120103-19-7

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-2,5-DIFLUOROPHENOL is used as a key intermediate compound for the synthesis of Phenoxypyridylpyrimidine derivatives. These derivatives are known to act as modulators of Inositol requiring enzyme 1 (IRE1) activity, which plays a crucial role in cellular stress response and has been linked to various diseases, including cancer and neurodegenerative disorders. By modulating IRE1 activity, Phenoxypyridylpyrimidine derivatives have the potential to be developed into therapeutic agents for these conditions.

InChI:InChI=1/C6H5F2NO/c7-3-2-6(10)4(8)1-5(3)9/h1-2,10H,9H2

Upstream product

• 847872-05-3 2,5-difluoro-4-phenylazophenol 
• 120103-18-6 2.5-difluoro-4-nitrophenol 
• 2105-61-5 1,2,4-trifluoro-5-nitrobenzene 
• 868736-12-3 1-(benzyloxy)-2,5-difluoro-4-nitrobenzene 

Downstream Products

• 871681-62-8 (2,5-difluoro-4-hydroxy-phenyl)-carbamic acid benzyl ester 
• 1552280-93-9 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2,5-difluorophenoxy)picolinamide 
• 834154-72-2 2,5-difluoro-4-propoxy-phenylamine 
• 871681-63-9 (2,5-difluoro-4-propoxy-phenyl)-carbamic acid benzyl ester 
• 928038-46-4 Benzyl [4-(4-aminopyrimidin-6-yloxy)-2,5-difluorophenyl]carbamate 
• 928038-47-5 Benzyl [4-(4-azidopyrimidin-6-yloxy)-2,5-difluorophenyl]carbamate 
• 928038-45-3 benzyl [4-(4-chloropyrimidin-6-yloxy)-2,5-difluorophenyl]carbamate 
• 928038-48-6 4-amino-6-(4-amino-2,5-difluorophenoxy)pyrimidine 
• 928038-49-7 N-{4-[(4-Aminopyrimidin-6-yl)oxy]-2,5-difluorophenyl}-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide 
• 1345855-05-1 N-(2,5-difluoro-4-(5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide 
• 1345854-90-1 2,5-difluoro-4-(5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yloxy)benzenamine 
• 1345854-89-8 2,5-difluoro-4-(5-iodopyrimidin-4-yloxy)benzenamine 

Relevant academic research and scientific papers

POLYAROMATIC UREA DERIVATIVES AND THEIR USE IN THE TREATMENT OF MUSCLE DISEASES

The current invention provides urea derivatives, in particular compounds having the core structure heteroaryl-NH-CO-NH-aryl-O- heteroaryl, for use in treating, ameliorating, delaying, curing and/ or preventing a disease or condition associated with muscle cells and/or satellite cells, such as Duchenne muscular dystrophy, Becker muscular dystrophy, cachexia or sarcopenia.

SUBSTITUTED PYRAZOLONE COMPOUNDS AND METHODS OF USE

The present invention provides novel substituted pyrazolone compounds, pharmaceutical acceptable salts and formulations thereof useful in modulating the protein tyrosine kinase activity, and in modulating cellular activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.

SUBSTITUTED PYRAZOLONE COMPOUNDS AND METHODS OF USE

The present invention provides novel substituted pyrazolone compounds, pharmaceutical acceptable salts and formulations thereof useful in modulating the protein tyrosine kinase activity, and in modulating cellular activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.

SUBSTITUTED QUINOLINE COMPOUNDS AND METHODS OF USE

The present invention provides novel substituted quinoline compounds, pharmaceutical acceptable salts and formulations thereof useful in modulating the protein tyrosine kinase activity, and in modulating cellular activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.

PYRIDINE OR PYRIMIDINE DERIVATIVE HAVING EXCELLENT CELL GROWTH INHIBITION EFFECT AND EXCELLENT ANTI-TUMOR EFFECT ON CELL STRAIN HAVING AMPLIFICATION OF HGFR GENE

A pyridine or pyrimidine derivative represented by the formula (I) has an excellent HGFR inhibitory activity and exhibits strong cell proliferation inhibitory effect and anti-tumor effect against cancer cell lines with amplified HGFR gene. wherein R1 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; R2 and R3 represent hydrogen; R4, R5, R6, and R7 may be the same or different and each represents hydrogen, halogen, C1-6 alkyl or the like; R8 represents hydrogen or the like; R9 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; n represents an integer of 1 or 2; X represents -CH=, nitrogen.

