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

• 38035-10-8 N,N-dimethyl-N-tetrahydro-2H-pyran-4-ylamine 
• 229008-30-4 N-(4-chloromethylphenyl)-2-(4-methylphenyl)-6,7-dihydro-5H-benzocycloheptene-8-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 
• 121-45-9 phosphorous acid trimethyl ester 
• 229007-09-4 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline 
• 229006-86-4 3-(4-methylphenyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one 
• 229006-88-6 2-(4-methylphenyl)-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid 
• 263765-67-9 3-p-tolyl-8,9-dihydro-7H-benzocycloheptene-6-carbaldehyde 
• 263765-69-1 6-dimethoxymethyl-3-p-tolyl-6,7,8,9-tetrahydro-benzocyclohepten-5-one 
• 337460-80-7 6-diethoxymethyl-3-p-tolyl-6,7,8,9-tetrahydro-benzocyclohepten-5-one 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 5205-39-0 ethyl glutaroyl chloride 
• 108-86-1 bromobenzene 
• 619-73-8 4-nitrobenzyl chloride 

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.

Development of a new synthetic route of a non-peptide CCR5 antagonist, TAK-779, for large-scale preparation

A new large-scalable preparation of TAK-779 (1), a non-peptide CCR5 antagonist, has been developed. The route selection was focused on in the process research. The selective reduction of commercially available benzonitrile derivative (4) as the starting material with sodium bis(2-methoxyethoxy)aluminum hydride followed by the Wittig reaction, hydrogenation, and intramolecular acylation gave benzocycloheptanone (7) in good yield. The conversion of α,α-unsaturated carboxylic acid (8) led from 7 to benzyl alcohol (9) and shortened the number of steps using non-protected 4-aminobenzyl alcohol. The reductive alkylation of Me2NH and tetrahydro-4H-pyran-4-one (12) smoothly gave a tertiary amine (3). The coupling of 2 chlorinated 9, and 3 successfully led to an ammonium chloride (1). A new inexpensive preparation which did not require a chromatographic method was achieved.

Anilide derivative, production and use thereof

This invention is to provide a compound of the formula: wherein R1 is an optionally substituted 5- to 6-membered ring: C is a divalent group of the formula: wherein the ring A is an optionally substituted 5- to 6-membered aromatic ring, X is an optionally substituted C, N or O atom, and the ring B is an optionally substituted 5- to 7-membered ring; Z is a chemical bond or a divalent group; R2 is (1) an optionally substituted amino group in which a nitrogen atom may form a quaternary ammonium, etc., or a salt thereof, which is useful for antagonizing MCP-1 receptor.