CA2613068A1 - Indole carboxamides en tant qu'inhibiteurs d'ikk2 - Google Patents
Indole carboxamides en tant qu'inhibiteurs d'ikk2 Download PDFInfo
- Publication number
- CA2613068A1 CA2613068A1 CA002613068A CA2613068A CA2613068A1 CA 2613068 A1 CA2613068 A1 CA 2613068A1 CA 002613068 A CA002613068 A CA 002613068A CA 2613068 A CA2613068 A CA 2613068A CA 2613068 A1 CA2613068 A1 CA 2613068A1
- Authority
- CA
- Canada
- Prior art keywords
- indole
- carboxamide
- piperidinyl
- ethylsulfonyl
- methyl
- 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.)
- Abandoned
Links
- 239000003112 inhibitor Substances 0.000 title abstract description 32
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 458
- 238000000034 method Methods 0.000 claims abstract description 162
- 102100021854 Inhibitor of nuclear factor kappa-B kinase subunit beta Human genes 0.000 claims abstract description 58
- 101710205525 Inhibitor of nuclear factor kappa-B kinase subunit beta Proteins 0.000 claims abstract description 58
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
- 208000035475 disorder Diseases 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 230000000694 effects Effects 0.000 claims abstract description 39
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 18
- 208000006673 asthma Diseases 0.000 claims abstract description 12
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 12
- -1 1,2,3,4-tetrahydronaphthalenyl Chemical group 0.000 claims description 154
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 105
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 89
- 125000001424 substituent group Chemical group 0.000 claims description 82
- 125000001072 heteroaryl group Chemical group 0.000 claims description 77
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 28
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 27
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 19
- MZSAKRWYICVHCY-UHFFFAOYSA-N 5-[5-[(2-ethylbutylamino)methyl]thiophen-2-yl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound S1C(CNCC(CC)CC)=CC=C1C1=CC(C(N)=O)=C(NC=C2C3CCN(CC3)S(=O)(=O)CC)C2=C1 MZSAKRWYICVHCY-UHFFFAOYSA-N 0.000 claims description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 17
- 230000001404 mediated effect Effects 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000004450 alkenylene group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- ILSCBXJRBBQQHQ-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[5-[(2-methylbutylamino)methyl]thiophen-2-yl]-1h-indole-7-carboxamide Chemical compound S1C(CNCC(C)CC)=CC=C1C1=CC(C(N)=O)=C(NC=C2C3CCN(CC3)S(=O)(=O)CC)C2=C1 ILSCBXJRBBQQHQ-UHFFFAOYSA-N 0.000 claims description 11
- JQSVGLKMJVIPOC-UHFFFAOYSA-N 5-[5-[(cyclopropylmethylamino)methyl]pyridin-3-yl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNCC4CC4)C=NC=3)C=C12 JQSVGLKMJVIPOC-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- MNEXJLKMFBQODK-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[5-[(2-propylpyrrolidin-1-yl)methyl]thiophen-3-yl]-1h-indole-7-carboxamide Chemical compound CCCC1CCCN1CC1=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CC)=CNC3=C(C(N)=O)C=2)=CS1 MNEXJLKMFBQODK-UHFFFAOYSA-N 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- NHEZTRJVOYETLW-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-(morpholin-4-ylmethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4CCOCC4)C=CC=3)C=C12 NHEZTRJVOYETLW-UHFFFAOYSA-N 0.000 claims description 8
- JLSOJRYBDWNWQZ-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-(piperidin-1-ylmethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4CCCCC4)C=CC=3)C=C12 JLSOJRYBDWNWQZ-UHFFFAOYSA-N 0.000 claims description 8
- 208000030507 AIDS Diseases 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 230000002757 inflammatory effect Effects 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- ZRNFZUCTSXYBIH-UHFFFAOYSA-N 5-[3-[(dimethylamino)methyl]-4,5-dimethoxyphenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(OC)C(OC)=C(CN(C)C)C=3)C=C12 ZRNFZUCTSXYBIH-UHFFFAOYSA-N 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 210000000056 organ Anatomy 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- CEPOUYRGTHAUNV-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[(2-methylpropylamino)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNCC(C)C)C=CC=3)C=C12 CEPOUYRGTHAUNV-UHFFFAOYSA-N 0.000 claims description 5
- MWRAGYJIFVANOA-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[(thiophen-2-ylmethylamino)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNCC=4SC=CC=4)C=CC=3)C=C12 MWRAGYJIFVANOA-UHFFFAOYSA-N 0.000 claims description 5
- CIPSFSCFHJHHON-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[4-(morpholin-4-ylmethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(CN4CCOCC4)=CC=3)C=C12 CIPSFSCFHJHHON-UHFFFAOYSA-N 0.000 claims description 5
- LOHLFPJLUSQSLI-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[5-[(2-phenylpyrrolidin-1-yl)methyl]thiophen-3-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4C(CCC4)C=4C=CC=CC=4)SC=3)C=C12 LOHLFPJLUSQSLI-UHFFFAOYSA-N 0.000 claims description 5
- KXNSPBILEROVBA-UHFFFAOYSA-N 5-[5-(ethylaminomethyl)thiophen-2-yl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound S1C(CNCC)=CC=C1C1=CC(C(N)=O)=C(NC=C2C3CCN(CC3)S(=O)(=O)CC)C2=C1 KXNSPBILEROVBA-UHFFFAOYSA-N 0.000 claims description 5
- IWVVNWTYUSAZEC-UHFFFAOYSA-N 5-[5-[[ethyl(methyl)amino]methyl]thiophen-3-yl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound S1C(CN(C)CC)=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CC)=CNC3=C(C(N)=O)C=2)=C1 IWVVNWTYUSAZEC-UHFFFAOYSA-N 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 206010003591 Ataxia Diseases 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 206010006895 Cachexia Diseases 0.000 claims description 5
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 5
- 208000017604 Hodgkin disease Diseases 0.000 claims description 5
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 208000001132 Osteoporosis Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 5
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 5
- 201000002661 Spondylitis Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 206010025135 lupus erythematosus Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 5
- 230000009885 systemic effect Effects 0.000 claims description 5
- 230000017423 tissue regeneration Effects 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- PANPQCMBJYFIMJ-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[4-(piperidin-1-ylmethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(CN4CCCCC4)=CC=3)C=C12 PANPQCMBJYFIMJ-UHFFFAOYSA-N 0.000 claims description 4
- UKKQAXPOSQINQR-NRFANRHFSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[5-[[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]methyl]thiophen-3-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4[C@@H](CCC4)COC)SC=3)C=C12 UKKQAXPOSQINQR-NRFANRHFSA-N 0.000 claims description 4
- YGPSWVIPVOCKRN-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[5-[[2-(2-methylpropyl)pyrrolidin-1-yl]methyl]thiophen-3-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4C(CCC4)CC(C)C)SC=3)C=C12 YGPSWVIPVOCKRN-UHFFFAOYSA-N 0.000 claims description 4
- KJQFUQWERSPVOJ-INIZCTEOSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[5-[[[(2s)-1-hydroxypropan-2-yl]-methylamino]methyl]thiophen-3-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN(C)[C@@H](C)CO)SC=3)C=C12 KJQFUQWERSPVOJ-INIZCTEOSA-N 0.000 claims description 4
- UAKNGYIOUFWEBD-UHFFFAOYSA-N 5-[3,4-dimethoxy-5-[(propan-2-ylamino)methyl]phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(OC)C(OC)=C(CNC(C)C)C=3)C=C12 UAKNGYIOUFWEBD-UHFFFAOYSA-N 0.000 claims description 4
- CXCDTZRMHBNQJV-UHFFFAOYSA-N 5-[3-[(dimethylamino)methyl]phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN(C)C)C=CC=3)C=C12 CXCDTZRMHBNQJV-UHFFFAOYSA-N 0.000 claims description 4
- KKVDPZPJVAQQQF-UHFFFAOYSA-N 5-[4-(2-acetamidoethyl)phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(CCNC(C)=O)=CC=3)C=C12 KKVDPZPJVAQQQF-UHFFFAOYSA-N 0.000 claims description 4
- HEMILOCFBIVUBQ-UHFFFAOYSA-N 5-[4-(acetamidomethyl)phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(CNC(C)=O)=CC=3)C=C12 HEMILOCFBIVUBQ-UHFFFAOYSA-N 0.000 claims description 4
- CXVIKAMNEJNMGC-UHFFFAOYSA-N 5-[4-[(dimethylamino)methyl]-2,3-dihydro-1-benzofuran-6-yl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN(C)C)C=4CCOC=4C=3)C=C12 CXVIKAMNEJNMGC-UHFFFAOYSA-N 0.000 claims description 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 230000037380 skin damage Effects 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 3
- NWUKWAJUWLVDOR-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-(methylaminomethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC)C=CC=3)C=C12 NWUKWAJUWLVDOR-UHFFFAOYSA-N 0.000 claims description 3
- VBHKZSRKHRGZSY-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-(piperazin-1-ylmethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4CCNCC4)C=CC=3)C=C12 VBHKZSRKHRGZSY-UHFFFAOYSA-N 0.000 claims description 3
- NUKPXFDITSVMGO-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-(propylaminomethyl)phenyl]-1h-indole-7-carboxamide Chemical compound CCCNCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CC)=CNC3=C(C(N)=O)C=2)=C1 NUKPXFDITSVMGO-UHFFFAOYSA-N 0.000 claims description 3
- NJEOUDHRVUGEBB-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[(1-hydroxypropan-2-ylamino)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC(C)CO)C=CC=3)C=C12 NJEOUDHRVUGEBB-UHFFFAOYSA-N 0.000 claims description 3
- ARBNIGLZHWXBME-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[(2-thiophen-2-ylpyrrolidin-1-yl)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4C(CCC4)C=4SC=CC=4)C=CC=3)C=C12 ARBNIGLZHWXBME-UHFFFAOYSA-N 0.000 claims description 3
- WIBPGSDPOLNPEZ-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[(pentan-3-ylamino)methyl]phenyl]-1h-indole-7-carboxamide Chemical compound CCC(CC)NCC1=CC=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CC)=CNC3=C(C(N)=O)C=2)=C1 WIBPGSDPOLNPEZ-UHFFFAOYSA-N 0.000 claims description 3
- PVLBOSQCQMVANQ-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[[(1-piperidin-1-ylcyclohexyl)methylamino]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNCC4(CCCCC4)N4CCCCC4)C=CC=3)C=C12 PVLBOSQCQMVANQ-UHFFFAOYSA-N 0.000 claims description 3
- OHLJFRFGPWDLKT-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[[2-(1,3-thiazol-2-yl)pyrrolidin-1-yl]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4C(CCC4)C=4SC=CN=4)C=CC=3)C=C12 OHLJFRFGPWDLKT-UHFFFAOYSA-N 0.000 claims description 3
- UXJBAMJKSDLHFG-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[[4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4CCN(CCOCCO)CC4)C=CC=3)C=C12 UXJBAMJKSDLHFG-UHFFFAOYSA-N 0.000 claims description 3
- QTLVCXSPZFILRH-DEOSSOPVSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[[[(2s)-2-(hydroxymethyl)-3-methylbutyl]amino]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC[C@@H](CO)C(C)C)C=CC=3)C=C12 QTLVCXSPZFILRH-DEOSSOPVSA-N 0.000 claims description 3
- PHNANSQEIZRLDG-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[[methyl(2-methylsulfonylethyl)amino]methyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN(C)CCS(C)(=O)=O)C=CC=3)C=C12 PHNANSQEIZRLDG-UHFFFAOYSA-N 0.000 claims description 3
- QZNZRIDEZDPXLE-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[5-[(propan-2-ylamino)methyl]pyridin-3-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC(C)C)C=NC=3)C=C12 QZNZRIDEZDPXLE-UHFFFAOYSA-N 0.000 claims description 3
- YFELBUQFJOFUJZ-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[5-[[methyl(propyl)amino]methyl]thiophen-3-yl]-1h-indole-7-carboxamide Chemical compound S1C(CN(C)CCC)=CC(C=2C=C3C(C4CCN(CC4)S(=O)(=O)CC)=CNC3=C(C(N)=O)C=2)=C1 YFELBUQFJOFUJZ-UHFFFAOYSA-N 0.000 claims description 3
- AWCRDOVNLSIRBI-UHFFFAOYSA-N 5-[3-(aminomethyl)phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN)C=CC=3)C=C12 AWCRDOVNLSIRBI-UHFFFAOYSA-N 0.000 claims description 3
- CWQGSANCPREIAH-UHFFFAOYSA-N 5-[3-[(cyclobutylamino)methyl]phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC4CCC4)C=CC=3)C=C12 CWQGSANCPREIAH-UHFFFAOYSA-N 0.000 claims description 3
- MVKUJQXDPPSLND-UHFFFAOYSA-N 5-[3-[(cyclopentylamino)methyl]phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC4CCCC4)C=CC=3)C=C12 MVKUJQXDPPSLND-UHFFFAOYSA-N 0.000 claims description 3
- RTZZOFFWPSHFKH-UHFFFAOYSA-N 5-[3-[(cyclopropylamino)methyl]phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CNC4CC4)C=CC=3)C=C12 RTZZOFFWPSHFKH-UHFFFAOYSA-N 0.000 claims description 3
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- 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
-
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- General Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Diabetes (AREA)
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- Physical Education & Sports Medicine (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Heart & Thoracic Surgery (AREA)
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US69525605P | 2005-06-30 | 2005-06-30 | |
US60/695,256 | 2005-06-30 | ||
PCT/US2006/025402 WO2007005534A2 (fr) | 2005-06-30 | 2006-06-28 | Composes chimiques |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2613068A1 true CA2613068A1 (fr) | 2007-01-11 |
Family
ID=37605008
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002613068A Abandoned CA2613068A1 (fr) | 2005-06-30 | 2006-06-28 | Indole carboxamides en tant qu'inhibiteurs d'ikk2 |
Country Status (19)
Country | Link |
---|---|
EP (1) | EP1896014A4 (fr) |
JP (1) | JP5059756B2 (fr) |
KR (1) | KR20080021077A (fr) |
CN (1) | CN101247804B (fr) |
AR (1) | AR055343A1 (fr) |
AU (1) | AU2006266028B2 (fr) |
BR (1) | BRPI0611674A2 (fr) |
CA (1) | CA2613068A1 (fr) |
EA (1) | EA014083B1 (fr) |
IL (1) | IL187786A0 (fr) |
MA (1) | MA29566B1 (fr) |
MX (1) | MX2007016541A (fr) |
NO (1) | NO20080457L (fr) |
NZ (1) | NZ563687A (fr) |
PE (1) | PE20070173A1 (fr) |
TW (1) | TWI380973B (fr) |
UA (1) | UA99699C2 (fr) |
WO (1) | WO2007005534A2 (fr) |
ZA (1) | ZA200709948B (fr) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0315950D0 (en) | 2003-06-11 | 2003-08-13 | Xention Discovery Ltd | Compounds |
TW200626142A (en) * | 2004-09-21 | 2006-08-01 | Glaxo Group Ltd | Chemical compounds |
GB0525164D0 (en) * | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
US20080293802A1 (en) * | 2005-12-16 | 2008-11-27 | Smithline Beecham Corporation | Chemical Compounds |
AR065804A1 (es) | 2007-03-23 | 2009-07-01 | Smithkline Beecham Corp | Compuesto de indol carboxamida, composicion farmaceutica que lo comprende y uso de dicho compuesto para preparar un medicamento |
CN102325752B (zh) * | 2008-12-19 | 2015-02-04 | 百时美施贵宝公司 | 咔唑和咔啉激酶抑制剂 |
JP2012520257A (ja) * | 2009-03-10 | 2012-09-06 | グラクソ グループ リミテッド | Ikk2阻害剤としてのインドール誘導体 |
WO2014210255A1 (fr) * | 2013-06-26 | 2014-12-31 | Abbvie Inc. | Carboxamides primaires servant d'inhibiteurs de la btk |
JP6517928B2 (ja) * | 2014-10-24 | 2019-05-22 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | キナーゼ阻害剤として有用なインドールカルボキシアミド |
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TR200000291T2 (tr) * | 1997-08-06 | 2000-07-21 | Eli Lilly And Company | Taşikinin reseptör antagonistleri olarak 2-asilaminopropanaminler. |
DE19807993A1 (de) | 1998-02-26 | 1999-09-02 | Bayer Ag | Verwendung von ß-Carbolinderivaten zur Bekämpfung von TNF-alpha-abhängigen Krankheiten |
RU2261248C2 (ru) | 1999-06-23 | 2005-09-27 | Авентис Фарма Дойчланд Гмбх | Замещенные бензимидазолы и лекарственное средство на их основе |
DE19928424A1 (de) | 1999-06-23 | 2000-12-28 | Aventis Pharma Gmbh | Substituierte Benzimidazole |
DE19951360A1 (de) | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
GB0003154D0 (en) | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
EP1268477B1 (fr) | 2000-03-15 | 2010-04-21 | Sanofi-Aventis Deutschland GmbH | Beta-carbolines substituees ayant une activite inhibitrice de l'ikb-kinase |
EP1134221A1 (fr) | 2000-03-15 | 2001-09-19 | Aventis Pharma Deutschland GmbH | Bêta-carbolines substituées comme inhibiteurs de lkB kinase |
EP1209158A1 (fr) | 2000-11-18 | 2002-05-29 | Aventis Pharma Deutschland GmbH | Bêta-carbolines subtituées |
JP2001278886A (ja) * | 2000-03-28 | 2001-10-10 | Dai Ichi Seiyaku Co Ltd | ベンゾオキサジン誘導体及びこれを含有する医薬 |
US6414013B1 (en) | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
JP4272338B2 (ja) | 2000-09-22 | 2009-06-03 | バイエル アクチェンゲゼルシャフト | ピリジン誘導体 |
US6869956B2 (en) | 2000-10-03 | 2005-03-22 | Bristol-Myers Squibb Company | Methods of treating inflammatory and immune diseases using inhibitors of IκB kinase (IKK) |
ES2260300T3 (es) | 2000-10-03 | 2006-11-01 | Bristol-Myers Squibb Company | Compuestos tetraciclicos sustituidos con amino utiles como agentes antiinflamatorios y composiciones farmaceuticas que comprenden los mismos. |
AU2002211662A1 (en) | 2000-10-12 | 2002-04-22 | Smith Kline Beecham Corporation | Nf-kappab inhibitors |
AU2002211663A1 (en) | 2000-10-12 | 2002-04-22 | Smith Kline Beecham Corporation | Nf-$g(k)b inhibitors |
CN1503673A (zh) | 2000-10-26 | 2004-06-09 | �㽭�пؼ����ɷ�����˾ | 消炎药 |
JP2002193938A (ja) | 2000-12-01 | 2002-07-10 | Bayer Ag | 4−アリールピリジン誘導体 |
US7122544B2 (en) | 2000-12-06 | 2006-10-17 | Signal Pharmaceuticals, Llc | Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto |
CZ20032287A3 (cs) | 2001-02-01 | 2004-02-18 | Bristol-Myers Squibb Company | Způsoby léčení zánětlivých a imunitních nemocí za použití inhibitorů IkB kinázy (IKK) |
WO2002094265A1 (fr) | 2001-05-24 | 2002-11-28 | Leo Pharma A/S | Procede de modulation de l'activite de nf-kb |
ES2328799T3 (es) | 2001-05-24 | 2009-11-18 | Leo Pharma A/S | Compuestos de piridilcianoguanidina. |
US20030045515A1 (en) | 2001-05-24 | 2003-03-06 | Lise Binderup | Combination medicament for treatment of neoplastic diseases |
US6638679B2 (en) | 2001-07-12 | 2003-10-28 | Kodak Polychrome Graphics, Llc | Photosensitive compositions having mixtures of alkoxy and non-alkoxy diazonium salt containing compounds |
SE0102617D0 (sv) | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
SE0102616D0 (sv) | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
MXPA04002683A (es) | 2001-09-19 | 2004-06-18 | Pharmacia Corp | Compuestos bencenosulfamida pirazolil sustituidos para el tratamiento de la inflamacion. |
ES2286275T3 (es) | 2001-09-19 | 2007-12-01 | Pharmacia Corporation | Compuestos de pirazolo sustituidos para el tratamiento de la inflamacion. |
WO2003024935A2 (fr) | 2001-09-19 | 2003-03-27 | Pharmacia Corporation | Composes de pyrazolyle substitues destines au traitement de l'inflammation |
US20030109550A1 (en) | 2001-09-19 | 2003-06-12 | Michael Clare | Substituted indazole compounds for the treatment of inflammation |
JP2005509645A (ja) | 2001-10-30 | 2005-04-14 | ファルマシア・コーポレーション | 炎症処置用のヘテロ芳香族カルボキサミド誘導体 |
WO2003084959A1 (fr) | 2002-04-03 | 2003-10-16 | Bristol-Myers Squibb Company | Composés tricycliques à base de thiopène et compositions pharmaceutiques renfermant lesdits composés |
CA2485298C (fr) | 2002-05-09 | 2008-03-11 | Pharmacia Corporation | Composes substitues de pyrazolyl utilises dans le traitement des inflammations |
CA2483890C (fr) | 2002-06-06 | 2012-12-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Composes amide d'acide 3-amino-thieno[2,3-b]pyridine-2-carboxylique substitues et processus de preparation et d'utilisation de ces composes |
GB0217757D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
DE60334386D1 (de) * | 2002-08-09 | 2010-11-11 | Merck Sharp & Dohme | Tyrosinkinaseinhibitoren |
DE10237722A1 (de) | 2002-08-17 | 2004-08-19 | Aventis Pharma Deutschland Gmbh | Indol- oder Benzimidazolderivate zur Modulation der IKappaB-Kinase |
US7329668B2 (en) | 2003-02-25 | 2008-02-12 | Bristol-Myers Squibb Company | Pyrazolopurine-based tricyclic compounds and pharmaceutical compositions comprising same |
GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
US7176214B2 (en) | 2003-05-21 | 2007-02-13 | Bristol-Myers Squibb Company | Imidazo-fused oxazolo[4,5-β]pyridine and imidazo-fused thiazolo[4,5-β]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
