1609467-43-7

Basic information

• Product Name: benzyl 3-[5-amino-4-cyano-3-(4-phenoxy-phenyl)-pyrazol-1-yl]-piperidine-1-carboxylate
• Synonyms: benzyl 3-[5-amino-4-cyano-3-(4-phenoxy-phenyl)-pyrazol-1-yl]-piperidine-1-carboxylate
• CAS NO: 1609467-43-7
• Molecular Weight: 493.565
• Mol File: 1609467-43-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzyl 3-[5-amino-4-cyano-3-(4-phenoxy-phenyl)-pyrazol-1-yl]-piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 3-[5-amino-4-cyano-3-(4-phenoxy-phenyl)-pyrazol-1-yl]-piperidine-1-carboxylate(1609467-43-7)
• EPA Substance Registry System: benzyl 3-[5-amino-4-cyano-3-(4-phenoxy-phenyl)-pyrazol-1-yl]-piperidine-1-carboxylate(1609467-43-7)

Safety Data

• Hazardous Substances Data: 1609467-43-7(Hazardous Substances Data)

Upstream product

• 19300-54-0 toluene-4-sulfonic acid pent-4-enyl ester 
• 1284940-16-4 benzyl 3-(2-(tert-butoxycarbonyl)hydrazinyl)piperidine-1-carboxylate 
• 330792-69-3 2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile 
• 1609467-42-6 3-(tert-butoxycarbonyl-hydrazono)-piperidine-1-carboxylic acid benzyl ester 
• 61995-20-8 N-(benzyloxycarbonyl)-3-piperidone 
• 1282834-23-4 benzyl 3-hydrazino-piperidine-1-carboxylate 
• 330792-68-2 2-[hydroxy-(4-phenoxy-phenyl)-methylene]-malononitrile 
• 2215-77-2 4-Phenoxybenzoic acid 
• 1623-95-6 4-phenoxybenzoyl chloride 

Downstream Products

• 1609467-44-8 5-amino-3-(4-phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazole-4-carbonitrile 
• 1609467-45-9 5-amino-3-(4-phenoxyphenyl)-1-piperidin-3-yl-1H-pyrazole-4-carboxylic acid amide 
• 1609465-64-6 5-amino-1-(1-cyanopiperidin-3-yl)-3-(4-phenoxyphenyl)-1H-pyrazole carboxamide 
• 1609468-23-6 (S)-5-amino-3-(4-phenoxyphenyl)-1-piperidin-3-yl-1H-pyrazole-4-carboxylic acid amide 
• 1609467-02-8 1-[(3S)-1-acryloylpiperidin-3-yl]-5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 1558038-42-8 (R)-5-amino-3-(4-phenoxyphenyl)-1-piperidin-3-yl-1H-pyrazole-4-carboxylic acid amide 
• 1558036-85-3 1-[(3R)-1-acryloylpiperidin-3-yl]-5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 1609467-03-9 5-amino-1-{1-[(2E)-but-2-enoyl]piperidin-3-yl}-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 1609467-04-0 5-amino-1-{(3R)-1-[(2E)-4-hydroxybut-2-enoyl]piperidin-3-yl}-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 1609465-65-7 5-amino-1-[(3R)-1-cyanopiperidin-3-yl]-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 1609465-66-8 5-amino-1-[(3S)-1-cyanopiperidin-3-yl]-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 1609465-67-9 5-amino-1-[1-(cyanomethyl)piperidin-3-yl]-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide 
• 936563-87-0 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one 

Relevant articles and documents

Aminopyrazole Carboxamide Bruton's Tyrosine Kinase Inhibitors. Irreversible to Reversible Covalent Reactive Group Tuning

Potent covalent inhibitors of Bruton's tyrosine kinase (BTK) based on an aminopyrazole carboxamide scaffold have been identified. Compared to acrylamide-based covalent reactive groups leading to irreversible protein adducts, cyanamide-based reversible-covalent inhibitors provided the highest combined BTK potency and EGFR selectivity. The cyanamide covalent mechanism with BTK was confirmed through enzyme kinetic, NMR, MS, and X-ray crystallographic studies. The lead cyanamide-based inhibitors demonstrated excellent kinome selectivity and rat pharmacokinetic properties.

BRUTON'S TYROSINE KINASE INHIBITORS

Disclosed herein are compounds that form covalent bonds with Bruton's tyrosine kinase (BTK). Methods for the preparation of the compounds are disclosed. Also disclosed are pharmaceutical compositions that include the compounds. Methods of using the BTK inhibitors are disclosed, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, and inflammatory diseases or conditions. (Formula I)