HRP20030214A2 - Pharmaceutically active sulfonamide derivatives bearing both lipohilic and ionisable moieties as inhibitors of protein junkinases - Google Patents
Pharmaceutically active sulfonamide derivatives bearing both lipohilic and ionisable moieties as inhibitors of protein junkinases Download PDFInfo
- Publication number
- HRP20030214A2 HRP20030214A2 HR20030214A HRP20030214A HRP20030214A2 HR P20030214 A2 HRP20030214 A2 HR P20030214A2 HR 20030214 A HR20030214 A HR 20030214A HR P20030214 A HRP20030214 A HR P20030214A HR P20030214 A2 HRP20030214 A2 HR P20030214A2
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- sulfonyl
- amino
- thien
- benzamide
- Prior art date
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- 229940124530 sulfonamide Drugs 0.000 title claims description 52
- 150000003456 sulfonamides Chemical class 0.000 title claims description 43
- 101000950669 Homo sapiens Mitogen-activated protein kinase 9 Proteins 0.000 title claims description 17
- 102100037809 Mitogen-activated protein kinase 9 Human genes 0.000 title claims description 17
- 239000003112 inhibitor Substances 0.000 title description 6
- -1 nitro, sulfonyl Chemical group 0.000 claims description 77
- 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 50
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 33
- 150000001412 amines Chemical class 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 23
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 230000014509 gene expression Effects 0.000 claims description 15
- 101000628949 Homo sapiens Mitogen-activated protein kinase 10 Proteins 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 102100026931 Mitogen-activated protein kinase 10 Human genes 0.000 claims description 11
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- HEHMZUQCKMARIT-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[[4-(trifluoromethyl)phenyl]methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C=CC(=CC=2)C(F)(F)F)=C1 HEHMZUQCKMARIT-UHFFFAOYSA-N 0.000 claims description 9
- 210000004556 brain Anatomy 0.000 claims description 9
- 208000028867 ischemia Diseases 0.000 claims description 9
- VRJHQPZVIGNGMX-UHFFFAOYSA-N piperidine-4-one Chemical group O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- OGLWFGSKCPERGG-UHFFFAOYSA-N 2-oxo-n-[[5-[4-[[4-(trifluoromethyl)phenyl]methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-1h-pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C(NC=CC=3)=O)=CC=2)CC1 OGLWFGSKCPERGG-UHFFFAOYSA-N 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 230000000302 ischemic effect Effects 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- XPPZCVNVUAJANR-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)N(C)CC=2C=CC(=CC=2)C(F)(F)F)=C1 XPPZCVNVUAJANR-UHFFFAOYSA-N 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 206010040070 Septic Shock Diseases 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 210000002216 heart Anatomy 0.000 claims description 5
- 210000003734 kidney Anatomy 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 201000006370 kidney failure Diseases 0.000 claims description 4
- 210000004185 liver Anatomy 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 230000002159 abnormal effect Effects 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 230000006806 disease prevention Effects 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical group NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims description 3
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical group NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 claims description 3
- QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical group O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- ZXDHMWKKHWUGNF-UHFFFAOYSA-N 2-sulfanylidene-n-[[5-[4-[[4-(trifluoromethyl)phenyl]methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-1h-pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C(NC=CC=3)=S)=CC=2)CC1 ZXDHMWKKHWUGNF-UHFFFAOYSA-N 0.000 claims description 2
- WNDVUNAGTFREDB-UHFFFAOYSA-N 3-methoxy-n-[[5-[3-(2-pyridin-2-ylethylamino)pyrrolidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CC(CC2)NCCC=2N=CC=CC=2)=C1 WNDVUNAGTFREDB-UHFFFAOYSA-N 0.000 claims description 2
- KPOIREPMXZFSNV-UHFFFAOYSA-N 3-methoxy-n-[[5-[3-(3-morpholin-4-ylpropylamino)pyrrolidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CC(CC2)NCCCN2CCOCC2)=C1 KPOIREPMXZFSNV-UHFFFAOYSA-N 0.000 claims description 2
- CWRSKSUXNCINND-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(2-pyridin-2-ylethylamino)azepan-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CCC2)NCCC=2N=CC=CC=2)=C1 CWRSKSUXNCINND-UHFFFAOYSA-N 0.000 claims description 2
- AABAJDPRRHYOAV-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(2-pyridin-2-ylethylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCCC=2N=CC=CC=2)=C1 AABAJDPRRHYOAV-UHFFFAOYSA-N 0.000 claims description 2
- WJVPSLHIPHKJGR-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(3-morpholin-4-ylpropylamino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCCCN2CCOCC2)=C1 WJVPSLHIPHKJGR-UHFFFAOYSA-N 0.000 claims description 2
- IEVZPTYBQVKDGM-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[(2,3,4,5,6-pentamethylphenyl)methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C(=C(C)C(C)=C(C)C=2C)C)=C1 IEVZPTYBQVKDGM-UHFFFAOYSA-N 0.000 claims description 2
- LKMMJRSDKDNVCD-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[(4-methylphenyl)methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C=CC(C)=CC=2)=C1 LKMMJRSDKDNVCD-UHFFFAOYSA-N 0.000 claims description 2
- HWVOMCVAQLMXEP-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[(4-methylsulfonylphenyl)methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C=CC(=CC=2)S(C)(=O)=O)=C1 HWVOMCVAQLMXEP-UHFFFAOYSA-N 0.000 claims description 2
- SIPDDBKNGXEADC-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[(4-phenoxyphenyl)methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 SIPDDBKNGXEADC-UHFFFAOYSA-N 0.000 claims description 2
- YDWAZMSGTWOJKZ-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[(4-propoxyphenyl)methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(OCCC)=CC=C1CNC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=C(OC)C=CC=3)=CC=2)CC1 YDWAZMSGTWOJKZ-UHFFFAOYSA-N 0.000 claims description 2
- POXCZVSHFWOHHK-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[1-[4-(trifluoromethyl)phenyl]ethylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC(C)C=2C=CC(=CC=2)C(F)(F)F)=C1 POXCZVSHFWOHHK-UHFFFAOYSA-N 0.000 claims description 2
- WCFANFOWTKGWNV-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[1-[4-(trifluoromethyl)phenyl]propylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC)NC(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=CC(OC)=C1 WCFANFOWTKGWNV-UHFFFAOYSA-N 0.000 claims description 2
- IBUQXYBAGPSJJO-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[2-(4-methylphenyl)ethylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCCC=2C=CC(C)=CC=2)=C1 IBUQXYBAGPSJJO-UHFFFAOYSA-N 0.000 claims description 2
- UNWNZJPKLZSKCV-RPBOFIJWSA-N 3-methoxy-n-[[5-[4-[[(1s,2r)-2-phenylcyclopropyl]amino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)N[C@@H]2[C@H](C2)C=2C=CC=CC=2)=C1 UNWNZJPKLZSKCV-RPBOFIJWSA-N 0.000 claims description 2
- ZWFPICDMSOAGLH-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[[2-(trifluoromethyl)phenyl]methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C(=CC=CC=2)C(F)(F)F)=C1 ZWFPICDMSOAGLH-UHFFFAOYSA-N 0.000 claims description 2
