cas 138530-94-6, R-(+)-Lansoprazole | Articles data

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Two-dimensional chromatography method applied to the enantiomeric determination of lansoprazole in human plasma by direct sample injection
A two-dimensional HPLC method based on the direct injection of biological samples has been developed and validated for the determination of lansoprazole enantiomers in human plasma. The lansoprazole enantiomers were extracted from the biological matrix using an octyl restricted access media bovine serum albumin column (C8 RAM BSA) and the enantioseparation was performed on an amylose tris(3,5-dimethoxyphenylcarbamate) chiral column using acetonitrile:water (35:65 v/v) and UV detection at 285 nm. Analysis time was 25 min with no time spent on sample preparation. The method was applied to the analysis of the plasma samples obtained from nine Brazilian volunteers who received a 30 mg oral dose of racemic lansoprazole and was able to quantify the enantiomers of lansoprazole in the clinical samples analyzed.
Gomes, Ricardo F.,Cassiano, Neila M.,Pedrazzoli Jr.,Cass, Quezia B.
p. 35 - 41
(2010)
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Method for preparing dexlansoprazole through catalysis of hexadentate ligand
The invention belongs to the technical field of chemical engineering, and particularly provides a method for preparing dexlansoprazole through catalysis of a hexadentate ligand. Under the catalysis ofa complex formed by a Ti(O-iPr)4 catalyst and a self-made hexadentate ligand, lansoprazole thioether is subjected to asymmetric oxidation, and dextral lansoprazole is obtained. The hexadentate ligandused in the method is simple to prepare and high in yield, and the complex formed by the hexadentate ligand and the Ti(O-iPr)4 catalyst is high in catalytic efficiency and high in enantiomeric excessvalue.
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Paragraph 0046; 0048-0049; 0051

(2020/05/30)

Preparation method of high-optical-purity anti-gastric-ulcer drug R-lansoprazole
The invention belongs to the technical field of chiral synthesized chemical drugs and in particular relates to a preparation method of a high-optical-purity anti-gastric-ulcer drug R-lansoprazole. According to the preparation method, a molecular sieve is used as a carrier and tungsten trioxide is loaded on the surface of the molecular sieve in situ to prepare a tungsten loaded molecular sieve; L-hydroxyproline and tetraisopropyl titanate form a complex compound and the complex compound is deposited on the surface of the tungsten loaded molecular sieve and/or in a pore diameter to form a tungsten-titanium double-metal center catalyst; the catalyst can be used for catalyzing thioether2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-yl]-methylthio-1H-benzimidazole to be subjected to oxidization reaction to obtain the high-optical-purity R-lansoprazole; the chemical purity and optical purity of the prepared product reach requirements of medical-grade crude drugs.
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Paragraph 0052-0057

(2018/08/03)

Dexlansoprazole single crystal, and preparation method and application thereof
The invention discloses an industrial preparation method for a single crystal of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]-sulfinyl]-1H-benzimidazole (dexlansoprazole). The singlecrystal has water content of less than 0.1% and belongs to a monoclinic system; the space group of the single crystal is P21; the cell parameters of the single crystal are that a is equal to 8.4771(17) angstroms; b is equal to 23.246(5) angstroms; c is equal to 8.5628(17) angstroms; alpha is equal to 90 DEGs; beta is equal to 103.32(3) DEGs; gamma is equal to 90 DEGs; a cell volume V is equal to 1641.9(6) angstroms ; and an in-unit-cell molecule number Z is equal to 4. Moreover, the invention further discloses application of the crystal to preparation of pharmaceutical compositions used fortreating heartburn related to the non-erosive gastrcosophageal reflux disease and erosive esophagitis of different degrees.
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Paragraph 0018-0023

(2018/07/07)

Ultrafast chiral separations for high throughput enantiopurity analysis
Recent developments in fast chromatographic enantioseparations now make high throughput analysis of enantiopurity on the order of a few seconds achievable. Nevertheless, routine chromatographic determinations of enantiopurity to support stereochemical investigations in pharmaceutical research and development, synthetic chemistry and bioanalysis are still typically performed on the 5-20 min timescale, with many practitioners believing that sub-minute enantioseparations are not representative of the molecules encountered in day to day research. In this study we develop ultrafast chromatographic enantioseparations for a variety of pharmaceutically-related drugs and intermediates, showing that sub-minute resolutions are now possible in the vast majority of cases by both supercritical fluid chromatography (SFC) and reversed phase liquid chromatography (RP-LC). Examples are provided illustrating how such methods can be routinely developed and used for ultrafast high throughput analysis to support enantioselective synthesis investigations.
Barhate, Chandan L.,Joyce, Leo A.,Makarov, Alexey A.,Zawatzky, Kerstin,Bernardoni, Frank,Schafer, Wes A.,Armstrong, Daniel W.,Welch, Christopher J.,Regalado, Erik L.
supporting information
p. 509 - 512
(2017/01/13)

