CA2464572A1 - Transition metal complexes with (pyridyl)imidazole ligands - Google Patents
Transition metal complexes with (pyridyl)imidazole ligands Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/002—Osmium compounds
- C07F15/0026—Osmium compounds without a metal-carbon linkage
Abstract
Novel transition metal complexes of iron, cobalt, ruthenium, osmium, and vanadium are described. The transition metal complexes can be used as redox mediators in enzyme-based electrochemical sensors. The transition metal complexes include substituted or unsubstituted (pyridyl)imidazole ligands.
Transition metal complexes attached to polymeric backbones are also described.
Transition metal complexes attached to polymeric backbones are also described.
Claims (48)
1. A transition metal complex having the formula:
wherein c is a negative, neutral, or positive charge represented by -1 to -5, 0, or +1 to +S, respectively;
d is an absence or a number of counter ions X represented by 0 or 1 to 5, respectively;
M is cobalt, iron, osmium, ruthenium, or vanadium;
L1 is a substituted or an unsubstituted heterocyclic nitrogen-containing ligand;
L2 is a negatively charged ligand; and L and L' are independently selected from a group consisting of:
wherein R'1 is a substituted or an unsubstituted alkyl, alkenyl, or aryl;
R a and R b are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl;
R'3, R'4 are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of R'3 and R'4 forms a saturated or unsaturated 5- or 6-membered ring; and Rc, and Rd are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of Rc and Rd forms a saturated or unsaturated 5- or 6-membered ring.
wherein c is a negative, neutral, or positive charge represented by -1 to -5, 0, or +1 to +S, respectively;
d is an absence or a number of counter ions X represented by 0 or 1 to 5, respectively;
M is cobalt, iron, osmium, ruthenium, or vanadium;
L1 is a substituted or an unsubstituted heterocyclic nitrogen-containing ligand;
L2 is a negatively charged ligand; and L and L' are independently selected from a group consisting of:
wherein R'1 is a substituted or an unsubstituted alkyl, alkenyl, or aryl;
R a and R b are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl;
R'3, R'4 are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of R'3 and R'4 forms a saturated or unsaturated 5- or 6-membered ring; and Rc, and Rd are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of Rc and Rd forms a saturated or unsaturated 5- or 6-membered ring.
2. The complex of claim l, wherein R'1 is a substituted or unsubstituted C1-C12 alkyl or alkenyl.
3. The complex of claim 1, wherein R'1 is methyl.
4. The complex of claim l, wherein R'1 is a substituted or unsubstituted aryl.
5. The complex of claim l, wherein R'1 is a substituted or unsubstituted phenyl.
6. The complex of claim 1, wherein R'1 is a phenyl substituted with a substituent selected from a group consisting of -Cl, -F, -CN, amino, carboxy, alkyl, C1-C6 alkylthio, C1-C6 alkylamino, C1-C6 dialkylamino, C1-C6 alkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, and C1-C6 alkylcarboxamido.
7. The complex of claim 1, wherein R'3, R'4, Ra, Rb, Rc, and Rd are independently -H or substituted or unsubstituted alkyl.
8. The complex of claim 1, wherein c is 0, +l, +2, or +3.
9. The complex of claim 1, wherein X is an anion selected from a group consisting of halides, sulfates, phosphates, hexafluorophosphates and tetrafluoroborates.
10. The complex of claim 1, wherein X is chloride.
11. The complex of claim 1, wherein d is 2.
12. The complex of claim 1, . wherein L1 is a derivative of any of imidazole, triazole, oxazole, thiazole, and pyrazole.
13. The complex of claim 1, wherein L1 has the formula:
wherein R7 is a substituted or an unsubstituted alkyl, alkenyl, or aryl;
R8 is -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxyamino, alkylthio, alkenyl, aryl, or alkyl; and R9 and R10 are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNHZ, -SH, -OH, -NH2, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxyamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of R9 and R10 forms a fused, saturated or unsaturated, 5- or 6-membered ring.
wherein R7 is a substituted or an unsubstituted alkyl, alkenyl, or aryl;
R8 is -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxyamino, alkylthio, alkenyl, aryl, or alkyl; and R9 and R10 are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNHZ, -SH, -OH, -NH2, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxyamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of R9 and R10 forms a fused, saturated or unsaturated, 5- or 6-membered ring.
