AU2005277432B2 - 5-[3-(4-benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2, 4-dione and analogues as inhibitors of macrophage elastase - Google Patents
5-[3-(4-benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2, 4-dione and analogues as inhibitors of macrophage elastase Download PDFInfo
- Publication number
- AU2005277432B2 AU2005277432B2 AU2005277432A AU2005277432A AU2005277432B2 AU 2005277432 B2 AU2005277432 B2 AU 2005277432B2 AU 2005277432 A AU2005277432 A AU 2005277432A AU 2005277432 A AU2005277432 A AU 2005277432A AU 2005277432 B2 AU2005277432 B2 AU 2005277432B2
- Authority
- AU
- Australia
- Prior art keywords
- methoxyphenyl
- chlorophenyl
- methylphenyl
- compound
- mmp
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 102100027998 Macrophage metalloelastase Human genes 0.000 title claims abstract description 19
- 239000003112 inhibitor Substances 0.000 title abstract description 16
- ZUOUZWHAINARGI-UHFFFAOYSA-N 5-[3-(4-phenylmethoxyphenyl)sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=C(SC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=CO1 ZUOUZWHAINARGI-UHFFFAOYSA-N 0.000 title abstract description 4
- 108030001712 Macrophage elastases Proteins 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 29
- 101710187853 Macrophage metalloelastase Proteins 0.000 claims description 15
- 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 claims description 11
- 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 2
- -1 4-benzyloxyphenyl Chemical group 0.000 claims 13
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 8
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 5
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 1
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- 239000001099 ammonium carbonate Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
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- 235000019439 ethyl acetate Nutrition 0.000 description 8
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- DNEVHXPXJVTGNT-UHFFFAOYSA-N 3-(4-hydroxyphenyl)furan-2-carbothialdehyde Chemical compound OC1=CC=C(C=C1)C1=C(OC=C1)C=S DNEVHXPXJVTGNT-UHFFFAOYSA-N 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- LXWLEQZDXOQZGW-UHFFFAOYSA-N 3-bromofuran Chemical compound BrC=1C=COC=1 LXWLEQZDXOQZGW-UHFFFAOYSA-N 0.000 description 1
- DQCZQFOIDHTCKO-UHFFFAOYSA-N 5-[3-[4-[(2-chlorophenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound ClC1=CC=CC=C1COC(C=C1)=CC=C1SC1=C(C2C(NC(=O)N2)=O)OC=C1 DQCZQFOIDHTCKO-UHFFFAOYSA-N 0.000 description 1
- UGPXGSWFLXWCSE-UHFFFAOYSA-N 5-[3-[4-[(2-methoxyphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound COC1=CC=CC=C1COC(C=C1)=CC=C1SC1=C(C2C(NC(=O)N2)=O)OC=C1 UGPXGSWFLXWCSE-UHFFFAOYSA-N 0.000 description 1
- KCSIYVQRLLHGQX-UHFFFAOYSA-N 5-[3-[4-[(2-methylphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound CC1=CC=CC=C1COC(C=C1)=CC=C1SC1=C(C2C(NC(=O)N2)=O)OC=C1 KCSIYVQRLLHGQX-UHFFFAOYSA-N 0.000 description 1
- LNHDBLTYPMOHSS-UHFFFAOYSA-N 5-[3-[4-[(3,5-dimethoxyphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound COC1=CC(OC)=CC(COC=2C=CC(SC3=C(OC=C3)C3C(NC(=O)N3)=O)=CC=2)=C1 LNHDBLTYPMOHSS-UHFFFAOYSA-N 0.000 description 1
- ADWHQIVRZPXWQS-UHFFFAOYSA-N 5-[3-[4-[(3-chlorophenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound ClC1=CC=CC(COC=2C=CC(SC3=C(OC=C3)C3C(NC(=O)N3)=O)=CC=2)=C1 ADWHQIVRZPXWQS-UHFFFAOYSA-N 0.000 description 1
