JP2003517035A5 - - Google Patents
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- Publication number
- JP2003517035A5 JP2003517035A5 JP2001545259A JP2001545259A JP2003517035A5 JP 2003517035 A5 JP2003517035 A5 JP 2003517035A5 JP 2001545259 A JP2001545259 A JP 2001545259A JP 2001545259 A JP2001545259 A JP 2001545259A JP 2003517035 A5 JP2003517035 A5 JP 2003517035A5
- Authority
- JP
- Japan
- Prior art keywords
- tricyclo
- ylmethyl
- dec
- chloro
- benzamide
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 description 28
- 150000003839 salts Chemical class 0.000 description 18
- 239000012453 solvate Substances 0.000 description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- -1 — (CH 2 ) 2 OH Chemical group 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- DOURJPOQARHJKG-UHFFFAOYSA-N 2-(1-adamantylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC=C1CC1(C2)CC(C3)CC2CC3C1 DOURJPOQARHJKG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010062016 Immunosuppression Diseases 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- CMZGFAODWYOTIK-UHFFFAOYSA-N 3-[3-[3-(1-adamantylmethylcarbamoyl)-4-chlorophenyl]propylamino]propanoic acid Chemical compound OC(=O)CCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 CMZGFAODWYOTIK-UHFFFAOYSA-N 0.000 description 1
- NUOPTKFCWHSASQ-UHFFFAOYSA-N 5-[3-(2-acetamidoethylamino)propyl]-n-(1-adamantylmethyl)-2-chlorobenzamide Chemical compound CC(=O)NCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 NUOPTKFCWHSASQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PLLJYOASWFROMQ-UHFFFAOYSA-N C1C2CC3CC1CC(C2)(C3)CNC(=O)C4=C(C=CC(=C4)CCCCCCO)Cl Chemical compound C1C2CC3CC1CC(C2)(C3)CNC(=O)C4=C(C=CC(=C4)CCCCCCO)Cl PLLJYOASWFROMQ-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- CBCLDXQCJVAJMX-UHFFFAOYSA-N CC(O)=O.CNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 Chemical compound CC(O)=O.CNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 CBCLDXQCJVAJMX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- VOCUTSHUOGTFRS-UHFFFAOYSA-N acetic acid N-(1-adamantylmethyl)-2-chloro-5-[3-(2-hydroxyethylamino)propyl]benzamide Chemical compound CC(O)=O.OCCNCCCc1ccc(Cl)c(c1)C(=O)NCC12CC3CC(CC(C3)C1)C2 VOCUTSHUOGTFRS-UHFFFAOYSA-N 0.000 description 1
- DZPVZFODYJVJFJ-UHFFFAOYSA-N acetic acid;n-(1-adamantylmethyl)-2-chloro-5-[2-(2-hydroxyethylamino)ethoxymethyl]benzamide Chemical compound CC(O)=O.OCCNCCOCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 DZPVZFODYJVJFJ-UHFFFAOYSA-N 0.000 description 1
- XXRMUGGTWOJDDT-UHFFFAOYSA-N acetic acid;n-(1-adamantylmethyl)-2-chloro-5-[2-(3-hydroxypropylamino)ethoxymethyl]benzamide Chemical compound CC(O)=O.OCCCNCCOCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 XXRMUGGTWOJDDT-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- KODGQHIQJIMYJE-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-(3-hydroxypropyl)benzamide Chemical compound OCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 KODGQHIQJIMYJE-UHFFFAOYSA-N 0.000 description 1
- ALZAVVUMECOZSI-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-(3-oxopropyl)benzamide Chemical compound ClC1=CC=C(CCC=O)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 ALZAVVUMECOZSI-UHFFFAOYSA-N 0.000 description 1
- OJXPXEPWQTZVAI-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(1-methoxypropan-2-ylamino)propyl]benzamide Chemical compound COCC(C)NCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 OJXPXEPWQTZVAI-UHFFFAOYSA-N 0.000 description 1
- MFIRMJHOXBXAHI-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(2-fluoroethylamino)propyl]benzamide Chemical compound FCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 MFIRMJHOXBXAHI-UHFFFAOYSA-N 0.000 description 1
- MIPXMPOARAUMHX-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(2-methoxyethylamino)propyl]benzamide Chemical compound COCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 MIPXMPOARAUMHX-UHFFFAOYSA-N 0.000 description 1
