73590-85-9

Usage

Uses

Used in Pharmaceutical Industry:
Ufiprazole is used as a metabolite of Omeprazole for its role in the production of gastric proton pump inhibitors, which are essential in treating various gastrointestinal disorders. Its presence as a degradation product also contributes to the overall efficacy and safety profile of the final drug products.
Used in Drug Metabolism Studies:
Ufiprazole is used as a research compound in drug metabolism studies, particularly focusing on its inhibitory effects on cytochrome P450 2C19. This information is crucial for understanding drug interactions and optimizing dosing regimens for patients.

Synthesis

Ufiprazole can be synthesized by the condensation reaction of 2-mercapto-5-methoxybenzimidazole and 2-chloromethyl-4-methoxy-3,5-lutidine.

Biological Activity

Ufiprazole (Omeprazole sulfide) is an intermediate in the production of gastric proton pump inhibitors omeprazole and esomeprazole.

InChI:InChI=1/C17H19N3O2S/c1-10-8-18-15(11(2)16(10)22-4)9-23-17-19-13-6-5-12(21-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)

Upstream product

• 102283-10-3 2-(2-hydroxyethyldisulfanylmethyl)-4-methoxy-1-(5-methoxybenzimidazol-2-yl)-3,5-dimethylpyridinium 
• 102283-11-4 omeprazole-2-mercaptoethanol disulfide 
• 60-24-2 2-hydroxyethanethiol 
• 73590-58-6 omeprazole 
• 96-96-8 4-methoxy-2-nitroaniline 
• 37052-78-1 2-Mercapto-5-methoxybenzimidazole 
• 84006-10-0 (chloromethyl)-4-methoxy-3,5-dimethylpyridine 
• 220757-74-4 5-methoxy-2-{[(4-chloro-3,5-dimethyl-pyridin-2-yl)methyl]thio}-1H-benzimidazole 
• 124-41-4 sodium methylate 
• 142885-91-4 5-methoxy-2-(((3,5-dimethyl-4-nitro-2-pyridinyl)methyl)thio)-1H-benzimidazole 
• 86604-75-3 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 233610-77-0 2-benzenesulfonyl-4-methoxy-3,5-dimethylpyridine 
• 91168-31-9 2-methylthio-5-methoxy-1H-benzimidazole 
• 86604-78-6 (4-methoxy-3,5-dimethylpyridin-2-yl)methanol 

Downstream Products

• 73590-58-6 omeprazole 
• 119141-88-7 (S)-6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]-sulfinyl]-1H-benzimidazole 
• 119141-89-8 (R)-6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1H-benzoimidazole 
• 88546-55-8 omeprazole sulfone 
• 103876-98-8 2-{[(6-methoxy-1H-benzimidazol-2-yl)thio]methyl}-3,5-dimethyl-4-pyridinol 
• 73590-58-6 omeprazole 
• 119141-88-7 esomeprazole 
• 149-57-5 2-Ethylhexanoic acid 
• 119141-89-8 (R)-omeprazole 
• 161973-11-1 esomeprazole magnesium 

Relevant academic research and scientific papers

Coupling and optimisation of online nuclear magnetic resonance spectroscopy and mass spectrometry for process monitoring to cover the broad range of process concentration

Real time online monitoring of chemical processes can be carried out by a number of analytical techniques, including optical and vibrational spectroscopies, nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). As each technique has unique advantages and challenges, combinations are an attractive option. The combination of a 500-MHz 1H NMR and a small footprint mass spectrometer to monitor a batch reaction at process concentration was investigated. The mass spectrometer was coupled into the flow path of an online reaction monitoring NMR. Reaction mixture was pumped from a 100-ml vessel to an NMR flow tube before returning to the vessel. Small aliquots were diverted into a sampling make-up flow using an active flow splitter and passed to the mass spectrometer. Advantages of the combination were observed. 1H NMR was ideal for quantitation of high level components, whereas MS showed a greater capability for detecting those at low level. In preliminary experiments MS produced a limited linear relationship with concentration (0.02% to 2% relative concentration, 0.01 mg/ml–1.25 mg/ml), because of signal saturation at the higher concentrations. NMR was unable to detect components below 0.1% relative to concentration maximum. Optimisation of sample transfer to the MS extended the linearity to 10% relative to the concentration maximum. Therefore, the combination of online NMR and MS allows both qualitative and quantitative analysis of reaction components over the full process range. The application of the combination was demonstrated by monitoring a batch chemical reaction and this is described. Copyright

