72830-07-0

Usage

Uses

Used in Pharmaceutical Industry:
3,4-DIMETHOXY-2-METHYLPYRIDINE N-OXIDE is used as a synthetic intermediate for the preparation of H+/K+-ATPase inhibitors. These inhibitors are essential in the development of medications that target gastric acid-related disorders, such as gastroesophageal reflux disease (GERD) and peptic ulcers.
Used in the Synthesis of 2-[2-(PYRIDYLMETHYL)THIO]-1H-BENZIMIDAZOLES:
3,4-DIMETHOXY-2-METHYLPYRIDINE N-OXIDE serves as a key component in the one-pot synthesis of 2-[2-(pyridylmethyl)thio]-1H-benzimidazoles. These compounds are valuable intermediates in the development of H+/K+-ATPase inhibitors, which are crucial for treating various gastric acid-related conditions.
Used as an Impurity in Pantoprazole (P183000):
3,4-DIMETHOXY-2-METHYLPYRIDINE N-OXIDE is also recognized as an impurity in the pharmaceutical compound Pantoprazole (P183000). Pantoprazole is a proton pump inhibitor (PPI) used to treat acid-related disorders, such as GERD, peptic ulcers, and other conditions that require the reduction of stomach acid. The presence of 3,4-DIMETHOXY-2-METHYLPYRIDINE N-OXIDE as an impurity highlights its relevance in the pharmaceutical industry and its potential impact on the efficacy and safety of Pantoprazole.

InChI:InChI=1/C8H11NO3/c1-6-8(12-3)7(11-2)4-5-9(6)10/h4-5H,1-3H3

Upstream product

• 17184-19-9 3-hydroxy-2-methylpyrid-4-one 
• 124-41-4 sodium methylate 
• 122307-41-9 4-chloro-3-methoxy-2-methylpyridine N-oxide 
• 4780-14-7 3-methoxy-2-methyl-4-pyrone 
• 118-71-8 Maltol 
• 67-56-1 methanol 
• 15931-25-6 3-methoxy-2-methyl-4-nitropyridine 1-oxide 
• 35392-65-5 3-methoxy-2-methylpyridine 1-oxide 
• 107512-34-5 4-Chloro-3-methoxy-2-methyl-pyridine 
• 76015-11-7 3-methoxy-2-methylpyridin-4(1H)-one 
• 107512-35-6 3,4-dimethoxy-2-methylpyridine 

Downstream Products

• 169905-10-6 2-(chloromethyl)-3,4-dimethoxypyridine 
• 102625-64-9 pantoprazole sulfide 
• 102625-70-7 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole 
• 72830-08-1 2-hydroxymethyl-3,4-dimethoxypyridine 
• 102625-99-0 2-acetoxymethyl-3,4-dimethoxypyridine 
• 72830-09-2 2-Chloromethyl-3,4-dimethoxy-pyridine; hydrochloride 

Relevant academic research and scientific papers

A pantoprazole intermediate 2 - chloromethyl - 3, 4 - dimethoxy pyridine hydrochloride preparation method

The invention belongs to the technical field of medicine, and particularly relates to a preparation method of a pantoprazole intermediate 2-chloromethyl-3,4-dimethoxy pyridine hydrochloride. The preparation method comprises the following steps: using 3-hydroxyl-2-methyl-4-pyrone as a starting raw material, and then only performing five-step reaction to obtain the pantoprazole intermediate 2-chloromethyl-3,4-dimethoxy pyridine hydrochloride. The preparation method reduces the reaction steps, shortens the reaction cycle, improves the working efficiency, and increases the yield coefficient.

Synthesis of a DOTA (Gd3+)-conjugate of proton-pump inhibitor pantoprazole for gastric wall imaging studies

Magnetic resonance imaging (MRI) is used to evaluate gastrointestinal (GI) structure and functions in humans. Despite filling the viscus lumen with a contrast agent, visualization of the viscus wall is limited. To overcome this limitation, we de novo synthesized a conjugate that covalently combines a Gd-based MRI contrast agent, encaged with a chelating agent (DOTA), with pantoprazole, which is a widely used proton pump inhibitor that binds to proton pumps in the stomach and colon. The DOTA linkage was installed at a mechanism-based strategic location in the pantoprazole molecule to minimize a possible negative effect of the structural modification on the drug. It is anticipated that by defining the wall of the stomach and colon, this compound will facilitate functional MRI of the GI tract in humans.