- URSPZFGAJITDAP-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(2-methylsulfanylethylamino)propyl]benzamide Chemical compound CSCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 URSPZFGAJITDAP-UHFFFAOYSA-N 0.000 description 1
- HSQAARMBHJCUOK-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(3-hydroxypropylamino)propyl]benzamide Chemical compound OCCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 HSQAARMBHJCUOK-UHFFFAOYSA-N 0.000 description 1
- FVAKMKCTGRHQED-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(3-methoxypropylamino)propyl]benzamide Chemical compound COCCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 FVAKMKCTGRHQED-UHFFFAOYSA-N 0.000 description 1
- WPYLBGSQVVWLSI-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(4-hydroxybutylamino)propyl]benzamide Chemical compound OCCCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 WPYLBGSQVVWLSI-UHFFFAOYSA-N 0.000 description 1
- VLLKASBMGQJXCX-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(cyclohexylmethylamino)propyl]benzamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C(Cl)=CC=C1CCCNCC1CCCCC1 VLLKASBMGQJXCX-UHFFFAOYSA-N 0.000 description 1
- KGVBRFMFMSCHSC-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(dibutylamino)propyl]benzamide Chemical compound CCCCN(CCCC)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 KGVBRFMFMSCHSC-UHFFFAOYSA-N 0.000 description 1
- RTXICJKAYFOPMU-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(diethylamino)propyl]benzamide Chemical compound CCN(CC)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 RTXICJKAYFOPMU-UHFFFAOYSA-N 0.000 description 1
- WPWVIGLODQFREF-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(dimethylamino)propyl]benzamide Chemical compound CN(C)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 WPWVIGLODQFREF-UHFFFAOYSA-N 0.000 description 1
- KUJMDZQTXKCGRN-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(dipropylamino)propyl]benzamide Chemical compound CCCN(CCC)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 KUJMDZQTXKCGRN-UHFFFAOYSA-N 0.000 description 1
- OZCKIMDZONMXTP-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(methylamino)propoxymethyl]benzamide Chemical compound CNCCCOCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 OZCKIMDZONMXTP-UHFFFAOYSA-N 0.000 description 1
- AMFJDQIZOOYADX-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(prop-2-enylamino)propyl]benzamide Chemical compound ClC1=CC=C(CCCNCC=C)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 AMFJDQIZOOYADX-UHFFFAOYSA-N 0.000 description 1
- LEBSEFNMLKSNLS-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(propan-2-ylamino)propyl]benzamide Chemical compound CC(C)NCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 LEBSEFNMLKSNLS-UHFFFAOYSA-N 0.000 description 1
- YFUADINSZUHXDM-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[(1,3-dihydroxy-2-methylpropan-2-yl)amino]propyl]benzamide Chemical compound OCC(C)(CO)NCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 YFUADINSZUHXDM-UHFFFAOYSA-N 0.000 description 1
- IBAZKQXBOPUHAG-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[(1-hydroxy-2-methylpropan-2-yl)amino]propyl]benzamide Chemical compound OCC(C)(C)NCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 IBAZKQXBOPUHAG-UHFFFAOYSA-N 0.000 description 1
- XIKCGSUZKQXHEL-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[(1-hydroxy-3,3-dimethylbutan-2-yl)amino]propyl]benzamide Chemical compound CC(C)(C)C(CO)NCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 XIKCGSUZKQXHEL-UHFFFAOYSA-N 0.000 description 1
- KOFHBAQYZZMIEU-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[(2-hydroxy-2-methylpropyl)amino]propyl]benzamide Chemical compound CC(C)(O)CNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 KOFHBAQYZZMIEU-UHFFFAOYSA-N 0.000 description 1
