Dihydroxyanthraquinones and their use

An alkyl and cyclic group technology, applied in the field of dihydroxyanthraquinones and their uses, can solve problems such as poor physical and chemical properties

Inactive Publication Date: 2008-10-29
SOSEI R&D LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The more widespread use of rhein has been somewhat limited by its rather poor physicochemical properties
The well-studied prodrug diacerein has not yet fully resolved this problem, and its use in clinical settings is again limited by poor physicochemical properties (P. Nicolas et al, Clin. Pharmacokinet., 1998, 35(5) , 347-359)

Method used

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  • Dihydroxyanthraquinones and their use
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  • Dihydroxyanthraquinones and their use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] 1,8-bis(tetrahydropyran-4-carbonyloxy)-3-(morpholine-4-carbonyl)-9,10-dioxo-9,10-dihydroanthracene

[0066]

[0067] In a 100ml flask equipped with a magnetic stirrer, 4,5-ditetrahydropyranyloxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (2.00g, 3.9×10 -3 mol) was stirred in DCM (50 mL) under nitrogen. Add EDCI (0.90g, 4.7×10 -3 mol) and HOBt (0.65g, 4.7×10 -3 mol) and the solution was stirred for 15 minutes. The solid suspension was dissolved in DCM solvent. Then add morpholine (0.54mL, 5.9×10 -3 mol) and the solution was stirred for 30 minutes.

[0068] The reaction mixture was diluted in 300 mL DCM. Sat. NaHCO with 200 mL 3 solution, and 200 mL of saturated NaCl solution to wash the organic layer. The organic layer was separated and evaporated to dryness under reduced pressure. The resulting residue was then triturated in water, filtered and dried under high vacuum to afford the desired product as a yellow solid (1.95 g, 87%).

[0069] 1 H NMR...

Embodiment 2

[0071] 1,8-bis(tetrahydropyran-4-carbonyloxy)-3-ethylcarbamoyl-9,10-dioxo-9,10-dihydroanthracene

[0072]

[0073] In a 100ml flask equipped with a magnetic stirrer, 4,5-ditetrahydropyranyloxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (2.00g, 3.9×10 -3 mol) in DCM (50 mL) was stirred under nitrogen. Add EDCI (0.90g, 4.7×10 -3 mol) and HOBt (0.65g, 4.7×10 -3 mol) and the solution was stirred for 15 minutes. The solid suspension was dissolved in DCM solvent. Then add ethylamine (3.00mL, 5.9×10 -3 mol) and the solution was stirred for 15 minutes.

[0074] The reaction mixture was then diluted in 300 mL DCM. Sat. NaHCO with 200 mL 3 solution, and 200 mL of saturated NaCl solution to wash the organic layer. The organic layer was separated and evaporated to dryness under reduced pressure. The resulting residue was then triturated in water, filtered and dried under high vacuum to afford the desired product as a yellow solid (1.56 g, 75%).

[0075] 1 H NMR (50...

Embodiment 3

[0078] 4,5-bis(tetrahydropyran-4-carbonyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 2-methoxyethyl ester

[0079]

[0080] Under nitrogen, to a 250 mL flask equipped with a magnetic stirrer, Dean-Stark apparatus, was added 2-methoxyethanol (300 mL) and 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid (3.00g, 10.6×10 -3 mol) and 0.1 mL of sulfuric acid. The mixture was refluxed for 24 hours (external oil bath temperature 145°C). The reaction mixture was then cooled to room temperature.

[0081] The resulting solid was filtered and washed with 10 mL of ice-cold diethyl ether. 2-Methoxyethyl 4,5-dihydroxy-9,10-dioxanthracene-2-carboxylate was isolated as a yellow solid (2.9 g, 81%).

[0082] 1 H NMR analysis was consistent with the desired product, (500MHz, DMSO)

[0083] δ=8.1(s, 1H, Ar), 7.8(t, 1H, Ar), 7.7(s, 1H, Ar), 7.7(d, 1H, Ar), 7.4(d, 1H, Ar), 4.4(t , 2H, COOCH 2 ), 3.7(t, 2H, CH 2 OCH 3 ), 3.3(s, 3H, CH 2 OCH 3 ).

[0084] Under nitroge...

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Abstract

A compound of formula (1), wherein X is H or -OCR1 and Y is H or -OCR2, provided that X and Y are not both H; and R is CH2OR9, CONR11R12, CN, tetrazole or COOR17; or a salt thereof, has therapeutic utility.

Description

technical field [0001] The present invention relates to dihydroxyanthraquinone derivatives and their use in treating diseases. Background technique [0002] T lymphocytes are known to play a central role in the pathogenesis of many inflammatory and autoimmune diseases. Activation of T cells by antigen-presenting cells is the initial event that initiates the inflammatory process, which subsequently leads to the activation of other inflammatory cells and subsequent release of pro-inflammatory cytokines, chemotactic agents and matrix-degrading enzymes. These cell types are also known to be essential for the initiation and maintenance of angiogenesis through secretion of VEGF. Angiogenesis-driven diseases include, but are not limited to, cancer, age-related macular degeneration, and diabetic retinopathy. [0003] Multiple sclerosis is a chronic demyelinating inflammatory disease of the central nervous system. T cell proliferation leads to the release of pro-inflammatory cytok...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/08A61K31/35A61P17/00A61P19/00A61P35/02A61P3/10
CPCC07D309/08A61P1/00A61P1/02A61P1/04A61P11/00A61P11/06A61P13/12A61P17/00A61P19/00A61P19/02A61P19/10A61P25/00A61P27/02A61P29/00A61P3/00A61P35/00A61P35/02A61P35/04A61P37/02A61P37/06A61P3/10A61K31/35
Inventor 安德鲁·道格拉斯·巴克斯特安德列亚·瓦尔姆斯利
Owner SOSEI R&D LTD
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