486459-98-7

Basic information

• Product Name: Sitagliptin Defuoro IMpurity 4
• Synonyms: Sitagliptin Defuoro IMpurity 4;(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid;(R)-3-[((tert-Butoxy)carbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid;(R)-b-(Boc-amino)-2,5-difluorobenzenebutanoic acid;(R)-Sitagliptin Defluoro Impurity 4
• CAS NO: 486459-98-7
• Molecular Formula: C₁₅H₁₉F₂NO₄
• Molecular Weight: 315.3124664
• Mol File: 486459-98-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 442.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.243±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.35±0.10(Predicted)
• CAS DataBase Reference: Sitagliptin Defuoro IMpurity 4(CAS DataBase Reference)
• NIST Chemistry Reference: Sitagliptin Defuoro IMpurity 4(486459-98-7)
• EPA Substance Registry System: Sitagliptin Defuoro IMpurity 4(486459-98-7)

Safety Data

• Hazardous Substances Data: 486459-98-7(Hazardous Substances Data)

Usage

General Description

Sitagliptin Defuoro Impurity 4, also known as (2S)-2-{[(3R)-3-amino-1-oxo-4-(2,5-difluorophenyl)butan-2-yl]amino}-4,5-dihydro-1H-imidazole-4-carboxamide, is a chemical impurity that is often found in Sitagliptin, a medication used to treat type 2 diabetes. This impurity is a byproduct of the synthesis process and must be carefully controlled and monitored to ensure the purity and safety of the final drug product. While the specific effects of Sitagliptin Defuoro Impurity 4 are not well-documented, impurities in pharmaceuticals are generally considered undesirable and should be minimized to ensure the safety and efficacy of the medication. Therefore, its presence in Sitagliptin must be carefully managed and controlled to meet regulatory standards and ensure the quality of the medication.

Upstream product

• 837430-12-3 (R)-3-[(1,1-dimethylethoxycarbonyl)amino]-1-diazo-4-(2,5-difluorophenyl)butan-2-one 
• 837430-13-4 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid methyl ester 
• 848667-53-8 (R)-3-Amino-4-(2,5-difluoro-phenyl)-butyric acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 157033-23-3 2,5-difluorophenyl acetyl chloride 
• 767352-24-9 methyl 4-(2,5-difluorophenyl)-3-oxobutanoate 
• 767352-26-1 N-benzyloxy-4(R)-[1-methyl-(2,5-difluorobenzyl)]-2-oxoazetidine 
• 764667-66-5 5-[1-hydroxy-2-(2,5-difluorophenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 767352-25-0 N-benzyloxy-4-(2,5-difluorophenyl)-3(S)-hydroxybutanamide 
• 85068-27-5 2,5-difluorophenylacetic acid 
• 85117-99-3 2-(bromomethyl)-1,4-difluorobenzene 
• 261380-31-8 (R)-N-(1,1-dimethylethoxycarbonyl)-2,5-difluorophenylalanine 
• 837430-11-2 (R)-N-(1,1-dimethylethoxycarbonyl)-2,5-difluorophenylalanine methyl ester 
• 837430-10-1 (2R,5S)-2,5-dihydro-3,6-dimethoxy-2-[(2',5'-difluorophenyl)methyl]-5-isopropylpyrazine 

Downstream Products

• 486460-22-4 7-[(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine 
• 1026406-69-8 {1-(2,5-difluoro-benzyl)-3-oxo-3-[3-(2,2,2-trifluoro-ethyl)-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-propyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

BETA-AMINO HETEROCYCLIC DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES

The present invention is directed to compounds which are inhibitors of the dipeptidyl peptidase-IV enzyme (“DP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

(2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a] pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine: A potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

A novel series of β-amino amides incorporating fused heterocycles, i.e., triazolopiperazines, were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-IV) for the treatment of type 2 diabetes. (2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H) -yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (1) is a potent, orally active DPP-IV inhibitor (IC50 = 18 nM) with excellent selectivity over other proline-selective peptidases, oral bioavailability in preclinical species, and in vivo efficacy in animal models. MK-0431, the phosphate salt of compound 1, was selected for development as a potential new treatment for type 2 diabetes.

3-AMINO-4-PHENYLBUTANOIC ACID DERIVATIVES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES

The present invention is directed to 3-amino-4-phenylbutanoic acid derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ("DP-IV inhibitors") and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.