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Quinolizinones compound and preparation method and application thereof

The technology of a compound, quinazinone, applied in the field of medicine, can solve the problem of unknown anti-HBV activity

Active Publication Date: 2017-07-07
河南春风医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, in this patent, it is not disclosed that V or Y is O, S, SO 2 and NR specific compounds, their anti-HBV activity is also unknown, and V or Y is O, S, SO 2 Or the specific compound of NR is difficult to be synthesized by the preparation method disclosed in this patent

Method used

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  • Quinolizinones compound and preparation method and application thereof
  • Quinolizinones compound and preparation method and application thereof
  • Quinolizinones compound and preparation method and application thereof

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Embodiment 1c

[0065] Example 1cis-10-methoxy-11-(3-methoxypropoxy)-3,3-dimethyl-7-oxo-3,3a,7,12b-tetrahydro-2H-furan And[3,2-c]pyrido[2,1-a]isoquinazine-6-carboxylic acid

[0066] The synthetic route is as follows:

[0067]

[0068] Step 1: Preparation of 6-(2-Hydroxy-1,1-dimethyl-ethyl)-10-methoxy-9-(3-methoxypropoxy)-2-oxo-6,7 -Ethyl dihydrobenzo[a]quinazine-3-carboxylate

[0069] 6-(2-Benzyloxy-1,1-dimethyl-ethyl)-10-methoxy-9-(3-methoxypropoxy)-2-oxo-6,7- Ethyl dihydrobenzo[a]quinazine-3-carboxylate (1.65g, 3mmol, preparation reference patent document US20160122344A1), and Pd / C (10%) (0.5g) were slowly added in ethanol (200mL), in hydrogen Pressurized under the atmosphere and mechanically stirred to obtain crude 6-(2-hydroxy-1,1-dimethyl-ethyl)-10-methoxy-9-(3-methoxypropoxy)-2 -Ethyl oxo-6,7-dihydrobenzo[a]quinazine-3-carboxylate (1.10 g, yield about 79.7%) was directly used in the next step without purification.

[0070] 1 H NMR (400MHz, CDCl 3 )δ:8.43(s,1H),7.12(s,1H),6.89(...

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Abstract

The invention discloses a quinolizinones compound which comprises an optical isomer, a raceme and a cis-trans-isomer and a random combination or pharmaceutical salt thereof. A structure of the quinolizinones compound is as shown in a formula I: (with reference to the specification), wherein one of V and Y is O, and the other one of V and Y is CR8R9; R8 and R9 respectively independently are hydrogen or C1-6 alkyl. The invention further discloses a preparation method and application of the compound in the formula I. The compound in the formula I can obviously reduce a HBsAg (Hepatitis B surface antigen) level in vivo and meanwhile, inhibit replication of a HBV (Hepatitis B Virus), wherein when V or Y is O, solubility of the compound is obviously improved, the compound has excellent medicinal attributes and meanwhile, is also low in toxicity, pharmacokinetics and pharmacodynamics functions are improved, efficiency of combining with the HBV can be greatly improved, and a clearance ratio of the HBV in vivo can also be further improved.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a quinozinone compound used for treating and preventing hepatitis B virus infection and its preparation method and application. Background technique [0002] As a partially double-stranded DNA virus, hepatitis B virus (HBV) needs to go through a step of reverse transcription from RNA intermediate to DNA for its replication. The HBV genome can encode a variety of antigens including surface antigen (HBsAg) and DNA polymerase required in the process of DNA replication. [0003] During the pathogenic process of HBV, if the host immune system is continuously exposed to HBsAg and other antigens, it can lead to a large loss of HBV-specific T cells or progressive functional damage (Kondo, et al. Journal of Immunology. 1993, 150: 4659 -4671; Kondo, et al.Journal of Medical Virology.2004,74:425-433; Fisicaro, et al.Gastroenterology.2010,138:93-682.), and can also directly inhibit the fun...

Claims

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Application Information

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IPC IPC(8): C07D491/147A61P1/16A61P31/20
CPCC07B2200/07C07D491/147
Inventor 李定芳程森祥郭应臣
Owner 河南春风医药科技有限公司
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