1604-14-4

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 45, p. 2484, 2002 DOI: 10.1021/jm0200660

InChI:InChI=1/C8H7Cl2NO2/c1-2-13-8(12)5-3-6(9)11-7(10)4-5/h3-4H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 42521-08-4 2,6-dichloroisonicotinoyl chloride 
• 7664-93-9 sulfuric acid 
• 5398-44-7 2,6-dichloropyridine-4-carboxylic acid 
• 99-11-6 citrazinic acid 
• 75308-46-2 tert-butyl 2,6-dichloropyridine-4-carboxylate 
• 101990-72-1 2,6-dichloro-pyridin-4-ylmethyl chloride 
• 87486-37-1 3,5-dichloro-1-phenylpyrazin-2(1H)-one 
• 623-47-2 propynoic acid ethyl ester 
• 125850-02-4 3,5-dichloro-2(H)-1,4-oxazin-2-one 

Downstream Products

• 101990-69-6 (2,6-dichloropyridin-4-yl)methanol 
• 439801-32-8 2-chloro-6-(5-cyano-2-benzyloxyphenoxy)pyridine-4-carboxylic acid ethyl ester 
• 294211-86-2 5,5''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester 
• 1186049-98-8 2-dimethylamino-6-phenoxy-N-(1-pyridin-3-ylmethyl-1H-pyrazol-3-yl)-isonicotinamide 
• 1186050-56-5 2-dimethylamino-6-phenoxy-isonicotinic acid ethyl ester 
• 1186050-57-6 2-dimethylamino-6-phenoxy-isonicotinic acid 
• 175204-45-2 4-(bromomethyl)-2,6-dichloropyridine 
• 95037-35-7 2-(2,6-dichloropyridin-4-yl)propan-2-ol 
• 1094759-12-2 2-chloro-6-(2-methoxyethoxy)isonicotinic acid 
• 1422195-47-8 2-(2-(3,4,5-trimethoxybenzylidene)hydrazinyl)-N'-(2,6-dichlorobenzylidene)-6-chloropyridine-4-carbohydrazide 
• 1422195-46-7 2-(2-(2-methoxybenzylidene)hydrazinyl)-N'-(2,6-dichlorobenzylidene)-6-chloropyridine-4-carbohydrazide 
• 1422195-45-6 2-(2-(2-chloro-6-flourobenzylidene)hydrazinyl)-N'-(2,6-dichlorobenzylidene)-6-chloropyridine-4-carbohydrazide 
• 1422195-44-5 2-(2-(3,4-dichlorobenzylidene)hydrazinyl)-N’-(2,6-dichlorobenzylidene)-6-chloropyridine-4-carbohydrazide 
• 1422195-43-4 2-(2-(2,6-dichlorobenzylidene)hydrazinyl)-N’-(2,6-dichlorobenzylidene)-6-chloropyridine-4-carbohydrazide 

Relevant academic research and scientific papers

FUSED PYRIMIDINE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF FIBROTIC DISEASES

The present invention discloses compounds according to Formula I: Wherein A, B, R1, R2, and Cy are as defined herein. The present invention relates to compounds inhibiting autotaxin (NPP2 or ENPP2), methods for their production, pharmaceutical compositions comprising the same, and methods of treatment using the same, for the prophylaxis and/or treatment of fibrotic diseases, proliferative diseases, inflammatory diseases, autoimmune diseases, respiratory diseases, cardiovascular diseases, neurodegenerative diseases, dermatological disorders, pain, and/or abnormal angiogenesis associated diseases by administering the compounds of the invention.

THIADIAZOLE MODULATORS OF S1P AND METHODS OF MAKING AND USING

The invention is directed to compounds of the formula: wherein each of the variables are defined herein, as well as methods of making and using the compounds as agonists of S1P1 and/or S1P5 for instance treating an autoimmune disease.

Synthesis and antimicrobial activities of some newly 2,4,6-tri-substituted pyridine derivatives

A series of novel 2-(2-(substituted benzylidene)hydrazinyl)-N'-(substituted benzylidene)-6-chloropyridine-4-carbohydrazide (5a-e), 2-(2- cycloalkylidenehydrazinyl)-6-chloro-N'-cyclo-alkylidenepyridine-4- carbohydrazide (6a,b), 2-(2-(1-(4-substituted phenyl)ethylidene)hydrazinyl)-6- chloro-N'-(1-(4-substituted phenyl)ethylidene)pyridine-4-carbohydrazide (7a,b) and 2-(2-(1-(pyridinyl)ethylidene)hydrazinyl)-6-chloro-N'-(1-(pyridinyl) ethylidene)pyridine-4-carbo-hydrazide (8a-c) derivatives have been synthesized by treating treating 2-chloro-6-hydrazinoisonicotinic acid hydrazide 4 with selected active reagents. Their structures were confirmed by spectral and analytical data. The synthesized compounds were investigated for antimicrobial activities. The antimicrobial screening showed that many of these obtained compounds have good activities comparable to Streptomycin and Fusidic acid as reference drugs. Springer Science+Business Media Dordrecht 2013.

