Alogliptin benzoate

Base Information

• Chemical Name: Alogliptin benzoate
• CAS No.: 850649-62-6
• Molecular Formula: C₇H₆O₂*C₁₈H₂₁N₅O₂
• Molecular Weight: 461.52
• Mol file: 850649-62-6.mol

Synonyms:Alogliptin;2-[[6-[(3R)-3-Amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]benzonitrile benzoate;6-((3R)-3-aminopiperidin-1-yl)-1-(2-cyanobenzyl)-3-methylpyrimidin-2,4(1H,3H)-dione monobenzoate;

Chemical Property of Alogliptin benzoate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 6.22E-19mmHg at 25°C
• Boiling Point: 671.2 °C at 760 mmHg
• Flash Point: 359.7 °C
• PSA: 134.35000
• LogP: 2.54458
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly, Heated), Methanol (Slightly, Heat

Purity/Quality:

99%min ^*data from raw suppliers

AlogliptinBenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Alogliptin Benzoate is a potent DPP-4 (dipeptidyl peptidase-4) inhibitor with an IC50 value of less than 10 nM, developed by Japan's Takeda Company. This compound effectively inhibits DPP-4, exhibiting a selectivity 10,000 times higher for DPP-4 than for DPP-8 and DPP-9.^{[1] By maintaining the levels of glucagon-like peptide 1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP) in the body, it promotes insulin secretion and exerts a hypoglycemic effect. Alogliptin Benzoate serves as a treatment drug for type 2 diabetes, aiding in glucose management and insulin regulation.}
• Used in Pharmaceutical Industry: Alogliptin Benzoate is primarily utilized in the pharmaceutical industry for managing type 2 diabetes.^[4] Marketed under the trade name Nesina? in Japan and Vipidia? in Europe, it is approved for clinical use by regulatory agencies such as the US Food and Drug Administration and the European Medicines Agency. Alogliptin Benzoate effectively controls blood glucose levels by inhibiting DPP-4, with clinical efficacy and safety comparable to other DPP-4 inhibitors. Its low risk of hypoglycemia and weight gain, along with its potential to improve beta cell function, positions it as an essential component in the treatment regimen for type 2 diabetes. Additionally, Alogliptin Benzoate is often combined with other antidiabetic drugs, such as Pioglitazone, to enhance glycemic control, further expanding its application in diabetes management.^[2],^[3]
• References: [1] PREDICTION OF ANTI-DIABETIC ALOGLIPTIN STABILITY BY ISOTHERMAL STUDIES; DOI 10.21577/0100-4042.20230050; [2] Probing of Interaction between Alogliptin Benzoate and Human Serum Albumin Using Multi-Spectral Methods and Molecule Docking Technique; DOI 10.4236/oalib.1107283; [3] An Effective Chromatographic Method for Simultaneous Quantification of Antidiabetic Drugs Alogliptin Benzoate and Pioglitazone HCl in Their Tablet Dosage Form: Implementation to In vitro Dissolution Studies and Uniformity of Dosage Unit; DOI 10.1093/chromsci/bmac065; [4] Alogliptin benzoate for management of type 2 diabetes; DOI 10.2147/VHRM.S68564

Technology Process of Alogliptin benzoate

There total 31 articles about Alogliptin benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.7%

alogliptin (850649-61-5,1108732-05-3) + benzoic acid (65-85-0,8013-63-6) → Alogliptin benzoate (1638544-64-5,850649-62-6)

Guidance literature:

In ethanol; at 50 - 80 ℃;

Reference yield: 91.7%

Alogliptin hydrochloride (1246610-75-2) + benzoic acid (65-85-0,8013-63-6) → Alogliptin benzoate (1638544-64-5,850649-62-6)

Guidance literature:

Alogliptin hydrochloride; With sodium carbonate; In chloroform; at 25 ℃; for 0.333333h; Large scale;

benzoic acid; In ethanol; at 0 - 50 ℃; for 5h; Solvent; Large scale;

Reference yield: 88.9%

benzyl N-[(3R)-1-{3-[(2-cyanophenyl)methyl]-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl}piperidin-3-yl]carbamate + benzoic acid (65-85-0,8013-63-6) → Alogliptin benzoate (1638544-64-5,850649-62-6)

Guidance literature:

benzyl N-[(3R)-1-{3-[(2-cyanophenyl)methyl]-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl}piperidin-3-yl]carbamate; With 5%-palladium/activated carbon; In 2-methyltetrahydrofuran; at 20 ℃; for 5h;

benzoic acid; In isopropyl alcohol; at 60 ℃; for 1h; Solvent;

upstream raw materials:

alogliptin

benzoic acid

Alogliptin hydrochloride

2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile

Refernces

• 1、 -. "Preparation method of alogliptin benzoate". Paragraph 0028; 0032; 0038; 0042. . Retrieved 2021/01/29.
• 2、 -. "Preparation method of alogliptin benzoate intermediate and preparation method of alogliptin benzoate". Paragraph 0022; 0080-0088; 0098-0101. . Retrieved 2021/08/28.