CA2387779A1 - Isoalloxazine derivatives to neutralize biological contaminants - Google Patents

Isoalloxazine derivatives to neutralize biological contaminants Download PDF

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CA2387779A1
CA2387779A1 CA002387779A CA2387779A CA2387779A1 CA 2387779 A1 CA2387779 A1 CA 2387779A1 CA 002387779 A CA002387779 A CA 002387779A CA 2387779 A CA2387779 A CA 2387779A CA 2387779 A1 CA2387779 A1 CA 2387779A1
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group
compound
hydrogen
chlorine
bromine
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CA2387779C (en
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Matthew Stewart Platz
Raymond Paul Goodrich Jr.
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Terumo BCT Biotechnologies LLC
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/0005—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts
    • A61L2/0011—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts using physical methods
    • A61L2/0029—Radiation
    • A61L2/0076—Radiation using a photocatalyst or photosensitiser
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/0005—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts
    • A61L2/0082—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts using chemical substances
    • A61L2/0088—Liquid substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
    • A61L2/08—Radiation
    • A61L2/10—Ultra-violet radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D475/00—Heterocyclic compounds containing pteridine ring systems
    • C07D475/12—Heterocyclic compounds containing pteridine ring systems containing pteridine ring systems condensed with carbocyclic rings or ring systems
    • C07D475/14—Benz [g] pteridines, e.g. riboflavin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
    • A61L2202/20—Targets to be treated
    • A61L2202/22—Blood or products thereof

Abstract

Methods are provided for neutralization of microorganisms in fluids or on surfaces. Preferably the fluids contain blood or blood products and comprise biologically active proteins. Preferred methods include the steps of adding an activation-effective amount of a microorganism neutralizer with an isoalloxazine backbone to a fluid and exposing the fluid to a triggering event. Preferred triggering events include light of a suitable wavelength an d intensity to activate the microorganism neutralizer or a pH sufficient to activate the microorganism neutralizer. Other fluids, including juices, wate r and the like, may also be decontaminated by these methods as may surfaces of foods, animal carcasses, wounds, food preparation surfaces and bathing and washing vessel surfaces. Compounds with an isoalloxazine backbone are also provided.

Claims (69)