- MKXZRZSCMAPJFL-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[(3-hydroxy-2,2-dimethylpropyl)amino]propyl]benzamide Chemical compound OCC(C)(C)CNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 MKXZRZSCMAPJFL-UHFFFAOYSA-N 0.000 description 1
- PEDWTXKEMDFYDK-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[(3-hydroxy-3-methylbutyl)amino]propyl]benzamide Chemical compound CC(C)(O)CCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 PEDWTXKEMDFYDK-UHFFFAOYSA-N 0.000 description 1
- PRMCWINNNHFQOX-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[2-(diethylamino)ethyl-ethylamino]propyl]benzamide Chemical compound CCN(CC)CCN(CC)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 PRMCWINNNHFQOX-UHFFFAOYSA-N 0.000 description 1
- FEFJKTDYUYSKFN-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[2-(diethylamino)ethylamino]propyl]benzamide Chemical compound CCN(CC)CCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 FEFJKTDYUYSKFN-UHFFFAOYSA-N 0.000 description 1
- ZASKZZNWSOEEER-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[2-(dimethylamino)ethyl-methylamino]propyl]benzamide Chemical compound CN(C)CCN(C)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 ZASKZZNWSOEEER-UHFFFAOYSA-N 0.000 description 1
- HDXJDKJTRLPSBA-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[2-(dimethylamino)ethylamino]propyl]benzamide Chemical compound CN(C)CCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 HDXJDKJTRLPSBA-UHFFFAOYSA-N 0.000 description 1
- GUERVOOJPHQCFC-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[2-(methylamino)ethylamino]propyl]benzamide Chemical compound CNCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 GUERVOOJPHQCFC-UHFFFAOYSA-N 0.000 description 1
- QUDBQRDWLQSZOJ-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[2-hydroxyethyl(methyl)amino]propyl]benzamide Chemical compound OCCN(C)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 QUDBQRDWLQSZOJ-UHFFFAOYSA-N 0.000 description 1
- RKOLRPWKMHQZEC-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[2-hydroxyethyl(pentyl)amino]propyl]benzamide Chemical compound CCCCCN(CCO)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 RKOLRPWKMHQZEC-UHFFFAOYSA-N 0.000 description 1
- FXMGORABWISSDO-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[2-hydroxyethyl(propan-2-yl)amino]propyl]benzamide Chemical compound OCCN(C(C)C)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 FXMGORABWISSDO-UHFFFAOYSA-N 0.000 description 1
- WZYBVNQMSMKGID-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[2-hydroxyethyl(propyl)amino]propyl]benzamide Chemical compound CCCN(CCO)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 WZYBVNQMSMKGID-UHFFFAOYSA-N 0.000 description 1
- ONOGEQWODVPGNY-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[3-(dimethylamino)propyl-methylamino]propyl]benzamide Chemical compound CN(C)CCCN(C)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 ONOGEQWODVPGNY-UHFFFAOYSA-N 0.000 description 1
- ZCIJFVSFCDBHPN-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[3-(dimethylamino)propylamino]propyl]benzamide Chemical compound CN(C)CCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 ZCIJFVSFCDBHPN-UHFFFAOYSA-N 0.000 description 1
- REMNXCGFIFQTJF-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[3-(methylamino)propoxy]propyl]benzamide Chemical compound CNCCCOCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 REMNXCGFIFQTJF-UHFFFAOYSA-N 0.000 description 1
- WPWSCNZLYJDLIU-SGGRRFJASA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[[(2r)-1-hydroxypropan-2-yl]amino]propyl]benzamide Chemical compound OC[C@@H](C)NCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 WPWSCNZLYJDLIU-SGGRRFJASA-N 0.000 description 1
- FQBLVXGLXZCJCC-SGGRRFJASA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[[(2r)-2-hydroxypropyl]amino]propyl]benzamide Chemical compound C[C@@H](O)CNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 FQBLVXGLXZCJCC-SGGRRFJASA-N 0.000 description 1