Synthetic method and application of omeprazole

The invention belongs to the field of medicine synthesis, and discloses a synthetic method of omeprazole. The synthetic method comprises the following steps: reacting sodium (4-methoxy-3, 5-dimethyl pyridine-2-yl) methanesulfinate to generate (4-methoxy-3, 5-dimethyl pyridine-2-yl) methanesulfinic acid acyl chloride, and then carrying out Suzuki reaction on the (4-methoxy-3, 5-dimethyl pyridine-2-yl) methanesulfinic acid acyl chloride and (6-methoxy-1H-benzo [d] imidazole-2-yl) boric acid to generate omeprazole. According to the synthetic method of omeprazole, the omeprazole which is easy to purify and stable in yield is obtained by using raw materials which are easy to obtain, and a synthetic method which is simple, easy to operate and control, mild in reaction condition and capable of replacing high-risk reagents such as butyl lithium and the like by using a common reagent. The invention also provides an application of the synthetic method of omeprazole. The synthetic method is suitable for synthesis of omeprazole. The obtained omeprazole is used for preparing an omeprazole injection.

Synthesis method of esomeprazole sodium

The invention discloses a synthesis method of esomeprazole sodium. Belong to organic synthesis field. Of 5 - methoxy -2-mercaptobenzimidazole in ethanol - sodium hydroxide solution react with 2 - chloromethyl -3 and 5 -dimethyl -4 - methoxypyridine hydrochloride to obtain omeprazole thioether. The synthetic method is high in raw material utilization rate, reduces the content and kinds of impurities, greatly improves the extraction rate of esomeprazole sodium, can reach 75%, and has a purity of more than 99%. The synthetic route is short, and the synthesis cost is greatly reduced.

Synthetic method of esomeprazole

The invention discloses a synthetic method of esomeprazole, which comprises the following steps: first steps of preparation of omeprazole thioether. 2nd: The crude product is prepared by taking omeprazole thioether and the like as a raw material. The obtained crude product was subjected to a purification operation 3 times to give a refined intermediate. The third Steps. The purified intermediate is mixed with deionized water, filtered, mixed with magnesium chloride hexahydrate and deionized water, stirred, cooled, stirred 30 min, decompressed and suction filtered, and the obtained crystals are washed with distilled water and dried to obtain esomeprazole. Under the condition of ensuring 90%, the yield and purity of the subsequent processing process are improved, and the problems that in the prior art, the purity is not ideal, the total yield is low, the production cost is increased, and the industrial production is not conducive to industrial production are solved.

Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides

Herein, we describe a selective late-stage deoxygenation of sulfoxides based on a novel application of chlorosulfonium salts and demonstrate a new process using these species generated in situ from sulfoxides as the source of electrophilic chlorine. The use of highly nucleophilic 1,3,5-trimethoxybenzene (TMB) as the reducing agent is described for the first time and applied in the deoxygenation of simple and functionalized sulfoxides. The method is easy to handle, economic, suitable for gram-scale operations, and readily applied for poly-functionalized molecules, as demonstrated with more than 45 examples, including commercial medicines and analogues. We also report the results of competition experiments that define the more reactive sulfoxide and we present a mechanistic proposal based on substrate and product observations.

