229005-80-5

Basic information

• Product Name: Tak 799
• Synonyms: 2H-Oyran-4-aminium, N-((4-(((6,7-dihydro-2-(4-methylphenyl)-5H-benzocyclohepten-8-yl)carbonyl)amino)phenyl)methyl)tetrahydro-N,N-dimethyl-;2H-Pyran-4-aminium, N,N-dimethyl-N-(4-(((2-(4-methylphenyl)-6,7-dihydro-5H-benzocyclohepten-8-yl)carbonyl)amino)benzyl)tetrahydro-, chloride;N,N-Dimethyl-N-(4-(((2-(4-methylphenyl)-6,7-dihydro-5H-benzocyclohepten-8-yl)carbonyl)amino)benzyl)tetrahydro-2H-pyran-4-aminium chloride;Tak 799;Takeda 779;N,N-Dimethyl-N-[4-[[[2-(4-methylphenyl)-6,7-dihydro-5H-benzohepten-8-yl]carbonyl]amino]benzyl]tetrahydro-2H-pyran-4-aminium chloride;TAK-779 Chemical Structure
• CAS NO: 229005-80-5
• Molecular Formula: C33H39N2O2.Cl
• Molecular Weight: 531.136
• Mol File: 229005-80-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white to beige/
• Density: g/cm³
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble3mg/mL, clear (warmed)
• CAS DataBase Reference: Tak 799(CAS DataBase Reference)
• NIST Chemistry Reference: Tak 799(229005-80-5)
• EPA Substance Registry System: Tak 799(229005-80-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 229005-80-5(Hazardous Substances Data)

Usage

Description

Tak 799, also known as TAK-779, is a pharmaceutical compound that has been developed to inhibit the interaction between CC chemokine ligand 5 (CCL5) and C-C chemokine receptor type 5 (CCR5). It is used in various applications, particularly in the field of immunology and virology, due to its ability to block the CCR5 receptor.

Uses

Used in Immunology:
Tak 799 is used as an inhibitor of the CCL5-CCR5 interaction in natural killer (NK) cytotoxicity assays. This application helps researchers study the effects of the compound on the immune system and its potential role in modulating immune responses.
Used in Virology:
In the field of virology, Tak 799 is used as a CCR5 blocker to study its effects on the human immunodeficiency virus (HIV). By blocking the CCR5 receptor, the compound can potentially prevent HIV from entering host cells, thus limiting the virus's ability to replicate and spread. This application is particularly relevant for evaluating the opening of the Panx-1 channels on peripheral blood mononuclear cells (PBMCs) isolated from HIV-infected individuals, as it may provide insights into the development of novel antiviral therapies.

Biochem/physiol Actions

TAK-779 is a potent, dual antagonist at chemokine receptors C-C chemokine receptor type 2 (CCR2) and C-C chemokine receptor type 5 (CCR5) with IC50 = 1.4 nM at CCR5 and 2.3 nM at CCR2. Antagonists of both CCR2 and CCR5 such as TAK-779 have been investigated for treatment of viruses, rheumatoid arthritis, multiple sclerosis, and cancer. CCR5 is particularly targeted for anti-HIV therapy, since HIV entry into cells requires chemokine coreceptors CCR5 and C-X-C motif chemokine receptor 4 (CXCR4).

InChI:InChI=1/C33H38N2O2.ClH/c1-24-7-11-27(12-8-24)28-14-13-26-5-4-6-29(22-30(26)21-28)33(36)34-31-15-9-25(10-16-31)23-35(2,3)32-17-19-37-20-18-32;/h7-16,21-22,32H,4-6,17-20,23H2,1-3H3;1H

Upstream product

• 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 
• 121-45-9 phosphorous acid trimethyl ester 
• 36393-42-7 4-(4-methylphenyl)benzaldehyde 
• 50670-50-3 p-(p-tolyl)benzonitrile 
• 229008-29-1 N-(4-hydroxymethylphenyl)-2-(4-methylphenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxamide 
• 229008-40-6 5-hydroxy-3-p-tolyl-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylic acid 
• 350022-60-5 5-oxo-3-p-tolyl-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylic acid methyl ester 
• 350022-61-6 5-hydroxy-3-p-tolyl-6,7,8,9-tetrahydro-5H-benzocycloheptene-6-carboxylic acid methyl ester 
• 274673-50-6 3-p-tolyl-8,9-dihydro-7H-benzocycloheptene-6-carboxylic acid methyl ester 
• 898792-67-1 5-(4-bromo-phenyl)-5-oxo-pentanoic acid ethyl ester 
• 135605-97-9 tert-butyldimethyl-4-nitrobenzyloxysilane 
• 131230-76-7 4-[(tert-butyldimethylsilyloxy)methyl]aniline 
• 22647-95-6 5-(4-bromophenyl)pentanoic acid 
• 87779-78-0 3-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one 

Relevant articles and documents

Convenient efficient synthesis of TAK-779, a nonpeptide CCR5 antagonist: Development of preparation of various ammonium salts using trialkylphosphite and N-halogenosuccinimide

A convenient and efficient synthesis of TAK-779 (1a), a nonpeptide CCR5 antagonist, has been achieved. The new methylation of tertiary amine (2) using trimethyl phosphite and N-chlorosuccinimide, followed by the addition of HCl led to ammonium chloride (1a) in 89% isolated yield without requiring a chromatographic method. By this preparation, ammonium methanesulfonate (1e) could be obtained in 75% isolated yield.

Quaternary ammonium salts and their use

This invention is to provide a compound for antagonizing CCR5, said compound being represented by the formula: wherein R1 is an optionally substituted phenyl or an optionally substituted thienyl; Y is -CH2-, -S- or -O-; and R2, R3 and R4 are independently an optionally substituted aliphatic hydrocarbon group or an optionally substituted alicyclic heterocyclic ring group, and being effective for the prevention and treatment of infectious disease of HIV.

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