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Substituted pyridine-2-ketone compounds and preparation method thereof

A ketone compound and compound technology, which are applied in the directions of organic chemistry, drug combination, antitumor drugs, etc., can solve the problems of less derivatives of pyridine-2-one compounds, less synthesis methods, etc., and achieve high yield and low price. , good biological activity

Active Publication Date: 2013-10-23
SHANGHAI STA PHARMA R&D CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The purpose of the present invention is to provide substituted pyridin-2-one compounds and preparation methods thereof, which mainly solve the technical problems that the existing pyridin-2-one compound derivatives are less and the synthesis methods are less

Method used

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  • Substituted pyridine-2-ketone compounds and preparation method thereof
  • Substituted pyridine-2-ketone compounds and preparation method thereof
  • Substituted pyridine-2-ketone compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054]

[0055]1) Compound 9 (50 g, 0.26 mol) was dissolved in tetrahydrofuran (600 mL), sodium carbonate (32.9 g 0.31 mol) was added, and di-tert-butyl carbonate (67.6 g, 0.31 mol) was added dropwise at 0°C ). After the dropwise addition was completed, the reaction solution was stirred at 30° C. for 16 hours. 200 milliliters of water were added to the reaction solution, extracted 3 times with ethyl acetate, the organic phases were combined, dried with anhydrous sodium sulfate, and concentrated to obtain a crude product, which was washed with petroleum ether to obtain compound 10 (69.5 g, yield: 91%). ESI-MS: 291.4 [M+H] + , 1 H NMR (DMSO-d6, 400 MHz) d 7.32 (m, 1H), 6.20-6.12 (m, 2H), 4.20-3.90 (m, 3H), 3.61 (dd, J = 6.4 Hz, 15.6 Hz, 1H), 3.12-2.94 (m, 3H), 2.40-2.35 (m, 1H), 1.95-1.85 (m, 2H), 1.20 (d, J= 47.6 Hz, 9H).

[0056] 2) Compound 10 (5.0 g, 17.2 mmol) and silver sulfate (5.4 g, 17.2 mmol) were dissolved in dichloromethane (150 mL), and iodine (4.4 g, 17....

Embodiment 2

[0062]

[0063] 1) Dissolve compound 13 (67 mg, 0.2 mmol) in 2 mL of dichloromethane, add triethylamine (40 mg, 0.4 mmol), 2,4-difluorobenzylamine (34 mg, 0.24 mmol), respectively, 1-Hydroxybenzotriazole (32 mg, 0.24 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (46 mg, 0.24 mmol), reaction solution Stir at 30°C for 16 hours. The reaction solution was concentrated to obtain crude product 15, which was directly used in the next reaction.

[0064] 2) Dissolve the crude product 15 in methanol (2 mL), add 2 mL of methanolic hydrochloric acid solution (4 mol / L), stir the reaction solution at 30°C for 16 hours, and purify the reaction solution by preparative high performance liquid phase to obtain compound 2 (28.86 mg, yield: 36.5%). ESI-MS: 360.4 [M+H] + , 1 H NMR (DMSO-d6, 400 MHz) d 10.28 (t, J=6.4 Hz, 1H), 9.79 (brs, 1H), 8.32 (brs, 1H), 8.30 (d, J=7.6 Hz, 1H), 7.15-7.09 (m, 1H), 7.02 (t , J=6.4 Hz, 2H), 6.54 (d, J=7.6 Hz, 1H), 4.60 (qd, J= 6.4 ...

Embodiment 3

[0066]

[0067] 1) Compound 11 (15.0 g, 36 mmol) was dissolved in benzyl alcohol (100 mL), and triethylamine (10.9 g, 108 mmol) and tetrakistriphenylphosphine palladium (4.2 g, 3.6 mmol) were added sequentially. Then carbon monoxide gas (45 psi) was introduced, the reaction solution was stirred at 65°C for 24 hours, then cooled to room temperature, the reaction solution was concentrated and purified by column chromatography to obtain white compound 16 (12 g, yield: 78.6%). ESI-MS: 425.0 [M+H] + , 1 H NMR (CD 3 OD-d 4 ) d:8.18 (d, J = 7.6 Hz, 1H), 7.45-7.30 (m, 5H), 6.39 (d, J = 7.6 Hz, 1H), 5.31 (s, 2H), 4.40-4.10 (m, 3H), 3.85 (dd, J = 6.0, 15.6Hz, 1H), 3.30-3.00 (m, 3H), 2.48 (s, 1H), 2.07-1.98 (m, 2H), 1.35-1.10 (m, 9H).

[0068] 2) Dissolve compound 16 (12.0 g, 28.3 mmol) in ethyl acetate (10 mL), add 200 ml of hydrochloric acid / ethyl acetate solution (4 mol / L) dropwise at 0°C, after the addition is complete, the reaction The mixture was reacted at room tem...

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Abstract

The present invention relates to a pyridin-2-one compound and a preparation method thereof, in particular to a substituted pyridin-2-one compound and a preparation method thereof. The method mainly solves the technical problems that the existing pyridin-2-one compound derivatives are few and the synthesis methods are few. The technical scheme of the present invention is: a substituted pyridin-2-one compound, the general structural formula is as follows:, Formula 1; wherein R1 is hydrogen, a straight-chain alkyl group with 1 to 6 carbon atoms, and a side chain containing a substituent One of alkyl, substituted aryl, substituted benzyl or a-haloketone. R2 is one of hydrogen, a straight-chain alkyl group with 1 to 6 carbon atoms, an alkyl group containing a substituent side chain, a substituted aryl group or a substituted benzyl group.

Description

Technical field [0001] The invention involves pyridine-2-ketone compounds and its preparation methods, and specially involves replaced pyridine-2-ketone-like compounds and their preparation methods. Background technique [0002] Pyridine-2-ketone compounds have extensive biochemical and pharmacological activity, and have multiple physiological activity, such as sterilization, analgesic, anti-inflammatory, anti-malaria, anti-hypertension, strong heart, anti-tumor and treatment of Parkinson's disease, etc.Essence [0003] Patent DE19639817 reports a pyridine-2-ketone compound for local treatment of skin infection caused by fungal and bacteria. [0004] [0005] AMRINONE (amrinone) is a non -ocean yellow -category. This medicine has special positive muscle characteristics. The effect of increasing heart contraction is stronger than the ocean glycoside.double effect.Clinically, it is used for the ineffective heart failure of the oral yellow, diuretics and vascular dilatants, and th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/18A61P35/00
Inventor 夏建华石亮蓝利泓马贯军杨康辉程丽莉江志赶贺海鹰陈曙辉
Owner SHANGHAI STA PHARMA R&D CO LTD
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