CA2528119A1 - Cis-2,4,5-triaryl-imidazolines - Google Patents
Cis-2,4,5-triaryl-imidazolines Download PDFInfo
- Publication number
- CA2528119A1 CA2528119A1 CA002528119A CA2528119A CA2528119A1 CA 2528119 A1 CA2528119 A1 CA 2528119A1 CA 002528119 A CA002528119 A CA 002528119A CA 2528119 A CA2528119 A CA 2528119A CA 2528119 A1 CA2528119 A1 CA 2528119A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- trifluoromethyl
- chloro
- bis
- dihydro
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 102000012199 E3 ubiquitin-protein ligase Mdm2 Human genes 0.000 claims abstract description 18
- 108050002772 E3 ubiquitin-protein ligase Mdm2 Proteins 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 13
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 9
- 230000003993 interaction Effects 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 441
- 125000003545 alkoxy group Chemical group 0.000 claims description 188
- 125000000623 heterocyclic group Chemical group 0.000 claims description 167
- 125000001424 substituent group Chemical group 0.000 claims description 128
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 123
- 125000004043 oxo group Chemical group O=* 0.000 claims description 99
- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 36
- -1 cyano, hydroxy Chemical group 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical group [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000000565 sulfonamide group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- PMKOHDFNHIQHEU-UHFFFAOYSA-N 1-[2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-oxoethyl]-n,n-diethylpiperidine-3-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN2CC(CCC2)C(=O)N(CC)CC)CC1 PMKOHDFNHIQHEU-UHFFFAOYSA-N 0.000 claims description 2
- ZNZKQJWQOKNGIO-UHFFFAOYSA-N 1-[2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]acetyl]-n,n-diethylpiperidine-3-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CC(CCC2)C(=O)N(CC)CC)CC1 ZNZKQJWQOKNGIO-UHFFFAOYSA-N 0.000 claims description 2
- IFZDTJNREFBQTR-UHFFFAOYSA-N 1-[2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-2-oxoethyl]-n,n-diethylpiperidine-3-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NC(=O)CN2CC(CCC2)C(=O)N(CC)CC)CC1 IFZDTJNREFBQTR-UHFFFAOYSA-N 0.000 claims description 2
- ZAWFJNDMMRRTMD-UHFFFAOYSA-N 1-[2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-2-oxoethyl]piperidine-3-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NC(=O)CN2CC(CCC2)C(N)=O)CC1 ZAWFJNDMMRRTMD-UHFFFAOYSA-N 0.000 claims description 2
- GJOIYISPAKKBDK-UHFFFAOYSA-N 1-[2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NC(=O)CN2CCC(CC2)C(N)=O)CC1 GJOIYISPAKKBDK-UHFFFAOYSA-N 0.000 claims description 2
- LGQBICOQRLJALZ-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-(dimethylamino)ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN(C)C)CC1 LGQBICOQRLJALZ-UHFFFAOYSA-N 0.000 claims description 2
- YXPRNTPQPZRLEF-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-[2-(dimethylamino)ethylamino]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CNCCN(C)C)CC1 YXPRNTPQPZRLEF-UHFFFAOYSA-N 0.000 claims description 2
- SXVYOQHGEIBTGB-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-[methyl-(1-methylpyrrolidin-3-yl)amino]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN(C)C2CN(C)CC2)CC1 SXVYOQHGEIBTGB-UHFFFAOYSA-N 0.000 claims description 2
- ZPMWMBBYMBLEOL-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-methoxyethanone;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)COC)CC1 ZPMWMBBYMBLEOL-UHFFFAOYSA-N 0.000 claims description 2
- GWXFDEKTMYHREF-UHFFFAOYSA-N 1-[4-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]sulfonylpiperazin-1-yl]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)N2CCN(CC2)C(C)=O)CC1 GWXFDEKTMYHREF-UHFFFAOYSA-N 0.000 claims description 2
