1. A compound represented by structural formula I
the pyridyl-N-oxide analog of formula I, and the pharmaceutically acceptable salts, esters and solvates thereof wherein:
R1 is selected from the group consisting of:
R2 is selected from the group consisting of (a) \u2014C1-6alkyl optionally substituted with 1-3 of fluoro, (b) \u2014C3-6 cycloalkyl and
n is an integer selected from 0, 1, 2 and 3;
R3 is selected from the group consisting of \u2014H, \u2014F, \u2014OH, \u2014CH3 and \u2014CF3;
R4 is selected from the group consisting of \u2014H and \u2014C1-4alkyl;
R5 is selected from the group consisting of \u2014H and \u2014CH3; and
R6 is selected from the group consisting of \u2014H, \u2014C1-6alkyl optionally substituted with 1-3 fluoro, \u2014C3-6 cycloalkyl optionally substituted with 1-3 fluoro and \u2014CH2\u2014R10;
R7 is selected from the group consisting of \u2014H, \u2014C1-6alkyl optionally substituted with 1-3 fluoro, \u2014C3-6 cycloalkyl optionally substituted with 1-3 fluoro, \u2014COC1-6alkyl and \u2014COC3-6cycloalkyl;
R8 is selected from the group consisting of \u2014H, \u2014C1-6alkyl optionally substituted with 1-3 fluoro, and \u2014C3-6 cycloalkyl optionally substituted with 1-3 fluoro;
R9 is selected from the group consisting of \u2014CH3 and \u2014F; and
R10 is selected from the group consisting of pyrrolidinyl optionally substituted on nitrogen with methyl, piperidinyl optionally substituted on nitrogen with methyl, and morpholinyl optionally substituted on nitrogen with methyl.
2. The compound of claim 1 wherein:
R1 is selected from the group consisting of:
R2 is selected from the group consisting of (a) \u2014C1-6alkyl optionally substituted with 1-3 fluoro, (b) \u2014C3-6 cycloalkyl and
n is an integer selected from 0, 1, 2 and 3;
R3 is selected from the group consisting of \u2014H, \u2014F, \u2014OH, \u2014CH3 and \u2014CF3;
R4 is selected from the group consisting of \u2014H and \u2014C1-4alkyl;
R5 is selected from the group consisting of \u2014H and \u2014CH3; and
R6 is selected from the group consisting of \u2014H and \u2014C1-3alkyl.
3. The compound of claim 1 wherein R1 is
4. The compound of claim 3 wherein R2 is \u2014C1-6alkyl optionally substituted with 1-3 fluoro.
5. The compound of claim 3 wherein R2 is selected from \u2014C3-6 cycloalkyl and
6. The compound of claim 4 wherein R3 is selected from \u2014H, \u2014OH and methyl.
7. The compound of claim 6 wherein R4 is selected from \u2014H, methyl and ethyl.
8. The compound of claim 1 wherein R1 is selected from the group consisting of:
9. The compound of claim 8 wherein R2 is \u2014C1-6alkyl optionally substituted with 1-3 fluoro.
10. The compound of claim 8 wherein R2 is selected from \u2014C3-6 cycloalkyl and
11. The compound of claim 9 wherein R3 is selected from \u2014H, \u2014OH and methyl.
12. The compound of claim 11 wherein R4 is selected from \u2014H, methyl and ethyl.
13. The compound of claim 1 selected from the group consisting of those of the following structural formula wherein R2, R3, R4 and R5 are defined as follows:
R2
R3
R4
R5
t-Bu
H
H
H
Me
H
H
H
Et
H
H
H
Pr
H
H
H
i-Pr
H
H
H
Cyclopropyl
H
H
H
Cyclobutyl
H
H
H
Cyclopentyl
H
H
H
Cyclohexyl
H
H
H
H
H
H
H
H
H
Me
Me
H
H
Et
Me
H
H
i-Pr
Me
H
H
t-Bu
Me
H
H
Cyclopropyl
Me
H
H
Cyclobutyl
Me
H
H
Me
H
H
Me
H
H
t-Bu
H
Et
H
i-Pr
H
Et
H
Cyclopropyl
H
Et
H
Cyclobutyl
H
Et
H
H
Et
H
H
Et
H
i-Pr
Me
Et
H
t-Bu
Me
Et
H
i-Pr
H
Me
H
t-Bu
H
Me
H
Cyclopropyl
H
Me
H
Cyclobutyl
H
Me
H
H
Me
H
H
Me
H
i-Pr
Me
Me
H
t-Bu
Me
Me
H
t-Bu
H
Me
Me
i-Pr
H
Me
Me
t-Bu
H
Me
Me
Cyclopropyl
H
Me
Me
Cyclobutyl
H
Me
Me
H
Me
Me
H
Me
Me
t-Bu
Me
Me
Me
the pyridyl-N-oxide analogs thereof, and the pharmaceutically acceptable salts, esters and solvates thereof.
