- Process development of voriconazole: A novel broad-spectrum triazole antifungal agent
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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 The initial six-step development route from 5-fluorouracil has been superseded by a four-step synthesis involving fluorination of methyl 3-oxopentanoate and cyclisation with formamidine acetate.
- Butters, Mike,Ebbs, Julie,Green, Stuart P.,MacRae, Julie,Morland, Matthew C.,Murtiashaw, Charles W.,Pettman, Alan J.
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Read Online
- Voriconazole synthesis process
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The invention discloses a synthesis process of voriconazole bulk drug, which comprises the following steps: preparing halogenated ethyl fluorouracil and carrying out Grignard reaction. 2 - (2, 4 - Difluorophenyl) -3 - (1, 2, 4 - triazol -1 -yl) -1, 2 - propylene glycol was oxidized to give a propylene oxide compound. The Grignard reagent and the propylene oxide compound are mixed and reacted to obtain voriconazole. To the synthesis process, the reaction steps can be simplified, the dehydrochlorination and hydrogenolysis of palladium carbon are not needed, the reaction period is shortened, and furthermore, the energy consumption is reduced, the cost is reduced, and voriconazole and the racemate thereof are obtained with higher yield.
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- Improved voriconazole racemate preparation method
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The invention relates to an improved voriconazole racemate preparation method. The method comprises the following steps: (1) reacting 2 '4'-difluoro-2-[1- (1H-1, 2, 4-triazolyl)] acetophenone with 4-(1-bromoethyl)-5-fluoro-6-chloropyrimidine in the presence of zinc powder, lead powder and iodine to prepare R, S/S and R-1; (2) in the presence of a palladium-carbon catalyst and under a heating condition, taking R, S/S, R-1 or a salt thereof as a reaction substrate to react with ammonium formate in a reaction solvent to prepare a voriconazole racemate reaction solution; and filtering the reactionsolution, collecting a filtrate, carrying out concentrating, adding water, adjusting the pH value of the solution to 7-9, stirring, filtering, collecting a filter cake, and drying to obtain the product; and (3) splitting the voriconazole racemate by using 1R-(-)- camphorsulfonic acid to prepare the voriconazole. According to the preparation method, alkali degradation is avoided, and impurities are reduced; meanwhile, the preparation method does not need to treat R, S/S and R-1 hydrochloride, direct reaction can be carried out, meanwhile, post-treatment does not need operations such as extraction, and the preparation method has the advantages of being simple and convenient to operate, safe, controllable, high in reproducibility, high in product yield, high in purity, low in cost, suitablefor industrial production and the like.
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Paragraph 0077-0081
(2020/12/31)
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- Voriconazole synthesis method
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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.
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Paragraph 0011; 0048; 0076-0091
(2020/08/02)
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- Synthesis method of voriconazole and intermediate of voriconazole
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The invention relates to a synthesis method of voriconazole and an intermediate of voriconazole. The synthesis method comprises the following step: in a protective gas atmosphere, reacting a compoundshown in formula I and a compound shown in formula II in an organic solvent under the action of a metal catalyst, N-heterocyclic carbene, samarium diiodide and elemental iodine to obtain the voriconazole intermediate shown in formula III. According to the synthesis method of the voriconazole intermediate, under the action of the metal catalyst and SmI2, N-heterocyclic carbene is simultaneously added as a ligand, and elemental iodine is used as an initiator to initiate a reformask coupling reaction between the compound shown in formula I and the compound shown in formula II, so that the defectsof low yield, more byproducts and the like of the traditional reaction are overcome, and the yield and the purity are further improved.
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- A preparation method of Voriconazole
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The invention relates to a preparation method for voriconazole. The preparation method comprises the following steps: 1) a compound A is reacted with D-camphor-10-sulfonyl chloride as shown in the description to obtain a compound B; 2) the compound B is brominated to obtain a compound C; 3) the compound C and a compound 5 are subjected to condensation to obtain a compound 6; 4) the compound is subjected to palladium-carbon catalytic hydrogenation to obtain the voriconazole. According to the prepared method, the synthesis method is simple, the three-dimensional selectivity is high, raw materials are easy to obtain, and the cost is low.