- FQBLVXGLXZCJCC-QNHAZURESA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[[(2s)-2-hydroxypropyl]amino]propyl]benzamide Chemical compound C[C@H](O)CNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 FQBLVXGLXZCJCC-QNHAZURESA-N 0.000 description 1
- KVPZRGGEXRCYHP-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[cyclohexyl(2-hydroxyethyl)amino]propyl]benzamide Chemical compound C=1C=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=CC=1CCCN(CCO)C1CCCCC1 KVPZRGGEXRCYHP-UHFFFAOYSA-N 0.000 description 1
- FNJVVNCHZGNKDU-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[ethyl(2-hydroxyethyl)amino]propyl]benzamide Chemical compound OCCN(CC)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 FNJVVNCHZGNKDU-UHFFFAOYSA-N 0.000 description 1
- BGVWZURLAAYUIN-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[ethyl(propyl)amino]propyl]benzamide Chemical compound CCCN(CC)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 BGVWZURLAAYUIN-UHFFFAOYSA-N 0.000 description 1
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- XRWMKFAJLXCBHC-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[methyl(propan-2-yl)amino]propyl]benzamide Chemical compound CC(C)N(C)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 XRWMKFAJLXCBHC-UHFFFAOYSA-N 0.000 description 1
- FZGXKBZRVCJCRP-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[[(3-hydroxy-2,2-dimethylpropyl)amino]methyl]benzamide Chemical compound OCC(C)(C)CNCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 FZGXKBZRVCJCRP-UHFFFAOYSA-N 0.000 description 1
- NOPBFRYUXZIMSD-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[[2-(2-hydroxyethoxy)ethylamino]methyl]benzamide Chemical compound OCCOCCNCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 NOPBFRYUXZIMSD-UHFFFAOYSA-N 0.000 description 1
- DIXZPRGCOJDSGB-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[[2-(2-hydroxyethylamino)ethylamino]methyl]benzamide;dihydrochloride Chemical compound Cl.Cl.OCCNCCNCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 DIXZPRGCOJDSGB-UHFFFAOYSA-N 0.000 description 1
- WCFIZVURQGUCRB-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[[3-(propan-2-ylamino)propylamino]methyl]benzamide Chemical compound CC(C)NCCCNCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 WCFIZVURQGUCRB-UHFFFAOYSA-N 0.000 description 1
- KRINUOJUBOGLDZ-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-[(3-aminopropylamino)methyl]-2-chlorobenzamide Chemical compound NCCCNCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 KRINUOJUBOGLDZ-UHFFFAOYSA-N 0.000 description 1
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- VPZUNBJDAWFUHA-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-[3-(butylamino)propyl]-2-chlorobenzamide Chemical compound CCCCNCCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 VPZUNBJDAWFUHA-UHFFFAOYSA-N 0.000 description 1
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- HDKBKRNOPUZNRS-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-[3-[butyl(2-hydroxyethyl)amino]propyl]-2-chlorobenzamide Chemical compound CCCCN(CCO)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 HDKBKRNOPUZNRS-UHFFFAOYSA-N 0.000 description 1
- DYSSYGMREMOBAZ-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-[3-[butyl(ethyl)amino]propyl]-2-chlorobenzamide Chemical compound CCCCN(CC)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 DYSSYGMREMOBAZ-UHFFFAOYSA-N 0.000 description 1
- RZKHAZWWDMDKOH-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-[3-[butyl(methyl)amino]propyl]-2-chlorobenzamide Chemical compound CCCCN(C)CCCC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 RZKHAZWWDMDKOH-UHFFFAOYSA-N 0.000 description 1