14. The compound of claim 1 selected from the group consisting of those of formula Id and formula Ie wherein R2, R3 and R6 are defined as follows:
Id
Ie
Compound No.
Id
Ie
R2
R3
R6
2g)
2g)
i-Pr
H
Me
2h)
2h)
Cyclopropyl
H
Me
2i)
2i)
Cyclobutyl
H
Me
2j)
2j)
H
Me
2k)
2k)
H
Me
2l)
2l)
i-Pr
Me
Me
2m)
2m)
t-Bu
Me
Me
2n)
2n)
Cyclopropyl
Me
Me
2o)
2o)
Cyclobutyl
Me
Me
2p)
2p)
Me
Me
2q)
2q)
Me
Me
2r)
2r)
i-Pr
H
Et
2s)
2s)
t-Bu
H
Et
2t)
2t)
Cyclopropyl
H
Et
2u)
2u)
Cyclobutyl
H
Et
2v)
2v)
H
Et
2w)
2w)
H
Et
2x)
2x)
i-Pr
Me
Et
2y)
2y)
t-Bu
Me
Et
2z)
2z)
Cyclopropyl
Me
Et
2aa)
2aa)
Cyclobutyl
Me
Et
2ab)
2ab)
Me
Et
2ac)
2ac)
Me
Et
2ad)
2ad)
i-Pr
H
i-Pr
2ae)
2ae)
t-Bu
H
i-Pr
2af)
2af)
Cyclobutyl
H
i-Pr
2ag)
2ag)
H
i-Pr
2ah)
2ah)
H
i-Pr
2ai)
2ai)
i-Pr
Me
i-Pr
2aj)
2aj)
t-Bu
Me
i-Pr
2ak)
2ak)
Cyclobutyl
Me
i-Pr
2al)
2al)
Me
i-Pr
2am)
2am)
Me
i-Pr
2an)
2an)
i-Pr
H
CHF2
2ao)
2ao)
t-Bu
H
CHF2
2ap)
2ap)
cyclobutyl
H
CHF2
2aq)
2aq)
H
CHF2
2ar)
2ar)
H
CHF2
2as)
2as)
i-Pr
Me
CHF2
2at)
2at)
t-Bu
Me
CHF2
2au)
2au)
i-Pr
H
2av)
2av)
t-Bu
H
2aw)
2aw)
cyclobutyl
H
2ax)
2ax)
H
2ay)
2ay)
H
2az)
2az)
i-Pr
Me
2ba)
2ba)
t-Bu
Me
2bb)
2bb)
i-Pr
H
2bc)
2bc)
t-Bu
H
2bd)
2bd)
cyclobutyl
H
2be)
2be)
H
2bf)
2bf)
H
2bg)
2bg)
i-Pr
Me
2bh)
2bh)
t-Bu
Me
2bi)
2bi)
i-Pr
H
2bj)
2bj)
t-Bu
H
2bk)
2bk)
cyclobutyl
H
2bl)
2bl)
H
2bm)
2bm)
H
2bn)
2bn)
i-Pr
Me
2bo)
2bo)
t-Bu
Me
2bp)
2bp)
i-Pr
H
2bq)
2bq)
t-Bu
H
2br)
2br)
cyclobutyl
H
2bs)
2bs)
H
2bt)
2bt)
H
2bu)
2bu)
i-Pr
Me
2bv)
2bv)
t-Bu
Me
2bw)
2bw)
i-Pr
H
2bx)
2bx)
t-Bu
H
2by)
2by)
cyclobutyl
H
2bz)
2bz)
H
2ca)
2ca)
H
2cb)
2cb)
i-Pr
Me
2cc)
2cc)
t-Bu
Me
the pyridyl-N-oxide analogs thereof, and the pharmaceutically acceptable salts, esters and solvates thereof.
