KR20080109087A - 티오크산틴 유도체 및 ｍｐｏ 억제제로서의 그의 용도 - Google Patents
티오크산틴 유도체 및 ｍｐｏ 억제제로서의 그의 용도 Download PDFInfo
- Publication number
- KR20080109087A KR20080109087A KR1020087027662A KR20087027662A KR20080109087A KR 20080109087 A KR20080109087 A KR 20080109087A KR 1020087027662 A KR1020087027662 A KR 1020087027662A KR 20087027662 A KR20087027662 A KR 20087027662A KR 20080109087 A KR20080109087 A KR 20080109087A
- Authority
- KR
- South Korea
- Prior art keywords
- alkoxy
- alkyl
- phenoxy
- methyl
- tetrahydro
- 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.)
- Withdrawn
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- 239000003112 inhibitor Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 367
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 42
- 238000011282 treatment Methods 0.000 claims abstract description 30
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 21
- 230000002265 prevention Effects 0.000 claims abstract description 14
- 102000004190 Enzymes Human genes 0.000 claims abstract description 11
- 108090000790 Enzymes Proteins 0.000 claims abstract description 11
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims abstract description 10
- 208000005764 Peripheral Arterial Disease Diseases 0.000 claims abstract description 8
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 214
- 125000000217 alkyl group Chemical group 0.000 claims description 185
- 229910052760 oxygen Inorganic materials 0.000 claims description 177
- 229910052717 sulfur Inorganic materials 0.000 claims description 165
- 229920006395 saturated elastomer Polymers 0.000 claims description 159
- 229910052736 halogen Inorganic materials 0.000 claims description 156
- 150000002367 halogens Chemical class 0.000 claims description 156
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 151
- 125000003118 aryl group Chemical group 0.000 claims description 124
- 229910052757 nitrogen Inorganic materials 0.000 claims description 104
- 125000005842 heteroatom Chemical group 0.000 claims description 86
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 82
- 229910052799 carbon Inorganic materials 0.000 claims description 81
- 125000004429 atom Chemical group 0.000 claims description 66
- 125000002950 monocyclic group Chemical group 0.000 claims description 64
- -1 3-[(4-fluoro-1 H -indol-3-yl) methyl] -2-thioxo-1,2,3,7-tetrahydro-6 H -purin-6-one Phosphorus Chemical compound 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 43
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 125000004122 cyclic group Chemical group 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 32
- 239000001301 oxygen Substances 0.000 claims description 32
- 201000010099 disease Diseases 0.000 claims description 31
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 26
- 201000006417 multiple sclerosis Diseases 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 208000018737 Parkinson disease Diseases 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 206010019280 Heart failures Diseases 0.000 claims description 7
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 230000009286 beneficial effect Effects 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003852 triazoles Chemical class 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- NLEUINUWQPGXHI-UHFFFAOYSA-N 3-[(5-fluoro-1h-indol-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C=1C2=CC(F)=CC=C2NC=1CN(C(NC1=O)=S)C2=C1NC=N2 NLEUINUWQPGXHI-UHFFFAOYSA-N 0.000 claims description 4
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 206010006451 bronchitis Diseases 0.000 claims description 4
- 150000002244 furazanes Chemical class 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- WIOYFBDCQDDCTI-UHFFFAOYSA-N 2-sulfanylidene-3-[2-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]propyl]-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=C(C(F)(F)F)N=C1 WIOYFBDCQDDCTI-UHFFFAOYSA-N 0.000 claims description 3
