5beta-Chol-24-oic acid-3alpha,7beta-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 5beta-Chol-24-oic acid-3alpha,7beta-diol
• 英文别名: (4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• 化学式: C₂₄H₄₀O₄
• 分子量: 392.6
• InChiKey: RUDATBOHQWOJDD-HEGLNSLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

文献信息

• METHOD FOR PREPARING CHOLIC ACID COMPOUND
  申请人：Chia Tai Tianqing Pharmaceutical Group Co., Ltd.

  公开号：US20200347091A1

  公开（公告）日：2020-11-05

  The present application belongs to the field of pharmaceutical chemistry, and relates to a method for preparing a cholic acid compound. Specifically, the present application provides a process for preparing a compound as shown in formula I, comprising subjecting a compound of formula 2 to an oxidization reaction to obtain a compound of formula 3; attaching a trimethylsilyl group to the compound of formula 3 to obtain a compound of formula 4; reacting the compound of formula 4 with acetaldehyde to obtain a compound of formula 5; subjecting the compound of formula 5 to a catalytic hydrogenation reaction to obtain a compound of formula 6; and converting a cyano group of the compound of formula 6 to a carboxyl group to give the compound of formula I. The preparation method has high yield, requires less purification operations, and is suitable for industrial application.

  该申请属于制药化学领域，涉及一种制备胆酸化合物的方法。具体来说，该申请提供了制备式I化合物的方法，包括将式2化合物进行氧化反应得到式3化合物；将式3化合物连接三甲基硅基团得到式4化合物；将式4化合物与乙醛反应得到式5化合物；将式5化合物进行催化氢化反应得到式6化合物；将式6化合物的氰基转化为羧基得到式I化合物。该制备方法产率高，需要较少的纯化操作，适合工业应用。
• DEUTERATED BILE ACID DERIVATIVES AS FXR/TGR5 AGONISTS AND METHODS OF USE THEREOF
  申请人：ENANTA PHARMACEUTICALS, INC.

  公开号：US20170240585A1

  公开（公告）日：2017-08-24

  The present invention provides compounds of Formula (I) or Formula (II): pharmaceutical compositions comprising these compounds and methods of using these compounds to treat or prevent a disease or disorder mediated by FXR and/or TGR5.

  本发明提供了化合物的化学式(I)或化学式(II)：包括这些化合物的药物组合物以及使用这些化合物来治疗或预防由FXR和/或TGR5介导的疾病或紊乱的方法。
• METHOD FOR PREPARING BILE ACID DERIVATIVE BY USING CONTINUOUS FLOW REACTION
  申请人：DAEWOONG BIO INC.

  公开号：US20200283470A1

  公开（公告）日：2020-09-10

  Provided herein is a method of preparing a bile acid derivative using a continuous flow reaction. When bile acid derivatives are synthesized using a continuous flow reaction according to the present invention, the reaction is very safe compared to an existing batch-type reaction, the reaction time is significantly reduced, and high-quality bile acid derivatives may be synthesized with high efficiency. In particularly, according to the present invention, a hydrogenation reaction proceeds under substantially water-free reaction conditions, and thus the conversion rate (UDCA:CDCA) of a UDCA hydrogenation reaction may be significantly enhanced.

  本文提供了一种利用连续流反应制备胆酸衍生物的方法。根据本发明，当使用连续流反应合成胆酸衍生物时，与现有的批量反应相比，反应非常安全，反应时间显著缩短，并且可以高效合成高质量的胆酸衍生物。特别是根据本发明，在几乎无水的反应条件下进行氢化反应，因此可以显著提高UDCA氢化反应的转化率（UDCA:CDCA）。
• Deuterated bile acid derivatives as FXR/TGR5 agonists and methods of use thereof
  申请人：ENANTA PHARMACEUTICALS, INC.

  公开号：US10364267B2

  公开（公告）日：2019-07-30

  The present invention provides compounds of Formula (I) or Formula (II): pharmaceutical compositions comprising these compounds and methods of using these compounds to treat or prevent a disease or disorder mediated by FXR and/or TGR5.

  本发明提供了式 (I) 或式 (II) 的化合物： 包含这些化合物的药物组合物，以及使用这些化合物治疗或预防由 FXR 和/或 TGR5 介导的疾病或紊乱的方法。
• Method for bile acid derivative by using continuous flow reaction
  申请人：DAEWOONG BIO INC.

  公开号：US11053275B2

  公开（公告）日：2021-07-06

  Provided herein is a method of preparing a bile acid derivative using a continuous flow reaction. When bile acid derivatives are synthesized using a continuous flow reaction according to the present invention, the reaction is very safe compared to an existing batch-type reaction, the reaction time is significantly reduced, and high-quality bile acid derivatives may be synthesized with high efficiency. In particularly, according to the present invention, a hydrogenation reaction proceeds under substantially water-free reaction conditions, and thus the conversion rate (UDCA: CDCA) of a UDCA hydrogenation reaction may be significantly enhanced.

  本发明提供了一种利用连续流反应制备胆汁酸衍生物的方法。根据本发明，使用连续流反应合成胆汁酸衍生物时，与现有的间歇式反应相比，反应非常安全，反应时间显著缩短，并且可以高效合成高质量的胆汁酸衍生物。特别是，根据本发明，氢化反应在基本无水的反应条件下进行，因此 UDCA 氢化反应的转化率（UDCA：CDCA）可显著提高。