JP2009541343A5 - - Google Patents
Download PDFInfo
- 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- Withdrawn
Links
- -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
- WQVHBDVXSWFOPB-LJQANCHMSA-N 1-fluoro-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)CF)C[C@@H]1C1=CC=C(OC)C=C1 WQVHBDVXSWFOPB-LJQANCHMSA-N 0.000 claims description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 2
- DEVUHEGDLPZEGN-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)-n-[4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-2-oxoethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(=O)N2CCN(CC2)C(C)=O)CC1C1=CC=C(OC)C=C1 DEVUHEGDLPZEGN-UHFFFAOYSA-N 0.000 claims description 2
- XTRYLRSTVJIDEO-UHFFFAOYSA-N 2-[[2-[[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]sulfamoyl]acetyl]-methylamino]-n,n-dimethylacetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(=O)N(C)CC(=O)N(C)C)CC1C1=CC=C(C2CC2)C=C1 XTRYLRSTVJIDEO-UHFFFAOYSA-N 0.000 claims description 2
- BWYBYOVPPVFWSY-UHFFFAOYSA-N 2-[[4-(4-cyclopropylphenyl)-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(C2CC2)C=C1 BWYBYOVPPVFWSY-UHFFFAOYSA-N 0.000 claims description 2
- VJTBDNNBUUSUGW-UHFFFAOYSA-N 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(N)=O)CC1C1=CC=C(C2CC2)C=C1 VJTBDNNBUUSUGW-UHFFFAOYSA-N 0.000 claims description 2
- ZUWGGCOTSSPGIJ-UHFFFAOYSA-N 2-[[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]sulfamoyl]acetic acid Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC(O)=O)CC1C1=CC=C(C2CC2)C=C1 ZUWGGCOTSSPGIJ-UHFFFAOYSA-N 0.000 claims description 2
- HCYGSHSMBLUDMU-UHFFFAOYSA-N 2-[[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)propyl]-2-oxoimidazolidin-1-yl]sulfamoyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C)CN1C(=O)N(NS(=O)(=O)CC(N)=O)CC1C1=CC=C(C2CC2)C=C1 HCYGSHSMBLUDMU-UHFFFAOYSA-N 0.000 claims description 2
- NQIGJHKMUROMBM-UHFFFAOYSA-N 2-[[4-(4-cyclopropylphenyl)-3-[3-(4-methoxyphenyl)propyl]-2-oxoimidazolidin-1-yl]sulfamoyl]acetamide Chemical compound C1=CC(OC)=CC=C1CCCN1C(=O)N(NS(=O)(=O)CC(N)=O)CC1C1=CC=C(C2CC2)C=C1 NQIGJHKMUROMBM-UHFFFAOYSA-N 0.000 claims description 2
- CEFZLQACPIDOFW-UHFFFAOYSA-N 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(N)=O)CC1C1=CC=C(OC)C=C1 CEFZLQACPIDOFW-UHFFFAOYSA-N 0.000 claims description 2
- MKZPEDVURCIRNG-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-1-[(4-fluorophenyl)methylamino]-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=CC(F)=CC=2)CC1C1=CC=C(C)C(C)=C1 MKZPEDVURCIRNG-UHFFFAOYSA-N 0.000 claims description 2
- MTVWRWZYVQIWFE-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-(2-phenylethylamino)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCCC=2C=CC=CC=2)CC1C1=CC=C(C)C(C)=C1 MTVWRWZYVQIWFE-UHFFFAOYSA-N 0.000 claims description 2
- OWUDYQPICKCONV-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-(pyridin-2-ylmethylamino)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2N=CC=CC=2)CC1C1=CC=C(C)C(C)=C1 OWUDYQPICKCONV-UHFFFAOYSA-N 0.000 claims description 2
- YZZWZMCSWMZMPQ-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-(pyridin-3-ylmethylamino)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=NC=CC=2)CC1C1=CC=C(C)C(C)=C1 YZZWZMCSWMZMPQ-UHFFFAOYSA-N 0.000 claims description 2
