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Isoquinoline derivatives and their preparation process and application

A derivative, isoquinoline technology, applied in the field of isoquinoline derivatives, can solve the problems of safety concerns, inability to effectively reduce LDL-C levels, and inability of patients to tolerate statin drugs well

Inactive Publication Date: 2006-09-06
周桂华 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because some patients do not tolerate statins well
More importantly, many patients cannot effectively lower LDL-C levels with statin alone
In addition, statins have clinically induced muscle fiber melting and liver damage, raising serious concerns about the drug's safety.

Method used

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  • Isoquinoline derivatives and their preparation process and application
  • Isoquinoline derivatives and their preparation process and application
  • Isoquinoline derivatives and their preparation process and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Take the roots of the three needles and crush them, soak them in 0.5-1% sulfuric acid for a day and night, pour out or filter the next day, and add salt to the extract (generally 8-10 times the amount can be collected, and the second half will be used for the next batch) and add salt for 10 % hydrochloric acid to neutralize to acidic, stand overnight, filter the precipitated 9,10-dimethoxy-[1,3]dioxo[4,5-g]isoquinoline[3,2-a]isoquinoline - Crude 7-ylide hydrochloride.

[0058] When refining, dissolve the crude product in heated water, adjust to pH 8.5-9.8 with lime water, cool, filter out impurities, add concentrated hydrochloric acid to the filtrate to pH 2, cool to below 30°C, filter the precipitate, wash with water until neutral, and then Heat to dissolve with 5-10 times the amount of 70% alcohol, filter, cool, and filter the precipitated 9,10-dimethoxy-[1,3]dioxo[4,5-g]isoquinoline[3, 2-a] Isoquinoline-7-ylide hydrochloride boutique.

[0059]

[0060] Structura...

Embodiment 2

[0062] 9,10-Dimethoxy-[1,3]dioxo[4,5-g]isoquinoline[3,2-a]isoquinoline-7-ylide hydrochloride methylene aldehyde ketol Hydrolysis

[0063]

[0064] 37.6g (0.1mol) 9,10-dimethoxy-[1,3]dioxo[4,5-g]isoquinoline[3,2-a]isoquinoline-7-ylide hydrochloride , 2eq PCl 5 , in 500ml CH 2 Cl 2 Medium reflux reaction for 2hrs, rotary evaporation to remove solvent CH 2 Cl 2 , 200ml of water was added, and the reaction was refluxed for 3hrs to complete the reaction. Crystals were precipitated after cooling, and the product was obtained by suction filtration. Dry to obtain product 21.5g, yield 60%.

Embodiment 3

[0066] 9,10-Dimethoxy-[1,3]dioxo[4,5-g]isoquinoline[3,2-a]isoquinoline-7-ylide hydrochloride methylene aldehyde ketol modification of the hydrolyzate

[0067]

[0068] 3.6g(II), 5eq Et 3 N, 100ml CH 2 Cl 2 . At 0-5°C, 2.4eq acetyl chloride was added dropwise with stirring. After the addition was complete, the reaction was stirred at room temperature for 6 hrs. The solvent was removed by rotary evaporation, and 4.2 g of the crude product was recrystallized from ethanol as white crystals. Yield 89%.

[0069] Similarly, compound II reacts with halogenated alkanes or acid anhydrides, acid chlorides or sulfonic anhydrides, and sulfonyl chlorides to obtain their corresponding ethers or esters.

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Abstract

The invention discloses an isoquinoline derivant. The said derivant, with 9,10-dimethoxy -[1,3] dioxide [4,5-g] isoquinoline [3,2-a] isoquinoline -7-ylidehydrochlorate (I) as its representative, reduces plasma cholesterol level by massively absorbing low density lipoprotein cholesterol and changing them to bile acid in liver. The 9,10-dimethoxy -[1,3] dioxide [4,5-g] isoquinoline [3,2-a] isoquinoline-7-ylidehydrochlorate is a new cholesterol lowering compound which is different in cholesterol lowering mechanism from statins. The 9,10-dimethoxy -[1,3] dioxide [4,5-g] isoquinoline [3,2-a] isoquinoline -7-ylidehydrochlorate and other isoquinoline derivants have an extremely low side toxiceffect, so they are safe natural cholesterol lowering compounds.

Description

technical field [0001] The invention relates to a brand-new compound for lowering plasma cholesterol and regulating blood fat. More specifically relates to a class of 9,10-dimethoxy-[1,3]dioxo[4,5-g]isoquinoline[3,2-a]isoquinoline-7-ylide hydrochloride as Representative uses of isoquinoline derivatives. Background technique [0002] Atherosclerotic cardiovascular and cerebrovascular diseases (such as coronary heart disease, stroke) are the main killers of fatal diseases in China and Western countries. The main cause is high serum total cholesterol (Gordon et al.1981; Stamler et al.1986; Pooling Project Research Group 1978; Anderson et al.1987). Epidemiological survey revealed that for every 1% increase in serum total cholesterol, the risk factors for coronary heart disease increased by 2% (NCEPR 1991). Clinical studies have found that lowering serum cholesterol levels can reduce the incidence of coronary heart disease and retard the development of atherosclerosis (LPCP 19...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/00A61K31/4745A61P9/10A61P3/06A23K1/16A23K20/132
Inventor 王文广
Owner 周桂华
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