2,3-dihydro-4(1H)- quinazolone derivative and application thereof

A quinazolone and derivative technology, which can be used in drug combinations, cardiovascular system diseases, respiratory system diseases, etc., and can solve the problems of poor tumor curative effect, toxic and side effects, etc.

Inactive Publication Date: 2011-01-05
SHANGAI PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, currently clinically used angiogenesis inhibitors have also been found to have varying degrees of toxicity and side effects, and...

Method used

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  • 2,3-dihydro-4(1H)- quinazolone derivative and application thereof
  • 2,3-dihydro-4(1H)- quinazolone derivative and application thereof
  • 2,3-dihydro-4(1H)- quinazolone derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Example 1, 2-(4,5-dibromo-2-thienyl)-6-nitro-2,3-dihydroquinazolin-4(1H)-one

[0058]

[0059] step:

[0060] Sequentially weigh 5-nitro-2-aminobenzamide (0.181g, 1mmol) and 4,5-dibromo-2-thiophene aldehyde (0.270g, 1mmol) in a 5mL round bottom flask, add 3mL formic acid, room temperature After stirring, a large amount of yellow solids were precipitated. After 5 minutes, TLC detected that the reaction was complete. Stopped the reaction, filtered the yellow solids, and dried them in vacuum at 40° C. for 6 hours to obtain 0.380 g of yellow solids. The yield was 88%, and the purity by HPLC was 98.29%, m.p. : 261-263°C.

[0061] 1 H NMR (DMSO-d 6, ppm) δ: 9.03 (1H, d, J = 1.2Hz), 8.73 (1H, s), 8.42 (1H, d, J = 2.7Hz), 8.15 (1H, dd, J = 9.0, 3.0Hz), 7.15 (1H, d, J = 0.6Hz), 6.89 (1H, d, J = 9.0Hz), 6.27 (1H, t, J = 2.4Hz)

[0062] EI-MS (m / z): 431 (M +. C 12 h 7 79 Br 2 N 3 o 3 S, 50), 352 (M- 79 Br, 55), 192(80), 165(100), 146(30), 119(30)

Embodiment 2

[0063] Example 2, 2-(4-bromo-2-thienyl)-6-nitro-2,3-dihydroquinazolin-4(1H)-one

[0064]

[0065] The operation steps are the same as in Example 1, yellow solid, m.p.: 243-247°C

[0066] 1 H NMR (DMSO-d 6 , ppm) δ: 8.99 (1H, s), 8.72 (1H, s), 8.42 (1H, d, J=3.0Hz), 8.14 (1H, dd, J=9.0, 2.4Hz), 7.64 (1H, d , J=1.8Hz), 7.16 (1H, d, J=1.2Hz), 6.88 (1H, d, J=9.0Hz), 5.29 (1H, t, J=2.4Hz)

[0067] EI-MS (m / z): 353 (M + .C 12 h 8 79 BrN 3 o 3 S, 100), 323 (M- 79 Br, 80), 274(40), 192(29), 165(85), 146(15), 134(16), 119(25), 90(45)

Embodiment 3

[0068] Example 3, 2-(4-bromo-2-thienyl)-7-chloro-2,3-dihydroquinazolin-4(1H)-one,

[0069]

[0070] step:

[0071] Sequentially weigh 4-chloro-2-aminobenzamide (0.181g, 1mmol) and 4,-bromo-2-thiophene aldehyde (0.270g, 1mmol) in a 5mL round bottom flask, add 5mL of ethanol, stir at room temperature, there is A large amount of white solids precipitated out, and the reaction was stopped after the completion of the reaction by TLC, concentrated under reduced pressure, and subjected to silica gel column chromatography to obtain 0.380 g of white solids with a yield of 88%, m.p.: 201-202°C.

[0072] 1 H NMR (DMSO-d 6 , ppm) δ: 8.67 (1H, s), 7.62 (1H, s), 7.59 (2H, s), 7.12 (1H, s), 6.81 (1H, s), 6.73 (1H, dd, J=8.4, 1.2Hz), 6.06 (1H, s) EI-MS (m / z): 342 (M +. C 12 h 8 79 Br 35 ClN 2 OS, 44), 263 (M- 79 Br, 23), 181(45), 154(100), 126(40)

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Abstract

The invention discloses a substituted 2,3-dihydro-4(1H)- quinazolone derivative shown in the formula I, pharmaceutically acceptable salt or solvate and a drug composite containing the same and application thereof. The compound has very good effect of restraining vascular endothelial cell proliferation. The compound, the pharmaceutically acceptable salt or solvate or the drug composite containing the same can be used for drugs requiring to restraining angiogenesis diseases and/or cytotoxicity exerting diseases.

Description

technical field [0001] The present invention specifically relates to a 2,3-dihydro-4(1H)-quinazolone derivative, its pharmaceutically acceptable salt or solvate, and its pharmaceutical composition and application. Background technique [0002] Angiogenesis is the process of generating new blood vessels from pre-existing vascular beds. Under normal circumstances, angiogenesis is strictly controlled in some transient, specific physiological processes, such as: reproductive process, developmental process and wound healing process. Sustained angiogenesis is the performance of certain diseases, such as: malignant growth of tumor tissue, diabetic retinopathy and so on. [0003] Studies have shown that tumor is an angiogenesis-dependent disease, and the growth, invasion and metastasis of primary tumors all require the generation of new blood vessels. Neovascularization provides sufficient oxygen and nutrients for tumor cells, and its endothelial cells express a variety of growth ...

Claims

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Application Information

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IPC IPC(8): C07D409/04A61K31/517A61P35/00A61P9/10A61P29/00A61P19/04A61P37/06A61P27/06A61P27/02A61P11/02A61P43/00
Inventor 夏广新沈竞康陈茜刘学军李萍
Owner SHANGAI PHARMA GRP CO LTD
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