Dexlansoprazole and its preparation method and use
The invention provides a dexlansoprazole and its preparation method and use. The preparation method of dexlansoprazole comprises synthesizing a dexlansoprazole crude product through a simple process and carrying out further optical purity refinement and purification to obtain a dexlansoprazole product having optical purity close to 100%. The dexlansoprazole product has optical purity close to 100%, has high purity, can be used as a medicinal component and has a better effect.
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Paragraph 0182-0188; 0189-0303

(2017/08/31)

Preparation method of R-lansoprazole
The invention provides a preparation method of R-lansoprazole. According to the preparation method, a compound represented by formula 1 is taken as a raw material, a titanium catalyst ligand, an organic solvent, tetraisopropyl titanate, N, N-diisopropylethylaine, and an oxidizing agent are added, and R-lansoprazole is synthesized via catalytic oxidation. In the preparation method, the novel titanium catalyst ligand is adopted, so that the stability of a titanium catalyst compound is increased, the titanium catalyst compound can be filtered in solid, R-lansoprazole yield is increased, and compound ee value is increased obviously.
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Paragraph 0026; 0027; 0032; 0034; 0044; 0048; 0052

(2017/12/27)

Oxidization method for dexlansoprazole
The invention provides a green and efficient method for preparing dexlansoprazole through oxidization. An organic-inorganic hybrid material-oxidant system is adopted, thus the product can be obtained in a green, high-yield and high-purity manner, and a catalyst can be cyclically used. The obtained dexlansoprazole can be directly used as a raw material medicine.
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Paragraph 0014; 0015; 0016; 0017; 0018; 0019; 0020

(2017/05/05)

Oxidation method of Dexlansoprazole
The invention provides a green and highly-efficient oxidation method for preparing Dexlansoprazole. An organic-inorganic hybrid material-oxidant system is adopted, the above product is obtained in a green, high-yield and high-purity manner, and a catalyst can be reused. The obtained Dexlansoprazole can be directly used as a bulk drug.
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Paragraph 0014; 0015; 0016; 0017; 0018; 0019; 0020

(2017/05/05)

Optical purity of the lansoprazole preparation method
The invention provides a preparation method of optically pure 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (Lansoprazole). The method required to be protected in the invention comprises the following steps: directly asymmetrically oxidizing 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfeny]-1H-benzimidazole in the presence of a complex catalyst under the action of an organic alkali or inorganic alkali additive or without the organic alkali or inorganic alkali additive to form corresponding Lansoprazole rich in single enantiomers, wherein the complex catalyst is formed through a reaction of (R,R) or (S,S)-N,N'-tartric acid dibenzyl amide ligand, alkoxytitanium and water at a certain temperature; and sequentially carrying out alcohol-water and ketone-water recrystallization to obtain the optically pure Lansoprazole.
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Paragraph 0020-0123

(2017/05/26)

Oxidation method for Dexlansoprazole
The invention provides a green and efficient method for preparing Dexlansoprazole in an oxidation manner. The product can be obtained in a green, high-yield and high-purity manner through adopting an organic-inorganic hybrid material-oxidant system; and moreover, a catalyst can be cyclically used. The obtained Dexlansoprazole can be directly used as a raw material medicine.
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Paragraph 0015-0017

(2017/07/23)

