ZA200601146B - Piperazone with OR-substituted phenyl group and their use as Gly T1 inhibitors - Google Patents

Piperazone with OR-substituted phenyl group and their use as Gly T1 inhibitors Download PDF

Info

Publication number: ZA200601146B
Authority: ZA; South Africa
Prior art keywords: phenyl; piperazin; methanesulfonyl; fluoro; methanone
Prior art date: 2003-08-11

Application number

ZA200601146A

Other languages

English (en)

Inventor

Jolidon Synese

Nettekoven Matthias Heinrich

Pinard Emmanuel

Narquizian Robert

Norcross Roger David

Stalder Henri

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

2003-08-11

Filing date

2006-02-08

Publication date

2007-05-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34130061&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200601146(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2006-02-08 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2007-05-30 Publication of ZA200601146B publication Critical patent/ZA200601146B/en

Links

125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 20
239000003112 inhibitor Substances 0.000 title description 5
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 title 1
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 104
150000001875 compounds Chemical class 0.000 claims description 80
229910052736 halogen Inorganic materials 0.000 claims description 46
150000002367 halogens Chemical group 0.000 claims description 46
-1 bicyclo[2.2.1]heptyl Chemical group 0.000 claims description 32
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 14
201000000980 schizophrenia Diseases 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 11
229910052792 caesium Inorganic materials 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
208000028017 Psychotic disease Diseases 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
208000035475 disorder Diseases 0.000 claims description 7
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
206010012289 Dementia Diseases 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
239000005864 Sulphur Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
230000001771 impaired effect Effects 0.000 claims description 5
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
230000019771 cognition Effects 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
230000003213 activating effect Effects 0.000 claims description 3
230000006735 deficit Effects 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
CLPDPJIINMSDAG-UHFFFAOYSA-N 4-[4-(2-cyclopentyloxy-5-methylsulfonylbenzoyl)piperazin-1-yl]-2-fluorobenzonitrile Chemical compound C1CN(C=2C=C(F)C(C#N)=CC=2)CCN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1OC1CCCC1 CLPDPJIINMSDAG-UHFFFAOYSA-N 0.000 claims description 2
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 2
239000012317 TBTU Substances 0.000 claims description 2
HXWMJBQWXCYJSG-UHFFFAOYSA-N [4-(4-chloro-2-nitrophenyl)piperazin-1-yl]-[4-(dimethylamino)-2-methoxy-5-nitrophenyl]methanone Chemical compound COC1=CC(N(C)C)=C([N+]([O-])=O)C=C1C(=O)N1CCN(C=2C(=CC(Cl)=CC=2)[N+]([O-])=O)CC1 HXWMJBQWXCYJSG-UHFFFAOYSA-N 0.000 claims description 2
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 2
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
235000013350 formula milk Nutrition 0.000 claims 36
229960005141 piperazine Drugs 0.000 claims 14
150000002431 hydrogen Chemical class 0.000 claims 3
102100028644 Tenascin-R Human genes 0.000 claims 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
239000000126 substance Substances 0.000 claims 2
229940124530 sulfonamide Drugs 0.000 claims 2
150000003456 sulfonamides Chemical class 0.000 claims 2
108010020387 tenascin R Proteins 0.000 claims 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
FDAUGFSWIZUKGM-UHFFFAOYSA-N 1-[4-[4-[2-(cyclobutylmethoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]-3-fluorophenyl]ethanone Chemical compound FC1=CC(C(=O)C)=CC=C1N1CCN(C(=O)C=2C(=CC=C(C=2)S(C)(=O)=O)OCC2CCC2)CC1 FDAUGFSWIZUKGM-UHFFFAOYSA-N 0.000 claims 1
