Uses of substituted tetrahydrochysene isoquinoline derivant

A use and compound technology, applied in the field of preparing antidiabetic drugs, can solve the problems of poor therapeutic effect on cardiovascular complications, hypoglycemic side effects, weak insulin sensitization effect, etc.

Inactive Publication Date: 2009-05-13
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the existing hypoglycemic drugs can promote insulin secretion and lower blood sugar, most of them have disadvantages such as hypog

Method used

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  • Uses of substituted tetrahydrochysene isoquinoline derivant
  • Uses of substituted tetrahydrochysene isoquinoline derivant
  • Uses of substituted tetrahydrochysene isoquinoline derivant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047]Preparation of (s)-2-acetyl-3-carboxy-1,2,3,4-tetrahydroisoquinoline (IX):

[0048] (s)-3-carboxy-1,2,3,4-tetrahydroisoquinoline 10g (0.047mol) mixed with 100ml acetone, 40ml sodium hydroxide aqueous solution (2mol / L), at room temperature, drop 8.01ml at the same time Acetyl chloride (0.094mol) and 2mol / L sodium hydroxide aqueous solution, after dropwise addition, keep the pH value of the reaction solution greater than 9, and continue to stir for 2 hours. Evaporate most of the solvent, acidify the remaining liquid with 3mol / L dilute hydrochloric acid, cool, and precipitate a white solid, filter, wash with water, and dry. The crude product weighs 9.1g (88.4%), and its melting point is 170-171°C (literature 171-173°C) .

Embodiment 2

[0050] Preparation of (s)-2-acetyl-3-formyl-1,2,3,4-tetrahydroisoquinoline (VIII):

[0051] At 0° C., 4.05 ml (0.057 mol) of thionyl chloride was added dropwise to 30 ml of anhydrous methanol. After the dropwise addition was completed, the mixture was stirred at room temperature for 2 hours. Add 5.0 g (0.023 mol) of (s)-2-acetyl-3-carboxy-1,2,3,4-tetrahydroisoquinoline to the above reaction solution, heat to reflux for 3 hours, and evaporate the solvent. Add ethyl acetate to dissolve, wash with saturated sodium bicarbonate and saturated brine respectively until neutral, dry over anhydrous sodium sulfate, evaporate the solvent, and dry to obtain a light yellow solid, the weight of the crude product is 5.04 g (94.1%).

Embodiment 3

[0053] Preparation of (s)-2-acetyl-3-carboxymethyl-7-chlorosulfonyl-1,2,3,4-tetrahydroisoquinoline (VII):

[0054] At -5°C, add 5.0 g (0.021 mol) of (s)-2-acetyl-3-methylcarboxylate-1,2,3,4-tetrahydroisoquinoline to 15 ml of chlorosulfonic acid in batches After the addition was complete, stir overnight at room temperature. The reaction solution was poured into a large amount of crushed ice, stirred, and filtered to obtain 12 g (wet weight) of a white solid, which was directly used in the next reaction.

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PUM

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Abstract

The invention relates to a general formula (I) compound and application of salt thereof to preparation of drugs, in particular to application of the salt thereof to preparation of antidiabetic drugs. Pharmacological experiments show that the compound has good antidiabetic effect.

Description

technical field [0001] The present invention relates to tetrahydroisoquinoline derivatives substituted by sulfonamides, and their use in the preparation of medicines, in particular to the preparation of antidiabetic drugs. Background technique [0002] Diabetes, especially type 2 diabetes, is the third chronic non-communicable disease that seriously threatens human health after tumors and cardiovascular diseases. Currently, there are about 200 million diabetics in the world, which is expected to increase to 300 million by 2025. In 2007, China had 40 million diabetic patients, second only to India with 40.9 million diabetic patients, ranking second in the world. It is estimated that by 2025, the number of diabetic patients in my country will exceed 60 million, of which type 2 diabetes accounts for about the total number of diabetic patients More than 90% of. [0003] Diabetes mellitus is an absolute or relative lack of insulin, which causes glucose metabolism disorder, secon...

Claims

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Application Information

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IPC IPC(8): C07D401/06A61K31/4725A61P3/10
Inventor 黄文龙张惠斌沙向阳周映红周金培钱海张亚安
Owner CHINA PHARM UNIV
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