KR20090087031A - 시그마 리셉터 저해제들로서의 1,2,4-트리아졸 유도체들 - Google Patents
시그마 리셉터 저해제들로서의 1,2,4-트리아졸 유도체들 Download PDFInfo
- Publication number
- KR20090087031A KR20090087031A KR1020097011466A KR20097011466A KR20090087031A KR 20090087031 A KR20090087031 A KR 20090087031A KR 1020097011466 A KR1020097011466 A KR 1020097011466A KR 20097011466 A KR20097011466 A KR 20097011466A KR 20090087031 A KR20090087031 A KR 20090087031A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- triazol
- dichlorophenyl
- ethyl
- ylthio
- 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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- 108010085082 sigma receptors Proteins 0.000 title abstract description 9
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000003112 inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 230000000144 pharmacologic effect Effects 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 53
- -1 amphetamines Chemical compound 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 239000000651 prodrug Substances 0.000 claims description 21
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
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- 239000000126 substance Substances 0.000 claims description 8
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- GKKDDHOMQWAHCW-UHFFFAOYSA-N 4-[3-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]morpholine;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCN1CCOCC1 GKKDDHOMQWAHCW-UHFFFAOYSA-N 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- CDSJOPZTPIHZAH-UHFFFAOYSA-N 1-[2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]azepane;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCN1CCCCCC1 CDSJOPZTPIHZAH-UHFFFAOYSA-N 0.000 claims description 5
- VRIRQZRICBFNCX-UHFFFAOYSA-N 1-[3-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]propyl]-4-phenylpiperidine;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCN(CC1)CCC1C1=CC=CC=C1 VRIRQZRICBFNCX-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ZZQMRFAOFHNFSV-UHFFFAOYSA-N n-[2-[[2-(3,4-dichlorophenyl)-5-methyl-1,3-dihydro-1,2,4-triazol-3-yl]sulfanyl]ethyl]-n-propan-2-ylpropan-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.CC(C)N(C(C)C)CCSC1N=C(C)NN1C1=CC=C(Cl)C(Cl)=C1 ZZQMRFAOFHNFSV-UHFFFAOYSA-N 0.000 claims description 5
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- CTJADQLHTIKHRI-UHFFFAOYSA-N 1-[4-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]butyl]-4-phenylpiperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCN(CC1)CCC1C1=CC=CC=C1 CTJADQLHTIKHRI-UHFFFAOYSA-N 0.000 claims description 4
- GLADOPBPEAVAHM-UHFFFAOYSA-N 4-[2-[[2-(3,4-dichlorophenyl)-5-methyl-1,3-dihydro-1,2,4-triazol-3-yl]sulfanyl]ethyl]morpholine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C(Cl)C(Cl)=CC=1N1NC(C)=NC1SCCN1CCOCC1 GLADOPBPEAVAHM-UHFFFAOYSA-N 0.000 claims description 4
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- ZCLVNIZJEKLGFA-UHFFFAOYSA-H bis(4,5-dioxo-1,3,2-dioxalumolan-2-yl) oxalate Chemical compound [Al+3].[Al+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O ZCLVNIZJEKLGFA-UHFFFAOYSA-H 0.000 claims description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
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- 229960002715 nicotine Drugs 0.000 claims description 4
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
