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4-oxo-4,7-dihydro-thieno [2,3-b] pyridine-5-carboxamides as antiviral agent

A compound and bonding technology, applied in antiviral agents, drug combinations, organic chemistry, etc., can solve the problem of no reported compound biological activity

Inactive Publication Date: 2002-05-01
PHARMACIA & UPJOHN CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the biological activity of these compounds has not been reported

Method used

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  • 4-oxo-4,7-dihydro-thieno [2,3-b] pyridine-5-carboxamides as antiviral agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0238] Mp238-240°C; 1 H NMR (300MHz, DMSO-d 6 )δ13.37, 10.56, 8.71, 7.43-7.34, 4.54; 13 C NMR (75MHz, TFA) δ169.0, 167.1, 153.6, 139.5, 134.7, 133.2, 128.8, 128.8, 127.8, 127.6, 107.9, 43.8; IR (mull) 2785, 2753, 2694, 2672, 2317, 1996, 1668 , 1541, 1498, 1432, 1398, 1348, 803, 700, 610cm -1 ; MS (ESI-) m / z 317 (M-H) - H, 3.61; N, 8.72; Cl, ​​11.08; S, 9.98. Embodiment 2.N-(4-chlorobenzyl)-4-hydroxyl-2-iodothieno[2 , 3-b] pyridine-5-carboxamide

[0239] CHCl to ethyl 4-hydroxythieno[2,3-b]pyridine-5-carboxylate (J.HeterocyclicChem.1977,14,807) (5.22g) 3 (90 mL) to the solution were added portionwise mercuric oxide (7.10 g) and iodine (8.32 g). The reaction was stirred at room temperature for 18 hours. The reaction mixture was then filtered and the solid was washed with chloroform (400 mL). The organic layer was washed with water (200 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting orange solid was purified by column chromatograph...

Embodiment 3

[0241] Mp231-232(dec)℃; 1 H NMR (300MHz, DMSO-d 6 )δ13.27, 10.43, 8.69, 7.63, 7.41-7.33, 4.53; 13 C NMR (75 MHz, DMSO-d 6 )δ165.0, 142.1, 139.0, 133.1, 131.9, 131.2, 129.6, 128.8, 113.9, 74.5, 41.9; , 1473, 1293, 802, 785, cm -1 ; MS (ESI-) m / z 443 (M-H) - H, 2.41; N, 6.44; Cl, ​​7.81; S, 7.01. Embodiment 3.N-(4-chlorobenzyl)-4-hydroxyl-2-(4-morpholine Sulfonyl)thieno[2,3-b]pyridine-5-carboxamide

[0242] Morpholine (1.69 mL) was dissolved in dichloromethane (40 mL). Triethylamine (6.8 mL) was added and the reaction was cooled to 0°C. A solution of 5-nitro-2-thiophenesulfonyl chloride (3.69 g) in dichloromethane (25 mL) was then added dropwise. The reaction was stirred at 0°C for 15 minutes, then at room temperature for 30 minutes. The reaction mixture was concentrated in vacuo and the resulting brown solid was purified by column chromatography (dichloromethane). The same fractions were combined according to TLC and concentrated in vacuo to give 3.52 g (78%) of 2-m...

Embodiment 4

[0244] Mp > 300°C; 1 H NMR (300MHz, DMSO-d 6 )δ13.45, 10.29, 8.86, 7.81, 7.42-7.33, 4.55, 3.68, 3.02; 13 C NMR (75MHz, DMSO-d 6 )δ173.7, 164.5, 151.8, 144.3, 138.9, 131.9, 130.8, 129.6, 129.1, 128.8, 128.1, 114.7, 65.7, 46.3, 41.9; , 1340, 1334, 1260, 1155, 1115, 1076, 945, 733cm -1 ; MS (FAB) m / z 468 (MH + ); HRMS (FAB) measured value 468.0458; Analysis measured value: C, 48.69; H, 4.10; N, 8.91; Cl, ​​7.51; )-4-hydroxythieno[2,3-b]pyridine-5-carboxamide

[0245] To a solution of ethyl 4-hydroxythieno[2,3-b]pyridine-5-carboxylate (J. Heterocyclic Chem. 1977, 14, 807) (1.00 g) in chloroform (26 mL) was added dropwise Bromine (0.23 mL). The reaction was stirred at room temperature for 2 hours. The reaction mixture was poured into 2N HCl (30 mL), and the aqueous layer was extracted with chloroform (3 x 30 mL). The combined organic layers were washed with water (100 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford 0.840 g (62%) of the bro...

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Abstract

The invention provides a compound of formula (I), wherein R<1>, R<2>, R<3>, and R<4> have any of the values defined in the specification, or a pharmaceutically acceptable salt thereof, as well as processes and intermediates useful for preparing such compounds or salts, and methods of preventing or treating a herpesvirus infection using such compounds or salts.

Description

field of invention [0001] The present invention provides 4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamide derivatives, more precisely provides formula (I) 5-benzylaminocarbonyl - 4-oxo-4,7-dihydro-thieno[2,3-b]pyridine derivatives, which are useful as antiviral agents (for example as antiherpes virus agents). Background of the invention [0002] Herpes viruses include a large group of double-stranded DNA viruses. They are also the source of the most common viral diseases in humans. Eight herpesviruses have been shown to infect humans: herpes simplex virus types 1 and 2 (HSV-1 and HSV-2), varicella zoster virus (VZV), human cytomegalovirus (HCMV), Epstein-Barr virus (EBV) , and human herpesvirus types 6, 7, and 8 (HHV-6, HHV-7, and HHV-8). [0003] HSV-1 and HSV-2 cause herpetic lesions on the lips and genitals, respectively. They also occasionally cause eye infections and encephalitis. HCMV can cause birth defects in newborns and may tri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4365A61K31/5377A61P31/12A61P31/20A61P31/22C07D333/38C07D495/04
CPCC07D333/38C07D495/04A61P31/12A61P31/20A61P31/22A61P37/00
Inventor M·E·施努特M·M·卡达希A·斯科特
Owner PHARMACIA & UPJOHN CO
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