- SXNNLWVBOSOYAT-UHFFFAOYSA-N 3-[(5-chloro-1h-indol-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C12=CC(Cl)=CC=C2NC=C1CN(C(NC1=O)=S)C2=C1NC=N2 SXNNLWVBOSOYAT-UHFFFAOYSA-N 0.000 claims description 3
- KFZWPCHWGYQNRM-UHFFFAOYSA-N 3-[2-[[2-(dimethylamino)pyrimidin-5-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CN=C(N(C)C)N=C1 KFZWPCHWGYQNRM-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 206010065563 Eosinophilic bronchitis Diseases 0.000 claims description 3
- 201000009267 bronchiectasis Diseases 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 230000002458 infectious effect Effects 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 210000002569 neuron Anatomy 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- HNUHQXANZGQWGQ-UHFFFAOYSA-N 2-sulfanylidene-3-[2-(2h-triazol-4-ylmethylamino)propyl]-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CN=NN1 HNUHQXANZGQWGQ-UHFFFAOYSA-N 0.000 claims description 2
- YVQCDZWXMRZDNJ-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2NC(CN3C(=S)NC(C=4NC=NC=43)=O)=NC2=C1 YVQCDZWXMRZDNJ-UHFFFAOYSA-N 0.000 claims description 2
- MAQKUFVZHSCAGH-UHFFFAOYSA-N 3-(1h-pyrazol-5-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC=1C=CNN=1 MAQKUFVZHSCAGH-UHFFFAOYSA-N 0.000 claims description 2
- IIIADLWTNVXNBD-UHFFFAOYSA-N 3-(2-aminopropyl)-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O=C1NC(=S)N(CC(N)C)C2=C1NC=N2 IIIADLWTNVXNBD-UHFFFAOYSA-N 0.000 claims description 2
- MYYPRTCFPDGPGK-UHFFFAOYSA-N 3-(2-phenyl-2-pyridin-2-ylethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C=1N=CC=CC=1)C1=CC=CC=C1 MYYPRTCFPDGPGK-UHFFFAOYSA-N 0.000 claims description 2
- XOQCUPGBGQMLQK-UHFFFAOYSA-N 3-(pyridin-2-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC1=CC=CC=N1 XOQCUPGBGQMLQK-UHFFFAOYSA-N 0.000 claims description 2
- AHKFFPZJELSEDV-UHFFFAOYSA-N 3-(pyridin-3-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC1=CC=CN=C1 AHKFFPZJELSEDV-UHFFFAOYSA-N 0.000 claims description 2
- UZWAFZKSLZCFRV-UHFFFAOYSA-N 3-(pyridin-4-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC1=CC=NC=C1 UZWAFZKSLZCFRV-UHFFFAOYSA-N 0.000 claims description 2
- AMZQGGBZPWAFRK-UHFFFAOYSA-N 3-(quinolin-4-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CN3C(=S)NC(C=4NC=NC=43)=O)=CC=NC2=C1 AMZQGGBZPWAFRK-UHFFFAOYSA-N 0.000 claims description 2
- SCYILAUVHGNMOS-UHFFFAOYSA-N 3-[(1-methylindol-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2N(C)C(CN3C(NC(=O)C=4NC=NC=43)=S)=CC2=C1 SCYILAUVHGNMOS-UHFFFAOYSA-N 0.000 claims description 2
- WYPCJTAXRKLCNR-UHFFFAOYSA-N 3-[(2-butyl-4-chloro-1h-imidazol-5-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound N1C(CCCC)=NC(Cl)=C1CN1C(=S)NC(=O)C2=C1N=CN2 WYPCJTAXRKLCNR-UHFFFAOYSA-N 0.000 claims description 2
- ILPHIXRPMGQFJZ-UHFFFAOYSA-N 3-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CC1=NOC(C)=C1CN1C(=S)NC(=O)C2=C1N=CN2 ILPHIXRPMGQFJZ-UHFFFAOYSA-N 0.000 claims description 2
- HVYDXNSLQRFDIG-UHFFFAOYSA-N 3-[(3-butoxypyridin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCCCOC1=CC=CN=C1CN1C(=S)NC(=O)C2=C1N=CN2 HVYDXNSLQRFDIG-UHFFFAOYSA-N 0.000 claims description 2
- GSEOEHAWXVFUCX-UHFFFAOYSA-N 3-[(3-propan-2-yl-1,2-oxazol-5-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound O1N=C(C(C)C)C=C1CN1C(=S)NC(=O)C2=C1N=CN2 GSEOEHAWXVFUCX-UHFFFAOYSA-N 0.000 claims description 2
- XXICVNQMYQJXLB-UHFFFAOYSA-N 3-[(4-butoxypyridin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCCCOC1=CC=NC(CN2C(NC(=O)C=3NC=NC=32)=S)=C1 XXICVNQMYQJXLB-UHFFFAOYSA-N 0.000 claims description 2
- JUHNYHJKAXOZNQ-UHFFFAOYSA-N 3-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CC1=NON=C1CN1C(=S)NC(=O)C2=C1N=CN2 JUHNYHJKAXOZNQ-UHFFFAOYSA-N 0.000 claims description 2