1. A method for treating a fluid to neutralize microorganisms which may be present therein, said fluid containing one or more components selected from the group consisting of protein, blood, and blood constituents, said method comprising:
(a) adding to said fluid a neutralization-effective amount of a microorganism neutralizer of formula:
wherein R1, R2, R3, R4, R5 and R6 are, independently from one another, selected from the group consisting of hydrogen, optionally substituted hydrocarbyl, alcohol, amine, polyamine, sulfate, phosphate, halogen selected from the group consisting of chlorine, bromine and iodine, salts of the foregoing, and -NR a-(CR b R c)n-X
wherein X
is a halogen selected from the group consisting of chlorine, bromine and iodine, R a, R b and R c are, independently of each other, selected from the group consisting of hydrogen, optionally substituted hydrocarbyl, and halogen selected from the group consisting of chlorine, bromine and iodine, and n is an integer from 0 to 20;
provided that R1 is not -OH or a straight chain alkyl group where the second carbon of the chain is substituted with -OH or =O and R1, R4, R5 are not all methyl groups when R2, R3 and R6 are hydrogen;
(b) exposing the fluid of step (a) to a triggering event whereby said microorganisms are neutralized.
2. The method of claim 1, wherein R1, R2, R3, R4, R5 and R6 are, independently from one another, selected from the group consisting of hydrogen, optionally substituted alcohol, straight chain or cyclic saccharide, amino acid, amine, polyamine, polyether, polyalcohol, sulfate, phosphate, carbonyl, glycol, halogen selected from the group consisting of chlorine, bromine and iodine, aldehyde, ketone, carboxylic acid and ascorbate.
3. The method of claim 1, wherein said triggering event is photoradiation sufficient to activate the microorganism neutralizer.
4. The method of claim 1, wherein said triggering event is a pH sufficient to activate the microorganism neutralizer.
5. The method of claim 4, wherein said pH is between about 5 and about 8.
6. The method of claim 1 wherein said microorganisms are selected from the group consisting of bacteria, bacteriophages, and intracellular and extracellular viruses.
7. The method of claim 1 wherein said microorganisms are bacteria.
8. The method of claim 1, wherein said microorganisms are selected from the group consisting of HIV viruses, hepatitis viruses, sindbis virus, cytomegalovirus, vesicular stomatitis virus, herpes simplex viruses, vaccinia virus, human T-lymphotropic retroviruses, HTLV-III, lymphadenopahy virus LAV/IDAV, parvovirus, transfusion-transmitted (TT) virus, Epstein-Barr virus, bacteriophages ~X174, ~6, .lambda., R17, T4, T2, P. aeruginosa, S. aureus, S. epidermidis, L. monocytogenes, E. coli, K.
pneumoniae and S. marcescens.
9. The method of claim 1, wherein said microorganism neutralizer is wherein R is selected from the group consisting of ascorbate, alcohol, polyalcohol, amine, polyamine, straight chain or cyclic saccharides, sulfates, phosphates, polyethylene glycols, and polyethers.
10. The method of claim 1, wherein said microorganism neutralizer is wherein X is a halogen selected from the group consisting of chlorine, bromine and iodine, R a, R b and R c are, independently of each other, selected from the group consisting of hydrogen, optionally substituted hydrocarbyl, and halogen selected from the group consisting of chlorine, bromine and iodine, and n is an integer from 0 to 20.
11. The method of claim 1 , wherein said microorganism neutralizer is wherein W is a water soluble group.
12. The method of claim 1, wherein said fluid comprises blood constituents.
13. The method of claim 1, wherein said fluid comprises whole blood.
14. The method of claim 1, wherein said fluid comprises a separated blood product.
15. The method of claim 1, wherein said fluid comprises platelets separated from whole blood.
16. The method of claim 1, wherein said fluid comprises red blood cells separated from whole blood.
17. The method of claim 1, wherein said fluid comprises serum separated from whole blood.
18. The method of claim 1, wherein said fluid comprises plasma separated from whole blood.
19. The method of claim 1, wherein said fluid comprises a therapeutic protein composition.
20. The method of claim 1, wherein said fluid contains a biologically-active protein selected from the group consisting of factor VIII, Von Willebrand factor, factor IX, factor X, factor XI, Hageman factor, prothrombin, anti-thrombin III, fibronectin, plasminogen, plasma protein fraction, peritoneal dialysis solutions, immune serum globulin, modified immune globulin, albumin, plasma growth hormone, somatomedin, plasminogen streptokinase complex, ceruloplasmin, transferrin, haptoglobin, antitrypsin and prekallikrein.
21. The method of claim 1, wherein said microorganism neutralizer is added to anticoagulant and said anticoagulant is added to said fluid.
22. The method of claim 1, wherein an enhancer is added to said fluid prior to exposing said fluid to said triggering event.
23. The method of claim 22, wherein said enhancer is selected from the group consisting of adenine, histidine, cysteine, tyrosine, tryptophan, ascorbate, N-acetyl-L-cysteine, propyl gallate, glutathione, mercaptopropionylglycine, dithiothreotol, nicotinamide, BHT, BHA, lysine, serine, methionine, glucose, mannitol, trolox, glycerol, and mixtures thereof.
24. The method of claim 1 , wherein if said microorganism neutralizer produces photolytic products, the photolytic products are of low or no toxicity to humans or animals.
25. A method for treating a fluid to neutralize microorganisms which may be present therein, said method comprising:
(a) adding to said fluid an neutralization-effective amount of a microorganism neutralizer of formula:
wherein R1, R2, R3, R4, R5 and R6 are, independently from one another, selected from the group consisting of hydrogen, optionally substituted hydrocarbyl, alcohol, amine, polyamine, sulfate, phosphate, halogen selected from the group consisting of chlorine, bromine and iodine, salts of the foregoing;
and -NR a-(CR b R c)n-X wherein X is a halogen selected from the group consisting of chlorine, bromine and iodine, R a, R b and R c are, independently of each other, selected from the group consisting of hydrogen, optionally substituted hydrocarbyl, and halogen selected from the group consisting of chlorine, bromine and iodine, and n is an integer from 0 to 20; provided that R1 is not -OH or a straight chain alkyl group where the second carbon of the chain is substituted with -OH or =O and R1, R4, are not all methyl groups when R2, R3 and R6 are all hydrogen;

