104239-97-6

Usage

InChI:InChI=1/C19H27NO3/c1-18-9-7-13-11(12(18)4-5-14(18)17(22)23)3-6-15-19(13,2)10-8-16(21)20-15/h8,10-15H,3-7,9H2,1-2H3,(H,20,21)(H,22,23)/t11-,12-,13-,14+,15+,18-,19+/m0/s1

Upstream product

• 67-56-1 methanol 
• 103335-41-7 methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate 
• 75-09-2 dichloromethane 
• 21149-38-2 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide 
• 504-02-9 1,3-cylohexanedione 
• 103335-55-3 3-oxo-4-aza-5α-androstane-17β-carboxylic acid 
• 98319-26-7 finasteride 
• 1416955-18-4 3,5-seco-4-norpregn-5,20-dioxo-3-(ethoxycarbonyl)carboxylate 
• 149198-45-8 methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate 
• 3510-20-1 3,5-seco-4-norpregn-5,20-dion-3-carboxylic acid 
• 57-83-0 Progesterone 
• 73711-89-4 3,20-dioxo-4-aza-5α-pregnane 
• 1416955-23-1 C₂₀H₃₁NO₃ 
• 20283-95-8 3,20-dioxo-4-aza-pregnan-5-ene 

Downstream Products

• 103497-68-3 23-methyl-4-aza-21-nor-5α-chol-1-ene-3,20-dione 
• 98319-26-7 finasteride 
• 133216-44-1 17β-(cyclohexylcarbonyl)-4-aza-5α-androst-1-ene-3-one 
• 133216-45-2 L-697818 
• 142139-60-4 N-[1-methyl-1-(4-methoxyphenyl)ethyl]-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide 
• 1796930-46-5 dutasteride 
• 103335-41-7 methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate 

Relevant academic research and scientific papers

A scaleable synthesis of dutasteride: A selective 5α-reductase inhibitor

An improved and scaleable process for Dutasteride (1), a synthetic 4-azasteroid derivative essentially used for the treatment of prostate diseases, is described

Isolation and structural characterization of degradation products of finasteride by preparative HPLC, HRMS and 2D NMR

Finasteride is a 5-α-reductase inhibitor with a steroidal skeleton and an amide group in its structure. It was subjected to forced degradation to observe its stability under stress conditions according to ICH guidelines. It was found to be stable to base and peroxide. However, in acid medium, three degradation products were observed. All of them were isolated from the reaction mixture by preparative HPLC. Their structures were elucidated by extensive analysis of 1D, 2D NMR spectra and HRMS. To best of our knowledge, none of them have been reported elsewhere.

Production process of high-purity dutasteride

The invention discloses a purification production process of high-purity dutasteride. The problems to be solved are that the purity of the dutasteride is improved while the production cost is reduced.According to the method, after a dutasteride crude product is obtained, twice crystallization is carried out, so that the dutasteride with high yield and high purity can be obtained. The production process provided by the invention has the advantages of high efficiency and clean production, and the operability is high. An intermediate is refined, so that the quality of the dutasteride finished product is more easily controlled, the purity of the obtained dutasteride product is not lower than 99.5%, and any single impurity in the product is not higher than 0. 1%.

PROCESS FOR THE SYNTHESIS OF (5α,17β)-N-[(2,5-BIS(TRIFLUOROMETHYL)-PHENYL]-3-OXO-4-AZA-5-ANDROST-1-ENE-17-CARBOXAMIDE

The synthesis consists of reaction steps as follows: oxidizing the α,β-unsaturated ketone system of ring "A" of pregn-4-ene-3,20-dion- of formula (II) with sodium metaperiodate in tert-butanol in the presence of potassium permanganate and alkali metal carbonate, reacting the obtained 3,5-seco acid with an ester of chloroformic acid in the presence of tertier organic base below 0°C, reacting the obtained new compound after isolation or without isolation with ammonia or ammonium acetate, cyclization of the resulting carboxamides with an acid, cathalytic hydrogenating the obtained ene lactame, and oxidizing the side chain at position 17 of the obtained pregnane compound with an alkali metal hypobromide in aqueous dioxane below 10°C. Thereafter on one hand the obtained (5α,17β)-3-oxo-4-aza-5-androstane-17-carboxylic acid is reacted with chloroformic acid ester, the obtained new compound is reacted with 2,5-bis(trifluoromethyl)-aniline in the presence of a Lewis acid, the obtained amide is reacted with trimethyl chlorosilane in inert atmosphere in the presence of Ν,Ν,Ν',Ν'-tetramethyl-ethylendiamine, then en excess iodine is added to the reaction mixture and the product of the iodination reaction is crystallized from acetonitrile, then the obtained 2-iodo-3-oxo-4-aza-17β-carboxamide is reacted with potassium tert-butylate to furnish final product. On the other hand, (5α,17β)-3-oxo-4-aza-5-androstane-17-carboxylic acid is transformed into methylester by known method, this latter is transformed into methyl (2α,5α,17β)-2-iodo-3-oxo-4-aza-5-androstane-17-carboxylate according to known method, the obtained compound is reacted with potassium-tert-butylate, the obtained (5α,17β)-3-oxo-4-aza-5-androst-1-ene-17-carboxylic acid is reacted with an ester of chloroformic acid, then the obtained new compound is coupled with 2,5-bis(trifluoromethyl)-aniline in the presence of a Lewis acid catalyst to gain final product.

PROCESS FOR PREPARING ANDROSTENONE DERIVATIVES

Provided is a process for preparing androstenone derivatives, specifically 3-oxo-4-aza-5α-androstene-17β-carboxylic acid of Formula I, a key intermediate for dutasteride.

Process for the preparation of 17beta-N-[2,5-bis(trifluoromethyl)phenyl] carbamoyl-4-aza-5-alpha-androst-1-en-3-one

The present invention relates to a process for the preparation of Dutasteride, which is chemically known as 17β-N-[2,5-bis (trifluoromethyl) phenyl] carbamoyl-4-aza-5-α-androst-1-en-3-one and can be represented by Formula (I).

Dehydrogenation process intermediates

A process for dehydrogenating a compound of the formula STR1 which comprises reacting the compound with a silylating agent in the presence of a quinone to introduce a Δ1 double bond.

Dehydrogenation process

A process for dehydrogenating a compound of the formula STR1 which comprises reacting the compound with a silylating agent in the presence of a quinone to introduce a Δ1 double bond.

Dehydrogenation process and intermediates

A process for dehydrogenating a compound of the formula which comprises reacting the compound with a silylating agent in the presence of a quinone to introduce aΔ1 double bond. Novel intermediates are compounds of the formula wherein:, Q is absent or is where R4 is methyl, C1 8 straight or branched chain alkyl, C3 6 cycloalkyl, phenyl, or combinations thereof; and R14 is hydrogen, C1 6 alkyl, C1 6 straight or branched chain alkoxy, halo, nitro or cyano.