Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Chemicals, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases

A technology of orthopoxviruses and compounds, applied in the field of compositions containing it, can solve the problems of non-specific toxicity and limited use of compounds replicated by smallpox virus

Inactive Publication Date: 2010-05-05
SIGA TECH INC
View PDF4 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In conclusion, currently available compounds that inhibit variola virus replication are generally non-specific and loyal to toxicity limiting use and / or efficacy questionable

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Chemicals, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases
  • Chemicals, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases
  • Chemicals, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] Preparation of 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-vinylcyclopropane[f]iso Indol-2(1H)-yl)-benzamide ("ST-246")

[0099] a. Preparation of Compound 1(a).

[0100]

[0101] A mixture of cycloheptatriene (5 g, 54.26 mmol) and maleic anhydride (6.13 g, 62.40 mmol) in xylene (35 mL) was heated at reflux under argon overnight. The reaction was cooled to room temperature and the tan precipitate was collected by filtration and dried to give 2.94 g (28%) of the desired product.

[0102] b. Preparation of ST-246. A mixture of compound 1(a) (150 mg, 0.788 mmol) and 4-trifluoromethylbenzohydrazide (169 mg, 0.827 mmol) in ethanol (10 mL) was heated under argon overnight. The solvent was removed by rotary evaporation. Silica gel column chromatography using 1 / 1 hexane / ethyl acetate provided 152 mg (51%) of the product as a white solid.

Embodiment 2-14

[0104] Compounds of Examples 2-14 were synthesized following the general procedure of Example 1 above, using compound 1(a) and reacting it with the following hydrazide: isonicotinic acid hydrazide, 4-bromobenzohydrazide, 3 -Bromobenzohydrazide, 3-chlorobenzohydrazide, 2-bromobenzohydrazide, 2-chlorobenzohydrazide, 4-chlorobenzohydrazide, nicotinic acid hydrazide, 2-pyridinecarbohydrazide , 4-methoxybenzohydrazide, 4-nitrobenzohydrazide, 4-fluorobenzohydrazide and 3-fluorobenzohydrazide.

Embodiment 15

[0106] Preparation of 4-bromo-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethanocyclopropane[f]-isoindol Indol-2(1H)-yl)-benzamide

[0107] a. Preparation of compound 15(a).

[0108]

[0109] To a solution of compound 1(a) (1 g, 5.26 mmol) in ethanol (20 mL) was added 10% palladium on activated carbon (100 mg, 10 wt%). The mixture was shaken on a Parr hydrogenator under a hydrogen atmosphere of 50 psi for 3 hours. The mixture was filtered through a micron filter to remove palladium and the filtrate was concentrated to give 384 mg (38%) of the product as a white solid.

[0110] b. Preparation of 4-bromo-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethanocyclopropane[f]- Isoindol-2(1H)-yl)-benzamide. A mixture of compound 15(a) (350 mg, 1.82 mmol) and 4-bromobenzohydrazide (411 mg, 1.91 mmol) in ethanol (10 mL) was heated under argon for 48 hours. The solvent was removed by rotary evaporation. Silica gel column chromatography using 1 / 1 hexane / ethyl acetate as eluen...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Login to View More

Abstract

Methods of using di, tri, and tetracyclic acylhydrazide derivatives and analogs, as well as pharmaceutical compositions containing the same, for the treatment or prophylaxis of viral infections and diseases associated therewith, particularly those viral infections and associated diseases cased by the orthopoxvirus.

Description

[0001] This application is a continuation-in-part of U.S. Application No. 10 / 561,153, filed April 5, 2006, which claims priority to International Patent Application No. PCT / 2004 / 112718, filed June 18, 2004, which The International Patent Application claims priority to US Provisional Application No. 60 / 480,182, filed June 20, 2003. All priority applications are hereby incorporated by reference in their entirety for all purposes. technical field [0002] Described herein are bicyclic, tricyclic and tetracyclic acyl hydrazide derivatives and analogs, and compositions comprising them, for use in the treatment or prevention of viral infections and diseases associated therewith, particularly those caused by orthopoxviruses Infections and related diseases. Background technique [0003] The genus Orthopox (Orthopoxviridae) is a member of the Poxviridae family and the Chodopoxivirinae subfamily. The genus consists of many viruses that cause significant disease in humans and fauna. ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D209/56
CPCC07D209/56A61K9/1623A61K9/1652A61P31/12A61P31/20
Inventor 罗伯特·乔丹托阿斯·R·贝雷苏珊·R·里皮戴冬成
Owner SIGA TECH INC
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com