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Carbazole STAT3 inhibitor crystal form A and preparation method thereof

A technology of carbazole and crystal form, which is applied in the field of medicinal chemistry, can solve the problems that affect the process of prescription preparations, storage methods, pharmacokinetic performance in vivo, and affect the safety and effectiveness of drugs, and achieve good stability.

Inactive Publication Date: 2019-02-15
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These differences directly affect the prescription preparation process, storage method, and pharmacokinetic performance of the drug in vivo, which in turn affects the safety and effectiveness of the drug.

Method used

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  • Carbazole STAT3 inhibitor crystal form A and preparation method thereof
  • Carbazole STAT3 inhibitor crystal form A and preparation method thereof
  • Carbazole STAT3 inhibitor crystal form A and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Preparation of 2-aminomethyl-4H-chromen-4-one hydrochloride

[0043] The preparation of step 1 2-acetoxyacetophenone

[0044]

[0045] Add 2-hydroxyacetophenone (100mmol), acetyl chloride (250mmol) and potassium carbonate (500mmol) into the reaction flask, add 300ml of acetone, reflux reaction for 12h, after the reaction, evaporate the solvent under reduced pressure, add water, ethyl acetate Esters were extracted, dried over anhydrous sodium sulfate, and concentrated to obtain an oil, which was directly used for the next step.

[0046] Step 2 Preparation of 2-methyl-4H-chromen-4-one

[0047]

[0048] Weigh 2-acetoxyacetophenone (50mmol) into a reaction flask, add 100ml DMSO to dissolve, add sodium hydrogen (150mmol) in batches at 0-5°C, after the addition is complete, raise it to room temperature and stir for 3h. After the reaction, Add water to the reaction solution, dilute hydrochloric acid to adjust the pH value to weak acidity, extract with ethyl a...

Embodiment 2

[0058] Example 2 Preparation of 2,4-dichloro-6-(4-nitrophenyl)-1,3,5-triazine

[0059] Preparation of step 1 methyl 4-nitrobenzoate

[0060]

[0061] Weigh 4-nitrobenzoic acid (250mmol) in a reaction flask, add 300mL of methanol to dissolve, add thionyl chloride (375mmol) dropwise, and reflux for 12 hours after the dropwise reaction. After the reaction, spin dry under reduced pressure and add saturated bicarbonate The sodium solution adjusted the pH to 7-8, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated to obtain the title compound, which was directly used for the next step.

[0062] Step 2 Preparation of 6-(4-nitrophenyl)-1,3,5-triazine-2,4-(1H,3H)-dione

[0063]

[0064] Weigh biuret (100mmol) into the reaction flask, add 150mL ethylene glycol dimethyl ether to dissolve, add sodium hydride (83.4mmol) in batches at 0-5°C, after the addition is complete, stir the reaction at 50°C for 1h, then add 4-Nitrobenzoic acid methyl ester (83...

Embodiment 3

[0070] Example 3 4-chloro-6-(4-nitrophenyl)-N-(2-methyl-4H-chromene-4-one base)-1,3,5-triazin-2-amine preparation

[0071]

[0072] Weigh 2,4-dichloro-6-(4-nitrophenyl)-1,3,5-triazine (50mmol) obtained in Example 2 into a reaction flask, add 100mL tetrahydrofuran to dissolve, add Example 1 The resulting 2-aminomethyl-4H-chromen-4-one hydrochloride 2-(trifluoromethyl)-pyridin-4-amine (55mmol), sodium carbonate (100mmol), reflux for 72h, filter, column Chromatographic purification afforded the title compound.

[0073] ES: M / Z 416[M+H] + .

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Abstract

The invention belongs to the field of medical chemistry and particularly relates to a novel crystal form of a compound 4-(9-ethyl-9H-carbazole-4)-6-(4-acrylyl aminophenyl)-N-(2-methyl-4H-chromene-4-ketone)-1,3,5-triazine-2-amine mesylate with an anti-tumor effect, a preparation method of the novel crystal form, a composition comprising the crystal form, and an application of the crystal form or the composition comprising the crystal form in medicine preparation. The crystal form A has good physical and chemical stability, solubility and bioavailability and is suitable for preparation development.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a compound 4-(9-ethyl-9H-carbazol-4-yl)-6-(4-acryloylaminophenyl)-N-(2- A new crystal form of methyl-4H-chromen-4-one)-1,3,5-triazine-2-amine methanesulfonate, its preparation method, and a composition comprising the crystal form, As well as the use of the crystal form or the composition comprising the crystal form in the preparation of medicines. Background technique [0002] Cancer is a general term for a large class of malignant tumors, which is characterized by unlimited and endless proliferation. Cancer cells consume a large amount of nutrients in the patient's body, and at the same time release a variety of toxins, causing a series of symptoms in the human body, resulting in weight loss, weakness, anemia, loss of appetite, fever, and serious organ function damage, causing necrosis and bleeding Co-infection, the patient eventually died due to organ failure. [0003] Sig...

Claims

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Application Information

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IPC IPC(8): C07D405/14A61K31/53A61P35/00
CPCA61P35/00C07D405/14C07B2200/13
Inventor 郭程杰
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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