JP2009541343A5 - - Google Patents
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- Publication number
- JP2009541343A5 JP2009541343A5 JP2009516686A JP2009516686A JP2009541343A5 JP 2009541343 A5 JP2009541343 A5 JP 2009541343A5 JP 2009516686 A JP2009516686 A JP 2009516686A JP 2009516686 A JP2009516686 A JP 2009516686A JP 2009541343 A5 JP2009541343 A5 JP 2009541343A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxyphenyl
- ethyl
- imidazolidinone
- phenyl
- optionally substituted
- 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.)
- Withdrawn
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- -1 4- (fluoromethyl) phenyl Chemical group 0.000 claims description 158
- 150000001875 compounds Chemical class 0.000 claims description 137
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 150000003839 salts Chemical group 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000006413 ring segment Chemical group 0.000 claims description 15
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 10
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 10
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 8
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 7
- DGRHZXIEFDDSNL-UHFFFAOYSA-N 1-amino-4-(4-cyclopropylphenyl)-3-[3-(4-methoxyphenyl)propyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCCN1C(=O)N(N)CC1C1=CC=C(C2CC2)C=C1 DGRHZXIEFDDSNL-UHFFFAOYSA-N 0.000 claims description 6
- JBTGGVRWHMMGHR-UHFFFAOYSA-N 1-amino-4-(4-methoxyphenyl)-3-[3-(4-methoxyphenyl)propyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCCN1C(=O)N(N)CC1C1=CC=C(OC)C=C1 JBTGGVRWHMMGHR-UHFFFAOYSA-N 0.000 claims description 6
- HOWKRTFNBUTZDR-UHFFFAOYSA-N 1-amino-4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1=CC=C(C(C)(C)C)C=C1 HOWKRTFNBUTZDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- GFFIHDXPUGXVGG-LJQANCHMSA-N n-[(4s)-4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)C[C@@H]1C1=CC=C(OC)C=C1 GFFIHDXPUGXVGG-LJQANCHMSA-N 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- QUDUUHFIQIRFRK-UHFFFAOYSA-N 1-amino-3-[2-(4-methoxyphenyl)ethyl]-4-(4-methylphenyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1=CC=C(C)C=C1 QUDUUHFIQIRFRK-UHFFFAOYSA-N 0.000 claims description 4
- KDJZSRKKXFMSFT-UHFFFAOYSA-N 1-amino-4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1=CC=C(C2CC2)C=C1 KDJZSRKKXFMSFT-UHFFFAOYSA-N 0.000 claims description 4
- ICTWPYQRAMXOLQ-UHFFFAOYSA-N 1-amino-4-(4-methoxyphenyl)-3-(3-phenylpropyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1C1N(CCCC=2C=CC=CC=2)C(=O)N(N)C1 ICTWPYQRAMXOLQ-UHFFFAOYSA-N 0.000 claims description 4
- ANDRPOIUPUQDFB-UHFFFAOYSA-N 1-amino-4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1=CC=C(OC)C=C1 ANDRPOIUPUQDFB-UHFFFAOYSA-N 0.000 claims description 4
- UDDCUQGZSYPWFN-UHFFFAOYSA-N 2-[[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]sulfamoyl]-n,n-bis(2-methoxyethyl)acetamide Chemical compound O=C1N(NS(=O)(=O)CC(=O)N(CCOC)CCOC)CC(C=2C=CC(=CC=2)C2CC2)N1CCC1=CC=C(OC)C=C1 UDDCUQGZSYPWFN-UHFFFAOYSA-N 0.000 claims description 4
- RSDYYXKBNDNKIU-UHFFFAOYSA-N 2-[[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]sulfamoyl]-n-(3-hydroxy-3-methylbutan-2-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(=O)NC(C)C(C)(C)O)CC1C1=CC=C(C2CC2)C=C1 RSDYYXKBNDNKIU-UHFFFAOYSA-N 0.000 claims description 4
