103335-55-3

Usage

Uses

Used in Medicinal Chemistry and Pharmacology:
3-Oxo-4-aza-5-alpha-androstane-17-beta-carboxylic acid is utilized as a research compound for the development of novel pharmaceutical agents, particularly those aimed at androgen receptors. Its unique structure and potential biological activity make it a promising candidate for the treatment of various medical conditions.
Used in Hormonal Imbalance Treatment:
In the field of endocrinology, 3-Oxo-4-aza-5-alpha-androstane-17-beta-carboxylic acid is used as a potential therapeutic agent for the treatment of hormonal imbalances. Its interaction with androgen receptors may help regulate hormone levels and alleviate symptoms associated with such imbalances.
Used in Oncology Research:
3-Oxo-4-aza-5-alpha-androstane-17-beta-carboxylic acid is employed as a research tool in oncology, with a focus on the development of targeted therapies for certain types of cancer. Its specific binding to androgen receptors may offer new avenues for cancer treatment, particularly for malignancies that are influenced by hormonal regulation.
Used in Drug Development:
In the pharmaceutical industry, 3-Oxo-4-aza-5-alpha-androstane-17-beta-carboxylic acid serves as a key component in the design and synthesis of new drugs. Its unique properties and potential therapeutic effects are being investigated to create medications with improved efficacy and safety profiles for various diseases.

InChI:InChI=1/C19H29NO3/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/h11-15H,3-10H2,1-2H3,(H,20,21)(H,22,23)/t11-,12-,13-,14+,15+,18-,19+/m0/s1

Upstream product

• 76763-14-9 (3S,3aS,5aS,6R,9aS,9bS)-6-(2-carboxyethyl)-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalene-3-carboxylic acid 
• 73671-92-8 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester 
• 1416955-18-4 3,5-seco-4-norpregn-5,20-dioxo-3-(ethoxycarbonyl)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 
• 103335-54-2 (4aR,4bS,6aS,7S,9aS,9bS)-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid 

Downstream Products

• 104239-97-6 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid 
• 73671-92-8 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester 
• 142139-27-3 N-(diphenylmethyl)-3-oxo-4-aza-5α-androstane-17β-carboxamide 
• 1416955-20-8 (2α,5α,17β)-N-[2,5-bis(trifluoromethyl)phenyl]-2-iodo-3-oxo-4-aza-5-androstane-17-carboxamide 
• 1796930-46-5 dutasteride 
• 1416955-25-3 (5α,17β)-3-oxo-4-azaandrostane-17-(phenyloxycarbonyl)carboxylic acid 
• 133216-45-2 L-697818 
• 1329611-51-9 C₂₃H₃₄N₂O₂ 
• 98319-26-7 finasteride 
• 164656-22-8 (5α,17β)-N-[2,5-bis(trifluoromethyl)-phenyl]-3-oxo-4-aza-5-androstane-17-carboxamide 
• 98319-24-5 dihydro-finasteride 

Relevant academic research and scientific papers

A synthetic 3-carbonyl-4-nitrogen mixed male steroid -17 β derivative method

The invention discloses a method for synthesizing 3-carbonyl-4-azaandrost-17beta derivative I, which comprises the following steps: (1) in the presence of an acidic catalyst, dissolving A-norandrostane-3,5-cracked-androst-5-one-3-carboxylic acid-17beta derivative II in dioxane aqua ammonia, heating, and slowly and dropwisely adding reducer-dissolved aqua ammonia to simultaneously perform reduction amination reaction and ring-closing reaction; (2) adding acid to destroy the reducer, concentrating under normal pressure, and recovering dioxane; (3) cooling, and carrying out centrifugal filtration to obtain a filter cake; washing the filter cake with water to a neutral state, and carrying out centrifugal drying to obtain a 3-carbonyl-4-azaandrost-17beta derivative I crude product; and (4) pulping the 3-carbonyl-4-azaandrost-17beta derivative I crude product with methanol, carrying out centrifugal filtration to obtain a filter cake, washing the filter cake with methanol, carrying out centrifugal drying, and baking to obtain the 3-carbonyl-4-azaandrost-17beta derivative refined product. By completing the reduction amination reaction and ring-closing reaction in one step, the method has the advantages of low reaction temperature, high product yield and good product quality, is economical and environment-friendly, and is suitable for industrialization.

Impurities in finasteride: Identification, synthesis, characterization and control of potential carry-over impurities from reagents used for the process

An assessment of the impurity profile of finasteride and possible carry-over related substances likely to arise during the synthesis of finasteride is described in this article. Impurities in reaction mass were monitored by HPLC, potential impurities isolated with preparative HPLC and structures were substantiated by 1H NMR, MS and MS-MS. Impurities RRT's were established by HPLC co-injection. Based on the spectral data structure of impurity I and impurity II were characterized as cyclohexyl and phenyl analog of finasteride.

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 3-oxo-4-aza-5-alpha-androstane-17-carboxylic acid

A process for preparing the compound 3-oxo-4-aza-5α-androstane-17β-carboxylic acid having Formula (I): which is an intermediate in the preparation of 4-azasteroid drug compounds like finesteride, dutasteride, etc.

METHOD FOR THE SELECTIVE PREPARATION OF 3-OXO-4-AZA-5A-ANDROSTANE COMPOUND

This invention relates to a method for selectively preparing the 3-oxo-4-aza-5￥á-androstane compound which is used as an intermediate of finasteride by heating 3-oxo-4-aza-5-androstene in a mixture of formic acid and an alkanediol in the presence of zinc.

Azasteroids: Structure-activity relationships for inhibition of 5α-reductase and of androgen receptor binding

A series of steroids, primarily 4-azasteroids, were prepared and tested in vitro as inhibitors of human and rat prostatic 5α-reductase and of binding of dihydrotestosterone to the rat androgen receptor. The primary structural modifications were changes of the A ring and of moieties attached at the C-17 position of the steroid nucleus. New A-ring modifications included 4-cyano-3-oxoΔ4 system in the carbocyclic series and 1α-CN, 1α-CH3, 1α,2α-CH2, 2β-F, 2-aza, 2-oxa, and A-homo changes in the 3-oxo-4-aza series. In addition, 4-azasteroids with a D-homo ring or methyl substitution at C-7 (α and β) or C-16 (α and β) were prepared. The majority of the C-17 substituents were prepared from reactive intermediates derived from the 17β-COOH. Enhanced 5α-reductase inhibition in both the human and rat enzyme assays is seen with 4-CN substitution on 3-oxo-Δ4 steroids and with a C-17 side chain incorporating a lipophilically substituted semipolar group on the 4-aza-3-oxo-5α-androstane nucleus. Fewer highly active compounds were found in the human enzyme assay than in the rat assay. Structural requirements for inhibition of the rat androgen receptor are much different from those for inhibition of the enzyme. The 17β-OH moiety enhances potency more than any other feature while introduction of double bonds at C-1 or C-5 in the azasteroid gives a small improvement. Azasteroids unsubstituted at the 4-position show greatly diminished receptor activity.