- XFTQGGQXLLFMET-UHFFFAOYSA-N 3-[(5-methylpyrazin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=NC(C)=CN=C1CN1C(=S)NC(=O)C2=C1N=CN2 XFTQGGQXLLFMET-UHFFFAOYSA-N 0.000 claims description 2
- FCYBVAXJKFBGAG-UHFFFAOYSA-N 3-[(6-butoxypyridin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCCCOC1=CC=CC(CN2C(NC(=O)C=3NC=NC=32)=S)=N1 FCYBVAXJKFBGAG-UHFFFAOYSA-N 0.000 claims description 2
- ZBDZGNKVUOCITH-UHFFFAOYSA-N 3-[(6-phenoxypyridin-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C=N1)=CC=C1OC1=CC=CC=C1 ZBDZGNKVUOCITH-UHFFFAOYSA-N 0.000 claims description 2
- BFIWTKIXULBUTE-UHFFFAOYSA-N 3-[1-(1h-benzimidazol-2-yl)ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound N=1C2=CC=CC=C2NC=1C(C)N(C(NC1=O)=S)C2=C1NC=N2 BFIWTKIXULBUTE-UHFFFAOYSA-N 0.000 claims description 2
- KHHYBTYRTYJWQL-UHFFFAOYSA-N 3-[2-(1h-benzimidazol-2-yl)ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2NC(CCN3C(=S)NC(C=4NC=NC=43)=O)=NC2=C1 KHHYBTYRTYJWQL-UHFFFAOYSA-N 0.000 claims description 2
- VQQXXEBNSFHZEL-UHFFFAOYSA-N 3-[2-(1h-imidazol-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=NC=CN1 VQQXXEBNSFHZEL-UHFFFAOYSA-N 0.000 claims description 2
- VPIIFTJWQLSYIL-UHFFFAOYSA-N 3-[2-(pyridin-2-ylmethoxy)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)OCC1=CC=CC=N1 VPIIFTJWQLSYIL-UHFFFAOYSA-N 0.000 claims description 2
- ATPOLLKTGMVGBH-UHFFFAOYSA-N 3-[2-(pyridin-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CC=N1 ATPOLLKTGMVGBH-UHFFFAOYSA-N 0.000 claims description 2
- RRQORCIDUZXJPT-UHFFFAOYSA-N 3-[2-(pyridin-3-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CN=C1 RRQORCIDUZXJPT-UHFFFAOYSA-N 0.000 claims description 2
- YMEBQHCQKRPKCI-UHFFFAOYSA-N 3-[2-(pyridin-4-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=NC=C1 YMEBQHCQKRPKCI-UHFFFAOYSA-N 0.000 claims description 2
- SKAUBHPJNDJLBF-UHFFFAOYSA-N 3-[2-(quinolin-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=CC2=NC(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 SKAUBHPJNDJLBF-UHFFFAOYSA-N 0.000 claims description 2
- DYKYDXGYDOPQCH-UHFFFAOYSA-N 3-[2-(quinolin-3-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=CC2=CC(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CN=C21 DYKYDXGYDOPQCH-UHFFFAOYSA-N 0.000 claims description 2
- FZDOSCHSMNDEKZ-UHFFFAOYSA-N 3-[2-(quinolin-4-ylmethylamino)ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CNCCN3C(=S)NC(C=4NC=NC=43)=O)=CC=NC2=C1 FZDOSCHSMNDEKZ-UHFFFAOYSA-N 0.000 claims description 2
- ZIDMKBGVDCBFNB-UHFFFAOYSA-N 3-[2-[(1-methylimidazol-2-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=NC=CN1C ZIDMKBGVDCBFNB-UHFFFAOYSA-N 0.000 claims description 2
- CKBADCZMJZPWOE-UHFFFAOYSA-N 3-[2-[(1-methylindol-3-yl)methylamino]ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C12=CC=CC=C2N(C)C=C1CNCCN1C(=S)NC(=O)C2=C1N=CN2 CKBADCZMJZPWOE-UHFFFAOYSA-N 0.000 claims description 2
- RSEFPWXFDKRGNQ-UHFFFAOYSA-N 3-[2-[(1-methylindol-3-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CN(C)C2=C1 RSEFPWXFDKRGNQ-UHFFFAOYSA-N 0.000 claims description 2
- HJJAUEDOGPHQPS-UHFFFAOYSA-N 3-[2-[(1-methylpyrrol-2-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CN1C HJJAUEDOGPHQPS-UHFFFAOYSA-N 0.000 claims description 2
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
- 229960005001 ticlopidine Drugs 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
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- 229940116269 uric acid Drugs 0.000 description 1
- 210000003934 vacuole Anatomy 0.000 description 1
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- 238000007794 visualization technique Methods 0.000 description 1
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- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
- 229960005332 zileuton Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/20—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two sulfur atoms
