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Claims for Patent: 6,503,745

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Claims for Patent: 6,503,745

Title: Cyclopentane and cyclopentene compounds and use for detecting influenza virus
Abstract:New cyclopentane and cyclopentene compounds are provided along with their use in method for detecting influenza virus.
Inventor(s): Chand; Pooran (Birmingham, AL), Babu; Yarlagadda S. (Birmingham, AL), Bantia; Shanta (Birmingham, AL)
Assignee: Biocryst Pharmaceuticals, Inc. (Birmingham, AL)
Application Number:09/831,140
Patent Claims: 1. A compound selected from the group represented by the following formula: ##STR7##

wherein: U is CH; Z is --CH--CH(R.sub.3)nR.sub.2 ; R.sub.1 is H; R.sub.9 is (CH.sub.2)nCO.sub.2 H, (CH.sub.2)nSO.sub.3 H, (CH.sub.2)nPO.sub.3 H.sub.2, (CH.sub.2)nNO.sub.2, esters thereof, or salts thereof; R.sub.2 is NHC(O)R.sub.5, NHC(S)R.sub.5, or NHSO.sub.2 R.sub.5 ; R.sub.3 is H, (CH.sub.2)nCO.sub.2 R.sub.10, (CH.sub.2)mOR.sub.10, C(O)N(R.sub.10)m, (CH.sub.2)nN(R.sub.10)m, CH(R.sub.10)m, (CH.sub.2)n(R.sub.10)m, CH.sub.2 CH(OR.sub.10)CH.sub.2 OR.sub.10, CH(OR.sub.10)CH(OR.sub.10)CH.sub.2 OR.sub.10, CH.sub.2 OR.sub.10, CH(OR.sub.10)CH.sub.2 NHR.sub.10, CH.sub.2 CH(OR.sub.10)CH.sub.2 NHR.sub.10, CH(OR.sub.10)CH(OR.sub.10)CH.sub.2 NHR.sub.10, C(.dbd.NR.sub.10)N(R.sub.10)m, NHR.sub.10, NHC(.dbd.NR.sub.10)N(R.sub.10)m, (CH.sub.2)m-X--W--Y, CH.sub.2 CH(X--W--Y)CH.sub.2 OR.sub.10, CH(X--W--Y)CH(OR.sub.10)CH.sub.2 OR.sub.10, CH(X--W--Y)CH.sub.2 (OR.sub.10), CH(OR.sub.10)CH(X--W--Y)CH.sub.2 OR.sub.10, CH(OR.sub.10)CH.sub.2 (X--W--Y), CH.sub.2 CH(X--W--Y)CH.sub.2 NHR.sub.10, CH(X--W--Y)CH(OR.sub.10)CH.sub.2 NHR.sub.10, CH(X--W--Y)CH.sub.2 (NHR.sub.10), CH(OR.sub.10)CH(X--W--Y)CH.sub.2 NHR.sub.10, or CH(NHR.sub.10)CH.sub.2 (X--W--Y); R.sub.4 is (CH.sub.2)nOH, (CH.sub.2)nNR.sub.10 R.sub.11, (CH.sub.2)nNH.sub.2, (CH.sub.2)nC(.dbd.NH)(NH.sub.2), (CH.sub.2)nNHC(.dbd.NR.sub.11)NH.sub.2, (CH.sub.2)nNHC(.dbd.NR.sub.7)NH.sub.2, (CH.sub.2)nCN, (CH.sub.2)nN.sub.3, C(.dbd.NH)NH.sub.2, C(NR.sub.7)NH.sub.2, or C(NR.sub.11)NH.sub.2 ; R.sub.5 is H, lower alkyl, branched chain alkyl, cyclic alkyl, halogen substituted alkyl, aryl, substituted aryl, or CF.sub.3 ; R.sub.7 is H, (CH.sub.2)nOH, (CH.sub.2)nCN, (CH.sub.2)nNH.sub.2, or (CH.sub.2)nNO.sub.2 ; R.sub.10 is H, lower alkyl, lower alkylene, branched alkyl, cyclic alkyl, (CH.sub.2)n aromatic, (CH.sub.2)n substituted aromatic, or when m is 2 both R.sub.10 groups can also be interconnected to form an N substituted heterocyclic ring, or other 5 or 6 membered heterocyclic ring; R.sub.11 is lower alkyl, branched alkyl, (CH.sub.2)m aromatic, or C(O)OR.sub.10 ; R.sub.12 is (CH.sub.2)nOH, (CH.sub.2)nNH.sub.2, (CH.sub.2)nNR.sub.10 R.sub.11, (CH.sub.2)nOR.sub.11, (CH.sub.2)nF, (CH.sub.2)nOC(O)R.sub.11, (CH.sub.2)nNHC(O)R.sub.11, or X--W--Y; R.sub.13 is H or R.sub.12 ; m is 1 or 2; n is 0-4; p is 1; X is O, S, CH.sub.2, or NH; W is a spacer group made up of a chain of 4 to 100 atoms, and optionally also comprising of substituted carbon and/or nitrogen atoms and optionally including oxygen or sulphur atoms; Y is OH, SH, NH.sub.2, CH.dbd.O, CH.dbd.CH.sub.2, CO.sub.2 H, CONHNH.sub.2, or NH-biotinyl, or a protected form of one of these end functionalities.

