cas 171228-49-2, Posaconazole | Articles data

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Thiourea modified polyacrylnitrile fibers as efficient Pd(II) scavengers
A series of thiourea modified fibers were prepared and characterized. The N-(2-aminoethyl)thiourea functionalized polyacrylonitrile fiber (AETU-PANF) was then evaluated for palladium absorption. The absorption process follows a pseudo-second-order model and the equilibrium data fit well to the Langmuir isotherm model. The maximum absorption capacity according to the Langmuir model was 169.2 mg g-1 with an absorption limit of 0.03 ppm. Wetted AETU-PANFs exhibited excellent absorption properties in organic solutions and the sorption rates were higher in organic solvents than in aqueous solutions. This is due to a special microenvironment that is formed inside the AETU-PANFs. The AETU-PANFs were also used to remove palladium from an organic solution containing active pharmaceutical ingredients. The Pd content was reduced from 310 ppm to 0.07 ppm.
Cao, Jian,Xu, Gang,Xie, Yujia,Tao, Minli,Zhang, Wenqin
p. 58088 - 58098
(2016)
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An Improved Scalable Preparation of the Antifungal Posaconazole
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Jha, Anjali,Krishnam Raju, V. R.
(2021/11/12)

Preparation method of posaconazole
The invention discloses a preparation method of posaconazole. The preparation method comprises the following steps: in a reaction solvent acetonitrile, carrying out a cyclization reaction on SM1 and SM2 under the action of an organic base namely triethanolamine to generate an intermediate 1; in a reaction solvent dimethyl sulfoxide, carrying out a nucleophilic substitution reaction on the intermediate 1 and SM3 under the action of sodium hydroxide to generate an intermediate 2; and in a reaction solvent hydrochloric acid, removing benzyl from the intermediate 2 to obtain a posaconazole crude product: heating and dissolving the posaconazole crude product, crystallizing, filtering, and drying under reduced pressure to obtain posaconazole. The preparation method has the advantages that the reaction conditions are easy to control, the product yield reaches 98.6%, the product separation and purification are simple and convenient, and the method is suitable for industrial production.
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(2020/09/30)

Synthetic method of high-purity posaconazole
The invention discloses a synthetic method of high-purity posaconazole. The synthetic method comprises the following steps: S1, reacting a compound with a compound 2 to generate a compound 3; S2, removing anisole from the compound 3 under the action of hydrochloric acid to generate a compound required by the patent, namely posaconazole; and S3, carrying out primary refining on the obtained posaconazole crude product to obtain a medicinal high-purity posaconazole finished product.
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Paragraph 0008; 0016; 0017

(2020/12/31)

Preparation method of high-purity posaconazole
The invention discloses a preparation method of posaconazole, comprising: subjecting BP004b04 and oxalic acid to salt forming to obtain POE; subjecting POE and di-tert-butyl decarbonate to reaction inthe presence of a base to obtain POP, and recrystallizing POP; subjecting POP and POK o reaction in the presence of a base to obtain POR, and removing tert-butyl carbonate protecting group from POR to obtain POS; subjecting the POS to ring closing to obtain POB; subjecting the POB and POA to reaction to obtain posaconazole. Posaconazole prepared via the preparation method has the content of diastereoisomers being /=0.01%, and the overall route has high total yield.
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(2019/06/27)

A PROCESS FOR THE MANUFACTURE OF POSACONAZOLE
The present invention discloses an improved process for the manufacture of Posaconazole, an anti-fungal agent belonging to the category of substituted Tetrahydrofuran Triazole compound. The present invention further describes preparation of formula A and formula B, the key intermediates in the preparation of Posaconazole. The invention also discloses novel intermediates that are useful in the synthesis of Posaconazole.
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(2019/05/10)

POSACONAZOLE, COMPOSITION, INTERMEDIATE, PREPARATION METHOD THEREFOR, AND USES THEREOF
The present invention relates to a compound of formula III, wherein, R is selected from the group consisting of C1-C4 alkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted benzyl, preferably isopropyl; and two Ar groups may be the same or different, and are each independently selected from the group consisting of substituted or unsubstituted aryl groups, preferably substituted or unsubstituted phenyl, such as p-methoxyphenyl and the like, wherein the compound is preferably in a solid form.
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(2019/03/14)