15. The compound of claim 1 selected from the group consisting of:
5-(4-{2,2-dimethyl-1-4-(pyridin-2-ylmethoxy)phenylpropyl}phenyl)-1,3,4-oxadiazol-2-amine;
5-(4-{cyclopropyl4-(pyridin-2-ylmethoxy)phenylmethyl}phenyl)-1,3,4-oxadiazol-2-amine;
5-(4-{cyclobutyl4-(pyridin-2-ylmethoxy)phenylmethyl}phenyl)-1,3,4-oxadiazol-2-amine;
5-(4-{(1-methylcyclopropyl)4-(pyridin-2-ylmethoxy)phenylmethyl}phenyl)-1,3,4-oxadiazol-2-amine;
5-(4-{(1-methylcyclobutyl)4-(pyridin-2-ylmethoxy)phenylmethyl}phenyl)-1,3,4-oxadiazol-2-amine;
5-(4-{1,2-dimethyl-1-4-(pyridin-2-ylmethoxy)phenylpropyl}phenyl)-1,3,4-oxadiazol-2-amine;
5-(4-{2,2-dimethyl-1-4-(1-pyridin-2-ylpropoxy)phenylpropyl}phenyl)-1,3,4-oxadiazol-2-amine;
5-(4-{2,2-dimethyl-1-4-(1-methyl-1-pyridin-2-ylethoxy)phenylpropyl}phenyl)-1,3,4-oxadiazol-2-amine;
2-(4-{2,2-dimethyl-1-4-(2-methyl-2H-tetrazol-5-yl)phenylpropyl}-phenoxy)methylpyridine;
2-(4-{2,2-dimethyl-1-4-(1-methyl-1H-tetrazol-5-yl)phenylpropyl}phenoxy)methylpyridine;
2-(4-{1,2-dimethyl-1-4-(1-methyl-1H-tetrazol-5-yl)phenylpropyl}phenoxy)methylpyridine;
2-(4-{1,2-dimethyl-1-4-(2-methyl-2H-tetrazol-5-yl)phenylpropyl}phenoxy)methylpyridine;
2-(4-{1-4-(1-ethyl-1H-tetazol-5-yl)phenyl-2,2-dimethylpropyl}phenoxy)methylpyridine;
2-(4-{1-4-(2-ethyl-2H-teazol-5-yl)phenyl-2,2-dimethylpropyl}phenoxy)methylpyridine;
2-(4-{1-4-(1-ethyl-1H-tetrazol-5-yl)phenyl-1,2-dimethylpropyl}phenoxy)methylpyridine;
2-(4-{1-4-(2-ethyl-2H-tetrazol-5-yl)phenyl-1,2-dimethylpropyl}phenoxy)methylpyridine;
the pyridyl-N-oxide analogs thereof; and the pharmaceutically acceptable salts, esters and solvates thereof.
16. A pharmaceutical composition comprised of a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
17. The pharmaceutical composition of claim 15 further comprising an additional active agent which is an anti-atherosclerotic agent.
18. A method of treating atherosclerosis comprising administering a therapeutically effective amount of a compound of claim 1 to a patient in need of such treatment.
19. A method for preventing or reducing the risk of developing atherosclerosis, comprising administering a prophylactically effective amount of a compound of claim 1 to a patient at risk for developing atherosclerosis.
20. A method for preventing or reducing the risk of an atherosclerotic disease event comprising administering a prophylactically effective amount of a compound of claim 1 to a patient at risk for having an atherosclerotic disease event.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
What is claimed is:
1. A tamper-indicating radio frequency identification device, comprising:
a substrate including a first major surface and a second major surface opposite the first major surface; and
a radio frequency identification antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder.
