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Pyridazinone derivatives and preparation method and application thereof

A technology for pyridazinone and derivatives is applied in the field of compounds and their preparation, and achieves the effects of simple synthesis method and obvious anti-tumor effect

Active Publication Date: 2014-05-07
SICHUAN BAILI PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The pyridazinone compounds in the above-mentioned patent documents have a structural formula of , which can be used in the treatment of inflammatory diseases, diabetes, Alzheimer's disease or cancer, where R 4 Mainly aryl substitution, R 1 is mainly halogen, R 2 For all kinds of more types to replace, R 3 Substituted by H, halogen and other substituents, but the compound containing aryl group is not directly attached to the pyridazine ring

Method used

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  • Pyridazinone derivatives and preparation method and application thereof
  • Pyridazinone derivatives and preparation method and application thereof
  • Pyridazinone derivatives and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Example 1 Intermediate 5a Synthesis

[0044]

[0045] Compound ( 4a) (200mg, 0.7245mmol) was mixed with 5ml AcOH and refluxed at an external temperature of 120°C for 2h. TLC detection (PE: EA = 5: 1), the reaction of the raw materials was complete, and the reaction was stopped. Pour the reaction solution into water, adjust the pH to neutral with ammonia water, extract the reaction solution with EA, combine the organic layers, wash with saturated brine, and anhydrous Na 2 SO 4 Dried to obtain 160mg of light yellow solid, namely 5a , yield 85%. m.p241-243°C. 1 HNMR {400 MHz, DMSO-d6 (TMS), δ (ppm)}: 13.507(s, 1H), 9.164(d, 1H, J =2.0), 8.649 (d, 1H, J =2.4), 8.231 (d, 1H, J =10.0), 7.090(d, 1H, J =10.0).

Embodiment 2

[0046] Example 2 compound 7a Synthesis

[0047]

[0048] Compound ( 4a ) (100mg, 0.362mmol) was mixed with 5ml AcOH and refluxed at an external temperature of 120°C for 20h. TLC detection (PE:EA=3:1), the reaction of the raw material was complete, and the reaction was stopped. Pour the reaction solution into water, adjust the pH to neutral with ammonia water, extract the reaction solution with EA, combine the organic layers, wash with saturated brine, and anhydrous Na 2 SO 4 Dried to obtain 60mg of light yellow solid, namely 7a , yield 68.6%.

Embodiment 3

[0049] Example 3 Compound 7b Synthesis

[0050]

[0051] Compound ( 5a ) (50mg, 0.194mmol) and piperidine (2ml) were refluxed at an external temperature of 80°C for 1h, TLC detection (PE:Acetone=1:1) The reaction of the raw materials was complete. Spin to dry piperidine, dissolve the reaction solution with EA, apply the sample by dry method, and perform column chromatography (PA: Acetone = 10:1) to obtain a dark yellow solid. that is 7b . Yield: 85%. m.p:168~170℃. 1 HNMR {400 MHz, CDCl 3 (TMS), δ (ppm)}: 10.916 (s,1H); 8.656 (s,1H); 8.249(s,1H); 7.6855 (d, 1H, J =10.0); 7.062 (d, 1H, J =9.6); 3.662 (s, 4H); 1.985 (s, 4H): 1.597 (s,2H).

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PUM

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Abstract

The invention discloses pyridazinone derivatives with the following general formula (I) in the specification, or pharmaceutically acceptable salts and hydrates thereof. The invention provides a series of pyridazinone derivatives which are simple in synthetic method and obvious in antitumor effects. Meanwhile, the invention also provides a preparation method and application of the pyridazinone derivatives.

Description

technical field [0001] The present invention relates to a compound and its preparation method and use, in particular to pyridazinone derivatives and its preparation method and use. Background technique [0002] Pyridazinones exhibit a wide range of biological activities, such as antidepressants, vasodilators, cardiotonic agents, analgesic / anti-inflammatory agents, antihypertensive agents and in agriculture as acaricides, herbicides, and As an inhibitor of acetylcholinesterase, aldose reductase, monoamine oxidase, CDKs, COX-2, P38MAP kinase, etc. [0003] Some pyridazinone compounds have shown certain antitumor activity. The patent document US2007 / 0072866A1 reports a class of pyridazinone compounds whose structural formula is , as a GSK-3β inhibitor for the treatment of metabolic diseases or neurodegenerative diseases and related diseases. [0004] Patent documents WO03 / 059891 and WO2005 / 007632 disclose that pyridazinone compounds are used to treat diseases or conditions ...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D401/14C07D237/20A61K31/5377A61K31/501A61P35/00
CPCC07D237/20C07D401/04C07D401/14A61P35/00
Inventor 吴勇朱义海俐李杰余永国刘威加
Owner SICHUAN BAILI PHARM CO LTD
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