Preparation method of posaconazole
The invention discloses a preparation method of posaconazole. According to the preparation method, in the presence of ammonium formate and a catalyst, in an organic solvent, a compound (I) carries outdebenzylation reactions to obtain a compound (A). The preparation method has the advantages of high yield, high purity, mild conditions, and simple operation.
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Paragraph 0045-0099

(2019/10/02)

New preparation method for posaconazole and intermediate thereof
The invention belongs to the technical field of medicines and relates to a preparation method of a posaconazole intermediate and a new method for applying the intermediate to preparation of posaconazole. The preparation method of posaconazole comprises the following steps: a) carrying out etherification reaction on a compound shown in a formula III and a compound shown in a formula IV under alkaline condition and in a non protonic solvent, thus obtaining a compound shown in a formula V; b) carrying out reaction on the compound shown in the formula V in presence of palladium carbon and formic acid, thus obtaining a posaconazole intermediate compound shown in a formula II; and c) carrying out alkaline hydrolysis reaction on the compound shown in the formula II, thus obtaining posaconazole. Compared with a known method, the invention provides a new method for preparing the posaconazole intermediate II, and the intermediate II is subjected to alkaline hydrolysis, so that the final productposaconazole I is obtained; and compared with an existing technique, the new technique of the invention is greatly reduced in purification difficulty, impurities in a product are greatly reduced, purity is obviously improved, number of recrystallization times is reduced, yield is improved, production cost is reduced, and operation is easy, safe and reliable, thereby being applicable to industrialproduction. (The formulas II, III, IV and V are described in the specification).
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(2018/07/30)

Preparation method of posaconazole
The invention discloses preparation methods of antifungal drug posaconazole shown in the formula as shown in the specification. A first preparation method comprises the following steps: by taking a compound 1 as a raw material, performing amino protection so as to obtain a compound 2, performing reaction on alcohol 3 with a sulfonylation reagent in the presence of alkali to protect hydroxyl so as to obtain a compound 4, performing reaction on an intermediate 2 with triazole under a strong alkali condition so as to obtain an intermediate 5, performing condensation and cyclization with a formylhydrazine derivative 6 under an organic alkali condition so as to obtain a posaconazole key intermediate compound 7, and removing a protection group R2, thereby obtaining posaconazole; a second preparation method comprises the following steps: performing cyclization reaction on the compound 2 with the compound 6 in the presence of organic alkali so as to obtain a compound 8, performing nucleophilic substitution reaction on the compound 8 and the compound 4 under the action of strong alkali so as to obtain a compound 7, and removing the protection group R2, thereby obtaining posaconazole.
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Paragraph 0100; 0106; 0107

(2017/07/26)

Preparation method of high purity posaconazole
The invention discloses a posaconazole (compound 1) refining method, the method is as follows: a posaconazole derivative is prepared by an esterification method from a posaconazole crude product, then the posaconazole derivative is refined by recrystallization, then high purity posaconazole can be obtained by catalyzed alcoholysis and crystallization of the posaconazole ester derivative in an alcohol, and the purity can reach 99.8% or more than 99.8%.
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Paragraph 0021; 0022

(2017/06/02)

Preparation method of posaconazole
The invention discloses a preparation method of posaconazole. The preparation method of the posaconazole provided by the invention comprises the following steps: in the presence of inorganic protonic acid, performing hydrolysis reaction on a compound II to obtain posaconazole I. The preparation method provided by the invention is easy and safe to operate, does not need any special equipment, is free from heavy metal residues, produces less reaction side products, and has high yield; a prepared product has high purity (chiral purity is larger than 99.90 percent, related substance purity is larger than 99.50 percent, all impurities are less than 0.1 percent, and raw materials meet the standard), is low in production cost, is environmentally friendly, and is suitable for industrial production. The formula of the posaconazole is shown in the description.
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(2017/08/29)

