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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- 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
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| BRPI0512915A (pt) * | 2004-06-29 | 2008-04-15 | Warner Lambert Co | terapias de combinação utilizando inibidores benzamida do receptor p2x7 |
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| CN102083839B (zh) | 2008-02-06 | 2014-03-26 | 阿斯利康(瑞典)有限公司 | 化合物 |
| AU2009228649B2 (en) | 2008-03-25 | 2014-05-22 | Affectis Pharmaceuticals Ag | Novel P2X7R antagonists and their use |
| DK2243772T3 (da) | 2009-04-14 | 2012-02-13 | Affectis Pharmaceuticals Ag | Hidtil ukendte P2X7R-antagonister og deres anvendelse |
| 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 |
| EP2386541A1 (en) | 2010-05-14 | 2011-11-16 | 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 |
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| WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| MX2014000894A (es) | 2011-07-22 | 2014-02-27 | Actelion Pharmaceuticals Ltd | Derivados de amidas heterociclicas como antagonistas de receptores p2x7. |
| TWI576347B (zh) | 2012-01-20 | 2017-04-01 | 艾克泰聯製藥有限公司 | 作為ｐ２ｘ受體拮抗劑之雜環醯胺衍生物 |
| KR102232742B1 (ko) | 2012-12-12 | 2021-03-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ２ｘ７ 수용체 길항제로서의 인돌 카르복사미드 유도체 |
| WO2014097140A1 (en) | 2012-12-18 | 2014-06-26 | Actelion Pharmaceuticals Ltd | Indole carboxamide derivatives as p2x7 receptor antagonists |
| JP6282016B2 (ja) | 2013-01-22 | 2018-02-21 | イドーシア ファーマシューティカルズ リミテッドＩｄｏｒｓｉａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | Ｐ２ｘ７受容体アンタゴニストとしての複素環アミド誘導体 |
| JP6282017B2 (ja) | 2013-01-22 | 2018-02-21 | イドーシア ファーマシューティカルズ リミテッドＩｄｏｒｓｉａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | Ｐ２ｘ７受容体アンタゴニストとしての複素環アミド誘導体 |
| WO2023158601A2 (en) * | 2022-02-15 | 2023-08-24 | 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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| SE9904652D0 (sv) * | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
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- 2000-12-12 DE DE60036968T patent/DE60036968T2/de not_active Expired - Lifetime
- 2000-12-12 AU AU22444/01A patent/AU780506B2/en not_active Expired
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- 2000-12-12 EE EEP200200330A patent/EE05134B1/xx not_active IP Right Cessation
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2002
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2004
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2005
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2006
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2007
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2008
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- 2008-12-04 US US12/314,156 patent/US20090176853A1/en not_active Abandoned
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