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- NXLSPZQNUCQULT-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethoxy)-1,2,4-triazole Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1OCCN1CCCC1 NXLSPZQNUCQULT-UHFFFAOYSA-N 0.000 claims description 3
- LFFGAUAMYWZXGF-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethylsulfinyl)-1,2,4-triazole Chemical compound CC1=NC(S(=O)CCN2CCCC2)=NN1C1=CC=C(Cl)C(Cl)=C1 LFFGAUAMYWZXGF-UHFFFAOYSA-N 0.000 claims description 3
- ZACUFEXNMPHFQO-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-methyl-3-(5-pyrrolidin-1-ylpentylsulfanyl)-1,2,4-triazole;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCCN1CCCC1 ZACUFEXNMPHFQO-UHFFFAOYSA-N 0.000 claims description 3
- YHSQQUFLTWNQTI-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ium-3-ylethylsulfanyl)-1,2,4-triazole;oxalate Chemical compound [O-]C(=O)C([O-])=O.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCCC1CC[NH2+]C1.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCCC1CC[NH2+]C1 YHSQQUFLTWNQTI-UHFFFAOYSA-N 0.000 claims description 3
- HHNGOHDMEJQNCX-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethylsulfinyl)-1,2,4-triazole Chemical compound CC1=NC(S(=O)CCN2CCCC2)=NN1C1=CC=CC(Cl)=C1 HHNGOHDMEJQNCX-UHFFFAOYSA-N 0.000 claims description 3
- BEXCQNGPNGUAQD-UHFFFAOYSA-N 1-(3-chlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethylsulfonyl)-1,2,4-triazole Chemical compound CC1=NC(S(=O)(=O)CCN2CCCC2)=NN1C1=CC=CC(Cl)=C1 BEXCQNGPNGUAQD-UHFFFAOYSA-N 0.000 claims description 3
- GGIJKFGRFULFRU-UHFFFAOYSA-N 1-[2-[(5-methyl-1-phenyl-1,2,4-triazol-3-yl)oxy]ethyl]piperidine Chemical compound N=1N(C=2C=CC=CC=2)C(C)=NC=1OCCN1CCCCC1 GGIJKFGRFULFRU-UHFFFAOYSA-N 0.000 claims description 3
- BURWSKNHDFFSMI-UHFFFAOYSA-N 1-[2-[[1-(3-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]piperidin-1-ium;oxalate Chemical compound [O-]C(=O)C([O-])=O.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCC[NH+]1CCCCC1.N=1N(C=2C=C(Cl)C=CC=2)C(C)=NC=1SCC[NH+]1CCCCC1 BURWSKNHDFFSMI-UHFFFAOYSA-N 0.000 claims description 3
- KYQUZVISAYTPSC-UHFFFAOYSA-N 1-[4-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]butyl]piperidine Chemical compound N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCN1CCCCC1 KYQUZVISAYTPSC-UHFFFAOYSA-N 0.000 claims description 3
- QZCBHIXFDOXQGF-UHFFFAOYSA-N 1-[4-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfinyl]butyl]-4-phenylpiperidine Chemical compound CC1=NC(S(=O)CCCCN2CCC(CC2)C=2C=CC=CC=2)=NN1C1=CC=C(Cl)C(Cl)=C1 QZCBHIXFDOXQGF-UHFFFAOYSA-N 0.000 claims description 3
- QCEYUNHXCUXRMU-UHFFFAOYSA-N 1-[5-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfanyl]pentyl]piperidine;oxalic acid Chemical compound OC(=O)C(O)=O.N=1N(C=2C=C(Cl)C(Cl)=CC=2)C(C)=NC=1SCCCCCN1CCCCC1 QCEYUNHXCUXRMU-UHFFFAOYSA-N 0.000 claims description 3
- LARBHPBCWVOBHV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-5-methyl-3-(2-pyrrolidin-1-ylethylsulfanyl)-1,3-dihydro-1,2,4-triazole;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C(Cl)C(Cl)=CC=1N1NC(C)=NC1SCCN1CCCC1 LARBHPBCWVOBHV-UHFFFAOYSA-N 0.000 claims description 3
- CADMZMJQQLJLLP-UHFFFAOYSA-N 2-[[1-(3,4-dichlorophenyl)-5-methyl-1,2,4-triazol-3-yl]sulfonyl]-n,n-diethylethanamine Chemical compound N1=C(S(=O)(=O)CCN(CC)CC)N=C(C)N1C1=CC=C(Cl)C(Cl)=C1 CADMZMJQQLJLLP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
