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1,2,3,5-tetrahydro-cyclopental[c]quinolin-4-one derivatives as RXR agonists for the treatment of dyslipidemia, hypercholesterolemia and diabetes

A solvate and compound technology, applied in the field of new compounds, can solve problems such as lack of full utilization of glucose, harmful accumulation of glucose, etc.

Inactive Publication Date: 2008-12-03
JANSSEN PHARMA NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the transport of glucose from the blood into muscle and fat tissue is dependent on insulin, people with diabetes lack the ability to fully utilize glucose, which leads to the harmful accumulation of glucose in the blood, or hyperglycemia

Method used

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  • 1,2,3,5-tetrahydro-cyclopental[c]quinolin-4-one derivatives as RXR agonists for the treatment of dyslipidemia, hypercholesterolemia and diabetes
  • 1,2,3,5-tetrahydro-cyclopental[c]quinolin-4-one derivatives as RXR agonists for the treatment of dyslipidemia, hypercholesterolemia and diabetes
  • 1,2,3,5-tetrahydro-cyclopental[c]quinolin-4-one derivatives as RXR agonists for the treatment of dyslipidemia, hypercholesterolemia and diabetes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0251]

[0252] 3-[3-(5-Ethyl-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenteno[c]quinolin-8-yl)-4-tri Fluoromethoxy-phenyl]-acrylic acid (compound 1)

[0253] A. 8-Bromo-1,2,3,5-tetrahydro-cyclopenta[c]quinolin-4-one (compound 1A)

[0254] The title compound was prepared from 4-bromophenylisocyanate according to Jaroch et al, Bioorg. Med. Chem. Lett. 2002, 12, 2561. MS (electrospray): C 12 h 10Calculated mass for BrNO, 262.99; m / z found 264, [M+H] + .

[0255] B. 8-Bromo-5-ethyl-1,2,3,5-tetrahydro-cyclopenta[c]quinolin-4-one (compound 1B)

[0256] A solution of Compound 1A (2.3 g, 8.7 mmol) was dissolved in 35 mL of DMSO and added to a pre-stirred 2.0 M solution of potassium hydroxide (730 mg, 13.1 mmol) in DMSO. Then, ethyl iodide (01.45 mL, 17.4 mmol) was added and the reaction was stirred at room temperature overnight. The reaction was quenched with 100 mL of water and extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate,...

Embodiment 2

[0264]

[0265] 3-[3-(5-Ethyl-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenteno[c]quinolin-7-yl)-4-tri Fluoromethoxy-phenyl]-acrylic acid (compound 2)

[0266] Using a procedure similar to that described for the preparation of compound 1, except using 3-bromophenylisocyanate in Step 1A, the title compound was prepared. MS (electrospray): C 24 h 20 f 3 NO 4 The calculated value of , 443.1; the measured value of m / z 444.1, [M+H] + .

Embodiment 3

[0268]

[0269] 3-[3-(5-Ethyl-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenteno[c]quinolin-8-yl)-4-tri Fluoromethoxy-phenyl]-propionic acid (Compound 3)

[0270] Compound 1 (25mg, 0.056mmol) was dissolved in 5ml EtOAc and treated with a catalytic amount (5mg) of 10% Pd / C and H 2 The balloon was hydrogenated for 4 hours. The Pd / C was then filtered off and the solvent was evaporated to give the product as a colorless oil. Evaporation from hexane or ether afforded 23 mg of compound 3 (100%) as a white viscous foam. MS (electrospray): C 24 h 22 f 3 NO 4 Calculated mass, 445.2; found m / z 446.2, [M+H] + .

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Abstract

The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating RXR mediated disorders. More particularly, the compounds of the present invention are RXR agonists useful for treating RXR mediated disorders.

Description

field of invention [0001] The present invention relates to some novel compounds, and relates to methods for preparing compounds, compositions, intermediates and derivatives thereof, and treating cancer and metabolic diseases. More particularly, the compound of the present invention is a retinoid X receptor (RXR) agonist, which can be used for the treatment, improvement, prevention and / or suppression of cancer and metabolic diseases like diabetes, dyslipidemia and hypercholesterolemia. attack. Background of the invention [0002] Diabetes is a chronic disease that affects the metabolism of carbohydrates, fats and proteins in animals. [0003] Type I diabetes, which constitutes approximately 10% of all diabetes cases, was formerly known as insulin-dependent diabetes mellitus ("IDDM") or juvenile diabetes. This disease is characterized by a progressive loss of pancreatic beta insulin secretion. This is also characterized by non-idiopathic or "secondary" diabetes arising from...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/22A61K31/473A61P3/10A61P3/06A61P9/10A61P29/00
CPCC07D215/233A61P1/04A61P3/02A61P3/04A61P3/06A61P3/10A61P5/50A61P7/02A61P9/00A61P9/10A61P9/12A61P13/12A61P15/00A61P25/00A61P27/02A61P27/12A61P29/00A61P35/00A61P43/00
Inventor B·拉古B·皮奥
Owner JANSSEN PHARMA NV
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