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Pyrrolo[2,3-c]pyridine derivatives, their preparation method and their application in medicine

A technology of medicinal salts and compounds, which is applied in the fields of pharmaceutical formulations, drug combinations, antineoplastic drugs, etc.

Active Publication Date: 2021-12-31
JIANGSU HANSOH PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] BRD4 inhibitors have good application prospects as drugs in the pharmaceutical industry. There are no drugs on the market. In order to achieve better therapeutic effects and meet market demand, we hope to develop a new generation of selective BRD4 with high efficiency and low toxicity. Inhibitor

Method used

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  • Pyrrolo[2,3-c]pyridine derivatives, their preparation method and their application in medicine
  • Pyrrolo[2,3-c]pyridine derivatives, their preparation method and their application in medicine
  • Pyrrolo[2,3-c]pyridine derivatives, their preparation method and their application in medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0248] 4-(2-(2,4-difluorophenoxy)-5-(ethylsulfonimidoylmethyl)phenyl)-6-methyl-1,6-dihydro-7H-pyrrolo[ 2,3-c]pyridin-7-one

[0249]

[0250] The first step: 3-bromo-4-(2,4-difluorophenoxy)benzaldehyde

[0251]

[0252] Add 2,4-difluorophenol (1.47g, 11.33mmol), 3-bromo-4-fluorobenzaldehyde (2.30g, 11.33mmol), cesium carbonate (4.05g, 12.46mmol), dimethyl sulfoxide (10 mL). Heat the oil bath to 100°C, react for 1 hour, and cool to room temperature. The reaction solution is diluted with ethyl acetate (30 mL) and washed with saturated brine (10 mL x 3). The organic phase is dried over anhydrous sodium sulfate, filtered, and spin-dried. The crude product was purified by column chromatography (petroleum ether / ethyl acetate: 5 / 1) to obtain 3-bromo-4-(2,4-difluorophenoxy)benzaldehyde (2.60g, light yellow oil, product rate: 47%).

[0253] The second step: 3-bromo-4-(2,4-difluorophenoxy)benzyl alcohol

[0254]

[0255] 3-Bromo-4-(2,4-difluorophenoxy)benzaldehyde (2.60g, 8...

Embodiment 2

[0280] N-((4-(2,4-difluorophenoxy)-3-(6-methyl-7-carbonyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridine- 4-yl) benzyl) (ethyl) (carbonyl) -λ 6 -sulfanylidene)cyclopropanesulfonamide

[0281]

[0282] The first step: N-((4-(2,4-difluorophenoxy)-3-(6-methyl-7-carbonyl-1-toluenesulfonyl-6,7-dihydro-1H-pyrrole And[2,3-c]pyridin-4-yl)benzyl)(ethyl)(carbonyl)-λ 6 -sulfanylidene)cyclopropanesulfonamide

[0283]

[0284] 4-(2-(2,4-difluorophenoxy)-5-(ethylsulfimidoylmethyl)phenyl)-6-methyl-1-toluenesulfonyl-1,6-dihydro -7H-pyrrolo[2,3-c]pyridin-7-one (65.0mg, 0.11mmol) was dissolved in pyridine (2mL), cyclopropylsulfonyl chloride (200mg, 1.42mmol), DMAP (12mg, 0.1mmol) was added ) was stirred overnight at room temperature. Stop the reaction, add 1N hydrochloric acid solution (30mL), extract with ethyl acetate (30mLX2), combine the organic phases and wash with saturated sodium chloride (30mL), dry over anhydrous sodium sulfate, filter, concentrate, and separate with a preparative si...

Embodiment 3

[0292] 4-(2-(2,4-difluorophenoxy)-5-((N-methylethylsulfonimidoyl)methyl)phenyl)-6-methyl-1,6-dihydro -7H-pyrrolo[2,3-c]pyridin-7-one

[0293]

[0294] The first step: 4-(2-(2,4-difluorophenoxy)-5-((N-methylethylsulfonimidoyl)methyl)phenyl)-6-methyl-1- Tosyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

[0295]

[0296] 4-(2-(2,4-difluorophenoxy)-5-(ethylsulfimidoylmethyl)phenyl)-6-methyl-1-toluenesulfonyl-1,6-dihydro -7H-pyrrolo[2,3-c]pyridin-7-one (100mg, 0.16mmol), trimethyloxonium tetrafluoroboric acid (121mg, 0.82mmol), dichloromethane (5mL) in a reaction flask, After stirring at room temperature for 15 minutes, sodium carbonate (104 mg, 0.98 mmol) was added and reacted overnight at room temperature. Stop the reaction, add water (20mL), extract with ethyl acetate (30mLx2), combine the organic phases, wash with saturated sodium chloride (30mL), dry over anhydrous sodium sulfate, filter, concentrate the filtrate, and separate and purify by preparing a silica gel plate...

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Abstract

The invention discloses pyrrolo[2,3-c]pyridine derivatives, their preparation method and their application in medicine. In particular, the present invention discloses pyrrolo[2,3-c]pyridine derivatives represented by the general formula (I), their preparation methods and pharmaceutical compositions containing the derivatives, and their use as BRD4 inhibitors in the treatment of Uses for related diseases such as cancer, inflammation, chronic liver disease, diabetes, cardiovascular disease and AIDS, wherein each substituent in the general formula (I) is the same as defined in the description.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to pyrrolo[2,3-c]pyridine derivatives, their preparation methods and the application of pharmaceutical compositions containing the derivatives in medical research. The invention discloses that they are used as BRD4 inhibitors in It is used for the treatment of cardiovascular diseases such as cancer, inflammation, chronic liver disease, diabetes, dyslipidemia and related diseases such as AIDS. Background technique [0002] Tumor is one of the major diseases that seriously endanger human life, and more than half of it occurs in developing countries. The incidence of malignant tumors in my country is generally on the rise, and the incidence rate is increasing at an average annual rate of 3% to 5%. It is estimated that by 2020, 4 million people in my country will develop cancer and 3 million people will die of cancer. The main reasons are: Aging, urbanization, industrialization and changes in livi...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/4545A61P35/00A61P35/02A61P1/16A61P37/02A61P5/00A61P37/00A61K31/18
CPCY02P20/55A61K31/18A61K31/4545A61P1/16A61P5/00A61P35/00A61P35/02A61P37/00A61P37/02C07D471/04
Inventor 苏熠东古鹏陈晓坡刘磊包如迪
Owner JIANGSU HANSOH PHARMA CO LTD
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