Claims for Patent: 8,466,177

Summary for Patent: 8,466,177

Title:	Treating and preventing viral infections
Abstract:	Compounds that are useful in treating or preventing viral infections, such as influenza, are described herein. Further described are compositions made from these compounds and methods for using the compounds and their compositions in treating or preventing viral infections.
Inventor(s):	Luo; Ming (Birmingham, AL), Yang; Zhen (Ridgewood, NJ)
Assignee:	The UAB Research Foundation (Birmingham, AL)
Application Number:	12/682,341
Patent Claims:	1. A compound of the following formula: ##STR00245## or a pharmaceutically acceptable salt or prodrug thereof, wherein: X is S or NH; Y is O or S; Z is selected from a substituted or unsubstituted 5-member heteroaryl ring, 6-member heteroaryl ring, or phenyl; R.sup.1 is selected from a substituted or unsubstituted aryl or heteroaryl ring; and L is --CH.sub.2-- or .dbd.CH--, wherein when X is S, R is selected from a substituted or unsubstituted fused or bicyclic cycloalkyl ring; and when X is NH, R is selected from a substituted or unsubstituted fused or bicyclic cycloalkyl ring or a substituted or unsubstituted cycloalkyl ring having 3 to 14 carbon ring atoms. 2. The compound of claim 1, wherein R is selected from octahydro-pentalenyl, octahydro-1H-indenyl, decahydronaphthalenyl, decahydroazulenyl, and decahydro-1H-benzo[7]annulenyl. 3. The compound of claim 1, wherein R is selected from bicyclo[1.1.0]-butanyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.1]heptanyl, bicyclo[3.1.1]heptanyl, bicyclo[2.2.2]octanyl, bicyclo-[3.2.1]octanyl, bicyclo[3.3.2]decanyl, and adamantyl. 4. The compound of claim 1, wherein Z is a substituted or unsubstituted 5-member heteroaryl ring. 5. The compound of claim 1, wherein Z is selected from substituted or unsubstituted furanyl, thiophenyl, pyrazolyl, pyrrolyl, thiazolyl, oxazolyl, or imidazolyl. 6. The compound of claim 1, wherein Z is a substituted or unsubstituted 6-member heteroaryl ring. 7. The compound of claim 1, wherein Z is selected from substituted or unsubstituted phenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazinyl, or triazinyl. 8. The compound of claim 1, wherein R.sup.1 has the formula: ##STR00246## wherein X and Y are each independently selected from CH and N, and R.sup.a represents up to 5 organic radicals, wherein the radicals are substitutions for hydrogen. 9. The compound of claim 1, wherein R.sup.1 is substituted by from 1 to 5 organic radicals independently selected from halogen; substituted or unsubstituted haloalkyl; substituted or unsubstituted C.sub.1-C.sub.12 alkyl; substituted or unsubstituted C.sub.2-C.sub.12 alkenyl; substituted or unsubstituted C.sub.2-C.sub.12 alkynyl; substituted or unsubstituted C.sub.5-C.sub.10 aryl; substituted or unsubstituted C.sub.1-C.sub.12 heteroalkyl, substituted or unsubstituted C.sub.1-C.sub.12 heteroalkenyl, substituted or unsubstituted C.sub.2-C.sub.12 heteroalkynyl; C.sub.1-C.sub.9 substituted or unsubstituted heterocyclic; C.sub.1-C.sub.11 substituted or unsubstituted heteroaryl; substituted or unsubstituted C.sub.1-C.sub.5 alkoxyalkyl; substituted or unsubstituted C.sub.2-C.sub.5 alkoxyalkenyl; substituted or unsubstituted C.sub.2-C.sub.5 alkoxyalkynyl; substituted or unsubstituted C.sub.1-C.sub.5 aminoalkyl; substituted or unsubstituted C.sub.2-C.sub.5 aminoalkenyl; substituted or unsubstituted C.sub.2-C.sub.5 aminoalkynyl; substituted or unsubstituted