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Paragraph 0041; 0042; 0043
(2017/08/25)
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- Preparation method of voriconazole
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The invention discloses a preparation method of voriconazole, which includes the steps of: dissolving a compound B in a solvent, controlling the temperature of the reaction liquid to be -70 - 0 DEG C, stirring the reaction liquid, adding alkali with stirring and controlling the temperature of the reaction liquid to be -70 - 0 DEG C, stirring the reaction liquid, dropwise adding a mixed liquid of A and a solvent, and after the mixed liquid is added completely, controlling the temperature of the reaction liquid to be -70 - 0 DEG C to perform a reaction for 2-48 h to obtain the compound (1). In the process, a required chiral configuration is introduced from the raw material A, so that the method has high stereoselectivity and is free of chiral resolution in the subsequent steps. Qualified product can be produced only through a simple re-crystallization step, so that the method is suitable for industrial production.
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Paragraph 0024; 0025; 0028; 0029
(2017/08/28)
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- A process for the preparation of key intermediates of Voriconazole
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The invention discloses a novel method for preparing a voriconazole key intermediate. The method comprises the following steps: catalyzing 1-(4-chloro-5-fluoropyridine-6-yl) halogenated ethane and 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazole-1-yl) ethanone by adopting a high-stereoselectivity chiral amino alcohol catalyst and a zinc-copper coupling agent, producing an asymmetric addition reaction to obtain (2R,3S/2S,3R)-2-(2,4-difluorophenyl)-3-(4-chloro-5-fluoropyridine-4-yl)-1-(1H-1,2,4-triazole-1-yl)-2-butanol, performing hydrogenation and dehalogenation to prepare a voriconazole key intermediate (2R,3S/2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyridine-4-yl)-1-(1H-1,2,4-triazole-1-yl)-2-butanol, and resolving to obtain the voriconazole. According to the method, the relatively economic and environment-friendly natural chiral amino alcohol catalyst is used; halogenated hydrocarbons and ketone are adopted to be subjected to the high-stereoselectivity asymmetric addition reaction, the process of preparing the halogenated hydrocarbons and active zinc into an organic zinc metal compound at first and then producing the asymmetric addition reaction between the compound and the ketone is removed, the operation is simplified, the production cost is reduced, and the industrialization is facilitated.
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- Method for synthesizing voriconazole
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The invention provides a method for synthesizing voriconazole, belonging to the field of medicine synthesis. The method comprises the following steps: by taking an intermediate A as a raw material, performing catalytic reaction with potassium formate and palladium-charcoal in the presence of inert gas so as to obtain a crude product of voriconazole, and recrystallizing the crude product of voriconazole, thereby obtaining voriconazole. According to the method, potassium formate is adopted as a hydrogen source and palladium-charcoal is adopted as a catalyst, helium atoms on pyrimidine rings of the intermediate A are removed, and thus raceme of voriconazole can be obtained. According to the method, the quantity of byproducts is few, the product quality is high, the reaction condition is gentle, the process security is high and the method is applicable to industrial large-scale production.
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Paragraph 0043; 0044; 0045; 0046; 0047-0061; 0063-0083
(2017/08/29)
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- Eluent tolerance and enantioseparation recovery of chiral packing materials based on chitosan bis(phenylcarbamate)-(n-octyl urea)s for high performance liquid chromatography
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The goal of the present work was to study the influence of the swelling of chitosan derivatives on the enantioseparation and the separation performance recovery of chiral stationary phases (CSPs) based on these derivatives. Therefore, six chitosan bis(phenylcarbamate)-(n-octyl urea)s were synthesized, which were coated on macroporous 3-aminopropyl silica gel affording new CSPs. Most of the CSPs demonstrated strong enantioseparation capability for the tested chiral compounds. The swelling capacity of the chitosan bis(phenylcarbamate)-(n-octyl urea)s in ethyl acetate, acetone and tetrahydrofuran (THF) was evaluated. Among the chitosan derivatives, the chitosan bis(3,5-dichlorophenylcarbamate)-(n-octyl urea) polymer showed the highest swelling capacity in ethyl acetate and THF. The polymer-based CSPs could be utilized with pure ethyl acetate and a normal phase containing 70% THF, but was damaged by pure THF. On the other hand, the separation performance of the damaged CSP could be recovered after it was allowed to stand for a period of time. The observations are important for the development and application of polysaccharide derivative-based CSPs.
