FIELD: chemistry.
SUBSTANCE: invention relates to improved methods of producing 6-methyleneandrost-4-ene-3,17-dione and 6-methyleneandrost-1,4-diene-3,17-dione (MNN exemestane) using the obtained 6-methyleneandrost-4-ene-3,17-dione. 6-methyleneandrost-4-ene-3,17-dione is obtained using a method involving preliminary enolisation of Δ4-3-ketofunction of androst-4-ene-3,17-dione with formation of 3-alkoxyandrost-3,5-dien-17-one, subsequent three-component condensation with a secondary amine and formaldehyde in the medium of a polar protonic solvent, deamination of the N,N-disubstituted amino group to form a 6-methylene group in the medium of an aprotic solvent. 6-methyleneandrost-1,4-diene-3,17-dione is obtained through 1,2-dehydrogenation of 6-methyleneandrost-4-ene-3,17-dione via microbiological transformation in a medium containing up to 40% water-miscible aprotic solvent using Nocardioides simplex cells VKM As-2033D.
EFFECT: high output and selectivity under mild conditions for carrying out the process.
11 cl, 4 ex, 1 tbl
| Title | Year | Author | Number |
|---|---|---|---|
| MICROBIOLOGICAL METHOD OF PRODUCING 1,2-DEHYDROGENATED DERIVATIVES OF Δ-3-KETO-STEROIDS OF ANDROSTANE FAMILY IN AQUEUS ORGANIC MEDIA | 2010 |
|
RU2447154C1 |
| METHOD OF OBTAINING 11BETA, 17 ALPHA, 21-TRIHYDROXY-16ALPHA-METHYL-9ALPHA-FLUOROPREGNA-1,4-DIENE-3,20-DIONE (DEXAMETHAZONE) FROM PHYTOSTEROL | 2013 |
|
RU2532902C1 |
| MICROBIOLOGICAL METHOD OF PRODUCING 21-ACETOXYPREGNA-1,4,9( 11 ),16-TETRAENE-3,20-DIONE FROM 21-ACETOXYPREGNA-4,9( 11 )16-TRIENE-3,20-DIONE | 2011 |
|
RU2480475C1 |
| METHOD OF PRODUCING 1,2-DEHYDRODERIVATIVES OF 4-DELTA-3-KETO-STEROIDS | 1998 |
|
RU2156302C1 |
| N-SUBSTITUTED DERIVATIVES OF 6α-PIPERAZINOMETHYLANDROOST-4-EN-3,17-DIONE, HAVING ANTIMICROBIAL ACTIVITY, AND THEIR PRODUCTION METHOD | 2023 |
|
RU2807924C1 |
| METHOD OF OBTAINING ANDROST-4,9(11)-DIEN-3,17-DIONE FROM PHYTOSTEROL | 2012 |
|
RU2512076C1 |
| METHOD OF PRODUCING 3β-ACETOXY-17α-HYDROPEROXY-16α-METHYLPREGNANES FROM Δ-20-KETOSTEROIDS AND METHOD OF PRODUCING 3β-ACETOXY-17α-HYDROXY-16α-METHYLPREGNANES USING 3β-ACETOXY-17α-HYDROPEROXY-16α-METHYLPREGNANES | 2009 |
|
RU2418805C1 |
| METHOD OF OBTAINING 6α-METHYLHYDROCORTISONE OR ITS 11β-ALKANOYLOXY-DERIVATIVES (VERSIONS), METHOD OF OBTAINING 6α-METHYLPREDNISOLONE OR ITS 11β-ALKANOYLOXY-DERIVATIVES USING OBTAINED 6α-METHYLHYDROCORTISONE OR ITS 11β-ALKANOYLOXY-DERIVATIVES | 2006 |
|
RU2337918C9 |
| METHOD OF SYNTHESIS OF γ-LACTONE 3 OF (7α-ACETYLTHIO-17β-HYDROXY-3-OXOANDROST-4-ENE-17α-YL)-PROPIONIC ACID | 1999 |
|
RU2163606C1 |
| METHOD OF 9-ALPHA-HYDROXYANDROST-4-ENE-3,17-DIONE PREPARING | 1994 |
|
RU2077590C1 |