- DNVOUGIKUJTZKD-UHFFFAOYSA-N 2-[[4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]sulfamoyl]-n,n-dimethylacetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(=O)N(C)C)CC1C1=CC=C(OC)C=C1 DNVOUGIKUJTZKD-UHFFFAOYSA-N 0.000 claims description 4
- NATLLRLNMXDTDZ-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-(pyridin-4-ylmethylamino)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=CN=CC=2)CC1C1=CC=C(C)C(C)=C1 NATLLRLNMXDTDZ-UHFFFAOYSA-N 0.000 claims description 4
- HFBVSVHWVZGCSH-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)propyl]-2-oxo-1-(sulfamoylamino)imidazolidine Chemical compound C1=CC(OC)=CC=C1C(C)CN1C(=O)N(NS(N)(=O)=O)CC1C1=CC=C(OC)C=C1 HFBVSVHWVZGCSH-UHFFFAOYSA-N 0.000 claims description 4
- OEICIRWHFXGBKJ-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-[3-(4-methoxyphenyl)propyl]-2-oxo-1-(sulfamoylamino)imidazolidine Chemical compound C1=CC(OC)=CC=C1CCCN1C(=O)N(NS(N)(=O)=O)CC1C1=CC=C(OC)C=C1 OEICIRWHFXGBKJ-UHFFFAOYSA-N 0.000 claims description 4
- IJCLHMGBQQIXJP-UHFFFAOYSA-N 4-amino-4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-(pyridin-3-ylmethylsulfonyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(C=2C=CC(=CC=2)C2CC2)(N)CN(S(=O)(=O)CC=2C=NC=CC=2)C1=O IJCLHMGBQQIXJP-UHFFFAOYSA-N 0.000 claims description 4
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 4
- 208000005189 Embolism Diseases 0.000 claims description 4
- 206010019280 Heart failures Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000001435 Thromboembolism Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- GFFIHDXPUGXVGG-IBGZPJMESA-N n-[(4r)-4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)C[C@H]1C1=CC=C(OC)C=C1 GFFIHDXPUGXVGG-IBGZPJMESA-N 0.000 claims description 4
- DDUHZVANACGSEG-NRFANRHFSA-N n-[(4r)-4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)C[C@H]1C1=CC=C(C(C)(C)C)C=C1 DDUHZVANACGSEG-NRFANRHFSA-N 0.000 claims description 4
- WIWRUENDUNEESK-RUZDIDTESA-N n-[(4s)-4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1-phenylmethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC=2C=CC=CC=2)C[C@@H]1C1=CC=C(OC)C=C1 WIWRUENDUNEESK-RUZDIDTESA-N 0.000 claims description 4
- DDUHZVANACGSEG-OAQYLSRUSA-N n-[(4s)-4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)C[C@@H]1C1=CC=C(C(C)(C)C)C=C1 DDUHZVANACGSEG-OAQYLSRUSA-N 0.000 claims description 4
- JFTNAHZEOMLTPQ-UHFFFAOYSA-N n-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(C)C(C)=C1 JFTNAHZEOMLTPQ-UHFFFAOYSA-N 0.000 claims description 4
- BGZGUFWPTLRTAD-UHFFFAOYSA-N n-[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-2-(dimethylsulfamoyl)acetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)CS(=O)(=O)N(C)C)CC1C1=CC=C(C2CC2)C=C1 BGZGUFWPTLRTAD-UHFFFAOYSA-N 0.000 claims description 4
- ROWFQJXJRCOWAH-UHFFFAOYSA-N n-cyclopropyl-2-[[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]sulfamoyl]acetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(=O)NC2CC2)CC1C1=CC=C(C2CC2)C=C1 ROWFQJXJRCOWAH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- LHQXQOPABIJODD-UHFFFAOYSA-N 1-(benzylamino)-4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=CC=CC=2)CC1C1=CC=C(C)C(C)=C1 LHQXQOPABIJODD-UHFFFAOYSA-N 0.000 claims description 2
- UNENWHKEIQELAJ-UHFFFAOYSA-N 1-(benzylamino)-4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=CC=CC=2)CC1C1=CC=C(C(C)(C)C)C=C1 UNENWHKEIQELAJ-UHFFFAOYSA-N 0.000 claims description 2