Preparation method for dexlansoprazole
The invention discloses a preparation method for dexlansoprazole, belonging to the field of organic synthesis. The method comprises the following steps: (1) carrying out reaction on 2-hydroxymethyl-3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine and thionyl chloride, and compounding 2-chloromethyl-3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine; (2) putting 2-chloromethyl-3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine acquired in the step (1) and 2-sulfydryl-1H-benzimidazole into an aqueous liquid, and then adding a phase transfer catalyst and sodium hydroxide, thereby acquiring 2-[[3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine-2-group] methylmercapto]-1H-benzimidazole; (3) taking L-ethyl tartrate as a chiral assistant agent, titanium isopropoxide and diisopropylethylamine as a catalyst and cumyl hydroperoxide as an oxidizing agent and reacting with 2-[[3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine-2-group] methylmercapto]-1H-benzimidazole acquired in the step (2) at low temperature, thereby acquiring dexlansoprazole. The preparation method for dexlansoprazole disclosed by the invention is simple and efficient, is capable of obviously shortening the reaction time under the condition of guaranteeing the product yield and is capable of improving the product quality.
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Paragraph 0025; 0033; 0034; 0035; 0036; 0037; 0038

(2017/08/28)

Ti-Salan catalyzed asymmetric sulfoxidation of pyridylmethylthiobenzimidazoles to optically pure proton pump inhibitors
The asymmetric sulfoxidation of two pyridylmethylthiobenzimidazoles to anti-ulcer drugs of the PPI family (S)-omeprazole and (R)-lansoprazole with hydrogen peroxide, mediated by a series of chiral titanium(IV) salan complexes is reported. High sulfoxide yields (up to?>95%) and enantioselectivities (up to 94% ee) have been achieved. The introduction of electron-withdrawing substituents leads to less active and less enantioselective catalysts. Like for the previously reported Ti-salalen catalyzed sulfoxidations, the temperature dependence of the sulfoxidation enantioselectivity in the presence of Ti-salan complexes is nonmonotonic, demonstrating isoinversion behavior with decreasing temperature. The oxidation is likely rate-limited by the formation of the active (presumably peroxotitanium(IV)) species, followed by a faster oxygen transfer to the substrate.
Talsi, Evgenii P.,Bryliakov, Konstantin P.
p. 84 - 89
(2016/11/11)

An electronic circular dichroism study for the structurechiroptical relationship of chiral proton pump inhibitors
In this paper, we investigated the electronic circular dichroism (ECD) of proton pump inhibitors (PPIs) using a method of combining experimental spectrum and time-dependent density functional theory (TD-DFT) calculations. In our research, an intriguing helicity-like phenomenon was discovered for the relationship between static dipole moment and ECD curves of different conformers in lansoprazole. The scope and validity of the precious phenomenon have been examined by four PPIs using the same method. Hence, it can be used as a reference to determine and verify the absolute configuration of PPIs-type and PPIs-like chiral sulfoxide.
Zhou, Zhixu,Li, Linwei,Yan, Ning,Du, Lei,Sun, Changshan,Sun, Tiemin
supporting information
p. 110 - 112
(2016/03/01)

D-tartaric acid monoester monoamide compound
The invention relates to a D-tartaric acid monoester monoamide compound, capable of serving as a ligand to catalytically synthesize R type chirality proton pump inhibitors such as Dexlansoprazole. A synthesis method comprises the steps of dissolving a compound II and the D-tartaric acid monoester monoamide compound into an organic solvent, and heating to react, thus obtaining the R type chirality proton pump inhibitors such as the Dexlansoprazole. The method has higher yield and e.e value.
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Paragraph 0177-0181

(2017/01/17)

Synthesis of prazole compounds
The present disclosure relates to non-naturally occurring monooxygenase polypeptides useful for preparing prazole compounds, polynucleotides encoding the polypeptides, and methods of using the polypeptides.
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Page/Page column 94-96

(2016/02/03)

Benzimidazole compound crystal
A novel crystal of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole or a salt thereof of the present invention is useful for an excellent antiulcer agent.
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Page/Page column 8

(2015/11/24)

NOVEL SOLVATE OF DEXLANSOPRAZOLE
The present invention provides novel solvate of dexlansoprazole (or R-lansoprazole), particularly diol solvate and its hydrate form of dexlansoprazole (or R-lansoprazole) which is chemically known as (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole compound of the formula (I), as well as processes for the preparation thereof. The said solvates are useful in the preparation of dexlansoprazole with enhanced chiral purity and better HPLC purity with less sulphone impurity content.
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Paragraph 0073

(2013/03/26)

