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Adenosine A3 receptor agonists

A technology for compounds, chemical formulas, applied in the field of preparing these compounds

Inactive Publication Date: 2004-10-20
GILEAD PALO ALTO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, typical xanthine and non-xanthine A 1 and A 2 Receptor antagonists do not appear to bind this receptor (Zhou et al.)

Method used

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  • Adenosine A3 receptor agonists
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  • Adenosine A3 receptor agonists

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0176] The preparation of the compound of chemical formula (2)

[0177] a. The preparation of the compound of chemical formula (2), wherein R 1 is a methyl group, and X is a total price bond

[0178]

[0179] 3,4-diacetoxy-2-(2,6-dichloropurin-9-yl)-5-(2-oxopropoxy)tetrahydrofuran, the compound (1mmol) of chemical formula (1) was suspended in 1 :4 in a mixture of methylamine / MeOH and the mixture was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure and the residue was triturated in ether to give (4S,2R,3R,5R)-2-[2-chloro-6-(methylamino)purin-9-yl]-5-(hydroxymethyl ) oxolane-3,4-diol (phenol), a compound of formula (2) in the form of a white solid.

[0180] b. The preparation of the compound of chemical formula (2), change R 1 and x

[0181] Similarly, following the procedure of 1A above, but substituting propylamine and 3-iodoaniline for methylamine, the following compound of formula (2) was prepared: (4S,2R,3R,5R)-2-[...

Embodiment 2

[0198] The preparation of the compound of chemical formula (3)

[0199] a. The preparation of the compound of chemical formula (3), wherein R 1 is a methyl group, and X is a total price bond

[0200]

[0201] (4S, 2R, 3R, 5R)-2-[2-Chloro-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol , the compound of chemical formula (2) (0.5 mmol) was suspended in a mixture of hydrazine hydrate (5 mL), and the mixture was stirred at room temperature for 24 hours. Hydrazine was removed under reduced pressure and the residue was triturated in ether and filtered to give (4S,2R,3R,5R)-2-[2-hydrazino-6-(methylamino)purin-9-yl]-5-( Hydroxymethyl)oxolane-3,4-diol, the compound of formula (3) in the form of a white solid.

[0202] b. Preparation of compounds of formula (3), changing R 1 and x

[0203] Similarly, following the procedure of 2A above, but replacing 2-[2-chloro-6-methylaminopurin-9-yl]-5-hydroxymethyltetrahydrofuran-3 with propylamine and 3-iodoaniline ...

Embodiment 3

[0219] Preparation of compounds of formula (I)

[0220] a. The preparation of the compound of chemical formula (I), wherein R 1 is methyl, R 2 for 4-(4- Methoxyphenyl) pyrazol-1-yl, and X is a covalent bond

[0221]

[0222] chemical formula I

[0223] (4S, 2R, 3R, 5R)-2-[2-hydrazine-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol (0.5 mmol) was suspended in 3 mL of ethanol, and the compound 2-(4-methoxyphenyl)propionaldehyde of the chemical formula (4) was added to the suspension. The mixture was heated to reflux for 5 hours, and the formed precipitate was collected by filtration, washed with ethanol and ether to give (4S, 2R, 3R, 5R)-5-(hydroxymethyl)-2-{2-[4-( 4-methoxyphenyl) pyrazolyl]-6-(methylamino)purin-9-yl}-oxolane (oxolane)-3,4-diol, the compound of chemical formula I, Ms, 455.43( M+1).

[0224] b. Preparation of Compounds of Formula I, Variation R 1 、R 2 , and X

[0225] Similarly, follow the procedure of 3A above, but option...

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PUM

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Abstract

Disclosed are novel compounds that are A3 adenosine receptor agonists, useful for treating various disease states, including cancer, cardiac ischemia, leukopenia, and neutropennia.

Description

technical field [0001] This application claims priority to US Provisional Patent Application Serial No. 60 / 311,069, filed August 8, 2001, the disclosure of which is incorporated herein by reference. The present invention relates to a novel adenosine A3 receptor agonist useful for the treatment of neurological disorders, cardiac disorders, and other cell proliferation disorders. The invention also relates to processes for the preparation of these compounds, as well as pharmaceutical compositions containing these compounds. Background technique [0002] Adenosine is a naturally occurring nucleoside known as A 1 、A 2a 、A 2b , and A 3 The adenosine receptor family interacts to exert biological effects. For example, A 1 Stimulation of adenosine receptors shortens the duration and reduces the amplitude of action potentials in AV ganglion cells and, therefore, prolongs the refractory period of AV ganglion cells. In this way, A 1 Stimulation of the receptor provides a means ...

Claims

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Application Information

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IPC IPC(8): C07H19/173A61K31/7076A61P7/00A61P9/00A61P13/12A61P15/08A61P25/00A61P35/00A61P43/00C07H19/16
CPCC07H19/16A61P13/12A61P15/08A61P25/00A61P35/00A61P43/00A61P7/00A61P9/00
Inventor 埃尔法蒂赫·埃尔扎因文卡塔·帕勒维布哈夫·瓦尔凯赫特卡杰夫·扎布沃茨基
Owner GILEAD PALO ALTO
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