14. The complex of claim 13, wherein R7 is a substituted or unsubstituted C1-C12 alkyl or alkenyl.
15. The complex of claim 13, wherein R9 and R10 form a fused, unsaturated 6-membered ring.
16. The complex of claim 13, wherein R8, R9 and R10 are independently -H
or substituted or unsubstituted alkyl.
or substituted or unsubstituted alkyl.
17. The complex of claim 1, wherein L1 has the formula:
wherein R11, R12, R13, R14 and R15 are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -OH, -NH2, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxyamino, alkylthio, alkenyl, aryl, or alkyl.
wherein R11, R12, R13, R14 and R15 are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -OH, -NH2, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxyamino, alkylthio, alkenyl, aryl, or alkyl.
18. The complex of claim 17, wherein at least one of R11, R12, R13, R14 and R15 is an alkyl substituted with -F, -Cl, -Br, -I, alkylamino, dialkylamino, trialkylammonium, alkoxy, alkylthio, aryl, or a reactive group, or an aryl substituted with -F, -Cl, -Br, -I, alkylamino, dialkylamino, alkoxy, alkylthio, aryl, or a reactive group.
19. The complex of claim ,17, wherein R11, R12, R13, R14 and R15 are independently -H, methyl, C1-C2 alkoxy, C1-C2 alkylamino, C2-C4 dialkylamino, or a C1-C6 alkyl substituted with a reactive group.
20. The complex of claim 1, wherein L2 is selected from a group consisting of -CN, -SCN, -OH, halide, alkoxy, alkylthio, and phenoxide.
21. The complex of claim 1, wherein LZ is chloride.
22. The complex of claim 1 having a redox potential of from about 0 mV
to about -200 mV relative to a Ag/AgCI reference electrode.
to about -200 mV relative to a Ag/AgCI reference electrode.
23. The complex of claim 1, wherein M is osmium.
24. The complex of claim 1, wherein at least one of L, L', L1 and L2 is coupled to a polymeric backbone.
25. The complex of claim 24, wherein the polymeric backbone comprises at least one functional group that is a ligand of the complex.
26. The complex of claim 25, wherein the functional group is selected from a group consisting of pyridine and imidazole groups.
27. The complex of claim 1, wherein said complex is a polymeric product of a reaction of a precursor polymer and a precursor transition metal complex.
28. A transition metal complex having the formula:
wherein c is a neutral or positive charge represented by 0, or +1 to +3, respectively;
d is absence or a number of counter anions X represented by 0 or 1 to 5, respectively;
M is osmium;
L1 is a substituted or an unsubstituted heterocyclic nitrogen-containing ligand;
L2 is from a group consisting of -CN, -SCN, -OH, halide, alkoxy, alkylthio, and phenoxide; and L and L' are independently selected from a group consisting of wherein R'1 is a substituted or an unsubstituted C1-C12 alkyl; and R'3, R'4, Ra, Rb, Rc, and Rd are independently -H or substituted or unsubstituted alkyl.
wherein c is a neutral or positive charge represented by 0, or +1 to +3, respectively;
d is absence or a number of counter anions X represented by 0 or 1 to 5, respectively;
M is osmium;
L1 is a substituted or an unsubstituted heterocyclic nitrogen-containing ligand;
L2 is from a group consisting of -CN, -SCN, -OH, halide, alkoxy, alkylthio, and phenoxide; and L and L' are independently selected from a group consisting of wherein R'1 is a substituted or an unsubstituted C1-C12 alkyl; and R'3, R'4, Ra, Rb, Rc, and Rd are independently -H or substituted or unsubstituted alkyl.
29. The complex of claim 28, wherein X is an anion selected from a group consisting of halides, sulfates, phosphates, hexafluorophosphates and tetrafluoroborates.
30. The complex of claim 28, wherein L2 is selected from a group consisting of -CN, -SCN, -OH, halide, alkoxy, alkylthio, and phenoxide.
