86604-80-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Methoxy-2,3,5-trimethylpyride-N-oxide is used as an impurity in Omeprazole, which is a proton pump inhibitor. It plays a role in the development and formulation of this medication, which is used to inhibit gastric secretion and treat ulcers.
As an Antacid Agent:
4-Methoxy-2,3,5-trimethylpyride-N-oxide contributes to the overall effectiveness of Omeprazole as an antacid agent, helping to reduce stomach acid and alleviate symptoms associated with gastric ulcers and other gastrointestinal issues.

Upstream product

• 7722-84-1 dihydrogen peroxide 
• 109371-19-9 4-methoxy-2,3,5-trimethylpyridine 
• 75-09-2 dichloromethane 
• 74409-42-0 2,3,5-trimethylpyridine 1-oxide 
• 848694-11-1 4-bromo-2,3,5-trimethylpyridine-N-oxide 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 86604-79-7 2,3,5-trimethyl-4-nitropyridine N-oxide 
• 109371-20-2 4-chloro-2,3,5-trimethylpyridine 1-oxide 
• 109371-16-6 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 
• 109371-17-7 2,4-dichloro-3,5,6-trimethylpyridine 
• 109371-18-8 4-chloro-2,3,5-trimethylpyridine 
• 695-98-7 2,3,5-trimethyl-pyridine 

Downstream Products

• 86604-78-6 (4-methoxy-3,5-dimethylpyridin-2-yl)methanol 
• 86604-75-3 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 91219-90-8 (4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl acetate 
• 96300-88-8 2-Hydroxymethyl-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 73590-85-9 omeprazole sulfide 
• 122332-68-7 2-(4-Methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-6-(4-methoxy-phenyl)-3H-thieno[3,4-d]imidazole 
• 122307-88-4 2-(4-Methoxy-3,5-dimethyl-pyridin-2-ylmethylsulfanyl)-6-(4-methoxy-phenyl)-3H-thieno[3,4-d]imidazole 
• 122307-93-1 2-(4-Methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-6-phenyl-3H-thieno[3,4-d]imidazole 
• 122307-85-1 2-(4-Methoxy-3,5-dimethyl-pyridin-2-ylmethylsulfanyl)-6-phenyl-3H-thieno[3,4-d]imidazole 
• 84006-10-0 (chloromethyl)-4-methoxy-3,5-dimethylpyridine 
• 109371-19-9 4-methoxy-2,3,5-trimethylpyridine 

Relevant academic research and scientific papers

Synthesis method of 4-methoxy-2, 3, 5-trimethyl-pyridine nitrogen oxide

The invention discloses a synthesis method of 4-methoxy-2, 3, 5-trimethyl-pyridine nitrogen oxide, which comprises the following steps: S1, carrying out bromination reaction and methoxy substitution on 2, 3, 5-trimethylpyridine-N-oxide to obtain 4-bromine-2, 3, 5-trimethyl-pyridine nitrogen oxide; and S2, carrying out a sodium methoxide substitution reaction on the 4-bromo-2, 3, 5-trimethyl-pyridine nitrogen oxide to generate an important intermediate 4-methoxy-2, 3, 5-trimethyl-pyridine nitrogen oxide of omeprazole. According to the method, bromate and bromide which are mild bromination reaction conditions are adopted in the process route, then the bromate intermediate is used for carrying out methoxy substitution reaction, and the whole process is simple in design, mild in reaction condition and easy and convenient to operate.

Preparation method of 4-methoxy-2,3,5-trimethylpyridine

The invention belongs to the field of chemical intermediate preparation and specifically relates to a preparation method of 4-methoxy-2,3,5-trimethylpyridine. The preparation method comprises the following steps: 4-methoxy-2,3,5-trimethylpyridine-N-oxide is firstly obtained, and then 4-methoxy-2,3,5-trimethylpyridine is obtained. The preparation method has the characteristics of high yield, cheapraw material, simple process and good product quality. Thus, the preparation method has a certain application value.

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 2-[[(2-Pyridyl)methyl]thio]-1H- benzimidazoles as anti Helicobacter pylori agents in vitro and evaluation of their in vivo efficacy

A relationship between the structure of 21 2-[[(2-pyridyl)methyl]thio]- 1H-benzimidazoles (6) and their anti Helicobacter pylori activity expressed as minimum bactericidal concentration (MBC) values is described. Observed MBCs ranged from 256 to 1 μg/mL. The structure - activity relationship (SAR) showed that larger and more lipophilic compounds, especially compounds with such substituents in the 4-position of the pyridyl moiety, generally had lower MBC values. Four new compounds 'that were predicted to be potent by the established SAR model were synthesized and tested. One such compound, i.e., 2-[[(4-[(cyclopropylmethyl)oxy]3-methyl-2-pyridyl)methyl]thio]-1H- benzimidazole (18), was tested for in vivo efficacy in a mouse Helicobacter felis model (125 μmol/kg bid given orally for 4 days, n = 4). Unfortunately, antibacterial activity could not be clearly demonstrated in this model. Instead a potent acid secretion inhibition was observed. This finding was attributed to the methylthio compound being oxidized to the corresponding methyl sulfinyl derivative, i.e., a proton pump inhibitor, in vivo. Although the antibacterial activity had the potential of decreasing H. felis cell counts in vivo the proton pump inhibitory effect became dominant and actually promoted H. felis cell growth. Hence, we conclude that the antibacterial utility of the 2-[[(2-pyridyl)methyl]thio]1H-benzimidazoles (6) as a compound class is compromised by their propensity to become proton pump inhibitors upon metabolic oxidation in vivo.