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- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
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- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
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- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| EP06380291A EP1921073A1 (en) | 2006-11-10 | 2006-11-10 | 1,2,4-Triazole derivatives as sigma receptor inhibitors |
| EP06380291.2 | 2006-11-10 |
Publications (1)
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| KR20090087031A true KR20090087031A (ko) | 2009-08-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020097011466A Ceased KR20090087031A (ko) | 2006-11-10 | 2007-11-07 | 시그마 리셉터 저해제들로서의 1,2,4-트리아졸 유도체들 |
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| EP (2) | EP1921073A1 (enExample) |
| JP (1) | JP2010509280A (enExample) |
| KR (1) | KR20090087031A (enExample) |
| CN (1) | CN101595098B (enExample) |
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| RU (1) | RU2451015C2 (enExample) |
| WO (1) | WO2008055932A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0507602D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
| EP2116539A1 (en) | 2008-04-25 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof |
| US20100273805A1 (en) * | 2009-04-23 | 2010-10-28 | Astrazeneca Ab | Sulphide bridged derivatives as modulators of mglur5 733 |
| EP2353598A1 (en) * | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for use in the prevention and/or treatment of postoperative pain |
| EP2353591A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof |
| EP2388005A1 (en) | 2010-05-21 | 2011-11-23 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy |
| EP2415471A1 (en) | 2010-08-03 | 2012-02-08 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in opioid-induced hyperalgesia |
| EP2524694A1 (en) | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| CA2885148A1 (en) | 2012-09-21 | 2014-03-27 | Uwm Research Foundation, Inc. | Novel gabaa agonists and methods of using to control airway hyperresponsiveness and inflammation in asthma |
| EP2752411A1 (en) | 2013-01-07 | 2014-07-09 | Laboratorios Del Dr. Esteve, S.A. | 1,2,3-triazole-4-amine derivatives for the treatment of sigma receptor related diseases and disorders |
| US9879015B2 (en) | 2013-04-23 | 2018-01-30 | Laboratorios Del Dr. Esteve S.A. | Pyrazino[1,2-a]indole compounds, their preparation and use in medicaments |
| CA2909924A1 (en) | 2013-04-23 | 2014-10-30 | Laboratorios Del Dr. Esteve, S.A. | Pyrazino[1,2-a]indole compounds, their preparation and use in medicaments |
| EP2832720A1 (en) | 2013-07-30 | 2015-02-04 | Laboratorios Del. Dr. Esteve, S.A. | 1,2-disubstituted cyclobutyl compounds |
| SG11201604480PA (en) | 2013-12-17 | 2016-07-28 | Esteve Labor Dr | SEROTONIN-NOREPINEPHRINE REUPTAKE INHIBITORS (SNRIs) AND SIGMA RECEPTOR LIGANDS COMBINATIONS |
| MA41177A (fr) * | 2014-12-15 | 2017-10-24 | Esteve Labor Dr | Utilisation de ligands des récepteurs sigma dans l'arthrose |
| PT3250563T (pt) * | 2015-01-30 | 2022-02-09 | Neurocrine Biosciences Inc | Triazois substituídos e métodos relacionados aos mesmos |
| US10118904B2 (en) | 2015-06-05 | 2018-11-06 | Vertex Pharmaceuticals Incorporated | Triazoles for the treatment of Demyelinating Diseases |
| EP3711757B1 (en) * | 2017-11-14 | 2025-05-07 | SK Biopharmaceuticals Co., Ltd. | Use of a carbamate compound to prevent, alleviate or treat visceralgia or pain arising from visceral disease |
