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Chalcone derivatives and their use to treat diseases

a technology of chalcone and derivatives, applied in the field of chalcone derivatives and their use to treat diseases, can solve the problems of thrombosis, myocardial infarction and ischemic heart disease, late graft loss, and thrombosis of the transplanted organ

Inactive Publication Date: 2006-08-24
NI LIMING +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text describes the discovery of certain compounds that can inhibit the expression of a protein called VCAM-1, which is involved in inflammatory disorders such as arthritis, asthma, and diabetes. These compounds can also be used to treat skin diseases and transplant rejection. The patent describes a formula for the compounds and their pharmaceutically acceptable salts or esters. The technical effect of this patent is the discovery of new compounds that can help treat inflammatory disorders and cardiovascular disease by inhibiting the expression of VCAM-1.

Problems solved by technology

In advanced stages of the disease atherosclerotic lesions can become unstable resulting in plaque rupture, thrombosis, myocardial infarction and ischemic heart disease.
Acute transplant rejection occurs when the transplant recipient recognizes the grafted organ as “non-self” and mounts an immune response characterized by massive infiltration of immune cells, edema, and hemorrage that result in the death of the transplanted organ.
Chronic graft rejection also known as allograft vasculopathy is distinct from acute transplant rejection and is a leading cause of late graft loss after renal and heart transplantation.

Method used

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  • Chalcone derivatives and their use to treat diseases
  • Chalcone derivatives and their use to treat diseases
  • Chalcone derivatives and their use to treat diseases

Examples

Experimental program
Comparison scheme
Effect test

embodiment 6c

[0620] In a 61st embodiment, the invention is represented by Formula I or its pharmaceutically acceptable salt or ester, wherein:

[0621] R2β, R3β, R4β, R5β, R6β, R2α, R3α, R4α, R5α and R6α are independently selected from the group consisting of hydrogen, halogen, nitro, alkyl, lower alkyl, alkenyl, alkynyl, carbocycle, cycloalkyl, cycloalkylalkyl, haloalkyl, aryl, arylalkyl, heteroaryl, heteroaryl lower alkyl, heterocyclic, heterocyclic lower alkyl, alkylthioalkyl, cycloalkylthioalkyl, arylthio lower alkyl, aralkyl lower thioalkyl, heteroarylthio lower alkyl, heteroaralkyl lower thioalkyl, heterocyclicthio lower alkyl, heterocyclicalkyl lower thioalkyl, lower alkyl S(O)-lower alkyl, lower alkyl-S(O)2-lower alkyl, arylsulfinyl lower alkyl, arylsulfonyl lower alkyl, —C(O)R2, R2C(O)alkyl, aminoalkyl, cycloalkylaminoalkyl, arylamino lower alkyl, heteroarylamino lower alkyl, heterocyclicamino lower alkyl,

[0622] hydroxyl, hydroxyalkyl, alditol, carbohydrate, polyol alkyl, alkoxy, lower a...

example 1

[0844]

1-(2,2-Bis-hydroxymethyl-benzo[1,3]dioxol-5-yl)-3E-3,4-dimethoxy-5-thiophen-2-yl-phenyl)propenone

[0845] Ex-1A: Catechol (2.2 g, 20 mmol) was dissolved in acetone. Diethyl dibromomalonate (7.0 g, 22 mmol) and potassium carbonate (2.76 g) were added, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water was added to the residue. The residue was extracted with dichloromethane, and the organic phase was washed with brine, dried over magnesium sulfate and evaporated. Chromatography (hexanes / ethyl acetate, 4:1) gave 3.9 g of benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester. 1H-NMR (CDCl3) δ 6.90-6.97 (m, 4H), 4.37(q, J=7 Hz, 4H), 1.32(t, J=7 Hz, 6H).

[0846] Ex-1B: [Bis(ethoxycarbonyl)methyldenedioxy]benzene obtained from Ex-1A (3.9 g, 14.7 mmol) was dissolved in THF (100 mL) and cooled with ice-water. Lithium aluminum hydride (1 M solution in THF, 44 mL) was added dropwise, and the mixture was stirred overnight. Th...

example 2

[0850]

1-(2,2-Bis-hydroxymethyl-benzo[1,3]dioxol-5-yl)-3E-(4-thiophen-2-yl-phenyl)-propenone

[0851] Ex-2A: 4-(Thien-2-yl)benzaldehyde was obtained in a similar manner as described in Ex-1D from 4-bromobenzaldehyde. 1H-NMR (CDCl3) δ 10.00 (s, 1H), 7.88 (d, J=9 Hz, 2H), 7.77 (d, J=9 Hz, 2H), 7.46 (d, J=4 Hz, 1H), 7.39-7.41 (m, 1H), 7.12-7.15 (m, 1H).

