RU2008150465A - Ингибиторы калиевых каналов подтипа kv1.5 - Google Patents
Ингибиторы калиевых каналов подтипа kv1.5 Download PDFInfo
- Publication number
- RU2008150465A RU2008150465A RU2008150465/04A RU2008150465A RU2008150465A RU 2008150465 A RU2008150465 A RU 2008150465A RU 2008150465/04 A RU2008150465/04 A RU 2008150465/04A RU 2008150465 A RU2008150465 A RU 2008150465A RU 2008150465 A RU2008150465 A RU 2008150465A
- Authority
- RU
- Russia
- Prior art keywords
- methoxyphenyl
- ethyl
- imidazolidinone
- phenyl
- amino
- Prior art date
Links
- 102000004257 Potassium Channel Human genes 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 108020001213 potassium channel Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 91
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 31
- 239000001257 hydrogen Substances 0.000 claims abstract 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 29
- 125000004429 atom Chemical group 0.000 claims abstract 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 8
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- -1 4- (fluoromethyl) phenyl Chemical group 0.000 claims 74
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 24
- 150000003839 salts Chemical group 0.000 claims 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical group 0.000 claims 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 5
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 4
- 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 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 4
- 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 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 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 3
- 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 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- UTRBJWHDODTHJA-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[[3-[2-(4-cyclopropylphenyl)ethyl]-4-(4-methoxyphenyl)-2-oxoimidazolidin-1-yl]sulfamoyl]acetamide Chemical compound C1=CC(OC)=CC=C1C1N(CCC=2C=CC(=CC=2)C2CC2)C(=O)N(NS(=O)(=O)CC(=O)NCC2CC2)C1 UTRBJWHDODTHJA-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- FUHFFCFPCANDEX-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-1-[(4-imidazol-1-ylphenyl)methylamino]-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=CC(=CC=2)N2C=NC=C2)CC1C1=CC=C(C)C(C)=C1 FUHFFCFPCANDEX-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims 2
- 208000005189 Embolism Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000001435 Thromboembolism Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 2
- KSHHAJFXDPWBOJ-UHFFFAOYSA-N 1-(4-cyclopropylphenyl)imidazolidin-2-one Chemical compound O=C1NCCN1C1=CC=C(C2CC2)C=C1 KSHHAJFXDPWBOJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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- WPEJBVNSPGUJNH-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl 2-[[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]sulfamoyl]acetate Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(=O)OCC2C3=CC=CC=C3C3=CC=CC=C32)CC1C1=CC=C(C2CC2)C=C1 WPEJBVNSPGUJNH-UHFFFAOYSA-N 0.000 claims 1
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- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
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- 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 claims 1
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- OLAWFFRRAXHKFG-GOSISDBHSA-N n-[(4s)-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)C[C@@H]1C1=CC=C(OC(F)F)C=C1 OLAWFFRRAXHKFG-GOSISDBHSA-N 0.000 claims 1
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- PQGSNDQPFAIROH-UHFFFAOYSA-N n-[3-[2-(4-methoxyphenyl)ethyl]-2-oxo-4-(4-propan-2-yloxyphenyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(OC(C)C)C=C1 PQGSNDQPFAIROH-UHFFFAOYSA-N 0.000 claims 1
- OVMWGVIEIXVZDT-UHFFFAOYSA-N n-[3-[2-(4-methoxyphenyl)ethyl]-2-oxo-4-[4-(trifluoromethoxy)phenyl]imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(OC(F)(F)F)C=C1 OVMWGVIEIXVZDT-UHFFFAOYSA-N 0.000 claims 1
- DWJWXWBJERBHCG-UHFFFAOYSA-N n-[3-[2-(4-methoxyphenyl)ethyl]-2-oxo-4-[4-(trifluoromethyl)phenyl]imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(C(F)(F)F)C=C1 DWJWXWBJERBHCG-UHFFFAOYSA-N 0.000 claims 1