- RMWJWFRNRUWNHG-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-(quinolin-2-ylmethylamino)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2N=C3C=CC=CC3=CC=2)CC1C1=CC=C(C)C(C)=C1 RMWJWFRNRUWNHG-UHFFFAOYSA-N 0.000 claims description 2
- UACKQAVSAVADKM-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-(quinolin-3-ylmethylamino)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=C3C=CC=CC3=NC=2)CC1C1=CC=C(C)C(C)=C1 UACKQAVSAVADKM-UHFFFAOYSA-N 0.000 claims description 2
- XYICBMXHOLJECE-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-[(1-methylimidazol-2-yl)methylamino]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2N(C=CN=2)C)CC1C1=CC=C(C)C(C)=C1 XYICBMXHOLJECE-UHFFFAOYSA-N 0.000 claims description 2
- YECSKPGYYHAIKJ-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxo-1-(sulfamoylamino)imidazolidine Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(N)(=O)=O)CC1C1=CC=C(C)C(C)=C1 YECSKPGYYHAIKJ-UHFFFAOYSA-N 0.000 claims description 2
- YMSLDWJWQCHNHH-UHFFFAOYSA-N 4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxo-1-(sulfamoylamino)imidazolidine Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(N)(=O)=O)CC1C1=CC=C(C2CC2)C=C1 YMSLDWJWQCHNHH-UHFFFAOYSA-N 0.000 claims description 2
- MTYOPNIZSSGUKG-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxo-1-(sulfamoylamino)imidazolidine Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(N)(=O)=O)CC1C1=CC=C(OC)C=C1 MTYOPNIZSSGUKG-UHFFFAOYSA-N 0.000 claims description 2
- RHLCVEDBSQZKAX-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-1-(2-imidazol-1-ylethylamino)-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCCN2C=NC=C2)CC1C1=CC=C(C(C)(C)C)C=C1 RHLCVEDBSQZKAX-UHFFFAOYSA-N 0.000 claims description 2
- FXFQONKAJWILTE-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-1-[[4-(diethylamino)phenyl]methylamino]-3-[2-(4-methoxyphenyl)ethyl]imidazolidin-2-one Chemical compound C1=CC(N(CC)CC)=CC=C1CNN1C(=O)N(CCC=2C=CC(OC)=CC=2)C(C=2C=CC(=CC=2)C(C)(C)C)C1 FXFQONKAJWILTE-UHFFFAOYSA-N 0.000 claims description 2
- PIALCFFDDRCNRG-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-1-[[4-(dimethylamino)phenyl]methylamino]-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)C)C=C1 PIALCFFDDRCNRG-UHFFFAOYSA-N 0.000 claims description 2
- XYUXAIGGNWJFKO-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-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)C)C=C1 XYUXAIGGNWJFKO-UHFFFAOYSA-N 0.000 claims description 2
- LFGRRDPPIUQCDI-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-piperazin-1-ylimidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N2CCNCC2)CC1C1=CC=C(C(C)(C)C)C=C1 LFGRRDPPIUQCDI-UHFFFAOYSA-N 0.000 claims description 2
- ZPOIAGCJALONAW-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxo-1-(sulfamoylamino)imidazolidine Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(N)(=O)=O)CC1C1=CC=C(C(C)(C)C)C=C1 ZPOIAGCJALONAW-UHFFFAOYSA-N 0.000 claims description 2
- SAQPLRDGGFJOSZ-UHFFFAOYSA-N 4-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N2CCN(CC2)C(=O)N(C)C)CC1C1=CC=C(C(C)(C)C)C=C1 SAQPLRDGGFJOSZ-UHFFFAOYSA-N 0.000 claims description 2
- WKJLPZTYEHEGAG-UHFFFAOYSA-N 4-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-n-methylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)NC)CCN1N1C(=O)N(CCC=2C=CC(OC)=CC=2)C(C=2C=CC(=CC=2)C(C)(C)C)C1 WKJLPZTYEHEGAG-UHFFFAOYSA-N 0.000 claims description 2