- SIRRGYOWMNYEGB-UHFFFAOYSA-N 1-[4-[[4-[4,5-bis(4-chlorophenyl)-2-[2-propan-2-yloxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]phenyl]methyl]piperazin-1-yl]ethanone;hydrochloride Chemical compound Cl.CC(C)OC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C=C1)=CC=C1CN1CCN(C(C)=O)CC1 SIRRGYOWMNYEGB-UHFFFAOYSA-N 0.000 claims description 2
- YVUAWTINQHPMBG-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-1-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CCC3(CC2)OCCO3)CC1 YVUAWTINQHPMBG-UHFFFAOYSA-N 0.000 claims description 2
- LNJVNRIFSMVMBJ-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-1-[4-(2-hydroxyethyl)piperidin-1-yl]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CCC(CCO)CC2)CC1 LNJVNRIFSMVMBJ-UHFFFAOYSA-N 0.000 claims description 2
- XWSILZLDAKXQSK-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-1-[4-(hydroxymethyl)piperidin-1-yl]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CCC(CO)CC2)CC1 XWSILZLDAKXQSK-UHFFFAOYSA-N 0.000 claims description 2
- GUFQMXVXIWTNOX-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-1-[4-(trifluoromethyl)piperidin-1-yl]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CCC(CC2)C(F)(F)F)CC1 GUFQMXVXIWTNOX-UHFFFAOYSA-N 0.000 claims description 2
- IPONKTFQLKPTGG-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CCCC2)CC1 IPONKTFQLKPTGG-UHFFFAOYSA-N 0.000 claims description 2
- YGOXRDOHYBSCHA-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-1-thiomorpholin-4-ylethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CCSCC2)CC1 YGOXRDOHYBSCHA-UHFFFAOYSA-N 0.000 claims description 2
- MQMZUIHFOFNBJQ-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n,n-bis(2-methoxyethyl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(CCOC)CCOC)CC1 MQMZUIHFOFNBJQ-UHFFFAOYSA-N 0.000 claims description 2
- VWUWYTDXGJFOGO-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n,n-diethylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(CC)CC)CC1 VWUWYTDXGJFOGO-UHFFFAOYSA-N 0.000 claims description 2
- SRBBJOUGKVHQQN-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(1,3-dioxolan-2-ylmethyl)-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(C)CC2OCCO2)CC1 SRBBJOUGKVHQQN-UHFFFAOYSA-N 0.000 claims description 2
- RHOQXHDPMWCDRH-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(2-hydroxyethyl)-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(C)CCO)CC1 RHOQXHDPMWCDRH-UHFFFAOYSA-N 0.000 claims description 2
- OWYVHASFWKEOJJ-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(furan-2-ylmethyl)-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(C)CC=2OC=CC=2)CC1 OWYVHASFWKEOJJ-UHFFFAOYSA-N 0.000 claims description 2
- HNKROGOWIIXEAQ-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-[(5-methylfuran-2-yl)methyl]acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NCC=2OC(C)=CC=2)CC1 HNKROGOWIIXEAQ-UHFFFAOYSA-N 0.000 claims description 2
- HNOOCMSVOYKNLF-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-cyclopropylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NC2CC2)CC1 HNOOCMSVOYKNLF-UHFFFAOYSA-N 0.000 claims description 2
- NGJOSVSANIDIAK-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-ethoxyacetamide Chemical compound C1CN(CC(=O)NOCC)CCN1C(=O)N1C(C=2C(=CC(=CC=2)C(F)(F)F)OCC)=NC(C=2C=CC(Cl)=CC=2)C1C1=CC=C(Cl)C=C1 NGJOSVSANIDIAK-UHFFFAOYSA-N 0.000 claims description 2
- FHLUHUAVLUVQDQ-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-methyl-n-propan-2-ylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(C)C(C)C)CC1 FHLUHUAVLUVQDQ-UHFFFAOYSA-N 0.000 claims description 2
- TWDQXWQGTUWDMO-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NC)CC1 TWDQXWQGTUWDMO-UHFFFAOYSA-N 0.000 claims description 2
