333994-00-6

Basic information

• Product Name: TAK-220
• Synonyms: TAK-220;1-ACETYL-N-(3-(4-(4-CARBAMOYLBENZYL)PIPERIDIN-1-YL)PROPYL)-N-(3-CHLORO-4-METHYLPHENYL)PIPERIDINE-4-CARBOXAMIDE
• CAS NO: 333994-00-6
• Molecular Formula: C31H41ClN4O3
• Molecular Weight: 553.13524
• Mol File: 333994-00-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 166-167 °C(Solv: ethyl acetate (141-78-6); ethanol (64-17-5))
• Boiling Point: 757.8±60.0 °C(Predicted)
• Appearance: /
• Density: 1.208±0.06 g/cm3(Predicted)
• PKA: 16.16±0.50(Predicted)
• CAS DataBase Reference: TAK-220(CAS DataBase Reference)
• NIST Chemistry Reference: TAK-220(333994-00-6)
• EPA Substance Registry System: TAK-220(333994-00-6)

Safety Data

• Hazardous Substances Data: 333994-00-6(Hazardous Substances Data)

Usage

Description

TAK-220 is an orally bioavailable antagonist of chemokine (C-C motif) receptor 5 (CCR5). It binds to CCR5 (IC50 = 3.5 nM for the human receptor in CHO cells), but not CCR1, CCR2b, CCR3, CCR4, or CCR7. TAK-220 inhibits the binding of chemokine (C-C motif) ligand 5 (CCL5) and CCL3 to CCR5 (IC50s = 3.5 and 1.4 nM, respectively) but does not inhibit binding of CCL4. It inhibits HIV-1 envelope-mediated membrane fusion in a macrophage (M-tropic) R5, but not in a T cell (T-tropic) X4, strain of HIV-1 (IC50s = 0.42 and >1,000 nM, respectively). TAK-220 inhibits the replication of six strains of R5 HIV-1 clinical isolates (EC90 overall mean = 13 nM) and the R5 JR-FL laboratory-adapted strain (EC50 = 0.6 nM), but not of X4 HIV-1 clinical isolates or the X4 IIIB laboratory-adapted strain (EC50s = >10,000 nM for both), in human peripheral blood mononuclear cells (PBMCs).

Upstream product

• 333795-12-3 4-(piperidin-4-ylmethyl)benzamide 
• 333985-70-9 1-acetyl-piperidine-4-carboxylic acid (3-chloro-4-methyl-phenyl)-(3-chloro-propyl)-amide 
• 95-74-9 3-chloro-p-toluidine 
• 59084-16-1 1-acetylpiperidine-4-carbonyl chloride 
• 6312-80-7 N-(3-chloro-4-methylphenyl)formamide 
• 14295-52-4 4-(diethyoxyphosphorylmethyl)benzoic acid methyl ester 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 333795-10-1 tert-Butyl 4-[4-(aminocarbonyl)benzyl]-1-piperidinecarboxylate 
• 888729-78-0 N-(3-chloro-4-methylphenyl)-N-(3-chloropropyl)formamide 
• 147969-86-6 4-{[1-(tert-Butoxycarbonyl)-4-piperidinyl]methyl}benzoic acid 

Relevant articles and documents

Discovery of a piperidine-4-carboxamide CCR5 antagonist (TAK-220) with highly potent anti-HIV-1 activity

We incorporated various polar groups into previously described piperidine-4-carboxamide CCR5 antagonists to improve their metabolic stability in human hepatic microsomes. Introducing a carbamoyl group into the phenyl ring of the 4-benzylpiperidine moiety

Cyclic amine compounds as CCR5 antagonists

A compound of formula (I) (wherein R1is a hydrogen atom, a hydrocarbon group which may be substituted, a non-aromatic heterocyclic group which may be substituted, R2is a hydrocarbon group which may be substituted, a non-aromatic heterocyclic group which may be substituted, or R1and R2may combine to each other together with A to form a heterocyclic group which may be substituted; A is N or N+—R5.Y?(R5is a hydrocarbon group; Y?is a counter anion); R3is a cyclic hydrocarbon group which may be substituted or a heterocyclic group which may be substituted; n is 0 or 1; R4is a hydrogen atom, a hydrocarbon group which may be substituted, a heterocyclic group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, or an amino group which may be substituted, E is a divalent aliphatic hydrocarbon group which may be substituted by group(s) other than oxo; G1is a bond, CO or SO2; G2is CO, SO2, NHCO, CONH or OCO; J is methine or a nitrogen atom; and each of Q and R is a bond or a divalent C1-3aliphatic hydrocarbon which may be substituted; provided that J is methine when G2is OCO, that one of Q and R is not a bond when the other is a bond and that each of Q and R is not substituted by oxo group(s) when G1is a bond) or a salt thereof has a potent CCR5 antagonistic activity and can be advantageously used for the treatment or prevention of infectious disease of various HIV in human (e.g. AIDS).