- KFDLKCDZCWHYTL-UHFFFAOYSA-N 4-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]piperazine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(N2CCN(CC2)C(N)=O)CC1C1=CC=C(C(C)(C)C)C=C1 KFDLKCDZCWHYTL-UHFFFAOYSA-N 0.000 claims description 2
- NDTMYIVDMTUEOY-UHFFFAOYSA-N 4-[[[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]amino]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NCC=2C=CC(=CC=2)C#N)CC1C1=CC=C(C)C(C)=C1 NDTMYIVDMTUEOY-UHFFFAOYSA-N 0.000 claims description 2
- QKEBMZOYCXSKFB-UHFFFAOYSA-N 4-amino-4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-1-(methylsulfonylmethylsulfonyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1CCN1C(C=2C=CC(=CC=2)C2CC2)(N)CN(S(=O)(=O)CS(C)(=O)=O)C1=O QKEBMZOYCXSKFB-UHFFFAOYSA-N 0.000 claims description 2
- PRMJZUUFVZZIEV-UHFFFAOYSA-N 4-amino-4-(4-methoxyphenyl)-3-(3-phenylpropyl)-1-(pyridin-3-ylmethylsulfonyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1C1(N)N(CCCC=2C=CC=CC=2)C(=O)N(S(=O)(=O)CC=2C=NC=CC=2)C1 PRMJZUUFVZZIEV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 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 description 2
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims description 2
- PZATUQOYIKEVBH-UHFFFAOYSA-N N1=CC(=CC=C1)CS(=O)(=O)N1C(N(C(C1)(C1=CC=C(C=C1)C)N)CCC1=CC=C(C=C1)OC)=O Chemical compound N1=CC(=CC=C1)CS(=O)(=O)N1C(N(C(C1)(C1=CC=C(C=C1)C)N)CCC1=CC=C(C=C1)OC)=O PZATUQOYIKEVBH-UHFFFAOYSA-N 0.000 claims description 2
- BHTGJDXKRFABOK-UHFFFAOYSA-N [4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]urea Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(N)=O)CC1C1=CC=C(C)C(C)=C1 BHTGJDXKRFABOK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- RIAJTSBVPJNAFA-UHFFFAOYSA-N methyl 3-amino-4-[[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]amino]benzoate Chemical compound NC1=CC(C(=O)OC)=CC=C1NN1C(=O)N(CCC=2C=CC(OC)=CC=2)C(C=2C=C(C)C(C)=CC=2)C1 RIAJTSBVPJNAFA-UHFFFAOYSA-N 0.000 claims description 2
- TYDUQWLCXINANF-UHFFFAOYSA-N methyl n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]carbamate Chemical compound O=C1N(NC(=O)OC)CC(C=2C=CC(=CC=2)C(C)(C)C)N1CCC1=CC=C(OC)C=C1 TYDUQWLCXINANF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- SRQBATMEOHWMJX-HSZRJFAPSA-N n-(cyclopropylmethyl)-2-[[(4s)-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)NCC2CC2)C[C@@H]1C1=CC=C(OC)C=C1 SRQBATMEOHWMJX-HSZRJFAPSA-N 0.000 claims description 2
- ZCCYIALZQNXOKB-FQEVSTJZSA-N n-[(4r)-4-(3,4-dimethylphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=C(C)C(C)=CC=C1[C@H]1N(CCCC=2C=CC=CC=2)C(=O)N(NS(C)(=O)=O)C1 ZCCYIALZQNXOKB-FQEVSTJZSA-N 0.000 claims description 2
- JFTNAHZEOMLTPQ-FQEVSTJZSA-N n-[(4r)-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)C[C@H]1C1=CC=C(C)C(C)=C1 JFTNAHZEOMLTPQ-FQEVSTJZSA-N 0.000 claims description 2
- WNRVVISRZUGQBG-NRFANRHFSA-N n-[(4r)-4-(4-cyclopropylphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound N1([C@@H](CN(C1=O)NS(=O)(=O)C)C=1C=CC(=CC=1)C1CC1)CCCC1=CC=CC=C1 WNRVVISRZUGQBG-NRFANRHFSA-N 0.000 claims description 2
- DGHURJYXAQLSSM-NRFANRHFSA-N n-[(4r)-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)C[C@H]1C1=CC=C(C2CC2)C=C1 DGHURJYXAQLSSM-NRFANRHFSA-N 0.000 claims description 2
- YBIJKAGSMMVLKJ-IBGZPJMESA-N n-[(4r)-4-(4-methoxyphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1[C@H]1N(CCCC=2C=CC=CC=2)C(=O)N(NS(C)(=O)=O)C1 YBIJKAGSMMVLKJ-IBGZPJMESA-N 0.000 claims description 2
