3α-hydroxy-7-keto-cholanic acid | 28332-54-9

• 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: 3α-hydroxy-7-keto-cholanic acid
• 英文别名: 3a-Hydroxy-7-ketocholanic acid；(4R)-4-[(3R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 28332-54-9
• 化学式: C₂₄H₃₈O₄
• 分子量: 390.563
• InChiKey: DXOCDBGWDZAYRQ-DVTFWNRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3α-hydroxy-7-keto-cholanic acid 、 四氢呋喃 、 、 氨 、 锂 在 氨 、 水 、 Be hydrochloric acid 、 乙酸乙酯 、 乙醇 作用下， 以 甲醇 为溶剂， 反应 2.25h， 以to obtain 104 g of crystalline crude 3α,7β-dihydroxy-cholanic acid with a specific rotation of [α]D20 =+50°±1° (c=1% in ethanol)的产率得到ursodeoxychlic acid
  参考文献：
  名称：

  Process for the production of ursodesoxycholic acid

  摘要：

  一种改进的方法，通过在液氨中用锂还原3.alpha.-羟基-7-酮基-胆酸，高产地制备熊去氧胆酸或3.alpha.，7.beta.-双羟基-胆酸。

  公开号：

  US04425274A1

文献信息

• [EN] METHODS FOR PREPARATION OF BILE ACIDS AND DERIVATIVES THEREOF<br/>[FR] PROCÉDÉS DE PRÉPARATION D'ACIDES BILIAIRES ET DE LEURS DÉRIVÉS
  申请人：INTERCEPT PHARMACEUTICALS INC

  公开号：WO2017019524A1

  公开（公告）日：2017-02-02

  The present application relates to a method of preparing compounds of Formula (I) or a pharmaceutically acceptable salt, solvate, or amino acid conjugate thereof, R1 is H, α-OH, β-ΟΗ, or an oxo group.

  本申请涉及一种制备化合物I的方法或其药学上可接受的盐、溶剂化合物或氨基酸结合物的方法，其中R1为H、α-OH、β-OH或氧基团。
• [EN] PROCESS FOR PREPARING HIGH PURITY URSODEOXYCHOLIC ACID<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACIDE URSODÉSOXYCHOLIQUE DE PURETÉ ÉLEVÉE
  申请人：ERREGIERRE SPA

  公开号：WO2014020024A1

  公开（公告）日：2014-02-06

  The present invention describes a process for the synthesis of ursodeoxycholic acid wherein the purification of the crude ursodeoxycholic acid (containing approximately 13-15% of chenodeoxycholic acid impurity) takes place first passing through a salification with imidazole and a subsequent purification via "methyl ester", which allows a finished product with an extremely low content of known "cheno and "litho" impurities to be obtained. The present invention also describes the recovery steps of cholic acid and 3α-hydroxy-7-ketocholanic acid from the mother liquors of process intermediates.

  本发明描述了一种合成熊去氧胆酸的过程，其中对粗熊去氧胆酸（含约13-15%的石胆酸杂质）的纯化首先通过咪唑盐化和随后的“甲酯”纯化进行，从而得到含有极低“石胆”和“磷胆”杂质的成品。本发明还描述了从过程中间体的母液中回收胆酸和3α-羟基-7-酮胆酸的步骤。
• 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）。
• NOVEL METHOD OF SYNTHESIZING ALKYLATED BILE ACID DERIVATIVES
  申请人：Yu Donna D.

  公开号：US20090062526A1

  公开（公告）日：2009-03-05

  A novel, improved method of synthesizing alkylated bile acid derivatives is provided. Such derivatives include, but are not limited to the active, potent, and selective FXR receptor agonist such as 6-ECDCA and other CA, DCA and CDCA derivatives. The first step of the synthesis selectively oxidates CDCA, CD, or DCA related starting material. An efficient combined deprotonation, trapping, ethylation, deprotection and reduction system is used to produce the desired alkylated bile acid derivatives. This practical synthesis offers a simple and economical pathway suitable for a large-scale manufacturing of alkylated bile acid derivatives including, but not limited to, 6-ECDCA.

  提供了一种新颖的合成烷基化胆酸衍生物的方法。这些衍生物包括但不限于活性、有效和选择性的FXR受体激动剂，如6-ECDCA和其他CA、DCA和CDCA衍生物。合成的第一步是选择性氧化CDCA、CD或DCA相关的起始物质。采用高效的联合去质子化、捕获、乙基化、去保护和还原系统来生产所需的烷基化胆酸衍生物。这种实用的合成方法提供了一条简单经济的途径，适用于大规模生产烷基化胆酸衍生物，包括但不限于6-ECDCA。
• [EN] AN IMPROVED PROCESS FOR PREPARATION OF OBETICHOLIC ACID<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION D'ACIDE OBÉTICHOLIQUE
  申请人：ALEMBIC PHARMACEUTICALS LTD

  公开号：WO2018220513A1

  公开（公告）日：2018-12-06

  The invention relates to an improved process for the preparation of compound of formula (A), which is an intermediate in the preparation of Obeticholic acid or its analogous compounds thereof.

  该发明涉及一种改进的制备化合物(A)的方法，该化合物是制备Obeticholic酸或其类似化合物的中间体。