192704-58-8

Basic information

• Product Name: 5,pregnane-7 alpha,21-dicarboxylic acid,17-ydroxy-11-methylsulfonic acid-3-ketone,-butyrolectone,methyl ester cas:(intermediate of eplerenone)
• Synonyms: 5,pregnane-7 alpha,21-dicarboxylic acid,17-ydroxy-11-methylsulfonic acid-3-ketone,-butyrolectone,methyl ester cas:(intermediate of eplerenone);5,PREGNANE-7 ALPHA,21-DICARBOXYLIC ACID,17-YDROXY-11-METHYLSULFONIC ACID-3-KETONE,-BUTYROLECTONE,METHYL ESTER;Eplerenone intermediate A2-2;methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone
• CAS NO: 192704-58-8
• Molecular Formula: C₂₅H₃₄O₈S
• Molecular Weight: 494.6
• Product Categories: (intermediate of eplerenone)
• Mol File: 192704-58-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,pregnane-7 alpha,21-dicarboxylic acid,17-ydroxy-11-methylsulfonic acid-3-ketone,-butyrolectone,methyl ester cas:(intermediate of eplerenone)(CAS DataBase Reference)
• NIST Chemistry Reference: 5,pregnane-7 alpha,21-dicarboxylic acid,17-ydroxy-11-methylsulfonic acid-3-ketone,-butyrolectone,methyl ester cas:(intermediate of eplerenone)(192704-58-8)
• EPA Substance Registry System: 5,pregnane-7 alpha,21-dicarboxylic acid,17-ydroxy-11-methylsulfonic acid-3-ketone,-butyrolectone,methyl ester cas:(intermediate of eplerenone)(192704-58-8)

Safety Data

• Hazardous Substances Data: 192704-58-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5,pregnane-7 alpha,21-dicarboxylic acid,17-hydroxy-11-methylsulfonic acid-3-ketone,-butyrolectone,methyl ester CAS (intermediate of eplerenone) is used as a key intermediate in the synthesis of eplerenone for the treatment of high blood pressure and heart failure. It plays a crucial role in the development of this medication due to its ability to block the effects of aldosterone, a hormone that regulates fluid and electrolyte balance in the body, thus helping to manage blood pressure and improve heart function.

Upstream product

• 192704-56-6 11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone 
• 124-63-0 methanesulfonyl chloride 
• 1398078-03-9 11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone 
• 1398078-09-5 11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone 
• 209253-72-5 9α,11α-epoxy-17β-hydroxypregn-4-en-3-one-7α,21-dicarboxylic acid γ-lactone 
• 192569-17-8 11α-hydroxyl canrenone 

Downstream Products

• 95716-70-4 17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester 
• 192704-70-4 7-methyl hydrogen 17α-hydroxy-3-oxopregna-4,11-diene-7α,21-dicarboxylate, γ-lactone 
• 107724-20-9 eplerenone 

Relevant articles and documents

Preparation method of eplerenone intermediate delta 9, 11 alkenyl ester

The invention provides a preparation method of eplerenone intermediate delta 9, 11 alkenyl ester, and the method comprises the following steps: carrying out esterification reaction on raw materials and methanesulfonyl chloride to generate methanesulfonate; and carrying out elimination reaction on the methanesulfonate to obtain an eplerenone intermediate; the method has the advantages that the process yield is about 90%, and the product purity is obviously higher than that reported in the existing literature. The delta 11, 12-alkenyl ester generated in the method has the advantages of fewer lactone impurities and high yield, and the method is an economic and environment-friendly synthetic route, greatly improves the prior art, and is suitable for industrial production.

