Bicyclic fused heterocyclic compound, its preparation method and use
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A compound and composition technology, applied in the field of medicine, can solve the problems of genotoxicity, mutagenesis, toxic and side effects, etc.
Inactive Publication Date: 2016-01-20
邹宏丽
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Chemotherapy is faster, but the cure rate is very low
At the same time, it is clinically found that many anticancer drugs have obvious damage and side effects on the normal body, such as mutagenesis and genotoxicity
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Embodiment 1
[0030] Embodiment 1: the synthesis of compound 1
[0031]
[0032] Synthesis of compound 1a:
[0033] Dissolve 18.4g (100mmol) of 7-chloro-5-methyl-[1,2,4]triazol[4,3-c]pyrimidin-3-amine in 300mL ethanol, add 10mL85% hydrazine hydrate, room temperature The reaction was stirred vigorously for 14 hours. A white solid was obtained by filtration, washed with ethanol and dried to obtain 18.4 g of compound 1a as a white solid, with a yield of 95%.
[0034] MS(m / z):180.10[M+H] +
[0035] Synthesis of compound 1b:
[0036] Dissolve 17.6g (100mmol) of benzenesulfonyl chloride in 20mL of dichloromethane, cool to 0°C, and slowly add 10mL of pyridine dropwise to obtain a clear, colorless liquid; then dissolve 14.4g (40mmol) of compound 1a in 200mL of dichloromethane Slowly added to the reaction system, stirred overnight at room temperature. The solvent was recovered under reduced pressure and separated by column chromatography to obtain 5.8 g of white solid compound 1b with a yie...
Embodiment 2
[0046] Embodiment 2: the synthesis of compound 2
[0047]
[0048] The method is the same as in Example 1, except that 1-naphthaldehyde is used instead of benzaldehyde to obtain a light yellow solid. Yield: 72%.
[0049] MS(M / Z):598.23[M+H] +
[0050] Elemental analysis: theoretical value / measured value, C (60.29 / 60.20), H (5.23 / 5.29), N (21.09 / 21.18), O (8.03 / 7.93), S (5.36 / 5.40).
Embodiment 3
[0051] Embodiment 3: the synthesis of compound 3
[0052]
[0053] The method is the same as in Example 1, except that 4-methylpiperazin-1-amine is used instead of 4-methylpiperidin-1-amine to obtain a white solid. Yield: 70%.
[0054] MS(M / Z):549.21[M+H] +
[0055] Elemental analysis: theoretical value / measured value, C (54.73 / 54.63), H (5.14 / 5.19), N (25.53 / 25.58), O (8.75 / 8.71), S (5.84 / 5.88).
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Abstract
The invention relates to the field of anti-tumor related drugs, and provides a bicyclic condensed heterocyclic compound or a pharmaceutically acceptable salt thereof. The present invention also provides the preparation method of the bicyclic fused heterocyclic compound or its pharmaceutically acceptable salt, its pharmaceutical composition and its use as an active ingredient in the preparation and treatment of small cell lung cancer, breast cancer, liver cancer, colon cancer, malignant nerve Application of anti-tumor drugs such as glioma, brain tumor, leukemia or pancreatic cancer.
Description
technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a bicyclic condensed heterocyclic compound, a preparation method thereof, a pharmaceutical composition and an application for preparing antitumor drugs. Background technique [0002] Cancer has become a major chronic disease that seriously endangers human health. According to statistics, there are 9 million people who suffer from cancer every year in the world, and 6 million patients die from cancer. Almost one cancer patient dies every second. The annual incidence of cancer in my country is about 1.2 million, the number of cancer deaths is as high as more than 900,000, and the number of patients waiting for treatment exceeds 1.5 million, and there is an increasing trend year by year. Therefore, cancer has become the second largest killer after cardiovascular disease. Clinically, tumors are treated in three major ways: surgery, radiotherapy, and chemotherapy. Altho...
Claims
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