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Sulfonamide-arylamide compound, and medicinal application of same to treatment of hepatitis B

A compound and aryl technology, applied in the field of chemical medicine, can solve the problems of poor curative effect, poor bioavailability, mutagenicity, etc.

Inactive Publication Date: 2018-07-06
SHANGHAI LONGWOOD PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, problems such as toxicity, mutagenicity, lack of selectivity, poor efficacy, poor bioavailability, and difficulty in synthesis are encountered in these direct HBV antiviral drugs

Method used

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  • Sulfonamide-arylamide compound, and medicinal application of same to treatment of hepatitis B
  • Sulfonamide-arylamide compound, and medicinal application of same to treatment of hepatitis B
  • Sulfonamide-arylamide compound, and medicinal application of same to treatment of hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0128] The compound of formula V-1 can be prepared from the compound of formula I-1 as a starting material. Concrete preparation method can comprise the following steps:

[0129]

[0130] In each formula, the definitions of R1, R2, R3 and Z are the same as above.

[0131] The compound of formula VI-1 can be prepared from the compound of formula I-1 as a starting material. Concrete preparation method can comprise the following steps:

[0132]

[0133] In each formula, the definitions of R1, R2, R3 and Z are the same as above.

[0134] The compound of formula VII-3 can be prepared from the compound of formula I-1 as a starting material. Concrete preparation method can comprise the following steps:

[0135]

[0136] In each formula, the definitions of R1, R2 and R3 are the same as above.

[0137] The compound of formula VIII-3 can be prepared from the compound of formula I-3 as a starting material. Concrete preparation method can comprise the following steps:

[0...

Embodiment 1

[0161] Embodiment 1: the synthesis of compound 8

[0162]

[0163] Step 1: Synthesis of compound 2

[0164]

[0165] Dissolve substrate 1 (1.0g) in acetic anhydride (2mL), lower the system temperature to 0°C, then add fuming nitric acid (0.5mL) to the reaction system, react at 0°C for 3h, then add iodomethane (668mg) The reaction system was reacted at room temperature for 3h. TLC detected that the reaction of raw materials was complete, water (20mL) was added to the reaction system, ethyl acetate (3*30mL) was extracted, the organic phase was dried, spin-dried, and the crude product was column chromatographed (n-heptane:ethyl acetate=1:5), Product 2 (400 mg) was obtained. MS (M+1=219).

[0166] Step 2: Synthesis of Compound 3

[0167]

[0168] Substrate 2 (0.4g) was dissolved in acetic acid (5mL), iron powder (1.8g) was added to the reaction system at room temperature, and reacted at room temperature for 3 hours. TLC detected that the raw materials were completely ...

Embodiment 2

[0180] The synthesis of embodiment 2 compound 8a

[0181]

[0182] According to step 5, it is only necessary to replace compound 7 with compound 7a, and other conditions remain unchanged, and the target product 8a is obtained by high performance liquid chromatography. MS (M+1=461).

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Abstract

The invention relates to a sulfonamide-arylamide compound, and medicinal application of the same to treatment of hepatitis B. Specifically, the invention discloses a compound having a structure as shown in a formula (A) and applicable as a HBV replication inhibitor, or a stereoisomer, cis-trans isomer or tautomer thereof, or a pharmaceutically acceptable salt, hydrate or solvate thereof. Each group in the formula (A) is as defined in the specification. The invention further relates to a pharmaceutical composition comprising the above compound and application of the pharmaceutical composition to the treatment of hepatitis B.

Description

technical field [0001] The invention belongs to the field of chemistry and medicine, in particular, the invention relates to a sulfonamide-arylamide compound and its medicinal application for treating hepatitis B. Background technique [0002] Hepatitis B virus (HBV) is an enveloped, partially double-stranded DNA (dsDNA), virus of the hepadnaviridae DNA family (Hepadnaviridae). Its genome contains 4 overlapping reading frames: prenuclear / nuclear gene, polymerase gene, UM and S genes (which encode three envelope proteins), and X gene. Before infection, the partially double-stranded DNA genome is converted in the host cell nucleus (open circular DNA; rcDNA) to covalently closed circular DNA (cccDNA) and the viral mRNA is transcribed. Once encapsidated, the pregenomic RNA (pgRNA), which also encodes core protein and Pol, serves as a template for reverse transcription, which regenerates the partial dsDNA genome (rcDNA) in the nucleocapsid. [0003] HBV has caused epidemics in ...

Claims

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Application Information

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IPC IPC(8): C07D207/34C07D231/40C07D231/16A61K31/40A61K31/415A61P31/20A61P1/16A61P29/00A61P35/00
CPCC07D207/34C07D231/16C07D231/40C07D231/14C07D401/12C07D403/12C07D405/12A61K31/40A61K31/415A61P1/16A61P29/00A61P31/20A61P35/00
Inventor 王喆王晓光卢涔宾范国钦
Owner SHANGHAI LONGWOOD PHARMA
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