307308-81-2

Usage

Molecular structure

Benzene ring with two fluorine atoms attached to 2 and 6 positions, an aniline group attached to the 4 position via an ether linkage

Uses

Intermediate in synthesis of pharmaceuticals and agrochemicals, production of dyes, pigments, polymers, herbicides, pesticides

Safety concerns

Potentially harmful if ingested, can cause skin and eye irritation upon contact

Upstream product

• 113965-61-0 1-(2,6-difluorophenoxy)-4-nitrobenzene 
• 28177-48-2 2,6-difluorophenol 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 1414356-26-5 1,3-difluoro-2-(4-iodophenoxy)benzene 
• 1196396-03-8 2-[4-(2,6-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1414356-27-6 tert-butyl (2R)-2-([4-amino-3-[4-(2,6-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl)pyrrolidine-1-carboxylate 
• 1414356-28-7 3-[4-(2,6-difluorophenoxy)phenyl]-1-[(2R)-pyrrolidin-2-ylmethyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1414356-58-3 tert-butyl (3R)-3-[4-amino-3-[4-(2,6-difluorophenoxy)-phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate 
• 1414356-59-4 3-[4-(2,6-difluorophenoxy)phenyl]-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1414353-22-2 (R)-2-(2-((4-amino-3-(4-(2,6-difluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyl)-3-cyclopropylacrylonitrile 
• 1414356-29-8 3-[(2R)-2-([4-amino-3-[4-(2,6-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl)pyrrolidin-1-yl]-3-oxopropanenitrile 
• 1414353-20-0 (R)-2-(2-((4-amino-3-(4-(2,3-difluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carbonyl)-3-cyclopropylacrylonitrile 
• 1414356-40-3 3-[(2R)-2-([4-amino-3-[4-(2,3-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl)pyrrolidin-1-yl]-3-oxopropanenitrile 
• 1414356-57-2 2-[[(3R)-3-[4-amino-3-[4-(2,6-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]carbonyl]-3-cyclopropylprop-2-enenitrile 
• 1414356-60-7 3-[(3R)-3-[4-amino-3-[4-(2,6-difluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-oxopropanenitrile 

Relevant academic research and scientific papers

CRYSTALLINE FORM OF BTK KINASE INHIBITOR AND PREPARATION METHOD THEREOF

The present invention relates to a crystalline form of a BTK kinase inhibitor and the preparation method thereof. In particular, the present invention relates to a crystal form I of (R)-4-amino-1-(1-(but-2-ynoyl)pyrrolidin-3-yl)-3-(4-(2,6-difluorophenoxy)phenyl)-1H-pyrrolo[2,3-d]pyridazin-7(6H)-one (the compound of formula (I)) and the preparation method thereof. The crystal form I of the compound of formula (I) obtained by the present invention has a good crystalline stability and chemical stability, and the crystallization solvent used has a low toxicity and low residue, thus making it more suitable for use in clinical treatment.

Crystallization form of BTK inhibitor, and preparation method thereof

The invention relates to a crystallization form of a BTK inhibitor, and a preparation method thereof, and concretely relates to a type I crystal of (R)-1-(3-(4-amino-3-(4-(2,6-difluorophenoxy)phenyl)-7-hydroxy-1H-pyrrolo[2,3-d]pyridazine-1-yl)piperidine-1-yl)propyl-2-ene-1-one (compound of formula (I)), and a preparation method thereof. The type I crystal of the compound (I) obtained in the invention has the advantages of good chemical stability and crystal form stability, and a crystallization solvent used in the invention has low toxicity and low residual, so the type I crystal of the compound (I) can be well used in clinic treatment.

AMINOPYRIDAZINONE COMPOUNDS AS PROTEIN KINASE INHIBITORS

The present disclosure provides a compound of formula (I) and the use thereof for the therapeutic treatment of human cancers including B-cell lymphoma and autoimmune diseases such as rheumatoid arthritis, systemic lupus erythematosus, and multiple sclerosis.

