Tag: 300-400

On October 5, 2018, Nishiguchi, Shigenobu; Izumi, Takuhiro; Kouno, Takayoshi; Sukegawa, Junpei; Ilies, Laurean; Nakamura, Eiichi published an article.Related Products of 73590-85-9 The title of the article was Synthesis of Esomeprazole and Related Proton Pump Inhibitors through Iron-Catalyzed Enantioselective Sulfoxidation. And the article contained the following:

We report here an application of iron catalysis for the kilogram scale asym. synthesis of a proton pump inhibitor, esomeprazole, in 87% yield and 99.4% ee by catalytic sulfoxidation with hydrogen peroxide using an iron salt/chiral Schiff base in combination with a carboxylate salt. Under similar reaction conditions, other proton pump inhibitors such as (S)-lansoprazole, (S)-rabeprazole, and (S)-pantoprazole, were also synthesized in high yield and ee. A carboxylate additive was crucial for the success of this reaction, and we consider that it coordinates to the active iron species, and it also acts as a hydrogen-bond acceptor to coordinate to the substrate through the imidazole NH. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Related Products of 73590-85-9

The Article related to iron catalyzed enantioselective sulfoxidation esomeprazole synthesis, proton pump inhibitor synthesis iron catalyzed enantioselective sulfoxidation, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Related Products of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On March 31, 2016, Song, Guo-Qiang; Qin, Feng; Huang, Xian-Feng; Lv, Xiao-Bing; Yang, Bei published an article.Electric Literature of 73590-85-9 The title of the article was Easy Removal of N-carboxybenzyl (Cbz) Protective Group by Low-Carbon Alcohol. And the article contained the following:

A new method for the removal of benzyloxycarbonyl protective group was established. It was accomplished by using methanol, ethanol or t-butanol as a deprotective reagent, and the scope and limitations of this method were also preliminarily investigated. These results broadened utility of N-Cbz protective group in synthetic chem., especially in synthesis or use of imidazole, benzimidazole, pyrazole or their derivatives The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Electric Literature of 73590-85-9

The Article related to imidazole pyrazole benzimidazole preparation, pyrazole imidazole benzimidazole benzyloxycarbonyl deprotection low carbon alc, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Electric Literature of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On March 16, 2018, Delsarte, Christine; Santraine, Romuald; Fours, Baptiste; Petit, Laurent published an article.Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole The title of the article was Metal-Free Synthesis of the Methanol Solvate of (S)-Omeprazole Potassium Salt Using (1R)-(-)-10-Camphorsulfonyloxaziridine: Oxidation Process Development and Optical Purity Enhancement Strategy. And the article contained the following:

The results of our process development studies to synthesize the methanol solvate of (S)-omeprazole potassium salt through the enantioselective oxidation of pyrmetazole using (1R)-(-)-10-camphorsulfonyloxaziridine are reported. Optical purity enhancement was achieved by means of a reslurry from methanol, the rationale and development details of which are also described. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

The Article related to pyrmetazole camphorsulfonyloxaziridine enantioselective oxidation, omeprazole potassium salt stereoselective preparation, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On January 31, 2008, Khomenko, T. M.; Volcho, K. P.; Komarova, N. I.; Salakhutdinov, N. F. published an article.Reference of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole The title of the article was An efficient procedure for the synthesis of Esomeprazole using a titanium complex with two chiral ligands. And the article contained the following:

A procedure has been proposed for the selective preparation of Esomeprazole [(S)-I] via asym. oxidation of the corresponding prochiral sulfide in the presence of a catalytic complex derived from titanium(IV) isopropoxide and two different chiral ligands, di-Et D-tartrate and (R)-N,N-dimethyl-1-phenylethanamine. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Reference of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

The Article related to asym preparation esomeprazole, titanium complex tartrate phenylethanamine asym preparation esomeprazole, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Reference of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On June 30, 2021, Zhao, Peng; Ren, Shi-Miao; Liu, Feng; Zheng, Yu-Cong; Xu, Na; Pan, Jiang; Yu, Hui-Lei; Xu, Jian-He published an article.Related Products of 73590-85-9 The title of the article was Protein engineering of thioether monooxygenase to improve its thermostability for enzymatic synthesis of chiral sulfoxide. And the article contained the following:

