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Pyrimidine derivative having cell-protecting activity and use thereof

A technology for drugs and compounds, applied in the field of novel pyrimidine derivatives, can solve problems such as insufficient effectiveness

Inactive Publication Date: 2011-05-04
ZENYAKU KOGYO KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] As mentioned above, existing treatments are not effective enough for neurological diseases such as ischemic brain diseases, neurodegenerative diseases or psychiatric diseases, so there is an urgent need to create more effective treatments

Method used

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  • Pyrimidine derivative having cell-protecting activity and use thereof
  • Pyrimidine derivative having cell-protecting activity and use thereof
  • Pyrimidine derivative having cell-protecting activity and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0125] One mode of embodiment of the present invention is a compound represented by general formula (1a), or a pharmaceutically acceptable salt, solvate, hydrate or prodrug thereof:

[0126] [chemical formula 11]

[0127]

[0128] where R 1 , R 2 and R 3 Each independently selected from general formula (2a), or one of them is replaced by 1 or 2 R 5 Substituted amino, or phenyl (C1-C6) alkyl, the other two are independently selected from the general formula (2a),

[0129] and R 4 Represents -F, -Cl, -Br, -I, formyl, phenyl or (C1-C6) alkoxy, wherein the phenyl can be replaced by 1 or 2 R 6 replace,

[0130] [chemical formula 12]

[0131]

[0132] wherein m is 0 or 1; n is 1, 2 or 3;

[0133] R 5 Represents -H, carboxy, (C1-C6) alkyl, (C1-C6) alkoxycarbonyl, (C1-C6) alkoxycarbonylmethyl, amino (C1-C6) alkyl (the amino group may be 1 or 2 (C1-C6) alkyl, or 1 (C1-C6) alkoxycarbonyl substituted; in addition, the carbon chain may contain carboxyl), piperazinyl (C1-C6...

Embodiment approach 2

[0303] A different embodiment of the present invention is a cytoprotective agent comprising a compound represented by general formula (1b), or a pharmaceutically acceptable salt, solvate, hydrate or prodrug thereof:

[0304] [chemical formula 18]

[0305]

[0306] where R 1 , R 2 and R 3 Each independently selected from general formula (2b):

[0307] [chemical formula 19]

[0308]

[0309] wherein m is 0 or 1; n is 1, 2 or 3;

[0310] R 5 Represents -H, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl or phenyl, wherein the phenyl can be replaced by 1 or 2 R 6 further replace;

[0311] R 6 Represents -H, -F, -Cl, -Br, -I, (C1-C6) alkyl, (C1-C6) alkylamino, (C1-C6) alkoxy, (C1-C6) alkylthio , (C1-C6) acyl, pyrrolidinyl, piperidinyl, piperazinyl, (C1-C6) alkoxycarbonyl, phenyl, benzyl, phenyl (C1-C6) alkoxy, nitro, Amino or hydroxyl;

[0312] Ar means can be replaced by 1 or 2 R 6 Substituted phenyl, benzyl, pyridyl, pyrimidinyl, thienyl, pyrrolyl, quinolinyl, t...

Embodiment 1

[0486] 4,6-Dimorpholino-2-(4-phenylpiperazin-1-yl)pyrimidine (compound 1)

[0487] (1-1) 4,6-dichloro-2-(4-phenylpiperazin-1-yl)pyrimidine and 2,4-dichloro-6-(4-phenylpiperazin-1-yl)pyrimidine Synthesis

[0488] (See the following reaction formula (11))

[0489] [chemical formula 25]

[0490]

[0491] The synthesis method will be specifically described in the following order. 2,4,6-Trichloropyrimidine (20ml, 165mmol) and triethylamine (27.7ml) were dissolved in ether (200ml), and phenylpiperazine (25.2ml, 165mmol) was added under ice cooling. After stirring at room temperature for about 1 hour, water was added and extracted twice with ether. The ether layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification was performed by silica gel chromatography (hexane:ethyl acetate=19:1) to obtain 17.6 g of 4,6-dichloro-2-(4-phenylpiperazin-1-yl)pyrimidine (yield 34%). The NMR data of the obtained...

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Abstract

Disclosed is a prophylactic or therapeutic agent for nerve diseases such as ischemic brain diseases and neurodegenerative diseases or the like or a prophylactic or therapeutic agent for diseases for which an antioxidant activity is effective, which can act as a cell-protecting agent, particularly an inhibitor of cerebral cell injury or cerebral cell death. Specifically disclosed is a compound represented by formula (1), or a pharmaceutically acceptable salt, solvate, hydrate or prodrug thereof. The formula (1) is shown in the description.

Description

[technical field] [0001] The present invention relates to novel pyrimidine derivatives useful as excellent cytoprotective agents, in particular as treatments against neurological diseases such as ischemic brain diseases or neurodegenerative diseases, or against various diseases for which antioxidant action is effective / preventive agent. [Background technique] [0002] Cell death can be broadly divided into two categories: necrotic cell death due to physical causes and programmed cell death (apoptosis). However, it is considered that there is no essential difference between the two regarding the cause of their occurrence and the mechanism in various diseases (Non-Patent Documents 1-3), and both have a deep relationship with various diseases. Especially in diseases of the central nervous system, since the function of nervous tissue is difficult to recover once it is lost, regardless of the type of cell death, the inhibition of brain cell death can have an important impact on...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/50A61K31/5377A61K31/541A61P9/04A61P9/10A61P9/12A61P17/02A61P19/08A61P21/00A61P21/02A61P25/00A61P25/04A61P25/08A61P25/14A61P25/18A61P25/24A61P25/28A61P27/06A61P43/00C07D401/04C07D401/06C07D401/12C07D495/04
CPCC07D239/46C07D239/48C07D239/49C07D239/50C07D401/04C07D401/06C07D401/12C07D403/04C07D409/06C07D417/04C07D495/04A61P1/16A61P1/18A61P13/12A61P17/02A61P19/08A61P21/00A61P21/02A61P25/00A61P25/02A61P25/04A61P25/08A61P25/14A61P25/16A61P25/18A61P25/24A61P25/28A61P27/06A61P43/00A61P9/04A61P9/10A61P9/12
Inventor 永田岳史铃木敏彰吉村朗只野尚登松野俊行佐藤秀树齐藤贤一太田壮一
Owner ZENYAKU KOGYO KK
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