| Identification | Back Directory | [Name]
Trelagliptin | [CAS]
865759-25-7 | [Synonyms]
YR-472
CS-926
Zafatek)
Trilagliptin
Trelagliplin
Trelagliptin
Glass acid trigram
Trelagliptin, >=98%
SYR472 Trelagliptin
Trelagliptin(syr472)
Trelagliptin free base
Trelagliptin impurity G
Trelagliptin Impurity 83
SYR-472; SYR472; SYR 472
Trelagliptin Isomer Impurity
TRELAGLIPTIN CAS 865759-25-7
Trelagliptin/Trelagliptin succinate
(R)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2
4-dihydropyrimidin-1(2H)-yl)methyl)-4-fluorobenzonitrile(Trelagliptin)
1-(2-broMo-5-fluorobenzyl)-6-chloro-3-MethylpriMidine-2,4(1H, 3H)-dione
2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]-4-fluorobenzonitrile
(S)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)-4-fluorobenzonitrile
(R)-2-[[6-(3-AMinopiperidin-1-yl)-3-Methyl-2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl]Methyl]-4-fluorobenzonitrile
Benzonitrile, 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H) -pyrimidinyl]methyl]-4-fluoro-
(R)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)-4-fluorobenzonitrile(Trelagliptin)
Trelagliptin (R)-2-[[6-(3-Aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]methyl]-4-fluorobenzonitrile
TrelagliptinQ: What is
Trelagliptin Q: What is the CAS Number of
Trelagliptin Q: What is the storage condition of
Trelagliptin Q: What are the applications of
Trelagliptin | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C18H20FN5O2 | [MDL Number]
MFCD22572746 | [MOL File]
865759-25-7.mol | [Molecular Weight]
357.382 |
| Questions And Answer | Back Directory | [Preparation]
Using 2-bromo-5-fluorotoluene as a raw material, non-toxic potassium ferrocyanide was used as the cyanating agent, and palladium acetate was used as the catalyst to add the cyano group. Then, N-bromosuccinimide (NBS) was used as the brominating agent, and azobisisobutyronitrile (AIBN) was used as the catalytic free radical reaction. After substitution reaction, R-3-aminopiperidine was added, and then it formed a salt with TFA. Finally, it formed a salt with succinic acid in THF via salt-to-salt conversion to form trelagliptin succinate. Starting with 2-bromo-5-fluorotoluene (2) and dimethylformamide (DMF) as solvent, the mixture was heated to 165°C and coupled with cuprous cyanide to form a cyano group. The free radical reaction formed 2-bromomethyl-4-fluorobenzyl nitrile (4), which then underwent a substitution reaction with 3-methyl-6-chlorouracil to generate 2-(6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)-4-fluorobenzyl nitrile (5). This 5-fluorobenzyl nitrile then reacted with R-3-aminopiperidine dihydrochloride and trifluoroacetic acid (TFA) in ethanol to form the trifluoroacetate salt of the target product, trelagliptin. |
| Chemical Properties | Back Directory | [Boiling point ]
519.0±60.0 °C(Predicted) | [density ]
1.38±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
≥11.6 mg/mL in DMSO; ≥3.68 mg/mL in EtOH with gentle warming and ultrasonic; ≥93.8 mg/mL in H2O | [form ]
solid | [pka]
9.88±0.20(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C18H20FN5O2/c1-22-17(25)8-16(23-6-2-3-15(21)11-23)24(18(22)26)10-13-7-14(19)5-4-12(13)9-20/h4-5,7-8,15H,2-3,6,10-11,21H2,1H3/t15-/m1/s1 | [InChIKey]
IWYJYHUNXVAVAA-OAHLLOKOSA-N | [SMILES]
C(#N)C1=CC=C(F)C=C1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 |
| Hazard Information | Back Directory | [Uses]
Trelagliptin is a highly selective, long-acting dipeptidyl peptidase IV (DPP-4) inhibitor. This inhibitor provides sustained reduction of plasma DPP-4 activity and lowering of blood glucose in animal models of diabetes. | [Definition]
ChEBI: Trelagliptin is a member of benzenes and a nitrile. | [Biological Activity]
trelagliptin (syr-472) is a selective inhibitor of dpp-4 and is developed for the treatment of type 2 diabetes mellitus (t2dm) [1].dipeptidyl peptidase (dpp)-4 also known as adenosine deaminase complexing protein 2 or cd26 is an antigenic enzyme that expressed on the surface of most cell types and plays an important role in regulating immune system, signal transduction and apoptosis [2, 3].trelagliptin (syr-472) is a potent dpp-4 inhibitor and can be administered once weekly which unlike its other class approved agents that be taken once daily [1]. in japan, | [in vivo]
Trelagliptin (oral gavage; 7 mg/kg; single dose) shows sustained PD effect in dogs and gives >80% inhibition of DPP-4 activity even after 24h[1].Trelagliptin (oral gavage; 3 mg/kg; single dose; 60 min prior to oral glucose) significantly improves the glucose tolerance capacity by decreasing the AUC0?120min of 19.3% compared with the vehicle group in ob/ob mice[3].
Trelagliptin (oral gavage; 10 mg/kg; once a week; 8 weeks) caused significant reductions in fasting blood glucose (FBG) levels, and the average reduction during the entire treatment period is 16.8% compared to the control.It also increases insulin level and raised it by 1.7-fold
in AUC0?120min in ob/ob mice[3]. | Animal Model: | ICR ob/ob mice[3] | | Dosage: | 10 mg/kg | | Administration: | Oral gavage; 10 mg/kg; once a week; 8 weeks | | Result: | Exerted chronic antidiabetic effects on type 2 diabetic db/db Mice.
|
| [target]
DPP-4 | [IC 50]
DPP-4 | [References]
[1]. mckeage, k., trelagliptin: first global approval. drugs, 2015. 75(10): p. 1161-4.
[2]. inagaki, n., et al., once-weekly trelagliptin versus daily alogliptin in japanese patients with type 2 diabetes: a randomised, double-blind, phase 3, non-inferiority study. lancet diabetes endocrinol, 2015. 3(3): p. 191-7.
[3]. inagaki, n., et al., syr-472, a novel once-weekly dipeptidyl peptidase-4 (dpp-4) inhibitor, in type 2 diabetes mellitus: a phase 2, randomised, double-blind, placebo-controlled trial. lancet diabetes endocrinol, 2014. 2(2): p. 125-32. |
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