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Compositions and methods for treatment of cardiovascular disease

A composition and compound technology, applied in the field of compounds for the treatment of cardiovascular diseases, can solve the problems of biosafety and non-toxic inhibitors yet to be developed, plaque rupture, etc.

Inactive Publication Date: 2012-05-16
INVASC THERAPEUTICS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Additionally, MPO has been shown to play an important role in plaque destabilization leading to plaque rupture
[0008] However, although MPO is widely implicated in the etiology and progression of cardiovascular diseases, biosafe and nontoxic inhibitors of MPO have yet to be developed

Method used

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  • Compositions and methods for treatment of cardiovascular disease
  • Compositions and methods for treatment of cardiovascular disease
  • Compositions and methods for treatment of cardiovascular disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0259] Synthesis and characterization of embodiment 1-methylenedioxyphenyl ferulic acid ester

[0260] For the synthesis of methylenedioxyphenyl ferulate (general formula (II), the chemicals and reagents of the synthesis process described below include: ferulic acid, methylenedioxyphenol, dimethylaminopyridine (DMAP) , triethylamine (TEA), and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDCl) were purchased from Sigma-Aldrich (St. Louis, MO) .

[0261] During the synthesis step, figure 1 As described in , the synthesis of methylenedioxyphenyl ferulic acid ester was completed by the coupling reaction of ferulic acid and methylenedioxyphenol, and the whole reaction was carried out in a nitrogen atmosphere. In order to complete this reaction, 0.194g (1 millimolar (mM)) ferulic acid; 0.138g (1mM) methylenedioxyphenol, 0.101g triethylamine, corresponding volume: 0.140ml; Dimethylaminopyridine catalyst consumption ( approximately 1 mg to 2 mg), mixed in a 100 ...

Embodiment 2

[0269] Synthesis and characterization of embodiment 2-ferulic acid proline

[0270] For the synthesis of proline ferulic acid (general formula (XVI)), the chemicals and reagents used in the synthesis process described below include: ferulic acid, L-proline methyl ester hydrochloride, dimethylaminopyridine ( DMAP), and dicyclohexylcarbodiimide (DCC), were first purchased from Sigma-Aldrich (St. Louis, MO). The synthesis of ferulic acid proline is accomplished by the coupling reaction of ferulic acid and proline methyl ester, followed by regeneration of the free carboxylic acid by base-catalyzed hydrolysis of the ester. The entire reaction was carried out under nitrogen atmosphere.

[0271] In the first step of the reaction, figure 2 0.194 g (1 mM) ferulic acid, 0.165 g (1 mM) proline ester, 0.101 g dimethylaminopyridine (DMAP) were mixed in a 100 mL round bottom flask as described in . The contents of the flask were dissolved in 25 mL of dichloromethane and stirred unifor...

Embodiment 3

[0284] Example 3 - Inhibition of myeloperoxidase (MPO) activity

[0285] In order to determine whether the compounds of the present invention inhibit the activity of myeloperoxidase (MPO) at different concentrations, tetramethylbenzidine (TMB) was used as a substrate in the myeloperoxidase (MPO) test because it was more effective than guaiac Wood phenol is more sensitive and the color is more stable. Typically, 200 μl of the reaction mixture contained 20 mU of human myeloperoxidase (MPO) (Sigma-Aldrich, St. Louis, MO), 400 nmol H 2 o 2 , 1.6 μmol TMB, varying concentrations of methylenedioxyphenyl ferulate (general formula (II)) or ferulic acid proline (general formula (XVI)).

[0286] Reactions were performed in (200 μl, 50 mM) sodium acetate buffer at pH=5.6. MPO was added to initiate the reaction, and the optical density of the resulting product was read at 650 nm at different time points using a microplate reader. The results confirmed that two compounds, methylenedi...

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Abstract

Ortho methoxy phenolic compounds are provided that include methylenedioxyphenyl ferulate and ferulylproline and derivatives thereof. Pharmaceutical compositions comprising the compounds and methods of using the compounds for treating cardiovascular diseases, including hypertension, atherosclerosis, coronary heart disease, angina, stroke, and myocardial infarction, are further provided. The compounds are also useful in reducing low-density lipoprotein oxidation, improving or increasing vasodilation, and reducing plaque destabilization in a subject.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application No. 61 / 214,425, filed April 23, 2009, the entire disclosure of which is incorporated herein by reference. field of invention [0003] The present invention relates to compounds and methods for treating cardiovascular diseases. In particular, the present invention relates to o-methoxyphenolic compounds, including methylenedioxyphenyl ferulate and proline ferulate, and derivatives thereof, useful for reducing the activity of myeloperoxidase (MPO) enzymes , so it can effectively treat cardiovascular diseases such as hypertension, atherosclerosis, coronary heart disease, angina pectoris, stroke, and myocardial infarction. In addition, the present invention also relates to the use of o-methoxyphenol compounds and their derivatives to reduce the oxidation of low-density lipoprotein and high-density lipoprotein, increase or improve vasodilation, reduce plaque insta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/46C07D405/02A61P9/00A61K31/357
CPCC07D317/72C07D211/60C07D217/26C07D207/16C07D317/68C07D319/20C07D405/12A61K31/357C07D317/64C07D317/66C07D319/18A61P29/00A61P3/00A61P3/06A61P39/06A61P43/00A61P7/02A61P9/00A61P9/08A61P9/10A61P9/12A61P9/14C07D317/54
Inventor D·拉杰哥帕尔
Owner INVASC THERAPEUTICS INC
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