CRYSTALLINE FORMS OF POSACONAZOLE INTERMEDIATE AND PROCESS FOR THE PREPARATION OF AMORPHOUS POSACONAZOLE
The present invention provides an industrial method production of amorphous posaconazole. The present invention also relates to a method for production of the posaconazole via and novel crystalline forms of posaconazole intermediate. More particularly the present invention relates to novel crystalline forms of posaconazole intermediate and methods for production of novel crystalline forms of posaconazole intermediate represented by the following structural formula III Which is key intermediate in the production of posaconazole. The present invention also provides for the one pot process for the preparation of amorphous posaconazole using novel crystalline forms of benzyl posaconazole.
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Page/Page column 19; 20

(2017/04/11)

Posaconazole synthesis method
The invention provides a posaconazole synthesis method which includes the steps: S1, taking a compound displayed by a following formula II as a raw material, taking hydrogen as a hydrogen source, stirring the compound displayed by the formula II, catalysts and acidic reagents in reaction solvents under the hydrogenation debenzylation reaction condition, and performing contact reaction to obtain mixed solution; S2, reducing the temperature of the mixed solution to range from 0 DEG C to 5 DEG C, dropping sodium hydroxide solution into the mixed solution until a pH (potential of hydrogen) value of the mixed solution is 10-12, stirring, filtering to obtain filter cakes, washing the filter cakes, and drying the washed filter cakes to obtain posaconazole as shown in the following formula I.
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Paragraph 0020; 0044; 0045; 0049; 0050; 0054; 0055

(2017/02/24)

Preparation method of novel triazole antifungal drug
The invention relates to a preparation method of a novel triazole antifungal drug and concretely relates to a posaconazole preparation method. The preparation method comprises that a compound II undergoes a debenzylation reaction without a Pd catalyst under normal pressure to produce posaconazole, and after the reaction, posaconazole is extracted through a water-insoluble organic solvent under acidic conditions so that genotoxic impurity benzyl chloride is substantially removed. The preparation method has the advantages of operation simpleness and convenience, high safety, controllable final product quality and high purity and yield.
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Paragraph 0021

(2016/11/24)

IMPROVED PROCESS FOR THE PREPARATION OF ((3S,5R)-5-((1H-1,2,4-TRIAZOL-1-YL)METHYL)-5-(2,4-DIFLUOROPHENYL)TETRAHYDROFURAN-3-YL)METHYL-4-METHYLBENZENESULFONATE
The present invention relates to process for the preparation of ((3S,5R)-5-((lH-l,2,4- triazol- 1 -yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl-4-methylbenzene sulfonate compound of formula- 1 through novel intermediates. Further the said compound of formula- 1 is useful as a key intermediate for the preparation of Posaconazole.
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(2015/05/06)

Process for the Preparation of Triazole Antifungal Drug, Its Intermediates and Polymorphs Thereof
A process for the preparation of 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furanyl]methoxy]phenyl]-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one compound of formula-1, its intermediates and polymorphs thereof. (I)
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(2014/12/09)

PROCESS FOR THE PREPARATION OF A CHIRAL COMPOUND
The present invention relates to a process for the preparation of a compound of formula (V), in particular posaconazole, wherein said process comprises the steps of (1) providing a mixture comprising a compound of formula (IV), a protic solvent system, and a suitable base; and (2) heating the mixture of (1) to obtain a mixture comprising the compound of formula (V).
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(2014/10/16)

PROCESS FOR THE PREPARATION OF A CHIRAL COMPOUND
The present invention relates to a process for the preparation of a compound of formula (V), in particular posaconazole, wherein said process comprises the steps of (1) providing a mixture comprising a compound of formula (IV), a protic solvent system, and a suitable base; and (2) heating the mixture of (1) to obtain a mixture comprising the compound of formula (V).
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Page/Page column 108-110

(2013/02/28)

PROCESS FOR THE PREPARATION OF CHIRAL TRIAZOLONES
A process for the preparation of a chiral compound, in particular posaconazole, wherein the process comprises mixing and reacting the compounds of formula (I) Y3-NH2; of formula (Ila) 0=C=N-Y0 and/or of formula (lIb) and of formula (III) in a solvent in any order to obtain a reaction mixture containing a chiral compound of formula (IV) and/or formula (V).
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(2011/12/04)