2. The tamper-indicating radio frequency identification device of claim 1, wherein the antenna responds to a signal, and wherein after the tamper-indicating radio frequency identification antenna is bent equal to or less than a radius of 25 mm, the tamper-indicating radio frequency identification antenna does not respond to the signal.
3. The tamper-indicating radio frequency identification device of claim 2, wherein the signal is sent a distance greater than 15 cm from the tamper-indicating radio frequency identification antenna.
4. The tamper-indicating radio frequency identification device of claim 1, wherein the antenna is readable by an interrogator, and wherein after the tamper-indicating radio frequency identification antenna is bent equal to or less than a radius of 25 mm, the tamper-indicating radio frequency identification antenna is not readable by the interrogator.
5. The tamper-indicating radio frequency identification device of claim 4, wherein the interrogator is at distance greater than 15 cm from the antenna.
6. The tamper-indicating radio frequency identification device of claim 1, wherein the antenna includes a resistance, and wherein the resistance of the antenna increases when the antenna is bent equal to or less than a radius of 25 mm.
7. The tamper-indicating radio frequency identification device of claim 6, wherein the resistance of the antenna significantly increases when the antenna is bent equal to or less than a radius of 25 mm.
8. The tamper-indicating radio frequency identification device of claim 1, wherein the conductivity of the antenna is reduced when the antenna is bent equal to or less than a radius of 25 mm.
9. The tamper-indicating radio frequency identification device of claim 9, wherein the conductivity of the antenna is significantly reduced when the antenna is bent equal to or less than a radius of 25 mm.
10. The tamper-indicating radio frequency identification device of claim 1, wherein the antenna is conductive, and wherein the antenna is nonconductive after the antenna is bent equal to or less than a radius of 25 mm.
11. The tamper-indicating radio frequency identification device of claim 1, wherein after the antenna is bent equal to or less than a radius of 25 mm, the antenna comprises a fracture.
12. The tamper-indicating radio frequency identification device of claim 11, wherein the fracture is not visible to the naked eye.
13. The tamper-indicating radio frequency identification device of claim 1, wherein the antenna comprises a conductive pattern, and wherein the conductive pattern delaminates after the antenna is bent equal to or less than a radius of 25 mm.
14. The tamper-indicating radio frequency identification device of claim 1, wherein the substrate is selected from the group consisting of paper and materials that are at least about 10% compressible.
15. The tamper-indicating radio frequency identification device of claim 14, wherein the materials that are at least 10% compressible are selected from the group consisting of microporous materials, nonwoven materials and woven materials.
16. The tamper-indicating radio frequency identification device of claim 1, wherein the densified metal powder is selected from the group consisting of copper, tin, lead, silver, gold, platinum, aluminum, nickel, iron, steel, zinc and alloys and combinations thereof.
17. The tamper-indicating radio frequency identification device of claim 1, wherein the antenna is a loop antenna.
18. The tamper-indicating radio frequency identification device of claim 1, wherein the antenna is a dipole antenna.
19. The tamper-indicating radio frequency identification device of claim 1 further comprising a protective layer on the antenna.
20. A tamper-indicating radio frequency identification sticker, comprising:
a substrate including a first major surface and a second major surface opposite the first major surface; and
a radio frequency identification antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder;
a first integrated circuit attached to the antenna; and
a first layer of adhesive attached to the substrate.
21. The tamper-indicating radio frequency identification sticker of claim 20, wherein the first layer of adhesive is attached to the second major surface of the substrate.
22. The tamper-indicating radio frequency identification sticker of claim 20 further comprising a layer of retroreflective material including a first major surface and a second major surface opposite the first major surface, wherein the first major surface is attached to the first layer of adhesive.
23. The tamper-indicating radio frequency identification sticker of claim 22 further comprising a second layer of adhesive attached to the second major surface on of the layer of retroreflective material.
24. The tamper-indicating radio frequency identification sticker of claim 23 further comprising a liner on the second layer of adhesive.
25. The tamper-indicating radio frequency identification sticker of claim 20, wherein the first layer of adhesive is attached to the antenna.
26. The tamper-indicating radio frequency identification sticker of claim 25 further comprising a layer of retroreflective material including a first major surface and a second major surface opposite the first major surface, wherein the second major surface is attached to the first layer of adhesive.