2. A method of detecting influenza virus, comprising the step of exposing a sample suspected to comprise influenza virus to at least one compound according to claim 1, wherein the at least one compound is capable of binding specifically to the active site of influenza virus neuraminidase.

3. The method of claim 2 wherein the at least one compound is attached to a support material such that virus particles will be selectively captured and concentrated when a sample is passed over or through the support.

4. The method of claim 2 wherein the at least one compound is linked via a spacer group to a surface.

5. The method of claim 4 wherein the spacer group terminates in a functionality able to bind to a surface.

6. The method of claim 5 wherein the terminal functionality is a biotinyl group and the surface is coated with avidin, streptavidin, or an antibody directed against biotin.

7. The method of claim 5 wherein the terminal functionality is an amino group and the surface comprises carboxy groups.

8. The method of claim 2 wherein the at least one compound is linked to a detectable label.

9. The method of claim 8 wherein the detectable label is covalently coupled to-the at least one compound.

10. The method of claim 8 wherein the virus particles in a sample are exposed to the at least one compound coupled to a detectable label, under conditions such that the at least one compound binds selectively to the viral neuraminidase on the surface of the viral particle.

11. The method of claim 8 which comprises the steps of selective capture and~concentration of the virus.

12. The method of claim 2 comprising the step of selective capture and selective detection of influenza virus.

13. The method of claim 12 comprising the steps of: a) exposing the sample to a neuraminidase binder bound to a support, and b) exposing influenza virus particles retained on the support to the at least one compound.

14. The method of claim 2 in which the at least one compound has an IC.sub.50 for binding of less than 10 .mu.M.

15. The compound of claim 1 represented by the formula: ##STR8## R.sub.1 =H; R.sub.9 =CO.sub.2 H; R.sub.4 =NH.sub.2, or NHC(.dbd.NH)NH.sub.2 ; Z=CH--CH(NHCOCH.sub.3)-1-ethyl-propyl; U=CH; P=1: R.sub.12 =X--W--Y; W=A--B; X is O; A is --C(O)NH; B is (CH.sub.2).sub.6, (CH.sub.2).sub.6 NHCONH(CH.sub.2).sub.6, (CH.sub.2 CH.sub.2 O).sub.2 CH.sub.2 CH.sub.2, (CH.sub.2).sub.6 (NHCOCH.sub.2).sub.3, (CH.sub.2).sub.6 NHCO(CH.sub.2).sub.11, (CH.sub.2).sub.6 NHCO(CH.sub.2).sub.6 [NHCO(CH.sub.2).sub.5 ].sub.4, CH.sub.2).sub.6 [NHCO(CH.sub.2).sub.5 ]NHCOCH.sub.2 (OCH.sub.2 CH.sub.2).sub.16, (CH.sub.2).sub.6 [NHCO(CH.sub.2).sub.5 ].sub.2, (CH.sub.2).sub.6 [NHCO(CH.sub.2).sub.5 ].sub.4 NH--COCH.sub.2 CH.sub.2, or (CH.sub.2).sub.6 NHCOCH.sub.2 CH.sub.2 ; Y is NH.sub.2, NH-Biotin, CONHNHBoc, NHBoc, CONHNH.sub.2, or CO.sub.2 H.