- WBPIVENMALKVML-UHFFFAOYSA-N 1-(cyclopropylmethylamino)-4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC2CC2)CC1C1=CC=C(C)C(C)=C1 WBPIVENMALKVML-UHFFFAOYSA-N 0.000 claims description 2
- NKENMSBWRXCITN-UHFFFAOYSA-N 1-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-3-phenylurea Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)NC=2C=CC=CC=2)CC1C1=CC=C(C)C(C)=C1 NKENMSBWRXCITN-UHFFFAOYSA-N 0.000 claims description 2
- OAORVVWYOUFULR-UHFFFAOYSA-N 1-[[4-(dimethylamino)phenyl]methylamino]-4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=CC(=CC=2)N(C)C)CC1C1=CC=C(C)C(C)=C1 OAORVVWYOUFULR-UHFFFAOYSA-N 0.000 claims description 2
- IFQUNTMBZBSJBY-UHFFFAOYSA-N 1-[[4-(dimethylamino)phenyl]methylamino]-4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=CC(=CC=2)N(C)C)CC1C1=CC=C(OC)C=C1 IFQUNTMBZBSJBY-UHFFFAOYSA-N 0.000 claims description 2
- GVLDADZAAYTLGP-UHFFFAOYSA-N 1-amino-3-[2-(4-methoxyphenyl)ethyl]-4-(1-phenylcyclopropyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1(C=2C=CC=CC=2)CC1 GVLDADZAAYTLGP-UHFFFAOYSA-N 0.000 claims description 2
- ILHNQVMJCMOFTG-UHFFFAOYSA-N 1-amino-3-[2-(4-methoxyphenyl)ethyl]-4-(4-propan-2-yloxyphenyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1=CC=C(OC(C)C)C=C1 ILHNQVMJCMOFTG-UHFFFAOYSA-N 0.000 claims description 2
- OPJCUCQFYFNIDA-UHFFFAOYSA-N 1-amino-3-[2-(4-methoxyphenyl)ethyl]-4-[4-(trifluoromethoxy)phenyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1=CC=C(OC(F)(F)F)C=C1 OPJCUCQFYFNIDA-UHFFFAOYSA-N 0.000 claims description 2
- IEUGEDJHBDKDLS-UHFFFAOYSA-N 1-amino-3-[2-[4-(difluoromethoxy)phenyl]ethyl]-4-(4-methoxyphenyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1C1N(CCC=2C=CC(OC(F)F)=CC=2)C(=O)N(N)C1 IEUGEDJHBDKDLS-UHFFFAOYSA-N 0.000 claims description 2
- STUALXBCJWYUKO-UHFFFAOYSA-N 1-amino-4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1=CC=C(C)C(C)=C1 STUALXBCJWYUKO-UHFFFAOYSA-N 0.000 claims description 2
- HQRPFAWUHXSEDV-UHFFFAOYSA-N 1-amino-4-(4-tert-butylphenyl)-3-[3-(4-methoxyphenyl)propyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCCN1C(=O)N(N)CC1C1=CC=C(C(C)(C)C)C=C1 HQRPFAWUHXSEDV-UHFFFAOYSA-N 0.000 claims description 2
- HFQMYYDXXRDZBP-UHFFFAOYSA-N 1-amino-4-[(4-fluorophenyl)methyl]-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1CC1=CC=C(F)C=C1 HFQMYYDXXRDZBP-UHFFFAOYSA-N 0.000 claims description 2
- JACSGDUPYYCVFL-UHFFFAOYSA-N 1-amino-4-[1-(4-fluorophenyl)cyclopropyl]-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1(C=2C=CC(F)=CC=2)CC1 JACSGDUPYYCVFL-UHFFFAOYSA-N 0.000 claims description 2
- MSBCNYWTZYHXOT-UHFFFAOYSA-N 1-amino-4-[4-(2-methoxyethoxy)phenyl]-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OCCOC)=CC=C1C1N(CCC=2C=CC(OC)=CC=2)C(=O)N(N)C1 MSBCNYWTZYHXOT-UHFFFAOYSA-N 0.000 claims description 2
- MMDIVVYLPINAPP-UHFFFAOYSA-N 1-amino-4-[4-(difluoromethoxy)phenyl]-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N)CC1C1=CC=C(OC(F)F)C=C1 MMDIVVYLPINAPP-UHFFFAOYSA-N 0.000 claims description 2
- FAPNSGCVSUELJK-HXUWFJFHSA-N 1-cyano-n-[(4s)-4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC#N)C[C@@H]1C1=CC=C(OC)C=C1 FAPNSGCVSUELJK-HXUWFJFHSA-N 0.000 claims description 2
- JLUKQWCKOKZTJB-UHFFFAOYSA-N 1-cyano-n-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC#N)CC1C1=CC=C(OCCO2)C2=C1 JLUKQWCKOKZTJB-UHFFFAOYSA-N 0.000 claims description 2
