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Pyridine compound and preparation method and application thereof

A compound, pyridine technology, applied in organic chemistry, drug combination, pharmaceutical formulation, etc., can solve problems such as toxic side effects and affecting drug efficacy

Inactive Publication Date: 2019-06-28
JIANGSU HENGRUI MEDICINE CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The related substances (or impurity content) of the drug directly affect the curative effect of the drug and may cause toxic and side effects

Method used

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  • Pyridine compound and preparation method and application thereof
  • Pyridine compound and preparation method and application thereof
  • Pyridine compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] React N-[4-(1-cyanocyclopentyl)phenyl]-2-(4-pyridylmethyl)amino-3-pyridineformyl and methanesulfonic acid at 90°C, cool, filter, and the mother liquor Prepared by using a preparative liquid phase system, and isolated the compound mesylate of formula A

[0036] The preparation liquid phase condition is:

[0037] Preparative column model: 50mm inner diameter column, 10μm hydrophobic C18 filler

[0038] Detection wavelength: 220nm

[0039] Flow rate: 60ml / min

[0040] Mobile phase: A: Purified water (0.1% formic acid)

[0041] B: Acetonitrile

[0042] gradient table

[0043] time (min)

A(％)

B(％)

0

75

25

60

75

25

[0044] Mass spectrum: [M1+H] + = 505.38;

[0045] 1 H-NMR (400MHz, CD 3 OD)1.28(m,2H)1.98-2.03(m,5H),2.12-2.19(m,2H),2.43-2.48(m,2H),5.23-5.25(d,1H),5.55-5.56(d, 1H),6.63-6.66(q,1H),7.23-7.25(d,2H),7.30-7.32(d,2H), 7.50-7.52(d,2H),7.73-7.75(d,2H),8.02- 8.08(m,2H),8.31-8.32(d,2H),8.38-8.39(d,2H);

[004...

Embodiment 2

[0048] In a 250L reactor, put 9kg N-[4-(1-cyanocyclopentyl)phenyl]-2-(4-pyridylmethyl)amino-3-pyridinecarbonyl (compound C), 95% iso Add 135 L of propanol aqueous solution, then add 2.05 kg of methanesulfonic acid, heat to dissolve, press filter, cool down at 0-10°C to crystallize, filter, wash, and dry to obtain a white solid with a yield of 90%.

[0049] Related Substance Testing

[0050] Preparation of the test solution: take N-(4-(1-cyanocyclopentyl)phenyl)-2-((2-hydroxyl-1,2-bis(pyridin-4-yl)ethyl)amino ) Nicotinamide methanesulfonate 25mg, placed in a 50ml measuring bottle, dissolved in a solvent (water: acetonitrile=70:30) and diluted to the mark, shaken up;

[0051] The preparation of reference substance solution: take 25 mg of compound mesylate of formula A, place in a 50ml measuring bottle, dissolve and dilute to the scale with solvent (water: acetonitrile=70:30), get 1ml in a 100ml measuring bottle, add solvent Dilute to the mark, shake well and set aside;

[005...

Embodiment 3

[0058] The related substance detection of the tablet preparation prepared by embodiment 2 crude drug

[0059] The preparation of need testing solution: take tablet, get fine powder 45mg after grinding, add solvent (water: acetonitrile=70:30) dissolve and dilute to scale, shake up, filter for subsequent use;

[0060] The preparation of reference substance solution: take 25 mg of compound mesylate of formula A, place in a 50ml measuring bottle, dissolve and dilute to the scale with solvent (water: acetonitrile=70:30), get 1ml in a 100ml measuring bottle, add solvent Dilute to the mark, shake well and set aside;

[0061] Chromatographic conditions: octadecylsilane bonded silica gel as filler, 0.01mol / L potassium dihydrogen phosphate solution as mobile phase A, acetonitrile as mobile phase B, gradient elution, detection wavelength is 260nm, gradient elution procedure is as follows :

[0062]

[0063] Measure 10 μl each of the test solution and the reference solution, inject t...

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Abstract

The invention provides a pyridine compound and a preparation method and an application thereof, in particular N-(4-(1-cyano cyclopentyl) phenyl)-2-((2-hydroxyl-1,2-di(pyridine-4-yl)ethyl)amino) nicotinamide (a compound as shown in a formula A) or officinal salt and the preparation and application thereof.

Description

technical field [0001] The present invention provides N-(4-(1-cyanocyclopentyl)phenyl)-2-((2-hydroxyl-1,2-bis(pyridin-4-yl)ethyl)amino)nicotinamide ( Formula A compound) or its pharmaceutically acceptable salt and its preparation method and use. Background technique [0002] Small molecule inhibitors of VEGFR have gradually become a new type of non-cytotoxic antitumor drugs with great application prospects. Compared with traditional cytotoxic drugs that inhibit tumor growth, therapeutic drugs targeting neovascularization have higher specificity, lower toxicity, and help overcome tumor drug resistance, and can be used for the treatment of various tumors . [0003] CN1281590C discloses that N-[4-(1-cyanocyclopentyl)phenyl]-2-(4-pyridylmethyl)amino-3-pyridinecarboxamide (compound C) is a small molecule inhibitor of VEGFR of a new generation , Meanwhile, CN101676267B reported the mesylate of N-[4-(1-cyanocyclopentyl)phenyl]-2-(4-pyridylmethyl)amino-3-pyridinecarboxamide, the ...

Claims

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Application Information

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IPC IPC(8): C07D213/82G01N30/02A61K31/444A61P35/00
Inventor 蒋辉朱汉帅
Owner JIANGSU HENGRUI MEDICINE CO LTD
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