123696-02-6

Basic information

• Product Name: 3-CHLORO-5-METHOXYPYRIDAZINE
• Synonyms: 3-CHLORO-5-METHOXYPYRIDAZINE;3-Chloro-5-methoxypyridazine, HCl salt;3-Chloro-5-Methoxypyridazine HCl
• CAS NO: 123696-02-6
• Molecular Formula: C₅H₅ClN₂O
• Molecular Weight: 144.56
• EINECS: 200-001-2
• Mol File: 123696-02-6.mol

Chemical Properties

• Boiling Point: 285 ºC
• Flash Point: 126 ºC
• Appearance: /
• Density: 1.292
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.52
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.45±0.10(Predicted)
• CAS DataBase Reference: 3-CHLORO-5-METHOXYPYRIDAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-5-METHOXYPYRIDAZINE(123696-02-6)
• EPA Substance Registry System: 3-CHLORO-5-METHOXYPYRIDAZINE(123696-02-6)

Safety Data

• Hazardous Substances Data: 123696-02-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-5-methoxypyridazine is used as a key intermediate in the synthesis of potent and selective inhibitors of glycogen synthase kinase 3 (GSK-3) for the development of new therapeutic agents. GSK-3 is a serine/threonine protein kinase that plays a crucial role in various cellular processes, including glycogen synthesis, cell cycle regulation, and apoptosis. Inhibition of GSK-3 has been linked to the treatment of several diseases, such as Alzheimer's, diabetes, and cancer.
The compound's application in the pharmaceutical industry is primarily due to its ability to be incorporated into the molecular structure of GSK-3 inhibitors, which can exhibit good cellular efficacy. This makes 3-chloro-5-methoxypyridazine a valuable building block for the design and development of novel therapeutics targeting GSK-3-related conditions.

InChI:InChI=1/C5H5ClN2O/c1-9-4-2-5(6)8-7-3-4/h2-3H,1H3

Upstream product

• 123696-01-5 3-methoxy-3(2H)-pyridazinone 
• 7732-18-5 water 
• 152732-22-4 4-bromo-5-methoxypyridazin-3(2H)-one 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 1837-55-4 3,5-dichloropyridazine 
• 173206-12-7 4-chloro-5-methoxy-2-(tetrahydro-2H-pyran-2-yl)-3(2H)-pyridazinone 
• 173206-14-9 5-methoxy-2-(tetrahydro-2H-pyran-2-yl)-3(2H)-pyridazinone 
• 63910-43-0 4-chloro-5-methoxypyridazin-3-(2H)-one 

Downstream Products

• 2096-20-0 3,5-dimethoxypyridazine 
• 627525-71-7 5-methoxy-pyridazine-3-carboxylic acid ethyl ester 
• 1071535-20-0 5-methoxy-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)pyridazin-3-amine 
• 943997-55-5 3-(4-tert-butylphenyl)-5-methoxypyridazine 
• 20733-11-3 4-methoxypyridazine 

Relevant articles and documents

ErbB RECEPTOR INHIBITORS AS ANTI-TUMOR AGENTS

Provided herein are novel compounds as inhibitors of type I receptor tyrosine kinases, the pharmaceutical compositions comprising one or more of the compounds and salts thereof as an active ingredient, and the use of the compounds and salts thereof in the treatment of hyperproliferative diseases, such as cancer and inflammation, in mammals and especially in humans.

INHIBITORS OF SARM1

The present disclosure provides compounds and methods useful for inhibiting SARM1 and/or treating and/or preventing axonal degeneration.

HETEROARYLBENZIMIDAZOLE COMPOUNDS

The present invention covers heteroarylbenzimidazole compounds of general formula (I) in which R1, R2, R3, R4 and R5 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative and/or inflammatory disorders, as a sole agent or in combination with other active ingredients.

BENZAMIDE DERIVATIVES AS P2X7 RECEPTOR ANTAGONISTS

The invention relates to benzamide derivatives of formula (I), wherein R1, R2, R3, R4, R5, R6, n and Y are as defined in the description, their preparation and their use as pharmaceutically active compounds.

BENZAMIDE DERIVATIVES AS P2X7 RECEPTOR ANTAGONISTS

The invention relates to benzamide derivatives of formula (I),wherein R1, R2, R3, R4, R5, R6, n and Y are as defined in the description, their preparation and their use as pharmaceutically active compounds.

N-phenyl-4-pyrazolo[1,5-6]pyridazin-3-ylpyrimidin-2-amines as potent and selective inhibitors of glycogen synthase kinase 3 with good cellular efficacy

Glycogen synthase kinase 3 regulates glycogen synthase, the rate-determining enzyme for glycogen synthesis. Liver and muscle glycogen synthesis is defective in type 2 diabetics, resulting in elevated plasma glucose levels. Inhibition of GSK-3 could potentially be an effective method to control plasma glucose levels in type 2 diabetics. Structure-activity studies on a N-phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine series have led to the identification of potent and selective compounds with good cellular efficacy. Molecular modeling studies have given insights into the mode of binding of these inhibitors. Since the initial leads were also potent inhibitors of CDK-2/CDK-4, an extensive SAR was performed at various positions of the pyrazolo[1,5-b] pyridazin core to afford potent GSK-3 inhibitors that were highly selective over CDK-2. In addition, these inhibitors also exhibited very good cell efficacy and functional response. A representative example was shown to have good oral exposure levels, extending their utility in an in vivo setting. These inhibitors provide a viable lead series in the discovery of new therapies for the treatment of type 2 diabetes.

Hydrazinecarboxylic acids

Disclosed are certain 3-phenylpyridazines, compositions thereof which are herbicidal and methods of using such compositions for controlling undesired plants. Intermediates useful in preparing the 3-phenylpyridazines are disclosed.

3-pyrazolyloxypyridazines, herbicidal compositions and uses thereof

Disclosed are certain 3-pyrazolyloxypyridazines, compositions thereof which are herbicidal and methods of using such composition for controlling undesired plants. Also disclosed are mixtures of such pyridazines and acetanilide herbicides, to which mixture a safener may be added, if desired. Intermediate compounds useful in preparing the pyrazolyloxypyridazines are also disclosed.

3-phenoxypyridazines, herbicidal compositions and uses thereof

Disclosed are certain 3-phenoxypyridazines, compositions thereof which are herbicidal and methods of using such compositions for controlling undesired plants. Intermediate compounds useful in preparing the phenoxypyridazines are also disclosed.

A large scale synthesis of 3-chloro-5-methoxypyridazine

A large scale synthesis of 3-chloro-5-methoxypyridazine was developed (18 moles) that relies on the protection of the pyridazinone nitrogen of 4,5-dichloro-3(2H)-pyridazinone as the tetrahydropyranyl derivative 2. The 5-chloro position of the protected pyridazinone was selectively displaced with methoxide to give 3 followed by catalytic hydrogenation of the 4-chloro group to give 4. Removal of the protecting group with acid followed by phosphorous oxychloride treatment gave the target compound 6 in good yield. This route is superior to the previously described synthesis of this compound.