- CFTNVBRVUMZWLO-UHFFFAOYSA-N n-[3-[2-(4-methoxyphenyl)ethyl]-4-(4-methylphenyl)-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(C)C=C1 CFTNVBRVUMZWLO-UHFFFAOYSA-N 0.000 claims 1
- ZBRCBFCBZWYHTJ-UHFFFAOYSA-N n-[3-[2-(4-methoxyphenyl)ethyl]-4-(6-methoxypyridin-3-yl)-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(OC)N=C1 ZBRCBFCBZWYHTJ-UHFFFAOYSA-N 0.000 claims 1
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- LLZBODSIRMZMFN-UHFFFAOYSA-N n-[4-(2,2-difluoro-1,3-benzodioxol-5-yl)-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)O2)C2=C1 LLZBODSIRMZMFN-UHFFFAOYSA-N 0.000 claims 1
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- CBCHQQGUVGLNIQ-UHFFFAOYSA-N n-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]benzamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)C=2C=CC=CC=2)CC1C1=CC=C(C)C(C)=C1 CBCHQQGUVGLNIQ-UHFFFAOYSA-N 0.000 claims 1
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- ZQCKMCSWXJOSKY-UHFFFAOYSA-N n-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]furan-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)C=2OC=CC=2)CC1C1=CC=C(C)C(C)=C1 ZQCKMCSWXJOSKY-UHFFFAOYSA-N 0.000 claims 1
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- IIACSZNDQOVHKQ-UHFFFAOYSA-N n-[4-(4-cyclopropylphenyl)-3-[(4-methoxyphenyl)methyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(C2CC2)C=C1 IIACSZNDQOVHKQ-UHFFFAOYSA-N 0.000 claims 1
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- DGHURJYXAQLSSM-UHFFFAOYSA-N n-[4-(4-cyclopropylphenyl)-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(C2CC2)C=C1 DGHURJYXAQLSSM-UHFFFAOYSA-N 0.000 claims 1
- KYTLYLUWAQVBPX-UHFFFAOYSA-N n-[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]propane-1-sulfonamide Chemical compound O=C1N(NS(=O)(=O)CCC)CC(C=2C=CC(=CC=2)C2CC2)N1CCC1=CC=C(OC)C=C1 KYTLYLUWAQVBPX-UHFFFAOYSA-N 0.000 claims 1
- ANWLZNPLYZMQIB-UHFFFAOYSA-N n-[4-(4-cyclopropylphenyl)-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(C2CC2)C=C1 ANWLZNPLYZMQIB-UHFFFAOYSA-N 0.000 claims 1
- NWOQVXJNVGVKQU-UHFFFAOYSA-N n-[4-(4-fluorophenyl)-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)CC1C1=CC=C(F)C=C1 NWOQVXJNVGVKQU-UHFFFAOYSA-N 0.000 claims 1
- UMOACFKSMIUFHS-UHFFFAOYSA-N n-[4-(4-fluorophenyl)-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(F)C=C1 UMOACFKSMIUFHS-UHFFFAOYSA-N 0.000 claims 1
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- BUIOXJWBULUFSN-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-2-oxo-3-[2-[4-(trifluoromethoxy)phenyl]ethyl]imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1N(CCC=2C=CC(OC(F)(F)F)=CC=2)C(=O)N(NS(C)(=O)=O)C1 BUIOXJWBULUFSN-UHFFFAOYSA-N 0.000 claims 1
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- GFFIHDXPUGXVGG-UHFFFAOYSA-N n-[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)CC1C1=CC=C(OC)C=C1 GFFIHDXPUGXVGG-UHFFFAOYSA-N 0.000 claims 1
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- CZGKLRUJJXPRFH-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-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(OC)C=C1 CZGKLRUJJXPRFH-UHFFFAOYSA-N 0.000 claims 1
- XXEMFVIKJGFAEU-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C1N(CCCC=2C=CC=CC=2)C(=O)N(NS(C)(=O)=O)C1 XXEMFVIKJGFAEU-UHFFFAOYSA-N 0.000 claims 1
- MVYOPFBRKZWSLX-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)C(F)(F)F)CC1C1=CC=C(C(C)(C)C)C=C1 MVYOPFBRKZWSLX-UHFFFAOYSA-N 0.000 claims 1
- QYOJXVLGZCRGFK-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1,2-oxazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)C=2ON=CC=2)CC1C1=CC=C(C(C)(C)C)C=C1 QYOJXVLGZCRGFK-UHFFFAOYSA-N 0.000 claims 1
- WNICPUOTHIHEAR-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1-chloromethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CCl)CC1C1=CC=C(C(C)(C)C)C=C1 WNICPUOTHIHEAR-UHFFFAOYSA-N 0.000 claims 1
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- OYCGHRIITMJDOC-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-2,2,2-trifluoroethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(F)(F)F)CC1C1=CC=C(C(C)(C)C)C=C1 OYCGHRIITMJDOC-UHFFFAOYSA-N 0.000 claims 1