- FAPNSGCVSUELJK-UHFFFAOYSA-N 1-cyano-n-[4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC#N)CC1C1=CC=C(OC)C=C1 FAPNSGCVSUELJK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
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- DDUHZVANACGSEG-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(C(C)(C)C)C=C1 DDUHZVANACGSEG-UHFFFAOYSA-N 0.000 claims description 2
- FZKGLMNVPPCQSM-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]pyrazine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)C=2N=CC=NC=2)CC1C1=CC=C(C(C)(C)C)C=C1 FZKGLMNVPPCQSM-UHFFFAOYSA-N 0.000 claims description 2
- WBNCPBUNFOXIIH-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-[4-(2-morpholin-4-ylethoxy)phenyl]ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C1N(CCC=2C=CC(OCCN3CCOCC3)=CC=2)C(=O)N(NS(C)(=O)=O)C1 WBNCPBUNFOXIIH-UHFFFAOYSA-N 0.000 claims description 2
- SUZVSGTZPBRARS-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-[4-[2-(dimethylamino)ethoxy]phenyl]ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OCCN(C)C)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(C(C)(C)C)C=C1 SUZVSGTZPBRARS-UHFFFAOYSA-N 0.000 claims description 2
- JJCVXVAYQMILLR-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[3-(4-methoxyphenyl)propyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(C(C)(C)C)C=C1 JJCVXVAYQMILLR-UHFFFAOYSA-N 0.000 claims description 2
- GHIXCIGHQPBXNA-UHFFFAOYSA-N n-[4-[(4-fluorophenyl)methyl]-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1CC1=CC=C(F)C=C1 GHIXCIGHQPBXNA-UHFFFAOYSA-N 0.000 claims description 2
- LEILGMDPXPXJMB-UHFFFAOYSA-N n-[4-[(4-tert-butylphenyl)methyl]-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(C)=O)CC1CC1=CC=C(C(C)(C)C)C=C1 LEILGMDPXPXJMB-UHFFFAOYSA-N 0.000 claims description 2
- MJGBTYCAVOAQPF-UHFFFAOYSA-N n-[4-[(4-tert-butylphenyl)methyl]-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1CC1=CC=C(C(C)(C)C)C=C1 MJGBTYCAVOAQPF-UHFFFAOYSA-N 0.000 claims description 2
- KFUKFGHAXYYRKV-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)cyclopropyl]-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1(C=2C=CC(F)=CC=2)CC1 KFUKFGHAXYYRKV-UHFFFAOYSA-N 0.000 claims description 2
- KASKTMSKBZKXPD-UHFFFAOYSA-N n-[4-[4-(2-methoxyethoxy)phenyl]-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OCCOC)=CC=C1C1N(CCC=2C=CC(OC)=CC=2)C(=O)N(NS(C)(=O)=O)C1 KASKTMSKBZKXPD-UHFFFAOYSA-N 0.000 claims description 2
- OLAWFFRRAXHKFG-UHFFFAOYSA-N n-[4-[4-(difluoromethoxy)phenyl]-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(OC(F)F)C=C1 OLAWFFRRAXHKFG-UHFFFAOYSA-N 0.000 claims description 2
- AKJQUJLTTIHHEB-UHFFFAOYSA-N n-[4-butyl-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1-pyridin-3-ylmethanesulfonamide Chemical compound O=C1N(CCC=2C=CC(OC)=CC=2)C(CCCC)CN1NS(=O)(=O)CC1=CC=CN=C1 AKJQUJLTTIHHEB-UHFFFAOYSA-N 0.000 claims description 2
- GZWOCJBSXZWLLM-UHFFFAOYSA-N n-[4-butyl-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound CCCCC1CN(NS(C)(=O)=O)C(=O)N1CCC1=CC=C(OC)C=C1 GZWOCJBSXZWLLM-UHFFFAOYSA-N 0.000 claims description 2
- ANSWNZAQEONBIR-UHFFFAOYSA-N n-[4-cyclohexyl-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1CCCCC1 ANSWNZAQEONBIR-UHFFFAOYSA-N 0.000 claims description 2
- AYKVFVSGMWBXDX-UHFFFAOYSA-N n-cyclobutyl-2-[[4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]sulfamoyl]acetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(=O)NC2CCC2)CC1C1=CC=C(OC)C=C1 AYKVFVSGMWBXDX-UHFFFAOYSA-N 0.000 claims description 2