31. The complex of claim 28, wherein L1 is a derivative of any of imidazole, triazole, oxazole, thiazole, and pyrazole.
32. The complex of claim 28, wherein L1 has the formula:
wherein R7 is a substituted or an unsubstituted C1-C12 alkyl or alkenyl; and R8, R9 and R10 are independently -H or substituted or unsubstituted alkyl.
wherein R7 is a substituted or an unsubstituted C1-C12 alkyl or alkenyl; and R8, R9 and R10 are independently -H or substituted or unsubstituted alkyl.
33. The complex of claim 28, wherein L1 has the formula:
wherein R11, R12, R13, R14 and R15 are independently -H, methyl, C1-C2 alkoxy, C1-C2 alkylamino, C2-C4 dialkylamino, or a C1-C6 alkyl substituted with a reactive group.
wherein R11, R12, R13, R14 and R15 are independently -H, methyl, C1-C2 alkoxy, C1-C2 alkylamino, C2-C4 dialkylamino, or a C1-C6 alkyl substituted with a reactive group.
34. The complex of claim 28 having a redox potential of from about 0 mV
to about -200 mV relative to a Ag/AgCI reference electrode.
to about -200 mV relative to a Ag/AgCI reference electrode.
35. The complex of claim 28, wherein at least one of L, L', L1 and L2 is coupled to a polymeric backbone.
36. The complex of claim 35, wherein the polymeric backbone comprises at least one functional group that is a ligand of the complex.
37. The complex of claim 36, wherein the functional group is selected from a group consisting of pyridine and imidazole groups.
38. The complex of claim 28, wherein said complex is a polymeric product of a reaction of a precursor polymer and a precursor transition metal complex.
39. A sensor comprising:
a working electrode;
a counter electrode;
a redox mediator disposed proximate to the working electrode, the redox mediator having the formula:
wherein c is a negative, neutral, or positive charge represented by -1 to -5, 0, or +1 to +5, respectively;
d is an absence or a number of counter ions X represented by 0 or 1 to 5, respectively;
M is cobalt, iron, osmium, ruthenium, or vanadium;
L1 is a substituted or an unsubstituted heterocyclic nitrogen-containing ligand;
L2 is a negatively charged ligand; and L and L' are independently selected from a group consisting of:
wherein R'1 is a substituted or an unsubstituted alkyl, alkenyl, or aryl;
Ra and Rb are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl;
R'3, R'4 are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of R'3 and R'4 forms a saturated or unsaturated 5- or 6-membered ring; and R c, and R d are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of R c and R d forms a saturated or unsaturated 5- or 6-membered ring.
a working electrode;
a counter electrode;
a redox mediator disposed proximate to the working electrode, the redox mediator having the formula:
wherein c is a negative, neutral, or positive charge represented by -1 to -5, 0, or +1 to +5, respectively;
d is an absence or a number of counter ions X represented by 0 or 1 to 5, respectively;
M is cobalt, iron, osmium, ruthenium, or vanadium;
L1 is a substituted or an unsubstituted heterocyclic nitrogen-containing ligand;
L2 is a negatively charged ligand; and L and L' are independently selected from a group consisting of:
wherein R'1 is a substituted or an unsubstituted alkyl, alkenyl, or aryl;
Ra and Rb are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl;
R'3, R'4 are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of R'3 and R'4 forms a saturated or unsaturated 5- or 6-membered ring; and R c, and R d are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl, or a combination of R c and R d forms a saturated or unsaturated 5- or 6-membered ring.
40. The sensor of claim 39, wherein c is a neutral or positive charge represented by 0, or +1 to +3, respectively; M is osmium; L2 is selected from a group consisting of -CN, -SCN, -OH, halide, alkoxy, alkylthio, and phenoxide; R'1 is a substituted or an unsubstituted C1-C12 alkyl; and R'3, R'4, R a, R b, R c, and R d are independently -H or substituted or unsubstituted alkyl groups.
41. The sensor of claim 39, further comprising an enzyme disposed proximate to the working electrode.
42. The sensor of claim 39, wherein the redox mediator has a redox potential of from about 0 mV to about -200 mV relative to a Ag/AgCl reference electrode.
43. The sensor of claim 39, wherein the redox mediator is coupled to a polymeric backbone via at least one of L, L', L1 and L2.
