330942-05-7

Basic information

• Product Name: Betrixaban
• Synonyms: Betrixaban;N-(5-Chloropyridin-2-yl)-2-[[4-(N,N-dimethylcarbamimidoyl)benzoyl]amino]-5-methoxybenzamide;1-C-{4-[aMino(diMethylaMino)Methyl]benzene}-2-N-(5-chloropyridin-2-yl)-4-Methoxybenzene-1,2-dicarboxaMide;N-(5-Chloro-2-pyridinyl)-2-[[4-[(diMethylaMino)iMinoMethyl]benzoyl]aMino]-5-MethoxybenzaMide;PRT 054021;N-(5-chloropyridin-2-yl)-2-(4-(N,N-diMethylcarbaMiMidoyl)benzaMido)-4-MethoxybenzaMide;Betrixaban N-(5-Chloropyridin-2-yl)-2-[[4-(N,N-dimethylcarbamimidoyl)benzoyl]amino]-5-methoxybenzamide;N-(5-Chloropyridin-2-yl)-2-[[4-(N,N-dimethylcarbamimidoyl)benzoyl]amino]-5-methoxybenzamide Betrixaban
• CAS NO: 330942-05-7
• Molecular Formula: C₂₃H₂₂ClN₅O₃
• Molecular Weight: 451.90548
• EINECS: 682-459-2
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API
• Mol File: 330942-05-7.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• Density: 1.3g/cm³
• Refractive Index: 1.628
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.00±0.70(Predicted)
• CAS DataBase Reference: Betrixaban(CAS DataBase Reference)
• NIST Chemistry Reference: Betrixaban(330942-05-7)
• EPA Substance Registry System: Betrixaban(330942-05-7)

Safety Data

• Hazardous Substances Data: 330942-05-7(Hazardous Substances Data)

Usage

Uses

Betrixaban is a novel anticoagulant, an oral direct inhibitor of factor Xa (FXa) for use in the prevention of venous thromboembolism (VTE).

Biological Activity

betrixaban is a highly potent, selective, and orally efficacious inhibitor of factor xa with ic50 value of 1.5nm [1].betrixaban shows excellent anticoagulant potency in vitro. in the rabbit deep vein thrombosis model, the concentration of betrixaban required to double the rabbit prothrombin time is below 2μm. betrixaban is selective for fxa and has poor activity for thrombin, trypsin, t-pa and apc. the patch clamp herg assay shows that betrixaban has low affinity with herg suggesting it is safer than other candidate compounds. in addition, betrixaban displays a profile of good oral bioavailability and oral exposure, long half-life in animal models. it has bioavailability of 51.6% at dose of 0.5 mg/kg iv and 2.5 mg/kg po. furthermore, the phase ii study has proved betrixaban as an oral fxa inhibitor for prevention of venous thromboembolic events [1].

references

[1] zhang p, huang w, wang l, bao l, jia zj, bauer sm, goldman ea, probst gd, song y, su t, fan j, wu y, li w, woolfrey j, sinha u, wong pw, edwards st, arfsten ae, clizbe la, kanter j, pandey a, park g, hutchaleelaha a, lambing jl, hollenbach sj, scarborough rm, zhu by. discovery of betrixaban (prt054021), n-(5-chloropyridin-2-yl)-2-(4-(n,n-dimethylcarbamimidoyl)benzamido)-5-methoxybenzamide, a highly potent, selective, and orally efficacious factor xa inhibitor. bioorg med chem lett. 2009 apr 15;19(8):2179-85.

InChI:InChI=1/C23H22ClN5O3/c1-29(2)21(25)14-4-6-15(7-5-14)22(30)27-19-10-9-17(32-3)12-18(19)23(31)28-20-11-8-16(24)13-26-20/h4-13,25H,1-3H3,(H,27,30)(H,26,28,31)

Upstream product

• 330942-01-3 N-(5-chloro(2-pyridyl)){2-[(4-cyanophenyl)carbonylamino]-5-methoxyphenyl}carboxamide 
• 88905-74-2 dimethylaminomagnesium chloride 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 1679-64-7 Monomethyl terephthalate 
• 34231-49-7 4-(N,N-Dimethylaminocarbonyl)benzoic acid 
• 21928-11-0 methyl 4-(dimethylcarbamoyl)benzoate 
• 124-40-3 dimethyl amine 
• 280773-17-3 2-amino-N-(5-chloro-pyridin-2-yl)-5-methoxy-benzamide 
• 64459-25-2 4-cyanophenyl chloroformate 
• 40465-45-0 p-cyanophenyl isocyanate 
• 37795-77-0 6-methoxy-2H-3,1-benzoxazine-2,4(1H)-dione 
• 6705-03-9 2-Amino-5-methoxybenzoic acid 

Downstream Products

• 1616693-46-9 5-(2-((6-amidohexyl)amino)-2-oxoethyoxy)-N-(5-chloropyridin-2-yl)-2-(4-(N,N-dimethylcarbamimidoyl)benzamido)benzamide 
• 1616693-61-8 C₂₂H₂₁N₅O₃ 
• 1616693-60-7 C₂₃H₂₃N₅O₃ 
• 1514962-30-1 5-(2-((6-amidohexyl)amino)-2-oxoethyoxy)-2-(4-(N,N-dimethylcarbamimidoyl)benzamido)-N-(pyridine-2-yl)benzamide 
• 1616693-59-4 C₂₂H₂₀ClN₅O₃ 
• 936539-80-9 N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylcarbamimidoyl)benzamido]-5-methoxybenzamide maleic acid salt 

Relevant articles and documents

Preparation method of beta-caraban

The preparation method comprises the following steps: in liquid dimethylamine, a compound of the structural formula II or a salt thereof and MN (CH). 3 )2 The dimethylamine solution in the structural formula I is reacted to obtain the fritilth. M represents Li or MgX; and M is Li or Na. Wherein X is selected from one of Cl, Br and I. The preparation method disclosed by the invention is high in yield and high in product purity, can substantially avoid generation of single methyl ammonia impurities and dechlorination impurities, and greatly simplifies the subsequent refining process. In addition, the preparation method is single in solvent, the use of the mixed solvent is avoided, the later-stage solvent recovery is convenient, and the three wastes can be reduced.

Improved preparation method of beta-caraban

The invention relates to the fields of organic chemistry and pharmacy, and particularly relates to an improved method for preparing betrixaban. Compared with the prior art, the method has the advantages that the defects of use of high-corrosion hydrogen chloride gas, heavy burden for 'three wastes' treatment, difficult refining and purification of products and the like can be overcome. The method is characterized in that a metal organic compound RMR' (M is selected from Mg and Zn, R is selected from Cl, Br, I, alkyl or aryl, and R' is selected from akly or aryl) is used for reacting with dimethylamine or salt thereof in an aprotic solvent; then the obtained reacting liquid reacts with the compound or salt thereof in a formula II to prepare betrixaban. The improved novel method has the advantages of use of easily available raw materials, mild reaction condition, convenience in operation, excellent product quality and low cost and is suitable for industrial large-scale production.

Bei quxi class crystal form and its preparation and use

The invention discloses crystal forms of a factor Xa inhibitor betrixaban, a preparing method thereof, pharmaceutical compositions comprising the crystal forms of the betrixaban, and uses of the crystal forms of the betrixaban in preparation of medicines used for preventing or treating mammal diseases characterized by adverse thrombus formation.