- JFSIHDMLTPMZTF-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-[[(1-aminocyclopropyl)methyl-(2-hydroxyethyl)amino]methyl]-2-chlorobenzamide Chemical compound C=1C=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=CC=1CN(CCO)CC1(N)CC1 JFSIHDMLTPMZTF-UHFFFAOYSA-N 0.000 description 1
- FPXGCTSZYBMRQF-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-[[2-hydroxyethyl-[2-(methylamino)ethyl]amino]methyl]-2-methylbenzamide Chemical compound CNCCN(CCO)CC1=CC=C(C)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 FPXGCTSZYBMRQF-UHFFFAOYSA-N 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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| GB0017942.4 | 2000-07-22 | ||
| GB0017942A GB0017942D0 (en) | 2000-07-22 | 2000-07-22 | Novel compounds |
| PCT/SE2000/002505 WO2001044170A1 (en) | 1999-12-17 | 2000-12-12 | Adamantane derivatives |
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| SE9904738D0 (sv) | 1999-12-22 | 1999-12-22 | Astra Pharma Prod | Novel compounds |
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| PA8557501A1 (es) | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
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| PA8591801A1 (es) | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
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| MXPA05012086A (es) * | 2003-05-12 | 2006-02-22 | Pfizer Prod Inc | Inhibidores de benzamida del receptor p2x7. |
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| WO2004105797A1 (en) * | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine |
| EP1644042A1 (en) * | 2003-05-29 | 2006-04-12 | AstraZeneca AB | A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate |
| SE0302192D0 (sv) * | 2003-08-08 | 2003-08-08 | Astrazeneca Ab | Novel compounds |
| SE0302488D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | New combination |
| BRPI0512915A (pt) * | 2004-06-29 | 2008-04-15 | Warner Lambert Co | terapias de combinação utilizando inibidores benzamida do receptor p2x7 |
| WO2006003500A1 (en) * | 2004-06-29 | 2006-01-12 | Pfizer Products Inc. | Method for preparing 5-`4-(2-hydroxy-propyl)-3,5-dioxo-4,5-dihydro-3h`1,2,4!triazin-2-yl!-benzamide derivatives by deprotecting the hydroxyl-protected precursers |
| SA05260265A (ar) * | 2004-08-30 | 2005-12-03 | استرازينيكا ايه بي | مركبات جديدة |
| US20060063834A1 (en) * | 2004-09-09 | 2006-03-23 | Frangioni John V | Substituted adamantanes, and methods of making the same |
| SE0402925D0 (sv) * | 2004-11-30 | 2004-11-30 | Astrazeneca Ab | Novel Compounds |
| US20080207577A1 (en) * | 2005-07-11 | 2008-08-28 | Astrazeneca Ab | Combination I |
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| TW200819416A (en) * | 2006-09-05 | 2008-05-01 | Astrazeneca Ab | Novel process 470 |
| HRP20120968T1 (hr) | 2008-02-06 | 2013-01-31 | Astrazeneca Ab | Spojevi |
| CN102046240B (zh) | 2008-03-25 | 2014-06-25 | 阿费克蒂斯药品公司 | 新的p2x7r拮抗剂及其应用 |
| WO2010118921A1 (en) | 2009-04-14 | 2010-10-21 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| GB2469915A (en) * | 2009-04-30 | 2010-11-03 | Astrazeneca Ab | 2-chloro-5-[3-[(3-hydroxypropyl)amino]propyl]-N-(tricyclo[3.3.1.13,7]dec- 1-ylmethyl)-benzamide hydrochloride salt |
| GB0913342D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | Compounds - 801 |
| EP2322149A1 (en) | 2009-11-03 | 2011-05-18 | Universidad del Pais Vasco | Methods and compositions for the treatment of ischemia |
| EP2569281A1 (en) | 2010-05-14 | 2013-03-20 | Affectis Pharmaceuticals AG | Novel methods for the preparation of p2x7r antagonists |
| JP2013249256A (ja) * | 2010-09-15 | 2013-12-12 | Astellas Pharma Inc | 脂肪性肝疾患治療薬 |
| WO2012110190A1 (en) | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163456A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| CN103687860B (zh) | 2011-07-22 | 2016-06-08 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的杂环酰胺衍生物 |
| EA024204B1 (ru) | 2012-01-20 | 2016-08-31 | Актелион Фармасьютиклз Лтд. | Производные гетероциклических амидов в качестве антагонистов p2xрецептора |
