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Thienopyridine compound and anti-platelet aggregative activity thereof

A compound and pyridine-based technology, applied in the field of medicine, can solve problems such as slow onset of action, large individual differences in platelet inhibition, and irreversible platelet effects

Inactive Publication Date: 2014-04-02
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with other antiplatelet drugs, it has the advantages of good curative effect, low cost, and small adverse reactions, but there are also disadvantages that cannot be ignored, such as: slow onset of action, large individual differences in platelet inhibition, irreversible effects on platelets, etc. Thrombotic thrombocytopenic purpura and hemolytic uremic syndrome

Method used

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  • Thienopyridine compound and anti-platelet aggregative activity thereof
  • Thienopyridine compound and anti-platelet aggregative activity thereof
  • Thienopyridine compound and anti-platelet aggregative activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (R)-5-[1-Benzyl-2-(4-methylpiperazinyl)]ethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine oxalic acid Salt (I 1 )

[0050] Add (0.6g, 0.0021mol) intermediate 5((R)-5-(1-benzyl chloride ethyl)-4,5,6,7-tetrahydrothieno[3, 2-c] pyridine), 5ml acetonitrile, 0.43ml triethylamine, 0.03g KI and (1.15ml, 0.0105mol) N-methylpiperazine, stirred, and refluxed for 11 hours. Spin off the solvent, add 10ml ethyl acetate and 5ml water, stir for 10 minutes, let stand, separate the organic layer, extract the aqueous layer with ethyl acetate (10ml×3), combine the organic layers, wash with water, and dry with anhydrous MgSO4 , filtered, and spin-dried to obtain 0.64 g of a crude yellow oil, which was passed through a column to obtain 0.41 g of a pure light yellow oil. Yield 57.1%. IR (KBr, cm 1 )v: 3061, 3024, 2934, 2838, 2874, 1602, 1494, 1455, 1374, 1283, 1165, 1083, 1050, 1012, 747, 698; 1 H NMR (300MHz CDCl 3 )δ: 2.26 (3H, s, -NC H 3 ), 2.28-2.98 (16H, m, -PhC H 2 NC H 2 C H...

Embodiment 2

[0053] (R)-5-[1-benzyl-2-(4-ethylpiperazinyl)]ethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Salt (I 2 )

[0054] Synthesize 0.38 g of the free base of I2 according to the synthesis method of I1. Yield 55.6%. IR (KBr, cm-1) v: 3061, 3024, 2927, 2808, 2360, 1602, 1452, 1379, 1275, 1165, 1013, 749, 698; 1 HNMR (300MHzCDCl 3 )δ: 1.05-1.09 (3H, t, -NCH 2 C H 3 ), 2.26-3.00 (18H, m, -PhC H 2 NC H 2 C H 2 -saifen-, -C H 2 N(C H 2 ) 4 NC H 2 CH 3 ), 3.17-3.19 (1H, m, -(CH 2 ) 2 C H -N-), 3.73-3.92 (2H, m, -N-CH2-saifen-), 6.73-6.75 (1H, d, J=6.0Hz, -C H =CH-S), 7.06-7.08 (1H, d, J=6.0Hz, -CH=C H -S-), 7.11-7.29 (5H, m, Ar H ); ESI-MS m / z: 370.3[M+H] + .

[0055] Get 0.2g free base and add oxalic acid to form a salt under the condition of isopropanol, get pale yellow solid (I 2 )0.29g, yield 98.3%, melting point: 168-169°C.

Embodiment 3

[0057] (R)-5-[1-benzyl-2-(4-n-propylpiperazinyl)]ethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Oxalate (I 3 )

[0058] Add (0.54g, 0.0016mol) intermediate 6((R)-5-(1-benzylpiperazine ethyl)-4,5,6,7-tetrahydrothieno[3 , 2-c] pyridine), 5ml acetonitrile, 0.03g KI, 0.33ml triethylamine and (0.29ml, 0.032mol) n-propane bromide, stirred and refluxed for 12 hours. Suction filtration, spinning the filtrate to dryness, adding 10ml of dichloromethane to dissolve, washing with saturated NaCl, washing with water, drying with anhydrous NaSO4, filtering, spin-drying to obtain 0.33g of crude product of brown oil, which was purified by column to obtain 0.25g of light yellow oil. Yield 40.6%. IR (KBr, cm -1 )v: 3060, 3021, 2929, 1739, 1601, 1456, 1384, 1275, 1261, 1073, 749, 700; 1 H NMR (300MHz CDCl 3 )δ: 0.86-0.93 (3H, t, -N(CH 2 ) 2 C H 3 ), 1.45-1.55 (2H, m, -NCH 2 C H 2 CH 3 ), 2.26-2.98 (18H, m, -PhC H 2 NC H 2 C H 2 -saifen-, -C H 2 N(C H 2 ) 4 NC H 2 CH 3 ...

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Abstract

The invention discloses a thienopyridine compound and pharmaceutically acceptable salts thereof. The structure of the thienopyridine compound and pharmaceutically acceptable salts thereof is shown in a formula I, wherein R1, R2, R3, X and m are defined as specification. The invention also discloses a synthetic method of the thienopyridine compound and activity thereof in the anti-platelet aggregative aspect, and an application thereof in thrombotic diseases.

Description

Technical field: [0001] The invention relates to the anti-platelet aggregation activity of thienopyridine compounds and the application in cardiovascular and cerebrovascular diseases, belonging to the technical field of medicine. Background technique: [0002] Cardiovascular and cerebrovascular disease is a common disease that seriously threatens the health of human beings, especially middle-aged and elderly people over 50 years old. The number of people who die from cardiovascular and cerebrovascular diseases in the world is as high as 15 million every year, ranking first among various causes of death. Cardiovascular and cerebrovascular diseases have become the number one killer with the highest cause of death in humans! Cardiovascular and cerebrovascular diseases have the characteristics of "high morbidity, high disability rate, high mortality, high recurrence rate, and many complications", that is, "four highs and one high". At present, there are more than 270 million pat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04A61K31/496A61P7/02A61P9/10
CPCC07D495/04
Inventor 陈国华肖芳芳
Owner CHINA PHARM UNIV
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