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Carbamate compound, pharmaceutical composition and application of carbamate compound

A technology of carbamates and compounds, applied in the field of medicine, can solve problems such as poor activity of TRK inhibitors

Pending Publication Date: 2020-02-18
TETRANOV PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide carbamate compounds, to solve the problem of poor activity of TRK inhibitors in the prior art

Method used

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  • Carbamate compound, pharmaceutical composition and application of carbamate compound
  • Carbamate compound, pharmaceutical composition and application of carbamate compound
  • Carbamate compound, pharmaceutical composition and application of carbamate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The carbamate compound of present embodiment, its structural formula is as follows:

[0048]

[0049] The specific process route is as follows:

[0050]

[0051] Concrete preparation method comprises the following steps:

[0052] (1) Compound 1 (20.0g, 0.13mol, 1eq) was dissolved in dry 1,2-dichloroethane (EDC) (200ml), and AlCl was added under ice-cooling 3 (26.1g, 0.195mol, 1.5eq) and acetyl chloride (15.3g, 0.195mol, 1.5eq), then heated to 80°C for 12h to obtain a reaction solution; slowly added the reaction solution to ice water, added ethyl acetate for extraction, Washed with brine three times, combined the organic phases, dried over anhydrous sodium sulfate, spin-dried the organic phases, purified by column chromatography (petroleum ether: ethyl acetate = 4:1) to obtain compound 2 (5.6g white solid, yield 23.5%) ;

[0053] (2) Dissolve compound 2a (2.0g, 10.9mmol, 1eq) in ethanol (EtOH) (20mL), then add compound 2 (2.56g, 13.1mmol, 1.2eq) and triethylamin...

Embodiment 2

[0060] The carbamate compound of present embodiment, its structural formula is as follows:

[0061]

[0062] The nuclear magnetic resonance spectrum of this carbamate compound ( 1 H NMR, 400MHz) features: with CDCl 3 is the solvent, where the peaks are assigned as: δ8.08(s,1H),7.88(s,1H),7.04(m,1H),6.92(m,1H),6.74(m,1H),5.82(s, 1H), 5.41(s,1H), 4.13(m,1H), 7.70-3.94(m,3H), 0.70-2.47(m,10H); LCMS: M+1:444.

Embodiment 3

[0064] The carbamate compound of present embodiment, its structural formula is as follows:

[0065]

[0066] The nuclear magnetic resonance spectrum of this carbamate compound ( 1 H NMR, 400MHz) features: with CDCl 3 As a solvent, the peaks are assigned as: δ8.07(d, J=7.8Hz, 1H), 7.90(s, 1H), 7.04(m, 1H), 6.89(m, 1H), 6.66(m, 1H) ,5.90(s,1H),5.41(d,J=4.7Hz,1H),4.56(s,1H),4.01(d,J=10.7Hz,1H),3.92(m,1H),3.78–3.45( m,4H),2.20(m,1H),2.04(m,2H),1.87(m,1H),1.73(m,1H),0.66(m,1H),0.41(m,1H); LCMS: M +1:442.

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Abstract

The invention discloses a carbamate compound, a pharmaceutical composition and application of the carbamate compound and belongs to the technical field of pharmaceutical compound synthesis. The carbamate compound is a compound of a general formula I or general formula II shown in the description, or a pharmaceutically acceptable salt of the compound. The carbamate compound disclosed by the invention has remarkable effects in preventing and / or treating TRK (tropomyosin-related kinase) mediated diseases with pathological characteristics.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a carbamate compound, a pharmaceutical composition and the use of the carbamate compound in treating diseases mediated by TRK kinase. Background technique [0002] The tropomyosin receptor kinase (TRK) family belongs to the transmembrane receptor tyrosine kinases (RTKs) involved in the regulation of synapse growth and function maintenance in the mammalian nervous system, the occurrence and development of memory, and the protection of neurons from damage. TRK kinase is a kind of nerve growth factor receptor, and its family consists of highly homologous tropomyosin-related kinase A (Tropomyosin-related kinase A, TRKA), tropomyosin-related kinase B (Tropomyosin-related kinase B, TRKB), tropomyosin-related kinase C (Tropomyosin-related kinase C, TRKC), encoded by NTRK1, NTRK2 and NTRK3 genes, respectively. The complete TRK kinase includes three parts: the extracellular region, the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P35/00A61P35/02A61K31/519A61K31/5355
CPCC07D487/04A61P35/00A61P35/02
Inventor 吴豫生李钧梁阿朋牛成山陈其雨
Owner TETRANOV PHARMA CO LTD