- CQLDSBZXVVUVNB-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-phenylmethoxyacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NOCC=2C=CC=CC=2)CC1 CQLDSBZXVVUVNB-UHFFFAOYSA-N 0.000 claims description 2
- LCQJPQHYYVXJSP-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]acetonitrile;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC#N)CC1 LCQJPQHYYVXJSP-UHFFFAOYSA-N 0.000 claims description 2
- ULTUCEUWZCEGDC-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-(1-methoxypropan-2-yl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)NC(C)COC)CC1 ULTUCEUWZCEGDC-UHFFFAOYSA-N 0.000 claims description 2
- GDDCHSMTZROILQ-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-(2,2,2-trifluoroethyl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)NCC(F)(F)F)CC1 GDDCHSMTZROILQ-UHFFFAOYSA-N 0.000 claims description 2
- CODMIFWNDYMESN-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-(2-methoxyethyl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)NCCOC)CC1 CODMIFWNDYMESN-UHFFFAOYSA-N 0.000 claims description 2
- GPEZKHJBESZSIU-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-(cyanomethyl)-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)N(C)CC#N)CC1 GPEZKHJBESZSIU-UHFFFAOYSA-N 0.000 claims description 2
- BHLFBHMJNDFAFF-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-methoxyacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)NOC)CC1 BHLFBHMJNDFAFF-UHFFFAOYSA-N 0.000 claims description 2
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- XPYOFGQFWWNUBO-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-phenylmethoxyacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)NOCC=2C=CC=CC=2)CC1 XPYOFGQFWWNUBO-UHFFFAOYSA-N 0.000 claims description 2
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- WXPUTFIZBWJHEZ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C=2C=CC(F)=CC=2)CC1 WXPUTFIZBWJHEZ-UHFFFAOYSA-N 0.000 claims description 2
- ZHZKRKMEDDRNFU-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(4-pyrrolidin-1-ylpiperidin-1-yl)sulfonylpiperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)N2CCC(CC2)N2CCCC2)CC1 ZHZKRKMEDDRNFU-UHFFFAOYSA-N 0.000 claims description 2
- CFDTYCNQCXVVQW-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(5-chlorothiophen-2-yl)sulfonylpiperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)C=2SC(Cl)=CC=2)CC1 CFDTYCNQCXVVQW-UHFFFAOYSA-N 0.000 claims description 2
- MNRSILSXEFWHLZ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(piperazin-1-ylmethyl)piperidin-1-yl]methanone;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(CN2CCNCC2)CC1 MNRSILSXEFWHLZ-UHFFFAOYSA-N 0.000 claims description 2
- FUNAOJIRVXDUMK-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)C2=C(ON=C2C)C)CC1 FUNAOJIRVXDUMK-UHFFFAOYSA-N 0.000 claims description 2
- AGUJPMSOQCRQRS-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCN(C)C)CC1 AGUJPMSOQCRQRS-UHFFFAOYSA-N 0.000 claims description 2
- NJMZSGKHDFHEFC-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[2-[di(propan-2-yl)amino]ethyl]piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCN(C(C)C)C(C)C)CC1 NJMZSGKHDFHEFC-UHFFFAOYSA-N 0.000 claims description 2
- QJWCCFBVMHMPCP-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonylpiperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)N2CCN(CCO)CC2)CC1 QJWCCFBVMHMPCP-UHFFFAOYSA-N 0.000 claims description 2
- VVMZUOLGUJFDQF-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-5-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(diethylaminomethyl)phenyl]methanone;hydrochloride Chemical compound Cl.CCOC1=CC=C(C(F)(F)F)C=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C1=CC=C(CN(CC)CC)C=C1 VVMZUOLGUJFDQF-UHFFFAOYSA-N 0.000 claims description 2
