246529-22-6

Usage

Uses

Used in Pharmaceutical Industry:
Aramchol is used as a therapeutic agent for the treatment of obesity, fatty liver, and insulin resistance. Its ability to suppress the activity of stearoyl-CoA desaturase (SCD) leads to a reduction in the development of these conditions, making it a promising option for patients suffering from these health issues.
Used in Research and Development:
Aramchol is also used as a research tool to study the role of stearoyl-CoA desaturase (SCD) in the development of obesity, fatty liver, and insulin resistance. This knowledge can help researchers develop new strategies and treatments for these prevalent health conditions.

Upstream product

• 506-30-9 Arachidic acid 
• 135053-61-1 methyl 3β-azido-7α,12α-dihydroxy-5β-cholan-24-oate 
• 1448-36-8 methyl cholate 
• 160836-52-2 Methyl 3α-methanesulphonyloxy-7α,12α-dihydroxy-5β-cholan-24-oate 
• 135053-62-2 (3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid methyl ester 
• 135053-65-5 3-mesylcholic acid 
• 153582-79-7 3β-aminocholic acid 
• 40140-09-8 eicosanoyl chloride 
• 81-25-4 cholic acid 
• 246529-32-8 3β-arachidamide-7α,12α-dihydroxycholic acid methyl ester 

Relevant academic research and scientific papers

Method for efficiently synthesizing Aramchol

The invention discloses a method for efficiently synthesizing Aramchol. The method comprises the following steps: firstly, generating an intermediate b-methyl cholate through esterification reaction of methanol and cholic acid molecules; reacting an alkylbenzene sulfonyl chloride with a specific structure with methyl cholate in the presence of an acid-binding agent, and selectively reacting with 3-hydroxyl of cholic acid molecules to synthesize a key intermediate c-3 alpha-O-alkylbenzene sulfonyl methyl cholate; and then protecting free hydroxyl in the intermediate c, and removing the free hydroxyl after the amidation reaction is finished, so that the problems of side reaction of acyl chloride and the free hydroxyl, serious emulsification phenomenon in the reaction process and difficulty in separation are effectively avoided.

New technology for efficiently synthesizing Aramchol by utilizing cholic acid and arachidic acid as raw materials

The invention discloses a new technology for efficiently synthesizing Aramchol by utilizing cholic acid and arachidic acid as raw materials. According to the new technology disclosed by the invention,a 3- hydroxyl group of cholic acid is activated by selecting para-butyl benzene sulfonyl chloride in larger steric hindrance and the like, 3alpha-O-para-butyl benzene sulfonyl methyl cholate, chiral3-C can be attacked by an azide group just through a direction against an alkylbenzene sulfonyloxy group of a leaving group during a nucleophilic substitution reaction process of the 3alpha-O-para-butyl benzene sulfonyl methyl cholate and sodium azide, inversion of 3-C configuration of a product-3-azido methyl cholate is ensured, and a firm foundation is laid for controlling the optical purity ofa final product-Aramchol.

Preparation methods of arachidic cholic acid and arachidic cholic acid intermediate

The invention discloses preparation methods of arachidic cholic acid and arachidic cholic acid intermediate. The preparation method of the arachidic cholic acid intermediate I provided herein includes the steps: in an organic solvent, performing reductive reaction on arachidic cholic acid intermediate II or II' and a reducing agent to obtain the arachidic cholic acid intermediate I; hydrazine hydrate or methylamine is used as the reducing agent. According to the preparation method, commercially available chemical products such as methyl cholate serve as starting materials, the arachidic cholic acid intermediate I can be prepared only by two steps, the reaction route is short, total yield can reach up to 76%, the purity of the prepared products can reach up to 98.00%, highly toxic products such as sodium azide are omitted, catalytic hydrogenation conditions are avoided, and the preparation method is safe to perform, low in production cost, environmentally friendly and suitable for industrial production.

PREPARATION METHOD FOR 3BETA-ARACHIDYLAMIDO-7ALPHA, 12ALPHA, 5BETA-CHOLAN-24-CARBOXYLIC ACID

A method for preparing 3β-arachidylamido-7α,12α,5β-cholan-24-carboxylic acid represented by the following formula V is disclosed, which includes the following steps: converting cholic acid to the compound of formula III by acylation reaction and azidation reaction, reducing the compound of formula III to the compound of formula IV and in the end acylating the compound of formula IV with arachidoyl chloride to get the compound of formula V. The method avoids the use of protection groups.

Bile salt conjugates

The present invention relates to bile acid or bile salt fatty acid conjugates (hereinafter called “BAFAC), to their use in dissolving cholesterol gallstones in bile, preventing their occurrence or recurrence, to their use in reducing or preventing arteriosclerosis and to methods for the treatment of said diseases. The conjugates are of the formula W—X—G in which G is a bile acid or bile salt radical, W stands for one or two saturated fatty acid radicals and X is either a direct bond or a bonding member between said bile acid or bile salt and the fatty acid(s). The conjugation is advantageously performed at a position selected among the 3, 6, 7, 12 and 24 positions of the bile acid or bile salt nucleus.