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Last Updated: April 19, 2024

Details for Patent: 7,956,197


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Title:Compounds, compositions and methods for treatment and prevention of orthopoxvirus infections and associated diseases
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 caused by the orthopoxvirus.
Inventor(s): Jordan; Robert (Corvallis, OR), Bailey; Thomas R. (Phoenixville, PA), Rippin; Susan R. (Wilmington, DE)
Assignee: Siga Technologies, Inc. (New York, NY)
Filing Date:Apr 01, 2010
Application Number:12/752,462
Claims:1. A method of making 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocy- cloprop[f]isoindol-2(1H)-yl)-benzamide, said method comprising: a) reacting 4-trifloromethylbenzhydrazide with a compound of formula ##STR00055## in a solvent to form a reaction product; and b) collecting 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocy- cloprop[f]isoindol-2(1H)-yl)-benzamide.

2. The method of claim 1, wherein the ratio of compound 1(a) to 4-trifloromethylbenzhydrazide is 0.89 to 1.

3. The method of claim 1 wherein the solvent is ethanol.

4. The method of claim 1 wherein the reaction occurs at above room temperature.

5. The method of claim 1 wherein the reaction occurs under argon.

6. The method of claim 1 wherein the solvent is removed by evaporation.

7. The method of claim 1 wherein 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocy- cloprop[f]isoindol-2(1H)-yl)-benzamide is further purified by chromatography.

8. A method of making 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocy- cloprop[f]isoindol-2(1H)-yl)-benzamide, said method comprising: a) reacting cycloheptatriene and maleic anhydride in a first solvent to form compound 1(a); ##STR00056## b) collecting compound 1(a); c) reacting 4-trifloromethylbenzhydrazide with said compound 1(a) in a second solvent to form 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-- ethenocycloprop[f]isoindol-2(1H)-yl)-benzamide; and d) collecting 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocy- cloprop[f]isoindol-2(1H)-yl)-benzamide.

9. The method of claim 8, wherein said first solvent comprises xylenes.

10. The method of claim 8, wherein said second solvent is ethanol.

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