- XXEMFVIKJGFAEU-NRFANRHFSA-N n-[(4r)-4-(4-tert-butylphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1[C@H]1N(CCCC=2C=CC=CC=2)C(=O)N(NS(C)(=O)=O)C1 XXEMFVIKJGFAEU-NRFANRHFSA-N 0.000 claims description 2
- OLAWFFRRAXHKFG-SFHVURJKSA-N n-[(4r)-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-SFHVURJKSA-N 0.000 claims description 2
- ZCCYIALZQNXOKB-HXUWFJFHSA-N n-[(4s)-4-(3,4-dimethylphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=C(C)C(C)=CC=C1[C@@H]1N(CCCC=2C=CC=CC=2)C(=O)N(NS(C)(=O)=O)C1 ZCCYIALZQNXOKB-HXUWFJFHSA-N 0.000 claims description 2
- JFTNAHZEOMLTPQ-HXUWFJFHSA-N n-[(4s)-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)C[C@@H]1C1=CC=C(C)C(C)=C1 JFTNAHZEOMLTPQ-HXUWFJFHSA-N 0.000 claims description 2
- WNRVVISRZUGQBG-OAQYLSRUSA-N n-[(4s)-4-(4-cyclopropylphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound N1([C@H](CN(C1=O)NS(=O)(=O)C)C=1C=CC(=CC=1)C1CC1)CCCC1=CC=CC=C1 WNRVVISRZUGQBG-OAQYLSRUSA-N 0.000 claims description 2
- DGHURJYXAQLSSM-OAQYLSRUSA-N n-[(4s)-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)C[C@@H]1C1=CC=C(C2CC2)C=C1 DGHURJYXAQLSSM-OAQYLSRUSA-N 0.000 claims description 2
- YBIJKAGSMMVLKJ-LJQANCHMSA-N n-[(4s)-4-(4-methoxyphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1[C@@H]1N(CCCC=2C=CC=CC=2)C(=O)N(NS(C)(=O)=O)C1 YBIJKAGSMMVLKJ-LJQANCHMSA-N 0.000 claims description 2
- XXEMFVIKJGFAEU-OAQYLSRUSA-N n-[(4s)-4-(4-tert-butylphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1[C@@H]1N(CCCC=2C=CC=CC=2)C(=O)N(NS(C)(=O)=O)C1 XXEMFVIKJGFAEU-OAQYLSRUSA-N 0.000 claims description 2
- 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 description 2
- DOXOKPQJRJQUKI-UHFFFAOYSA-N n-[3-[2-(4-ethoxyphenyl)ethyl]-4-(4-methoxyphenyl)-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OCC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(OC)C=C1 DOXOKPQJRJQUKI-UHFFFAOYSA-N 0.000 claims description 2
- NCIZOGCUYLERBF-UHFFFAOYSA-N n-[3-[2-(4-methoxyphenyl)ethyl]-2-oxo-4-(1-phenylcyclopropyl)imidazolidin-1-yl]-1-pyridin-3-ylmethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CC=2C=NC=CC=2)CC1C1(C=2C=CC=CC=2)CC1 NCIZOGCUYLERBF-UHFFFAOYSA-N 0.000 claims description 2
- UIBVVXRPUGSIGY-UHFFFAOYSA-N n-[3-[2-(4-methoxyphenyl)ethyl]-2-oxo-4-(1-phenylcyclopropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1(C=2C=CC=CC=2)CC1 UIBVVXRPUGSIGY-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- DQXOFPPIGSMKNT-UHFFFAOYSA-N n-[3-[2-(4-methoxyphenyl)ethyl]-2-oxo-4-quinolin-6-ylimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(N=CC=C2)C2=C1 DQXOFPPIGSMKNT-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- WPSHFQFGFQBCBX-UHFFFAOYSA-N n-[3-[2-[4-(difluoromethoxy)phenyl]ethyl]-4-(4-methoxyphenyl)-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1N(CCC=2C=CC(OC(F)F)=CC=2)C(=O)N(NS(C)(=O)=O)C1 WPSHFQFGFQBCBX-UHFFFAOYSA-N 0.000 claims description 2
- WUZXKEXAYSHGHD-UHFFFAOYSA-N n-[4,4-diethyl-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1-pyridin-3-ylmethanesulfonamide Chemical compound O=C1N(CCC=2C=CC(OC)=CC=2)C(CC)(CC)CN1NS(=O)(=O)CC1=CC=CN=C1 WUZXKEXAYSHGHD-UHFFFAOYSA-N 0.000 claims description 2
- ARWCGONAPNLWOD-UHFFFAOYSA-N n-[4,4-diethyl-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound CCC1(CC)CN(NS(C)(=O)=O)C(=O)N1CCC1=CC=C(OC)C=C1 ARWCGONAPNLWOD-UHFFFAOYSA-N 0.000 claims description 2
