401564-34-9

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 4-hydroxy-2-(3-thiazolidinylcarbonyl)-, 1,1-dimethylethyl ester, (2S,4S)-
• CAS NO: 401564-34-9
• Molecular Formula: C13H22N2O4S
• Molecular Weight: 302.395
• Mol File: 401564-34-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 4-hydroxy-2-(3-thiazolidinylcarbonyl)-, 1,1-dimethylethyl ester, (2S,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 4-hydroxy-2-(3-thiazolidinylcarbonyl)-, 1,1-dimethylethyl ester, (2S,4S)-(401564-34-9)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 4-hydroxy-2-(3-thiazolidinylcarbonyl)-, 1,1-dimethylethyl ester, (2S,4S)-(401564-34-9)

Safety Data

• Hazardous Substances Data: 401564-34-9(Hazardous Substances Data)

Usage

Usage

Oral medication
Sitagliptin is taken by mouth for the treatment of type 2 diabetes.

Medical Application

Treatment of type 2 diabetes
It helps to regulate blood sugar levels in patients with type 2 diabetes.

Mechanism of Action

Dipeptidyl peptidase-4 (DPP-4) inhibitor
Sitagliptin works by inhibiting the DPP-4 enzyme, which plays a role in blood sugar regulation.

Effect on Insulin Production

Increases insulin production
By inhibiting DPP-4, Sitagliptin increases the amount of insulin produced by the body after meals.

Incretin Hormones

Increases levels of active incretin hormones
Inhibition of DPP-4 leads to higher levels of active incretin hormones, which contribute to better glycemic control.

Improved Glycemic Control

Better management of blood sugar levels
Sitagliptin ultimately helps patients with type 2 diabetes maintain better control over their blood sugar levels.

Upstream product

• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 401564-17-8 (2S,4S)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid 
• 401564-35-0 3-[(2S,4S)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-pyrrolidinylcarbonyl]-1,3-thiazolidine 

Downstream Products

• 401565-08-0 3-[(2S,4S)-4-(4-cyanobenzoyloxy)-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl]-1,3-thiazolidine 
• 1404559-22-3 3-{(2S,4R)-1-(tert-butoxycarbonyl)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine 
• 1404559-15-4 C₂₂H₃₀N₆OS 
• 401565-07-9 3-((2S,4S)-4-benzoyloxy-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl)-1,3-thiazolidine 

Relevant articles and documents

Discovery and preclinical profile of teneligliptin (3-[(2S,4S)-4-[4-(3- methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl] thiazolidine): A highly potent, selective, long-lasting and orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

Dipeptidyl peptidase IV (DPP-4) inhibition is suitable mechanism for once daily oral dosing regimen because of its low risk of hypoglycemia. We explored linked bicyclic heteroarylpiperazines substituted at the γ-position of the proline structure in the course of the investigation of l-prolylthiazolidines. The efforts led to the discovery of a highly potent, selective, long-lasting and orally active DPP-4 inhibitor, 3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5- yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine (8g), which has a unique structure characterized by five consecutive rings. An X-ray co-crystal structure of 8g in DPP-4 demonstrated that the key interaction between the phenyl ring on the pyrazole and the S2 extensive subsite of DPP-4 not only boosted potency, but also increased selectivity. Compound 8g, at 0.03 mg/kg or higher doses, significantly inhibited the increase of plasma glucose levels after an oral glucose load in Zucker fatty rats. Compound 8g (teneligliptin) has been approved for the treatment of type 2 diabetes in Japan.

PROLINE DERIVATIVES AND USE THEREOF AS DRUGS

The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.