| AR093921A1 (es) | 2012-12-12 | 2015-06-24 | Actelion Pharmaceuticals Ltd | Derivados de indol carboxamida como antagonistas del receptor p2x7 |
| KR102232744B1 (ko) | 2012-12-18 | 2021-03-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ２ｘ７ 수용체 길항제로서의 인돌 카르복사미드 유도체 |
| ES2616883T3 (es) | 2013-01-22 | 2017-06-14 | Actelion Pharmaceuticals Ltd. | Derivados amida heterocíclicos como antagonistas del receptor P2X7 |
| KR102222220B1 (ko) | 2013-01-22 | 2021-03-03 | 이도르시아 파마슈티컬스 리미티드 | Ｐ2ｘ7 수용체 길항제로서의 헤테로시클릭 아미드 유도체 |
| EP4479366A4 (en) * | 2022-02-15 | 2026-03-25 | Childrens Medical Ct Corp | COMPOSITIONS AND METHODS RELATING TO THE INHIBITION OF ATP/P2X7R SIGNALING |
| EP4230196A1 (en) | 2022-02-21 | 2023-08-23 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of dystrophinopathies |
| WO2025024881A1 (en) * | 2023-07-28 | 2025-02-06 | The University Of Sydney | Adamantyl p2x7 receptor antagonists and their use in the treatment of cardiovascular diseases |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029241A (en) | 1962-04-10 | Phenylpbperazinylacyl anilines | ||
| US3464998A (en) | 1968-03-04 | 1969-09-02 | Searle & Co | Adamantyl esters and amides of pyridinecarboxylic acids |
| US3732305A (en) | 1970-03-03 | 1973-05-08 | Us Army | S-substituted thiosulfuric acid derivatives and preparation thereof |
| US3789072A (en) | 1970-04-22 | 1974-01-29 | Squibb & Sons Inc | Carboxamides |
| FR2346011A1 (fr) | 1976-02-02 | 1977-10-28 | Orsymonde | Acetanilido-piperazines |
| ZA825719B (en) | 1981-09-03 | 1983-06-29 | Recordati Chem Pharm | Alkanoylanilides |
| CA2015473C (en) | 1989-04-28 | 1998-04-14 | Iwao Kinoshita | Triphenylmethane derivatives |
| US6021024A (en) * | 1992-02-21 | 2000-02-01 | Kabushiki Kaisha Toshiba | Magnetic disk drive having a constant skew angle |
| CA2091194A1 (en) | 1992-04-08 | 1993-10-09 | Richard D. Connell | 2-oxo-ethyl derivatives as immunosuppressants |
| EP0582164B1 (en) | 1992-07-31 | 1998-12-23 | Bristol-Myers Squibb Company | Adenosine re-uptake inhibiting derivatives of diphenyl oxazoles, thiazoles and imidazoles |
| PL181782B1 (pl) | 1993-08-10 | 2001-09-28 | Black James Foundation | Nowe zwiazki i sposób wytwarzania nowych zwiazków PL |
| US5530018A (en) * | 1994-02-04 | 1996-06-25 | G. D. Searle & Co. | Meso-azanoradamantanes |
| GB9409150D0 (en) | 1994-05-09 | 1994-06-29 | Black James Foundation | Cck and gastrin receptor ligands |
| WO1995032949A1 (en) | 1994-05-27 | 1995-12-07 | James Black Foundation Limited | Gastrin and cck antagonists |
| JP2002515008A (ja) | 1994-10-27 | 2002-05-21 | メルク エンド カンパニー インコーポレーテッド | ムスカリン・アンタゴニスト |
| DE19608653A1 (de) | 1996-03-06 | 1997-09-11 | Thomae Gmbh Dr K | Pyrimido[5,4-d]pyrimidine, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| SE9704546D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| WO1999029640A2 (en) * | 1997-12-05 | 1999-06-17 | Eisai Co., Ltd. | Compositions and methods for modulating the activity of fibroblast growth factor |
| SE9704544D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| SE9704545D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| US6018089A (en) * | 1997-12-09 | 2000-01-25 | Shell Oil Company | Process for separating linear internal olefins from branched internal olefins |
| AU1924099A (en) | 1997-12-18 | 1999-07-05 | Lyonnaise Industrielle Pharmaceutique (Lipha) | Piperazine derivatives useful as hypoglycemic agents |
| US6271265B1 (en) | 1998-05-19 | 2001-08-07 | Centaur Pharmaceuticals, Inc. | Amide therapeutics for the treatment of inflammatory bowel disease |
| CN1147483C (zh) | 1999-04-09 | 2004-04-28 | 阿斯特拉曾尼卡有限公司 | 金刚烷衍生物 |
| SE9901875D0 (sv) | 1999-05-25 | 1999-05-25 | Astra Pharma Prod | Novel compounds |
| SE9904505D0 (sv) | 1999-12-09 | 1999-12-09 | Astra Pharma Prod | Novel compounds |
