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Carboxylic compound and medicine comprising the same

A compound and medical technology, applied in the field of carboxylic acid compounds, can solve the problems of hypoglycemia and secondary ineffectiveness of sulfonylureas, induced lactic acid, poisoning, etc.

Inactive Publication Date: 2008-02-13
KOWA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Insulin and sulfonylureas are often used in the drug treatment of diabetes, but as a side effect, hypoglycemia and sulfonylureas are secondary ineffective due to liver fatigue
Biguanides improve insulin sensitivity, barely correct hyperglycemia, but induce lactic acidosis
The thiazolidine series diabetes treatment drugs developed in recent years are said to have the effect of improving peripheral insulin resistance (expert opinion on drug research, 9, pp1347-1361, 2000), and will not cause hypoglycemia, and can control blood sugar well. But as a side effect reported severe damage to the liver etc.

Method used

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  • Carboxylic compound and medicine comprising the same
  • Carboxylic compound and medicine comprising the same
  • Carboxylic compound and medicine comprising the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] (1) Synthesis of 10-bromo-1-(4-chlorophenyl)-5-decanol

[0083] Add 5 mL of anhydrous THF to magnesium (591 mg, 24.31 mmol), stir in an argon atmosphere at room temperature, add iodine (10 mg), and stir for 2 hours until the dark brown color almost disappears. 10 mL of an anhydrous THF solution of 4-(4-bromobutyl)chlorobenzene (6.02 g, 24.32 mmol) was added dropwise to the reaction solution for 10 minutes. After the dropwise addition, the mixture was continuously stirred at room temperature for 3 hours to prepare the Grignard reagent.

[0084] 6-Bromohexanal (4.79 g, 49.58 mmol) was dissolved in 10 mL of anhydrous THF with stirring under ice cooling. The prepared Grignard reagent was added dropwise to this solution for 10 minutes. The reaction solution was returned to room temperature, and stirring was continued for 18 hours.

[0085] After the reaction, the reaction solution was water-cooled, and 20 mL of purified water and 20 mL of saturated saline were slowly adde...

Embodiment 2

[0100] (1) Synthesis of 10-bromo-1-(4-chlorophenyl)-3-decanol

[0101] Add 20 mL of anhydrous THF to magnesium (1.07 g, 44.0 mmol), stir in an argon atmosphere at room temperature, add iodine (10 mg), and stir for 2 hours until the dark brown color almost disappears. 20 mL of anhydrous THF solution of 4-(2-bromoethyl)chlorobenzene (9.62 g, 43.8 mmol) was slowly added to the reaction liquid, and stirring was continued for 3 hours to prepare a Grignard reagent.

[0102] 8-Bromo-1-octanal (10.27 g, 49.6 mmol) was dissolved in 30 mL of anhydrous THF under an argon atmosphere with stirring under ice cooling. The prepared Grignard reagent was added dropwise to this solution for 15 minutes. The reaction solution was returned to room temperature, and stirring was continued for 16 hours.

[0103] After the reaction, the reaction solution was water-cooled, and 20 mL of purified water and 20 mL of saturated saline were slowly added, and stirred for 20 minutes. The mixture was extracte...

Embodiment 3

[0120] (1) Synthesis of 2,2-dichloro-12-(4-chlorophenyl) methyl laurate

[0121] 2,2-Dichloro-12-(4-chlorophenyl)lauric acid (47.3g, 124.5mmol) was dissolved in 1000mL of methanol, sulfuric acid (6.10g, 62.19mmol) was added, and heated under reflux for 24 hours with stirring.

[0122] After cooling the reaction solution, it was concentrated under reduced pressure, 500 mL of chloroform and 500 mL of water were added, and the organic layer was separated. After the aqueous layer was extracted with chloroform (100m×3), the organic layers were combined, washed with water (200mL), dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the crude target compound (47.35g, yield 96.6%). Yellow oil.

[0123] 1 H-NMR (CDCl 3 )δ: 1.22-1.40 (12H, m), 1.51-1.62 (4H, m), 2.41 (2H, m), 2.56 (2H, t, J=8Hz), 3.89 (3H, s), 7.10 (2H, d, J=8Hz), 7.23 (2H, d, J=8Hz).

[0124] (2) Synthesis of 12-bromo-2,2-dichloro-12-(4-chlorophenyl)methyl laurat...

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Abstract

Provided are a compound represented by the following general formula (1): [wherein m is an integer of 0 to 4; n is an integer of 5 to 9; and W represents -CH(OR)- (R represents hydrogen or a hydroxy-protecting group) or -C(=O)-], a salt of the compound, or an ester of the compound. The compound, salt, or ester is effective in blood sugar depression, plasma insulin reduction, and triglyceride reduction and is useful for the prevention of and / or treatments for diabetes, complications of diabetes, hyperlipemia, etc.

Description

technical field [0001] The present invention relates to a drug that exhibits strong blood sugar lowering effect, plasma insulin lowering effect and glyceride lowering effect, and is not accompanied by weight gain and obesity, and can prevent and / or treat diabetes, diabetic complications, hyperlipidemia, arterial A carboxylic acid compound for diseases such as sclerosis, and a medicine containing the carboxylic acid compound. Background technique [0002] Diabetes mellitus is a metabolic disease caused by various causes, and is classified into type 1 with insufficient insulin secretion or type 2 with decreased insulin sensitivity in peripheral tissues. Type 2 diabetes, against the background of environmental factors such as obesity and overeating, has increased dramatically in recent years, and the incidence of diabetes in the world is said to be 5%. [0003] Insulin and sulfonylureas are often used in the drug treatment of diabetes, but as a side effect, hypoglycemia and su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/56C07C59/88C07C69/732C07C69/738A61K31/20A61P3/06A61P3/10A61P9/00A61P29/00A61P9/10
Inventor 井上敬介当间勉北村崇博山崎行由石川哲也
Owner KOWA CO LTD
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