- MVWDKRIVVXAQTD-UHFFFAOYSA-N n-cyclopropyl-2-[[4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]sulfamoyl]acetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(=O)NC2CC2)CC1C1=CC=C(OC)C=C1 MVWDKRIVVXAQTD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- WXWSKCAFIURTPZ-UHFFFAOYSA-N tert-butyl n-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]carbamate Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)OC(C)(C)C)CC1C1=CC=C(C)C(C)=C1 WXWSKCAFIURTPZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000006606 n-butoxy group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 0 Cc1c(C)c(*)c(*)cc1 Chemical compound Cc1c(C)c(*)c(*)cc1 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- LNBVVVZCIZAMGA-UHFFFAOYSA-N CNCCN(C(CN1NC)I)C1=[ClH] Chemical compound CNCCN(C(CN1NC)I)C1=[ClH] LNBVVVZCIZAMGA-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- DHIVBEZCBBHIPZ-UHFFFAOYSA-N 1-aminoimidazolidin-2-one Chemical class NN1CCNC1=O DHIVBEZCBBHIPZ-UHFFFAOYSA-N 0.000 description 1
- 108010042111 Kv1.5 Potassium Channel Proteins 0.000 description 1
- 102000004425 Kv1.5 Potassium Channel Human genes 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YPEOXOKWIWMQAT-XMMPIXPASA-N n-[(4s)-4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1-pyridin-3-ylmethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC=2C=NC=CC=2)C[C@@H]1C1=CC=C(OC)C=C1 YPEOXOKWIWMQAT-XMMPIXPASA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81509106P | 2006-06-20 | 2006-06-20 | |
| PCT/US2007/071587 WO2007149874A1 (en) | 2006-06-20 | 2007-06-19 | Imidazolidinone kv1.5 potassium channel inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009541343A JP2009541343A (ja) | 2009-11-26 |
| JP2009541343A5 true JP2009541343A5 (enExample) | 2010-07-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009516686A Withdrawn JP2009541343A (ja) | 2006-06-20 | 2007-06-19 | イミダゾリジノンＫｖ１．５カリウムチャネル阻害剤 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US7504517B2 (enExample) |
| EP (1) | EP2035392A1 (enExample) |
| JP (1) | JP2009541343A (enExample) |
| KR (1) | KR20090021223A (enExample) |
| CN (1) | CN101573341A (enExample) |
| AR (1) | AR061523A1 (enExample) |
| AU (1) | AU2007260985A1 (enExample) |
| BR (1) | BRPI0713320A2 (enExample) |
| CA (1) | CA2655574A1 (enExample) |
| CL (1) | CL2007001794A1 (enExample) |
| CO (1) | CO6150173A2 (enExample) |
| CR (1) | CR10527A (enExample) |
| EC (1) | ECSP088994A (enExample) |
| MX (1) | MX2008016399A (enExample) |
| NO (1) | NO20085252L (enExample) |
| PE (1) | PE20080942A1 (enExample) |
| RU (1) | RU2008150465A (enExample) |
| TW (1) | TW200815363A (enExample) |
| WO (1) | WO2007149874A1 (enExample) |
| ZA (1) | ZA200810763B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2007260985A1 (en) * | 2006-06-20 | 2007-12-27 | Wyeth | Imidazolidinone Kv1.5 potassium channel inhibitors |
| RU2373934C1 (ru) * | 2008-03-19 | 2009-11-27 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Применение производных глутаровой кислоты или их фармацевтически приемлемых солей в качестве противоаритмических средств |
| CN101544580B (zh) * | 2009-04-28 | 2019-03-15 | 大连凯飞精细化工有限公司 | R-alpha-氨基-4-甲氧基苯乙酰胺的合成方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4099009A (en) * | 1977-04-11 | 1978-07-04 | Morton-Norwick Products, Inc. | 1-(4-chlorophenyl)-3-(1-ureido)-2-imidazolidinone |
