696-08-2

Basic information

• Product Name: 4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE
• Synonyms: 4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE;4-Chloro-2-methylpyridine N-oxide;4-Chloro-2-picoline 1-oxide;4-chloro-2-methyl-1-oxidopyridin-1-ium;Pyridine,4-chloro-2-methyl-, 1-oxide
• CAS NO: 696-08-2
• Molecular Formula: C₆H₆ClNO
• Molecular Weight: 143.57094
• Mol File: 696-08-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE(696-08-2)
• EPA Substance Registry System: 4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE(696-08-2)

Safety Data

• Hazardous Substances Data: 696-08-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE is used as an intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into various drug molecules, contributing to their therapeutic properties.
Used in Agrochemical Industry:
4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE is used as an intermediate in the synthesis of agrochemicals to help develop compounds that can protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE is used as a building block in the production of various organic compounds, allowing for the creation of a wide range of chemical entities with diverse applications.
Used as a Reagent:
4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE can be used as a reagent in organic synthesis, facilitating specific chemical reactions and contributing to the formation of desired products.
Used as a Precursor:
4-CHLORO-2-METHYL-PYRIDINE 1-OXIDE is used as a precursor in the preparation of other chemical compounds, enabling the synthesis of more complex molecules for various applications.

Upstream product

• 5470-66-6 2-methyl-4-nitropyridine N-oxide 
• 75-36-5 acetyl chloride 
• 584-08-7 potassium carbonate 

Downstream Products

• 63071-10-3 (4-chloropyridin-2-yl)methanol 
• 63071-13-6 4-chloro-2-pyridinecarbaldehyde 
• 104711-65-1 4-chloro-6-methylpyridine-2-carbonitrile 

Relevant articles and documents

Discovery of N-(5-Fluoropyridin-2-yl)-6-methyl-4-(pyrimidin-5-yloxy)picolinamide (VU0424238): A Novel Negative Allosteric Modulator of Metabotropic Glutamate Receptor Subtype 5 Selected for Clinical Evaluation

Preclinical evidence in support of the potential utility of mGlu5 NAMs for the treatment of a variety of psychiatric and neurodegenerative disorders is extensive, and multiple such molecules have entered clinical trials. Despite some promising results from clinical studies, no small molecule mGlu5 NAM has yet to reach market. Here we present the discovery and evaluation of N-(5-fluoropyridin-2-yl)-6-methyl-4-(pyrimidin-5-yloxy)picolinamide (27, VU0424238), a compound selected for clinical evaluation. Compound 27 is more than 900-fold selective for mGlu5 versus the other mGlu receptors, and binding studies established a Ki value of 4.4 nM at a known allosteric binding site. Compound 27 had a clearance of 19.3 and 15.5 mL/min/kg in rats and cynomolgus monkeys, respectively. Imaging studies using a known mGlu5 PET ligand demonstrated 50% receptor occupancy at an oral dose of 0.8 mg/kg in rats and an intravenous dose of 0.06 mg/kg in baboons.

IMIDAZOPYRIDINE EZH2 INHIBITORS

The present invention relates to imidazopyridines of general formula (I), to a method for their preparation, to intermediates for their preparation, to pharmaceutical compositions comprising at least one of those compounds, and to the use thereof.

SUBSTITUTED 4-ALKOXYPICOLINAMIDE ANALOGS DS MGLUR5 NEGATIVE ALLOSTERIC MODULATORS

Disclosed are negative allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with glutamate dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

6-ALKYL-N-(PYRIDIN-2-YL)-4-ARYLOXYPICOLINAMIDE ANALOGS AS MGLUR5 NEGATIVE ALLOSTERIC MODULATORS AND METHODS OF MAKING AND USING THE SAME

Disclosed are negative allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with glutamate dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Molecular complexes of 4-nitropyridine and 4-nitroquinoline N-oxides with boron trifluoride and hydrogen chloride as intermediates in SNAr reactions

Complexation of 4-nitropyridine N-oxides with ν- (BF3, HCl) and π-acceptors (tetracyanoethylene, chloranil, 2,3-dichloro-5,6-dicyano-1,4- benzoquinone, 7,7,8,8-tetracyanoquinodimethane) activates the nitro group to nucleophilic replacement by chlorine. Adducts formed by 4-nitropyridine and 4-nitroquinoline N-oxides with boron trifluoride and hydrogen chloride were studied by IR spectroscopy. It was shown that these complexes belong to the n,ν type and that the donor-acceptor interaction therein involves the oxygen atom of the N-oxide group.