Preparation method of esomeprazole magnesium trihydrate (by machine translation)

The preparation method of the esomeprazole magnesium trihydrate, comprises the following steps :1): extracting 5 - methoxyl - 2 2-mercaptobenzimidazole and 2 - chloromethyl - 3333,5-dimethyl - 4 4-methoxyl pyridine hydrochloride to form omeprazole sodium salt ;2) by carrying out suction filtration drying, to form omeprazole (omeprazole) chiral compound, and adding an inorganic base organic solution, to an inorganic base organic solution . The preparation method has the advantages of high product, purity ;3) yield, simple, process, high ;4) efficiency, low cost and the like obtained in step, by suction filtration. 3). The preparation method comprises the following steps: dissolving omeprazole sodium salt ;5) with an organic solvent, and carrying out a suction filtration drying step 4); and carrying out suction filtration on omeprazole, and adding an inorganic oxidizing, agent to the inorganic base organic solution, layer, by a suction filtration drying, process ;6) to form the esomeprazole, sodium, salt solution layer by a. centrifugal, drying ;7) preparation method, and a preparation method of the esomeprazole, inorganic salt solution layer are carried out in an unsymmetrical oxidation reaction 6). (by machine translation)

Preparation method of esomeprazole sodium

The invention provides a preparation method of esomeprazole sodium, specifically a preparation method of optically pure esomeprazole sodium. The preparation method comprises the step of preparing esomeprazole sodium by taking 2-mercapto-5-methoxy-1H-benzimidazole and 2-chloromethyl-4-methoxy-3,5-dimethyl pyridine hydrochloride as starting raw materials. The method provided by the invention has good selectivity, can obtain almost optically pure products, and is suitable for industrial production of esomeprazole sodium.

Synthesis method of esomeprazole serving as proton pump inhibitor

The invention discloses a synthesis method of esomeprazole serving as a proton pump inhibitor, and belongs to the technical field of drug synthesis. According to the method, asymmetric oxidation on isconducted on omeprazole thioether under the condition that chiral phosphoric acid serves as a catalyst and hydrogen peroxide serves as an oxidizing agent to generate esomeprazole. Firstly, 5-methoxy-2-benzimidazolethiol and 2-chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride generate omeprazole thioether in an aqueous phase, and then selective oxidation is conducted on omeprazole in the presence of a chiral phosphoric acid catalyst to generate esomeprazole. The method has the advantages of being high in yield, environmentally friendly, good in selectivity, free of heavy metal residuesand more suitable for large-scale industrial production.

Preparation method of esomeprazole thioether

The invention relates to the technical field of drug synthesis, and provides a preparation method of esomeprazole thioether. The method comprises the steps of condensing 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride and 2-mercapto-5-methoxy-1H-benzimidazole as raw materials, concentrating condensation reaction liquid, extracting a product into an organic phase by methanol replacementand phase splitting, then concentrating the organic phase, replacing a residual solvent with acetone, and then adding the acetone for cooling crystallization. By utilizing the principle of mutual dissolution of the acetone and water, the crystallization is carried out in an acetone environment, so that the water content of the product during crystallization is reduced and then the esomeprazole thioether with the water content lower than 0.2% is obtained; and the preparation method has high process reproducibility and is suitable for large-scale production.

A preparation method of esomeprazole magnesium

The invention relates to the field of chemical synthesis, in particular to a novel synthesis process for active pharmaceutical ingredients of a PPI (proton pump inhibitor), and especially relates to a preparation method of esomeprazole magnesium. According to the method, 5-methoxy-2-mercaptobenzimidazole and 2-chloromethyl-3,5-dimethyl-4-methoxy pyridine hydrochloride are taken as the starting raw materials and subjected to condensation, asymmetric oxidation and salifying to prepare esomeprazole magnesium, a wet product is refined with water and methanol, an intermediate does not require crystallization, filtering and drying, the operation steps are simplified, the production cycle is shortened, material loss and energy consumption in a processing process are reduced, the yield is improved, and good economic benefits and social benefits are realized. The preparation method is good in repeatability and simple to operate, improves the yield and purity of esomeprazole magnesium and facilitates industrial production.