Production Method 1

2243644-61-1

2243644-60-0

784143-42-6

89352-76-1

Reaction Conditions

1.1 Catalysts: Iron(III) acetylacetonate ,  2,4-Dichloro-6-[(E)-[[(1S)-1-(hydroxymethyl)-2,2-dimethylpropyl]imino]methyl]phe… Solvents: Ethyl acetate ;  30 min, 25 °C
1.2 Reagents: Benzoic acid, 4-(dimethylamino)-, lithium salt (1:1) Solvents: Ethyl acetate ;  30 min, 25 °C
1.3 Reagents: Hydrogen peroxide Solvents: Ethyl acetate ;  -7 °C; 2 min, -7 °C; 5.5 h, -7 °C

Reference

Synthesis of Esomeprazole and Related Proton Pump Inhibitors through Iron-Catalyzed Enantioselective Sulfoxidation

Nishiguchi, Shigenobu; Izumi, Takuhiro; Kouno, Takayoshi; Sukegawa, Junpei; Ilies, Laurean ; et al, ACS Catalysis, 2018, 8(10), 9738-9743

Production Method 2

73590-58-6

784143-42-6

89352-76-1

Reaction Conditions

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Dichloromethane ;  rt
1.2 Solvents: Water ;  30 min, rt

Reference

Chemistry of Covalent Inhibition of the Gastric (H+, K+)-ATPase by Proton Pump Inhibitors

Shin, Jai Moo; Cho, Young Moon; Sachs, George, Journal of the American Chemical Society, 2004, 126(25), 7800-7811

1-N-Methyl Omeprazole Raw materials

• Omeprazole
• 6-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1-methyl-1H-benzimidazole
• 1H-Benzimidazole, 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1-methyl-

1-N-Methyl Omeprazole Preparation Products

• 1-N-Methyl Omeprazole (784143-42-6)
• (5-Desmethoxy-6-methoxy) 1-N-Methyl Omeprazole (89352-76-1)

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Recent Advances in the Study of 1-N-Methyl Omeprazole (CAS: 784143-42-6)

1-N-Methyl Omeprazole (CAS: 784143-42-6) is a derivative of the well-known proton pump inhibitor (PPI) omeprazole, which is widely used in the treatment of gastrointestinal disorders such as acid reflux and peptic ulcers. Recent studies have focused on the synthesis, pharmacological properties, and potential therapeutic applications of this compound, aiming to enhance its efficacy and reduce side effects compared to its parent molecule. This research brief consolidates the latest findings on 1-N-Methyl Omeprazole, providing insights into its chemical characteristics, biological activity, and clinical relevance.

The synthesis of 1-N-Methyl Omeprazole involves the methylation of the nitrogen atom in the pyridine ring of omeprazole, resulting in a compound with altered pharmacokinetic and pharmacodynamic properties. Recent synthetic approaches have emphasized green chemistry principles, utilizing catalytic methods to improve yield and purity. Advanced analytical techniques, including high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy, have been employed to characterize the compound and ensure its structural integrity.

Pharmacological studies have demonstrated that 1-N-Methyl Omeprazole exhibits a higher binding affinity to the H+/K+-ATPase enzyme compared to omeprazole, leading to more potent inhibition of gastric acid secretion. In vitro and in vivo experiments have shown that this derivative has a prolonged half-life and improved metabolic stability, which could translate into better patient compliance and reduced dosing frequency. Additionally, preliminary data suggest that 1-N-Methyl Omeprazole may have a lower potential for drug-drug interactions, a common limitation of conventional PPIs.

Clinical investigations are currently underway to evaluate the safety and efficacy of 1-N-Methyl Omeprazole in human subjects. Early-phase trials have reported favorable tolerability profiles, with minimal adverse effects observed at therapeutic doses. Researchers are also exploring its potential applications beyond acid suppression, including anti-inflammatory and antioxidant effects, which could expand its therapeutic utility in conditions such as gastritis and Barrett's esophagus.

In conclusion, 1-N-Methyl Omeprazole represents a promising advancement in the field of acid-suppressive therapy. Its enhanced pharmacological properties and potential for broader clinical applications make it a compound of significant interest for future research. Ongoing studies will further elucidate its mechanisms of action and therapeutic benefits, paving the way for its potential introduction into clinical practice.

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