(b) exposing the fluid of step (a) to a triggering event whereby said microorganisms are neutralized.
26. The method of claim 25, wherein R1, R2, R3, R4, R5 and R6 are, independently from one another, selected from the group consisting of hydrogen; optionally substituted alcohol, polyalcohol, straight chain or cyclic saccharide, amino acid, ether, polyether, amine, polyamine, sulfate, phosphate, carbonyl, glycol, halogen selected from the group chlorine, bromine and iodine, aldehyde, ketone, carboxylic acid and ascorbate.
27. The method of claim 25, wherein said fluid is a food product.
28. The method of claim 25, wherein said fluid is a drink meant for human or animal consumption.
29. The method of claim 25, wherein said fluid is a peritoneal dialysis solution.
30. A method of neutralizing microorganisms on a surface, comprising:
(a) applying to said surface an neutralization-effective amount of a compound of formula:
wherein R1, R2, R3, R4, R5 and R6 are, independently from one another, selected from the group consisting of hydrogen, optionally substituted hydrocarbyl, alcohol, amine, polyamine, sulfate, phosphate, halogen selected from the group consisting of chlorine, bromine and iodine, salts of the foregoing;

and -NR a-(CR b R c)n-X wherein X is a halogen selected from the group consisting of chlorine, bromine and iodine, R a, R b and R c are, independently of each other, selected from the group consisting of hydrogen, optionally substituted hydrocarbyl, and halogen selected from the group consisting of chlorine, bromine and iodine, and n is an integer from 0 to 20;
provided that R1 is not -OH or a straight chain alkyl group where the second carbon of the chain is substituted with -OH or =O and R1, R4, R5 are not all methyl groups when R2, R3 and R6 are all hydrogen;
(b) exposing said surface to a triggering event whereby said microorganisms are neutralized
31. The method of claim 30, wherein R1, R2, R3, R4, R5 and R6 are, independently from one another, selected from the group consisting of hydrogen; optionally substituted alcohol, polyalcohol, straight chain or cyclic saccharide, amino acid, ether, polyether, amine, polyamine, sulfate, phosphate, carbonyl, glycol, halogen selected from the group chlorine, bromine and iodine, aldehyde, ketone, carboxylic acid and ascorbate.
32. The method of claim 30, wherein said surface is a food surface.
33. The method of claim 30, wherein said surface is the surface of an animal carcass.
34. The method of claim 30, wherein said surface is a food-preparation surface.
35. The method of claim 30, wherein said surface is a surface of a bathing or washing vessel.
36. The method of claim 30, wherein said surface is a wound surface.
37. A fluid comprising biologically active protein, blood or blood constituents, and microorganism neutralizer, made by the method of claim 1.
38. A blood product comprising a microorganism neutralizer, made by the method of claim 1.
39. A compound having the structure:
wherein R1, R2, R3, R4, R5 and R6 are, independently from one another, selected from the group consisting of hydrogen, optionally substituted hydrocarbyl, alcohol, amine, polyamine, sulfate, phosphate, halogen selected from the group consisting of chlorine, bromine and iodine, salts of the foregoing;
and -NR a-(CR b R c)n-X wherein X is a halogen selected from the group consisting of chlorine, bromine and iodine, R a, R b and R c are, independently of each other, selected from the group consisting of hydrogen, optionally substituted hydrocarbyl, and halogen selected from the group consisting of chlorine, bromine and iodine, and n is an integer from 0 to 20;
provided that R1 is not -OH or a straight chain alkyl group where the second carbon of the chain is substituted with -OH or =O; and R1 is not a 2-, 3-, 4- or 5-carbon straight chain alkyl that terminates in -OH, -COH, or -H when R2, R3 and R6 are H, and R4 and R5 are CH3; R1 is not - CH2CH2-(CHOH)2-CH3 or -CH2CH2-(CHOH)2 -CH2SO4 or 1'-D-sorbityl or 1'-D-dulcityl or 1'-D-rhamnityl or 1'-D,L-glyceryl or -CH2-O-C(O)-CH3 or -CH2-O-C(O)-CH2CH3 or 2', 3', 4', S'-di-O-isopropyridene-riboflavin or 8-aminooctyl when R2, R3 and R6 are H and R4 and R5 are CH3; R1 is not 1'-D-sorbityl or 1'-D-dulcityl when R4 and R5 are both chlorines and when R2, R3 and R6 are all hydrogens; R5 is not ethyl or chloro when R1 and R4 are methyl and R2, R3 and R6 are all hydrogens; R4 and R5 are not both methoxy or both tetramethylene when R1 is methyl and R2, R3 and R6 are all hydrogens; R2 is not -CH2CH2NH when R1, R4 and R5 are CH3 and R3 and R6 are H; R2 is not when R1, R4 and R5 are CH3 and R3 and R6 are H; R5 is not chloro when R4 is methoxy and R1 is ethyl-2'N-pyrrolidino and R2, R3, and R6 are hydrogen; R1 is not N,N-dimethylaminopropyl or N,N-diethylaminoethyl when R5 is chloro or methyl and