WBYYGBHFXXFGOM-UHFFFAOYSA-N 1-[4-[4-[2-(cyclopropylmethoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]-3-fluorophenyl]ethanone Chemical compound FC1=CC(C(=O)C)=CC=C1N1CCN(C(=O)C=2C(=CC=C(C=2)S(C)(=O)=O)OCC2CC2)CC1 WBYYGBHFXXFGOM-UHFFFAOYSA-N 0.000 claims 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
JESFTAIITPRUSJ-UHFFFAOYSA-N 2,5-difluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=C(F)C=2)C#N)F)CC1 JESFTAIITPRUSJ-UHFFFAOYSA-N 0.000 claims 1
GQBGEESEVXRXFR-UHFFFAOYSA-N 2,6-difluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C=C(F)C(C#N)=C(F)C=2)CC1 GQBGEESEVXRXFR-UHFFFAOYSA-N 0.000 claims 1
GQFVRYSQXIQEKC-UHFFFAOYSA-N 2-fluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C=C(F)C(C#N)=CC=2)CC1 GQFVRYSQXIQEKC-UHFFFAOYSA-N 0.000 claims 1
KSKJRPDLQBDCAY-UHFFFAOYSA-N 3,5-difluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=CC=2F)C#N)F)CC1 KSKJRPDLQBDCAY-UHFFFAOYSA-N 0.000 claims 1
IIKQERNGSZVMCA-UHFFFAOYSA-N 3-[4-(3-chlorophenyl)piperazine-1-carbonyl]-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)N1CCN(C=2C=C(Cl)C=CC=2)CC1 IIKQERNGSZVMCA-UHFFFAOYSA-N 0.000 claims 1
HXKGYJNCJMXXEE-UHFFFAOYSA-N 3-[4-(4-acetyl-2-fluorophenyl)piperazine-1-carbonyl]-4-(2,2-dimethylpropoxy)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(C)(C)C)C(C(=O)N2CCN(CC2)C=2C(=CC(=CC=2)C(C)=O)F)=C1 HXKGYJNCJMXXEE-UHFFFAOYSA-N 0.000 claims 1
FALWCSBJGDGRBX-UHFFFAOYSA-N 3-[4-(4-cyano-2-fluorophenyl)piperazine-1-carbonyl]-4-(2,2-dimethylpropoxy)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(C)(C)C)C(C(=O)N2CCN(CC2)C=2C(=CC(=CC=2)C#N)F)=C1 FALWCSBJGDGRBX-UHFFFAOYSA-N 0.000 claims 1
GTMJJECWFSYTLY-UHFFFAOYSA-N 3-[4-(4-cyano-2-fluorophenyl)piperazine-1-carbonyl]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(C(=O)N2CCN(CC2)C=2C(=CC(=CC=2)C#N)F)=C1 GTMJJECWFSYTLY-UHFFFAOYSA-N 0.000 claims 1
MDILCRFEKWGLDH-UHFFFAOYSA-N 3-fluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=CC=2)C#N)F)CC1 MDILCRFEKWGLDH-UHFFFAOYSA-N 0.000 claims 1
PGMNFQXFRLOYOT-UHFFFAOYSA-N 4-(cyclobutylmethoxy)-n-methyl-3-[4-[4-(trifluoromethyl)phenyl]piperazine-1-carbonyl]benzenesulfonamide Chemical compound C1CN(C=2C=CC(=CC=2)C(F)(F)F)CCN1C(=O)C1=CC(S(=O)(=O)NC)=CC=C1OCC1CCC1 PGMNFQXFRLOYOT-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
229940123355 Glycine uptake inhibitor Drugs 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
241000009298 Trigla lyra Species 0.000 claims 1
RQKPLLFVBWOACY-UHFFFAOYSA-N [4-(2-fluoro-4-methylsulfonylphenyl)piperazin-1-yl]-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]methanone Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=CC=2)S(C)(=O)=O)F)CC1 RQKPLLFVBWOACY-UHFFFAOYSA-N 0.000 claims 1
UAEWYJBPCXZRGM-UHFFFAOYSA-N [4-(3-amino-4-nitrophenyl)-2-methylpiperazin-1-yl]-[4-(dimethylamino)-2-methoxy-5-nitrophenyl]methanone Chemical compound COC1=CC(N(C)C)=C([N+]([O-])=O)C=C1C(=O)N1C(C)CN(C=2C=C(N)C(=CC=2)[N+]([O-])=O)CC1 UAEWYJBPCXZRGM-UHFFFAOYSA-N 0.000 claims 1
BTDNOUMJPYHXLL-UHFFFAOYSA-N [4-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-(5-methylsulfonyl-2-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=CN=2)C(F)(F)F)F)CC1 BTDNOUMJPYHXLL-UHFFFAOYSA-N 0.000 claims 1
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125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
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MOFQYSNJEBSGRH-UHFFFAOYSA-N n-methyl-4-(2,2,2-trifluoroethoxy)-3-[4-[4-(trifluoromethyl)phenyl]piperazine-1-carbonyl]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(C(=O)N2CCN(CC2)C=2C=CC(=CC=2)C(F)(F)F)=C1 MOFQYSNJEBSGRH-UHFFFAOYSA-N 0.000 claims 1
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229910052700 potassium Inorganic materials 0.000 claims 1
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108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 17
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WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 6
229930195712 glutamate Natural products 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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Classifications

