163733-99-1

Usage

Uses

Used in Environmental Research:
4-Amino-2,3-difluorophenol is used as a research compound in the field of environmental science, specifically for studying dehalogenation processes. Dehalogenation is an important process in the degradation of halogenated organic compounds, which are often found as environmental pollutants. Understanding the role of 4-amino-2,3-difluorophenol in dehalogenation can help in developing strategies for the remediation of contaminated sites and the management of hazardous waste.
Used in Chemical Synthesis:
4-Amino-2,3-difluorophenol can be used as a building block or intermediate in the synthesis of various organic compounds. Its unique structure, with the amino and fluorine substituents on the phenol ring, makes it a valuable precursor for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals. 4-AMINO-2,3-DIFLUORO-PHENOL's reactivity and stability can be exploited in various chemical reactions, such as nucleophilic substitution, electrophilic aromatic substitution, and cross-coupling reactions, to produce a wide range of target molecules.
Used in Material Science:
The unique properties of 4-amino-2,3-difluorophenol, such as its electronic and steric effects, make it a potential candidate for the development of new materials with specific properties. For example, it can be used in the synthesis of novel polymers, dyes, or sensors with tailored characteristics. The incorporation of 4-amino-2,3-difluorophenol into these materials can lead to improved performance, such as enhanced stability, selectivity, or sensitivity, depending on the application.
Used in Pharmaceutical Research:
Due to its structural features, 4-amino-2,3-difluorophenol can be a valuable compound in the search for new drugs and drug candidates. Its ability to form hydrogen bonds and its potential to interact with biological targets make it an interesting starting point for the design of new therapeutic agents. Researchers can use 4-AMINO-2,3-DIFLUORO-PHENOL as a template to develop new drugs with improved pharmacological properties, such as better potency, selectivity, or reduced side effects.

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

Upstream product

• 441713-58-2 2-benzyloxy-3,4-difluoro-1-nitrobenzene 
• 868735-81-3 1-(benzyloxy)-2.3-difluoro-4-nitrobenzene 
• 123173-60-4 2,3-difluoro-4-nitrophenol 
• 2105-61-5 1,2,4-trifluoro-5-nitrobenzene 
• 771-69-7 2,3,4-trifluoronitrobenzene 
• 847872-04-2 2,3-difluoro-4-(phenyldiazenyl)phenol 

Downstream Products

• 868735-84-6 4-(4-amino-2,3-difluorophenoxy)picolinamide 
• 868735-85-7 4-(6-amino-2,3-diflurophenoxy)pyridine-2-carboxamide 
• 1020173-30-1 4-(2-chloro-pyridin-4-yloxy)-2,3-difluorophenylamine 
• 1341215-98-2 tert-butyl (6-(7-(4-amino-2,3-difluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl(2-methoxyethyl)carbamate 
• 1552280-92-8 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2,3-difluorophenoxy)picolinamide 
• 928038-50-0 N-(4-{[2-(aminocarbonyl)pyridin-4-yl]oxy}-2,3-difluorophenyl)-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxyamide 
• 928038-51-1 N-{4-[(2-Aminopyridin-4-yl)oxy]-2,3-difluorophenyl}-N'-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide 
• 1610449-47-2 1-(2,3-difluoro-4-((2-((3-methoxy-5-(2-morpholinoethoxy)phenyl)amino)pyrimidin-4-yl)oxy)phenyl)-3-(3-isopropyl-1-(p-tolyl)-1H-pyrazol-5-yl)urea 
• 1437323-99-3 4-(6,7-dimethoxyquinolin-4-yloxy)-2,3-difluorophenylamine 
• 1342836-68-3 4-(2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-2,3-difluoroaniline 

Relevant academic research and scientific papers

Discovery of a Pyrimidinedione Derivative as a Potent and Orally Bioavailable Axl Inhibitor

The receptor tyrosine kinase Axl plays important roles in promoting cancer progression, metastasis, and drug resistance and has been identified as a promising target for anticancer therapeutics. We used molecular modeling-assisted structural optimization starting with the low micromolar potency compound 9 to discover compound 13c, a highly potent and orally bioavailable Axl inhibitor. Selectivity profiling showed that 13c could inhibit the well-known oncogenic kinase Met with equal potency to its inhibition of Axl superfamily kinases. Compound 13c significantly inhibited cellular Axl and Met signaling, suppressed Axl- and Met-driven cell proliferation, and restrained Gas6/Axl-mediated cancer cell migration or invasion. Furthermore, 13c exhibited significant antitumor efficacy in Axl-driven and Met-driven tumor xenograft models, causing tumor stasis or regression at well-tolerated doses. All these favorable data make 13c a promising therapeutic candidate for cancer treatment.