[0852] The title compound was obtained when 5-acetyl-benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester from Ex-1C was condensed with 4-(Thien-2-yl)benzaldehyde from Ex-2A in a similar manner as described in Ex-1. Yellow solid, mp 166-168° C., 23.6% yield. 1H-NMR (CDCl3) δ 7.77 (d, J=15 Hz, 1H), 7.60-7.65 (m, 5H), 7.51 (d, J=2 Hz, 1H), 7.45 (d, J=15 Hz, 1H), 7.37-7.38 (m, 1H), 7.32(d, J=5 Hz, 1H), 7.09 (dd, J=4, 5 Hz, 1H), 6.88 (d, J=8 Hz, 1H), 3.96 (d, J=7 Hz, 4H). MS m / z=394 ([M]+, 50%), 363 (100%). HRMS (EI) Calcd. for C22H18O5S: 394.0875. Found: 394.0869.

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Abstract

The invention relates to compounds, pharmaceutical compositions and methods of using compounds of the general formula or its pharmaceutically acceptable salt or ester, wherein the substituents are defined in the application.

Description

[0001] This patent application claims priority to U.S. Provisional Patent Application Ser. No. 60 / 342,034 filed Dec. 19, 2001 and U.S. Provisional Patent Application Ser. No. 60 / 386,482 filed Jun. 5, 2002.[0002] The present invention is in the field of novel chalcone derivatives, pharmaceutical compositions and methods for treating a variety of diseases and disorders, including inflammation and cardiovascular disease. BACKGROUND OF THE INVENTION [0003] Adhesion of leukocytes to the endothelium represents a fundamental, early event in a wide variety of inflammatory conditions, autoimmune disorders and bacterial and viral infections. Leukocyte recruitment to endothelium is mediated in part by the inducible expression of adhesion molecules on the surface of endothelial cells that interact with counterreceptors on immune cells. Endothelial cells determine which types of leukocytes are recruited by selectively expressing specific adhesion molecules, such as vascular cell adhesion molecul...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/70A61K31/445A61K31/41A61K31/40A61K31/341A61K31/381A61K31/4025A61K31/404A61K31/4164A61K31/4184A61K31/4192A61K31/4196A61K31/42A61K31/422A61K31/426A61K31/437A61K31/4406A61K31/4436A61K31/505A61K31/5377A61P1/00A61P3/10A61P9/08A61P9/10A61P11/00A61P11/06A61P11/16A61P13/12A61P17/00A61P17/02A61P17/06A61P19/02A61P27/02A61P27/16A61P29/00A61P37/02A61P37/08A61P43/00C07C45/63C07C47/575C07D207/32C07D207/333C07D209/12C07D213/30C07D213/50C07D231/12C07D233/54C07D233/64C07D235/18C07D239/26C07D239/34C07D239/52C07D241/12C07D249/08C07D257/04C07D261/08C07D277/24C07D307/28C07D307/46C07D307/80C07D333/12C07D333/16C07D333/20C07D333/22C07D333/38C07D333/40C07D333/56C07D409/10C07D409/12C07D413/12C07D471/04C07H15/203
CPCC07C45/63C07C47/575C07D207/333C07D209/12C07D213/50C07D231/12C07D233/64C07D235/18C07D239/26C07D239/52C07D241/12C07D249/08C07D257/04C07D261/08C07D277/24C07D307/28C07D307/46C07D307/80C07D333/22C07D333/38C07D333/56C07D409/10C07D409/12C07D413/12C07D471/04C07H15/203A61P1/00A61P11/00A61P11/06A61P11/16A61P13/12A61P17/00A61P17/02A61P17/06A61P19/02A61P27/02A61P27/16A61P29/00A61P37/02A61P37/08A61P43/00A61P9/00A61P9/08A61P9/10A61P3/10
Inventor NI, LIMINGWORSENCROFT, KIMBERLYWEINGARTEN, M.MENG, CHARLESSIKORSKI, JAMES
Owner NI LIMING
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