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Xanthate compound containing halothiophene and nitrobenzene hexamethylbenzene structure, preparation method and application

A compound and halogen technology, applied in the field of xanthate AMPK activators, can solve the problem of multiple toxic and side effects

Inactive Publication Date: 2015-09-30
FOSHAN SAIWEISI MEDICINE SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although metformin is less likely to cause lactic acidosis than phenformin, it has the most clinical reports of severe toxic side effects and death among oral hypoglycemic drugs. Therefore, the development of new, non-biguanide AMPK activators as Drugs for the treatment of diabetes have important clinical significance

Method used

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  • Xanthate compound containing halothiophene and nitrobenzene hexamethylbenzene structure, preparation method and application
  • Xanthate compound containing halothiophene and nitrobenzene hexamethylbenzene structure, preparation method and application
  • Xanthate compound containing halothiophene and nitrobenzene hexamethylbenzene structure, preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The synthesis of embodiment 1 compound I-1

[0021]

[0022] A. Synthesis of Compound IV-1

[0023] Compound II (1.48 g, 10 mmol) and compound III-1 (2.01 g, 10 mmol) were dissolved in 20 mL of dry CH 2 Cl 2 , stirred at room temperature, added anhydrous AlCl 3 (1.33 g, 10 mmol), then the reaction mixture was stirred overnight at room temperature, TLC showed the reaction was complete. The reaction mixture was poured into 200 mL of ice water, stirred, and washed with CH 2 Cl 2 (60mL×3) for extraction, combined the extract phases, washed with 1% dilute hydrochloric acid and brine successively, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound IV-1 as a white solid. ESI-MS, m / z=314 ([M+H] + ).

[0024] B. Synthesis of Compound V-1

[0025] Compound IV-1 (1.88g, 6mmol) was dissol...

Embodiment 2

[0030] The synthesis of embodiment 2 compound 1-2

[0031]

[0032] A. Synthesis of Compound IV-1

[0033] Compound II (1.48 g, 10 mmol) and compound III-1 (2.01 g, 10 mmol) were dissolved in 20 mL of dry CH 2 Cl 2 , stirred at room temperature, added anhydrous AlCl 3 (1.33 g, 10 mmol), then the reaction mixture was stirred overnight at room temperature, TLC showed the reaction was complete. The reaction mixture was poured into 200 mL of ice water, stirred, and washed with CH 2 Cl 2 (60mL×3) for extraction, combined the extract phases, washed with 1% dilute hydrochloric acid and brine successively, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain compound IV-1 as a white solid. ESI-MS, m / z=314 ([M+H] + ).

[0034] B. Synthesis of Compound V-1

[0035] Compound IV-1 (1.88g, 6mmol) was disso...

Embodiment 3

[0040] The synthesis of embodiment 3 reference compound D-1

[0041] In order to further illustrate the good effect of the compound of the present invention, the application records the compound D-1, which is also invented by the applicant and has not yet been disclosed, and its structure is as follows:

[0042]

[0043] The synthesis method is as follows:

[0044]

[0045] A. Synthesis of Compound IV-2

[0046] Compound II (1.48 g, 10 mmol) and compound III-2 (1.57 g, 10 mmol) were dissolved in 20 mL of dry CH 2 Cl 2 , stirred at room temperature, added anhydrous AlCl 3 (1.33 g, 10 mmol), then the reaction mixture was stirred overnight at room temperature, TLC showed the reaction was complete. The reaction mixture was poured into 200 mL of ice water, stirred, and washed with CH 2 Cl 2 (60mL×3) for extraction, combined the extract phases, washed with 1% dilute hydrochloric acid and brine successively, and dried over anhydrous sodium sulfate. The desiccant was re...

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Abstract

The invention relates to pharmaceutical field related to 2-diabetes mellitus, in particular to a xanthate activating agent containing containing halothiophene and nitrobenzene hexamethylbenzene structure and a preparation method and the application in the preparation process for 2-diabetes mellitus drugs. R is selected from halogen substituent group.

Description

technical field [0001] The invention relates to the field of drugs for the treatment of type 2 diabetes. More specifically, the present invention relates to a class of xanthate AMPK activators containing halogenated thiophene and nifexylene structures, which have a therapeutic effect on type 2 diabetes, its preparation method, and its use in pharmacy. Background technique [0002] Diabetes is a disease process of multiple etiologies that affects 6% of the world's population. It is estimated that by 2025, the number of patients will double to 300 million. The most important clinicopathological feature of diabetes is increased plasma glucose (blood sugar) concentration. Increased blood sugar concentration is the main cause of various clinical symptoms of diabetes. Uncontrolled hyperglycemia leads to many diabetic complications, such as increased risk of microvascular and macrovascular diseases, including nephropathy, neuropathy, retinopathy, hypertension, cerebral ischemia ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/18A61P3/10
CPCC07D333/18
Inventor 邓润卿
Owner FOSHAN SAIWEISI MEDICINE SCI & TECH
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