1,3,4-oxadiazoles

1,3,4-oxadiazole compounds are disclosed. The subject compounds suppress immune function and have hepatoprotection activity.

(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.

Synthesis of 4-methoxy-2,3,5-trimethylpyridine: a specific building block for compounds with gastric-acid inhibiting activity.

A new synthesis of 4-methoxy-2,3,5-trimethylpyridine (2), an important building block for the preparation of gastric-acid inhibiting compounds, is described. Condensation of ethyl 3-amino-2-methyl-2-butenoate (3) and diethyl 2-methylmalonate (4) gives 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 5. Reaction of 5 with phosphoryl chloride affords 2,4-dichloro-3,5,6-trimethylpyridine (9a), which, upon hydrogenolysis with palladium on charcoal, gives 2,3,5-trimethylpyridine (10). However, selective hydrogenolysis in acidic solution yields 4-chloro-2-3-5-trimethylpyridine (11). Substitution of the chlorine in 11 with methoxide ion gives 4-methoxy-2,3,5-trimethylpyridine (2), which can be oxidized to the corresponding N-oxide (13). This constitutes a new and efficient route to compound 2 in an overall yield of 43%.

2,4-dichloro-3,5,6-trimethylpyridine

A method for the preparation of 2,3,5-trimethylpyridine and some of its derivatives.

(Bezimidazol-2-yl)-pyridinium compounds

(Benzimidazol-2-yl)-pyridinium compounds of the formula STR1 wherein A is --SR9, --SO3- or --S--SO3- ; R1 and R3 each is hydrogen or (C1 -C7)-alkyl; R2 is hydrogen, (C1 -C7)-alkyl, (C1 -C7)-alkoxy or a negatively charged oxygen atom; R4 is hydrogen or a negative charge; R5, R6, R7 and R8 each is hydrogen, (C1 -C7)-alkyl, aryl, halogen, cyano, nitro, formyl, (C2 -C7)-alkanoyl, arylcarbonyl, carboxy, carboxy-(C1 -C7)-alkyl, (C1 -C7)-alkoxycarbonyl, aryloxycarbonyl, aryl-(C1 -C7)-alkoxycarbonyl, (C1 -C7)-alkoxycarbonyl-(C1 -C7)-alkyl, carbamoyl, mono- or di-(C1 -C7)-alkylcarbamoyl, pyrrolidinocarbonyl, piperidinocarbonyl, carbamoyl-(C1 -C7)-alkyl, mono- or di-(C1 -C7)-alkylcarbamoyl-(C1 -C7)-alkyl, pyrrolidinocarbonyl-(C1 -C7)-alkyl, piperdinocarbonyl-(C1 -C7)-alkyl, hydroxy, (C1 -C7)-alkoxy, (C2 -C7)-alkanoloxy, aryloxy, arylcarbonyloxy, (C1 -C7)-alkoxycarbonyloxy, aryl-(C1 -C7)-alkoxycarbonyloxy, aryloxycarbonyloxy, carbamoyloxy, mono- or di-(C1 -C7)-alkylcarbamoyloxy, pyrrolidinocarbonyloxy, piperidinocarbonyloxy, hydroxy-(C1 -C7)-alkyl, trifluoromethyl, di-(C1 -C7)-alkoxymethyl or (C2 -C3)-alkylenedioxymethyl or two of these substituents which are adjacent jointly and together with the carbon atoms to which they are attached are a 5-, 6- or 7-membered ring; and R9 is (C1 -C20)-alkyl, (C3 -C7)-cycloalkyl, (C3 -C7)-alkenylalkyl, (C3 -C7)-alkynylalkyl, substituted (C3 -C7)- alkenyl-alkyl, aryl, aryl-(C1 -C7)-alkyl, hydroxy- (C2 -C7)-alkyl, (C1 -C7)-alkoxy- (C2 -C7)-alkyl, (C1 -C7)-alkoxycarbonyl- (C1 -C7)-alkyl, carboxy-(C1 -C7)-alkyl, di-(C1 -C7)-alkoxycarbonyl-(C2 -C7)-alkyl, dicarboxy-(C2 -C7)-alkyl, carboxy-(C1 -C7)-alkylcarbamoyl-(C1 -C7)-alkyl, optionally N-substituted amino-(C2 -C7)-alkyl, optionally N-substituted amino-carboxy-(C2 -C7)-alkyl, optionally N-substituted amino-(C1 -C7)-alkoxycarbonyl-(C2 -C7)-alkyl, heteroaryl, heteroaryl-(C1 -C7)-alkyl or a residue derived from a cysteine-containing oligopeptide by elimination of the SH group; provided that when there is a net single positive charge there is an external anion, or a pharmaceutically acceptable acid addition salt thereof.

Tricyclic imidazole derivatives

Tricyclic imidazole derivatives of formula I STR1 wherein one of R1 and R3 is lower alkyl and the other is hydrogen or lower alkyl, R2 is lower alkyl, n is the number 0 or 1, A is STR2 R4, R5, R6 and R7 each is lower alkyl and R8 is hydrogen or lower alkyl, and their acid addition salts are described. These compounds are useful as agents for control or prevention of ulcers and of increased gastric acid secretion.