229007-08-3

Upstream product

• 50-00-0 formaldehyd 
• 874888-66-1 4-[N-(tetrahydropyran-4-yl)aminomethyl]-nitrobenzene 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 18600-42-5 4-nitrobenzylamine hydrochloride 
• 392277-22-4 N-methyl-N-(tetrahydropyran-4-yl)amine hydrochloride 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 7409-30-5 p-nitrobenzylamine 

Downstream Products

• 392277-22-4 N-methyl-N-(tetrahydropyran-4-yl)amine hydrochloride 
• 540-23-8 p-toluidine hydrochloride 
• 220641-87-2 N-methyl-N-(tetrahydropyran-4-yl)amine 
• 106-49-0 p-toluidine 
• 229005-57-6 2-(4-piperidinophenyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)phenyl)-6,7-dihydro-5H-benzocyclohepten-8-carboxamide 
• 229005-16-7 N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-7-(4-trifluoromethylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide 
• 229005-18-9 7-(4-ethoxyphenyl)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)-aminomethyl]phenyl]-2,3-dihydro-1-benzoxepin-4-carboxamide 
• 229005-52-1 2-(4-methylphenyl)-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-6,7-dihydro-5H-benzo[a][7]annulene-8-carboxamide 
• 229007-09-4 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline 

Relevant academic research and scientific papers

SYNTHESIS OF QUATERNARY SALT COMPOUNDS

The present invention is directed to a process, having a reduced environmental impact, for preparing phenylamino substituted quaternary salt compounds that are CCR2 antagonists.

QUATERNARY SALT CCR2 ANTAGONISTS

Quaternary salt compounds of Formula (I) or pharmaceutically acceptable forms thereof, which are CCR2 antagonists and are useful in preventing, treating or ameliorating CCR2 mediated inflammatory syndromes, disorders or diseases in a subject in need thereof.

Quaternary salt CCR2 antagonists

Quaternary salt compounds of Formula (I) or pharmaceutically acceptable forms thereof, which are CCR2 antagonists and are useful in preventing, treating or ameliorating CCR2 mediated inflammatory syndromes, disorders or diseases in a subject in need thereof.

Process development of 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline dihydrochloride: A key intermediate for TAK-779, a small-molecule nonpeptide CCR5 antagonist

A new and efficient synthesis of 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline dihydrochloride, a key intermediate for the CCR5 antagonist TAK-779, is described. Reductive alkylation of methylamine with tetrahydro-4H-pyran-4-one followed by alkylation of N-methyl-N-(tetrahydropyran-4-yl)amine with 4-nitrobenzylbromide and reduction of N-(4-nitrobenzyl)-N-(tetrahydropyran-4-yl)amine results in a 78% isolated yield from the starting materials by a scalable method, using only commercially available reagents.

Discovery of novel, potent, and selective small-molecule CCR5 antagonists as anti-HIV-1 agents: Synthesis and biological evaluation of anilide derivatives with a quaternary ammonium moiety

The search for new small-molecule CCR5 antagonists by high-throughput screening (HTS) of the Takeda chemical library using [125I]RANTES and CHO/CCR5 cells led to the discovery of lead compounds (A, B) with a quaternary ammonium or phosphonium m