US20070265249A1

  公开（公告）日：2007-11-15

  The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction, wherein A, L, D and B 1 are as described in the specification.

  本发明涉及使用式（I）化合物治疗性功能障碍以及含有式（I）化合物的组合物治疗性功能障碍，其中A、L、D和B1如说明书所述。
• Aminopyrrolidines as chemokine receptor antagonists
  申请人：George Dawn M.

  公开号：US20080176883A1

  公开（公告）日：2008-07-24

  The present invention is directed to novel aminopyrrolidines of formula I pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, stereoisomers thereof or pro-drugs thereof, wherein the variables are as defined herein. The compounds of formula (I) are useful as chemokine receptor antagonists and as such would be useful in treating certain conditions and diseases, especially inflammatory conditions and diseases and proliferative disorders and conditions, for example, cancers.

  本发明涉及公式I的新型氨基吡咯烷及其药学上可接受的盐、代谢物、异构体、立体异构体或前药。其中变量的定义如本文所述。公式（I）化合物可用作趋化因子受体拮抗剂，因此可用于治疗某些疾病和病症，特别是炎症性疾病和病症以及增生性疾病和病症，例如癌症。