Methods of treating influenza viral infections

A technology for effective treatment of influenza virus infection, applied in pharmaceutical formulations, medical preparations containing active ingredients, active ingredients of halogenated hydrocarbons, etc., can solve problems such as harmfulness, incomplete subtypes, side effects, etc.

Inactive Publication Date: 2009-03-18
ERIMOS PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] While various methods exist to treat the symptoms of influenza virus infection, many are not alw

Method used

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  • Methods of treating influenza viral infections
  • Methods of treating influenza viral infections
  • Methods of treating influenza viral infections

Examples

Experimental program
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Effect test

preparation example Construction

[0119] Preparation of catecholbutane:

[0120] The catecholbutanes of the present invention can be prepared by any conventional method. For example, such compounds can be prepared as follows: U.S. Patent 5,008,294 (Jordan et al., issued April 16, 1991); U.S. Patent 6,291,524 (Huang et al., issued September 18, 2001); Hwu et al. (Hwu et al., "Antiviral activity of methylated nordihydroguaiaretic acids. 1. Synthesis, structural recognition, and inhibition of Tat-regulated HIV transactivation." Journal of Medicinal Chemistry ( J.Med.Chem) 4 / (16):2994-3000" (1998)); or McDonald et al., (McDonald, R.W. et al., Synthesis and Antibiotics of Dihydroguaiaretic Acid (NDGA) and Analogues Cancer activity." Anti-Cancer Drug Des., 16:261-270 (2001)).

[0121] In one embodiment of the invention, a catecholbutane, tetra-O-methyl NDGA, also known as meso-1,4-bis(3,4-dimethoxyphenyl)- 2,3-Dimethylbutane, terameprocol, EM-1421 or M4N (shown in the formula below) was prepared by preparing a re...

Embodiment 1

[0229] Catecholbutanes of general formula (I), ie M 4 Effect of N on TNF-α production by LPS-induced RAW 264.7 macrophages to determine M 4 N inhibits the ability of TNF-α induction. The effect of any catecholbutane of general formula (I) on the production of any pro-inflammatory cytokine in any LPS-stimulated macrophages can be determined using a method similar to that of this example.

[0230] As shown in Figure 1 and described below, M 4 N inhibited LPS-induced TNF-α overexpression in RAW 264.7 macrophages with a maximum inhibition of 57% at 10 h after induction.

[0231] More specifically, regarding the determination of M 4 N method to inhibit TNF-α induction by LPS, or leave 1.5 x 10 5 macrophages without treatment (control) or with LPS (1 μg / ml), M 4 N (25 μM) or both compounds were incubated at different time points. RAW 264.7 cells are mouse mononuclear macrophages. The LPS used was derived from Salmonella minnesota R595, which is available from List Biological ...

Embodiment 2

[0236] Catecholbutanes of general formula (I), ie M 4 Effect of N on TNF-α-induced apoptosis in murine fibroblasts to determine M 4 N inhibits the ability of TNF-α to induce apoptosis. The effect of any catecholbutane of general formula (I) on TNF-α-induced apoptosis in any type of cells can be determined using a method similar to that of this example.

[0237] Influenza infection induces the production of TNF-[alpha], and TNF-[alpha] pro-apoptotic activity is well known. Influenza viruses require apoptosis for efficient replication, and blocking TNF-α-induced apoptosis can reduce influenza virus replication and disease.

[0238] As shown in Figure 2 and described below, M4N strongly inhibited TNF-α-induced apoptosis in TNF-sensitive cells by cycloheximide. C3HA mouse fibroblasts in the absence / presence of NDGA (25 μM) or M 4 N (50 μM) was incubated with human recombinant TNF-α (20 ng / ml), cycloheximide (CHI) (10 ng / ml) or both. All compounds were added simultaneously and...

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Abstract

Methods are described for treating an influenza viral infection or associated diseases, disorders or mechanisms in a subject, comprising administering to the subject a therapeutically effective amount of a catecholic butane of the general formula (I) or a pharmaceutically acceptable salt thereof: wherein R1 and R2 each independently represents a hydrogen, a lower alkyl, a lower acyl, an alkylene, or -OR1 and -OR2 each independently represents an unsubstituted or substituted amino acid residue or pharmaceutically acceptable salt thereof; R3, R4, R5, R6, R10, R11, R12 and R13 each independently represents a hydrogen, or a lower alkyl; and R7, R8 and R9 each independently represents a hydrogen, -OH, a lower alkoxy, a lower acyloxy, an unsubstituted or substituted amino acid residue or pharmaceutically acceptable salt thereof, or any two adjacent groups together may be an alkyene dioxy; with the proviso in certain circumstances that where one of R7, R8 and R9 represents a hydrogen, then -OR1, -OR2 and the other two of R7, R8 and R9 do not simultaneously represent -OH.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of U.S. Provisional Application No. 60 / 775,869, filed February 23, 2006, and U.S. Provisional Application No. 60 / 776,043, filed February 23, 2006, the disclosures of which are hereby incorporated by reference in their entirety. included in this application. Background technique [0003] Influenza viruses are a major source of infection for a variety of diseases, causing severe cold symptoms and often respiratory disorders and / or pneumonia, which can be fatal. According to the serotypes of nucleoproteins and membrane proteins, influenza viruses are classified into three types, ie, A, B, and C. Among these types of influenza viruses, the types that circulate each year are influenza virus A and influenza virus B. Influenza virus A has two glycoproteins on the surface of its envelope, namely hemagglutinin (HA) and neuraminidase (NA), and based on this it is divided into subtypes accordin...

Claims

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Application Information

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IPC IPC(8): A61K31/00A61K31/03A61K31/045A61K31/05
Inventor 乔纳森·丹尼尔·赫勒斯科特·马修·拉斯特罗西奥·亚历杭德雷·洛佩斯尼尔·弗雷泽
Owner ERIMOS PHARMA
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