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Anti-tumor medicine in double-aryl urea structure based on indazole, indole, azaindazole or azaindole

An anti-tumor drug, the technology of azaindole, which is applied in the field of anti-tumor drugs and anti-tumor drugs with bisaryl urea structure, can solve the problems of anti-tumor drugs with bis-aryl urea structure that have not been found yet

Inactive Publication Date: 2013-12-18
JINAN HAILE MEDICAL TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, no patents have been found for antitumor drugs based on indazole, indole or azaindazole, azaindole bisaryl urea structure and pharmaceutically acceptable salts (the following formulas Ia and Ib) or other literature reports

Method used

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  • Anti-tumor medicine in double-aryl urea structure based on indazole, indole, azaindazole or azaindole
  • Anti-tumor medicine in double-aryl urea structure based on indazole, indole, azaindazole or azaindole
  • Anti-tumor medicine in double-aryl urea structure based on indazole, indole, azaindazole or azaindole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Example 1: N-{5-[2-(4-chloro-1-indazolyl)]pyridyl}-N'-(4-chloro-3-trifluoromethylphenyl)urea p-toluenesulfonic acid Salt (1):

[0080]

[0081] 2.0 g (13 mmol) of 4-chloroindazole and 2.1 g (13 mmol) of 2-chloro-5-nitropyridine were dissolved in 20 mL of DMF, 5.2 g (16 mmol) of cesium carbonate was added, and the reaction was stirred at 50°C for 5 h. The reactant was poured into ice water, and a yellow precipitate was precipitated. Suction filtration, washing with water, and drying gave 3.2 g of 4-chloro-1-(5-nitro-2-pyridyl)indazole with a yield of 90%, which was directly used in the next reaction.

[0082] Dissolve the above compound in 40mL of acetic acid, add a solution of 1.7g of ammonium chloride dissolved in 20mL of water, then add 3.4g of reduced iron powder, and reflux for 4h. After filtration, it was concentrated under reduced pressure. The residue was added to water, and a pale yellow solid was precipitated. The solid was dissolved in ethyl acetate and...

Embodiment 2

[0085] Example 2: N-{5-[2-(1-indolyl)]pyridyl}-N'-(4-chloro-3-trifluoromethylphenyl)urea p-toluenesulfonate (2) :

[0086]

[0087] Dissolve 2.34g (20mmol) of indole and 3.18g (20mmol) of 2-chloro-5-nitropyridine in 40mL DMF, add 7.82g (24mmol) of cesium carbonate, and stir the reaction at 50°C for 5h. After the reaction was completed, the reactant was poured into ice water, and a yellow precipitate was precipitated. Suction filtration, washing with water, and drying yielded 4.32 g of 1-(5-nitro-2-pyridyl)indole, which was directly used in the next reaction.

[0088] The above compound was dissolved in 50mL of ethanol, a solution of 3.24g (60mmol) of ammonium chloride dissolved in 20mL of water was added, and 6.7g (120mmol) of reduced iron powder was added, and the reaction was refluxed for 6h. After the reaction was completed, the temperature was lowered, filtered and concentrated under reduced pressure. Extract with ethyl acetate, dry over anhydrous magnesium sulfate, ...

Embodiment 3

[0090] Example 3: N-{2-[5-(4-chloro-1-indazol)yl]pyridyl}-N'-(4-chloro-3-trifluoromethylphenyl)urea (3):

[0091]

[0092] 1.5g (10mmol) of 4-chloroindazole and 1.59g (10mmol) of 5-chloro-2-nitropyridine were dissolved in 20mL DMF, 3.5g (11mmol) of cesium carbonate was added, and the reaction was stirred at 50°C for 5h. The reactant was poured into ice water, and a yellow precipitate was precipitated. Suction filtration, washing with water, and drying gave 2.4 g of 1-(4-nitro-5-pyridyl)-4-chloroindazole with a yield of 90%, which was directly used in the next reaction.

[0093] The above compound was dissolved in 40 mL of ethanol, a solution of 1.62 g of ammonium chloride dissolved in 20 mL of water was added, and 3.4 g of reduced iron powder was added, and the reaction was refluxed for 4 h. After filtration, it was concentrated under reduced pressure. The residue was added to water, and 0.73 g of light yellow solid 1-(2-amino-5-pyridyl)-4-chloroindazole was precipitated,...

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Abstract

The invention belongs to the field of medicines, relates to anti-tumor medicines, and in particular relates to anti-tumor medicines in double-aryl urea structures based on indazole, indole, azaindazole or azaindole. The structural formulae of the anti-tumor medicines are shown in formula (Ia) and formula (Ib), wherein Z is N atom or C atom; W is O; M is O, S, N or CH; n is 1 or 2; Y and R are halogen atoms, H, R1, CF3, OCF3, OH, OR2, OCOR3, NH2, NHR4, NR52, NHCOR6, carboxyl group, ester group, cyano group, mercapto group, alkyl sulphanyl, sulfuryl, sulfoxide, sulfonic group, sulfamate, sulfonamide, ketonic group, aldehyde group, nitro group or nitroso group. Pharmacodynamic experiments prove that the medicines have good anti-tumor effects on human lung cancer, human kidney cancer, human colon cancer, human liver cancer, human gastric cancer, human breast cancer, melanoma and the like.

Description

technical field [0001] The invention belongs to the field of medicines, and relates to a class of antineoplastic drugs, in particular to an antineoplastic drug based on indazole, indole or azaindazole, azaindole bisaryl urea structure. Pharmacological experiments have proved that these drugs have good anti-tumor effects on human breast cancer, human liver cancer, human kidney cancer, human colon cancer, human gastric cancer, human lung cancer, and melanoma. Background technique [0002] According to statistics, there are as many as 12 million cancer patients diagnosed in the world, and more than 7 million patients die of cancer every year. Cancer has become one of the deadliest diseases in the world. [0003] Renal cell carcinoma (RCC), a form of kidney cancer arising from renal tubular cells, accounts for 90-95% of kidney tumors and approximately 2% of adult malignancies. Renal cell carcinoma is the sixth leading cause of cancer death, with an estimated 95,000 deaths worl...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D471/04A61P35/00
Inventor 李文保李刚楚洋洋孙昌俊
Owner JINAN HAILE MEDICAL TECH DEV
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