- Wang, Jing,Huang, Shao-Hua,Chen, Wei,Bai, Zheng-Wu
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supporting information
(2016/12/02)
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- Voriconazole and intermediate preparation method (by machine translation)
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The invention provides a by the Voriconazole isomer preparation Voriconazole and intermediate preparation method. The method uses the Voriconazole isomer as the raw material, under the alkaline reaction conditions, in the 25 - 100 °C reaction under 1 - 24 hours, and then carry on the condensation reaction, the preparation obtained kang Zuoxiaofu Li racemic modification, to carry out a chiral racemic modification kang Zuoxiaofu Li obtained after the Voriconazole. The method of the invention can be recycled to a process generating a large amount of waste of Voriconazole isomer, avoiding the preparation fu Li conazole process the accessories and the waste of resources. Not only can greatly reduce the production cost, also can be the development of the cycle production, in order to save resources and the purpose of environmental protection. (by machine translation)
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- [...] B of a kind of preparation method
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The invention provides a novel method for preparing voriconazole crystal formation B, which is characterized in that voriconazole is dissolved into hydrophilic organic solvents, the solvents are slowly added into water, solid is separated out, and the voriconazole crystal formation B is obtained through filtration and separation. The preparation method of the crystal formation B provided by the invention is simple to operate, obtained products can be easily crushed, and the method is favorable for industrialized production.
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Paragraph 0022; 0024
(2017/01/12)
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- Novel voriconazole intermediate and synthesis of voriconazole
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The present invention relates to a method for preparing voriconazole represented by the following chemical formula 1, which comprises the steps of: 1) subjecting a compound represented by the following chemical formula 4 and a compound represented by the following chemical formula 5 to Reformatsky type coupling reaction to obtain a compound represented by the following chemical formula 3; 2) removing the substituents, thiol group and chloro group, from the compound of chemical formula 3 to obtain a racemate voriconazole represented by the following chemical formula 2; and 3) carrying out optical isolation of the racemate compound of chemical formula 2 by using an optically active acid. In chemical formulae 1-5, R represents a substituent selected from phenyl, pyridine, pyrimidine, thiazole, benzothiazole, benzoxazole, imidazole, 1-methylimidazole, C1-C4 alkyl or a combination thereof, wherein each substituent of the above substituents independently represents at least one selected from a halo, nitro and methoxy.
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- Synthetic method of voriconazole intermediate
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The invention provides a synthetic method of a novel voriconazole intermediate condensation compound shown as a formula II or an acid addition salt thereof. The voriconazole intermediate is prepared by compounds shown as a formula III and a formula IV, the feeding way is adjusted, the reaction condition is moderate and controllable, the generation of an impurity A is reduced, the impurity A is controlled within 0.74 percent, the use of toxic metal lead is avoided, and the danger caused by the residue of toxic metal in a drug is eliminated; and the product purity is higher, and the industrial application value is high.
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Paragraph 0061; 0062
(2016/10/20)
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- COMPOUND AND METHOD FOR MANUFACTURING THE SAME, AND METHOD FOR MANUFACTURING VORICONAZOLE
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PROBLEM TO BE SOLVED: To provide a method for manufacturing voriconazole, which is a therapeutic agent for severe or intractable deep mycosis such as aspergillosis, allowing easy manufacture without the need for the optical resolution. SOLUTION: A method for manufacturing voriconazole includes: obtaining a compound represented by the general formula (3) by using catalytic asymmetric cyanoacylation reaction; and reacting the compound with 1,2,4-triazole to convert it into voriconazole. [In the general formula (3), X is any of the divalent groups represented by the specified structural formulas.] COPYRIGHT: (C)2015,JPOandINPIT
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- PROCESS FOR THE PREPARATION OF VORICONAZOLE AND INTERMEDIATES THEREOF
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The present invention relates to an improved stereoselective process for the preparation of (2R,3S/2S,3R)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol intermediate compound. This intermediate compound is further used to prepare voriconazole—a triazole antifungal agent.