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- 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
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79166706P | 2006-04-13 | 2006-04-13 | |
| US60/791,667 | 2006-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080109087A true KR20080109087A (ko) | 2008-12-16 |
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| KR1020097014335A Ceased KR20090109087A (ko) | 2006-04-13 | 2008-09-25 | 도전체 접속용 부재 및 그의 제조 방법, 접속 구조, 및 태양 전지 모듈 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097014335A Ceased KR20090109087A (ko) | 2006-04-13 | 2008-09-25 | 도전체 접속용 부재 및 그의 제조 방법, 접속 구조, 및 태양 전지 모듈 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8026244B2 (enExample) |
| EP (1) | EP2010535B1 (enExample) |
| JP (1) | JP2009533427A (enExample) |
| KR (2) | KR20080109087A (enExample) |
| CN (1) | CN101466712A (enExample) |
| AR (1) | AR060429A1 (enExample) |
| AU (1) | AU2007239147A1 (enExample) |
| BR (1) | BRPI0711529A2 (enExample) |
| CA (1) | CA2649150A1 (enExample) |
| CL (1) | CL2007001042A1 (enExample) |
| EC (1) | ECSP088821A (enExample) |
| ES (1) | ES2389266T3 (enExample) |
| MX (1) | MX2008013033A (enExample) |
| NO (1) | NO20084764L (enExample) |
| TW (1) | TW200806667A (enExample) |
| UY (1) | UY30267A1 (enExample) |
| WO (1) | WO2007120098A1 (enExample) |
| ZA (1) | ZA200808195B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AR039385A1 (es) * | 2002-04-19 | 2005-02-16 | Astrazeneca Ab | Derivados de tioxantina como inhibidores de la mieloperoxidasa |
| MY140748A (en) | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
| US20090286813A1 (en) * | 2006-04-13 | 2009-11-19 | Astrazeneca Ab | Thioxanthine Derivatives and Their Use as Inhibitors of MPO |
| TW200804383A (en) * | 2006-06-05 | 2008-01-16 | Astrazeneca Ab | New compounds |
| AR066936A1 (es) * | 2007-06-13 | 2009-09-23 | Astrazeneca Ab | 3 - (2r - tetrahidrofuril - metil) - 2 - tioxantina. composiciones farmaceuticas. |
| US20090054468A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Use 938 |
| US20090053176A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Combination 937 |
| WO2010068171A1 (en) * | 2008-12-12 | 2010-06-17 | Astrazeneca Ab | A process for the preparation of 3- [ (2r) tetrahydrofuran-2- ylmethyl] -2-thioxo-l, 2, 3, 7-tetrahydro-6h-purin-6-one |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| WO2013068875A1 (en) | 2011-11-11 | 2013-05-16 | Pfizer Inc. | 2-thiopyrimidinones |
| MX2014011752A (es) * | 2012-03-29 | 2015-04-17 | Basf Se | Compuestos heterobiciclicos n-sustituidos y derivados para combatir plagas de animales ii. |
| US20170247343A1 (en) * | 2014-09-11 | 2017-08-31 | Bristol-Myers Squibb Company | Thioether triazolopyridine and triazolopyrimidine inhibitors of myeloperoxidase |
| US9616063B2 (en) | 2014-12-01 | 2017-04-11 | Astrazeneca Ab | 1-[2-(aminomethyl)benzyl]-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-ones as inhibitors of myeloperoxidase |
| CN107531647A (zh) | 2015-05-05 | 2018-01-02 | 辉瑞大药厂 | 2‑硫代嘧啶酮类 |
| WO2017040450A1 (en) * | 2015-09-03 | 2017-03-09 | Bristol-Myers Squibb Company | Triazolopyridine inhibitors of myeloperoxidase |
| WO2017160632A1 (en) * | 2016-03-14 | 2017-09-21 | Bristol-Myers Squibb Company | Triazolopyridine inhibitors of myeloperoxidase |
| CN115403584B (zh) * | 2021-05-26 | 2024-04-02 | 长春金赛药业有限责任公司 | 2-硫代-2,3-二氢嘧啶-4-酮衍生物、药物组合物及其制备方法和应用 |
| UY40399A (es) | 2022-08-18 | 2024-02-15 | Astrazeneca Ab | Inhibidores de mieloperoxidasa |
| WO2025172474A1 (en) | 2024-02-15 | 2025-08-21 | Astrazeneca Ab | Inhibitors of myeloperoxidase |
| WO2025190901A1 (en) | 2024-03-13 | 2025-09-18 | Institut National de la Santé et de la Recherche Médicale | Use of myeloperoxidase (mpo) inhibitors for promoting cd8+ t cell responses |
