86604-79-7

Usage

Uses

Used in Pharmaceutical Industry:
4-NITRO-2,3,5-TRIMETHYLPYRIDINE-N-OXIDE is used as an impurity in Omeprazole, a proton pump inhibitor that covalently binds to the enzyme and inhibits gastric acid secretion. This helps in the treatment of gastric ulcers and other gastrointestinal conditions by reducing the acidity in the stomach.
Used as an Antacid:
4-NITRO-2,3,5-TRIMETHYLPYRIDINE-N-OXIDE, as a component of Omeprazole, is used as an antacid to alleviate symptoms associated with excess stomach acid, such as heartburn, indigestion, and acid reflux. Its presence in Omeprazole contributes to the overall effectiveness of the medication in managing these conditions.

InChI:InChI=1/C8H10N2O3/c1-5-4-9(11)7(3)6(2)8(5)10(12)13/h4H,1-3H3

Upstream product

• 74409-42-0 2,3,5-trimethylpyridine 1-oxide 
• 695-98-7 2,3,5-trimethyl-pyridine 

Downstream Products

• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 
• 109371-20-2 4-chloro-2,3,5-trimethylpyridine 1-oxide 
• 149082-03-1 2-hydroxymethyl-3,5-dimethyl-4-nitropyridine 
• 153476-68-7 2-chloromethyl-3,5-dimethyl-4-nitro-pyridine 
• 142885-91-4 5-methoxy-2-(((3,5-dimethyl-4-nitro-2-pyridinyl)methyl)thio)-1H-benzimidazole 
• 142885-96-9 2-chloromethyl-4-chloro-3,5-dimethylpyridine 
• 109371-18-8 4-chloro-2,3,5-trimethylpyridine 
• 86604-75-3 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 91219-90-8 (4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl acetate 
• 86604-78-6 (4-methoxy-3,5-dimethylpyridin-2-yl)methanol 
• 113618-23-8 Phenyl-(2,3,5-trimethyl-pyridin-4-yl)-amine 
• 943315-18-2 2-bromomethyl-4-cyano-3,5-dimethylpyridine 
• 943315-15-9 acetic acid 4-cyano-3,5-dimethylpyridin-2-ylmethyl ester 

Relevant academic research and scientific papers

4-nitro-2,3,5-trimethylpyridine-N-oxide preparation method

The invention belongs to the field of preparation of chemical industry intermediates, and particularly relates to a 4-nitro-2,3,5-trimethylpyridine-N-oxide preparation method, which comprises: obtaining a 2,3,5-trimethylpyridine-N-oxide, and obtaining a 4-nitro-2,3,5-trimethylpyridine-N-oxide. According to the present invention, the preparation method has characteristics of high yield, low raw material cost, simple treatment and good product quality, and is suitable for industrial production.

Discovery and crystallography of bicyclic arylaminoazines as potent inhibitors of HIV-1 reverse transcriptase

Non-nucleoside inhibitors of HIV-1 reverse transcriptase (HIV-RT) are reported that incorporate a 7-indolizinylamino or 2-naphthylamino substituent on a pyrimidine or 1,3,5-triazine core. The most potent compounds show below 10 nanomolar activity towards wild-type HIV-1 and variants bearing Tyr181Cys and Lys103Asn/Tyr181Cys resistance mutations. The compounds also feature good aqueous solubility. Crystal structures for two complexes enhance the analysis of the structure-activity data.

BENZIMIDAZOLE COMPOUND HAVING GASTRIC ACID SECRETION INHIBITORY ACTIVITY

The present invention provides a compound that has superior gastric acid secretion inhibitory action, ample long-lasting gastric acid secretion inhibitory action, and is able to maintain intragastric pH at a high level for an extended period of time, making it useful as a therapeutic or prophylactic agent for diseases or symptoms caused by gastric acid, as well as an active form of this compound (form to which the compound is converted in the body following administration thereof) in the form of a compound represented by general formula (1 a) (wherein R2 represents a group represented by formula (I) or the like, and R1, R3, W1 and X- are as defined in the description).

SALT OF SULFINYLBENZIMIDAZOLE COMPOUND, AND CRYSTAL AND AMORPHOUS FORM THEREOF

Salts of 2-[({4-[(2.2-dimethyl-1,3-dioxan-5-yl)methoxy]-3,5-dimethylpyridin-2-yl}methyl)sulfinyl]-1H-benzimidazole and their crystalline and amorphous forms.

