140375-21-9Relevant academic research and scientific papers
Crystallization engineering in aza-steroid: Application in the development of finasteride
Bhattacharya, Apurba,Manudhane, Kushal S,Maddula, Srinivasula Reddy,Sreekanth,Thota, Sridhar,Bandichhor, Rakeshwar
, p. 599 - 602 (2013)
Novel and robust crystallization approach based on solid solution formation was developed for the purification of finasteride. This is an unprecedented approach that describes the use of pure finasteride 1 to purify different lots of finasteride 1 (impure) contaminated with dihydrofinasteride 2.
Facile water mediated synthesis of finasteride form-I, an azaandrostane steroid
Rao, Divvela V. N. Srinivasa,Trinadhachari, Ganala Naga,Lenin, Racha,Prabahar, Koilpillai Joseph,Naidu, Andra,Dandala, Ramesh
, p. 121 - 124 (2007)
A simple and efficient procedure for the selective synthesis of finasteride Form-I from bis-finasteride tetrahydrofuran monohydrate solvate in good yield using ecofriendly solvent water at ambient temperature is established. Powder X-Ray diffraction data (PXRD), and Differential scanning calorimetric (DSC) data of bis-finasteride tetrahydrofuran monohydrate solvate are given.
New approach to 3-oxo-4-aza-5α-androst-1-ene-17β-(N-tert- butylcarboxamide)
Jiang, Zhong-Xing,Ye, Jing-Quan,Jiang, Li,Zhao, Ying-Sheng
, p. 690 - 693 (2005)
We describe the synthesis of 3-oxo-4-aza-5α-androst-1-ene-17β- (N-tert-butylcarboxamide) (finasteride) from 4-androstene-3,17-dione (AD) in seven steps in an overall yield of 18.6% via oxidation, ammoniumation, dehydration, and dehydrogenation.
Refining and decolorizing method of finasteride
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Paragraph 0025-0038, (2019/10/01)
The invention provides a refining and decolorizing method of finasteride. A mixed solution of sodium borohydride and a reducing sulfate is used to convert 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) residual in finasteride dehydrogenation steps into reduction-state dichlorocyano hydroquinone (DDHQ), and the DDHQ is finally converted into a salt under an alkaline condition to be removed, so that the mode that repeated solvent refining or column-chromatography decoloration is needed in a conventional process is avoided, and the product yield and production efficiency are greatly improved. Finasteride obtained by the method is a white solid, the yield can reach 93%, and the quality meets the newest pharmacopeia standard.
Method for forming double bonds between 1-position and 2-position during synthesis of finasteride and dutasteride
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, (2016/12/01)
The invention provides a method for forming double bonds between the 1-position and the 2-position during synthesis of finasteride and dutasteride. According to the process, a dihydrogen finasteride iodide and a dihydrogen dutasteride iodide are oxidized by oxone for systhesis of finasteride and dutasteride, and the method has the characteristics that reaction operation is simple and convenient, raw materials are low in price and easy to obtain, and the yield and the purity are high. In particular, oxone is non-toxic, stable, easy to operate and more suitable for large-scale industrial production, and reagents which are harmful to the environment and high in price are avoided. The method can be further applied to forming of double bonds between the 1-position and the 2-position of an intermediate in other finasteride and dutasteride processes. The invention further provides a synthesis method of dihydrogen dutasteride; according to the method, a corresponding ester raw material has a one-pot reaction with 2,5-bis(trifluoromethyl)aniline under the activation of boron tribromide, and dihydrogen dutasteride with the yield of 93% is obtained.
Impurities in finasteride: Identification, synthesis, characterization and control of potential carry-over impurities from reagents used for the process
Mohanty, Sandeep,Kumar, B. Pavan,Karmakar, Arun Chandra
, p. 4375 - 4380 (2014/08/05)
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.
TOPICAL COMPOSITIONS COMPRISING 5-ALPHA REDUCTASE INHIBITORS
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, (2010/03/31)
The present invention relates to topical compositions comprising 5α-reductase inhibitors. The present invention also includes processes for preparation of such topical compositions and methods of using them.
PROCESS FOR THE PREPARATION OF 17-N-SUBSTITUTED-CARBAMOYL-4-AZA-ANDROST-1 -EN-3-ONES
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Page/Page column 15, (2008/12/08)
The present invention relates to a process for producing 17-N-substituted-carbamoyl-4-aza-androst-1-en-3-ones of formula (1) , including Finasteride and Dutasteride.
Novel azaandrostane derivatives for the synthesis of 17β-(N-tert-butyl carbamoyl)-4-aza-5α-androst-1-ene-3-one
Srinivasa Rao, Divvela V. N.,Trinadhachari, Ganala Naga,Prabahar, Koilpillai Joseph,Dandala, Ramesh,Sivakumaran, Meenakshisundaram,Naidu, Andra
, p. 663 - 667 (2008/09/18)
(Chemical Equation Presented) A new industrially viable process for the preparation of 17β-(N-tert-butyl carbamoyl)-4-aza-5α-androst-1-ene-3- one, also known by the generic name finasteride (6) from the new azaandrostane derivatives such as 17β-(N-tert-butyl carbamoyl)-4-benzoyl-4-aza-5α- androstane-3-one (4), 17β-(N-tert-butyl carbamoyl)-4-benzoyl-4-aza- 5α-androst-1-ene-3-one (5) is reported. In this process, benzoyl group is demonstrated as a novel protecting group for lactamic NH group. The structures of newly prepared compounds were established on the basis of spectral data (IR, 1H-NMR, and MS).
PROCESSES TO PREPARE FINASTERIDE POLYMORPHS
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Page/Page column 4, (2010/11/27)
Processes for preparing polymorphic crystalline Form I and Form III of finasteride.