| BR112020009310A2 (pt) | 2017-11-14 | 2020-10-13 | Sk Biopharmaceuticals Co., Ltd. | combinação e composição farmacêutica para a prevenção, alívio ou tratamento da esquizofrenia. |
| KR102900174B1 (ko) | 2017-11-14 | 2025-12-16 | 에스케이바이오팜 주식회사 | 근긴장증의 예방, 경감 또는 치료를 위한 카바메이트 화합물의 용도 |
| US20200268711A1 (en) * | 2017-11-14 | 2020-08-27 | Sk Biopharmaceuticals Co., Ltd. | Use Of Carbamate Compound For Reducing Or Treating Developmental Disorders Including Fragile X Syndrome, Angelman Syndrome Or Rett Syndrome |
| EP3893892A4 (en) * | 2018-12-12 | 2022-09-14 | Rutgers, the State University of New Jersey | ORGANIC COMPOUNDS |
Family Cites Families (9)
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| DE1547640A1 (de) * | 1967-04-10 | 1969-12-04 | Agfa Gevaert Ag | Verbessertes photographisches Material |
| CA2071897A1 (en) | 1989-12-28 | 1991-06-29 | Richard A. Glennon | Sigma receptor ligands and the use thereof |
| WO2002036119A1 (en) * | 2000-11-02 | 2002-05-10 | K And K Biosciences, Inc. | Δ2,-1,2,3-triazoline anticonvulsants and their active metabolite analogues, the aminoalkylpyridines, are excitatory amino acid antagonists and antiischemic agents, useful in the treatment of cerebral ischemia resulting from stroke |
| US6797722B2 (en) | 2002-05-03 | 2004-09-28 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Use of 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-1H-1,2,4-triazole for the treatment of autoimmune diseases |
| SE0301232D0 (sv) | 2003-04-25 | 2003-04-25 | Astrazeneca Ab | Novel use |
| EP1677786A1 (en) | 2003-10-18 | 2006-07-12 | Bayer HealthCare AG | 5-substituted 2-(phenylmethyl)thio-4-phenyl-4h-1,2,4-triazole derivatives and related compounds as gaba-agonists for the treatment of urinary incontinence and related diseases |
| BRPI0415851A (pt) | 2003-10-24 | 2007-01-02 | Solvay Pharm Gmbh | utilizações médicas de compostos que apresentam atividade antagonìstica de cb1 e tratamento de combinação envolvendo os referidos compostos |
| DE102005007304A1 (de) * | 2005-02-17 | 2006-08-24 | Merck Patent Gmbh | Triazolderivate |
| GB0504556D0 (en) | 2005-03-04 | 2005-04-13 | Pfizer Ltd | Novel pharmaceuticals |
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- 2007-11-07 BR BRPI0718587-1A2A patent/BRPI0718587A2/pt not_active IP Right Cessation
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2011
- 2011-09-12 US US13/229,917 patent/US8349878B2/en not_active Expired - Fee Related
Also Published As
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| US20100004224A1 (en) | 2010-01-07 |
| ES2453497T3 (es) | 2014-04-08 |
| US8349878B2 (en) | 2013-01-08 |
| AU2007316605B2 (en) | 2012-02-09 |
| US8039497B2 (en) | 2011-10-18 |
| EP2097394A1 (en) | 2009-09-09 |
| CN101595098A (zh) | 2009-12-02 |
| RU2451015C2 (ru) | 2012-05-20 |
| CA2668994A1 (en) | 2008-05-15 |
| NZ577557A (en) | 2011-12-22 |
| MX2009004746A (es) | 2009-05-22 |
| JP2010509280A (ja) | 2010-03-25 |
| CN101595098B (zh) | 2012-07-18 |
| EP1921073A1 (en) | 2008-05-14 |
| WO2008055932A1 (en) | 2008-05-15 |
| AU2007316605A1 (en) | 2008-05-15 |
| EP2097394B1 (en) | 2013-12-25 |
| BRPI0718587A2 (pt) | 2014-03-11 |
| RU2009122197A (ru) | 2010-12-20 |
| US20120004211A1 (en) | 2012-01-05 |
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