STABILIZED COMPOSITION

It is intended to provide a pharmaceutical composition which contains a proton pump inhibitor and is stable even if it is stored for a long time. It is also intended to provide a pharmaceutical composition which contains a proton pump inhibitor susceptible to acid, and does not dissolve in the stomach but dissolves in the intestine to release a primary drug product promptly. The object could be achieved by the pharmaceutical composition characterized in that a layer containing a proton pump inhibitor and ethyl cellulose, a layer containing an enteric polymer, and if necessary an intermediate layer composed of one or more layers are formed on a pharmacologically inactive core substance. The intermediate layer is composed of a water-insoluble polymer, a water-soluble polymer, a lubricant and the like.

PROCESS FOR THE PRODUCTION OF 2- [ [4- T (2, 2-DIMETHYL-1, 3-DIOXAN-5-YL) METHOXY] PYRIDIN-2-YL] METHYLTHIO] -1H-BENZIMIDAZOLE

It is an object of the present invention to provide a process for the production on an industrial scale of a compound (1) or a salt thereof. There is provided a process for the production of compound (1) represented by the formula or a salt thereof: (wherein R1 and R3 independently represents a hydrogen atom or a methyl group), the process comprising the steps of: (a) reacting together a compound (3T) represented by the formula: (wherein X1 represents a leaving group, and R1 and R3 are defined as above) and (2,2-dimethyl-1,3-dioxan-5-yl)methanol represented by the formula or a salt thereof: so as to produce a compound (2T) represented by the formula (wherein R1 and R3 are defined as above); and (b) reacting the compound represented by above formula (2T) with an oxidizing agent.

Rationally designed high-affinity 2-amino-6-halopurine heat shock protein 90 inhibitors that exhibit potent antitumor activity

Heat shock protein 90 (Hsp90) is a molecular chaperone protein implicated in stabilizing the conformation and maintaining the function of many cell-signaling proteins. Many oncogenic proteins are more dependent on Hsp90 in maintaining their conformation, stability, and maturation than their normal counterparts. Furthermore, recent data show that Hsp90 exists in an activated form in malignant cells but in a latent inactive form in normal tissues, suggesting that inhibitors selective for the activated form could provide a high therapeutic index. Hence, Hsp90 is emerging as an exciting new target for the treatment of cancer. We now report on a novel series of 2-amino-6-halopurine Hsp90 inhibitors exemplified by 2-amino-6-chloro-9-(4-iodo-3,5-dimethylpyridin- 2-ylmethyl)purine (30). These highly potent inhibitors (IC50 of 30 = 0.009 μM in a HER-2 degradation assay) also display excellent antiproliferative activity against various tumor cell lines (IC50 of 30 = 0.03 μM in MCF7 cells). Moreover, this class of inhibitors shows higher affinity for the activated form of Hsp90 compared to our earlier 8-sulfanylpurine Hsp90 inhibitor series. When administered orally to mice, these compounds exhibited potent tumor growth inhibition (>80%) in an N87 xenograft model, similar to that observed with 17-allylamino-17- desmethoxygeldanamycin (17-AAG), which is a compound currently in phase I/II clinical trials.

Benzimidazole compound

An object of the present invention is to provide a novel chemical compound useful as a therapeutic or prophylactic agent for acid-related diseases, having an excellent inhibitory effect against gastric acid secretion, an excellent effect of maintaining the inhibitory effect against gastric acid secretion, thereby maintaining intragastric pH high for a long time, and having more safety and appropriate physicochemical stability. Provided is a compound represented by where R1 and R3 may be the same or different and each represent a hydrogen atom or a C1-C6 alkyl group; R2 represents (5,5-dimethyl-1,3-dioxan-2-yl)methoxy group, 5,7-dioxaspiro[2.5]oct-6-ylmethoxy group, 1,5,9-trioxaspiro[5.5]undec-3-ylmethoxy group, or (2,2-dimethyl-1,3-dioxan-5-yl)methoxy group; R4, R5, R6 and R7 represent a hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group or C1-C6 haloalkoxy group; and W1 represents a single bond, methylene or ethylene group, a salt thereof or a solvate of these.

Inhibitors of the gastric H+, K+-atpase with enhanced therapeutic properties

Chemical syntheses and medical uses of novel inhibitors of the gastric H+, K+-ATPase for the treatment and/or management of duodenal ulcers, heartburn, acid reflux, other conditions mediated by gastric acid secretion and/or psoriasis are described.

NOVEL HETEROCYCLIC COMPOUNDS AS HSP90-INHIBITORS

Novel heterocyclic compounds are described and demonstrated to have utility as Heat Shock Protein 90 (HSP90) inhibiting agent. Method of synthesis and use of such compounds are also described.