27. The tamper-indicating radio frequency identification sticker of claim 22 further comprising a second layer of adhesive attached to the second major surface on of the layer of retroreflective material.
28. The tamper-indicating radio frequency identification sticker of claim 27 further comprising a liner on the second layer of adhesive.
29. The tamper-indicating radio frequency identification sticker of claim 20 further comprising a layer of retroreflective material attached adjacent to the sticker.
30. The tamper-indicating radio frequency identification sticker of claim 20 further comprising an indicia printed on the sticker.
31. The tamper-indicating radio frequency identification sticker of claim 20, wherein the first adhesive layer comprises a first adhesive portion and a second adhesive portion, wherein the first adhesive portion includes a first adhesion strength, wherein the second adhesive portion includes a second adhesive strength, and wherein the second adhesive strength is greater than the first adhesive strength.
32. The tamper-indicating radio frequency identification sticker of claim 20 further comprising a layer of tamper-indicating optical material attached to the sticker.
33. The tamper-indicating radio frequency identification sticker of claim 32, wherein the layer of tamper-indicating optical material includes a first major surface and a second major surface opposite the first major surface, and wherein the first layer of adhesive is attached to the second major surface of the substrate and is attached to the first major surface of the layer of tamper-indicating optical material.
34. The tamper-indicating radio frequency identification sticker of claim 32, wherein the layer of tamper-indicating optical material includes a first major surface and a second major surface opposite the first major surface, and wherein the first layer of adhesive is attached to the antenna and is attached to the second major surface of the layer of tamper-indicating optical material.
35. The tamper-indicating radio frequency identification sticker of claim 32, wherein after the sticker is removed from a surface, the layer of tamper-indicating optical material visibly indicates the sticker was removed from the surface.
36. The tamper-indicating radio frequency identification sticker of claim 20 further comprising
a second integrated circuit attached to the substrate, wherein the second integrated circuit includes an antenna.
37. The tamper-indicating radio frequency identification sticker of claim 36, wherein the second integrated circuit comprises a radio frequency identification antenna.
38. The tamper-indicating radio frequency identification sticker of claim 20, wherein the antenna responds to a signal, and wherein after the tamper-indicating radio frequency identification antenna is bent equal to or less than a radius of 25 mm, the tamper-indicating radio frequency identification antenna does not respond to the signal.
39. The tamper-indicating radio frequency identification sticker of claim 38, wherein the signal is sent from a distance greater than 15 cm.
40. The tamper-indicating radio frequency identification sticker of claim 20, wherein the antenna is readable by an interrogator, and wherein after the tamper-indicating radio frequency identification antenna is bent equal to or less than a radius of 25 mm, the tamper-indicating radio frequency identification antenna is not readable by the interrogator.
41. The tamper-indicating radio frequency identification sticker of claim 40, wherein the interrogator is at distance greater than 15 cm from the antenna.
42. The tamper-indicating radio frequency identification sticker of claim 20, wherein the antenna includes a resistance, and wherein the resistance of the antenna increases when the antenna is bent equal to or less than a radius of 25 mm.
43. The tamper-indicating radio frequency identification sticker of claim 43, wherein the resistance of the antenna is significantly increases when the antenna is bent equal to or less than a radius of 25 mm.
44. The tamper-indicating radio frequency identification sticker of claim 20, wherein the conductivity of the antenna is reduced when the antenna is bent equal to or less than a radius of 25 mm.
45. The tamper-indicating radio frequency identification sticker of claim 44, wherein the conductivity of the antenna is significantly reduced when the antenna is bent equal to or less than a radius of 25 mm.
46. The tamper-indicating radio frequency identification sticker of claim 45, wherein the antenna is conductive, and wherein the antenna is nonconductive after the antenna is bent equal to or less than a radius of 25 mm.
47. The tamper-indicating radio frequency identification sticker of claim 20, wherein after the antenna is bent equal to or less than a radius of 25 mm, the antenna comprises a fracture.
48. The tamper-indicating radio frequency identification sticker of claim 47, wherein the fracture is not visible to the naked eye.
49. The tamper-indicating radio frequency identification sticker of claim 20, wherein the antenna comprises a conductive pattern, and wherein the conductive pattern delaminates after the antenna is bent equal to or less than a radius of 25 mm.