Esomeprazole, the S-enantiomer of omeprazole, is the best-selling proton pump inhibitor. In our previous work, a mutant of cyclohexanone monooxygenase from the Acinetobacter calcoaceticus (named AcCHMO-M6) was successfully obtained through protein engineering which could catalyze the oxidation of omeprazole sulfide. However, its practical application is still hindered by the poor thermostability, especially in the up-scaled reaction process. In this work, site mutagenesis based on consensus anal. and directed evolution were used to engineer this enzyme in order to improve the stability of AcCHMO-M6. The half-lives of the resultant mutants AcCHMO-M9 (F29L/R444E) and AcCHMO-M10 (F29L/R444E/A145S/G430T) at 40°C were increased from 2.2 h to 8.5 h and 5.9 h resp., while the corresponding Tm values were increased by 7°C and 5.3°C in comparison to AcCHMO-M6. The specific activity of AcCHMO-M9 was comparable to that of AcCHMO-M6, and the specific activity of AcCHMO-M10 was about 4-fold that of AcCHMO-M6. The AcCHMO-M10 catalyzed sulfide oxidation reaction reached 100% conversion after 16 h at 30°C, in contrast to 39.4% conversion in the case of AcCHMO-M6. These results show that the potential of this thioether monooxygenase can be significantly improved by protein engineering. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Related Products of 73590-85-9

The Article related to acinetobacter cyclohexanone monooxygenase protein engineering thermostability chiral sulfoxide, Fermentation and Bioindustrial Chemistry: Industrial Chemicals and other aspects.Related Products of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On August 31, 2015, Liu, Xiao-ping; Xu, Hui-lan; Sun, Rui; Li, Xue; Hu, Bao-hua; Hu, Chun published an article.Synthetic Route of 73590-85-9 The title of the article was Synthesis and characterization of two impurities in esomeprazole, an antiulcerative drug. And the article contained the following:

Impurity control is a key factor for drug quality. Study for impurities is helpful to optimize the production process and improve the quality of drugs. Synthesis and characterization of two of impurities in esomeprazole, which used for treatment of acid-related diseases was described in this paper. The two impurities are known as 2-[(3,5-dimethyl-4-methoxy-2-pyridinyl)methylsulfinyl]-1H-benzimidazole (impurity 1) and (R)-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole (esomeprazole impurity F), whose structures are characterized with MS, IR, 1H-NMR and elemental analyses, and the purities of the two impurities are above 99% by HPLC anal. The two target compounds can be used as the reference substance of the impurities of esomeprazole. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Synthetic Route of 73590-85-9

The Article related to antiulcerative drug esomeprazole impurity acid disease, Pharmacology: Other (All Agents and Effects Not Otherwise Assignable) and other aspects.Synthetic Route of 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On January 15, 2013, Si, Yuhui; Sun, Gangchun; Li, Zhicheng; Li, Yaping published an article.HPLC of Formula: 73590-85-9 The title of the article was Synthesis and resolution of omeprazole. And the article contained the following:

Omeprazole was synthesized and resolved by chiral resolution agent to obtain the S-isomer (Esomeprazole). The resolving conditions were as follows: S-(-)-1, 1′-Binaphthyl-2, 2′-diol, racemic omeprazole and alkali (molar ratio 1:1.6:1.8) reacted in ethanol and water (3.7:1 in v:v) at room temperature for 12 h. The magnesium salt of Esomeprazole was obtained in a high yield (89%) and excellent enantioselectivity (97.95% ee). The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).HPLC of Formula: 73590-85-9

The Article related to esomeprazole omeprazole synthesis chiral resolution, Pharmacology: Other (All Agents and Effects Not Otherwise Assignable) and other aspects.HPLC of Formula: 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On August 31, 2022, Xu, Xinqi; Zhang, Yajiao; Wang, Shaoyu; Xu, Lian; Su, Bingmei; Wang, Lichao; Lin, Juan published an article.SDS of cas: 73590-85-9 The title of the article was Nonpolarity paving in substrate tunnel of a Limnobacter sp. Phenylacetone monooxygenase for efficient single whole-cell synthesis of esomeprazole. And the article contained the following:

Baeyer-Villiger monooxygenase (BVMO) mediated sulfoxidation is a sustainable approach for the synthesis of esomeprazole. In this work, a novel phenylacetone monooxygenase from Limnobacter sp. (LnPAMO) was found to have trace activity for synthesis of enantiopure esomeprazole. Through engineering in the substrate tunnel using a mutagenesis strategy called “nonpolarity paving” and some modifications in cofactor binding domains, a mutant harboring 15 mutations (LnPAMO Mu15) was obtained with 6.6 x 103-fold higher activity to convert omeprazole sulfide into esomeprazole. The activities of the mutant for synthesis of (S)-Me Ph sulfoxide and (S)-pantoprazole also increased much, indicating the versatility of the mutant for sulfoxide synthesis. Importantly, no over-oxidation byproduct omeprazole sulfone was detected in the sulfoxidation products by both mass spectrometry and HPLC anal. Then NADP-dependent Burkholderia stabili formate dehydrogenase was ligated behind Mu15 along with a ribosome binding site sequence in pET-28a for co-expression. By single whole-cell of recombinant Escherichia coli BL21 coexpressing Mu15 and formate dehydrogenase, omeprazole sulfide was efficiently converted into esomeprazole without production of sulfone (16 g/L substrate, enantiomeric excess > 99.9% (S) and > 99% conversion) and the space-time-yield reached 1.67 g product/L/h. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).SDS of cas: 73590-85-9

