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SSAO inhibitor containing adamantane structure as well as preparation method and application thereof

A technology of alkyl and cycloalkyl, applied in the field of SSAO inhibitors

Inactive Publication Date: 2019-07-09
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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  • SSAO inhibitor containing adamantane structure as well as preparation method and application thereof
  • SSAO inhibitor containing adamantane structure as well as preparation method and application thereof
  • SSAO inhibitor containing adamantane structure as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Synthesis of Compound I-1

[0028]

[0029] Step 1. Synthesis of Compound IV-1

[0030] Compound II-1 (2.37g, 10mmol), Compound III (1.07g, 10mmol), Pd(OAc) 2 (0.22 g, 1 mmol), BINAP (2,2'-bisdiphenylphosphino-1,1'-binaphthyl, 0.62 g, 1 mmol) and t-BuOK (2.24 g, 20 mmol) were added to 50 mL of dry 1 , 2-dimethoxyethane (DME), the reaction mixture was stirred overnight under nitrogen atmosphere, and the reaction was found to be complete by TLC.

[0031] The reaction mixture was carefully poured into 200 mL of ice water, stirred, and washed with 50 mL × 3 CH 2 Cl 2 After extraction, the extract phases were combined, 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 residue was purified by silica gel column chromatography to obtain compound IV-I, 1.76 g (yield 67%). ESI-MS, m / z=264(...

Embodiment 2

[0035] Example 2 Synthesis of Compound I-2

[0036]

[0037] Step 1. Synthesis of Compound IV-2

[0038] Compound II-2 (2.51g, 10mmol), Compound III (1.07g, 10mmol), Pd(OAc) 2 (0.22 g, 1 mmol), BINAP (2,2'-bisdiphenylphosphino-1,1'-binaphthyl, 0.62 g, 1 mmol) and t-BuOK (2.24 g, 20 mmol) were added to 50 mL of dry 1 , 2-dimethoxyethane (DME), the reaction mixture was stirred overnight under nitrogen atmosphere, and the reaction was found to be complete by TLC.

[0039] The reaction mixture was carefully poured into 200 mL of ice water, stirred, and washed with 50 mL × 3 CH 2 Cl 2 After extraction, the extract phases were combined, 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 residue was purified by silica gel column chromatography to obtain compound IV-2. ESI-MS, m / z=278([M+H] + ).

[004...

Embodiment 3-7

[0044] Referring to the methods of Examples 1 and 2, the following compounds were synthesized.

[0045]

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PUM

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Abstract

The present invention relates to the field of SSAO inhibitors. Specifically, the invention relates to an adamantane type SSAO inhibitor, a preparation method thereof and application of the adamantaneSSAO inhibitor in preparation of drugs for treating inflammatory diseases, immune diseases, tumors and the like. R is selected from alkyl with 1-10 carbon atoms and naphthenic base with 3-8 carbon atoms.

Description

technical field [0001] The present invention relates to the field of SSAO inhibitors. Specifically, the present invention relates to a class of novel SSAO inhibitors containing adamantane structure, which have a therapeutic effect on inhibiting SSAO, a preparation method thereof, and use in pharmacy. Background technique [0002] Semicarbazide-sensitive amine oxidase (SSAO) activity is regulated by Vascular Adhesinon Protein-1 (VAP-1) or copper amine oxidase (AmoneOxidase, Copper Containing 3, AOC3). ), which belong to the family of copper-containing amine oxidases (EC.1.4.3.6). Therefore, inhibitors of SSAO enzymes can also modulate the biological function of VAP-1 protein. Members of this family of enzymes are sensitive to inhibition by semicarbazides and use cupric ions and protein-derived hydroxydopa quinine (TPQ) cofactors for the oxidation of primary amines to aldehydes, hydrogen peroxide, and ammonia Deamination. [0003] Known substrates for human SSAO include en...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A61P29/00A61P37/02A61P35/00
CPCC07D401/04
Inventor 朱斌
Owner FOSHAN HANFANG CHINESE MEDICINE HOSPITAL CO LTD
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