73590-85-9

Basic information

• Product Name: Ufiprazole
• Synonyms: H 168/22;5-METHOXY-2-(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL THIO-1H-BENZIMIDAZOLE;5-METHOXY-2-(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYLMERCAPTOBENZIMIDAZOLE;5-METHOXY-2-[[(3,5-DIMETHYL-4-METHOXY PYRIDINYL)-METHYL]THIO]-1H-BENZIMIDAZOLE;2-[(4-METHOXYETHOXY-3,5-DIMETHYL-2-PYRIDINYL)-METHYLTHIO]-5-METHOXYBENZIMIDAZOLE;2-{[(3,5-dimethyl-4-methoxy-2-pyridinyl)-methyl]-thio}-5-methoxy-1h-benzimidazole;OMEPRAZOLE SULPHIDE;ufiprazole
• CAS NO: 73590-85-9
• Molecular Formula: C₁₇H₁₉N₃O₂S
• Molecular Weight: 329.42
• EINECS: 208-591-9
• Product Categories: (intermediate of lamivudine);Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;zjh;Inhibitors
• Mol File: 73590-85-9.mol
• Article Data: 48

Chemical Properties

• Melting Point: 122.0 to 126.0 °C
• Boiling Point: 539.7 °C at 760 mmHg
• Flash Point: 280.2 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 1.03E-11mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.81±0.10(Predicted)
• CAS DataBase Reference: Ufiprazole(CAS DataBase Reference)
• NIST Chemistry Reference: Ufiprazole(73590-85-9)
• EPA Substance Registry System: Ufiprazole(73590-85-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 73590-85-9(Hazardous Substances Data)

Usage

Synthesis

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

Description

Omeprazole sulfide is an intermediate used in the production of the gastric proton pump inhibitors, omeprazole and esomeprazole . As a degradation product, it is reported to be a direct-acting inhibitor of cytochrome P450 2C19 in pooled human liver microsomes (IC50 = 9.7 μM).

Uses

Different sources of media describe the Uses of 73590-85-9 differently. You can refer to the following data:
1. A metabolite of Omeprazole
2. Omeprazole Sulfide (Esomeprazol EP Impurity C(Omeprazole EP Impurity C)) is a metabolite of Omeprazole.

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

• 102283-11-4 omeprazole-2-mercaptoethanol disulfide 
• 60-24-2 2-hydroxyethanethiol 
• 780752-32-1 4-methoxy-3,5-dimethyl-2-pyridinemethyl bromide 
• 37052-78-1 6-methoxy-1H-benzoimidazole-2-thiol 
• 220757-74-4 5-methoxy-2-{[(4-chloro-3,5-dimethyl-pyridin-2-yl)methyl]thio}-1H-benzimidazole 
• 124-41-4 sodium methylate 
• 102283-10-3 2-(2-hydroxyethyldisulfanylmethyl)-4-methoxy-1-(5-methoxybenzimidazol-2-yl)-3,5-dimethylpyridinium 
• 73590-58-6 omeprazole 
• 37052-78-1 2-Mercapto-5-methoxybenzimidazole 
• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 
• 73590-58-6 omeprazole 
• 86604-78-6 (4-methoxy-3,5-dimethylpyridin-2-yl)methanol 
• 233610-77-0 2-benzenesulfonyl-4-methoxy-3,5-dimethylpyridine 
• 91168-31-9 2-methylthio-5-methoxy-1H-benzimidazole 

Downstream Products

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

Relevant articles and documents

The Mechanism of Action of the Gastric Acid Secretion Inhibitor Omeprazole

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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.

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.

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)