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| US6555451B1 (en) * | 2001-09-28 | 2003-04-29 | The United States Of America As Represented By The Secretary Of The Navy | Method for making shallow diffusion junctions in semiconductors using elemental doping |
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- 2000-12-12 TR TR2004/01432T patent/TR200401432T4/xx unknown
- 2000-12-12 AT AT00986155T patent/ATE261933T1/de active
- 2000-12-12 EE EEP200200330A patent/EE05134B1/xx not_active IP Right Cessation
- 2000-12-12 CO CO00094336A patent/CO5251381A1/es not_active Application Discontinuation
- 2000-12-12 EP EP07014968A patent/EP1862451A1/en not_active Withdrawn
- 2000-12-12 DE DE60034155T patent/DE60034155T2/de not_active Expired - Lifetime
- 2000-12-12 DK DK00986155T patent/DK1242364T3/da active
- 2000-12-12 AU AU22444/01A patent/AU780506B2/en not_active Expired
- 2000-12-12 EP EP03013989A patent/EP1352895B1/en not_active Expired - Lifetime
- 2000-12-12 IL IL15012400A patent/IL150124A0/xx not_active IP Right Cessation
- 2000-12-12 US US10/149,549 patent/US6881754B2/en not_active Expired - Lifetime
- 2000-12-12 EP EP00986155A patent/EP1242364B1/en not_active Expired - Lifetime
- 2000-12-12 AT AT03013991T patent/ATE350364T1/de active
- 2000-12-12 EP EP03013991A patent/EP1352897B1/en not_active Expired - Lifetime
- 2000-12-12 SK SK841-2002A patent/SK286987B6/sk not_active IP Right Cessation
- 2000-12-12 DK DK03013991T patent/DK1352897T3/da active
- 2000-12-12 HK HK02108164.1A patent/HK1046678B/en not_active IP Right Cessation
- 2000-12-12 MX MXPA02005789A patent/MXPA02005789A/es active IP Right Grant
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- 2000-12-12 JP JP2001545259A patent/JP3710418B2/ja not_active Expired - Lifetime
- 2000-12-12 PT PT03013990T patent/PT1352896E/pt unknown
- 2000-12-12 CZ CZ20022093A patent/CZ20022093A3/cs unknown
- 2000-12-12 NZ NZ519378A patent/NZ519378A/en not_active IP Right Cessation
- 2000-12-12 DE DE60009147T patent/DE60009147T2/de not_active Expired - Lifetime
- 2000-12-12 AT AT03013990T patent/ATE376994T1/de active
- 2000-12-12 ES ES00986155T patent/ES2215777T3/es not_active Expired - Lifetime
- 2000-12-12 WO PCT/SE2000/002505 patent/WO2001044170A1/en not_active Ceased
- 2000-12-12 ES ES03013990T patent/ES2294219T3/es not_active Expired - Lifetime
- 2000-12-12 EP EP03013990A patent/EP1352896B1/en not_active Expired - Lifetime
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- 2000-12-12 SI SI200030950T patent/SI1352895T1/sl unknown
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- 2000-12-12 PT PT00986155T patent/PT1242364E/pt unknown
- 2000-12-12 DE DE60032823T patent/DE60032823T2/de not_active Expired - Lifetime
- 2000-12-12 KR KR1020027007702A patent/KR100710110B1/ko not_active Expired - Lifetime
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2002
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- 2002-06-14 NO NO20022856A patent/NO328682B1/no not_active IP Right Cessation
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2004
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2005
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- 2005-06-03 JP JP2005163710A patent/JP2005320340A/ja active Pending
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2006
- 2006-09-29 US US11/529,746 patent/US7297818B2/en not_active Expired - Fee Related
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2007
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- 2007-06-20 US US11/812,673 patent/US20080139636A1/en not_active Abandoned
- 2007-12-19 CY CY20071101609T patent/CY1107838T1/el unknown
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2008
- 2008-02-25 IL IL189758A patent/IL189758A0/en not_active IP Right Cessation
- 2008-12-04 US US12/314,156 patent/US20090176853A1/en not_active Abandoned
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