3-methylpiperidine-2-carboxylic acid | 147428-62-4

• 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: 3-methylpiperidine-2-carboxylic acid
• 英文别名: racemic-3-methylpiperidine-2-carboxylic acid；3-methylpiperidin-1-ium-2-carboxylate
• CAS: 147428-62-4
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: BGYDRACYCBSXEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methylpiperidine-2-carboxylic acid 在 palladium on activated charcoal 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (2S)-2-[[3-methyl-1-(3-methylbutyl)piperidine-2-carbonyl]amino]-3-(4-phenylmethoxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 4-(OBz)phenylalanine derivatives as novel N-type calcium channel blockers

  摘要：

  Selective N-type Voltage Activated Calcium Channel (VACC) blockers have shown utility in several models of stroke and pain. In the process of searching for small molecules as N-type calcium channel blockers, we have identified a series of N,N-dialkylpeptidylamines (e.g., PD 175069) with potent functional activity at N-type VACC. Further modification of the leucine moiety of PD 175069 with a cyclized ring structure provides a series of novel molecules. Syntheses and pharmacological evaluation of the series are presented. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00160-2
• 作为产物：
  描述：

  3-甲基-2-吡啶甲酸 在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 生成 3-methylpiperidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 4-(OBz)phenylalanine derivatives as novel N-type calcium channel blockers

  摘要：

  Selective N-type Voltage Activated Calcium Channel (VACC) blockers have shown utility in several models of stroke and pain. In the process of searching for small molecules as N-type calcium channel blockers, we have identified a series of N,N-dialkylpeptidylamines (e.g., PD 175069) with potent functional activity at N-type VACC. Further modification of the leucine moiety of PD 175069 with a cyclized ring structure provides a series of novel molecules. Syntheses and pharmacological evaluation of the series are presented. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00160-2

文献信息

• [EN] DESACETOXYTUBULYSIN H AND ANALOGS THEREOF<br/>[FR] DÉSACÉTOXYTUBULYSINE H ET SES ANALOGUES
  申请人：UNIV RICE WILLIAM M

  公开号：WO2016138288A1

  公开（公告）日：2016-09-01

  In one aspect, the present disclosure provides tubulysin analogs of the formula (I) wherein R1, R2, R3, R4, X1, X2, X3, and A1 are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein.

  在一个方面，本公开提供了公式（I）的tubulysin类似物，其中R1、R2、R3、R4、X1、X2、X3和A1如本文所定义。在另一个方面，本公开还提供了制备本公开化合物的方法。在另一个方面，本公开还提供了药物组合物和使用本公开化合物的方法。
• [EN] PYRAZOLO [1, 5 -A] PYRIMIDINES AS ANTIVIRAL AGENTS<br/>[FR] PYRAZOLO[1,5-A]PYRIMIDINES EN TANT QU'AGENTS ANTIVIRAUX
  申请人：GILEAD SCIENCES INC

  公开号：WO2011163518A1

  公开（公告）日：2011-12-29

  The invention provides compounds of Formula I or Formula II: (I), (II) or a pharmaceutically acceptable salt or ester, thereof, as described herein. The compounds and compositions thereof are useful for treating Pneumovirinae virus infections. The compounds, compositions, and methods provided are particularly useful for the treatment of Human respiratory syncytial virus infections.

  本发明提供了公式I或公式II的化合物：(I)、(II)或其药用可接受的盐或酯，如本文所述。这些化合物及其组合物可用于治疗副粘病毒感染。这些化合物、组合物和方法特别适用于治疗人类呼吸道合胞病毒感染。
• [EN] PYRAZOLE DERIVATIVES AS SGC STIMULATORS<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILISÉS COMME STIMULATEURS DE SGC
  申请人：IRONWOOD PHARMACEUTICALS INC

  公开号：WO2016044447A1

  公开（公告）日：2016-03-24

  There are described imidazole and pyrazole derivatives which are useful as stimulators of sGC, particularly NO-independent, heme-dependent stimulators. These compounds are also useful for treating, preventing or managing various disorders that are herein disclosed.

  描述了咪唑和吡唑衍生物，它们可作为sGC的刺激剂，特别是NO独立、依赖血红素的刺激剂。这些化合物还可用于治疗、预防或管理本文中披露的各种疾病。
• [EN] SGC STIMULATORS<br/>[FR] STIMULATEURS DE LA SGC
  申请人：IRONWOOD PHARMACEUTICALS INC

  公开号：WO2015089182A1

  公开（公告）日：2015-06-18

  The present patent application discloses at least the compounds according to Formula 1 shown below, or pharmaceutically acceptable salts thereof, wherein ringjB,n, JD, J,0, X, X1, J, RC, and W are as defined herein. These compounds are useful as simulators of soluble sGC.

  本专利申请至少揭示了如下所示的符合Formula 1的化合物，或其药用可接受盐，其中ringjB，n，JD，J，0，X，X1，J，RC和W的定义如本文所述。这些化合物可用作可溶性sGC的模拟物。
• Discovery of CYR715: A novel carboxylic acid-containing soluble guanylate cyclase stimulator
  作者：Glen R. Rennie、Timothy C. Barden、Sylvie G. Bernier、Andrew Carvalho、Renee Deming、Peter Germano、Colleen Hudson、G-Yoon J. Im、Rajesh R. Iyengar、Lei Jia、Joon Jung、Elise Kim、Thomas W.-H. Lee、Ara Mermerian、Joel Moore、Takashi Nakai、Nicholas R. Perl、Jenny Tobin、Daniel P. Zimmer、Paul A. Renhowe

  DOI：10.1016/j.bmcl.2021.127886

  日期：2021.5

  Soluble guanylate cyclase (sGC) is a clinically validated therapeutic target in the treatment of pulmonary hypertension. Modulators of sGC have the potential to treat diseases that are affected by dysregulation of the NO-sGC-cGMP signal transduction pathway. This letter describes the SAR efforts that led to the discovery of CYR715, a novel carboxylic acid-containing sGC stimulator, with an improved

  可溶性鸟苷酸环化酶（sGC）是治疗肺动脉高压的经过临床验证的治疗靶点。 sGC 调节剂具有治疗受 NO-sGC-cGMP 信号转导途径失调影响的疾病的潜力。这封信描述了导致 CYR715 发现的 SAR 工作，CYR715 是一种新型的含羧酸 sGC 刺激剂，相对于我们之前描述的刺激剂 IWP-051，其代谢特征有所改善。 CYR715解决了与相关含羧酸类似物中发现的反应性、迁移性酰基葡萄糖苷酸（AG）形成相关的潜在特殊药物毒性（IDT）倾向，并在大鼠中表现出高口服生物利用度，在血压正常的Sprague-Dawley大鼠中表现出剂量依赖性血流动力学药理学。