- LQILGVAKAWFWTQ-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-2-(2-phenylethylamino)acetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)CNCCC=2C=CC=CC=2)CC1C1=CC=C(C(C)(C)C)C=C1 LQILGVAKAWFWTQ-UHFFFAOYSA-N 0.000 claims 1
- VLGJUXAUFOJQQS-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]butane-1-sulfonamide Chemical compound O=C1N(NS(=O)(=O)CCCC)CC(C=2C=CC(=CC=2)C(C)(C)C)N1CCC1=CC=C(OC)C=C1 VLGJUXAUFOJQQS-UHFFFAOYSA-N 0.000 claims 1
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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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000006606 n-butoxy group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 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 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81509106P | 2006-06-20 | 2006-06-20 | |
| US60/815,091 | 2006-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008150465A true RU2008150465A (ru) | 2010-07-27 |
Family
ID=38582320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008150465/04A RU2008150465A (ru) | 2006-06-20 | 2007-06-19 | Ингибиторы калиевых каналов подтипа kv1.5 |
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 |
|---|---|---|---|---|
| CN101573341A (zh) * | 2006-06-20 | 2009-11-04 | 惠氏公司 | 咪唑烷酮Kv1.5钾通道抑制剂 |
| 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 |
| JP2000507581A (ja) | 1996-04-03 | 2000-06-20 | メルク エンド カンパニー インコーポレーテッド | ファルネシル―タンパク質転移酵素の阻害剤 |
| 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 |
| US7189856B2 (en) | 2001-12-28 | 2007-03-13 | Gideon Shapiro | Non-peptide somatostatin receptor ligands |
| AU2003302027A1 (en) | 2002-11-21 | 2004-06-15 | 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 |
| WO2006027211A1 (en) * | 2004-09-07 | 2006-03-16 | Glaxo Group Limited | 2,4-substituted pyrimidines as cysteine protease inhibitors |
| KR100677149B1 (ko) | 2004-11-12 | 2007-02-02 | 삼성전자주식회사 | 잉크 조성물 |
| CN101573341A (zh) * | 2006-06-20 | 2009-11-04 | 惠氏公司 | 咪唑烷酮Kv1.5钾通道抑制剂 |
-
2007
- 2007-06-19 CN CNA2007800285697A patent/CN101573341A/zh active Pending
- 2007-06-19 WO PCT/US2007/071587 patent/WO2007149874A1/en not_active Ceased
- 2007-06-19 CA CA002655574A patent/CA2655574A1/en not_active Abandoned
- 2007-06-19 MX MX2008016399A patent/MX2008016399A/es unknown
- 2007-06-19 CL CL2007001794A patent/CL2007001794A1/es unknown
- 2007-06-19 AR ARP070102688A patent/AR061523A1/es unknown
- 2007-06-19 EP EP07798773A patent/EP2035392A1/en not_active Withdrawn
- 2007-06-19 AU AU2007260985A patent/AU2007260985A1/en not_active Abandoned
- 2007-06-19 US US11/765,359 patent/US7504517B2/en not_active Expired - Fee Related
- 2007-06-19 PE PE2007000779A patent/PE20080942A1/es not_active Application Discontinuation
- 2007-06-19 RU RU2008150465/04A patent/RU2008150465A/ru not_active Application Discontinuation
- 2007-06-19 KR KR1020097000926A patent/KR20090021223A/ko not_active Withdrawn
- 2007-06-19 BR BRPI0713320-0A patent/BRPI0713320A2/pt not_active IP Right Cessation
- 2007-06-19 JP JP2009516686A patent/JP2009541343A/ja not_active Withdrawn
- 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 ZA ZA200810763A patent/ZA200810763B/xx unknown
- 2008-12-19 CO CO08135447A patent/CO6150173A2/es unknown
- 2008-12-19 EC EC2008008994A patent/ECSP088994A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7803827B2 (en) | 2010-09-28 |
| EP2035392A1 (en) | 2009-03-18 |
| US20070299120A1 (en) | 2007-12-27 |
| TW200815363A (en) | 2008-04-01 |
| WO2007149874A1 (en) | 2007-12-27 |
| US20090069342A1 (en) | 2009-03-12 |
| JP2009541343A (ja) | 2009-11-26 |
| CN101573341A (zh) | 2009-11-04 |
| ZA200810763B (en) | 2009-09-30 |
| PE20080942A1 (es) | 2008-09-03 |
| WO2007149874A8 (en) | 2008-03-20 |
| AU2007260985A1 (en) | 2007-12-27 |
| KR20090021223A (ko) | 2009-02-27 |
| CA2655574A1 (en) | 2007-12-27 |
| MX2008016399A (es) | 2009-02-03 |
| AR061523A1 (es) | 2008-09-03 |
| BRPI0713320A2 (pt) | 2012-02-07 |
| NO20085252L (no) | 2009-01-13 |
| CL2007001794A1 (es) | 2008-01-18 |
| US7504517B2 (en) | 2009-03-17 |
| ECSP088994A (es) | 2009-01-30 |
| CR10527A (es) | 2009-02-19 |
| CO6150173A2 (es) | 2010-04-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20110301 |