Diversified synthesis of novel quinoline and dibenzo thiazepine derivatives using known active intermediates

The novel drug development to control resisting infections in conventional drug therapy is a need of today. Few antiulcer relative derivatives developed by approaching convergent synthesis. The derivatives synthesized successfully are dibenzo thiazepine-pyridine (SLN11-SLN15) and benzimidazole-hydroquinoline based derivatives (SLN16-SLN20). It involved the coupling through microwave, sonication and conventional techniques at final step. The efficient technology identified as sonication technique basically time and yield. The reported compounds were structural characterized by elemental analysis and spectral studies such as 1H, 13C NMR and MS.

Structure-activity relationship of omeprazole and analogues as Helicobacter pylori urease inhibitors

Helicobacter pylori urease belongs to a family of highly conserved urea- hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K+-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K+- ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pK(a)-value of the pyridine, the pK(a)-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of β- mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 μmol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 μmol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.

(H+,K+)-ATPase inhibiting 2-[(2-pyridylmethyl)sulfinyl]benzimidazoles. 4. A novel series of dimethoxypyridyl-substituted inhibitors with enhanced selectivity. The selection of pantoprazole as a clinical candidate

[(Pyridylmethyl)sulfinyl]benzimidazoles 1 (PSBs) are a class of highly potent antisecretory (H+,K+)-ATPase inhibitors which need to be activated by acid to form their active principle, the cyclic sulfenamide 4. Selective inhibitors of the (H+,K+)-ATPase in vivo give rise to the nonselective thiophile 4 solely at low pH, thus avoiding interaction with other thiol groups in the body. The propensity to undergo the acid-catalyzed transformation is dependent on the nucleophilic/electrophilic properties of the functional groups involved in the formation of 2 since this step is both rate-determining and pH-dependent. The aim of this study was to identify compounds with high (H+,K+)-ATPase inhibitory activity in stimulated gastric glands possessing acidic pH, but low reactivity (high chemical stability) at neutral pH as reflected by in vitro (Na+,K+)-ATPase inhibitory activity. The critical influence of substituents flanking the pyridine 4-methoxy substituent present in all derivatives was carefully studied. The introduction of a 3-methoxy group gave inhibitors possessing a combination of high potency, similar to omeprazole and lansoprazole, but increased stability. As a result of these studies, compound 1a (INN pantoprazole) was selected as a candidate drug and is currently undergoing phase III clinical studies.

Fluoroalkoxy substituted benzimidazoles useful as gastric acid secretion inhibitors

Dialkoxypyridines of formula I STR1 wherein R1 is 1-3C-alkyl which is completely or predominantly substituted by fluorine, or a chlorodifluoromethyl radical and R1' is hydrogen, halo, trifluoromethyl, 1-3C-alkyl, or 1-3C-alkoxy which is optionally completely or predominantly substituted by fluorine, or R1 and R1', together with the oxygen atom to which R1 is bonded, are 1-2C-alkylenedioxy, which is optionally completely or partly substituted by fluorine, or chlorotrifluoroethylenedioxy, R3 is 1-3C-alkoxy, one of R2 and R4 is 1-3C-alkoxy and the other is a hydrogen atom or 1-3C-alkyl and n is 0 or 1, and salts thereof are new compounds with a pronounced protective action on the stomach. Processes for preparing these compounds, medicaments containing them and their use, as well as intermediate compounds and their use for preparing the subject dialkoxypyridines, are disclosed.

Picoline derivative useful as gastric acid secretion inhibitors

Picoline derivatives of the formula I STR1 wherein the substituents have the meanings given in the description, and their salts are new compounds having a pronounced protective action on the stomach.