BICYCLIC INHIBITORS OF ALK

The present invention relates to compounds of formula (1) or pharmaceutical acceptable salts, wherein R1, X, Y, Z, A, B, G1, and n are defined in the description. The present invention relates also to compositions containing said compounds which are useful for inhibiting kinases such as ALK and methods of treating diseases such as cancer.

PYRIDINE DERIVATIVES AS S1P1/EDG1 RECEPTOR MODULATORS

The invention relates to novel pyridine derivatives of formula (D, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents. Formula (I) wherein A represents and the other substituents are as defined in the claims.

Vectorial electron transfer in donor-photosensitizer-acceptor triads based on novel bis-tridentate ruthenium polypyridyl complexes

The first examples of rodlike donor-photosensitizer-acceptor arrays based on bis-2,6-di(quinolin-8-yl)pyridine RuII complexes 1a and 3a for photoinduced electron transfer have been synthesized and investigated. The complexes are synthesized in a convergent manner and are isolated as linear, single isomers. Time-resolved absorption spectroscopy reveals long-lived, photoinduced charge-separated states (τCSS (1a)=140 ns, τCSS (3a)=200 ns) formed by stepwise electron transfer. The overall yields of charge separation (≥50% for complex 1a and ≥95% for complex 3a) are unprecedented for bis-tridentate RuII polypyridyl complexes. This is attributed to the long-lived excited state of the [Ru(dqp)2]2+ complex combined with fast electron transfer from the donor moiety following the initial charge separation. The rodlike arrangement of donor and acceptor gives controlled, vectorial electron transfer, free from the complications of stereoisomeric diversity. Thus, such arrays provide an excellent system for the study of photoinduced electron transfer and, ultimately, the harvesting of solar energy.

AMINO-PYRIDINE DERIVATIVES AS S1P1 /EDG1 RECEPTOR AGONISTS

The invention relates to novel amino-pyridine derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.

PYRIDINE DERIVATIVES AS S1P1/EDG1 RECEPTOR MODULATORS

The invention relates to novel pyridine derivatives of formula (D, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents. Formula (I) wherein A represents and the other substituants are as defined in the claims.

Antianexiety activity of pyridine derivatives synthesized from 2-chloro-6-hydrazino-isonicotinic acid hydrazide

A series of oxadiazole pyridine derivatives were synthesized by using 2-chloro-6-hydrazinoisonicotinic acid hydrazide as starting material. Treatment of the hydrazide with carbon disulfide to afford the oxadiazole derivative, which was treated with 5-methyl-2-furancarbaldehyde, formic acid, acetic acid/acetic anhydride, or phthalic anhydride to yield the corresponding pyridinodiazoles and on imide. Condensation of the hydrazide with p-fluorobenzaldehyde in ethanol or acetic acid in the presence of sodium acetate afforded hydrazone and oxadiazole derivatives, which were acetylated and cyclized with acetic anhydride to N-acetyloxadiazole derivatives. The hydrazone was treated with acetic acid in the presence of sodium acetate, or bromine water/sodium acetate to give on oxadiazole, while it was cyclized with chloroacetyl chloride in the presence of TEA to oxoazetidinaminoisonicotinamide. Finally, condensation of the hydrazide with acid anhydrides in refluxing glacial acetic acid afforded the corresponding bisimide derivatives. The pharmacological screening showed that many of these obtained compounds have good antianexiety activity comparable to diazepam as positive control.

Synthesis, and analgesic and antiparkinsonian activities of thiopyrimidine, pyrane, pyrazoline, and thiazolopyrimidine derivatives from 2-chloro-6-ethoxy-4-acetylpyridine

A series of substituted pyridine derivatives were prepared from 2-chloro-6-ethoxy-4-acetylpyridine, which was prepared from the corresponding citrazinic acid as starting material. Reaction of acetylpyridine with thiophene-2-carboxaldehyde afforded the 2-chloro-6-ethoxy-4-β-(2-thienyl) acryloylpyridine, which was reacted with malononitrile in refluxing ethanol in the presence of piperidine as a catalyst to afford the cyanoaminopyrane derivative. Acryloylpyridine was treated with urea or guanidine hydrochloride in refluxing ethanolic potassium hydroxide to give the corresponding pyrimidinone and aminopyrimidine derivatives. The latter was condensed with hydrazine hydrate or phenyl hydrazine to give pyrazoline and N-phenylpyrazoline derivatives. Finally, cycloaddition reaction of acryloylpyridine with thiourea yielded thioxopyrimidine, which was treated with 2-bromopropionic acid, 3-bromopropionic acid, or bromoacetic acid to yield methylthiazolo-, thiazino-, and thiazolopyrimidine derivatives. The arylmethylene derivative was prepared by reacting thiazolopyrimidine with benzaldehyde or by reacting thioxopyrimidine with benzaldehyde and bromoacetic acid in one step. The pharmacological screening showed that many of these compounds have good analgesic and antiparkinsonian activities comparable to Valdecoxib and Benzatropine as reference drugs.