PROCESS FOR PREPARATION OF POSACONAZOLE AND CRYSTALLINE POLYMORPHIC FORM V OF POSACONAZOLE
The present invention generally relates to a process for the preparation of an antifungal agent posaconazole and to a novel polymorphic form V of antifungal agent posaconazole.
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Page/Page column 30-31

(2012/01/06)

PROCESS FOR PREPARING POSACONAZOLE AND INTERMEDIATES THEREOF
The present invention relates to an industrially advantageous process for the preparation of tetrahydrofuran antifungals preferably posaconazole of formula I. The present invention further relates to improved processes for preparing key and novel intermediates useful in the preparation of posaconazole. The present invention further relates to improved processes for preparing the compound of formula II, a key intermediate in the preparation of posaconazole.
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Page/Page column 22

(2009/12/27)

Hydroxylated analogues of the orally active broad spectrum antifungal, Sch 51048 (1), and the discovery of posaconazole [Sch 56592; 2 or (S,S)-5]
As part of a detailed study, the syntheses, biological activities, and pharmacokinetic properties of hydroxylated analogues of the previously described broad spectrum antifungal agents, Sch 51048 (1), Sch 50001 (3), and Sch 50002 (4), are described. Based on an overall superior profile, one of the alcohols, Sch 56592 (2), was selected for clinical studies.
Bennett, Frank,Saksena, Anil K.,Lovey, Raymond G.,Liu, Yi-Tsung,Patel, Naginbhai M.,Pinto, Patrick,Pike, Russel,Jao, Edwin,Girijavallabhan, Viyyoor M.,Ganguly, Ashit K.,Loebenberg, David,Wang, Haiyan,Cacciapuoti, Anthony,Moss, Eugene,Menzel, Fred,Hare, Roberta S.,Nomeir, Amin
p. 186 - 190
(2007/10/03)

TETRAHYDROFURAN PHOSPHATE- AND HYDROXY ESTERS, AS PRODRUGS FOR THE CORRESPONDING ANTIFUNGAL AGENT
A compound of formula (I) wherein G is H or PO3H2 or a pharmaceutical acceptable salt thereof, pharmaceutical compositions containing such compounds and method of using such compounds or pharmaceutical compositions containing them to treat or prevent fungal infection are disclosed.
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Page 3

(2010/02/10)

Crystalline antifungal polymorph
The crystalline polymorph Form I of (?)-4-[4-[4-[4-[[(2R-cis)-5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)furan-3-yl]methoxy]phenyl]-1-piperazinyl]phenyl-2,4-dihydro-2-[(S)-1-ethyl-2(S)-hydroxylpropyl]-3H-1,2,4-triazol-3-one represented by the formula I pharmaceutical compositions containing such a polymorph and methods of using such a polymorph to treat fungal infections in mammals are disclosed.
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Page/Page column 13

(2008/06/13)

Stereoselective Grignard additions to N-formyl hydrazone: A concise synthesis of NoxafilR side chain and a synthesis of Noxafil R
Addition of ethyl Grignard reagent to the formyl hydrazone 11 via in situ silylation provided the corresponding formyl hydrazine with excellent diastereoselectivity in favor of the desired S,S-diastereoisomer 6. Treatment of 6 with the phenyl carbamate 13 efficiently provided the O-benzyl protected Noxafil, which was deprotected to provide NoxafilR.
Saksena, Anil K.,Girijavallabhan, Viyyoor M.,Wang, Haiyan,Lovey, Raymond G.,Guenter, Frank,Mergelsberg, Ingrid,Puar, Mohinder S.
p. 8249 - 8251
(2007/10/03)

Mono N-arylation of piperazine(III): Metal-catalyzed N-arylation and its application to the novel preparations of the antifungal posaconazole and its advanced intermediate
A novel application of Pd0-catalyzed arylation to mono N-arylated piperazines, its mechanism, and its application towards the novel syntheses of the key differentially N,N′-diarylated piperazine antifungal intermediate N-(4-hydroxyphenyl)-N′-(4-aminophenyl)piperazine 5 as well as posaconazole 1 are described.
Hepperle, Michael,Eckert, Jeffrey,Gala, Dinesh,Shen, Lan,Anderson Evans,Goodman, Andrew
p. 3359 - 3363
(2007/10/03)