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| GB9312853D0 (en) * | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| US5773423A (en) * | 1993-07-13 | 1998-06-30 | The United States Of America As Represented By The Department Of Health And Human Services | A3 adenosine receptor agonists |
| US5708009A (en) * | 1993-12-21 | 1998-01-13 | Eli Lilly And Company | Methods of inhibiting myeloperoxidase activity |
| US6780865B1 (en) * | 1994-02-18 | 2004-08-24 | Cell Therapeutics, Inc. | Compounds having selective hydrolytic potentials |
| ATE247116T1 (de) * | 1994-12-13 | 2003-08-15 | Euro Celtique Sa | Arylthioxanthine |
| EP1016407B1 (en) * | 1997-09-05 | 2006-05-10 | Kyowa Hakko Kogyo Co., Ltd. | Xanthine derivatives for treating brain ischemia |
| US6413975B1 (en) * | 1999-04-02 | 2002-07-02 | Euro-Celtique, S.A. | Purine derivatives having phosphodiesterase iv inhibition activity |
| AR039385A1 (es) * | 2002-04-19 | 2005-02-16 | Astrazeneca Ab | Derivados de tioxantina como inhibidores de la mieloperoxidasa |
| SE0302756D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel Compounds |
| MY140748A (en) * | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
| US20090286813A1 (en) * | 2006-04-13 | 2009-11-19 | Astrazeneca Ab | Thioxanthine Derivatives and Their Use as Inhibitors of MPO |
| TW200804383A (en) * | 2006-06-05 | 2008-01-16 | Astrazeneca Ab | New compounds |
| US20090054468A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Use 938 |
-
2007
- 2007-04-10 UY UY30267A patent/UY30267A1/es unknown
- 2007-04-10 TW TW096112534A patent/TW200806667A/zh unknown
- 2007-04-12 CN CNA200780022184XA patent/CN101466712A/zh active Pending
- 2007-04-12 AR ARP070101557A patent/AR060429A1/es unknown
- 2007-04-12 CA CA002649150A patent/CA2649150A1/en not_active Abandoned
- 2007-04-12 ES ES07748015T patent/ES2389266T3/es active Active
- 2007-04-12 US US12/295,306 patent/US8026244B2/en not_active Expired - Fee Related
- 2007-04-12 JP JP2009505326A patent/JP2009533427A/ja not_active Ceased
- 2007-04-12 CL CL200701042A patent/CL2007001042A1/es unknown
- 2007-04-12 BR BRPI0711529-6A patent/BRPI0711529A2/pt not_active IP Right Cessation
- 2007-04-12 WO PCT/SE2007/000349 patent/WO2007120098A1/en not_active Ceased
- 2007-04-12 EP EP07748015A patent/EP2010535B1/en active Active
- 2007-04-12 KR KR1020087027662A patent/KR20080109087A/ko not_active Withdrawn
- 2007-04-12 MX MX2008013033A patent/MX2008013033A/es not_active Application Discontinuation
- 2007-04-12 AU AU2007239147A patent/AU2007239147A1/en not_active Abandoned
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2008
- 2008-09-25 ZA ZA200808195A patent/ZA200808195B/xx unknown
- 2008-09-25 KR KR1020097014335A patent/KR20090109087A/ko not_active Ceased
- 2008-10-14 EC EC2008008821A patent/ECSP088821A/es unknown
- 2008-11-11 NO NO20084764A patent/NO20084764L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007239147A1 (en) | 2007-10-25 |
| ECSP088821A (es) | 2008-11-27 |
| TW200806667A (en) | 2008-02-01 |
| ES2389266T3 (es) | 2012-10-24 |
| ZA200808195B (en) | 2009-08-26 |
| MX2008013033A (es) | 2008-10-17 |
| US8026244B2 (en) | 2011-09-27 |
| EP2010535A1 (en) | 2009-01-07 |
| CL2007001042A1 (es) | 2008-02-08 |
| CA2649150A1 (en) | 2007-10-25 |
| EP2010535B1 (en) | 2012-07-11 |
| BRPI0711529A2 (pt) | 2011-11-01 |
| NO20084764L (no) | 2009-01-06 |
| US20090149475A1 (en) | 2009-06-11 |
| UY30267A1 (es) | 2007-11-30 |
| CN101466712A (zh) | 2009-06-24 |
| WO2007120098A1 (en) | 2007-10-25 |
| KR20090109087A (ko) | 2009-10-19 |
| AR060429A1 (es) | 2008-06-18 |
| JP2009533427A (ja) | 2009-09-17 |
| EP2010535A4 (en) | 2011-07-20 |
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Legal Events
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| PA0105 | International application |
Patent event date: 20081112 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |