137234-71-0

Usage

Uses

Used in Antifungal Therapy:
Voriconazole is used as an antifungal agent for treating a range of fungal infections, particularly invasive infections caused by Aspergillus and Candida species. It is effective in targeting various body parts, including the lungs, bloodstream, and central nervous system.
Used in Immunocompromised Patients:
Voriconazole is used as a therapeutic option for patients with compromised immune systems, such as those with HIV/AIDS or undergoing organ transplantation. Its antifungal properties help in managing fungal infections that are more likely to occur in these individuals due to their weakened immune response.

InChI:InChI=1/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3

Upstream product

• 188416-20-8 3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride salt 
• 188416-28-6 1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane 
• 137234-88-9 4-ethyl-5-fluoropyrimidine 
• 137234-85-6 2,4-dichloro-6-ethyl-5-fluoropyrimidine 
• 137234-74-3 4-chloro-6-ethyl-5-fluoropyrimidine 
• 188416-35-5 3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 906451-64-7 1-(2,4-difluorophenyl)-2-(3,5-dibromo-1H-1,2,4-triazol-1-yl)ethanone 
• 1237497-00-5 6-(1-bromoethyl)-5-fluoropyrimidin-4-yl methanesulfonate 
• 1237496-99-9 6-ethyl-5-fluoropyrimidin-4-yl methanesulfonate 
• 137234-87-8 6-ethyl-5-fluoro-4-hydroxypyrimidine 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 35963-20-3 (R)-10-camphorsulfonic acid 
• 182230-43-9 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 
• 137234-63-0 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol 

Downstream Products

• 137234-62-9 voriconazole 
• 35963-20-3 (R)-10-camphorsulfonic acid 

Relevant academic research and scientific papers

Voriconazole synthesis method

The invention relates to a voriconazole synthesis method, which comprises: 1, carrying out catalytic hydrogenation on an SM, anhydrous methanol and anhydrous sodium acetate reaction system by using palladium carbon; after treatment, crystallization is performed to obtain a voriconazole racemate; 2, the voriconazole racemate, an acetone solvent and an L(-)-camphor-10-sulfonic acid system are subjected to a reflux reaction, crystallization and filtration are performed after the reaction is completed, voriconazole camphorsulfonate is obtained, and the molar ratio of L-camphorsulfonic acid to thevoriconazole racemate is 0.5:1; and 3, adjusting the pH value of the voriconazole camphor sulfonate, dichloromethane and water system to 10-11 by using a sodium hydroxide aqueous solution, layering, and temporarily storing an organic phase; extracting the water phase with dichloromethane; and merging the organic phases, carrying out reduced pressure distillation to remove the solvent, and carryingout post-treatment to obtain voriconazole.

PROCESS FOR THE PREPARATION OF VORICONAZOLE

The present invention provides a process for preparation of racemic voriconazole in a single reaction vessel. The present invention also provides a process for preparation of voriconazole using racemic voriconazole and the process of making it therewith.

PROCESS FOR PREPARING VORICONAZOLE BY USING NEW INTERMEDIATES

Provided is a process for preparing Voriconazole represented by Chemical Formula 1. More particularly, the process for preparing Voriconazole of Chemical Formula 1 includes: carrying out the Reformatsky-type coupling reaction between a ketone derivative of Chemical Formula 4 and a pyrimidine derivative of Chemical Formula 5 to obtain a compound of Chemical Formula 3; reacting the substituents halo and oxysulfonyl with a hydrogen donor to obtain racemicVoriconazole of Chemical Formula 2; and carrying out optical isolation of the racemicVoriconazole by adding an adequate optically active acid thereto to obtain Voriconazole having high optical purity with high cost-efficiency and high yield.

PROCESS FOR THE PREPARATION OF VORICONAZOLE

The present invention relates to an improved process for the preparation of Voriconazole.

PROCESS FOR PREPARING VORICONAZOLE, NEW POLYMORPHIC FORM OF INTERMEDIATE THEREOF, AND USES THEREOF

The present invention relates to an improved process for preparation of Voriconazole and Voriconazole (1R)-(?)-10-camphorsulfonate.

IMPROVED PROCESS FOR THE PREPARATION OF (2R,3S)-2-(2,4- DIFLUQROPHENYL)-3-(5-FLUOROPYRIMIDIN-4-YL)-1-(1H-1,2,4-TRIAZOL-1-YL) BUTAN-2-OL

The present invention is directed to an improved industrially viable, cost effective process to manufacture substantially pure form of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (Voriconazole) with a chiral purity level of greater than 99.9% and impurity level of less than 0.1%.

PROCESS FOR PREPARATION OF NOVEL SALT OF VORICONAZOLE OXALATE FORM-C

The invention relates to the process of obtaining novel polymorphic form of voriconazole. Voriconozole has the chemical name (2R, 3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2-4-triazol-yl)-butan-2-ol represented as Formula (1).

Process development of voriconazole: A novel broad-spectrum triazole antifungal agent

In the synthesis of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1- yl)-2-butanol (voriconazole), the relative stereochemistry is set in the addition of a 4-(1-metalloethyl)-5-fluoropyrimidine derivative to 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-ethanone. The diastereo-control of this reaction has been examined by variation of pyrimidine substitution pattern and by changes in the metalation and reaction conditions. Excellent diastereoselection (12: 1) is obtained using an organozinc derivative of 6-(1-bromoethyl)-4-chloro-5-fluoropyrimidine. After removal of the chlorine from the pyrimidine ring, the absolute stereochemistry of voriconazole is established via a diastereomeric salt resolution process using (1R)-10-camphorsulfonic acid. Synthetic routes to the pyrimidine partner have also been evaluated. The initial six-step development route from 5-fluorouracil has been superseded by a four-step synthesis involving fluorination of methyl 3-oxopentanoate and cyclisation with formamidine acetate.