870262-90-1

Basic information

• Product Name: Letaxaban
• Synonyms: 2(1H)-PyriMidinone, 1-[1-[(2S)-3-[(6-chloro-2-naphthalenyl)sulfonyl]-2-hydroxy-1-oxopropyl]-4-piperidinyl]tetrahydro;Letaxaban (TAK-442);Letaxaban;1-[(2S)-3-[(6-Chloro-2-naphthalenyl)sulfonyl]-2-hydroxy-1-oxopropyl]-4-(tetrahydro-2-oxo-1(2H)-pyriMidinyl)piperidine;1-[1-[(2S)-3-[(6-chloro-2-naphthalenyl)sulfonyl]-2-hydroxy-1-oxopropyl]-4-piperidinyl]tetrahydro-2(1H)-pyriMidinone;1-[1-[(2S)-3-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl]piperidin-4-yl]tetrahydropyriMidin-2(1H)-one;TAK 442
• CAS NO: 870262-90-1
• Molecular Formula: C22H26ClN3O5S
• Molecular Weight: 479.98
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 870262-90-1.mol

Chemical Properties

• Melting Point: 173-174 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 824.5±65.0 °C(Predicted)
• Appearance: /
• Density: 1.415±0.06 g/cm3(Predicted)
• PKA: 12.22±0.20(Predicted)
• CAS DataBase Reference: Letaxaban(CAS DataBase Reference)
• NIST Chemistry Reference: Letaxaban(870262-90-1)
• EPA Substance Registry System: Letaxaban(870262-90-1)

Safety Data

• Hazardous Substances Data: 870262-90-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Letaxaban is used as an anticoagulant for preventing venous thromboembolism in patients undergoing orthopedic surgery. Its selective inhibition of factor Xa helps to reduce the risk of blood clot formation without causing excessive bleeding, making it a valuable treatment option in this context.

Upstream product

• 701299-82-3 (2S)-3-[(6-chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoic acid 
• 61220-36-8 4-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)piperidine 

Relevant articles and documents

Discovery of a tetrahydropyrimidin-2(1 H)-one derivative (TAK-442) as a potent, selective, and orally active factor Xa inhibitor

Coagulation enzyme factor Xa (FXa) is a particularly promising target for the development of new anticoagulant agents. We previously reported the imidazo[1,5-c]imidazol-3-one derivative 1 as a potent and orally active FXa inhibitor. However, it was found that 1 predominantly undergoes hydrolysis upon incubation with human liver microsomes, and the human specific metabolic pathway made it difficult to predict the human pharmacokinetics. To address this issue, our synthetic efforts were focused on modification of the imidazo[1,5-c] imidazol-3-one moiety of the active metabolite 3a, derived from 1, which resulted in the discovery of the tetrahydropyrimidin-2(1H)-one derivative 5k as a highly potent and selective FXa inhibitor. Compound 5k showed no detectable amide bond cleavage in human liver microsomes, exhibited a good pharmacokinetic profile in monkeys, and had a potent antithrombotic efficacy in a rabbit model without prolongation of bleeding time. Compound 5k is currently under clinical development with the code name TAK-442.

CYCLIC AMIDE DERIVATIVES, AND THEIR PRODUCTION AND USE AS ANTITHROMBOTIC AGENTS

The present invention provides a cyclic amide derivative useful as a drug for treating thrombosis, which is represented by the formula (I): wherein R1 represents an optionally substituted cyclic hydrocarbon group or an optionally substituted heterocyclic group, W represents a bond or an optionally substituted divalent chain hydrocarbon group, a represents 0, 1, or 2, X1 represents an optionally substituted lower alkylene or an optionally substituted lower alkenylene, Y1 represents -C(O)-, -S(O)- or -S(O)2-, A represents a piperazine ring which may be further substituted or a piperidine ring which may be further substituted, X2 represents a bond or an optionally substituted lower alkylene, Y2 represents -C(O)-, -S(O)-, -S(O)2- or -C(=NR7)-, X3 represents an optionally substituted C1-4 alkylene or an optionally substituted C2-4 alkenylene, Z3 represents -N(R4)-, -O- or a bond, Z1 represents -C(R2)(R2')-, -N(R2)-, etc., and Z2 represents -C(R3)(R3')-, -N(R3)-, etc., or a salt thereof.