50. A method of indicating a radio frequency identification sticker has been tampered, comprising the steps of:
attaching a tamper-indicating radio frequency identification sticker to a first surface, wherein the tamper-indicating radio frequency identification sticker, comprises:
a substrate including a first major surface and a second major surface opposite the first major surface;
a radio frequency identification antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder;
a first integrated circuit attached to the antenna; and
a first layer of adhesive attached to the substrate;
sending a signal to the tamper-indicating radio frequency identification sticker attached to the first surface;
receiving a response from the antenna;
removing the tamper-indicating radio frequency identification sticker from the first surface; and
sending the signal to the tamper-indicating radio frequency identification sticker and not receiving a response from the antenna.
51. The method of claim 50, wherein the removing step comprises bending the tamper-indicating radio frequency identification antenna less than a radius of 25 mm.
52. The method of claim 50, wherein the sending step comprises sending the signal from a distance greater than 15 cm from the tamper-indicating radio frequency identification sticker.
53. The method of claim 50, comprising after the removing step, the step of:
attaching the tamper-indicating radio frequency identification sticker to a second surface.
54. A method of indicating a radio frequency identification sticker has been tampered, comprising the steps of:
attaching a tamper-indicating radio frequency identification sticker to a first surface, wherein the tamper-indicating radio frequency identification sticker, comprises:
a substrate including a first major surface and a second major surface opposite the first major surface;
a radio frequency identification antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder;
a first integrated circuit attached to the antenna; and
a first layer of adhesive attached to the substrate;
measuring a first resistance in the antenna;
bending the tamper-indicating radio frequency identification sticker less than a radius of 25 mm; and
measuring a second resistance in the antenna that is higher than the first resistance of the antenna.
55. The method of claim 54, wherein the second resistance in the antenna is significantly higher than the first resistance of the antenna.
56. The method of claim 54 wherein the bending step comprises removing the tamper-indicating radio frequency identification sticker from the first surface.
57. The method of claim 56, further comprising, after the bending and removing step, the step of:
attaching the tamper-indicating radio frequency identification sticker to a second surface.
58. A method of indicating a radio frequency identification sticker has been tampered, comprising the steps of:
attaching a tamper-indicating radio frequency identification sticker to a first surface, wherein the tamper-indicating radio frequency identification sticker, comprises:
a substrate including a first major surface and a second major surface opposite the first major surface;
a radio frequency identification antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder;
a first integrated circuit attached to the antenna; and
a first layer of adhesive attached to the substrate;
measuring a first conductivity in the antenna;
bending the tamper-indicating radio frequency identification sticker less than or equal to a radius of 25 mm; and
measuring a second conductivity in the antenna that is lower than the first conductivity of the antenna.
59. The method of claim 58, wherein the second conductivity in the antenna is significantly lower than the first conductivity of the antenna.
60. The method of claim 58 wherein the bending step comprises removing the tamper-indicating radio frequency identification sticker from the first surface.
61. The method of claim 60, further comprising, after the bending and removing step, the step of:
attaching the tamper-indicating radio frequency identification sticker to a second surface.
62. A method of indicating a radio frequency identification sticker has been tampered, comprising the steps of:
attaching a tamper-indicating radio frequency identification sticker to a first surface, wherein the tamper-indicating radio frequency identification sticker, comprises:
a substrate including a first major surface and a second major surface opposite the first major surface;
a radio frequency identification antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder;
a first integrated circuit attached to the antenna; and
a first layer of adhesive attached to the substrate;
measuring a first conductivity in the antenna;
bending the tamper-indicating radio frequency identification sticker less than or equal to a radius of 25 mm; and
measuring a second conductivity that indicates that the antenna is nonconductive.
63. The method of claim 62 wherein the bending step comprises removing the tamper-indicating radio frequency identification sticker from the first surface.
64. The method of claim 63, further comprising, after the bending and removing step, the step of:
attaching the tamper-indicating radio frequency identification sticker to a second surface.
