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Novel isoquinoline compound and medical application thereof
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A technology of compounds and medicinal salts, which is applied in the field of new isoquinoline compounds and their medical applications, can solve the problem of not being able to reduce hepatitis B surface antigen
Inactive Publication Date: 2018-11-02
GINKGO PHARMA
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Problems solved by technology
At present, nucleoside drugs cannot reduce HBsAg, and it is necessary to design a drug with a new mechanism of action, which can be used in combination with powerful nucleoside drugs, and at the same time effectively remove HBsAg and viral DNA in the blood, activate and restore its own Immune function, and thus an eventual possible cure for hepatitis B
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Embodiment 1
[0097] Example 1: 6-isopropyl-10-methoxy-9-(3-methoxypropoxy)-N-(cyclopropylsulfonyl)-2-oxo-6,7-dihydro -2H-pyrido[2,1-a]isoquinoline-3-carboxamide (10)
[0098]
[0099] Step 1: Synthesis of 4-bromo-1-methoxy-2-(3-methoxypropoxy)benzene (2)
[0100]
[0101] 1-Bromo-3-methoxypropane (49.8g, 325.4mmol) was added dropwise to a solution of 5-bromo-2-methoxyphenol (22.0g, 108.4mmol) and anhydrouspotassiumcarbonate (45g, 325.6mmol) in DMF (30mL) suspension, stirred overnight at room temperature, poured into water, extracted three times with ethyl acetate, combined organic phase, washed with water and saturated brine, dried over anhydroussodiumsulfate, concentrated to obtain a yellow oily liquid, 26g, 87.2% . ESI-MS: [M+H]+: 275.2.
[0104] In the reaction flask of THF (180mL), add compound 2 (20.6g, 75.1mmol), Pd2(dba)3(1.38g, 1.5mmol), xantphos (1.74g, 3.0mmol), sodium tert...
Embodiment 2
[0126] Example 2: 6-isopropyl-10-methoxy-9-(3-methoxypropoxy)-3-(1H-tetrazol-5-yl)-6,7-dihydro-2H -pyrido[2,1-a]isoquinolin-2-one (12)
[0127]
[0128] Reaction process 2:
[0129]
[0130] Step 1: 6-Isopropyl-10-methoxy-9-(3-methoxypropoxy)-2-oxo-6,7-dihydro-2H-pyrido[2,1-a ] Synthesis of isoquinoline-3-carboxamide (11)
[0131]
[0132]Compound 9 (1g, 2.49mmol) was added to a reaction flask of thionylchloride (10mL), dripped into 1d DMF, refluxed for 3 hours, concentrated, and the residual thionylchloride was removed with toluene, then diluted with THF (10mL), Cool to 0°C, add ammonia water (5 mL) dropwise, raise to room temperature, stir overnight, evaporate THF under reduced pressure, filter the obtained solid, wash with ice water to obtain compound 11, 0.86 g, 87%. Proceed directly to the next reaction. ESI-MS: [M+H]+: 401.2.
[0133] Step 2: 6-Isopropyl-10-methoxy-9-(3-methoxypropoxy)-2-oxo-6,7-dihydro-2H-pyrido[2,1-a ] Synthesis of isoquinoline-3-carbo...
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Abstract
The invention relates to an isoquinoline compound shown as a formula (A) or a stereoisomer, a pharmaceutically acceptable salt, a hydrate, a solvate or a crystal thereof, a medicinal composition thereof and application thereof as antiviral medicines. The isoquinoline compound inhibits hepatitis B DNA activity and hepatitis B surface antigen activity at the same time. The invention particularly relates to application thereof to preparation of medicines for treating and / or preventing hepatitis B, hepatitis B viruses (HBV) thereof and other viral infectious diseases, in particular to treatment and / or prevention of the hepatitis B and the hepatitis B viruses as HBV Surface antigen inhibitor medicines and HBV DNA production inhibitor medicines.
Description
technical field [0001] The invention belongs to the field of medicinal chemistry antiviral, in particular to a class of novel isoquinoline compounds or their stereoisomers and the use of pharmaceutical compositions containing isoquinoline compounds or their stereoisomers as antiviral drugs, in particular It is used as a medicine for treating and / or preventing hepatitis B virus infection as a hepatitis B surface antigen inhibitor (HBV Surface antigen inhibitors) and a hepatitis B DNA inhibitor (HBVDNA production inhibitors), especially referring to such compounds and nucleoside drugs and Use of other medicines as a medicinal composition for curing hepatitis B. Background technique [0002] There are about 350 million chronic hepatitis B infections in the world, and 780,000 people died of hepatitis B in 2011. Among them, hepatitis B patients in China account for one-third of the global total. China currently spends more than 100 million people on hepatitis B treatment each yea...
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