- YMFBYMXAQABRLU-UHFFFAOYSA-N 5-[3-[4-[(3-methoxyphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound COC1=CC=CC(COC=2C=CC(SC3=C(OC=C3)C3C(NC(=O)N3)=O)=CC=2)=C1 YMFBYMXAQABRLU-UHFFFAOYSA-N 0.000 description 1
- CXEKSVVDMIAMLF-UHFFFAOYSA-N 5-[3-[4-[(3-methylphenyl)methoxy]phenyl]sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound CC1=CC=CC(COC=2C=CC(SC3=C(OC=C3)C3C(NC(=O)N3)=O)=CC=2)=C1 CXEKSVVDMIAMLF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60273604P | 2004-08-19 | 2004-08-19 | |
| US60/602,736 | 2004-08-19 | ||
| PCT/US2005/029259 WO2006023562A2 (en) | 2004-08-19 | 2005-08-17 | 5-[3-(4-benzyloxyphenylthio)-fur-2-yl]-imidazolidin-2, 4-dione and analogues as inhibitors of macrophage elastase |
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| AU2005277432A1 AU2005277432A1 (en) | 2006-03-02 |
| AU2005277432B2 true AU2005277432B2 (en) | 2011-11-24 |
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| EP (1) | EP1789036B1 (enExample) |
| JP (1) | JP5042833B2 (enExample) |
| KR (1) | KR101197325B1 (enExample) |
| CN (1) | CN101014338B (enExample) |
| AT (1) | ATE508744T1 (enExample) |
| AU (1) | AU2005277432B2 (enExample) |
| BR (1) | BRPI0514470B8 (enExample) |
| CA (1) | CA2577430C (enExample) |
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| ES (1) | ES2364068T3 (enExample) |
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| RU (1) | RU2391339C2 (enExample) |
| SI (1) | SI1789036T1 (enExample) |
| WO (1) | WO2006023562A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008051260A1 (en) * | 2006-01-13 | 2008-05-02 | Battelle Memorial Institute | Methods for assessing copd-retlated diseases |
| EP2907512A1 (en) | 2014-02-14 | 2015-08-19 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Inhibitors of MMP-12 as antiviral Agents |
| US10532102B2 (en) * | 2016-08-19 | 2020-01-14 | Foresee Pharmaceuticals Co., Ltd. | Pharmaceutical composition and methods of uses |
| ES2910833T3 (es) * | 2016-08-19 | 2022-05-13 | Foresee Pharmaceuticals Co Ltd | Composición farmacéutica y procedimientos de usos |
| ES2865854T3 (es) * | 2016-09-23 | 2021-10-18 | Kaken Pharma Co Ltd | Método para producir (r)-5-(3,4-difluorofenil)-5-[(3-metil-2-oxopiridin-1(2h)-il)metil]imidazolidin-2,4-diona y un producto intermedio para producir la misma |
| FI3793992T3 (fi) | 2018-05-15 | 2024-04-17 | Foresee Pharmaceuticals Usa Inc | Matriksin metalloproteinaasin (mmp) estäjiä ja niiden käyttömenetelmiä |
| DK4058437T3 (da) * | 2019-11-14 | 2025-01-20 | Foresee Pharmaceuticals Usa Inc | Matrix-metalloproteinase-(MMP)-inhibitorer og fremgangsmåder til anvendelse heraf |
| AU2022290589A1 (en) * | 2021-06-08 | 2023-11-23 | Foresee Pharmaceuticals Usa, Inc. | Safe administration of mmp-12 inhibitor |
| RU2766551C1 (ru) * | 2021-07-19 | 2022-03-15 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | 5-(4-хлорфенил)-3-((4-хлорфенил)амино)-5-(фенилтио)фуран-2(5н)-он, обладающий противомикробной активностью |
Citations (1)
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| US20040067996A1 (en) * | 2002-10-04 | 2004-04-08 | James Sheppeck | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE) |
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| WO2000040577A1 (en) | 1998-12-31 | 2000-07-13 | Aventis Pharmaceuticals Inc. | 1-carboxymethyl-2-oxo-azepan derivatives useful as selective inhibitors of mmp-12 |
| US6352976B1 (en) * | 1998-12-31 | 2002-03-05 | Aventis Pharmaceuticals Inc. | Selective inhibitors of MMP-12 |