- WJLVHZFNBUMIRH-UHFFFAOYSA-N n-[4-(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(OCO2)C2=C1 WJLVHZFNBUMIRH-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- JVWUYEMNXVFCFF-UHFFFAOYSA-N n-[4-(2,2-dimethyl-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(C)(C)O2)C2=C1 JVWUYEMNXVFCFF-UHFFFAOYSA-N 0.000 claims description 2
- LPYGUDCNLDUQJW-UHFFFAOYSA-N n-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[2-(3,4-dimethoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]methanesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1CCN1C(=O)N(NS(C)(=O)=O)CC1C1=CC=C(OCCO2)C2=C1 LPYGUDCNLDUQJW-UHFFFAOYSA-N 0.000 claims description 2
- NWFBNTWHCFLAMX-UHFFFAOYSA-N n-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1-fluoromethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CF)CC1C1=CC=C(OCCO2)C2=C1 NWFBNTWHCFLAMX-UHFFFAOYSA-N 0.000 claims description 2
- ADGCOCBAQNGJEN-UHFFFAOYSA-N n-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-2-morpholin-4-ylethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CCN2CCOCC2)CC1C1=CC=C(OCCO2)C2=C1 ADGCOCBAQNGJEN-UHFFFAOYSA-N 0.000 claims description 2
- UTBBBMJOCCLYDX-UHFFFAOYSA-N n-[4-(2-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=CC=C1C1CC1 UTBBBMJOCCLYDX-UHFFFAOYSA-N 0.000 claims description 2
- JYANULVSYOWENS-UHFFFAOYSA-N n-[4-(3,4-dimethoxyphenyl)-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(OC)=C1 JYANULVSYOWENS-UHFFFAOYSA-N 0.000 claims description 2
- IEGGMGUHFMWJCW-UHFFFAOYSA-N n-[4-(3,4-dimethylphenyl)-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)=C1 IEGGMGUHFMWJCW-UHFFFAOYSA-N 0.000 claims description 2
- ZCEIQKWSVWHJTK-UHFFFAOYSA-N n-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-2-phenoxyacetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)COC=2C=CC=CC=2)CC1C1=CC=C(C)C(C)=C1 ZCEIQKWSVWHJTK-UHFFFAOYSA-N 0.000 claims description 2
- JDVWXPLEMHRGBE-UHFFFAOYSA-N n-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-2-phenylacetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)CC=2C=CC=CC=2)CC1C1=CC=C(C)C(C)=C1 JDVWXPLEMHRGBE-UHFFFAOYSA-N 0.000 claims description 2
- VHCGXVCLLLRYNU-UHFFFAOYSA-N n-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-4-methylpiperazine-1-sulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)N2CCN(C)CC2)CC1C1=CC=C(C)C(C)=C1 VHCGXVCLLLRYNU-UHFFFAOYSA-N 0.000 claims description 2
- PLLUPEGCAGPRPC-UHFFFAOYSA-N n-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(C)=O)CC1C1=CC=C(C)C(C)=C1 PLLUPEGCAGPRPC-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- XZJWRUZYSXEDSH-UHFFFAOYSA-N n-[4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]cyclopropanecarboxamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)C2CC2)CC1C1=CC=C(C)C(C)=C1 XZJWRUZYSXEDSH-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- GENWAOXOZDZWRT-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-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(Cl)C=C1 GENWAOXOZDZWRT-UHFFFAOYSA-N 0.000 claims description 2
- WNRVVISRZUGQBG-UHFFFAOYSA-N n-[4-(4-cyclopropylphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound O=C1N(NS(=O)(=O)C)CC(C=2C=CC(=CC=2)C2CC2)N1CCCC1=CC=CC=C1 WNRVVISRZUGQBG-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- GZYKYCIRGOPGET-UHFFFAOYSA-N n-[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1-fluoromethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CF)CC1C1=CC=C(C2CC2)C=C1 GZYKYCIRGOPGET-UHFFFAOYSA-N 0.000 claims description 2
- XNAPAPWORLZTON-UHFFFAOYSA-N n-[4-(4-cyclopropylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-2-pyridin-3-ylacetamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)CC=2C=NC=CC=2)CC1C1=CC=C(C2CC2)C=C1 XNAPAPWORLZTON-UHFFFAOYSA-N 0.000 claims description 2
- KYPPIHNCUSVEFS-UHFFFAOYSA-N n-[4-(4-cyclopropylphenyl)-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)C2CC2)N1CCC1=CC=C(OC)C=C1 KYPPIHNCUSVEFS-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- YBIJKAGSMMVLKJ-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-2-oxo-3-(3-phenylpropyl)imidazolidin-1-yl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1N(CCCC=2C=CC=CC=2)C(=O)N(NS(C)(=O)=O)C1 YBIJKAGSMMVLKJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- DCRGVZCDPZOVHI-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]cyclopropanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)C2CC2)CC1C1=CC=C(OC)C=C1 DCRGVZCDPZOVHI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- YLMIVHHEXDPLOJ-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]pyridine-3-sulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)C=2C=NC=CC=2)CC1C1=CC=C(OC)C=C1 YLMIVHHEXDPLOJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- LIQOINHZWWLFPW-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]-1-fluoromethanesulfonamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NS(=O)(=O)CF)CC1C1=CC=C(C(C)(C)C)C=C1 LIQOINHZWWLFPW-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- NJHVVIDWYHAORN-UHFFFAOYSA-N n-[4-(4-tert-butylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxoimidazolidin-1-yl]cyclopropanecarboxamide Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)N(NC(=O)C2CC2)CC1C1=CC=C(C(C)(C)C)C=C1 NJHVVIDWYHAORN-UHFFFAOYSA-N 0.000 claims description 2
- 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 (https=) | 2010-07-15 |
Family
ID=38582320
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 (https=) |
| EP (1) | EP2035392A1 (https=) |
| JP (1) | JP2009541343A (https=) |
| KR (1) | KR20090021223A (https=) |
| CN (1) | CN101573341A (https=) |
| AR (1) | AR061523A1 (https=) |
| AU (1) | AU2007260985A1 (https=) |
| BR (1) | BRPI0713320A2 (https=) |
| CA (1) | CA2655574A1 (https=) |
| CL (1) | CL2007001794A1 (https=) |
| CO (1) | CO6150173A2 (https=) |
| CR (1) | CR10527A (https=) |
| EC (1) | ECSP088994A (https=) |
| MX (1) | MX2008016399A (https=) |
| NO (1) | NO20085252L (https=) |
| PE (1) | PE20080942A1 (https=) |
| RU (1) | RU2008150465A (https=) |
| TW (1) | TW200815363A (https=) |
| WO (1) | WO2007149874A1 (https=) |
| ZA (1) | ZA200810763B (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2008150465A (ru) * | 2006-06-20 | 2010-07-27 | Вайет (Us) | Ингибиторы калиевых каналов подтипа kv1.5 |
| 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 |
| HUP9901024A2 (hu) | 1996-01-26 | 1999-09-28 | Vertex Pharmaceuticals Incorporated | Telített azolok oxoszármazékai, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk |
| EP0891353A4 (en) | 1996-04-03 | 2001-08-08 | Merck & Co Inc | FARNESYL PROTEIN TRANSFERASE INHIBITORS |
| US7129359B2 (en) | 2002-07-09 | 2006-10-31 | National Health Research Institutes | Imidazolidinone compounds |