GLYCEROL SOLVATE FORMS OF (R) - 2 - [ [ [3 -METHYL -4 (2,2, 2 - TRIFLUOROETHOXY) PYRIDIN- 2 - YL] METHYL] SULPHINYL] - 1H - BEN ZIMIDAZOLE
The present invention relates to novel crystalline forms of (R)-2-[[[3-methyl-4(2,2,2- trifluoroethoxy)pyridin-2-yl]methyl]sulphinyl]-lH-benzimidazole (Formula 1), to processes for their preparation, to pharmaceutical compositions comprising the same and to the use of such crystalline forms for the treatment of gastrointestinal (GI) disorders.
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Page/Page column 46-47

(2013/10/08)

PROCESS FOR THE PREPARATION OF DEXLANSOPRAZOLE
The present invention relates to a process for the preparation of crystalline dexlansoprazole.
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Page/Page column 4-5

(2012/08/27)

PROCESS FOR THE PREPARATION OF DEXLANSOPRAZOLE
The present invention relates to a process for the preparation of dexlansoprazole.xH2O, wherein x is about 0.0 to about 0.1, using dexlansoprazole.xH2O, wherein x is about 2.6 to about 50.
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Page/Page column 5

(2013/02/28)

An efficient synthesis of dexlansoprazole employing asymmetric oxidation strategy
An alternative and scalable synthesis of dexlansoprazole ((R)-(+)-1); the (R)-enantiomer of Lansoprazole with an enantiomeric excess of >99.8% is presented.
Raju, Manne Naga,Kumar, Neelam Uday,Reddy, Baddam Sudhakar,Anitha, Naredla,Srinivas, Gangula,Bhattacharya, Apurba,Mukkanti, Kagga,Kolla, Naveenkumar,Bandichhor, Rakeshwar
p. 5464 - 5466
(2011/11/01)

PROCESS FOR THE PREPARATION OF DEXLANSOPRAZOLE
The present invention relates to a process for the preparation of crystalline dexlansoprazole.
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Page/Page column 4

(2011/10/13)

NOVEL SOLVATE OF DEXLANSOPRAZOLE
The present invention provides novel solvate of dexlansoprazole (or R- lansoprazole), particularly diol solvate and its hydrate form of dexlansoprazole (or R-lansoprazole) which is chemically known as (R)-2-[[[3-methyl-4-(2,2,2- trifluoroethoxy)-2-pyridinyl] methyl] sulfmyl]-lH-benzimidazole compound of the formula (I), as well as processes for the preparation thereof. The said solvates are useful in the preparation of dexlansoprazole with enhanced chiral purity and better HPLC purity with less sulphone impurity content.
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Page/Page column 18

(2011/09/15)

SALTS OF DEXLANSOPRAZOLE AND THEIR PREPARATION
The present invention relates to the salts of dexlansoprazole in amorphous form. The present invention further relates to processes for the preparation of salts of dexlansoprazole.
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Page/Page column 4-5

(2011/10/13)

OPTICAL RESOLUTION OF SUBSTITUTED 2-(2- PYRIDINYLMETHYLSULPHINYL)-1H-BENZIMIDAZOLES
The present invention relates to process for preparation of optical resolution of substituted 2-(2-pyridinylmethylsulphinyl)-1H-benzimidazoles either as a single enantiomer or in an enantiomerically enriched form. Thus, for example, R-1,1'-binaphtyl- 2-2'-diyl hydrogen phosphate was reacted with 2-[[[3-methyl-4-(2,2,2-trifluoro-ethoxy)- 2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole (Lansoprazole) in a mixture of benzene and cyclohexane to obtain diasteremeric complexes. The diasteremeric complexes were subjected to fractional crystallization to obtain R-2-[[[3-methyl-4-(2,2,2-trifluoro- ethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole.R-1,1'-binaphthyl-2-2'-diyl hydrogen phosphate. The separated isomer was treated with sodium bicarbonate in a mixture of ethyl acetate and water to obtain R-2-[[[3-methyl-4-(2,2,2-trifluoro-ethoxy)-2- pyridinyl]methyl]sulfinyl]-1H-benzimidazole (dexlansoprazole).
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Page/Page column 18

(2011/04/26)

Process for Preparation of Stable Amorphous R-Lansoprazole
A process for preparing stable amorphous R-(+)-lansoprazole comprising optically resolving racemic lansoprazole by the formation of host-guest inclusion complexes by selectively and reversibly including chiral guest molecules in the lansoprazole.
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Page/Page column 2-3

(2010/12/29)