| RU2150469C1 (ru) * | 1999-06-01 | 2000-06-10 | Уфимский государственный нефтяной технический университет | Способ получения 2-(фурил-2)-1,3-имидазолидинов |
| EP1288199A4 (en) | 2000-04-28 | 2005-10-12 | Shionogi & Co | INHIBITORS OF MMP-12 |
| SE0100903D0 (sv) | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| CA2447475A1 (en) | 2001-05-25 | 2002-12-05 | Chu-Biao Xue | Hydantion derivatives as inhibitors of matrix metalloproteinases |
| EP1394159A1 (fr) * | 2002-08-13 | 2004-03-03 | Warner-Lambert Company LLC | Nouveaux dérivés de thiophène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
| GB0219896D0 (en) | 2002-08-27 | 2002-10-02 | Bayer Ag | Dihydropyridine derivatives |
| SE0202539D0 (sv) | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
| US7132432B2 (en) * | 2003-06-05 | 2006-11-07 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) |
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2005
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- 2005-08-17 CA CA2577430A patent/CA2577430C/en not_active Expired - Fee Related
- 2005-08-17 WO PCT/US2005/029259 patent/WO2006023562A2/en not_active Ceased
- 2005-08-17 MX MX2007001940A patent/MX2007001940A/es active IP Right Grant
- 2005-08-17 EP EP05786673A patent/EP1789036B1/en not_active Expired - Lifetime
- 2005-08-17 DK DK05786673.3T patent/DK1789036T3/da active
- 2005-08-17 NZ NZ553258A patent/NZ553258A/en not_active IP Right Cessation
- 2005-08-17 JP JP2007527975A patent/JP5042833B2/ja not_active Expired - Fee Related
- 2005-08-17 CN CN2005800285556A patent/CN101014338B/zh not_active Expired - Fee Related
- 2005-08-17 BR BRPI0514470A patent/BRPI0514470B8/pt not_active IP Right Cessation
- 2005-08-17 ES ES05786673T patent/ES2364068T3/es not_active Expired - Lifetime
- 2005-08-17 AU AU2005277432A patent/AU2005277432B2/en not_active Ceased
- 2005-08-17 SI SI200531283T patent/SI1789036T1/sl unknown
- 2005-08-17 RU RU2007105822/04A patent/RU2391339C2/ru not_active IP Right Cessation
- 2005-08-17 US US11/205,954 patent/US7179831B2/en not_active Expired - Lifetime
- 2005-08-17 KR KR1020077006294A patent/KR101197325B1/ko not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040067996A1 (en) * | 2002-10-04 | 2004-04-08 | James Sheppeck | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE) |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2577430A1 (en) | 2006-03-02 |
| SI1789036T1 (sl) | 2011-09-30 |
| WO2006023562B1 (en) | 2006-06-22 |
| RU2391339C2 (ru) | 2010-06-10 |
| HK1107774A1 (en) | 2008-04-18 |
| DK1789036T3 (da) | 2011-06-27 |
| RU2007105822A (ru) | 2008-09-27 |
| CN101014338B (zh) | 2010-06-16 |
| BRPI0514470B1 (pt) | 2021-01-05 |
| JP5042833B2 (ja) | 2012-10-03 |
| KR20070045330A (ko) | 2007-05-02 |
| CN101014338A (zh) | 2007-08-08 |
| NZ553258A (en) | 2011-02-25 |
| EP1789036B1 (en) | 2011-05-11 |
| MX2007001940A (es) | 2007-07-24 |
| BRPI0514470A (pt) | 2008-06-10 |
| KR101197325B1 (ko) | 2012-11-05 |
| ATE508744T1 (de) | 2011-05-15 |
| WO2006023562A3 (en) | 2006-04-20 |
| WO2006023562A2 (en) | 2006-03-02 |
| EP1789036A2 (en) | 2007-05-30 |
| BRPI0514470B8 (pt) | 2021-07-20 |
| US7179831B2 (en) | 2007-02-20 |
| CA2577430C (en) | 2010-12-07 |
| ES2364068T3 (es) | 2011-08-24 |
| JP2008510701A (ja) | 2008-04-10 |
| EP1789036A4 (en) | 2008-08-27 |
| US20060041000A1 (en) | 2006-02-23 |
| AU2005277432A1 (en) | 2006-03-02 |
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