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- C—CHEMISTRY; METALLURGY
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/84—Nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C07—ORGANIC CHEMISTRY
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- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- C—CHEMISTRY; METALLURGY
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- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
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- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

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ZA200601146A 2003-08-11 2006-02-08 Piperazone with OR-substituted phenyl group and their use as Gly T1 inhibitors ZA200601146B (en)

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US20050119251A1 (en) *	2001-12-21	2005-06-02	Jian-Min Fu	Nicotinamide derivatives and their use as therapeutic agents
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MXPA06001665A (es)	2006-04-28
MY145356A (en)	2012-01-31
CN1867554B (zh)	2011-07-06
UA85194C2 (ru)	2009-01-12
IL173274A0 (en)	2006-06-11
CR8193A (es)	2006-10-06
AR045360A1 (es)	2005-10-26
EP1656361B1 (en)	2008-01-02
KR20060037434A (ko)	2006-05-03
ECSP066358A (es)	2006-08-30
MA27995A1 (fr)	2006-07-03
PL1656361T3 (pl)	2008-06-30
RS20060076A (sr)	2008-08-07
AU2004263306A2 (en)	2005-02-17
DE602004011076T2 (de)	2009-01-02
US20050209241A1 (en)	2005-09-22
TWI289556B (en)	2007-11-11
BRPI0413497A (pt)	2006-10-17
CY1108616T1 (el)	2014-04-09
JP4252598B2 (ja)	2009-04-08
ES2297458T3 (es)	2008-05-01
HK1098147A1 (en)	2007-07-13
CO5650253A2 (es)	2006-06-30
MEP27708A (en)	2010-06-10
US7319099B2 (en)	2008-01-15
TNSN06042A1 (en)	2007-10-03
CA2534675A1 (en)	2005-02-17
WO2005014563A1 (en)	2005-02-17
AU2004263306A1 (en)	2005-02-17
CN1867554A (zh)	2006-11-22
ME00116B (me)	2010-10-10
BRPI0413497B8 (pt)	2021-05-25
SI1656361T1 (sl)	2008-04-30
EP1656361A1 (en)	2006-05-17
CA2534675C (en)	2013-07-23
BRPI0413497B1 (pt)	2017-12-19
DK1656361T3 (da)	2008-05-05
JP2007501820A (ja)	2007-02-01
DE602004011076D1 (de)	2008-02-14
IL173274A (en)	2012-06-28
NZ544820A (en)	2009-02-28
AU2004263306B2 (en)	2010-04-22
RS53252B (sr)	2014-08-29
NO20060541L (no)	2006-03-08
EA009986B1 (ru)	2008-04-28
EA200600336A1 (ru)	2006-08-25
US20080119486A1 (en)	2008-05-22
TW200524883A (en)	2005-08-01
ATE382611T1 (de)	2008-01-15
EG26404A (en)	2013-10-21
HRP20080137T3 (en)	2008-06-30
NO332263B1 (no)	2012-08-13
KR100774622B1 (ko)	2007-11-08
US7605163B2 (en)	2009-10-20
PT1656361E (pt)	2008-03-05

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