C.sub.1-C.sub.5 carboxyalkyl; substituted or unsubstituted C.sub.2-C.sub.5 carboxyalkenyl; substituted or unsubstituted C.sub.2-C.sub.5 carboxyalkynyl; substituted or unsubstituted C.sub.1-C.sub.5 amidoalkyl; substituted or unsubstituted C.sub.2-C.sub.5 amidoalkenyl; substituted or unsubstituted C.sub.2-C.sub.5 amidoalkynyl; substituted or unsubstituted C.sub.1-C.sub.5 cyanoalkyl; substituted or unsubstituted C.sub.2-C.sub.5 cyanoalkenyl; substituted or unsubstituted C.sub.2-C.sub.5 cyanoalkynyl; substituted or unsubstituted C.sub.1-C.sub.5 nitroalkyl; substituted or unsubstituted C.sub.2-C.sub.5 nitroalkenyl; substituted or unsubstituted C.sub.2-C.sub.5 nitroalkynyl; substituted or unsubstituted C.sub.1-C.sub.5 sulfonylalkyl; substituted or unsubstituted C.sub.2-C.sub.5 sulfonylalkenyl; substituted or unsubstituted C.sub.2-C.sub.5 sulfonylalkynyl; C.sub.1-C.sub.4 linear or branched haloalkyl; substituted or unsubstituted alkoxy; halogen; cyano; nitro; or substituted or unsubstituted amino. 10. The compound of claim 1, wherein X is NH and R is a monocyclic ring, a fused cycloalkyl ring, or a bicyclic ring. 11. The compound of claim 1, wherein X is NH and R is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclononyl, cyclodecyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclododecyl, and cycloundecyl. 12. A composition comprising one or more compounds of claim 1 and a pharmaceutically acceptable carrier. 13. A method for treating an influenza viral infection in a subject, the method comprising administering to the subject an effective amount of the compound of claim 1. 14. The method of claim 13, further comprising administering a second compound or composition, wherein the second compound or composition is an antiviral compound. 15. The method of claim 14 wherein the second compound or composition is a nucleoside or nucleotide reverse transcriptase inhibitor, a non-nucleoside reverse transcriptase inhibitor, a protease inhibitor, an integrase inhibitor, an RNA polymerase inhibitor, a DNA polymerase inhibitor, a kinase inhibitor, an enzyme inhibitor, an entry inhibitor, an assembly inhibitor, a maturation inhibitor, a M2 inhibitor, or a neuraminidase inhibitor. 16. The method of claim 15 wherein the second compound or composition is amantadine, rimantadine, oseltamivir, zanamivir, peramivir, raltegravir, maraviros, enfuviritide, bevirimat, VIVECON.RTM., abacavir, zidovudine, emtricitabine, lamivudine, didanosine, tenofovir disoproxil fumarate, COMBIVIR.RTM. (zidovudine+lamivudine), EPZICOM.RTM. (abacavir+lamivudine), TRIZIVIR.RTM. (abacavir+zidovudine+lamivudine), TRUVADA.RTM. (tenofovir disoproxil fumarate+emtricitabine), stavudine, racivir, amdoxovir, apricitabine, elvucitabine, alpha-epibromide, aldesleukin, HIV-1 Immunogen, BAY 50-4798, IR103, etravirine, delavirdine, efavirenz, nevirapine, rilpivirine, amprenavir, tipranavir, indinavir, saquinavir, lopinavir/ritonavir, fosamprenavir, ritonavir, darunavir, atazanavir, nelfinavir, enfuvirtide, maraviroc, vicriviroc, PRO140, TNX-355, raltegravir, elvitegravir, bevirimat, or hydroxyurea. 17. The method of claim 13, wherein the influenza viral infection is influenza A virus. 18. The method of claim 13, wherein the influenza viral infection is influenza B virus.

Details for Patent 8,466,177

Applicant	Tradename	Biologic Ingredient	Dosage Form	BLA	Approval Date	Patent No.	Expiredate
Clinigen, Inc.	PROLEUKIN	aldesleukin	For Injection	103293	05/05/1992		2027-11-01