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Compound containing piperazinyl and piperazinyl triazole structures, and preparation method and applications thereof

A compound, dibromide technology, applied in its preparation, pharmaceuticals, piperazinyl and piperazine-triazole-containing compounds field

Inactive Publication Date: 2018-04-20
广东赛博科技有限公司
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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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  • Compound containing piperazinyl and piperazinyl triazole structures, and preparation method and applications thereof
  • Compound containing piperazinyl and piperazinyl triazole structures, and preparation method and applications thereof
  • Compound containing piperazinyl and piperazinyl triazole structures, and preparation method and applications thereof

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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

[0028] Compound II (2.50g, 10mmol), Compound III (2.06g, 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, ESI-MS, m / z=376 ([M+H] + ).

[0030] Step 2. Synth...

Embodiment 2

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

[0034]

[0035] Step 1. Synthesis of Compound IV

[0036] Compound II (2.50g, 10mmol), Compound III (2.06g, 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, ESI-MS, m / z=376 ([M+H] + ).

[0038] Step 2. Synthe...

Embodiment 3

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

[0042]

[0043] Step 1. Synthesis of Compound IV

[0044] Compound II (2.50g, 10mmol), Compound III (2.06g, 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, ESI-MS, m / z=376 ([M+H] + ).

[0046] Step 2. Synt...

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Abstract

The invention belongs to the field of SSAO inhibitor, and more specifically relates to a compound containing piperazinyl and piperazinyl triazole structures, a preparation method thereof, and applications of the compound in preparation of drugs used for treating inflammatory diseases, immune diseases, and tumor. In the formula (1), R is used for representing C1-C5 alkyl, and C3-C8 cycloalkyl.

Description

technical field [0001] The present invention relates to the field of SSAO inhibitors. Specifically, the present invention relates to a class of piperazinyl- and piperazine-triazole-containing compounds 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. [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P29/00A61P37/02A61P35/00
CPCC07D487/04
Inventor 郭会军
Owner 广东赛博科技有限公司
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