- JGCGRBGCQKSDRZ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-5-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(morpholin-4-ylmethyl)phenyl]methanone Chemical compound CCOC1=CC=C(C(F)(F)F)C=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C=C1)=CC=C1CN1CCOCC1 JGCGRBGCQKSDRZ-UHFFFAOYSA-N 0.000 claims description 2
- GBWGBEJPLFJORW-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-5-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCOC1=CC=C(C(F)(F)F)C=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C=C1)=CC=C1CN1CCC(N2CCCC2)CC1 GBWGBEJPLFJORW-UHFFFAOYSA-N 0.000 claims description 2
- HLFWHMPQNPTCNV-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-5-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]phenyl]methanone;hydrochloride Chemical compound Cl.CCOC1=CC=C(C(F)(F)F)C=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C=C1)=CC=C1CN1CCN(CCO)CC1 HLFWHMPQNPTCNV-UHFFFAOYSA-N 0.000 claims description 2
- OSPXDEOYPPCUHS-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-propan-2-yloxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(morpholin-4-ylmethyl)phenyl]methanone;hydrochloride Chemical compound Cl.CC(C)OC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C=C1)=CC=C1CN1CCOCC1 OSPXDEOYPPCUHS-UHFFFAOYSA-N 0.000 claims description 2
- VDZWKQHTAXLIMD-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-propan-2-yloxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]phenyl]methanone;hydrochloride Chemical compound Cl.CC(C)OC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C=C1)=CC=C1CN1CCN(CCO)CC1 VDZWKQHTAXLIMD-UHFFFAOYSA-N 0.000 claims description 2
- GFLVMDJMSBFNQV-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-(1,5-dimethylpyrazol-3-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)C2=NN(C)C(C)=C2)CC1 GFLVMDJMSBFNQV-UHFFFAOYSA-N 0.000 claims description 2
- ALXLMBKMYZDLIM-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-(3,5-dimethyl-1,2-oxazol-4-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)C2=C(ON=C2C)C)CC1 ALXLMBKMYZDLIM-UHFFFAOYSA-N 0.000 claims description 2
- CWPYLWWBADPYPY-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-(4-methylthiadiazol-5-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)C2=C(N=NS2)C)CC1 CWPYLWWBADPYPY-UHFFFAOYSA-N 0.000 claims description 2
- AXTHQJXVOMITRP-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-(furan-3-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)C2=COC=C2)CC1 AXTHQJXVOMITRP-UHFFFAOYSA-N 0.000 claims description 2
- MKLIKEOAEZXBJE-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-(oxolan-2-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)C2OCCC2)CC1 MKLIKEOAEZXBJE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- WDAXYOUAHWVMJS-UHFFFAOYSA-N ethyl 1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)N1C(C=2C(=CC(=CC=2)C(F)(F)F)OCC)=NC(C=2C=CC(Cl)=CC=2)C1C1=CC=C(Cl)C=C1 WDAXYOUAHWVMJS-UHFFFAOYSA-N 0.000 claims description 2
- RSNRCWOIVNOSCQ-UHFFFAOYSA-N ethyl 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C(=O)N1C(C=2C(=CC(=CC=2)C(F)(F)F)OCC)=NC(C=2C=CC(Cl)=CC=2)C1C1=CC=C(Cl)C=C1 RSNRCWOIVNOSCQ-UHFFFAOYSA-N 0.000 claims description 2
- UMGYZKMHTDCUBS-UHFFFAOYSA-N methyl 1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]pyrrolidine-2-carboxylate Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1C(C(=O)OC)CCC1 UMGYZKMHTDCUBS-UHFFFAOYSA-N 0.000 claims description 2
- YFTNAFWQFPPLOP-UHFFFAOYSA-N methyl 1-[[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-5-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]phenyl]methyl]pyrrolidine-2-carboxylate;hydrochloride Chemical compound Cl.CCOC1=CC=C(C(F)(F)F)C=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C=C1)=CC=C1CN1C(C(=O)OC)CCC1 YFTNAFWQFPPLOP-UHFFFAOYSA-N 0.000 claims description 2
