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Anti-viral compounds, pharmaceutical compositions, and methods of use thereof

A compound, carbon number alkyl technology, applied in antiviral compounds, pharmaceutical compositions and its application fields, can solve the unmet needs and huge problems of effective treatment of viral infections

Inactive Publication Date: 2016-03-02
KINETA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on the foregoing, there is a huge and unmet need in the industry for effective treatments of viral infections, including RNA viral infections

Method used

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  • Anti-viral compounds, pharmaceutical compositions, and methods of use thereof
  • Anti-viral compounds, pharmaceutical compositions, and methods of use thereof
  • Anti-viral compounds, pharmaceutical compositions, and methods of use thereof

Examples

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example 1

[0247] Example 1: Synthesis of compounds of the present invention

[0248] General Synthetic Scheme. Compounds of the present invention can be prepared by the methods described below in conjunction with synthetic methods well known to those skilled in the art. The starting materials used herein are commercially available or can be prepared by conventional methods known in the art (such as those disclosed in standard reference works, such as Compendium of Organic Synthetic Methods (COMPENDIUMO FORGANICSYNTHETICMETHODS), Volumes I-VI (Published by Wiley-Interscience). Preferred methods include those described below.

[0249]During any of the following synthetic sequences, it may be necessary and / or desirable to protect sensitive or reactive groups on any molecule of interest. This can be achieved by means of conventional protecting groups such as those described in: T.W. Greene, Protective Groups in Organic Chemistry, John Wiley & Sons, 1981; T.W. Greene and P.G.M. P.G.M. Wut...

example 2

[0269] Example 2. Synthesis of 3-(4-tert-butylphenyl)-4-oxo-4H-chromen-7-yl methanesulfonate

[0270]

[0271]

[0272] Step 1: Synthesis of intermediate 2-(4-tert-butylphenyl)-1-(2,4-dihydroxyphenyl)ethanone. (4-tert-butylphenyl)acetonitrile (10 g, 0.058 mol) and resorcinol (7.3 g, 0.066 mol) were added to 40 mL of BF3·Et2O and a flow of dry HCl gas was passed through the mixture overnight. The solution was then poured into 300 mL of cold water and stirred for 6 hours. The mixture was extracted with ethyl acetate and the solvent was evaporated to obtain an oil which was purified by chromatography to obtain 0.68 g of 3-(4-tert-butylphenyl)-7-hydroxy-4H-chromene-4 after chromatography - Ketones (20%).

[0273] Step 2: Synthesis of 3-(4-tert-butylphenyl)-7-hydroxy-4H-chromen-4-one. The intermediate from Step 1 (0.65 g, 2.3 mmol) was mixed with 1:1 triethyl orthoformate with anhydrous pyridine and piperidine and kept at 120-130 °C for 4 hours. The mixture was cooled and...

example 3

[0275] Synthesis of Example 3.N-[3-(4-tert-butylphenyl)-4-oxo-4H-chromen-7-yl]-N-methylmethanesulfonamide

[0276]

[0277] Step 1: Synthesis of N-(4-acetyl-3-hydroxyphenyl)methanesulfonamide. Add pyridine (1.6mL, 20mmol) to commercially available 4'-amino-2'-hydroxyacetophenone (2g, 13mmol) and methanesulfonyl chloride (1.6mL, 16mmol) in 40mL of anhydrous mixture in dichloromethane. The resulting mixture was stirred overnight at 0°C to room temperature, then diluted with dichloromethane and washed with 1M aqueous hydrochloric acid. Insoluble material appears at the interface between the two layers. The aqueous layer was back extracted twice with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and evaporated to obtain 0.11 g of sulfonamide. The insoluble material at the interface between the two extraction layers was filtered and rinsed with diethyl ether to obtain 1.3 g of sulfonamide (89% yield).

[0278] Step 2: Synthesis of N-{...

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Abstract

Disclosed herein are compounds, pharmaceutical compositions, and methods for the treatment of viral infection, including RNA viral infection, as well as compounds, pharmaceutical compositions, and methods for modulating the RIG-I pathway in a subject and / or in cells. These compounds are isoflavone derivatives, typically substituted at the 3-position with an aryl group and at the 7-position with a heterofunctional group.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to U.S. Provisional Patent Application No. 61 / 846,997, filed July 16, 2013, and U.S. Provisional Patent Application No. 61 / 991,417, filed May 9, 2014, both of which The entire content of the author is incorporated herein by reference. [0003] Statement of Government Interests [0004] This invention was made with Government support under Contract No. AI081335 to the National Institutes of Health. The government has certain rights in this invention. technical field [0005] The present invention provides, among other uses, compounds, pharmaceutical compositions, and methods for treating viral infections. These compounds modulate the retinoic acid inducible gene 1 (RIG-I) pathway. Background technique [0006] Viruses, such as RNA viruses, represent a huge public health problem in the United States and around the world. Well-known RNA viruses include influenza virus (including avian...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/353
CPCA61K31/5377A61K31/352A61K31/496C07D311/36C07D311/22A61P31/12A61P31/14A61P43/00A61K2300/00A61K39/13A61K39/145A61K39/155A61K39/21A61K39/29A61K39/39A61K2039/55511
Inventor 肖恩·P·艾度纳托克利斯汀·M·毕达德凯利·W·佛勒
Owner KINETA
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