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- PROCESS FOR THE PREPARATION OF VORICONAZOLE AND ANALOGUES THEREOF
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The present invention provides a process for preparing a compound of formula: (Formula XI and XII) (XI) (XII) wherein X, Y, Z, A, B and E are as defined herein, by reacting a compound of formula: (Formula XIII) (XIII) with a compound of formula: (Formula XIV and XV) (XIV) (XV) respectively, in the presence of a transition metal catalyst, a ligand suitable for use with 15 the catalyst and a reducing agent. The invention also provides novel intermediates.
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Page/Page column 14; 16; 17
(2014/05/07)
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- An enantioselective synthesis of voriconazole
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A new seven-step sequence to access voriconazole, a clinically used antifungal agent, was developed. The initial catalytic asymmetric cyanosilylation is the key to constructing the consecutive tetra- and trisubstituted stereogenic centers. The fluoropyrimidine unit frequently triggered unexpected side reactions, but careful amendment of the reaction sequence allowed for the concise enantioselective synthesis.
- Tamura, Keiji,Furutachi, Makoto,Kumagai, Naoya,Shibasaki, Masakatsu
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p. 11396 - 11403
(2013/12/04)
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- PROCESS FOR PREPARING VORICONAZOLE BY USING NEW INTERMEDIATES
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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 racemic Voriconazole of Chemical Formula 2; and carrying out optical isolation of the racemic Voriconazole by adding an adequate optically active acid thereto to obtain Voriconazole having high optical purity with high cost-efficiency and high yield.
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- AN IMPROVED PROCESS FOR THE PREPARATION OF VORICONAZOLE AND INTERMEDIATES THEREOF
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The present invention relates to an improved stereoselective process for the preparation of (2R,3S/2S,3R)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)- 1-(1H-l,2,4-triazol-1-yl)butan-2-ol intermediate compound. This intermediate compound is further used to prepare voriconazole - a triazole antifungal agent.
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- NOVEL INTERMEDIATES OF VORICONAZOLE AND PREPARATION METHOD OF VORICONAZOLE USING THE SAME
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The present invention provides a compound of formula 2 and a compound of formula 4 which are a novel intermediate of voriconazole and a process for the preparation of voriconazole using the same. The novel intermediates of the present invention are environmentally-friendly due to no emission of irritative and offensive odor unique to thiols and enable the production of voriconazole with high purity and high yield.
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Page/Page column 11
(2012/05/04)
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- PROCESS FOR PREPARING VORICONAZOLE BY USING NEW INTERMEDIATES
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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.
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Page/Page column 14-15
(2011/09/14)
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- PROCESS FOR THE PREPARATION OF VORICONAZOLE
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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.
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Page/Page column 10
(2012/01/13)
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- Methods for predicting the response to statins
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The invention provides methods for optimizing therapeutic efficacy for treating hypercholesterolemia in a subject having a cardiovascular disease (CVD), comprising (a) determining subject characteristics that affect the likelihood of reaching a goal level of low density lipoprotein (LDL); and (b) obtaining success probabilities of a variety of statin treatments for reaching said goal level of LDL using said subject characteristics and a multivariate model; and (c) administrating the optimal statin treatment with the highest success probability of step (b) to said subject thereby optimizing therapeutic efficacy for treating hypercholesterolemia in said subject.
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- A NOVEL PROCESS TO MANUFACTURE (2R,3S)-2-(2,4-DIFLUOROPHENYL)-3-(5-FLUOROPYRIMIDIN-4-YL)-1-(1H-1,2,4-TRIAZOL-1-YL)BUTAN-2-OL
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The present invention relates to a novel industrially viable, cost effective process to manufacture substantially pure form of (2R,3S)-2-(2,4-difluorophenyl)-3-(5- fluoropyrimidin-4-yl)-l-(lH-l,2,4-triazol-l-yl)butan-2-ol (Voriconazole) with a chiral purity level of greater than 99.9 % and impurity level of less than 0.1 %.