TREATMENT OF DRY EYE

The present disclosure provides a method of treating dry eye by inhibition of Bruton's tyrosine kinase (hereinafter "BTK") inhibitors, pharmaceutical formulations comprising the same, and processes for preparing such compounds.

Tyrosine kinase inhibitors

The present disclosure provides compounds such as pyrazolpyrimidine compounds, and pharmaceutically acceptable salts thereof, that are tyrosine kinase inhibitors, in particular BLK, BMX, EGFR, HER2, HER4, ITK, TEC, BTK, and TXK and are therefore useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as cancer and inflammatory diseases such as arthritis, and the like. Also provided are pharmaceutical compositions containing such compounds and pharmaceutically acceptable salts thereof and processes for preparing such compounds and pharmaceutically acceptable salts thereof.

Purinone Derivatives as Tyrosine Kinase Inhibitors

The present disclosure provides compounds and pharmaceutically acceptable salts thereof that are tyrosine kinase inhibitors, in particular BLK, BMX, EGFR, HER2, HER4, ITK, TEC, BTK, and TXK and are therefore useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as autoimmune diseases, cancer and inflammatory diseases. Also provided are pharmaceutical compositions containing such compounds and pharmaceutically acceptable salts thereof and processes for preparing such compounds and pharmaceutically acceptable salts thereof.

REVERSIBLE COVALENT PYRROLO- OR PYRAZOLOPYRIMIDINES USEFUL FOR THE TREATMENT CANCER AND AUTOIMMUNE DISEASES

Oral pharmaceutical formulations comprising reversible covalent compounds having a Michael acceptor moiety, a process of their production, and use of these formulations for the treatment of diseases treatable by such compounds such as cancer and autoimmune diseases.

PYRAZOLOPYRIMIDINE DERIVATIVES AS TYROSINE KINASE INHIBITORS

The present disclosure provides compounds and pharmaceutically acceptable salts that are tyrosine kinase inhibitors, in particular BLK, BMX, EGFR, HER2, HER4, ITK, Jak3, TEC, Btk, and TXK and are therefore useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as cancer and inflammatory diseases such as arthritis, and the like. Also provided are pharmaceutical compositions containing such compounds and pharmaceutically acceptable salts and processes for preparing such compounds and pharmaceutically acceptable salts.

TYROSINE KINASE INHIBITORS

The present disclosure provides compounds and pharmaceutically acceptable salts thereof that are tyrosine kinase inhibitors, in particular BLK, BMX, EGFR, HER2, HER4, ITK, TEC, BTK, and TXK and are therefore useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as cancer and inflammatory diseases such as arthritis, and the like. Also provided are pharmaceutical compositions containing such compounds and pharmaceutically acceptable salts thereof and processes for preparing such compounds and pharmaceutically acceptable salts thereof.

Derivatives of quinoline as inhibitors for MEK

1. A compound of formula (I) or a pharmaceutically acceptable salt thereof. wherein: n is 0-1; X and Y are independently selected from -NH-, -O-, -S-, or -NR8- where R8 is alkyl of 1-6 carbon atoms and X may additionally comprise a CH2 group; R7 is a group (CH2)mR9 where m is 0,or an integer of from 1-3 and R9 is a substituted aryl group, an optionally substituted cycloalkyl ring of up to 10 carbon atoms, or an optionally substituted heterocyclic ring or an N-oxide of any nitrogen containing ring; R6 is a divalent cycloalkyl of 3 to 7 carbon atoms, which may be optionally further substituted with one or more alkyl of 1 to 6 carbon atom groups; or is a divalent pyridinyl, pyimidinyl, or phenyl ring; wherein the pyridinyl, pyrimidinyl, or phenyl ring may be optionally further substituted with one or more specified groups; R1, R2, R3 and R4 are each independently selected from hydrogen or various specified organic groups. Compounds are useful as pharmaceuticals for the inhibition of MEK activity.