4-氨基-5-乙基-1-(2-甲氧基乙基)吡唑-3-甲酰胺 | 334828-10-3

• 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
• 中文名称: 4-氨基-5-乙基-1-(2-甲氧基乙基)吡唑-3-甲酰胺
• 中文别名: 1,3-苯二甲酰胺,N,N'-二[2-羟基-1-(羟甲基)乙基]-5-[[(2R)-2-羟基-1-羰基丙基]氨基]-2,4,6-三碘-(9CI)
• 英文名称: 4-amino-3-ethyl-2-(2-methoxyethyl)pyrazole-5-carboxamide
• 英文别名: 4-amino-5-ethyl-1-(2-methoxyethyl)-1H-pyrazole-3-carboxamide；4-Amino-5-ethyl-1-(2-methoxyethyl)pyrazole-3-carboxamide
• CAS: 334828-10-3
• 化学式: C₉H₁₆N₄O₂
• 分子量: 212.252
• InChiKey: GHKYDKKHTDOYEI-UHFFFAOYSA-N

物化性质

• 沸点：
  357.9±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  4-氨基-5-乙基-1-(2-甲氧基乙基)吡唑-3-甲酰胺 在 双(三甲基硅烷基)氨基钾 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-[2-乙氧基-5-(4-乙基哌嗪-1-基磺酰基)吡啶-3-基]-3-乙基-2-(2-甲氧基乙基)-2,6-二氢-7H-吡唑并[4,3-D]嘧啶-7-酮
  参考文献：
  名称：

  The discovery of UK-369003, a novel PDE5 inhibitor with the potential for oral bioavailability and dose-proportional pharmacokinetics

  摘要：

  This paper describes our recent efforts to design and synthesise potent and selective PDE5 inhibitors and the use of in vitro predictors of clearance, absorption and permeability to maximise the potential for dose-proportional pharmacokinetics and good oral bioavailability in man. Optimisation of the preclinical profile resulted in the identification of UK-369003 (19a) and its nomination as a clinical candidate. The clinical pharmacokinetic and safety profile has enabled us to progress the compound to test its efficacy in patients with lower urinary tract symptoms (LUTS) associated with benign prostatic hyperplasia (BPH) and a paper describing its efficacy has recently been published. 2,3 (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.022
• 作为产物：
  描述：

  3-乙基-1-(2-甲氧基乙基)-4-硝基吡唑-5-甲酰胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0~25.0 ℃ 、344.75 kPa 条件下， 反应 18.0h， 生成 4-氨基-5-乙基-1-(2-甲氧基乙基)吡唑-3-甲酰胺
  参考文献：
  名称：

  The discovery of UK-369003, a novel PDE5 inhibitor with the potential for oral bioavailability and dose-proportional pharmacokinetics

  摘要：

  This paper describes our recent efforts to design and synthesise potent and selective PDE5 inhibitors and the use of in vitro predictors of clearance, absorption and permeability to maximise the potential for dose-proportional pharmacokinetics and good oral bioavailability in man. Optimisation of the preclinical profile resulted in the identification of UK-369003 (19a) and its nomination as a clinical candidate. The clinical pharmacokinetic and safety profile has enabled us to progress the compound to test its efficacy in patients with lower urinary tract symptoms (LUTS) associated with benign prostatic hyperplasia (BPH) and a paper describing its efficacy has recently been published. 2,3 (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.022
• 作为试剂：
  描述：

  2-乙氧基-5-[(4-乙基-1-哌嗪基)磺酰基]烟酸 、 4-氨基-5-乙基-1-(2-甲氧基乙基)吡唑-3-甲酰胺 在 4-氨基-5-乙基-1-(2-甲氧基乙基)吡唑-3-甲酰胺 作用下， 以94的产率得到N-[3-氨基甲酰基-5-乙基-1-(2-甲氧基乙基)吡唑-4-基]-2-乙氧基-5-(4-乙基哌嗪-1-基)磺酰基吡啶-3-甲酰胺
  参考文献：
  名称：

  Bioorg. Med. Chem. 2012, 20, 498-509

  摘要：

  DOI：

文献信息

• Crystalline therapeutic agent
  申请人：——

  公开号：US20020040140A1

  公开（公告）日：2002-04-04

  A polymorph of 1-{6-ethoxy-5-[3-ethyl-6,7-dihydro-2-(2-methoxyethyl)-7-oxo-2H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-pyridylsulfonyl}-4-ethylpiperazine.

  1-{6-乙氧基-5-[3-乙基-6,7-二氢-2-(2-甲氧基乙基)-7-氧代-2H-吡唑并[4,3-d]嘧啶-5-基]-3-吡啶磺酰基}-4-乙基哌嗪的多晶形态。
• Novel process for the preparation of pyrazoles
  申请人：——

  公开号：US20020022732A1

  公开（公告）日：2002-02-21

  A “one-pot” process is described herein for the production of pyrazole compounds of general formula (II) 1 comprising the steps of reacting a compound of general formula (III) 2 with an acylating agent in the presence of a base and an optional activating agent followed by the addition of a hydrazine compound in situ.

  本文描述了一种“一锅法”工艺，用于生产通式（II）的吡唑化合物，包括以下步骤：在碱和可选活化剂的存在下，将通式（III）的化合物与酰化剂反应，然后现场加入肼化合物。
• Pharmaceutically active compounds
  申请人：——

  公开号：US20030064990A1

  公开（公告）日：2003-04-03

  Compound of general formula I: 1 wherein R 1 , R 2 , R 3 , R 4 , X, Y and R 5 have the meanings given herein which are useful in the curative and prophylactic treatment of a medical condition for which inhibition of a cyclic guanosine 3′,5′-monophosphate phosphodiesterase (e.g. cGMP PDE5) is desired.

  通式I：1中R1、R2、R3、R4、X、Y和R5的含义如下，对于需要抑制环状鸟苷酸3′,5′-单磷酸酯酶（例如cGMP PDE5）的医疗状况的治疗和预防是有用的。
• [EN] CRYSTALLINE THERAPEUTIC AGENT<br/>[FR] AGENT THERAPEUTIQUE CRISTALLIN
  申请人：PFIZER LTD

  公开号：WO2002010171A1

  公开（公告）日：2002-02-07

  A polymorph of 1-6-ethoxy-5-[3-ethyl-6,7-dihydro-2-(2-methoxyethyl)-7-oxo-2H-pyrazolo[4,3- d]pyrimidin-5-yl]-3-pyridylsulfonyl}-4-ethylpiperazine.

  这是1-6-乙氧基-5-[3-乙基-6,7-二氢-2-(2-甲氧基乙基)-7-氧代-2H-吡唑并[4,3-d]嘧啶-5-基]-3-吡啶磺酰基}-4-乙基哌嗪的多晶形态。
• Process for the preparation of pyrazoles
  申请人：PFIZER INC.

  公开号：EP1176142A1

  公开（公告）日：2002-01-30

  There is provided a process for the production of pyrazole compounds of general formula (II): wherein RP represents H or R1; which process comprises the reaction of a compound of general formula (III), wherein R11a and R11b independently represent C1-C6 alkyl, R2 is as defined herein before, with an acylating agent in the presence of a base, followed by in situ reaction with a hydrazine compound, wherein said process is optionally carried out in the presence of an activating agent.

  提供了一种生产通式（II）的吡唑化合物的方法，其中RP代表H或R1；该方法包括通式（III）化合物的反应，其中R11a和R11b独立地代表C1-C6烷基，R2如前所定义，在碱存在下与酰化剂反应，然后在原位与肼化合物反应，其中该过程可在活化剂存在下进行。