33400-49-6

Basic information

• Product Name: 2-AMINO-3-NITRO-6-(4‘-FLUORBENZYLAMINO)-PYRIDINE SPECIALITY CHEMICALS
• Synonyms: 2-AMINO-3-NITRO-6-(4‘-FLUORBENZYLAMINO)-PYRIDINE;6-n-[(4-fluorophenyl)Methyl]-3-nitropyridine-2,6-diaMine;2,6-PyridinediaMine,N6-[(4-fluorophenyl)Methyl]-3-nitro-;-5-nitropyridine-2,6-diamine;N2-(4-Fluorobenzyl);2-AMINO-3-NITRO-6-(4‘-FLUORBENZYLAMINO)-PYRIDINE SPECIALITY CHEMICALS;N6-[(4-fluorophenyl)methyl]-3-nitropyridine-2,6-diamine;2-Amino-6-[(4-fluorobenzyl)-amino]-3-nitropyridine
• CAS NO: 33400-49-6
• Molecular Formula: C₁₂H₁₁FN₄O₂
• Molecular Weight: 262.2397432
• EINECS: 251-498-3
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 33400-49-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 464.5 °C at 760 mmHg
• Flash Point: 234.7 °C
• Appearance: Yellow solid
• Density: 1.448 g/cm³
• Vapor Pressure: 8.35E-09mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 1.52±0.50(Predicted)
• CAS DataBase Reference: 2-AMINO-3-NITRO-6-(4‘-FLUORBENZYLAMINO)-PYRIDINE SPECIALITY CHEMICALS(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-3-NITRO-6-(4‘-FLUORBENZYLAMINO)-PYRIDINE SPECIALITY CHEMICALS(33400-49-6)
• EPA Substance Registry System: 2-AMINO-3-NITRO-6-(4‘-FLUORBENZYLAMINO)-PYRIDINE SPECIALITY CHEMICALS(33400-49-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 33400-49-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Intermediate in the preparation of Flupirtine metabolites.

InChI:InChI=1/C12H11FN4O2/c13-9-3-1-8(2-4-9)7-15-11-6-5-10(17(18)19)12(14)16-11/h1-6H,7H2,(H3,14,15,16)

Upstream product

• 16013-85-7 2,6-dicholoro-3-nitropyridine 
• 27048-04-0 2-amino-6-chloro-3-nitropyridine 
• 140-75-0 para-fluorobenzylamine 

Downstream Products

• 112523-78-1 N⁶-(4-fluorobenzyl)pyridine-2,3,6-triamine 
• 1482053-40-6 C₃₂H₄₁FN₄O 
• 1609102-48-8 C₁₇H₂₁FN₄O₂ 
• 1609102-49-9 C₃₇H₄₉FN₄O₃ 
• 1609102-47-7 3-nitro-6-p-fluorobenzylaminopyridin-2-ylaminoformic acid tert-butyl ester 
• 75507-68-5 flupirtine maleate 
• 33400-45-2 flupirtine hydrochloride 
• 56995-20-1 Flupirtine 

Relevant articles and documents

Flupirtine and retigabine as templates for ligand-based drug design of KV7.2/3 activators

Drug induced liver injury (DILI) and tissue discoloration led to the recent discontinuation of the therapeutic use of the closely related drugs flupirtine and retigabine, respectively. Experience gained with these drugs strongly suggests that heterotetramer, voltage-gated potassium channels 2 and 3 (KV7.2/3) are valid targets for effective treatment of pain and epilepsy. Because the adverse effects are not related to the mechanism of action, it appears promising to investigate chemical modifications of these clinically validated, drug-like leads. In the present retro-metabolic drug design study, a series of 43 compounds were synthesized and characterized with regard to KV7.2/3 opening activity and efficacy. The most active compound 22d displays excellent potency (EC50 = 4 nM) and efficacy (154%) as a KV7.2/3 opener. Limited aqueous solubility hampered toxicity testing at concentrations higher than 63 μM, but this concentration was nontoxic to two hepatocellular cell lines (HEP-G2 and TAMH) in culture. The slightly less active but more soluble compound 25b (EC50 = 11 nM, efficacy 111%) showed an improved toxicity/activity ratio compared to flupirtine by three orders of magnitude and represents an attractive lead structure for the development of safer analgesics and antiepileptics.

Method for preparing flupirtine hydrochloride

The invention discloses a method for preparing flupirtine hydrochloride. The method comprises the following steps: adopting 2,6-dichloro-3-nitropyridine as an initial material, performing ammonolysis,substituting fluorobenzylamine, purifying, hydrogenating, performing acylation reaction, filtering, precipitating crystals and decompression drying to obtain the flupirtine hydrochloride. The methodis simple in operation, capable of simultaneously performing the hydrogenation and acylation reaction, capable of avoiding the deterioration of polyamino pyridine derivatives as far as possible, capable of titrating ethyl chloroformate without opening a kettle cover, and capable of reducing the harm on the human body.

QUINOLIUM CONJUGATES OF CYCLOSPORIN

The present invention relates to conjugates of cyclosporin with quinolium mitochondrial targeting groups, and their therapeutic uses.