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Chalcone derivatives and their use to treat diseases

A technology of compound, alkyl, applied in the field of new chalcone derivatives

Inactive Publication Date: 2005-03-16
ATHEROGENICS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been shown that VCAM-1 is upregulated 24 hours after nasal allergen challenge in patients with seasonal allergic rhinitis (Braunstahl, G.J. et al., J. Allergy Clin. Immunol., 107:469-476, 2001), but not in normal objects

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

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Experimental program
Comparison scheme
Effect test

Embodiment approach 6c

[0603] Embodiment 6c. Amide Moiety

[0604] In a 61st embodiment, the invention is represented by Formula I or a pharmaceutically acceptable salt or ester thereof, wherein:

[0605] R 2β , R 3β , R 4β , R 5β , R 6β , R 2α , R 3α , R 4α , R 5α and R 6α independently selected from hydrogen, halogen, nitro, alkyl, lower alkyl, alkenyl, alkynyl, carbocycle, cycloalkyl, cycloalkylalkyl, haloalkyl, aryl, aralkyl, heteroaryl group, heteroaryl-lower alkyl, heterocycle, heterocycle-lower alkyl, alkylthioalkyl, cycloalkylthioalkyl, arylthio-lower alkyl, aralkyl-lower-thioalkyl, hetero Arylthio-lower alkyl, heteroaralkyl-lower thioalkyl, heterocyclic thio-lower alkyl, heterocycloalkyl-lower thioalkyl, lower alkyl S(O)-lower alkyl, lower alkyl -S(O) 2 -lower alkyl, arylsulfinyl lower alkyl, arylsulfonyl lower alkyl, -C(O)R 2 , R 2 C(O)alkyl, aminoalkyl, cycloalkylaminoalkyl, arylamino lower alkyl, heteroarylamino lower alkyl, heterocyclic amino lower alkyl, hydroxyl, hydroxy...

Embodiment 1

[0860]

[0861] 1-(2,2-Dihydroxymethylbenzo[1,3]dioxol-5-yl)-3E-(3,4-Dimethoxy-5-thiophen-2-yl phenyl) propenone

[0862] 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 separated under reduced pressure, and water was added to the residue. The residue was extracted with dichloromethane, the organic phase was washed with brine, dried over magnesium sulfate and evaporated. Chromatography (hexane / ethyl acetate, 4:1) gave 3.9 g of diethyl benzo[1,3]dioxole-2,2-dicarboxylate. 1 H-NMR (CDCl 3 ) δ6.90-6.97 (m, 4H), 4.37 (q, J = 7Hz, 4H), 1.32 (t, J = 7Hz, 6H).

[0863] Ex-1B: [bis(ethoxycarbonyl)methyldenedioxy]benzene (3.9 g, 14.7 mmol) obtained from Ex-1A was dissolved in THF (100 mL) and cooled with ice water. Lithium aluminum hydride (1M in THF, 44 mL) was added dropwise, and the mixture was stirred ov...

Embodiment 2

[0868]

[0869] 1-(2,2-Dihydroxymethylbenzo[1,3]dioxol-5-yl)-3E-(4-thiophen-2-ylphenyl)propenone

[0870] Ex-2A: 4-(thiophen-2-yl)benzaldehyde was obtained from 4-bromobenzaldehyde following a similar procedure as described in Ex-ID. 1 H-NMR (CDCl 3 )δ10.00(s, 1H), 7.88(d, J=9Hz, 2H), 7.77(d, J=9Hz, 2H), 7.46(d, J=4Hz, 1H), 7.39-7.41(m, 1H ), 7.12-7.15 (m, 1H).

[0871] Diethyl 5-acetylbenzo[1,3]dioxol-2,2-dicarboxylate from Ex-1C and 4-(thiophen-2-yl)benzaldehyde from Ex-2A Condensation was carried out in a similar manner as described in Ex-1 to obtain the title compound. Yellow solid, mp 166-168°C, 23.6% yield. 1 H-NMR (CDCl 3 )δ7.77(d, J=15Hz, 1H), 7.60-7.65(m, 5H), 7.51(d, J=2Hz, 1H), 7.45(d, J=15Hz, 1H), 7.37-7.38(m , 1H), 7.32 (d, J=5Hz, 1H), 7.09 (dd, J=4, 5Hz, 1H), 6.88 (d, J=8Hz, 1H), 3.96 (d, J=7Hz, 4H). MS m / z=394 ([M] + , 50%), 363 (100%). HRMS (EI) calculated value C 22 h 18 o 5 S: 394.0875. Measured value: 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 US Provisional Patent Application Serial No. 60 / 342,034, filed December 19, 2001, and US Provisional Patent Application Serial No. 60 / 386,482, filed June 5, 2002. [0002] The present invention relates to novel chalcone derivatives, pharmaceutical compositions and methods for the treatment of various diseases and conditions including inflammation and cardiovascular disease. Background of the invention [0003] Adhesion of leukocytes to the endothelium represents a fundamental early event in a variety of inflammatory conditions, autoimmune diseases, and bacterial and viral infections. The recruitment of leukocytes to the endothelium is mediated in part by the induced expression of adhesion molecules on the surface of endothelial cells that interact with counter-receptors on immune cells. Endothelial cells determine which types of leukocytes to recruit by selectively expressing specific adhesion molecules,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/341A61K31/381A61K31/40A61K31/4025A61K31/404A61K31/41A61K31/4164A61K31/4184A61K31/4192A61K31/4196A61K31/42A61K31/422A61K31/426A61K31/437A61K31/4406A61K31/4436A61K31/505A61K31/5377A61P1/00A61P3/10A61P9/08A61P9/10A61P11/00A61P11/06A61P11/16A61P13/12A61P17/00A61P17/02A61P17/06A61P19/02A61P27/02A61P27/16A61P29/00A61P37/02A61P37/08A61P43/00C07C45/63C07C47/575C07D207/32C07D207/333C07D209/12C07D213/30C07D213/50C07D231/12C07D233/54C07D233/64C07D235/18C07D239/26C07D239/34C07D239/52C07D241/12C07D249/08C07D257/04C07D261/08C07D277/24C07D307/28C07D307/46C07D307/80C07D333/12C07D333/16C07D333/20C07D333/22C07D333/38C07D333/40C07D333/56C07D409/10C07D409/12C07D413/12C07D471/04C07H15/203
CPCC07D471/04C07D277/24C07D307/80C07D207/333C07D409/12C07H15/203C07D261/08C07D257/04C07D239/52C07D213/50C07D239/26C07D231/12C07D249/08C07D409/10C07D333/56C07C47/575C07D241/12C07C45/63C07D307/46C07D413/12C07D209/12C07D235/18C07D233/64C07D307/28C07D333/38C07D333/22A61P1/00A61P11/00A61P11/06A61P11/16A61P13/12A61P17/00A61P17/02A61P17/06A61P19/02A61P27/02A61P27/16A61P29/00A61P37/02A61P37/08A61P43/00A61P9/00A61P9/08A61P9/10A61P3/10
Inventor L·倪K·J·沃森罗夫特M·D·维恩加坦C·Q·孟J·A·斯科斯基
Owner ATHEROGENICS INC
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