1638544-64-5

Basic information

• Product Name: (S)-Alogliptin Benzoate Salt
• Synonyms: (S)-Alogliptin Benzoate Salt;(S)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile benzoate
• CAS NO: 1638544-64-5
• Molecular Formula: C25H27N5O4
• Molecular Weight: 461.51298
• Mol File: 1638544-64-5.mol
• Article Data: 30

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Slightly, Sonicated), Ethanol (Slightly, Heated, Sonicated), Methano
• CAS DataBase Reference: (S)-Alogliptin Benzoate Salt(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Alogliptin Benzoate Salt(1638544-64-5)
• EPA Substance Registry System: (S)-Alogliptin Benzoate Salt(1638544-64-5)

Safety Data

• Hazardous Substances Data: 1638544-64-5(Hazardous Substances Data)

Usage

Description

(S)-Alogliptin Benzoate Salt is a derivative of Alogliptin, a selective inhibitor of the enzyme dipeptidyl peptidase-4 (DPP-4). It is an impurity found in Alogliptin, which is an oral antihyperglycemic agent used for the treatment of type 2 diabetes. The compound plays a significant role in the pharmaceutical industry due to its association with diabetes management.

Uses

Used in Pharmaceutical Industry:
(S)-Alogliptin Benzoate Salt is used as an impurity in the development and production of Alogliptin (A575425), an oral antihyperglycemic agent. It contributes to the overall effectiveness of the drug by targeting the DPP-4 enzyme, which plays a crucial role in blood sugar regulation. By inhibiting this enzyme, Alogliptin helps to increase the levels of insulin and decrease the levels of glucose in the blood, thus managing diabetes more effectively.
Additionally, as an impurity, (S)-Alogliptin Benzoate Salt may be subject to further research and development to understand its potential impact on the efficacy and safety of Alogliptin. This could lead to improvements in the drug's formulation and administration, ultimately benefiting patients with type 2 diabetes.

Upstream product

• 850649-61-5 alogliptin 
• 65-85-0 benzoic acid 
• 1246610-75-2 Alogliptin hydrochloride 
• 1246610-74-1 2-[[6-[(3R)-3-tert-butoxycarbonylamino-1-piperidinyl]-3,4-dihydro-2,4-dioxo-3-methyl-1(2H)-pyrimidinyl]methyl]benzonitrile 
• 22115-41-9 2-(bromomethyl)benzonitrile 
• 4318-56-3 3-methyl-6-chlorouracil 
• 865758-96-9 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile 
• 612-13-5 2-cyanobenzyl chloride 
• 865758-95-8 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile 
• 127294-73-9 (R)-piperidin-3-ylamine 
• 7032-11-3 1,4,5,6-tetrahydropyridine-3-carboxamide 
• 98-92-0 nicotinamide 
• 309956-78-3 (R)-piperidin-3-ylcarbamic acid tert-butyl ester 
• 344957-25-1 2-(aminomethyl)benzonitrile 

Relevant articles and documents

Synthesis process of alogliptin benzoate

The invention discloses a synthesis process of alogliptin benzoate. The synthesis process comprises the following steps: 1, preparing an initial raw material 6-chlorouracil; 2, preparing 2-((6-chlorine-2, 4-dioxo-3, 4-dihydro-2H-pyrimidine-1-radical)methyl)cyanophenyl; 3, preparing 2-[(6-chlorine-3, 4-dihydro-3-methyl-2, 4-dioxo-1(2H)-pyrimidinyl)methyl]benzonitrile; 4, preparing alogliptin; 5, preparing alogliptin benzoate. According to the invention, the alogliptin benzoate is synthesized by taking cheap and easily available 6-chlorouracil, alpha bromo-o-methylbenzonitrile and (R)-3-aminopiperidine as raw materials through reactions such as alkylation, methylation, affinity substitution, salification and the like; according to the synthetic route, raw materials are cheap and easy to obtain, the synthetic cost is reduced, all steps are classic reactions, and synthesis improvement is easy; the improved process is low in raw material cost, simple to operate, mild in reaction condition,simple in post-treatment and suitable for industrial production.

Development and Scale-Up of an Asymmetric Synthesis Process for Alogliptin

Alogliptin (1) benzoate is a potent, highly selective inhibitor of serine protease dipeptidyl-peptidase IV, approved by US FDA for the treatment of type 2 diabetes. Herein, we report a more cost-effective process that includes ruthenium-catalyzed asymmetric hydrogenation followed by Hofmann rearrangement of 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile (10) to introduce a chiral amino moiety at a late stage. Use of an inexpensive and readily available nicotinamide (6) for a chiral aminopiperidine core and iodobenzene diacetate (PIDA) under mild and specific conditions allowed us to access 1 with excellent total yield and comparable quality to that manufactured by the original process.

Simple preparation method of alogliptin benzoate

The invention relates to an alogliptin benzoate preparation method, which comprises that 3,3-dihalogenated-N-methyl acrylamide sequentially reacts with (R)-3-Boc-aminopiperidine and 2-cyano benzylamine to prepare (R)-3-(3-Bocamino)piperidine-1-yl-3-(2-cyano)benzylamino-N-methacrylamide, the obtained material reacts with a carbonylation reagent to prepare alogliptin, and the alogliptin and benzoicacid are subjected to salt forming to prepare alogliptin benzoate. According to the present invention, the method has advantages of inexpensive and easily available raw materials, simple operation andless wastewater, and is suitable for the industrial production of alogliptin benzoate.