US7329764B2 (en) | 2003-07-31 | 2008-02-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substitute benzothiophene compounds |
US7265148B2 (en) * | 2003-09-25 | 2007-09-04 | Wyeth | Substituted pyrrole-indoles |
US7291733B2 (en) | 2003-10-10 | 2007-11-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted tricyclic heterocycles and their uses |
ES2284054T3 (es) | 2003-10-14 | 2007-11-01 | Pharmacia Corporation | Compuestos de pirazinona sustituidos para el tratamiento de la inflamacion. |
GB0400895D0 (en) * | 2004-01-15 | 2004-02-18 | Smithkline Beecham Corp | Chemical compounds |
TW200616967A (en) * | 2004-06-24 | 2006-06-01 | Smithkline Beecham Corp | Novel indazole carboxamides and their use |
TW200626142A (en) * | 2004-09-21 | 2006-08-01 | Glaxo Group Ltd | Chemical compounds |
CN101060842A (zh) * | 2004-09-21 | 2007-10-24 | 葛兰素集团有限公司 | 化合物 |
-
2006
- 2006-06-28 CA CA002613068A patent/CA2613068A1/fr not_active Abandoned
- 2006-06-28 EA EA200800183A patent/EA014083B1/ru not_active IP Right Cessation
- 2006-06-28 EP EP06785861A patent/EP1896014A4/fr not_active Withdrawn
- 2006-06-28 TW TW095123240A patent/TWI380973B/zh not_active IP Right Cessation
- 2006-06-28 UA UAA200714940A patent/UA99699C2/ru unknown
- 2006-06-28 MX MX2007016541A patent/MX2007016541A/es active IP Right Grant
- 2006-06-28 PE PE2006000761A patent/PE20070173A1/es not_active Application Discontinuation
- 2006-06-28 CN CN2006800304481A patent/CN101247804B/zh not_active Expired - Fee Related
- 2006-06-28 JP JP2008519569A patent/JP5059756B2/ja not_active Expired - Fee Related
- 2006-06-28 AU AU2006266028A patent/AU2006266028B2/en not_active Ceased
- 2006-06-28 NZ NZ563687A patent/NZ563687A/en not_active IP Right Cessation
- 2006-06-28 BR BRPI0611674-4A patent/BRPI0611674A2/pt not_active IP Right Cessation
- 2006-06-28 KR KR1020077030656A patent/KR20080021077A/ko not_active Application Discontinuation
- 2006-06-28 AR ARP060102790A patent/AR055343A1/es not_active Application Discontinuation
- 2006-06-28 WO PCT/US2006/025402 patent/WO2007005534A2/fr active Application Filing
-
2007
- 2007-11-19 ZA ZA2007/09948A patent/ZA200709948B/en unknown
- 2007-11-29 IL IL187786A patent/IL187786A0/en unknown
- 2007-12-26 MA MA30513A patent/MA29566B1/fr unknown
-
2008
- 2008-01-24 NO NO20080457A patent/NO20080457L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
JP2009500338A (ja) | 2009-01-08 |
KR20080021077A (ko) | 2008-03-06 |
EP1896014A4 (fr) | 2010-07-21 |
AU2006266028A1 (en) | 2007-01-11 |
PE20070173A1 (es) | 2007-03-14 |
IL187786A0 (en) | 2008-08-07 |
EA200800183A1 (ru) | 2008-08-29 |
NZ563687A (en) | 2011-07-29 |
ZA200709948B (en) | 2009-03-25 |
WO2007005534A3 (fr) | 2007-04-26 |
MA29566B1 (fr) | 2008-06-02 |
JP5059756B2 (ja) | 2012-10-31 |
EP1896014A2 (fr) | 2008-03-12 |
MX2007016541A (es) | 2008-03-07 |
EA014083B1 (ru) | 2010-08-30 |
AU2006266028B2 (en) | 2012-03-15 |
CN101247804B (zh) | 2012-09-26 |
NO20080457L (no) | 2008-01-29 |
BRPI0611674A2 (pt) | 2009-04-28 |
TW200738588A (en) | 2007-10-16 |
UA99699C2 (ru) | 2012-09-25 |
CN101247804A (zh) | 2008-08-20 |
AR055343A1 (es) | 2007-08-22 |
WO2007005534A2 (fr) | 2007-01-11 |
WO2007005534A8 (fr) | 2008-01-17 |
TWI380973B (zh) | 2013-01-01 |
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FZDE | Discontinued |
Effective date: 20150105 |