| US7544812B2 (en) | 2001-11-30 | 2009-06-09 | Eli Lilly And Company | Peroxisome proliferator activated receptor agonists |
| 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 |
| TW200624429A (en) | 2004-09-07 | 2006-07-16 | Glaxo Group Ltd | Novel cysteine protease inhibitors |
| KR100677149B1 (ko) | 2004-11-12 | 2007-02-02 | 삼성전자주식회사 | 잉크 조성물 |
| RU2008150465A (ru) * | 2006-06-20 | 2010-07-27 | Вайет (Us) | Ингибиторы калиевых каналов подтипа kv1.5 |
-
2007
- 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 CN CNA2007800285697A patent/CN101573341A/zh active Pending
- 2007-06-19 JP JP2009516686A patent/JP2009541343A/ja not_active Withdrawn
- 2007-06-19 AU AU2007260985A patent/AU2007260985A1/en not_active Abandoned
- 2007-06-19 BR BRPI0713320-0A patent/BRPI0713320A2/pt not_active IP Right Cessation
- 2007-06-19 EP EP07798773A patent/EP2035392A1/en not_active Withdrawn
- 2007-06-19 CA CA002655574A patent/CA2655574A1/en not_active Abandoned
- 2007-06-19 US US11/765,359 patent/US7504517B2/en not_active Expired - Fee Related
- 2007-06-19 MX MX2008016399A patent/MX2008016399A/es unknown
- 2007-06-19 CL CL2007001794A patent/CL2007001794A1/es unknown
- 2007-06-19 WO PCT/US2007/071587 patent/WO2007149874A1/en not_active Ceased
- 2007-06-19 AR ARP070102688A patent/AR061523A1/es unknown
- 2007-06-19 PE PE2007000779A patent/PE20080942A1/es not_active Application Discontinuation
- 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 EC EC2008008994A patent/ECSP088994A/es unknown
- 2008-12-19 ZA ZA200810763A patent/ZA200810763B/xx unknown
- 2008-12-19 CO CO08135447A patent/CO6150173A2/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2361860C2 (ru) | Новые замещенные 3-сера-индолы | |
| CA2677313C (en) | Pyrimidinylaminobenzamide derivatives and their use as inhibitors of tyrosine kinases | |
| JP2013517283A5 (https=) | ||
| RU2455288C2 (ru) | Соединения и композиции 5-(4-(галогеналкокси)фенил)пиримидин-2-амина в качестве ингибиторов киназ | |
| RU2011149360A (ru) | Замещенные фенилмочевины и фениламиды в качестве лигандов ваниллоидных рецепторов | |
| JP2004507461A5 (https=) | ||
| RU2330019C2 (ru) | Производные пиперидина, способ их получения, фармацевтическая композиция на их основе и способ лечения хемокин-опосредованного болезненного состояния с их использованием | |
| JP2005510500A5 (https=) | ||
| KR101574906B1 (ko) | 치환된 벤즈아마이드 유도체 | |
| JP2011518774A5 (https=) | ||
| JP2019533694A5 (https=) | ||
| KR101461294B1 (ko) | Ｃｎｓ 장애 치료용 옥사졸린 유도체 | |
| JP2007519754A5 (https=) | ||
| EP0661266A1 (en) | Substituted cyclic amine compounds as 5HT2 antagonists | |
| JP3068208B2 (ja) | Ｐｄｅｉｖ阻害性の２―シアノイミノイミダゾール誘導体 | |
| JP2021512889A5 (https=) | ||
| RU2019117556A (ru) | Индазольные производные, пригодные в качестве ингибиторов диацилглицерид o-ацилтрансферазы 2 | |
| JP2009541343A5 (https=) | ||
| JP2004502674A5 (https=) | ||
| JP2009514866A5 (https=) | ||
| JP2020508300A5 (https=) | ||
| RU2017120277A (ru) | Новые соединения | |
| RU2008150465A (ru) | Ингибиторы калиевых каналов подтипа kv1.5 | |
| RU2007127864A (ru) | Производные n-[(4, 5-дифенил-3-алкил-2-тиенил)метил]амина (амид, сульфонамид, карбамат и карбамид) в качестве антагонистов рецепторов св1 каннабиноидов | |
| RU2006135486A (ru) | Производные n-пиперидина в качестве модуляторов ссr3 |