Preparation method of Cangrelor intermediate

A technology of intermediates and specific structures, applied in the field of pharmaceutical intermediate synthesis, can solve problems such as hidden dangers in production safety, high requirements for production equipment, etc., and achieve the effects of low production equipment, low cost and high purity

Inactive Publication Date: 2016-06-22
NANTONG HONGCI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Domestic and foreign research on the synthesis method of this key intermediate and its salt mainly includes: patent CN102089035A, this method needs to use

Method used

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  • Preparation method of Cangrelor intermediate
  • Preparation method of Cangrelor intermediate
  • Preparation method of Cangrelor intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] Thoroughly stir tetrahydrofuran (5ml), (II) (27g, 100mmol), methanol (100ml), carbon disulfide (100ml), and dimethyl sulfoxide (500ml) in a reaction flask, and stir the reactants at 140-150°C for 12 Hour. After the reaction was completed, the solvent was distilled off under reduced pressure, washed with ethanol, water and saturated aqueous sodium chloride solution, and dried to obtain 24 g of the product with a yield of 80%.

[0042] Spectral data:

[0043] 1 HNMR(500MHz,DMSO)δ12.15(s,1H),8.35(s,1H),6.99(s,2H),6.16(m,1H),4.75-4.40(m,sH),3.79(d,2H ), 3.65(s,1H), 3.58(s,2H);

[0044] MS(ESI):299.07

Embodiment 2

[0046]

[0047] Diethyl ether (5ml), (II) (27g, 100mmol), methanol (100ml), carbon disulfide (100ml), and dimethyl sulfoxide (500ml) were fully stirred in a reaction flask, and the reactants were stirred at 140-150°C for 12 Hour. After the reaction was completed, the solvent was distilled off under reduced pressure, washed with ethanol, water and saturated aqueous sodium chloride solution, and dried to obtain 23 g of the product with a yield of 76.7%.

[0048] Spectral data:

[0049]1 HNMR(500MHz,DMSO)δ12.15(s,1H),8.35(s,1H),6.99(s,2H),6.16(m,1H),4.75-4.40(m,sH),3.79(d,2H ), 3.65(s,1H), 3.58(s,2H);

[0050] MS(ESI):299.07

Embodiment 3

[0052]

[0053] Thoroughly stir tetrahydrofuran and diethyl ether (5ml), (II) (27g, 100mmol), methanol (100ml), carbon disulfide (100ml), and dimethyl sulfoxide (500ml) in a reaction flask. Stir for 12 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, washed with ethanol, water and saturated aqueous sodium chloride solution, and dried to obtain 23.5 g of the product with a yield of 78.3%.

[0054] Spectral data:

[0055] 1 HNMR(500MHz,DMSO)δ12.15(s,1H),8.35(s,1H),6.99(s,2H),6.16(m,1H),4.75-4.40(m,sH),3.79(d,2H ), 3.65(s,1H), 3.58(s,2H);

[0056] MS(ESI):299.07

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Abstract

The present invention relates to a formula (I): The preparation method of the shown cangrelor intermediate, the preparation method uses the structural compound shown in the formula (II) as a raw material, in the presence of a solvent and a reaction reagent, through a specific reaction, and the product after the reaction is purified to obtain the formula ( I) Cangrelor intermediate shown; wherein, the specific structure of formula (II) is: The advantages of the present invention are: the preparation method of the present invention has the advantages of simple operation, high product purity, high safety in the reaction process, suitable for industrial production, and low cost.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical intermediates, in particular to a cangrelor intermediate [0002] method of preparation. Background technique [0003] Compound of formula III shown below: Cangrelor, namely: Cangrelor, CAS number: 163706-06-7. Cangrelor is a novel intravenous antiplatelet drug that rapidly and reversibly inhibits ADP-induced platelet aggregation. Unlike thienopyridine drugs such as clopidogrel and prasugrel, cangrelor is not a thienopyridine compound. It is administered by injection and directly acts on the P2Y12 platelet receptor to exert an anti-platelet effect. [0004] [0005] Early clinical trials have shown that the activation and aggregation of platelets are inhibited within seconds after cangrelor administration, and the function of platelets is restored within 60 minutes after stopping the administration, and its plasma half-life is about 10 minutes. The drug was successfully developed b...

Claims

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Application Information

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IPC IPC(8): C07H19/167C07H1/00
CPCC07H19/167C07H1/00
Inventor 卢建军陆誉升汪小江
Owner NANTONG HONGCI PHARMA
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