- STBXVEIMIGNANG-UHFFFAOYSA-N methyl 3-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]sulfonylthiophene-2-carboxylate Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)C2=C(SC=C2)C(=O)OC)CC1 STBXVEIMIGNANG-UHFFFAOYSA-N 0.000 claims description 2
- QGUHPQDVTOBVOR-UHFFFAOYSA-N n-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-2-(3-hydroxypiperidin-1-yl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NC(=O)CN2CC(O)CCC2)CC1 QGUHPQDVTOBVOR-UHFFFAOYSA-N 0.000 claims description 2
- WGKDMLSGGRRUPH-UHFFFAOYSA-N n-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-2-(3-oxopiperazin-1-yl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NC(=O)CN2CC(=O)NCC2)CC1 WGKDMLSGGRRUPH-UHFFFAOYSA-N 0.000 claims description 2
- KLPNGRRRAHCMLX-UHFFFAOYSA-N n-[1-[[4-[4,5-bis(4-chlorophenyl)-2-[2-propan-2-yloxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]phenyl]methyl]piperidin-4-yl]acetamide;hydrochloride Chemical compound Cl.CC(C)OC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C=C1)=CC=C1CN1CCC(NC(C)=O)CC1 KLPNGRRRAHCMLX-UHFFFAOYSA-N 0.000 claims description 2
- IIKFXOLJMNWWCH-UHFFFAOYSA-N piperidine-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCN(C(O)=O)CC1 IIKFXOLJMNWWCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 5
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 4
- NTSDJVFOVNGESW-UHFFFAOYSA-N 1-(4-acetylpiperazin-1-yl)-2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CCN(CC2)C(C)=O)CC1 NTSDJVFOVNGESW-UHFFFAOYSA-N 0.000 claims 1
- RRRGLTISNLQCMJ-UHFFFAOYSA-N 1-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-3-methylthiourea Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NC(=S)NC)CC1 RRRGLTISNLQCMJ-UHFFFAOYSA-N 0.000 claims 1
- RAIZKZVXLRAXNS-UHFFFAOYSA-N 1-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-3-phenylthiourea Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NC(=S)NC=2C=CC=CC=2)CC1 RAIZKZVXLRAXNS-UHFFFAOYSA-N 0.000 claims 1
- VXTBVLQZHFRXOP-UHFFFAOYSA-N 1-[2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-oxoethyl]piperidine-3-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN2CC(CCC2)C(N)=O)CC1 VXTBVLQZHFRXOP-UHFFFAOYSA-N 0.000 claims 1
- ZPXHTINOYDOZEJ-UHFFFAOYSA-N 1-[2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN2CCC(CC2)C(N)=O)CC1 ZPXHTINOYDOZEJ-UHFFFAOYSA-N 0.000 claims 1
- HINGKKKFIYTTGE-UHFFFAOYSA-N 1-[2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]acetyl]piperidine-3-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CC(CCC2)C(N)=O)CC1 HINGKKKFIYTTGE-UHFFFAOYSA-N 0.000 claims 1
- YMLLKWUILYYKOD-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-(2-hydroxyethylamino)ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CNCCO)CC1 YMLLKWUILYYKOD-UHFFFAOYSA-N 0.000 claims 1
- WAMDOIWVJLGUAY-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-(2-methoxyethylamino)ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CNCCOC)CC1 WAMDOIWVJLGUAY-UHFFFAOYSA-N 0.000 claims 1
- VWXMQZICDXSSKF-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-(3-hydroxypiperidin-1-yl)ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN2CC(O)CCC2)CC1 VWXMQZICDXSSKF-UHFFFAOYSA-N 0.000 claims 1
- UZKAHAPQWFBQFA-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-(methylamino)ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CNC)CC1 UZKAHAPQWFBQFA-UHFFFAOYSA-N 0.000 claims 1
- YJNUMKBPOCKUIU-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-[1,3-dioxolan-2-ylmethyl(methyl)amino]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN(C)CC2OCCO2)CC1 YJNUMKBPOCKUIU-UHFFFAOYSA-N 0.000 claims 1
- FELIVOLRHFFPFT-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-[4-(hydroxymethyl)piperidin-1-yl]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN2CCC(CO)CC2)CC1 FELIVOLRHFFPFT-UHFFFAOYSA-N 0.000 claims 1
