67372-69-4

Usage

Uses

Used in Pharmaceutical Industry:
6,7-DeMethylene-6,7-dehydro Drospirenone is used as an intermediate in the synthesis of Drospirenone for the following reasons:
1. It contributes to the production of Drospirenone, a hormone with various pharmaceutical applications, including contraception and hormone replacement therapy.
2. As an impurity, it helps in the quality control and assurance of the final product, ensuring the safety and efficacy of Drospirenone-based medications.
3. Its presence in the synthesis process allows for the optimization of the production method, potentially leading to more cost-effective and efficient manufacturing of Drospirenone.

Upstream product

• 889676-41-9 17-hydroxy-15β,16β-methylene-3-oxo-17α-pregna-4,6-diene-21,21-dicarboxyIic acid ethyl ester γ-lactone 
• 82543-15-5 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one 
• 943434-07-9 3-ethoxy-15β,16β-methylene-17α-pregn-3,5-diene-21,17-carbolactone 
• 108664-95-5 (3S,5R,8R,9S,10R,13S,14S,15S,16S,17S)-17-(3-Hydroxy-propyl)-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16,17,20-tetradecahydro-2H-cyclopropa[15,16]cyclopenta[a]phenanthrene-3,5,17-triol 
• 108674-97-1 17α-(3-hydroxypropynyl)-15β,16β-methylene-5β-androst-6-ene-3β,5,17β-triol 

Downstream Products

• 89948-36-7 Mespirenone 
• 84542-26-7 7α-(methoxycarbonyl)-15β,16β-methylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone 
• 889652-31-7 17-hydroxy-6α,7α;15β,16β-bismethylene-3-oxo-17α-pregn-4-ene-21,21-carboxyIic acid γ-lactone 
• 90457-65-1 dihydrospirorenone 

Relevant academic research and scientific papers

Epoxidation of 17-oxo-15,16-methylene steroids with sulfoxonium ylides

A process for the epoxidation of 17-oxo-15,16-methylene steroids, in particular of drospirenone precursors, comprising the use of sulfoxonium ylides, in particular of dimethylsulfoxonium methyl ylide. The process allows to prepare in good yields 17-spiro epoxides, which can be easily transformed into 17-spironolacto-steroids.

Epoxidation of 17-oxo-15,16-Methylene Steroids with Sulfoxonium Ylides

A process for the epoxidation of 17-oxo-15,16-methylene steroids, in particular of drospirenone precursors, comprising the use of sulfoxonium ylides, in particular of dimethylsulfoxonium methyl ylide. The process allows to prepare in good yields 17-spiro epoxides, which can be easily transformed into 17-spironolacto-steroids.

A PROCESS FOR THE PREPARATION OF 17-HYDROXY-6β,7β;15β,l6β-BISMETHYLENE-17α-PREGN-4-ENE-3-ONE-21-CARBOXYLIC ACID γ-LACTONE AND KEY-INTERMEDIATES FOR THIS PROCESS

The invention relates to a process for the preparation of 17-hydroxy-6β,7β;15β,16β- bismethylene-17α-pregn-4-ene-3-one-21-carboxylic acid γ-lactone of formula (I) as well as to key- intermediates for this process.

Aldosterone antagonists. 2. New 7α-(acetylthio)-15,16-methylene spirolactones

Some 15,16-methylene derivatives of the aldosterone antagonist spironolactone (1) were synthesized with the purpose of increasing the antialdosterone potency and reducing the endocrinological effects of this standard compound. By introduction of a 1,2-double bond and a 15β,16β-methylene ring in the spironolactone molecule both goals were achieved. In animal studies mespirenone (13) exhibited a threefold-greater antiandosterone potency and less than 10% of the antiandrogenic activity of spironolactone.