915038-26-5

Usage

Uses

Used in Digestive Health Applications:
3α-hydroxy-6-ethyl-7-keto-5β-cholan-24-oic acid is used as a digestive aid for promoting the emulsification and absorption of dietary fats. It facilitates the formation of micelles, which are essential for the absorption of fat-soluble vitamins and other lipid-soluble nutrients, thereby contributing to overall digestive health.
Used in Pharmaceutical Industry:
3α-hydroxy-6-ethyl-7-keto-5β-cholan-24-oic acid is used as a therapeutic agent for the treatment of liver and gastrointestinal disorders. Its potential therapeutic properties make it a valuable compound for developing medications to address various liver and gastrointestinal conditions.
Used in Nutritional Supplements:
3α-hydroxy-6-ethyl-7-keto-5β-cholan-24-oic acid can be used as an ingredient in nutritional supplements to support healthy digestion and absorption of fats and fat-soluble vitamins. Its role in micelle formation can help improve the bioavailability of these nutrients, promoting overall health and well-being.

Upstream product

• 863239-59-2 3α-hydroxy-6-ethylidene-7-keto-5β-cholan-24-carboxylic acid methyl ester 

Downstream Products

• 1537866-42-4 6α-ethyl-3α-formyloxy-7-keto-5β-cholan-24-oic acid 
• 865244-30-0 (3α,5β,6α,7β)-6-ethyl-3,7-dihydroxycholan-24-oic acid 

Relevant academic research and scientific papers

3β-Isoobeticholic acid efficiently activates the farnesoid X receptor (FXR) due to its epimerization to 3α-epimer by hepatic metabolism

Bile acids (BAs) are important signaling molecules acting via the farnesoid X nuclear receptor (FXR) and the membrane G protein-coupled bile acid receptor 1 (GPBAR1). Besides deconjugation of BAs, the oxidoreductive enzymes of colonic bacteria and hepatocytes enable the conversion of BAs into their epimers or dehydrogenated forms. Obeticholic acid (OCA) is the first-in-class BA-derived FXR agonist approved for the treatment of primary biliary cholangitis. Herein, a library of OCA derivatives, including 7-keto, 6-ethylidene derivatives and 3β-epimers, was synthetized and investigated in terms of interactions with FXR and GPBAR1 in transaction assays and evaluated for FXR target genes expression in human hepatocytes and C57BL/6 mice. The derivatives were further subjected to cell-free analysis employing in silico molecular docking and a TR-FRET assay. The conversion of the 3βhydroxy epimer and its pharmacokinetics in mice were studied using LC–MS. We found that only the 3β-hydroxy epimer of OCA (3β-isoOCA) possesses significant activity to FXR in hepatic cells and mice. However, in a cell-free assay, 3β-isoOCA had about 9-times lower affinity to FXR than did OCA. We observed that 3β-isoOCA readily epimerizes to OCA in hepatocytes and murine liver. This conversion was significantly inhibited by the hydroxy-Δ5-steroid dehydrogenase inhibitor trilostane. In addition, we found that 3,7-dehydroobeticholic acid is a potent GPBAR1 agonist. We conclude that 3β-isoOCA significantly activates FXR due to its epimerization to the more active OCA by hepatic metabolism. Other modifications as well as epimerization on the C3/C7 positions and the introduction of 6-ethylidene in the CDCA scaffold abrogate FXR agonism and alleviate GPBAR1 activation.

AN IMPROVED PROCESS FOR THE PREPARATION OF OBETICHOLIC ACID AND INTERMEDIATES USED IN THE PROCESS THEREOF

The present invention relates to an improved process for the preparation of Obeticholic acid and intermediates used in the process thereof. The invention also relates to a solid form of tertiary butylamine salt of Obeticholic acid and tertiary butylamine salt of Obeticholic acid in the solvate form.

Preparation method of obeticholic acid

The invention relates to a preparation method of obeticholic acid, in particular to a compound shown as a formula III which is described in the specification, a preparation method of the compound anda method for preparing obeticholic acid through the compound III. The method has the advantages of mild reaction conditions, few byproducts, simplicity and convenience in operation, high total yield and the like, and is suitable for large-scale production.

Compound for treating metabolic diseases as well as preparation method and application thereof

The invention provides a compound for treating metabolic diseases, the compound has a structure represented by formula (I) or formula (II), or a racemate, a stereoisomer, a geometric isomer, a tautomer, a solvate, a hydrate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof. The compounds provided by the invention are FXR and/or TGR5 receptor activators, and the compounds havethe activity of activating FXR and/or TGR5 receptors, and can be used for preparing medicines for treating chronic liver diseases, metabolic diseases or portal hypertension.

Process Research and Impurity Control Strategy for Obeticholic Acid, a Farnesoid X Receptor Agonist

The process to obtain ICH-grade quality obeticholic acid (OCA) was improved, and the overall yield was 25.9%. The critical process parameters were established to reduce or avoid process-related impurities. The formation mechanisms, purge pathways, and control strategies for these impurities were also discussed for the first time. An high-performance liquid chromatography instrument utilizing the charged aerosol detection technique was applied for an impurity content assay in OCA for the first time. The developed process was robust and suitable for manufacturing scale-up.

Synthesis method of obeticholic acid and intermediate

The invention discloses a synthesis method of obeticholic acid and an intermediate. The method specifically comprises seven steps: an oxidation reaction, an esterification reaction, a protection reaction, an Aldol reaction, hydrogenation reduction, hydrolysis and a carbonyl reduction reaction with raw materials including chenodeoxycholic acid, NBS, concentrated sulfuric acid, methanol, sodium iodide, trimethyl silicon chloride, trimethylamine, acetaldehyde, boron trifluoride diethyl etherate, palladium on carbon, hydrogen, NaOH and NaBH4. The synthesis method of obeticholic acid and the intermediate is high in yield, low in cost, environmentally friendly, easy to operate and suitable for industrialization.

STEROID DERIVATIVE FXR AGONIST

The present invention relates to a compound represented by formula (I), a tautomer thereof or a pharmaceutically acceptable salt thereof, and relates to applications thereof in the preparation of drugs for treating FXR related diseases.

Sulfonylurea derivative and pharmaceutical composition and application thereof

The invention relates to a preparation method and application of a sulfonylurea compound and a composition containing the same component as FXR and / or TGR5 agonist, the FXR and / or TGR5 agonist is a compound shown as a formula (I), or a pharmaceutically acceptable salt, a solvate, a prodrug, an isomer and a stable isotope derivative thereof. The compounds can be used for treatment of FXR and / or TGR5 mediated diseases including primary biliary cirrhosis, nonalcoholic fatty liver, portal hypertension, bile acid diarrhea and cholestasis, type II diabetes and obesity and other field.

METHODS OF PROMOTING HEPATIC REGENERATION

The present invention relates to methods of accelerating, promoting or increasing hepatic regeneration, or increasing liver mass in a subject, by using a compound of formula (A): or a pharmaceutically acceptable salt thereof, and wherein R1, R2, R3, R4, R5, R6, m, and n are as described herein.

Process for preparing aobeiAobei cholic acid (by machine translation)

The invention application discloses a process for preparing aobeiAobei cholic acid, includes the following steps: AB - 1 — AB - 2 — AB - 3 — AB - 4 — AB - 5 — AB - 6 — AB - 7 — AB - 8 — AB - 9 — AB - 10, the preparation process in the process of preparing a simple and highly efficient reaction conditions, so as to ensure that the quality of the final product aobeiAobei cholic acid can be controlled. (by machine translation)