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Oxime-containing amino derivatives, pharmaceutical composition thereof, preparation method and use thereof

A technology of amino and drugs, applied in the field of medicine and chemical industry, can solve problems such as difficult chemical synthesis, complex molecular structure, and difficulty in large-scale production

Active Publication Date: 2014-10-01
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the resources of these natural product drugs are limited, their molecular structure is complex, chemical synthesis is difficult, and it is not easy to produce on a large scale

Method used

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  • Oxime-containing amino derivatives, pharmaceutical composition thereof, preparation method and use thereof
  • Oxime-containing amino derivatives, pharmaceutical composition thereof, preparation method and use thereof
  • Oxime-containing amino derivatives, pharmaceutical composition thereof, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1: 3,4,5-trifluoro-2[(3-methyl-5-iodo-2-pyridyl)amino]benzaldehyde (Compound 1) Preparation

[0071] Step 1), the preparation of 2,3,4,5-tetrafluorobenzoic acid methyl ester: 2,3,4,5-tetrafluorobenzoic acid (48.5g, 0.25mol) was dissolved in 130mL of anhydrous methanol, slowly Chlorotrimethylsilane (63 mL, 0.50 mol) was added dropwise. After the dropwise addition, reflux for 12h. Evaporate the solvent and excess trimethylchlorosilane under reduced pressure with a water pump to obtain a light yellow liquid, add 200mL of dichloromethane, and wash with 10% aqueous sodium hydroxide solution, extract the water layer with dichloromethane, combine the organic layers, and Dry overnight with anhydrous sodium sulfate. The next day, it was filtered, and the solvent was evaporated under reduced pressure to obtain a colorless liquid, methyl 2,3,4,5-tetrafluorobenzoate (30.52 g, 97.8%). 1 H-NMR (400MHz, CDCl 3 ) δppm: 7.65-7.60 (m, 1H), 3.97 (s, 1H).

[0072] Step 2), ...

Embodiment 2

[0079] Example 2: (R, E)-3,4,5-trifluoro-2-[(3-methyl-5-iodo-2-pyridyl)ammonia base]-O-(2,3-dihydroxypropyl)benzaldoxime (compound 2)

[0080] Step 1), (R,E)-3,4,5-trifluoro-2-[(3-methyl-5-iodo-2-pyridyl)amino]-O-[(2,2-methyl- The preparation of 1,3 dioxolane-4 base) methyl] benzaldehyde oxime: 3,4,5-trifluoro-2-[(3-methyl-5-iodo-2-pyridyl)amino] Benzaldehyde (0.4 g, 0.98 mmol) and (R)O-{3[(tert-butyl-dimethylsilyl)oxy]propyl}hydroxylamine (0.30 g, 2.05 mmol) were dissolved in 10 mL of absolute ethanol, Heat to reflux and react for 2h. The reaction system was directly mixed with crude silica gel, and a yellow solid was obtained by column chromatography, which was directly used in the next reaction, ESI-MS m / z: 521.1[M+1] + .

[0081] Step 2), (R,E)-3,4,5-trifluoro-2-[(3-methyl-5-iodo-2-pyridyl)amino]-O-(2,3-dihydroxypropyl ) Preparation of benzaldoxime: (R, E)-3,4,5-trifluoro-2-[(3-methyl-5-iodo-2 pyridyl)amino]-O-[(2,2 -Methyl-1,3-dioxolan-4-yl)methyl]benzaldehyde ox...

Embodiment 3

[0082] Example 3: (E)-3,4,5-trifluoro-2-[(3-methyl-5-iodo-2-pyridyl)ammonia base]--O-(2,3-dihydroxypropyl)benzaldehyde oxime (compound 3)

[0083] The method is the same as in Example 2 to obtain a pale yellow solid. 1 H-NMR (400MHz, DMSO-D 6 )δppm: 8.26-8.22 (m, 1H), 7.71 (s, 1H), 7.65-7.61 (m, 1H), 7.47-7.45 (m, 1H), 7.34-7.32 (m, 1H), 4.70 (br s , 2H), 4.18-4.15(m, 1H,), 4.03-4.01(m, 1H), 3.72-3.70(m, 1H), 3.38-3.34(d, 2H, J=5.6Hz), 2.26(s, 3H). ES I-MS m / z: 482.0[M+1] + .

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Abstract

Disclosed in the present invention is an oxime-containing amino derivative, and the pharmaceutical composition, preparation method and use thereof. In particular, the oxime-containing amino derivative is as shown in formulae ? or ?, wherein each substituent is as described in the specification. The oxime-containing amino derivative of the present invention can effectively inhibit tumour cells, so it can be used as an anti-tumour drug.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to an amino derivative containing oxime, its pharmaceutical composition, its preparation method and application. Background technique [0002] Cancer is a disease that seriously threatens human health. Since the advent of the first anticancer drug, nitrogen mustard, in the 1940s, scientists have isolated and extracted several natural products with potential cytotoxic activity from plants. Active compounds, among which vinblastine, etoposide, paclitaxel, etc. have been approved for clinical treatment of cancer. However, the resources of these natural product drugs are limited, their molecular structure is complex, chemical synthesis is difficult, and it is not easy to produce on a large scale. Therefore, it is necessary to find small molecule antitumor drugs with simple structures. Contents of the invention [0003] The present inventor obtained a new class of oxime-c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/74C07C223/06C07C221/00C07C251/54C07C249/12C07D401/12A61K31/44A61K31/136A61K31/15A61K31/4439A61P35/00A61P35/02
CPCC07D401/12A61K31/15C07D213/74C07C2101/02C07C251/54C07C223/06A61K31/435A61K31/4184A61P35/00A61P35/02C07C2601/02
Inventor 李松郑志兵樊士勇王莉莉钟武刘洪英肖军海谢云德周辛波陈伟李行舟
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A