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- PROCESS FOR THE PREPARATION OF VORICONAZOLE
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The present invention relates to an improved process for the preparation of Voriconazole.
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Page/Page column 5
(2010/04/23)
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- PROCESS FOR PREPARING VORICONAZOLE, NEW POLYMORPHIC FORM OF INTERMEDIATE THEREOF, AND USES THEREOF
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The present invention relates to an improved process for preparation of Voriconazole and Voriconazole (1R)-(?)-10-camphorsulfonate.
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Page/Page column 11
(2009/02/11)
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- 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
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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%.
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Page/Page column 8; 13
(2009/08/14)
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- PROCESS FOR PREPARATION OF NOVEL SALT OF VORICONAZOLE OXALATE FORM-C
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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).
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Page/Page column 6
(2009/05/30)
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- PROCESS FOR THE PRODUCTION OF VORICONAZOLE
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A process for the preparation of voriconazole is described wherein alkylthio substituted pyrimidines are key intermediates. The alkylthio substituents render the pyrimidines particularly suitable for metal mediated addition to ketones. This is demonstrated in a cross-coupling reaction for the preparation of voriconazole.
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Page/Page column 20-21
(2009/04/25)
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- IMPROVED PROCESS FOR THE PREPARATION OF 2R, 3S-2-(2,4-DIFLUOROPHENYL)-3-(5-FLUOROPYRIMIDIN-4-YL)-1-(1H-1,2,4-TRIAZOL-1-YL) BUTAN-2-OL (VORICONAZOLE)
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The present invention relates to an improved process for the preparation of 2R, 3S-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl) butan-2-ol. It may be represented as Formula (I).
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Page/Page column 10
(2008/06/13)
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- PROCESS FOR PREPARING VORICONAZOLE
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Voriconazole is prepared by a process comprising condensing 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazole-1-yl)ethanone with 4-chloro-6-ethyl-5-fluoropyrimidine, in a ketone, ether, aliphatic hydrocarbon, or aromatic hydrocarbon solvent, to give (2R, 3S/2S,3R)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-diflurophenyl)-1-(1H-1,2,4-triazole-1-yl)butan-2-ol.
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Page/Page column 19-20
(2010/11/08)
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- Novel antifungal 2-aryl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol derivatives with high activity against Aspergillus fumigatus
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Replacement of one triazole ring of fluconazole with 4-pyridinyl leads to an increase in activity against Aspergillus fumigatus. Introduction of an α-methyl group has a marked additional beneficial effect. Investigation of pyridinyl and pyrimidinyl analogues resulted in the identification of 30 (UK-109,496), voriconazole) which has excellent potency against a broad range of fungal pathogens including A. fumigatus and Candida krusei.
- Dickinson, Roger P.,Bell, Andrew S.,Hitchcock, Christopher A.,Narayanaswami, Subramaniyan,Ray, Stephen J.,Richardson, Kenneth,Troke, Peter F.
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p. 2031 - 2036
(2007/10/03)
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- Triazole antifungal agents
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The invention provide antifungal compounds of the formula: STR1 and pharmaceutically acceptable salts thereof, wherein R is phenyl substituted by 1 to 3 substituents each independently selected from halo, --CF3 and --OCF3 ; R1 is C1 -C4 alkyl; R2 is H or C1 -C4 alkyl; X is CH or N; and Y is F or Cl.
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- LONG CHAIN 1-AMINOTHIALANEPHOSPHONATES, THEIR SULPHINYL AND SULPHONYL DERIVATIVES. A NEW TYPE OF COMPLEXANE TYPE SURFACTANTS
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Several long chain 1-aminothiaalkanephosphonic acids 1 were prepared and selectively oxidized to the corresponding sulphinyl 2 and sulphonyl 3 derivatives.For all compounds synthesized surface tension properties were determined.These measurements indicate that the surface activities of compounds 1-3 are comparable with that of typical phosphonate detergents.Keywords: aminoalkanephosphonates, complexane type surfactants.
- Kudzin, Zbigniew H.,Mokrzan, Jerzy,Skowronski, Romuald
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