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Lipoprotein lipase-activating compositions comprising benzene derivatives

Inactive Publication Date: 2011-03-17
OTSUKA PHARM FAB INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0090]Furthermore, the invention provides a method for preventing obesity for a patient requiring obesity prevention including administering to the patient at least one member of Compounds 1 in an amount effective for obesity prevention.

Problems solved by technology

Hyperlipidemia, obesity and the like are extremely dangerous causing diabetes and arteriosclerosis that may result in cardiac infarction, cerebral infarction, and the like.

Method used

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  • Lipoprotein lipase-activating compositions comprising benzene derivatives
  • Lipoprotein lipase-activating compositions comprising benzene derivatives
  • Lipoprotein lipase-activating compositions comprising benzene derivatives

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of 2-(4-benzyloxy-3-methoxyphenyl)imidazo[1,2-a]pyridine

(Step 1)

[0095]At a temperature of 0° C., 28.5 g (75.8 mmol) of phenyltrimethylammonium tribromide was added over 75 minutes to 120 ml of an anhydrous tetrahydrofuran solution of 12.0 g (72.2 mmol) of 4′-hydroxy-3′-methoxyacetophenone. This mixture was stirred for 2 hours at 0° C. and 30 minutes at room temperature. The reaction suspension thus obtained was concentrated under reduced pressure, mixed with 100 ml of ethyl acetate / hexane (1:1 v / v), and stirred for 30 minutes at 0° C. The crystalline phenyltrimethylammonium tribromide present in the suspension was removed by suction filtration and rinsed with 50 ml of ethyl acetate / hexane (1:1 v / v). The filtered solution was concentrated under reduced pressure, thereby giving 30 g of crude product.

[0096]At room temperature, 14.95 g (158.9 mmol) of 2-aminopyridine was added to 150 ml of an acetonitrile solution of the crude product (30 g) obtained above. The mixture was s...

example 12

Preparation of 3-(4-benzyloxy-3-methoxyphenyl)imidazo[1,2-a]pyridine

(Step 1)

[0100]To a solution of 4.23 g (16.9 mmol) of 2-methoxy-4-(4,4,5,5)-tetramethyl-1,3,2-dioxaborane-2-yl phenol in 200 ml dry DMF were added 5.0 g (25.4 mmol) of 3-bromoimidazo[1,2-a]pyridine, 0.39 g (0.34 mmol) of tetrakis(triphenylphosphinato)palladium [0] (Pd(PPh3)4 wherein Ph is phenyl), and 42.25 ml of 2M aqueous potassium phosphate solution. The mixture was stirred for 20 hours at 80° C. After reaction, DMF was distilled off under reduced pressure, and the residue was purified using a silica gel column (eluant: methanol / methylene chloride=2 / 98 to 4 / 96).

[0101]The crystals thus obtained were recrystallized using methanol-hexane, thereby producing 2.82 g of 3-(4-hydroxy-3-methoxyphenyl)imidazo[1,2-a]pyridine (yield: 70%). This compound will be referred to as “Example Compound 131”.

(Step 2)

[0102]To 1 ml of DMF were added 24 mg (0.1 mmol) of the compound obtained in Step 1 (Example Compound 131), 65 mg (0.2 mm...

example 23

Preparation of 6-[4-(4-chlorobenzyloxy)-3-methoxyphenyl]imidazo[2,1-b]thiazole

(Step 1)

[0104]To 600 ml of an anhydrous THF solution of 100 g 4′-hydroxy-3′-methoxyacetophenone was added 237.5 g phenyltrimethylammonium tribromide over 3 hours at a temperature of 0° C., followed by stirring at 0° C. for 6 hours and at room temperature for 13 hours. The reaction solution thus obtained was concentrated under reduced pressure, mixed with 500 ml of ethyl acetate, and stirred at 0° C. for 1 hour. The precipitated crystals were removed by suction filtration, and the filtered solution was concentrated under reduced pressure, thereby yielding 265 g of oily matter.

[0105]This oily matter was dissolved in 400 ml of anhydrous DMF, and the solution thus obtained was added to 60 g of 2-aminothiazole followed by stirring at room temperature for 30 minutes and 40° C. for 3.5 hours. The reaction mixture thus prepared was diluted with 400 ml of ethyl acetate and left for 15 hours at room temperature. The...

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PUM

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Abstract

The present invention provides pharmaceutical compositions containing benzene compound(s) represented by General Formula (1) below and, particularly, LPL-activating compositions for use in hyperlipidemia therapeutic and preventive agents, anti-obesity agents, and the like:wherein R1, R2, R3 and R4 are as defined in the specification.

Description

TECHNICAL FIELD[0001]The present invention relates to compositions for activating lipoprotein lipase (hereinafter referred to as “LPL”) and benzene compounds. The invention is further directed to the use of compounds activating LPL for preparing LPL-activating compositions, and a method for activating LPL using such compounds.BACKGROUND OF THE INVENTION[0002]Contemporary society is called a society of gluttony, and the number of people diagnosed with hyperlipidemia, obesity, etc., has been sharply rising. Hyperlipidemia, obesity and the like are extremely dangerous causing diabetes and arteriosclerosis that may result in cardiac infarction, cerebral infarction, and the like.[0003]Accordingly, to prevent or treat hyperlipidemia, obesity, etc., a variety of research has been conducted on pharmaceuticals and chemotherapy for ameliorating pathological conditions of these diseases, for example, chemotherapy to activate LPL (lipoprotein lipase) and chemotherapeutic agents therefor. LPL ac...

Claims

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Application Information

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IPC IPC(8): A61K31/519A61K31/437C07D471/04A61K31/429C07D513/04C07D487/04A61K31/4184C07D235/18A61K31/4164C07D233/64A61K31/428C07D277/66A61P3/04A61P3/06
CPCA61K31/4164C07D233/56A61K31/4188A61K31/428A61K31/4745A61K31/519C07D233/58C07D235/18C07D277/66C07D471/04C07D487/04C07D513/04A61K31/429A61K31/437A61K31/4184A61P3/04A61P3/06A61P9/10A61P43/00
Inventor NEAGU, IRINAOHLMEYER, MICHAELPARADKAR, VIDYADHAR M.SAIONZ, KURT W.IWATA, KOUSHIOKAMURA, TAKASHISHIBUTANI, TADAO
Owner OTSUKA PHARM FAB INC
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