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Trelagliptin succinate

Trelagliptin succinate
Trelagliptin succinate structure
CAS No.
1029877-94-8
Chemical Name:
Trelagliptin succinate
Synonyms
CS-924;SRY-472;SYR-472;SYR472 succinate;SYR-472 succinate;SYR 472 succinate;SYR 111472 succinate;Telagliptin Succinate;Trelagliptin succinat;Triglitastat succinate
CBNumber:
CB22645151
Molecular Formula:
C22H26FN5O6
Formula Weight:
475.48
MOL File:
1029877-94-8.mol

Trelagliptin succinate Properties

storage temp. 
-20°C
color 
Off-white solid
FDA UNII
4118932Z90

Trelagliptin succinate Chemical Properties,Uses,Production

Description

Similar to omarigliptin, trelagliptin succinate (XIX) is a highly selective, orally delivered inhibitor of DPP-4 developed by Takeda Pharmaceuticals and approved in Japan in March 2015 for the treatment of type 2 DM. Interestingly, trelagliptin is structurally similar to alogliptin, a DPP-4 inhibitor also marketed by Takeda and described in our 2010 review, differing only in the presence of a fluorine in the 5-position of the cyanobenzyl moiety. Both trelagliptin and alogliptin are potent inhibitors of DPP-4, with IC50s of 1.3 and 5.3 nM, respectively. Notably, while similar drugs are dosed once daily, trelagliptin is the first DPP-4 inhibitor approved for onceweekly dosing. Kinetic analysis has revealed that trelagliptin is a substrate-competitive, reversible, slow-binding inhibitor (t1/2 for dissociation = ca. 30 min) of DPP-4, although the dissociation time is insufficient to explain its long-acting effects. In a phase III trial, once-weekly trelagliptin (100 mg) showed similar efficacy and safety to once-daily alogliptin (25 mg) in patients with type 2 DM inadequately controlled by diet and exercise. The medicinal chemistry discovery of trelagliptin and alogliptin as well as reviews of this class of compounds have been published.

Uses

Trelagliptin succinate (SYR-472) is a selective, long acting dipeptidyl peptidase-4 (DPP-4) inhibitor. An antidiabetic agent.
Orally active DPP-4 inhibitor that produces clinically and statistically significant improvements in glycaemic control in patients with type 2 diabetes. SYR472 has a long duration of action and is well tolerated in clinical studies.

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.

Chemical 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.

Trelagliptin succinate Preparation Products And Raw materials

Raw materials

Preparation Products


Trelagliptin succinate Suppliers

Global( 311)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Jinan Ande Pharmaceutical Co.,Ltd.
+8613256107535
andepharm@163.com CHINA 205 58
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 21032 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8882 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3013 60
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 739 60
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26734 60
Anqing Chico Pharmaceutical Co., Ltd.
15380796838
chloewu@chicopharm.cn CHINA 341 58
Lianyungang happen teng technology co., LTD
15950718863
wang666xt@163.com CHINA 296 58

View Lastest Price from Trelagliptin succinate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-22 Trelagliptin Succinate
1029877-94-8
US $1.00 / KG 1KG 99% 50kg Jinan Ande Pharmaceutical Co.,Ltd.
2021-10-18 Trelagliptin succinate
1029877-94-8
US $5.00 / Kg/Bag 1KG 99% 10Tons Hebei Senko Biotechnology Co., Ltd.
2021-10-15 Trelagliptin succinate
1029877-94-8
US $0.00 / Kg/Bag 1Kg/Bag 99% 5000kg/month Hebei Mojin Biotechnology Co., Ltd

1029877-94-8(Trelagliptin succinate)Related Search:


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  • 29877-94-8
  • C18H20FN5O2C4H6O4
  • C22H26FN5O6
  • Trelagliptin
  • Inhibitors
  • antidiabetic
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