The Article related to esomeprazole limnobacter phenylacetone monooxygenase whole cell synthesis, esomeprazole, phenylacetone monooxygenase, single-cell sulfoxidation, substrate tunnel, Fermentation and Bioindustrial Chemistry: Fermentation Engineering and other aspects.SDS of cas: 73590-85-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On November 30, 2011, Ogilvie, Brian W.; Yerino, Phyllis; Kazmi, Faraz; Buckley, David B.; Rostami-Hodjegan, Amin; Paris, Brandy L.; Toren, Paul; Parkinson, Andrew published an article.Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole The title of the article was The proton pump inhibitor, omeprazole, but not lansoprazole or pantoprazole, is a metabolism-dependent inhibitor of CYP2C19: implications for coadministration with clopidogrel. And the article contained the following:

As a direct-acting inhibitor of CYP2C19 in vitro, lansoprazole is more potent than omeprazole and other proton pump inhibitors (PPIs), but lansoprazole does not cause clin. significant inhibition of CYP2C19 whereas omeprazole does. To investigate this apparent paradox, we evaluated omeprazole, esomeprazole, R-omeprazole, lansoprazole, and pantoprazole for their ability to function as direct-acting and metabolism-dependent inhibitors (MDIs) of CYP2C19 in pooled human liver microsomes (HLM) as well as in cryopreserved hepatocytes and recombinant CYP2C19. In HLM, all PPIs were found to be direct-acting inhibitors of CYP2C19 with IC50 values varying from 1.2 μM [lansoprazole; maximum plasma concentration (Cmax) = 2.2 μM] to 93 μM (pantoprazole; Cmax = 6.5 μM). In addition, we identified omeprazole, esomeprazole, R-omeprazole, and omeprazole sulfone as MDIs of CYP2C19 (they caused IC50 shifts after a 30-min preincubation with NADPH-fortified HLM of 4.2-, 10-, 2.5-, and 3.2-fold, resp.), whereas lansoprazole and pantoprazole were not MDIs (IC50 shifts < 1.5-fold). The metabolism-dependent inhibition of CYP2C19 by omeprazole and esomeprazole was not reversed by ultracentrifugation, suggesting that the inhibition was irreversible (or quasi-irreversible), whereas ultracentrifugation largely reversed such effects of R-omeprazole. Under various conditions, omeprazole inactivated CYP2C19 with KI (inhibitor concentration that supports half the maximal rate of inactivation) values of 1.7 to 9.1 μM and kinact (maximal rate of enzyme inactivation) values of 0.041 to 0.046 min-1. This study identified omeprazole, and esomeprazole, but not R-omeprazole, lansoprazole, or pantoprazole, as irreversible (or quasi-irreversible) MDIs of CYP2C19. These results have important implications for the mechanism of the clin. interaction reported between omeprazole and clopidogrel, as well as other CYP2C19 substrates. The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

The Article related to omeprazole lansoprazole pantoprazole esomeprazole proton pump inhibitor interaction cyp2c19, Pharmacology: Effects Of Gastrointestinal and Respiratory Drugs and other aspects.Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On April 30, 2014, Zuo, Hui; Ma, Liangxiu published an article.Formula: C17H19N3O2S The title of the article was Study on green synthesis of omeprazole. And the article contained the following:

The aim is to study green synthesis of omeprazole. 4-Anisidine was treated via acetylation, nitration, hydrolysis, reduction and cyclization for synthesis of intermediate of 2-mercapto-5-methoxy-1H-benzimidazole. 2-Hydroxymethyl-3, 5-dimethyl-4-methoxy-pyridine was treated via sulfuryl chloride chlorination treatment to directly synthesize with benzimidazole to obtain intermediate of thioether without separation, and synthesis of omeprazole was achieved by catalytic oxidation The experimental process involved the reaction of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole(cas: 73590-85-9).Formula: C17H19N3O2S

The Article related to omeprazole green synthesis economic environment selective oxidation, Pharmacology: Effects Of Gastrointestinal and Respiratory Drugs and other aspects.Formula: C17H19N3O2S

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem