ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA)

Base Information

• Chemical Name: ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA)
• CAS No.: 850649-61-5
• Molecular Formula: C18H21N5O2
• Molecular Weight: 339.397
• Hs Code.: 29335990
• Mol file: 850649-61-5.mol

Synonyms:2-[[6-[(3R)-3-Aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;UNII-JHC049LO86;CHEMBL376359;CID11450633;2-({6-[(3r)-3-Aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl}methyl)benzonitrile;

Chemical Property of ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA)

Chemical Property:

• Appearance/Colour: White powder
• Boiling Point: 519.238 °C at 760 mmHg
• PKA: 9.89±0.20(Predicted)
• Flash Point: 267.826 °C
• PSA: 97.05000
• Density: 1.342 g/cm³
• LogP: 1.15978
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

Alogliptin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Alogliptin is a dipeptidyl-peptidase IV (DPP-4) inhibitor that was approved in Japan in 2010 for treatment of type 2 diabetes, a disease in which insulin resistance and β-cell dysfunction lead to hyperglycemia. As islet function is lost, the severity of insulin resistance increases. The introduction of DPP-4 inhibitors has brought a novel class of insulinotropic agents for the treatment options available to type 2 diabetic patients. The therapeutic potential of glucagon-like peptide 1 (GLP-1), an incretin peptide, for the treatment of type 2 diabetes was realized in the 1990s. The insulinotropic effects of GLP-1 depend closely on glucose concentrations providing the possibility of glucose normalization without the risk of hypoglycemia. GLP-1 has other non-insulinotropic physiological actions that are advantageous. It suppresses glucagon secretion from a cells and slows gastric emptying, which contributes to satiety and to a slower passage and reabsorption of carbohydrates. GLP-1 also contributes to satiety via a central mechanism as a neurotransmitter with effects on the hypothalamus.
• Uses: Alogliptin is an oral antihyperglycemic agent that is a selective inhibitor of the enzyme dipeptidyl peptidase-4 (DPP-4). Antidiabetic agent.
• Clinical Use: Dipeptidyl peptidase 4 inhibitor: Treatment of type 2 diabetes in combination with other therapies
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA)

There total 28 articles about ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA) 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: 92.7%

3-(R)-aminopiperidine dihydrochloride (334618-23-4) + 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile (865758-96-9) → alogliptin (850649-61-5,1108732-05-3)

Guidance literature:

With potassium hydrogencarbonate; In isopropyl alcohol; acetonitrile; at 60 ℃; for 6h;

Reference yield: 92.0%

(R)-piperidin-3-ylcarbamic acid tert-butyl ester (309956-78-3,172603-05-3) + 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile (865758-96-9) → alogliptin (850649-61-5,1108732-05-3)

Guidance literature:

2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile; With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate; In N,N-dimethyl-formamide; for 0.0833333h; Schlenk technique; Inert atmosphere;

(R)-piperidin-3-ylcarbamic acid tert-butyl ester; With triethylamine; In N,N-dimethyl-formamide; at 23 ℃; for 2h; Schlenk technique; Inert atmosphere;

With trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; at 23 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03854

Reference yield: 87.2%

(R)-1-(3-(2-cyanobenzyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)piperidine-3-carboxamide → alogliptin (850649-61-5,1108732-05-3)

Guidance literature:

With pyridine; [bis(acetoxy)iodo]benzene; In water; isopropyl alcohol; at 20 ℃; for 3h;

upstream raw materials:

2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile

2-(bromomethyl)benzonitrile

3-methyl-6-chlorouracil

2-cyanobenzyl chloride

Downstream raw materials:

Alogliptin benzoate

C₁₈H₂₃N₅O₃

Refernces

• 1、 -. "Preparation method of alogliptin benzoate". . . Retrieved 2021/01/29.
• 2、 -. "Dynamic resolution method of R-configuration alogliptin, and R-configuration alogliptin preparation method". Paragraph 0047-0050; 0051-0056; 0058-0089. . Retrieved 2020/01/12.