16. The compound of claim 2 wherein R.sub.12 is OC(O)NH(CH.sub.2).sub.6 NH.sub.2 and R.sub.4 is NH.sub.2.

17. The compound of claim 2 wherein R.sub.2 is OC(O)NH(CH.sub.2).sub.6 NH.sub.2 and R.sub.4 is NHC(.dbd.NH)NH.sub.2.

18. The compound of claim 2 wherein R.sub.12 is OC(O)NH(COH.sub.2 CH.sub.2 O).sub.2 CH.sub.2 H.sub.2 NH.sub.2 and R.sub.4 is NH.sub.2.

19. The compound of claim 2 wherein R.sub.12 is OC(O)NH(CH.sub.2).sub.6 NH-Biotin and R.sub.4 is NH.sub.2.

20. The compound of claim 2 wherein R.sub.12 is OC(O)NH(CH.sub.2).sub.6 (NHCOCH.sub.2).sub.3 NH-Biotin and R.sub.4 is NH.sub.2.

21. The compound of claim 2 wherein R.sub.12 is OC(O)NH(CH.sub.2).sub.6 NHCO(CH.sub.2).sub.11 NH-Biotin and R.sub.4 is NH.sub.2.

22. The compound of claim 2 wherein R.sub.12 is OC(O)NH(CH.sub.2).sub.6 NHCO(CH.sub.2).sub.5 --NH-Biotin and R.sub.4 is NH.sub.2.

23. The compound of claim 2 wherein R.sub.12 is OC(O)NH(CH.sub.2).sub.6 [NHCO(CH.sub.2).sub.5 ].sub.4 NH.sub.2 and R.sub.4 is NH.sub.2.

24. The compound of claim 2 wherein R.sub.12 is OC(O)NH(CH.sub.2).sub.6 [NHCO(CH.sub.2).sub.5 ].sub.4 NH-Biotin and R.sub.4 is NH.sub.2.

25. The compound of claim 2 wherein R.sub.12 is OC(O)NH(CH.sub.2).sub.6 [NHCO(CH.sub.2).sub.5 ].sub.4 NHC(O)CH.sub.2 CH.sub.2 C(O)NHNH.sub.2 and R.sub.4 is NH.sub.2.

26. The compound of claim 2 wherein R.sub.12 is OC(O)NH(CH.sub.2).sub.6 NHCOCH.sub.2 CH.sub.2 CO.sub.2 H and R.sub.4 is NH.sub.2.

27. A method of detecting influenza virus, comprising the step of exposing a sample suspected to comprise influenza virus to at least one compound according to claim 15, wherein the at least one compound is capable of binding specifically to the active site of influenza virus neuraminidase.

28. The method of claim 15 wherein the at least one compound is attached to a support material such that virus particles will be selectively captured and concentrated when a sample is passed over or through the support.

29. The method of claim 28 wherein the at least one compound is linked via a spacer group to a surface.

30. The method of claim 29 wherein the spacer group terminates in a functionality able to bind to a surface.

31. The method of claim 30 wherein the terminal functionality is a biotinyl group and the surface is coated with avidin, streptavidin, or an antibody directed against biotin.

32. The method of claim 30 wherein the terminal functionality is an amino group and the surface comprises carboxy groups.

33. The method of claim 15 wherein the at least one compound is linked to a detectable label.

34. The method of claim 33 wherein the detectable label is covalently coupled to the at least one compound.

35. The method of claim 33 wherein the virus particles in a sample are exposed to the at least one compound coupled to a detectable label, under conditions such that the at least one compound binds selectively to the viral neuraminidase on the surface of the viral particle.

36. The method of claim 33 which comprises the steps of selective capture and concentration of the virus.

37. The method of claim 15 comprising the step of selective capture and selective detection of influenza virus.

38. The method of claim 37 comprising the steps of: a) exposing the sample to a neuraminidase binder bound to a support, and b) exposing influenza virus particles retained on the support to the at least one compound.

39. The method of claim 15 in which the at least one compound has an IC.sub.50 for binding of less than 10 .mu.M.
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