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.

Resonance Raman investigation of equatorial ligand donor effects on the CU2O22+ core in end-on and side-on μ-peroxo-dicopper(II) and bis-μ-oxo-dicopper(III) complexes

The effect of endogenous donor strength on CU2O2 bonds was studied by electronically perturbing [{(R-TMPA)CuII}2(O2)]2+ and [{(R-MePY2)Cu}2(O2)]2+ (R = H, MeO, Me2N), which form the end-on μ-1,2 bound peroxide and an equilibrium mixture of side-on peroxo- dicopper(II) and bis-μ-oxo-dicopper(III) isomers, respectively. For [{(R-TMPA)CUII}2(O2)]2+, vo-o shifts from 827 to 822 to 812 cm-1 and VCu-O(sym) shifts from 561 to 557 to 551 cm-1, respectively, as R- varies from H to MeO to Me2N. Thus, increasing the N-donor strength to the copper decreases peroxide π*σ donation to the copper, weakening the Cu-O and O-O bonds. A decrease in vCu-O of the bis-μ-oxo- dicopper(III) complex was also observed with increasing N-donor strength for the R-MePY2 ligand system. However, no change was observed for vO-O of the side-on peroxo. This is attributed to a reduced charge donation from the peroxide π*σ orbital with increased N-donor strength, which increases the negative charge on the peroxide and adversely affects the back-bonding from the Cu to the peroxide σ*orbital. However, an increase in the bis-μ-oxo-dicopper(III) isomer relative to side-on peroxo-dicopper(II) species is observed for R-MePY2 with R = H 2N. This effect is attributed to the thermodynamic stabilization of the bis-μ-oxo-dicopper(III) isomer relative to the side-on peroxo-dicopper(II) isomer by strong donor ligands. Thus, the side-on peroxo-dicopper(II)/bis-μ-oxo-dicopper(III) equilibrium can be controlled by electronic as well as steric effects.

Superoxide dismutase activity of iron(II)TPEN complex and its derivatives

Superoxide is involved in the pathogenesis of various diseases, such as inflammation, ischemia-reperfusion injury and carcinogenesis. Superoxide dismutases (SODs) catalyze the disproportionation reaction of superoxide to produce oxygen and hydrogen peroxide, and can protect living cells against the toxicity of free radicals derived from oxygen. Thus, SODs and their functional mimics have potential value as pharmaceuticals. We have previously reported that Fe(II)tetrakis-N,N,N',N'-(2-pyridylmethyl)ethylenediamine (Fe(II)TPEN) has an excellent SOD activity (IC50=0.5 μM) among many iron complexes examined (J. Biol. Chem., 264, 9243-9249 (1989)). Fe(II)TPEN can act like native SOD in living cells, and protect Escherichia coli cells from free radical toxicity caused by paraquat. In order to develop more effective SOD functional mimics, we synthesized Fe(II)TPEN derivatives with electron-donating or electron-withdrawing groups at the 4-position of all pyridines of TPEN, and measured the SOD activities and the redox potentials of these complexes. Fe(II) tetrakis-N,N,N',N'-(4-methoxy-2-pyridylmethyl)ethylenediamine (Fe(II)(4MeO)4TPEN) had the highest SOD activity (IC50=0.1 μM) among these iron-based SOD mimics. In addition, a good correlation was found between the redox potential and the SOD activity of 15 Fe(II) complexes, including iron-based SOD mimics reported in the previous paper (J. Organometal. Chem., in press). Iron-based SOD mimics may be clinically applicable, because these complexes are generally tissue-permeable and show low toxicity. Therefore our findings should be significant for the development of clinically useful SOD mimics.

Substituted thienoimidazole derivatives

Substituted thienoimidzaole derivatives, processes for their preparation, pharmaceutical preparations containing them and their use as inhibitors of gastric acid secretion. The invention relates to substituted thienoimidazole derivatives of the formula STR1 in which A stands for STR2 T denotes --S--, --SO-- or --SO2 --, R7 denotes a substituted aryloxy or aralkoxy radical and R1, R2, R3, R4, R5, R6 and R8 have the meanings indicated in the description, processes for their preparation, pharmaceutical preparations containing them and their use as medicaments.

PYRIDINE DERIVATIVES HAVING ANTI-ULCERATIVE ACTIVITY

Pyridine derivatives useful for preventing or treating peptic ulcers, pharmaceutical preparations and methods of treating peptic ulcers are described.