{(3S)-1-[imino-(4-methoxy-2,3,6-trimethyl-benzenesulfonylamino)-methyl]-2-oxo-piperidin-3-yl}-carbamic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {(3S)-1-[imino-(4-methoxy-2,3,6-trimethyl-benzenesulfonylamino)-methyl]-2-oxo-piperidin-3-yl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(3S)-1-[N'-(4-methoxy-2,3,6-trimethylphenyl)sulfonylcarbamimidoyl]-2-oxopiperidin-3-yl]carbamate
• 化学式: C₂₁H₃₂N₄O₆S
• 分子量: 468.574
• InChiKey: URSALMZDDCBIIP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯并噻唑 、 {(3S)-1-[imino-(4-methoxy-2,3,6-trimethyl-benzenesulfonylamino)-methyl]-2-oxo-piperidin-3-yl}-carbamic acid tert-butyl ester 、 乙基氯化镁 在 乙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到[(1S)-1-(2-benzothiazolylcarbonyl)-4-[[imino[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]methyl]amino]butyl]carbamic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Methodology for the Preparation of 2-Argininylbenzothiazole

  摘要：

  [Graphics]An efficient process to produce kilogram quantities of a key, argininylbenzo[d]thiazole intermediate was developed for the preparation of the tryptase inhibitor RWJ-56423. A variety of activated arginine esters and benzo[d]thiazole nucleophiles were evaluated as coupling partners. Our work led to the selection and optimization of an argininyl imidazolide ester and benzothiazol-2-yl MgCl nucleophile. This paper focuses on the preparation, use, and stability of the benzothiazol-2-yl Grignard reagents.

  DOI：

  10.1021/jo7019543
• 作为产物：
  描述：

  N-叔丁氧羰基-N’-(4-甲氧基-2,3,6-三甲基苯磺酰基)精氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 {(3S)-1-[imino-(4-methoxy-2,3,6-trimethyl-benzenesulfonylamino)-methyl]-2-oxo-piperidin-3-yl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Process for preparing peptidyl heterocyclic ketone derivatives

  摘要：

  本发明涉及一种新型方法，用于制备一般公式（I）中的肽杂环酮，其中所有变量如本文所定义。本发明还涉及新型药用盐和其制备方法。公式（I）中的肽杂环酮是三肽酶的强效和选择性抑制剂，可用于治疗和预防与呼吸道相关的炎症性疾病，如哮喘和过敏性鼻炎。

  公开号：

  US20050059607A1

文献信息

• Process for preparing peptidyl heterocyclic ketone derivatives
  申请人：Breslav Michael

  公开号：US20050059607A1

  公开（公告）日：2005-03-17

  The present invention relates to novel processes for the preparation of peptidyl heterocyclic ketones of the general formula (I) wherein all variables are as herein defined. The present invention further relates to novel pharmaceutical salts and processes for their preparation. The peptidyl heterocyclic ketones of formula (I) are potent and selective inhibitors of tryptase, useful for the treatment and prevention of inflammatory diseases associated with the respiratory tract, such as asthma and allergic rhinitis.

  本发明涉及一种新型方法，用于制备一般公式（I）中的肽杂环酮，其中所有变量如本文所定义。本发明还涉及新型药用盐和其制备方法。公式（I）中的肽杂环酮是三肽酶的强效和选择性抑制剂，可用于治疗和预防与呼吸道相关的炎症性疾病，如哮喘和过敏性鼻炎。
• [EN] PEPTIDYL HETEROCYCLIC KETONE DERIVATIVES AND PREPARATION PROCESSES<br/>[FR] DERIVES CETONES HETEROCYCLIQUES PEPTIDYLIQUES ET PROCEDES DE DE PREPARATION
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005023804A1

  公开（公告）日：2005-03-17

  The present invention relates to novel processes for the preparation of peptidyl heterocyclic ketones of the general formula (I) wherein all variables are as herein defined. The present invention further relates to novel pharmaceutical salts and processes for their preparation. The peptidyl heterocyclic ketones of formula (I) are potent and selective inhibitors of tryptase, useful for the treatment and prevention of inflammatory diseases associated with the respiratory tract, such as asthma and allergic rhinitis.

  本发明涉及一种制备通式（I）中所有变量如此定义的肽杂环酮的新工艺。本发明还涉及新的药物盐及其制备工艺。通式（I）中的肽杂环酮是一种有效且选择性的胰蛋白酶抑制剂，可用于治疗和预防与呼吸道有关的炎症性疾病，如哮喘和过敏性鼻炎。
• US7205384B2
  申请人：——

  公开号：US7205384B2

  公开（公告）日：2007-04-17
• Methodology for the Preparation of 2-Argininylbenzothiazole
  作者：Birdella D. Kenney、Michael Breslav、Rosie Chang、Roland Glaser、Bruce D. Harris、Cynthia A. Maryanoff、John Mills、Armin Roessler、Brigitte Segmuller、Frank J. Villani

  DOI：10.1021/jo7019543

  日期：2007.12.1

  [Graphics]An efficient process to produce kilogram quantities of a key, argininylbenzo[d]thiazole intermediate was developed for the preparation of the tryptase inhibitor RWJ-56423. A variety of activated arginine esters and benzo[d]thiazole nucleophiles were evaluated as coupling partners. Our work led to the selection and optimization of an argininyl imidazolide ester and benzothiazol-2-yl MgCl nucleophile. This paper focuses on the preparation, use, and stability of the benzothiazol-2-yl Grignard reagents.