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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- 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
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- 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
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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
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- 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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| US20070281931A1 (en) * | 2003-05-29 | 2007-12-06 | Nigel Boughton-Smith | Pharmaceutical Composition Containing a P2x7 Receptor Antagonist and Methotrexate |
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| SA05260265A (ar) * | 2004-08-30 | 2005-12-03 | استرازينيكا ايه بي | مركبات جديدة |
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| EP2242759B1 (en) | 2008-02-06 | 2012-09-12 | AstraZeneca AB | Compounds |
| PL2105164T3 (pl) | 2008-03-25 | 2011-05-31 | Affectis Pharmaceuticals Ag | Nowi antagoniści P2X7R i ich zastosowanie |
| SI2243772T1 (sl) | 2009-04-14 | 2012-05-31 | Affectis Pharmaceuticals Ag | Novi antagonisti p x r in njihova uporaba |
| 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 |
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| EP2322149A1 (en) | 2009-11-03 | 2011-05-18 | Universidad del Pais Vasco | Methods and compositions for the treatment of ischemia |
| JP2013526496A (ja) | 2010-05-14 | 2013-06-24 | アフェクティス ファーマシューティカルズ アーゲー | Ｐ２ｘ７ｒ拮抗剤の新規調製方法 |
| 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 |
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| WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| BR112014001454A2 (pt) | 2011-07-22 | 2017-06-27 | Actelion Pharmaceuticals Ltd | derivados de amidas heterocíclicas como antagonistas do receptor de p2x7 |
| NZ628910A (en) | 2012-01-20 | 2016-02-26 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| WO2014091415A1 (en) | 2012-12-12 | 2014-06-19 | Actelion Pharmaceuticals Ltd | Indole carboxamide derivatives as p2x7 receptor antagonists |
| CN104854087B (zh) | 2012-12-18 | 2017-03-22 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的吲哚羧酰胺衍生物 |
| ES2616883T3 (es) | 2013-01-22 | 2017-06-14 | Actelion Pharmaceuticals Ltd. | Derivados amida heterocíclicos como antagonistas del receptor P2X7 |
| WO2014115072A1 (en) | 2013-01-22 | 2014-07-31 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| US20250129093A1 (en) * | 2022-02-15 | 2025-04-24 | The Children's Medical Center Corporation | Compositions and methods relating to atp/p2x7r signaling inhibition |
| 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 |
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- 2000-12-12 HK HK02108164.1A patent/HK1046678B/en not_active IP Right Cessation
- 2000-12-12 PL PL355913A patent/PL200836B1/pl not_active IP Right Cessation
- 2000-12-12 PT PT03013991T patent/PT1352897E/pt unknown
- 2000-12-12 CO CO00094336A patent/CO5251381A1/es not_active Application Discontinuation
- 2000-12-12 AT AT03013990T patent/ATE376994T1/de active
- 2000-12-12 PT PT00986155T patent/PT1242364E/pt unknown
- 2000-12-12 PT PT03013990T patent/PT1352896E/pt unknown
- 2000-12-12 NZ NZ519378A patent/NZ519378A/en not_active IP Right Cessation
- 2000-12-12 ES ES03013991T patent/ES2279031T3/es not_active Expired - Lifetime
- 2000-12-12 EP EP00986155A patent/EP1242364B1/en not_active Expired - Lifetime
- 2000-12-12 AT AT00986155T patent/ATE261933T1/de active
- 2000-12-12 KR KR1020027007702A patent/KR100710110B1/ko not_active Expired - Lifetime
- 2000-12-12 EE EEP200200330A patent/EE05134B1/xx not_active IP Right Cessation
- 2000-12-12 SK SK841-2002A patent/SK286987B6/sk not_active IP Right Cessation
- 2000-12-12 ES ES03013990T patent/ES2294219T3/es not_active Expired - Lifetime
- 2000-12-12 AT AT03013989T patent/ATE358117T1/de active
- 2000-12-12 HU HU0300616A patent/HUP0300616A3/hu unknown
- 2000-12-12 KR KR1020077000596A patent/KR20070012883A/ko not_active Ceased
- 2000-12-12 DE DE60032823T patent/DE60032823T2/de not_active Expired - Lifetime
- 2000-12-12 BR BRPI0016395A patent/BRPI0016395B8/pt not_active IP Right Cessation
- 2000-12-12 SI SI200030950T patent/SI1352895T1/sl unknown
- 2000-12-12 CN CNB008189226A patent/CN1312120C/zh not_active Expired - Lifetime
- 2000-12-12 DE DE60034155T patent/DE60034155T2/de not_active Expired - Lifetime
- 2000-12-12 ES ES03013989T patent/ES2282546T3/es not_active Expired - Lifetime
- 2000-12-12 DK DK03013990T patent/DK1352896T3/da active
- 2000-12-12 US US10/149,549 patent/US6881754B2/en not_active Expired - Lifetime
- 2000-12-12 IL IL15012400A patent/IL150124A0/xx not_active IP Right Cessation
- 2000-12-12 EP EP03013990A patent/EP1352896B1/en not_active Expired - Lifetime
- 2000-12-12 CA CA2393352A patent/CA2393352C/en not_active Expired - Lifetime
- 2000-12-12 EP EP07014968A patent/EP1862451A1/en not_active Withdrawn
- 2000-12-12 EP EP03013989A patent/EP1352895B1/en not_active Expired - Lifetime
- 2000-12-12 EP EP03013991A patent/EP1352897B1/en not_active Expired - Lifetime
- 2000-12-12 AU AU22444/01A patent/AU780506B2/en not_active Expired
- 2000-12-12 ES ES00986155T patent/ES2215777T3/es not_active Expired - Lifetime
- 2000-12-12 DE DE60036968T patent/DE60036968T2/de not_active Expired - Lifetime
- 2000-12-15 MY MYPI20005926A patent/MY125978A/en unknown
- 2000-12-15 AR ARP000106695A patent/AR035325A1/es active IP Right Grant
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2002
- 2002-05-31 IS IS6406A patent/IS2246B/is unknown
- 2002-06-14 NO NO20022856A patent/NO328682B1/no not_active IP Right Cessation
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2004
- 2004-03-31 US US10/813,426 patent/US7132457B2/en not_active Expired - Lifetime
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2005
- 2005-05-27 AU AU2005202321A patent/AU2005202321B2/en not_active Ceased
- 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
- 2007-03-06 CY CY20071100312T patent/CY1106357T1/el unknown
- 2007-05-17 CY CY20071100671T patent/CY1106602T1/el unknown
- 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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