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Substituted thiophene- and furan-fused azolopyrimidine-5-(6h)-one compounds

A technology of chemical entities and haloalkyl groups, which is applied in the fields of active ingredients of heterocyclic compounds, drug combinations, organic chemistry, etc.

Active Publication Date: 2015-04-29
다트뉴로사이언스엘엘씨
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, effective PDE1 inhibitors with pharmaceutical properties are urgently needed

Method used

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  • Substituted thiophene- and furan-fused azolopyrimidine-5-(6h)-one compounds
  • Substituted thiophene- and furan-fused azolopyrimidine-5-(6h)-one compounds
  • Substituted thiophene- and furan-fused azolopyrimidine-5-(6h)-one compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0323] Example 1.6-(2-Chlorobenzyl)thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

[0324]

[0325] Step A: Methyl 3-cyanothiophen-2-ylcarbamate.

[0326] Methyl chloroformate (7.61 g, 80.5 mmol) was added dropwise to a stirred solution of 2-amino-3-cyanothiophene (10 g, 80.5 mmol) and pyridine (19.1 g, 242 mmol) in DCM (250 mL) at 0 °C . After the addition, the mixture was warmed to room temperature and stirred overnight. The reaction was treated with water (50 mL) and extracted with DCM (3 x 150 mL). The combined organic phases were washed with 1 N HCl (2 x 150 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL) and dried over sodium sulfate. The organic layer was filtered and concentrated under reduced pressure to afford the crude product, which was triturated with a solution of methyl tert-butyl ether and petroleum ether (1:1, 50 mL) to afford the title compound (11 g, 75 mL) as an off-white solid. %). 1 H NMR (400MHz, CDCl 3 )δ3.90(s, 3H), ...

Embodiment 2

[0332] Example 2.6-(3-chlorobenzyl)thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

[0333]

[0334] 1 H NMR (400MHz, CDCl 3 )δ5.64 (s, 2H), 7.16 (d, 1H), 7.35-7.25 (m, 3H), 7.48 (s, 1H), 7.62 (d, 1H), 8.33 (s, 1H). [M+H] = 317.0.

Embodiment 3

[0335] Example 3.6-(4-chlorobenzyl)-9-methylthieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

[0336]

[0337] 1 H NMR (400MHz, CDCl 3 )δ 2.67(s,3H), 5.40(s,2H), 6.74(s,1H), 7.33(d,2H), 7.43(d,2H), 8.33(s,1H). [M+H] = 331.0.

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PUM

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Abstract

Described herein are compounds of Formula I and Formula II, methods of their synthesis, compositions comprising the compounds, and use of the compounds and compositions in treating numerous diseases and disorders, including cognitive deficits associated with CNS diseases and disorders.

Description

[0001] References to related applications [0002] This application claims the benefit of US Provisional Application 61 / 661,091, filed June 18, 2012, which is hereby incorporated by reference in its entirety. field of invention [0003] The present invention relates to certain substituted thiophene-fused and furan-fused azolopyrimidin-5-(6h)-one compounds and derivatives of such compounds; pharmaceutical compositions comprising them, methods of preparing them and their Use in various methods of inhibiting the PDE1 enzyme; and treatment of one or more disorders, including neurological disorders, cardiovascular disorders, renal diseases, and other conditions and diseases associated with PDE1 or cyclic nucleotide signaling. Background of the invention [0004] The cyclic nucleotides 5'-3' cyclic adenosine monophosphate (cAMP) and 5'-3' cyclic guanosine monophosphate (cGMP) are second messenger molecules that transmit signals from receptors on the cell surface to intracellular ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/14A61K31/519A61P25/00A61P9/00
CPCC07D471/14C07D487/14C07D519/00C07D495/14C07D495/22C07D495/12A61P25/00A61P9/00C07D491/147A61K31/519A61K31/5377A61K31/541C07D487/22C07D491/22C07D498/08C07D491/107A61K31/55A61K31/551A61K31/553A61K31/5386
Inventor 詹姆士·布莱特恩布什尔布赖恩·布兰施泰特布赖恩·戴克劳伦·戈麦斯安德鲁·理查德·哈德森塔米·乔·马洛内特洛伊·维克斯马尔科·彼得斯
Owner 다트뉴로사이언스엘엘씨
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