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Novel pyrimidyl sulfamide compounds with anti-tumor activity and their salts

A technology for pyrimidine sulfonamides and compounds, applied in the field of new pyrimidine sulfonamide compounds and their salts, to achieve the effects of various administration routes, good crystallization, and increased water solubility

Active Publication Date: 2006-03-29
SHANGHAI XINXING MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Activity experiments show that the compound of the present invention not only solves the problems of crystallization and water solubility of the compound due to the introduction of the sulfonyl group, but also makes the compound more stable

Method used

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  • Novel pyrimidyl sulfamide compounds with anti-tumor activity and their salts
  • Novel pyrimidyl sulfamide compounds with anti-tumor activity and their salts
  • Novel pyrimidyl sulfamide compounds with anti-tumor activity and their salts

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1. Preparation of raw material compound 4-bromomethylbenzenesulfonyl chloride (VII):

[0043] 19.1g (0.1mol) of p-toluenesulfonyl chloride was dissolved in carbon tetrachloride (CCl 4 ), heating, when the reaction solution began to reflux, add bromosuccinimide (NBS, Shanghai Chemical Reagent Company) 18.69g (0.105mol) and catalytic amount free radical initiator 2,2'-bis Azaisobutyronitrile (AIBN, Shanghai Chemical Reagent Company) 2g. After the feeding was completed, the reaction reflux intensified, the liquid was red, and red gas was generated. After no gas was generated, the reaction was refluxed for another 1 hour, and the heating was stopped. Cool to room temperature and filter. After most of the solvent was evaporated from the filtrate under reduced pressure, 100ml of petroleum ether was added and stirred to precipitate a light yellow solid, which was filtered and dried in vacuo to obtain 24g of compound VII, melting point: 53-55°C.

Embodiment 2

[0044] Embodiment 2. Preparation of intermediate compound 4-bromomethyl-N-{4-methyl-3-[4-(3-pyridyl)-2-pyrimidinyl]amino}phenylbenzenesulfonamide (VIII):

[0045] Dissolve 13.5 g (0.05 mol) of the above-mentioned 4-bromomethylbenzenesulfonyl chloride (VII) in 100 ml CH 2 Cl 2 middle. 50ml CH containing 4-methyl-3-[4-(3-pyridyl)-2-pyrimidinyl]aminoaniline (VII) 6.1g (0.025mol) and triethylamine (5ml) was added dropwise under stirring 2 Cl 2solution. After the dropwise addition was completed, the mixture was heated to reflux for 12 hours. After the reaction was completed, cool to room temperature, a yellow solid precipitated out, the solvent was evaporated under reduced pressure, the residue was dissolved in methanol and mixed with silica gel, subjected to petroleum ether-ether (5:1) silica gel column chromatography, and the eluate was recrystallized from ethanol to obtain the intermediate 15 g of 4-bromomethyl-N-{4-methyl-3-[4-(3-pyridyl)-2-pyrimidinyl]amino}phenylbenzenes...

Embodiment 3

[0046] Embodiment 3. Preparation of one of the compounds of the present invention:

[0047] 4-[4-methyl-1-piperazinyl]methyl-N-{4-methyl-3-[4-(3-pyridyl)-2-pyrimidinyl]amino}phenylbenzenesulfonamide ( Compound code number 100504, L group is N-methylpiperazinyl)

[0048] After 0.51g (0.001mol) of the intermediate compound (VIII) prepared in Example 2 was dissolved in 15ml absolute absolute ethanol, it was added dropwise to 45ml absolute alcohol containing 0.4g (0.004mol, Shanghai Reagent Company) of nitrogen-methylpiperazine. In absolute ethanol solution, heat to reflux, use thin layer chromatography (TLC) to track and judge the reaction end point, and the reaction is complete in about 20 hours. The reaction solution was concentrated, the residue was dissolved in methanol and mixed with silica gel, the crude product was obtained by column chromatography of petroleum ether-ethyl acetate (5:1), and 0.45 g of the product was obtained by ethanol recrystallization, melting point: 1...

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Abstract

The present invention relates to one new kind of pyrimidyl sulfamide compound with antitumor activity and its pharmaceutically acceptable salts. The present invention introduces sulfonyl group to available antitumor compound pyrimidylamine compound, which has poor crystallization performance, poor water solubility and lower bioavailability, to prepare pyrimidyl sulfamide compound. Active experiment shows that the compound of the present invention has good crystallization performance, high water solubility and raised antitumor activity and may be used in preparing antitumor medicine.

Description

technical field [0001] The invention relates to a class of novel pyrimidine sulfonamide compounds and their salts with antitumor activity. Background technique [0002] Cancer is currently one of the most important diseases that endanger human health and normal life. The research and development of anticancer drugs has always been a hot topic chosen by scientists. Due to the complexity and particularity of the mechanism of cancer, it is not easy to find anticancer drugs with high selectivity, high efficiency and low side effects. [0003] In the malignant growth and metastasis of solid tumors, new blood vessels in tumor tissue play an important role, which provides essential nutrients and oxygen for tumor growth. Angiogenesis inhibitors can inhibit the activity of vascular endothelial growth factor receptor protein tyrosine kinase, thereby inhibiting the growth of neovascularization in tumors and causing tumor cells to die without nutrients. Angi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D401/14A61K31/506A61K31/535A61P35/00C07D239/42C07D213/36
Inventor 庄明强赵京浦章雄文
Owner SHANGHAI XINXING MEDICINE
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