65. A method of indicating a radio frequency identification sticker has been tampered, comprising the steps of:
attaching a tamper-indicating radio frequency identification sticker to a first surface, wherein the tamper-indicating radio frequency identification sticker, comprises:
a substrate including a first major surface and a second major surface opposite the first major surface;
a radio frequency identification antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder;
a first integrated circuit attached to the antenna; and
a first layer of adhesive attached to the substrate;
bending the tamper-indicating radio frequency identification sticker less than or equal to a radius of 25 mm; and
forming a fracture in the radio frequency identification antenna.
66. The method of claim 65 wherein the bending step comprises removing the tamper-indicating radio frequency identification sticker from the first surface.
67. The method of claim 66, further comprising, after the bending and removing step, the step of:
attaching the tamper-indicating radio frequency identification sticker to a second surface.
68. A method of indicating a radio frequency identification sticker has been tampered, comprising the steps of:
attaching a tamper-indicating radio frequency identification sticker to a first surface, wherein the tamper-indicating radio frequency identification sticker, comprises:
a substrate including a first major surface and a second major surface opposite the first major surface;
a first radio frequency identification antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder;
a first integrated circuit attached to the antenna;
a second integrated circuit attached to the substrate, wherein the second integrated circuit comprises a second antenna; and
a first layer of adhesive attached to the substrate;
sending a signal to the tamper-indicating radio frequency identification sticker attached to the first surface;
receiving a response from the first antenna and from the second antenna;
removing the tamper-indicating radio frequency identification sticker from the first surface;
sending the signal to the tamper-indicating radio frequency identification sticker; and
receiving a signal from the second antenna and not receiving a response from the first antenna.
69. The method of claim 63, further comprising, after the removing step, the step of:
attaching the tamper-indicating radio frequency identification sticker to a second surface.
70. A tamper-indicating radio frequency identification sticker, comprising:
a substrate including a first major surface and a second major surface opposite the first major surface, wherein the substrate is selected from the group consisting of paper and materials that are at least about 10% compressible, and wherein the materials that are at least 10% compressible are selected from the group consisting of microporous materials, nonwoven materials and woven materials; and
a radio frequency identification loop antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder, wherein the densified metal powder is selected from the group consisting of copper, tin, lead, silver, gold, platinum, aluminum, nickel, iron, steel, zinc and alloys and combinations thereof; and wherein the metal powder comprises metal particles in the shape of spheres, oblongs, and polyhedra;
a first integrated circuit attached to the antenna; and
a first layer of adhesive attached to the substrate;
wherein the antenna responds to a signal sent a distance greater than 15 cm from the tamper-indicating radio frequency identification sticker, and wherein after the tamper-indicating radio frequency identification sticker is bent equal to or less than a radius of 25 mm, the tamper-indicating radio frequency identification loop antenna does not respond to the signal and the antenna comprises a fracture that is not visible to the naked eye.
71. A radio frequency identification antenna, comprising:
a substrate including a first major surface and a second major surface opposite the first major surface; and
a radio frequency identification antenna attached to the first major surface of the substrate, wherein said antenna comprises densified metal powder.
72. The radio frequency identification antenna of claim 71, wherein the substrate is selected from the group consisting of paper and materials that are at least about 10% compressible.
73. The radio frequency identification antenna of claim 72, wherein the materials that are at least 10% compressible are selected from the group consisting of microporous materials, nonwoven materials and woven materials.
74. The radio frequency identification antenna of claim 71, wherein the densified metal powder is selected from the group consisting of copper, tin, lead, silver, gold, platinum, aluminum, nickel, iron, steel, zinc and alloys and combinations thereof.
75. The radio frequency identification antenna of claim 71, wherein the antenna is a loop antenna.
76. The radio frequency identification antenna of claim 71, wherein the antenna is a dipole antenna.
77. The radio frequency identification antenna of claim 71 further comprising a protective layer on the antenna.
78. A radio frequency identification sticker comprising a radio frequency identification antenna of claim 71, and further comprising:
a first integrated circuit attached to the antenna; and
a first layer of adhesive attached to the substrate.
79. The A radio frequency identification sticker of claim 78, further comprising a layer of retroreflective material including a first major surface and a second major surface opposite the first major surface, wherein the second major surface is attached to the first layer of adhesive.