PROCESS FOR THE PREPARATION OF PROTON PUMP INHIBITORS
The present invention relates to novel and improved processes for the preparation of Proton Pump Inhibitors such as 2-[(R)-[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole and pharmaceutically acceptable salts thereof.
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Page/Page column 22

(2010/09/17)

PROCESS FOR PREPARING (R)-(+)-LANSOPRAZOLE AND INTERMEDIATE USED THEREIN
A process for the preparation of (R)-(+)-lansoprazole having a high optical purity and a novel intermediates used therein are provided. The inventive process provides (R)-(+)-lansoprazole having a high optical purity through optical resolution of racemic lansoprazole.
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Page/Page column 9-10

(2010/07/02)

CRYSTALLINE FORMS OF DEXLANSOPRAZOLE
Provided are crystalline forms of dexLansoprazole, as well as processes for the preparation thereof.
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Page/Page column 27

(2010/04/27)

DEXLANSOPRAZOLE PROCESS AND POLYMORPHS
Processes for the preparation of dexlansoprazole, an amorphous form of dexlansoprazole, a solid dispersion of amorphous dexlansoprazole and a pharmaceutically acceptable carrier, and processes for their preparation. Also provided are crystalline compounds 2-[(R)-[(4-chloro-3-methyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole and 2-[(R)-[(4-nitro-3-methyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole, and methods for their preparation.
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Page/Page column 57-58

(2009/10/22)

CRYSTAL OF BENZIMIDAZOLE COMPOUND
Provided is a crystal of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole showing an X-ray powder diffraction pattern having characteristic peaks at interplanar spacings (d) of 10.06±0.2, 8.70±0.2, 6.57±0.2, 5.59±0.2 and 4.00±0.2 Angstroms. The present invention provides a stable antiulcer drug superior in the absorbability.
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Page/Page column 21-22; 26

(2009/10/22)

A PROCESS FOR PREPARATION OF STABLE AMORPHOUS R-LANSOPRAZOLE
A process for preparing stable amorphous R-(+)-lansoprazole comprising optically resolving racemic lansoprazole by the formation of host-guest inclusion complexes by selectively and reversibly including chiral guest molecules in the lansoprazole.
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Page/Page column 6-8

(2009/09/04)

A PROCESS OF SULFOXIDATION OF BIOLOGICALLY ACTIVE COMPOUNDS
The present invention relates to a new process for the preparation of sulfoxides, preferably stereoselective preparation of substituted or unsubstituted chiral sulfinyl derivatives 2-(2- pyridylmethyl) sulfinyl-l H-benzimidazole by oxidation with oxaziridine in presence of suitable solvent and base.
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Page/Page column 18

(2009/01/24)

Highly enantioselective oxidation of sulfides to sulfoxides by a new oxaziridinium salt
The new oxaziridinium salt 5 (R2 = TBDPS) is an effective reagent for the highly enantioselective oxidation of sulfides to sulfoxides with up to >99% ee and good yields. As such, it represents a new valuable nonmetallic alternative to the existing methods for asymmetric sulfoxidation.
Del Rio,Wang,Achab,Bohe
p. 2265 - 2268
(2008/02/04)

STABLE SOLID PREPARATIONS
It is intended to provide a process for producing unstable amorphous benzimidazole compounds having a proton pump inhibitor function, and stable solid preparations for medicinal use containing these compounds which are produced by blending such an amorphous benzimidazole compound with a nontoxic base such as a basic inorganic salt, forming an intermediate coating layer on the layer containing the active ingredient and further forming an enteric coating layer or a release-controlling coating layer.
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Page/Page column 13-14

(2008/06/13)

WO3-30% H2O2-cinchona alkaloids: A new heterogeneous catalytic system for the asymmetric oxidation of sulfides and the kinetic resolution of racemic sulfoxides
WO3-catalyzed asymmetric oxidation of thioethers and kinetic resolution of sulfoxides with 30% aq. H2O2 in the presence of cinchona alkaloids under heterogeneous conditions affords chiral sulfoxides in high yields with moderate to good enantioselectivities.
Thakur, Vinay V.,Sudalai
p. 407 - 410
(2007/10/03)

Benzimidazole compound crystal
A novel crystal of (R)-2-[[[3-methyl-4-(2, 2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole or a salt thereof of the present invention is useful for an excellent antiulcer agent.
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(2008/06/13)