44. The sensor of claim 43, wherein the polymeric backbone comprises at least one functional group that is a ligand of the complex.
45. The sensor of claim 44, wherein the functional group is selected from a group consisting of pyridine and imidazole groups.
46. The sensor of claim 39, wherein said complex is a polymeric product of a reaction of a precursor polymer and a precursor transition metal complex.
47. The sensor of claim 39, wherein the redox mediator is crosslinked on the working electrode.
48. The sensor of claim 39, wherein the redox mediator and an enzyme are crosslinked on the working electrode.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29053701P | 2001-05-11 | 2001-05-11 | |
| US60/290,537 | 2001-05-11 | ||
| US10/143,300 | 2002-05-09 | ||
| US10/143,300 US6676816B2 (en) | 2001-05-11 | 2002-05-09 | Transition metal complexes with (pyridyl)imidazole ligands and sensors using said complexes |
| PCT/US2002/014918 WO2004009604A2 (en) | 2001-05-11 | 2002-05-10 | Transition metal complexes with (pyridyl)imidazole ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2464572A1 true CA2464572A1 (en) | 2004-01-29 |
| CA2464572C CA2464572C (en) | 2012-05-01 |
Family
ID=26840895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2464572A Expired - Lifetime CA2464572C (en) | 2001-05-11 | 2002-05-10 | Transition metal complexes with (pyridyl)imidazole ligands |
Country Status (8)
| Country | Link |
|---|---|
| US (5) | US6676816B2 (en) |
| EP (2) | EP2301942B1 (en) |
| JP (1) | JP4420899B2 (en) |
| CN (1) | CN1620462B (en) |
| AT (1) | ATE520701T1 (en) |
| AU (1) | AU2002367975B2 (en) |
| CA (1) | CA2464572C (en) |
| WO (1) | WO2004009604A2 (en) |
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| US7918976B2 (en) | 1999-11-15 | 2011-04-05 | Abbott Diabetes Care Inc. | Transition metal complexes with bidentate ligand having an imidazole ring |
| US8092662B2 (en) | 1999-11-15 | 2012-01-10 | Abbott Diabetes Care Inc. | Redox polymers |
| US8168052B2 (en) | 1999-11-15 | 2012-05-01 | Abbott Diabetes Care Inc. | Transition metal complexes with bidentate ligand having an imidazole ring |
| US8268143B2 (en) | 1999-11-15 | 2012-09-18 | Abbott Diabetes Care Inc. | Oxygen-effect free analyte sensor |
| US8512534B2 (en) | 1999-11-15 | 2013-08-20 | Abbott Diabetes Care Inc. | Redox polymers |
| US8795490B2 (en) | 1999-11-15 | 2014-08-05 | Abbott Diabetes Care Inc. | Redox polymers |
| US8828204B2 (en) | 1999-11-15 | 2014-09-09 | Abbott Diabetes Care Inc. | Redox polymers |
| US9320467B2 (en) | 1999-11-15 | 2016-04-26 | Abbott Diabetes Care Inc. | Redox polymers |
| US10219730B2 (en) | 1999-11-15 | 2019-03-05 | Abbott Diabetes Care Inc. | Redox polymers |
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| US7074308B2 (en) | 2006-07-11 |
| JP4420899B2 (en) | 2010-02-24 |
| US20060149067A1 (en) | 2006-07-06 |
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| ATE520701T1 (en) | 2011-09-15 |
| US20030096997A1 (en) | 2003-05-22 |
| US20040099529A1 (en) | 2004-05-27 |
| CA2464572C (en) | 2012-05-01 |
| US20090143584A1 (en) | 2009-06-04 |
| US8298388B2 (en) | 2012-10-30 |
| WO2004009604A3 (en) | 2004-11-25 |
| US20100038242A1 (en) | 2010-02-18 |
| US6676816B2 (en) | 2004-01-13 |
| CN1620462B (en) | 2011-02-02 |
| CN1620462A (en) | 2005-05-25 |
| EP1507785B1 (en) | 2011-08-17 |
| EP2301942A1 (en) | 2011-03-30 |
| EP2301942B1 (en) | 2017-12-13 |
| US7615637B2 (en) | 2009-11-10 |
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