247016-69-9

Basic information

• Product Name: 6-[[2-[[2-(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethyl]amino]ethyl]amino-3-pyridinecarbononitriledihydrochloride
• Synonyms: 6-[[2-[[2-(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethyl]amino]ethyl]amino-3-pyridinecarbononitriledihydrochloride;NVP DPP 728 dihydrochloride;NVP 728
• CAS NO: 247016-69-9
• Molecular Formula: C15H18N6O.2HCl
• Molecular Weight: 387
• Mol File: 247016-69-9.mol

Chemical Properties

• Melting Point: 167 °C (approx)
• Boiling Point: 612.1±55.0 °C(Predicted)
• Appearance: /
• Density: 0.1 g/cm3
• Storage Temp.: Desiccate at RT
• Solubility: ≥17.75 mg/mL in DMSO with gentle warming; ≥81 mg/mL in EtOH; ≥82 mg/mL in H2O
• PKA: 7.47±0.20(Predicted)
• CAS DataBase Reference: 6-[[2-[[2-(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethyl]amino]ethyl]amino-3-pyridinecarbononitriledihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[[2-[[2-(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethyl]amino]ethyl]amino-3-pyridinecarbononitriledihydrochloride(247016-69-9)
• EPA Substance Registry System: 6-[[2-[[2-(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethyl]amino]ethyl]amino-3-pyridinecarbononitriledihydrochloride(247016-69-9)

Safety Data

• Hazardous Substances Data: 247016-69-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-[[2-[[2-(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethyl]amino]ethyl]amino-3-pyridinecarbononitriledihydrochloride is used as a DPP-IV inhibitor for the treatment of type 2 diabetes. Its potent antihyperglycemic activity and excellent oral bioavailability make it a promising candidate for the development of new diabetes medications.
Used in Drug Delivery Systems:
In the field of drug delivery, 6-[[2-[[2-(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethyl]amino]ethyl]amino-3-pyridinecarbononitriledihydrochloride can be utilized as a carrier molecule for the targeted delivery of therapeutic agents. Its structural properties allow for the attachment of various drug molecules, enabling controlled and efficient release at the desired site of action.
Used in Chemical Research:
6-[[2-[[2-(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethyl]amino]ethyl]amino-3-pyridinecarbononitriledihydrochloride can also be employed in chemical research as a building block for the synthesis of novel compounds with potential applications in various industries, such as agriculture, materials science, and environmental science.

Upstream product

• 207557-35-5 (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile 
• 202460-48-8 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile 
• 7531-52-4 L-prolinamide 
• 477290-51-0 6-imidazolidin-1-ylnicotinonitrile 
• 207557-33-3 (S)-1-bromoacetyl-2-pyrrolidinecarbonitrile 
• 33252-28-7 6-chloronicotinonitrile 
• 214398-99-9 (S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide 

Relevant articles and documents

Solid and solution phase syntheses of the 2-cyanopyrrolidide DPP-IV inhibitor NVP-DPP728

DPP-IV inhibitors have been suggested as potential new treatments for type-II diabetes and 2-cyanopyrrolidides have been reported as potent DPP-IV inhibitors. Alternative synthetic approaches to one such compound, NVP-DPP728, are investigated here. One strategy is based in solution phase and is amenable to scale-up. The other is based on solid phase and is appropriate for the rapid analoging of the structural series.

1-[[(3-Hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine: A potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties

Dipeptidyl peptidase IV (DPP-IV) inhibition has the potential to become a valuable therapy for type 2 diabetes. The synthesis and structure - activity relationship of a new DPP-IV inhibitor class, N-substituted-glycyl-2-cyanopyrrolidines, are described as well as the path that led from clinical development compound 1-[2-[5-cyanopyridin-2-yl)amino]ethylamino]acetyl-2-cyano-(S)pyrrolidine (NVP-DPP728, 8c) to its follow-up, 1-[[(3-hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)pyrrolidine (NVP-LAF237, 12j). The pharmacological profile of 12j in obese Zucker fa/fa rats along with pharmacokinetic profile comparison of 8c and 12j in normal cynomolgus monkeys is discussed. The results suggest that 12j is a potent, stable, selective DPP-IV inhibitor possessing excellent oral bioavailability and potent antihyperglycemic activity with potential for once-a-day administration.

1-[2-[(5-Cyanopyridin-2-yl)amino]-ethylamino]acetyl-2-(S)-pyrrolidine -carbonitrile: A potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties

Dipeptidyl peptidase IV (DPP-IV) inhibition has the potential to become a valuable therapy for type 2 diabetes We report the first use of solid-phase synthesis in the discovery of a new DPP-IV inhibitor class and a solution-phase synthesis that is practical up to the multikilogram scale. One compound NVP-DPP728 (2), is profiled as a potent, selective, and short-acting DPP-IV inhibitor that has excellent oral bioavailability and potent antihyperglycemic activity.