- HMZNUBAPMAOCOT-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[[3-(trifluoromethyl)phenyl]methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C=C(C=CC=2)C(F)(F)F)=C1 HMZNUBAPMAOCOT-UHFFFAOYSA-N 0.000 claims description 2
- CMSNSJKESAFZTI-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[[3-(trifluoromethylsulfanyl)phenyl]methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C=C(SC(F)(F)F)C=CC=2)=C1 CMSNSJKESAFZTI-UHFFFAOYSA-N 0.000 claims description 2
- XPBMHMIVWLMSSJ-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[[4-(trifluoromethylsulfanyl)phenyl]methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C=CC(SC(F)(F)F)=CC=2)=C1 XPBMHMIVWLMSSJ-UHFFFAOYSA-N 0.000 claims description 2
- WQYNKWNGMHSGNT-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NCC=2C=NC(=CC=2)C(F)(F)F)=C1 WQYNKWNGMHSGNT-UHFFFAOYSA-N 0.000 claims description 2
- BLHCGACBVVBQJQ-GOSISDBHSA-N 4-chloro-n-[[5-[(3r)-3-[(hexylamino)methyl]pyrrolidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1[C@@H](CNCCCCCC)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 BLHCGACBVVBQJQ-GOSISDBHSA-N 0.000 claims description 2
- ISDZJHKRZJOPFG-GOSISDBHSA-N 4-chloro-n-[[5-[(3r)-3-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]pyrrolidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC[C@@H]1CN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 ISDZJHKRZJOPFG-GOSISDBHSA-N 0.000 claims description 2
- PJRYNEPWNXFQGP-UHFFFAOYSA-N 4-chloro-n-[[5-[2-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]pyrrolidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNCC1N(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CCC1 PJRYNEPWNXFQGP-UHFFFAOYSA-N 0.000 claims description 2
- ZMWLJQDAWIGXOC-UHFFFAOYSA-N 4-chloro-n-[[5-[3-(2-pyridin-2-ylethylamino)pyrrolidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CC(CC2)NCCC=2N=CC=CC=2)S1 ZMWLJQDAWIGXOC-UHFFFAOYSA-N 0.000 claims description 2
- QFDUJWBLOQNNFF-UHFFFAOYSA-N 4-chloro-n-[[5-[3-[(1-hydroxycyclohexyl)methylamino]pyrrolidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1CN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1NCC1(O)CCCCC1 QFDUJWBLOQNNFF-UHFFFAOYSA-N 0.000 claims description 2
- JUECCJMELXTEIW-UHFFFAOYSA-N 4-chloro-n-[[5-[3-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNCC1CN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CCC1 JUECCJMELXTEIW-UHFFFAOYSA-N 0.000 claims description 2
- BNBVRPMOIVJFGS-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[(4-propylphenyl)methylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(CCC)=CC=C1CNC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 BNBVRPMOIVJFGS-UHFFFAOYSA-N 0.000 claims description 2
- OPNYMHLOHHVHJC-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[1-[4-(trifluoromethyl)phenyl]ethylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C)NC(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 OPNYMHLOHHVHJC-UHFFFAOYSA-N 0.000 claims description 2
- DIDQABDFIWEKRS-UHFFFAOYSA-N 4-chloro-n-[[5-[4-[2-[4-(trifluoromethyl)phenyl]propan-2-ylamino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C)(C)NC(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 DIDQABDFIWEKRS-UHFFFAOYSA-N 0.000 claims description 2
- ZPKZTRKUOSQDAN-GOSISDBHSA-N 4-chloro-n-[[5-[4-[[(1r)-1-cyclohexylethyl]amino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound N([C@H](C)C1CCCCC1)C(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 ZPKZTRKUOSQDAN-GOSISDBHSA-N 0.000 claims description 2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero 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
- C07D413/14—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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00810887A EP1193268A1 (en) | 2000-09-27 | 2000-09-27 | Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases |
PCT/IB2001/001772 WO2002026733A2 (en) | 2000-09-27 | 2001-09-27 | sHARMACEUTICALLY ACTIVE SULFONAMIDE DERIVATIVES BEARING BOTH LIPOPHILIC AND IONISABLE MOIETIES AS INHIBITORS OF PROTEIN JUNKINASES |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20030214A2 true HRP20030214A2 (en) | 2005-02-28 |
Family
ID=8174937
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20030214A HRP20030214A2 (en) | 2000-09-27 | 2003-03-20 | Pharmaceutically active sulfonamide derivatives bearing both lipohilic and ionisable moieties as inhibitors of protein junkinases |
Country Status (27)
Country | Link |
---|---|
US (1) | US7544700B2 (es) |
EP (2) | EP1193268A1 (es) |
JP (1) | JP4927304B2 (es) |
KR (1) | KR20030057532A (es) |
CN (1) | CN1288150C (es) |
AR (1) | AR033999A1 (es) |
AU (2) | AU8799101A (es) |
BG (1) | BG107633A (es) |
BR (1) | BR0114223A (es) |
CA (1) | CA2421209A1 (es) |
CZ (1) | CZ2003884A3 (es) |
EA (1) | EA005819B1 (es) |
EE (1) | EE200300119A (es) |
ES (1) | ES2438185T3 (es) |
HK (1) | HK1072768A1 (es) |
HR (1) | HRP20030214A2 (es) |
HU (1) | HUP0302980A3 (es) |
IL (1) | IL154965A0 (es) |
MX (1) | MXPA03002568A (es) |
NO (1) | NO20031375D0 (es) |
NZ (1) | NZ524542A (es) |
PL (1) | PL361687A1 (es) |
SK (1) | SK3662003A3 (es) |
UA (1) | UA75891C2 (es) |
WO (1) | WO2002026733A2 (es) |
YU (1) | YU21803A (es) |
ZA (1) | ZA200301746B (es) |
Families Citing this family (48)
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EP1193256A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active benzsulfonamide derivatives as inhibitors of JNK proteins |
EP1193267A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active hydrophilic sulfonamide derivatives as inhibitors of protein JunKinases |
EP1193268A1 (en) | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases |
AU2002331253B2 (en) * | 2001-07-23 | 2008-04-03 | Laboratoires Serono Sa | Arylsulfonamide derivatives as C-JUN-N-terminal kinases (JNK'S) inhibitors |
ATE551997T1 (de) * | 2003-09-12 | 2012-04-15 | Merck Serono Sa | Sulfonamid-derivate zur behandlung von diabetes |
PL1701940T3 (pl) * | 2003-12-23 | 2008-11-28 | H Lundbeck As | Pochodne 2-(1H-indolilosulfanylo)benzyloaminy jako SSRI |
AR052308A1 (es) * | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
US7629473B2 (en) * | 2005-06-17 | 2009-12-08 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-aryl amine derivatives |
AR054393A1 (es) * | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos. |
BRPI0613042A2 (pt) | 2005-07-15 | 2010-12-14 | Serono Lab | inibidores de jnk para o tratamento de endometriose |
KR20080044836A (ko) | 2005-07-15 | 2008-05-21 | 라보라뚜와르 세로노 에스. 에이. | 자궁내막증 치료용 jnk 억제제 |
AU2011265521B8 (en) * | 2005-07-15 | 2014-05-22 | Merck Serono Sa | JNK inhibitors for the treatment of endometreosis |
JP2009538882A (ja) * | 2006-06-02 | 2009-11-12 | メルク セローノ ソシエテ アノニム | 皮膚疾患の治療のためのjnk阻害物質 |
EP2361242B1 (en) | 2008-10-17 | 2018-08-01 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
US8993808B2 (en) | 2009-01-21 | 2015-03-31 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
EP2480528B1 (en) | 2009-09-25 | 2018-08-29 | Oryzon Genomics, S.A. | Lysine specific demethylase-1 inhibitors and their use |
US8946296B2 (en) | 2009-10-09 | 2015-02-03 | Oryzon Genomics S.A. | Substituted heteroaryl- and aryl-cyclopropylamine acetamides and their use |
US9616058B2 (en) | 2010-02-24 | 2017-04-11 | Oryzon Genomics, S.A. | Potent selective LSD1 inhibitors and dual LSD1/MAO-B inhibitors for antiviral use |
WO2011106573A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
MX2012012111A (es) | 2010-04-19 | 2013-05-30 | Oryzon Genomics Sa | Inhibidores de demetilasa-1 especifica de lisina y su uso. |
JP6054868B2 (ja) | 2010-07-29 | 2016-12-27 | オリゾン・ジェノミックス・ソシエダッド・アノニマOryzon Genomics S.A. | Lsd1のアリールシクロプロピルアミンをベースとしたデメチラーゼ阻害剤およびそれらの医学的使用 |
WO2012013727A1 (en) | 2010-07-29 | 2012-02-02 | Oryzon Genomics S.A. | Cyclopropylamine derivatives useful as lsd1 inhibitors |
WO2012045883A1 (en) | 2010-10-08 | 2012-04-12 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
EP2712315B1 (en) | 2011-02-08 | 2021-11-24 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
US20140296255A1 (en) * | 2011-05-19 | 2014-10-02 | Oryzong Genomics, S.A. | Lysine demethylase inhibitors for thrombosis and cardiovascular diseases |
EP2741741A2 (en) * | 2011-05-19 | 2014-06-18 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for inflammatory diseases or conditions |
US9469597B2 (en) | 2011-10-20 | 2016-10-18 | Oryzon Genomics S.A. | (Hetero)aryl cyclopropylamine compounds as LSD1 inhibitors |
CN104203914B (zh) | 2011-10-20 | 2017-07-11 | 奥瑞泽恩基因组学股份有限公司 | 作为lsd1抑制剂的(杂)芳基环丙胺化合物 |
KR101939710B1 (ko) | 2011-12-21 | 2019-01-17 | 노비라 테라퓨틱스, 인코포레이티드 | B형 간염의 항바이러스성 제제 |
KR20210081451A (ko) | 2012-08-28 | 2021-07-01 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 설파모일-아릴아미드 및 b형 간염 치료제로서의 그 용도 |
WO2014131847A1 (en) | 2013-02-28 | 2014-09-04 | Janssen R&D Ireland | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b |
PT2981536T (pt) | 2013-04-03 | 2017-08-09 | Janssen Sciences Ireland Uc | Derivados de n-fenil-carboxamida e sua utilização como medicamentos para o tratamento da hepatite b |
JO3603B1 (ar) | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي |
JP6441315B2 (ja) | 2013-05-17 | 2018-12-19 | ヤンセン・サイエンシズ・アイルランド・ユーシー | スルファモイルチオフェンアミド誘導体およびb型肝炎を治療するための医薬品としてのその使用 |
WO2015011281A1 (en) | 2013-07-25 | 2015-01-29 | Janssen R&D Ireland | Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
DK3060547T3 (en) | 2013-10-23 | 2018-01-15 | Janssen Sciences Ireland Uc | CARBOXAMIDE DERIVATIVES AND USE THEREOF AS MEDICINES FOR TREATMENT OF HEPATITS B |
US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
US9169212B2 (en) | 2014-01-16 | 2015-10-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
CA2936947A1 (en) | 2014-02-05 | 2015-08-13 | Novira Therapeutics, Inc. | Combination therapy for treatment of hbv infections |
US11078193B2 (en) | 2014-02-06 | 2021-08-03 | Janssen Sciences Ireland Uc | Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
JP2018510159A (ja) | 2015-03-19 | 2018-04-12 | ノヴィラ・セラピューティクス・インコーポレイテッド | アゾカン及びアゾナン誘導体及びb型肝炎感染症の治療法 |
US10875876B2 (en) | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
JP6845231B2 (ja) | 2015-09-29 | 2021-03-17 | ノヴィラ・セラピューティクス・インコーポレイテッド | B型肝炎抗ウイルス薬の結晶形態 |
JP2019511542A (ja) | 2016-04-15 | 2019-04-25 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | カプシド集合阻害剤を含む組み合わせ及び方法 |
AU2019235522A1 (en) | 2018-03-14 | 2020-09-03 | Janssen Sciences Ireland Unlimited Company | Capsid assembly modulator dosing regimen |
US11096931B2 (en) | 2019-02-22 | 2021-08-24 | Janssen Sciences Ireland Unlimited Company | Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases |
AU2020269897A1 (en) | 2019-05-06 | 2021-10-14 | Janssen Sciences Ireland Unlimited Company | Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases |
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FR2553414B1 (fr) * | 1983-10-18 | 1986-08-14 | Choay Sa | Nouveaux benzenesulfonamides n-cyclises, leur procede de preparation et leur utilisation comme substance active de compositions pharmaceutiques |
US5238950A (en) * | 1991-12-17 | 1993-08-24 | Schering Corporation | Inhibitors of platelet-derived growth factor |
US5744320A (en) | 1995-06-07 | 1998-04-28 | Promega Corporation | Quenching reagents and assays for enzyme-mediated luminescence |
CZ370198A3 (cs) * | 1996-05-31 | 1999-05-12 | Pharmacia & Upjohn Company | Aryl substituované cyklické aminy jako selektivní dopaminové D3 ligandy |
US6043083A (en) | 1997-04-28 | 2000-03-28 | Davis; Roger J. | Inhibitors of the JNK signal transduction pathway and methods of use |
JP2002512625A (ja) * | 1997-05-29 | 2002-04-23 | メルク エンド カンパニー インコーポレーテッド | 細胞接着阻害薬としての複素環アミド化合物 |
DE19743435A1 (de) * | 1997-10-01 | 1999-04-08 | Merck Patent Gmbh | Benzamidinderivate |
AR019322A1 (es) * | 1998-06-18 | 2002-02-13 | Smithkline Beecham Corp | Derivados de sulfonilo sustituido por heterociclo-etanodionanilina sustituida por heterociclo, composicion farmaceutica que los contiene y su uso para lamanufactura de un medicamento |
CZ302691B6 (cs) * | 1998-07-08 | 2011-09-07 | Sanofi - Aventis Deutschland GmbH | N-Arylamidová sloucenina, zpusob její prípravy, farmaceutický prostredek tuto slouceninu obsahující, tato sloucenina pro použití jako aktivátor a pro použití k terapii nebo profylaxi |
EP1088821A1 (en) * | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives |
EP1193267A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active hydrophilic sulfonamide derivatives as inhibitors of protein JunKinases |
EP1193268A1 (en) | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases |
EP1193256A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active benzsulfonamide derivatives as inhibitors of JNK proteins |
-
2000
- 2000-09-27 EP EP00810887A patent/EP1193268A1/en not_active Withdrawn
-
2001
- 2001-09-27 AU AU8799101A patent/AU8799101A/xx active Pending
- 2001-09-27 JP JP2002531117A patent/JP4927304B2/ja not_active Expired - Fee Related
- 2001-09-27 IL IL15496501A patent/IL154965A0/xx unknown
- 2001-09-27 ZA ZA200301746A patent/ZA200301746B/en unknown
- 2001-09-27 AU AU2001287991A patent/AU2001287991B2/en not_active Ceased
- 2001-09-27 ES ES01967622.0T patent/ES2438185T3/es not_active Expired - Lifetime
- 2001-09-27 AR ARP010104565A patent/AR033999A1/es unknown
- 2001-09-27 YU YU21803A patent/YU21803A/sh unknown
- 2001-09-27 HU HU0302980A patent/HUP0302980A3/hu unknown
- 2001-09-27 SK SK366-2003A patent/SK3662003A3/sk not_active Application Discontinuation
- 2001-09-27 EP EP01967622.0A patent/EP1322642B1/en not_active Expired - Lifetime
- 2001-09-27 PL PL36168701A patent/PL361687A1/xx not_active Application Discontinuation
- 2001-09-27 EA EA200300412A patent/EA005819B1/ru not_active IP Right Cessation
- 2001-09-27 NZ NZ524542A patent/NZ524542A/en unknown
- 2001-09-27 KR KR10-2003-7004265A patent/KR20030057532A/ko not_active Application Discontinuation
- 2001-09-27 WO PCT/IB2001/001772 patent/WO2002026733A2/en active IP Right Grant
- 2001-09-27 CA CA002421209A patent/CA2421209A1/en not_active Abandoned
- 2001-09-27 US US10/381,665 patent/US7544700B2/en not_active Expired - Fee Related
- 2001-09-27 MX MXPA03002568A patent/MXPA03002568A/es not_active Application Discontinuation
- 2001-09-27 CZ CZ2003884A patent/CZ2003884A3/cs unknown
- 2001-09-27 BR BR0114223-2A patent/BR0114223A/pt not_active IP Right Cessation
- 2001-09-27 UA UA2003032606A patent/UA75891C2/uk unknown
- 2001-09-27 EE EEP200300119A patent/EE200300119A/xx unknown
- 2001-09-27 CN CNB01819141XA patent/CN1288150C/zh not_active Expired - Fee Related
-
2003
- 2003-03-13 BG BG107633A patent/BG107633A/bg unknown
- 2003-03-20 HR HR20030214A patent/HRP20030214A2/hr not_active Application Discontinuation
- 2003-03-26 NO NO20031375A patent/NO20031375D0/no not_active Application Discontinuation
-
2005
- 2005-04-29 HK HK05103676A patent/HK1072768A1/xx not_active IP Right Cessation
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