3-(carboxymethyl)-4-methylthiazole | 153916-38-2

• 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-(carboxymethyl)-4-methylthiazole
• 英文别名: 2-(4-Methyl-1,3-thiazol-3-ium-3-yl)acetate；2-(4-methyl-1,3-thiazol-3-ium-3-yl)acetate
• CAS: 153916-38-2
• 化学式: C₆H₇NO₂S
• 分子量: 157.193
• InChiKey: RFPDXMKDCDWESE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-carboxymethyl-4-methylthiazolium bromide 在 methyloxirane 作用下， 以 水 为溶剂， 反应 12.0h， 以78%的产率得到3-(carboxymethyl)-4-methylthiazole
  参考文献：
  名称：

  Thiazole Inner Salt Compounds, and Preparation Methods and Uses Thereof

  摘要：

  本发明涉及制药化学领域，涉及噻唑内盐化合物、其制备方法和用途。具体而言，本发明涉及一种符合式I的化合物，以及其水合物或药用可接受的盐。本发明的符合式I化合物是一种强效的交联蛋白裂解剂，具有稳定的结构、良好的物理化学性质和良好的药理活性，适用于大规模生产以获得具有稳定、可控和可靠质量的样品，从而适用于药物开发。

  公开号：

  US20160137619A1

文献信息

• Thiazole Inner Salt Compounds, and Preparation Methods and Uses Thereof
  申请人：INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY ACADEMY OF MILITARY MEDICAL SCIENCES P.L.A. CHINA

  公开号：US20160137619A1

  公开（公告）日：2016-05-19

  The present invention pertains to field of pharmaceutical chemicals, and relates to thiazole inner salt compounds, preparation methods and uses thereof. Specifically, the present invention relates to a compound of Formula I, hydrates or pharmaceutically acceptable salts thereof. The compound of Formula I of the present invention is a potent cross-linking protein cleavage agent, has a stable structure, good physical and chemical properties, and good pharmacological activities, and is suitable for large scale production to obtain samples with stable, controllable and reliable quality, thereby being suitable for pharmaceutical development.

  本发明涉及制药化学领域，涉及噻唑内盐化合物、其制备方法和用途。具体而言，本发明涉及一种符合式I的化合物，以及其水合物或药用可接受的盐。本发明的符合式I化合物是一种强效的交联蛋白裂解剂，具有稳定的结构、良好的物理化学性质和良好的药理活性，适用于大规模生产以获得具有稳定、可控和可靠质量的样品，从而适用于药物开发。
• Thiazole inner salt compounds, and preparation methods and uses thereof
  申请人：Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China

  公开号：US11180463B2

  公开（公告）日：2021-11-23

  The present invention pertains to field of pharmaceutical chemicals, and relates to thiazole inner salt compounds, preparation methods and uses thereof. Specifically, the present invention relates to a compound of Formula I, hydrates or pharmaceutically acceptable salts thereof. The compound of Formula I of the present invention is a potent cross-linking protein cleavage agent, has a stable structure, good physical and chemical properties, and good pharmacological activities, and is suitable for large scale production to obtain samples with stable, controllable and reliable quality, thereby being suitable for pharmaceutical development.

  本发明涉及医药化学品领域，涉及噻唑内盐化合物、制备方法及其用途。具体而言，本发明涉及一种式 I 的化合物、其水合物或药学上可接受的盐。本发明的式I化合物是一种强效交联蛋白裂解剂，结构稳定，理化性质好，药理活性好，适合大规模生产，获得的样品质量稳定、可控、可靠，从而适合于医药开发。
• THIAZOLE INNER SALT COMPOUNDS AND PREPARATION METHOD AND USE THEREOF
  申请人：Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L. A. China

  公开号：EP3020711B1

  公开（公告）日：2019-05-22
• THIAZOLE INNER SALT COMPOUNDS, AND PREPARATION METHODS AND USES THEREOF
  申请人：Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China

  公开号：US20190233383A1

  公开（公告）日：2019-08-01

  The present invention pertains to field of pharmaceutical chemicals, and relates to thiazole inner salt compounds, preparation methods and uses thereof. Specifically, the present invention relates to a compound of Formula I, hydrates or pharmaceutically acceptable salts thereof. The compound of Formula I of the present invention is a potent cross-linking protein cleavage agent, has a stable structure, good physical and chemical properties, and good pharmacological activities, and is suitable for large scale production to obtain samples with stable, controllable and reliable quality, thereby being suitable for pharmaceutical development.
• Novel cross-link breaker based on zwitterion structure: Synthesis, structure and druggability studies
  作者：Shuang Cao、Xin-Bo Zhou、Heng Zhang、Song Li、Wu Zhong

  DOI：10.1016/j.ejmech.2013.07.033

  日期：2013.10

  It has been universally acknowledged that the increase in cardiac and vascular stiffness is due to the formation of advanced glycosylation end-products (AGEs). Research on the stable form of 3-(carboxymethyl)-4-methylthiazol bromide sodium salt (C6H7BrNNaO2S) showed that it had a notable effect on breaking the AGEs. Two compounds with novel structures, zwitterionic 3-(carboxymethyl)-4-methylthiazol (C6H7O2NS) and a dipolymer (C12H15O4N2S2Br) complex, were obtained. When compared with the forms of sodium salt and dipolymer, zwitterion had an obvious advantage in stability, solubility, synthesis and pH, which made the zwitterion a promising drug. The structure of sodium salt, dipolymer and zwitterion was comparatively analyzed by such methods as single crystal X-ray diffraction, ESI-MS, H-1 NMR, FT-IR and in situ IR. (C) 2013 The Authors. Published by Elsevier Masson SAS. All rights reserved.