Synthesis and physicochemical characterization of the process-related impurities of eplerenone, an antihypertensive drug

Two unknown impurities were observed during the process development for multigram-scale synthesis of eplerenone (Inspra). The new process-related impurities were identified and fully characterized as the corresponding (7β,11α,17α)-11-hydroxy- and (7α,11β,17α) -9,11-dichloroeplerenone derivatives 12a and 13. Seven other known but poorly described in the literature eplerenone impurities, including four impurities A, B, C and E listed in the European Pharmacopoeia 8.4 were also detected, identified and fully characterized. All these contaminants result from side reactions taking place on the steroid ring C of the starting 11α-hydroxy-7α-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone (12) and the key intermediate (7α,17α)-9(11)-enester 7, including epimerization of the C-7 asymmetric center, oxidation, dehydration, chlorination and lactonization. The impurities were isolated and/or synthesized and fully characterized by infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectrometry/electrospray ionization (HRMS/ESI). Their 1H- and 13C-NMR signals were fully assigned. The molecular structures of the eight impurities, including the new (7β,11α,17α)-11-hydroxy- and (7α,11β,17α)-9,11-dichloroeplerenone related substances 12a and 13, were solved and refined using single-crystal X-ray diffraction (SCXRD). The full identification and characterization of these impurities should be useful for the quality control and the validation of the analytical methods in the manufacture of eplerenone.

A steroid compound derivative having, its preparation process and its use in the preparation of Eplerenone

The invention relates to a canrenone derivative steroid compound, a preparation method and an application in the medicine field, and particularly relates to 7alpha-nitro methyl-11alpha,17beta-dihydroxy-3-oxo-17alpha-pregna-4-ene-21-carboxylic acid-gamma-lactone (a compound shown in formula 2), a preparation method and an application in eplerenone preparation. The key steps of the invention are that nitromethane is used as a nucleophilic reagent; the alpha-nitro methyl group is introduced to the C-7 position stereoselectively so as to further construct a carboxylic acid methyl ester structure with a C-7alpha position configuration of eplerenone; the method of the invention has the characteristics of short steps, mild conditions, and low cost.

A diastereoselective synthesis of 7α-nitromethyl steroid derivative and its use for an efficient synthesis of eplerenone

A novel and efficient method of stereoselectively introducing α-nitromethyl group to C-7 position of 11α-hydroxyl canrenone 4 was described. In addition, this method was successfully applied in a total synthesis of Eplerenone 8. The route was characteristic of simple operation, moderate reaction conditions with 5 steps and 55% total yield, at the same time, without any expensive or toxic reagent in use.

A chemobiological synthesis of eplerenone

This paper will describe an approach to the synthesis of eplerenone, which is being marketed for the treatment of hypertension. The synthesis begins with DHEA available from wild yams and uses a combination of microbiological and chemical transformations to build eplerenone. Georg Thieme Verlag Stuttgart.

Processes for preparing C-7 substituted steroids

This invention relates to processes for the preparation of novel 7-carboxy substituted steroid compounds of Formula I,

Processes for preparation of 3-keto-7alpha-alkoxycarbonyl-delta-4,5- steroids and intermediates useful therein

Multiple novel reaction schemes, novel process steps and novel intermediates are provided for the synthesis of epoxymexrenone and other compounds of Formula I wherein:-A-A- represents the group -CHR4-CHR5- or -CR4=CR5- R3, R4 and R5 are independently selected from the group consisting of hydrogen, halo, hydroxy, lower alkyl, lower alkoxy, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, cyano, varyloxy;R1 represents an alpha-oriented lower alkoxycarbonyl or hydroxyalkyl radical;-B-B- represents the group -CHR6-CHR7- or an alpha- or beta- oriented group: where R6 and R7 are independently selected from the group consisting of hydrogen, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy; andR8 and R9 are independently selected from the group consisting of hydrogen, hydroxy, halo, lower alkoxy, acyl, hydroxyalkyl, alkoxyalkyl, hydroxycarbonyl, alkyl, alkoxycarbonyl, acyloxyalkyl, cyano and aryloxy, or R8 and R9 together comprise a carbocyclic or heterocyclic ring structure, or R8 or R9 together with R6 or R7 comprise a carbocyclic or heterocyclic ring structure fused to the pentacyclic D ring.