R2, R3, R4 and R6 are hydrogen; R3 is not -NH(CH2CH2)C1 when R6 is -NH2 and R1, R2, R4 and R5 are H; R1, R4, R5 are not all methyl groups when all of R2, R3 and R6 are hydrogens; R1, R4, R5 and R2 are not all methyl groups when R3 and R6 are hydrogens; R2 is not carboxymethyl when R1, R4 and R5 are methyl and R3 and R6 are hydrogen; R4 is not -NH2 when R1 and R5 are methyl and R2, R3 and are all hydrogen; R1 is not a phenyl group when R4 and R5 are methyl and R2, and R6 are all H; R1 is not methyl or N,N-dimethylaminoethyl when all of R2, R3, R4, R5 and R6 are hydrogen; R2, R4, R5 are not all methyl when R1 is acetoxyethyl and R3 and R6 are hydrogen; R5 is not methyl when R1 is N,N-diethylaminoethyl and R2, R3, R4 and R6 are all hydrogen; R4 and R5 are not both chlorine when R1 is methyl and R2, R3 and R6 are all hydrogen; R1 is not ethyl, .beta.-chloroethyl, n-butyl, anilino, benzyl, phenyl, p-tolyl or p-anisyl when R5 is NH2 and R2, R3, R4 and are all hydrogen; and R4 is not chlorine when R1 is N,N-dimethylaminopropyl and R2, R3, R5 and R6 are all hydrogen.
40. The compound of claim 39, wherein a plurality of R1, R2, R3, R4, R5 and R6 are neither CH3 nor H.
41. The compound of claim 40, wherein a plurality of R2, R3, R4, R5 and R6 are neither H nor CH3.
42. The compound of claim 40, wherein a R1, R2, R3, R4, R5 and R6 that is neither CH3 nor H imparts substantial water solubility to the compound.
43. The compound of claim 42, wherein said R1, R2, R3, R4, R5 and R6 is selected from the group consisting of:
alcohols; polyalcohols; straight chain or cyclic saccharides; ether;
polyether; amines;
polyamines; sulfate groups; phosphate groups; ascorbate groups; alkyl chains optionally substituted with -OH at any position; glycols; and polyethers.
44. The compound of claim 43, wherein R1 is not CH2-(CH2OH)3-CH2OH.
45. The compound of claim 43, wherein R1 is -CH2-(CH2OH)3-CH2OH.
46. The compound of claim 43, wherein R3 and R6 are H.
47. The compound of claim 40, wherein at least one of R1, R2, R3, R4, R5 and contains a halogen selected from the group consisting of chlorine, bromine and iodine.
48. The compound of claim 47, wherein at least one of R1, R2, R3, R4, R5 and R6 is -(CH2)n-X, wherein n is either 1 or 2, and X is a halogen selected from the group consisting of chlorine, bromine and iodine.
49. The compound of claim 47, wherein at least one of the halogenated R1, R2, R3, R4, R5 and R6 is -NR(CH2)n-X, wherein R is hydrogen or straight chain alkyl group consisting of one to 6 carbon atoms, n is an integer from 0 to 6, and X is selected from the group consisting of chlorine, bromine and iodine.
50. The compound of claim 49 wherein R4 or R5 is -NR(CH2)n-X, wherein R is hydrogen or straight chain alkyl group consisting of one to 6 carbon atoms, n is an integer from 0 to 6, and X is selected from the group consisting of chlorine, bromine and iodine.
51. The compound of claim 39, wherein one of R1, R2, R3, R4, R5 and R6 is neither CH3 nor H.
52. The compound of claim 51, wherein the R1, R2, R3, R4, R5 and R6 that is neither CH3 nor H imparts substantial water solubility to the compound.
53. The compound of claim 52, wherein the R1, R2, R3, R4, R5 and R6 is selected from the group consisting of:
alcohols; polyalcohols; straight chain or cyclic saccharides; amines and polyamines;
sulfate groups; phosphate groups; ascorbate groups; alkyl chains optionally substituted with -OH at any position; glycols; ethers and polyethers.
54. The compound of claim 53, wherein R1 is not CH2-(CH2OH)3-CH2OH.
55. The compound of claim 53, wherein the R1, R2, R3, R4, R5 and R6 that is neither H
nor CH3 is R2, R3, R4, R5 or R6.
56. The compound of claim 53, wherein R3 and R6 are H.
57. The compound of claim 51, wherein one of R1, R2, R3, R4, R5 and R6 is halogenated, wherein the halogen is selected from the group consisting of chlorine, bromine and iodine.
58. The compound of claim 57, wherein one of R1, R2, R3, R4, R5 and R6 is -(CH2)n-X, wherein n is either 1 or 2, X is a halogen selected from the group consisting of chlorine, bromine and iodine.
59. The compound of claim 57, wherein one of R1, R2, R3, R4, R5 and R6 is -NR(CH2)n-X, wherein R is hydrogen or straight chain alkyl group consisting of one to 6 carbon atoms, n is an integer from 0 to 6, and X is selected from the group consisting of chlorine, bromine and iodine.
60. The compound of claim 59 wherein R4 or R5 is -NR(CH2)n-X, wherein R is hydrogen or straight chain alkyl group consisting of one to 6 carbon atoms, n is an integer from 0 to 6, and X is selected from the group consisting of chlorine, bromine and iodine.
61. The compound of claim 39 wherein at least one of R1, R2, R3, R4, R5 and R6 are branched or unbranched C1 to C20 alkyl groups substituted with at least one -OH
group.
62. The compound of claim 39 having the structure:

wherein R is selected from the group consisting of ascorbate, alcohol, polyalcohol, amine or polyamines, straight chain or cyclic saccharides, sulfates, phosphates, polyethylene glycols and polyethers.
63. The compound of claim 39 having the structure wherein R is selected from the group consisting of hydrogen and optionally substituted straight chain or branched alkyl having from 1 to 20 carbon atoms.
64. The compound of claim 39 having the structure wherein R is selected from the group consisting of hydrogen and optionally substituted straight chain or branched alkyl having from 1 to 20 carbon atoms.
65. The compound of claim 39, having the structure:

wherein W is a water soluble group.
66. The compound of claim 39 wherein at least one of R1, R2, R3, R4, R5 and R6 are alkylating agents.
67. The compound of claim 39 wherein at least one of R1, R2, R3, R4, R5 and R6 are substituents that cause the compound to be substantially nonreactive to microorganisms at substantially neutral pH and active toward microorganism neutralization at the pH of the biological fluid.
68. A method of making a compound having structure:

wherein W is a water soluble group, comprising:
(a) photolyzing carboxyriboflavin;
(b) reacting (a) with oxallylchloride;
(c) reacting (b) with a member of the group consisting of ascorbate, glucosamine, protected glucose derivatives, diethylene glycol and triethylene glycol.
69. A method of making a compound having the structure:

where W is a water soluble group, comprising:
(a) contacting with sodium azide;

(b) reacting (a) with and POCl3.

(c) reacting (b) with a water solubilizing group.
CA2387779A 1999-10-19 2000-09-15 Isoalloxazine derivatives to neutralize biological contaminants Expired - Fee Related CA2387779C (en)

Applications Claiming Priority (3)

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US09/420,652 1999-10-19
US09/420,652 US6268120B1 (en) 1999-10-19 1999-10-19 Isoalloxazine derivatives to neutralize biological contaminants
PCT/US2000/025213 WO2001028599A1 (en) 1999-10-19 2000-09-15 Isoalloxazine derivatives to neutralize biological contaminants

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AT (1) ATE299713T1 (en)
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US6268120B1 (en) 2001-07-31
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ATE299713T1 (en) 2005-08-15
US20010024781A1 (en) 2001-09-27
EP1221982A1 (en) 2002-07-17
AU7580700A (en) 2001-04-30
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EP1221982B1 (en) 2005-07-20
CA2387779C (en) 2010-10-12

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