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Synthesizing method of omarigliptin

A synthesis method and compound technology, applied in the field of pharmaceutical synthesis, can solve the problems of low product yield, high cost, poor quality and the like, and achieve the effects of simple and easy synthesis method, good product quality and low cost

Inactive Publication Date: 2017-10-10
SUZHOU XINEN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the prior art, the synthesis process of alogliptin is often more complicated, the cost is higher, and there are still defects of low product yield and poor quality, which cannot be suitable for industrialized large-scale production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0021] Preparation of compound (3)

[0022] Under the protection of nitrogen, add 3.7 kg (10 mol) of compound (2), 271 g (1 mol) of mercuric chloride and 216 g (1 mol) of mercuric oxide into 20L ethanol (containing 5% water). After the completion of the reaction monitored by TLC, slowly add 25L of water, rise to room temperature, stir and crystallize, filter, wash the filter cake with 10L of water, and dry to obtain the crude product of compound (1), which is recrystallized from ethanol\water to obtain the refined product of compound (1). The product is 2.61 kg (9.2 mol), and the yield is 92.0%. HPLC detection purity: 98.1%.

[0023] 1 H NMR (400 MHz, DMSO- d 6 ) δ 7.51 – 7.09 (m, 3H), 5.20 (m, 1H), 4.74(d, J = 17.6 Hz, 1H), 4.56 – 4.35 (m, 2H), 3.90 (m, 1H), 3.30 – 2.57 (m, 3H), 1.17 (t, J = 6.0 Hz, 3H).

[0024] ESI+ [M+H] + =285.

[0025] Preparation of compound (5)

[0026] Under nitrogen protection, 2.56 kg (9.0 mol) of compound (3) and 1.85 kg (9.9 mol) of c...

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Abstract

The invention provides a synthesizing method of an omarigliptin compound shown in a formula (1). The synthesizing method comprises the following steps: by using a compound shown in a formula (2) as an initial raw material, performing a series of following reaction, so as to finally obtain the compound shown in the formula (1), namely omarigliptin, wherein reaction formulae are shown in the description. Compared with the prior art with multiple synthesizing steps and complicated synthesizing technology for synthesizing the omarigliptin, the synthesizing method has the advantages that the method is simple, the implementing is easy, the cost is lower, the yield rate is higher, the product quality is higher, and the synthesizing method is suitable for large-scale industrialized production.

Description

technical field [0001] The invention relates to a synthesis method of alogliptin, which belongs to the technical field of medicine synthesis. Background technique [0002] Ologliptin (common name: Omarigliptin, trade name Marizev), chemical name ((2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-(methylsulfonyl) )pyrrolo[3,4-c]pyrazolyl-5(2H,4H,6H)-yl)tetrahydro-2H-pyran-3-amine). The molecular weight of alogliptin: 398.43; CAS registration number: 1226781-44-7; the structural formula is shown in formula 1: [0003] [0004] Formula 1 [0005] Alogliptin was developed by Merck & Co. Omarigliptin, a drug for the treatment of type 2 diabetes approved in Japan on September 30, 2015, is a type of DPP-4 inhibitor, which can be achieved by taking it only once a week. [0006] prior art literature [0007] Non-patent literature: 1: Org. Lett., 2014, vol.16, pp5422-5425; Non-patent literature 2: J. Med.Chem., 2014, vol.57, pp3205-3212 [0008] Patent documents: WO 2013 / 003249 and US20...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 佘阳
Owner SUZHOU XINEN PHARMA
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