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.

METHODS AND COMPOSITIONS FOR THE TREATMENT OF MYELOPROLIFERATIVE DISEASES AND OTHER PROLIFERATIVE DISEASES

Compounds of the present invention find utility in the treatment of hyperproliferative diseases, mammalian cancers and especially human cancers including but not limited to malignant, melanomas, glioblastomas, ovarian cancer, pancreatic cancer, prostate cancer, lung cancers, breast cancers, kidney cancers, cervical carcinomas, metastasis of primary tumor sites secondary sites, myeloproliferative diseases, chronic myelogenous leukemia, acute lymphocytic leukemia, papillary thyroid carcinoma, non small cell lung cancer, mesothelioma, hypereosinophilic syndrome, gastrointestinal stromal tumors, colonic cancers, thyroid cancer, ocular diseases characterized by hyperproliferation leading to blindness including various retinopathies, i.e. diabetic retinopathy and age-related macular degeneration, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, human inflammation, rheumatoid spondylitis, ostero-arthritis, asthma, gouty arthritis, sepsis, septic shock, endotoxic shock, Gram-negative sepsis, toxic shock syndrome, adult respiratory distress syndrome, stroke, reperfusion injury, neural trauma, neural ischemia, psoriasis, restenosis, chronic obstructive pulmonary disease, bone resorptive diseases, graft-versus-host reaction, Crohn's disease, ulcerative colitis, inflammatory bowel disease, pyresis, and combinations thereof, a disease caused by c-ABL kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, c-KIT kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, VEGFR kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, PDGFR kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, FLT-3 kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, TIE-2 kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, TRK kinases, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, c-MET kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof, or a disease caused by a HER kinase, oncogenic forms thereof, aberrant fusion proteins thereof and polymorphs thereof.

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.

CYCLOPROPANE AMIDES AND ANALOGS EXHIBITING ANTI-CANCER AND ANTI-PROLIFERATIVE ACTIVITIES

Compounds of the present invention find utility in the treatment of mammalian cancers and especially human cancers including, but not limited to, malignant melanomas, solid tumors, glioblastomas, ovarian cancer, pancreatic cancer, prostate cancer, lung cancers, breast cancers, kidney cancers, hepatic cancers, cervical carcinomas, metastasis of primary tumor sites, myeloproliferative diseases, chronic myelogenous leukemia, leukemias, papillary thyroid carcinoma, non-small cell lung cancer, mesothelioma, hypereosinophilic syndrome, gastrointestinal stromal tumors, colonic cancers, ocular diseases characterized by hyperproliferation leading to blindness including various retinopathies, diabetic retinopathy, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, mastocytosis, mast cell leukemia, and diseases caused by PDGFR-α kinase, PDGFR-β kinase, c-KIT kinase, cFMS kinase, c-MET kinase, and oncogenic forms, aberrant fusion proteins and polymorphs of any of the foregoing kinases.

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.]

KINASE INHIBITORS USEFUL FOR THE TREATMENT OF MYLEOPROLIFERATIVE DISEASES AND OTHER PROLIFERATIVE DISEASES

The present invention is concerned with novel compounds useful in the treatment of hyperproliferative diseases and mammalian cancers, especially human cancers. The invention also pertains to methods of modulating kinase activities, pharmaceutical compositions, and methods of treating individuals, incorporating or using the compounds. The preferred compounds are active small molecules set forth in formulae Ia-Iww.

Monocyclic heterocycles as kinase inhibitors

The present invention is directed to compounds having the formula and methods for using them for the treatment of cancer.

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.