NOVEL PYRIDINE DERIVATIVE AND PYRIMIDINE DERIVATIVE (3)

A compound represented by the following formula, a salt thereof or a hydrate of the foregoing has an excellent hepatocyte growth factor receptor (HGFR) inhibitory activity, and exhibits anti-tumor activity, angiogenesis inhibitory activity and cancer metastasis inhibitory activity. [R1 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; R2 and R3 represent hydrogen; R4, R5, R6, and R7 may be the same or different and each represents hydrogen, halogen, C1-6 alkyl or the like; R8 represents hydrogen or the like; R9 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; n represents an integer of 1 or 2; X represents -CH=, nitrogen or the like.]

Process for preparing phenoxypyridine derivatives

A process for preparing a compound represented by the formula (I): comprising reacting a compound represented by the formula (II) or salt thereof: with a compound represented by the formula (III): in the presence of a condensation reagent, wherein R1 represents 1) optionally substituted azetidin-1-yl, 2) optionally substituted pyrrolidin-1-yl, 3) optionally substituted piperidin-1-yl, etc.; R2, R3, R4 and R5 may be the same or different and each represents hydrogen or fluorine; and R6 represents hydrogen or fluorine.

Process for the preparation of halogen containing 4-amino phenols

Production of 4-aminophenol derivatives (I) comprises converting an aniline (II) to a diazonium salt (III), reacting (III) with a phenol (IV) in the presence of a base to give a phenylazophenol (V), and reacting (V) with a reducing agent and optionally O-alkylating the product. Production of 4-aminophenol derivatives of formula (I) comprises converting an aniline of formula (II) to a diazonium salt of formula (III), reacting (III) with a phenol of formula (IV) in the presence of a base to give a phenylazophenol of formula (V), and reacting (V) with a reducing agent and optionally O-alkylating the product: [Image] m : 0-3; n : 1-4; m+n : 4 or less; R 1>H, 1-12C alkyl or 5-15C aralkyl; R 2>1-12C fluoroalkyl, 1-12C fluoroalkylthio or 1-12C fluoroalkoxy; Hal : Br, Cl or F; R 3>halo, CN, SCN, SO 3M, NO 2, 1-12C alkyl, 1-12C fluoroalkyl, 1-12C fluoroalkylthio,1-12C fluoroalkoxy, 1-12C alkoxy, 1-12C alkoxycarbonyl, di(1-12C alkyl)amino, 4-14C aryl or 5-15C aralkyl; M : H or alkali metal; p : 0-3; An : an anion. Independent claims are also included for: (1) compounds (I) other than 4-amino-3,5-difluorophenol, 4-amino-2,5-difluorophenol, 4-amino-2,6-difluorophenol, 4-amino-2-chloro-6-fluorophenol, 4-amino-2-chloro-3-fluorophenol, 4-amino-2-chloro-5-fluorophenol, 4-amino-2-bromo-5-fluorophenol, 4-amino-2-fluorophenol, 4-amino-3-fluorophenol, 4-amino-5-chloro-2-(trifluoromethyl)phenol, 4-amino-2-chloro-6-(trifluoromethyl)phenol and (it is stated) 4-amino-2-(trifluoromethyl)phenol and 4-amino-3-(trifluoromethyl)phenol; compounds (V) other than 3,5-difluoro-4-phenylazo-phenol, 3-fluoro-4-phenylazophenol, 3-fluoro-4-(4'-nitrophenylazo)-phenol, 3-fluoro-4-(3'-nitrophenylazo)-phenol, 3-fluoro-4-(4'-thiocyanatophenylazo)-phenol, 3-fluoro-4-(4'-sulfophenylazo)-phenol, 4-(2'-fluoro-4'-hydroxyphenylazo)benzoic acid ethyl ester, 2-fluoro-4-(4'-fluorophenylazo)-phenol, 2-fluoro-4-(3'-fluorophenylazo)-phenol, 2-fluoro-4-(4'-sulfophenylazo)-phenol, 4-(3'-fluoro-4'-hydroxyphenylazo)benzoic acid ethyl ester, 2,3-difluoro-4-(4'-iodphenylazo)-phenol; 2,3-difluoro-4-(4'sulfophenylazo)-phenol, 2,6-difluoro-4-(2'-bromphenylazo)-phenol and (it is stated) 3-(trifluoromethyl)-4-(phenylazo)-phenol and 3-(trifluoromethyl)-4-(4'-sodiumsulfonatophenylazo)-phenol.