| SK94393A3 (en) | 1992-09-11 | 1994-08-10 | Thomae Gmbh Dr K | Cyclic derivatives of urea, process for their production and their pharmaceutical agents with the content of those |
| DE4332168A1 (de) | 1993-02-22 | 1995-03-23 | Thomae Gmbh Dr K | Cyclische Derivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| JP2000501111A (ja) | 1996-01-26 | 2000-02-02 | バーテックス ファーマシューティカルズ インコーポレイテッド | アスパルチルプロテアーゼインヒビター |
| CA2250192A1 (en) | 1996-04-03 | 1997-10-09 | Chrisopher J. Dinsmore | Inhibitors of farnesyl-protein transferase |
| US7129359B2 (en) | 2002-07-09 | 2006-10-31 | National Health Research Institutes | Imidazolidinone compounds |
| CN1582279A (zh) | 2001-11-30 | 2005-02-16 | 伊莱利利公司 | 过氧化物酶体激活的受体激动剂 |
| WO2003057214A1 (en) | 2001-12-28 | 2003-07-17 | Somatocor Pharmaceuticals, Inc. | Imidazolidin-2,4-dione derivatives as non-peptide somatostatin receptor ligands |
| WO2004046137A1 (en) | 2002-11-21 | 2004-06-03 | Vicore Pharma Ab | New tricyclic angiotensin ii agonists |
| JP2004262903A (ja) | 2003-03-04 | 2004-09-24 | Japan Science & Technology Agency | アジリジン類の製造方法 |
| US7259174B2 (en) | 2004-05-25 | 2007-08-21 | National Health Research Institutes | Imidazolidinone compounds |
| AR050858A1 (es) * | 2004-09-07 | 2006-11-29 | Glaxo Group Ltd | Compuesto de heteroaril-nitrilo sustituido, su uso para la fabricacion de un medicamento, composicion farmaceutica que lo comprende y procedimiento para la preparacion del mismo |
| KR100677149B1 (ko) | 2004-11-12 | 2007-02-02 | 삼성전자주식회사 | 잉크 조성물 |
| AU2007260985A1 (en) * | 2006-06-20 | 2007-12-27 | Wyeth | Imidazolidinone Kv1.5 potassium channel inhibitors |
-
2007
- 2007-06-19 AU AU2007260985A patent/AU2007260985A1/en not_active Abandoned
- 2007-06-19 CA CA002655574A patent/CA2655574A1/en not_active Abandoned
- 2007-06-19 KR KR1020097000926A patent/KR20090021223A/ko not_active Withdrawn
- 2007-06-19 WO PCT/US2007/071587 patent/WO2007149874A1/en not_active Ceased
- 2007-06-19 RU RU2008150465/04A patent/RU2008150465A/ru not_active Application Discontinuation
- 2007-06-19 PE PE2007000779A patent/PE20080942A1/es not_active Application Discontinuation
- 2007-06-19 US US11/765,359 patent/US7504517B2/en not_active Expired - Fee Related
- 2007-06-19 EP EP07798773A patent/EP2035392A1/en not_active Withdrawn
- 2007-06-19 AR ARP070102688A patent/AR061523A1/es unknown
- 2007-06-19 CL CL2007001794A patent/CL2007001794A1/es unknown
- 2007-06-19 CN CNA2007800285697A patent/CN101573341A/zh active Pending
- 2007-06-19 JP JP2009516686A patent/JP2009541343A/ja not_active Withdrawn
- 2007-06-19 MX MX2008016399A patent/MX2008016399A/es unknown
- 2007-06-19 BR BRPI0713320-0A patent/BRPI0713320A2/pt not_active IP Right Cessation
- 2007-06-20 TW TW096122064A patent/TW200815363A/zh unknown
-
2008
- 2008-11-06 US US12/266,212 patent/US7803827B2/en not_active Expired - Fee Related
- 2008-12-16 NO NO20085252A patent/NO20085252L/no not_active Application Discontinuation
- 2008-12-18 CR CR10527A patent/CR10527A/es not_active Application Discontinuation
- 2008-12-19 CO CO08135447A patent/CO6150173A2/es unknown
- 2008-12-19 EC EC2008008994A patent/ECSP088994A/es unknown
- 2008-12-19 ZA ZA200810763A patent/ZA200810763B/xx unknown
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