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Novel pyrazine derivatives or salts thereof, containing the derives or the salts and intermediates for the preparation of both

A technology of pyrazine derivatives and compositions, applied in the field of new pyrazine derivatives or their salts, pharmaceutical compositions containing the derivatives or salts, and intermediates for the preparation of the two

Inactive Publication Date: 2003-05-14
TOYAMA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the method for preparing the compound represented by the general formula [22] and the intermediates used for the preparation are mentioned in this patent application, there is no reference to the flupyrazine derivatives of the present patent application in the above-mentioned patent application as a compound represented by the general formula [22] 22] Description of the use of the representative compound for the preparation of intermediates

Method used

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  • Novel pyrazine derivatives or salts thereof, containing the derives or the salts and intermediates for the preparation of both

Examples

Experimental program
Comparison scheme
Effect test

reference example I-2

[0417] In a nitrogen atmosphere, 11.4g of 6-bromo-3-methoxy-2-pyrazinecarboxylic acid methyl ester was dissolved in 227mL of toluene, and 10.3g of benzophenone imine, 0.42g of tris(dibenzylidene Acetone) dipalladium, 0.86 g (s)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and 6.20 g sodium tert-butoxide. The resulting mixture was stirred at 80 °C for one hour. After cooling the reaction mixture was filtered. The filtrate was purified by column chromatography (eluent: toluene:ethyl acetate=20:1). The obtained oily product was dissolved in 140 mL of tetrahydrofuran, 7 mL of 2 mol / L hydrochloric acid was added, and the resulting mixture was stirred at room temperature for 15 minutes. A mixture of 200 mL of chloroform and 50 mL of water was added to the reaction mixture, and then 1 mol / L sodium hydroxide was added to basify the mixture, and the organic layer was separated. The resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried ove...

reference example I-10

[0452] In 6.0 mL of N,N-dimethylformamide, 0.24 g of methyl 3-oxo-3,4-dihydro-2-pyrazinecarboxylate was dissolved. After adding 82 mg of 18-crown-6-ether and 62 mg of sodium hydride, the resulting mixture was heated at 80° C. for one hour. Then, 0.30 g (4aR, 7S, 8aR)-2-phenylhexahydropyrano[3,2-d][1,3]dioxan-7-yl 4-methylbenzenesulfonate was added dropwise 3.0 mL of N,N-dimethylformamide solution, and the resulting mixture was heated at 100°C for 4 hours. The reaction mixture was allowed to cool, diluted with 50 mL of ethyl acetate and 25 mL of water, and the layers were separated. Further, the aqueous layer was extracted with three 25 mL portions of ethyl acetate. All the obtained organic layers were combined, washed successively with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by column c...

reference example I-11

[0456]In 5.7 mL of N,N-dimethylformamide, 0.38 g of methyl 3-oxo-3,4-dihydro-2-pyrazinecarboxylate was dissolved. After adding 0.10 g of sodium hydride, the resulting mixture was heated at 80° C. for 30 minutes. Then, 0.19 g (4aR, 7R, 8S, 8aR)-8-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxan-7-yl 4-methanol was added The phenylsulfonate was heated at 100°C for an additional 4.5 hours. The reaction mixture was allowed to cool, diluted with 30 mL of ethyl acetate and 20 mL of water, and the resulting mixture was separated. Further, the aqueous layer was extracted with 30 mL of ethyl acetate. All the obtained organic layers were combined, washed successively with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography (eluent: toluene:ethyl acetate=2:1), isopropyl ether and die...

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Abstract

Pyrazine derivatives represented by general formula Ä1Ü: <CHEM> wherein the variables are as defined in the specification, or salts thereof have an excellent antiviral activity and are useful as a therapeutic agent for treating viral infections. Further, fluoropyrazine-carboxamide derivatives represented by general formula Ä2Ü: <CHEM> wherein the variables are as defined in the specification, or salts thereof are useful as an intermediate for production of the compounds of general formula Ä1Ü, and as an intermediate for production of the fluoropyrazine-carboxamide derivatives of which one typical example is 6-fluoro-3-hyroxy-2-pyrazine-carboxamide having an antiviral activity.

Description

technical field [0001] The present invention relates to novel pyrazine derivatives or their salts, pharmaceutical compositions containing them and intermediates for their preparation. Background technique [0002] As antiviral agents in clinical use today, acyclovir and vidarabine for the control of herpes virus, ganciclovir and foscarnet for the control of cytomegalovirus, and Viral interferon, etc. Furthermore, the use of vaccine prophylaxis is widely applicable against influenza virus, for which small molecule compounds such as amantadine hydrochloride and ribavirin are also used. Furthermore, recently, zanamivir (zanamivir) is also used. [0003] On the other hand, for example, with regard to the antiviral activity of pyrazine ring-based nucleoside- and nucleotide-analogues, compounds of the following general formula have hitherto been reported to have antiviral activity: where R 7 Represents a hydrogen atom, methyl or C 10 h 21 . However, this type of compound s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P31/12C07H19/04
CPCC07H19/04A61P31/12A61P31/16
Inventor 江川裕之古田要介杉田淳上原小百合濱元昭一米泽健治
Owner TOYAMA CHEM CO LTD
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