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Quinazoline compound and application thereof

A technology of quinazolines and compounds, which is applied in the field of medicine and can solve problems such as structural differences of compounds

Pending Publication Date: 2021-05-11
SHENYANG RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Patent CN 102977014B involves research on the in vitro anti-tumor inhibitory activity of compound A of the general formula, but the structure of the compound is significantly different from that of the compound of the present invention

Method used

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  • Quinazoline compound and application thereof
  • Quinazoline compound and application thereof
  • Quinazoline compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Embodiment 1: the preparation of compound 1

[0106]

[0107] Step 1: Add intermediate a (20g, 101mmol), ammonium formate (80mL) and formic acid (8mL) into a 250mL one-necked bottle, heat to 135°C and stir for 5 hours. Pour the reaction solution into a water bath to precipitate the product, and filter to obtain 23 g of the product.

[0108] Step 2: Add intermediate b (5g, 24.3mmol) to SOCl 2 (50mL), heated to reflux for 3h. After the reaction was completed, 5.3 g of the product was obtained by precipitation.

[0109] Step 3: Dissolve intermediate c (5.3g, 23.7mmol) and intermediate d (2.8g, 25.69mmol) in butanone (100mL), add NaOH (3g, 75mmol), H 2 O (20mL, 1.1mol) and TBAB (4g, 12mmol) were heated to 100°C for 4h. After the reaction, the product was purified by column chromatography to obtain 2.6g of the product.

[0110] Step 4: Dissolve intermediate e (100mg, 0.337mmol) and intermediate f (50mg, 0.325mmol) in THF (10mL), add DIPEA (200mg, 1.55mmol) and HBTU (1...

Embodiment 2

[0112] Embodiment 2: the preparation of compound 2

[0113]

[0114] The preparation method of intermediate e is the same as in Example 1. The preparation method of compound 2 is as follows:

[0115] Step 1: Dissolve intermediate e (100mg, 0.337mmol) and intermediate f (54mg, 0.325mmol) in THF (10mL), add DIPEA (200mg, 1.55mmol) and HBTU (130mg, 0.343mmol) and stir at room temperature for 6 100 mg of compound 2 was obtained by column chromatography.

[0116] 1H NMR(600MHz,DMSO-d6)δ10.23(s,1H),8.53(s,1H),7.71–7.66(m,2H),7.55(s,1H),7.37(s,1H),7.30– 7.26(m,2H),7.25–7.22(m,2H),6.92–6.88(m,2H),3.99(s,3H),3.97(s,3H),3.74(s,3H),3.59(s, 2H). MS: 445.16.

Embodiment 3

[0117] Embodiment 3: the preparation of compound 3

[0118]

[0119] The preparation method of intermediate e is the same as in Example 1. The preparation method of compound 3 is as follows:

[0120] Step 1: Dissolve intermediate e (100mg, 0.337mmol) and intermediate f (54mg, 0.325mmol) in THF (10mL), add DIPEA (200mg, 1.55mmol) and HBTU (130mg, 0.343mmol) and stir at room temperature for 6 Hours, column chromatography obtained 100 mg of compound 3 product.

[0121] 1H NMR (600MHz, DMSO-d6) δ10.17(s,1H),8.53(s,1H),7.74–7.66(m,2H),7.55(s,1H),7.38(s,1H),7.28– 7.22(m,4H),6.99(dd,J=8.1,1.1Hz,1H),6.92(td,J=7.4,1.1Hz,1H),3.99(s,3H),3.97(s,3H),3.79 (s,3H),3.66(s,2H).MS:445.16.

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Abstract

The invention relates to a quinazoline-containing compound as shown in a general formula (I), and a pharmaceutically acceptable salt, a solvate and a prodrug thereof, wherein substituent groups R1, R2, R3, R4, R5, R6, p, m and n are defined in the specification. The invention also relates to application of the compound shown in the general formula (I) in preparation of antitumor drugs, and also relates to application of the compound, the pharmaceutically acceptable salt, the solvate and the prodrug thereof in preparation and / or prevention and alleviation of cancers caused by tumor cells of human tissues or organs, wherein the cancers are preferably colon cancer, liver cancer, lymphoma, lung cancer, esophageal cancer, breast cancer, central nervous system tumor, melanoma, skin cancer, ovarian cancer, cervical cancer, kidney cancer, leukemia, prostate cancer, pancreatic cancer, bladder cancer, rectal cancer, osteosarcoma, nasopharyngeal cancer or gastric cancer and the like.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a quinazoline compound and its application in preventing and / or treating cancer. Background technique [0002] The literature European Journal of Medicinal Chemistry 107(2016) 12-25 involves the research on the mechanism of quinazoline compounds inhibiting the proliferation of HepG2, MGC-803, and A549 tumor cells, but has no effect on lung cancer, bladder cancer, colon cancer, leukemia, etc. Cancer Inhibition Research. [0003] [0004] Patent CN 102977014B involves the in vitro anti-tumor inhibitory activity research of compound A of the general formula, but the structure of the compound is significantly different from that of the compound of the present invention. [0005] [0006] Patent CN106632287A relates to quinazoline compounds having certain anticancer activity on human skin squamous cell carcinoma cell line A431 and human lung cancer cell line A549. [0007] ...

Claims

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Application Information

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IPC IPC(8): C07D239/88A61P35/00A61P35/02A61P31/00A61P29/00A61P37/02A61K31/517
CPCC07D239/88A61P35/00A61P35/02A61P31/00A61P29/00A61P37/02
Inventor 毕弋冉兆晋柴宝山王婉秋王云华焦佳媛吴依蒙赵宪成石凯强
Owner SHENYANG RES INST OF CHEM IND
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