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Adamantine and alcoxyl containing pyridine structural compound, as well as preparation method and application thereof

A technology of compound and alkyl, applied in the field of SSAO inhibitor

Inactive Publication Date: 2018-04-20
FOSHAN HANFANG CHINESE MEDICINE HOSPITAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The precise physiological role of this abundant enzyme has not been fully determined, but it appears that SSAO and its reaction products may have several functions in cellular signal transduction and regulation

Method used

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  • Adamantine and alcoxyl containing pyridine structural compound, as well as preparation method and application thereof
  • Adamantine and alcoxyl containing pyridine structural compound, as well as preparation method and application thereof
  • Adamantine and alcoxyl containing pyridine structural compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of embodiment 1 compound I-1

[0026]

[0027] Step 1. Synthesis of compound IV-1

[0028] Compound II-1 (2.37g, 10mmol), Compound III (1.07g, 10mmol), Pd(OAc) 2 (0.22g, 1mmol), BINAP (2,2'-bisdiphenylphosphino-1,1'-binaphthyl, 0.62g, 1mmol) and t-BuOK (2.24g, 20mmol) were added to 50mL dry 1 , 2-dimethoxyethane (DME), the reaction mixture was stirred overnight under nitrogen atmosphere, TLC detection found that the reaction was complete.

[0029] The reaction mixture was carefully poured into 200mL ice water, stirred, and washed with 50mL×3CH 2 Cl 2 After extraction, the extract phases were combined, washed successively with 1% dilute hydrochloric acid and brine, 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 residue was purified by silica gel column chromatography to obtain compound IV-I, 1.76 g (67% yield). ESI-MS, m / z=264 ([M+H] +...

Embodiment 2

[0033] The synthesis of embodiment 2 compound 1-2

[0034]

[0035] Step 1. Synthesis of compound IV-2

[0036] Compound II-2 (2.67g, 10mmol), Compound III (1.07g, 10mmol), Pd(OAc) 2 (0.22g, 1mmol), BINAP (2,2'-bisdiphenylphosphino-1,1'-binaphthyl, 0.62g, 1mmol) and t-BuOK (2.24g, 20mmol) were added to 50mL dry 1 , 2-dimethoxyethane (DME), the reaction mixture was stirred overnight under nitrogen atmosphere, TLC detection found that the reaction was complete.

[0037] The reaction mixture was carefully poured into 200mL ice water, stirred, and washed with 50mL×3CH 2 Cl 2 After extraction, the extract phases were combined, washed successively with 1% dilute hydrochloric acid and brine, 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 residue was purified by silica gel column chromatography to obtain compound IV-2. ESI-MS, m / z=294 ([M+H] + ).

[0038] Step 2....

Embodiment 3

[0041] The synthesis of embodiment 3 compound 1-3

[0042]

[0043] Step 1. Synthesis of compound IV-3

[0044] Compound II-3 (2.81g, 10mmol), Compound III (1.07g, 10mmol), Pd(OAc) 2 (0.22g, 1mmol), BINAP (2,2'-bisdiphenylphosphino-1,1'-binaphthyl, 0.62g, 1mmol) and t-BuOK (2.24g, 20mmol) were added to 50mL dry 1 , 2-dimethoxyethane (DME), the reaction mixture was stirred overnight under nitrogen atmosphere, TLC detection found that the reaction was complete.

[0045] The reaction mixture was carefully poured into 200mL ice water, stirred, and washed with 50mL×3CH 2 Cl 2 After extraction, the extract phases were combined, washed successively with 1% dilute hydrochloric acid and brine, 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 residue was purified by silica gel column chromatography to obtain compound IV-3. ESI-MS, m / z=308 ([M+H] + ).

[0046] Step ...

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PUM

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Abstract

The invention relates to the field of SSAO inhibitors, and specifically relates to an adamantine and alcoxyl containing pyridine structural compound, a preparation method of the compound, and application of the compound to preparation of medicines for treating inflammatory diseases, immune diseases, tumors, and the like. The adamantine and alcoxyl containing pyridine structural compound is shown in the description, wherein R is selected from alkyls of C1-C5 and naphthenic bases of C3-C6.

Description

technical field [0001] The present invention relates to the field of SSAO inhibitors. Specifically, the present invention relates to a class of compounds containing adamantane and alkoxypyridine structures that have a therapeutic effect on inhibiting SSAO, their preparation methods, and their use in pharmacy. Background technique [0002] Semicarbazide-sensitive amine oxidase (SSAO) activity is produced by vascular adhesion protein-1 (Vascular Adhesinon Protein-1, VAP-1) or copper-containing amine oxidase (AmoneOxidase, Copper Containing 3, AOC3 ), which belongs to the family of copper-containing amine oxidases (EC.1.4.3.6). Therefore, inhibitors of SSAO enzymes can also regulate the biological functions of VAP-1 protein. Members of this enzyme family are sensitive to inhibition by semicarbazides and use copper ions and the protein-derived hydroxydopaquinine (TPQ) cofactor for the oxidation of primary amines to aldehydes, hydrogen peroxide, and ammonia Deamination. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A61P29/00A61P37/00A61P35/00
CPCC07D401/04
Inventor 朱斌
Owner FOSHAN HANFANG CHINESE MEDICINE HOSPITAL CO LTD
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