1029877-94-8 Usage
Description
SYR-472, also known as trelagliptin succinate, is a highly selective, long-acting dipeptidyl peptidase-4 (DPP-4) inhibitor developed by Takeda Pharmaceuticals. It is an orally delivered antidiabetic agent that has been approved in Japan for the treatment of type 2 diabetes mellitus (DM). Trelagliptin is structurally similar to alogliptin, another DPP-4 inhibitor, and is the first of its kind to be approved for once-weekly dosing. It exhibits a potent inhibition of DPP-4 with an IC50 of 1.3 nM and has been shown to be well-tolerated in clinical studies.
Uses
Used in Pharmaceutical Industry:
SYR-472 is used as an antidiabetic agent for the treatment of type 2 diabetes. It helps improve glycemic control in patients by inhibiting the DPP-4 enzyme, which plays a crucial role in the regulation of glucose levels in the body. The long duration of action and once-weekly dosing make it a convenient and effective option for patients with type 2 diabetes.
Additionally, SYR-472 has demonstrated similar efficacy and safety to once-daily alogliptin in phase III trials, making it a viable alternative for patients who may not respond well to other DPP-4 inhibitors or require a different dosing schedule.
Clinical Use
Trelagliptin (SYR-472), a novel dipeptidyl peptidase-4 inhibitor used for the treatment of type 2 diabetes mellitus. Trelagliptin (as the salt Trelagliptin succinate) was approved for use in Japan in March 2015. Takeda, the company that developed Trelagliptin, chose to not get approval for the drug in the USA and EU.
Synthesis
The kilogram-scale synthesis of trelagliptin succinate has
been reported in five steps from commercial starting material.102 Commercial 2-bromo-5-
fluorotoluene (162) was reacted with copper cyanide in
refluxing DMF to provide the corresponding nitrile in 60%
yield. Benzylic bromination with AIBN and 1,3-dibromo-5,5-
dimethylhydantoin (DBDMH) in DCE followed by treatment
with diethyl phosphite and DIPEA gave crude benzyl bromide
163, which was substituted directly with 6-chloro-3-methyluracil
(164) in the presence of DIPEA in NMP to provide
chloride 165 in 86% yield. Reaction with commercial (R)-3-
aminopiperidine dihydrochloride 166 in the presence of
K2CO3 and i-PrOH furnished trelagliptin as the freebase.
Conversion to the HCl salt and purification by crystallization
from dichloromethane, followed by a freebasing via 50%
NaOH, and treatment with succinic acid in THF/i-PrOH at 60
°C, and final recrystallization, generated trelagliptin succinate
XIX.
Research
Trelagliptin (Zafatek) is an orally active DPP-4 inhibitor developed by Takeda and approved in Japan for the treatment of type 2 diabetes mellitus (T2DM). Unlike other approved agents of its class, which are usually administered once daily, trelagliptin can be administered once weekly. Phase II development of trelagliptin was discontinued in the USA and EU, as Takeda considered that the costs associated with obtaining approval in these markets were prohibitive.
Check Digit Verification of cas no
The CAS Registry Mumber 1029877-94-8 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,2,9,8,7 and 7 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1029877-94:
(9*1)+(8*0)+(7*2)+(6*9)+(5*8)+(4*7)+(3*7)+(2*9)+(1*4)=188
188 % 10 = 8
So 1029877-94-8 is a valid CAS Registry Number.