- OINOXAKBYKWQPE-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-[bis(2-hydroxyethyl)amino]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN(CCO)CCO)CC1 OINOXAKBYKWQPE-UHFFFAOYSA-N 0.000 claims 1
- IHTYVRVGRGXIHY-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-[bis(2-methoxyethyl)amino]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN(CCOC)CCOC)CC1 IHTYVRVGRGXIHY-UHFFFAOYSA-N 0.000 claims 1
- DQEROOWICKPTND-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-methoxyethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)COC)CC1 DQEROOWICKPTND-UHFFFAOYSA-N 0.000 claims 1
- REXMXXBLUIZYQT-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazine-1-carbonyl]piperidine-4-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)N2CCC(CC2)C(N)=O)CC1 REXMXXBLUIZYQT-UHFFFAOYSA-N 0.000 claims 1
- NQPNQJZMBXRNCW-UHFFFAOYSA-N 1-benzyl-4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-2-one;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CC(=O)N(CC=2C=CC=CC=2)CC1 NQPNQJZMBXRNCW-UHFFFAOYSA-N 0.000 claims 1
- LBGQGYKSBSHYEA-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)-1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN2CCN(CC2)C(C)=O)CC1 LBGQGYKSBSHYEA-UHFFFAOYSA-N 0.000 claims 1
- BAVQQMYMRMKNON-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)-n-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NC(=O)CN2CCN(CC2)C(C)=O)CC1 BAVQQMYMRMKNON-UHFFFAOYSA-N 0.000 claims 1
- INXKEGMXCZBZMY-UHFFFAOYSA-N 2-[4-[2-[[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]sulfonyl]ethyl]piperazin-1-yl]ethanol;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1S(=O)(=O)CCN1CCN(CCO)CC1 INXKEGMXCZBZMY-UHFFFAOYSA-N 0.000 claims 1
- KFJJVBPTPGFRCO-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-1-(3-hydroxypiperidin-1-yl)ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CC(O)CCC2)CC1 KFJJVBPTPGFRCO-UHFFFAOYSA-N 0.000 claims 1
- KOIMCAPFHQFBHV-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-1-piperidin-1-ylethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CCCCC2)CC1 KOIMCAPFHQFBHV-UHFFFAOYSA-N 0.000 claims 1
- YNRACKVTYHOPIG-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n,n-dimethylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(C)C)CC1 YNRACKVTYHOPIG-UHFFFAOYSA-N 0.000 claims 1
- QIGJYOMVPRYMHB-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n,n-dimethylethanesulfonamide;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCS(=O)(=O)N(C)C)CC1 QIGJYOMVPRYMHB-UHFFFAOYSA-N 0.000 claims 1
- ATEJZMYSUKZDSN-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(1-hydroxy-4-methylpentan-2-yl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NC(CO)CC(C)C)CC1 ATEJZMYSUKZDSN-UHFFFAOYSA-N 0.000 claims 1
- XXZAHFLSKCUSOH-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(1-methoxypropan-2-yl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NC(C)COC)CC1 XXZAHFLSKCUSOH-UHFFFAOYSA-N 0.000 claims 1
- KQSGNXWNJJCIPQ-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(2,2,2-trifluoroethyl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NCC(F)(F)F)CC1 KQSGNXWNJJCIPQ-UHFFFAOYSA-N 0.000 claims 1
- ILDNRBKSBADBSR-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(2-cyanoethyl)-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(C)CCC#N)CC1 ILDNRBKSBADBSR-UHFFFAOYSA-N 0.000 claims 1
- QBVKSPYMQCEKRG-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(2-methoxyethyl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NCCOC)CC1 QBVKSPYMQCEKRG-UHFFFAOYSA-N 0.000 claims 1
- HCVFRXGWSQSNTE-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(2-methylpropyl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NCC(C)C)CC1 HCVFRXGWSQSNTE-UHFFFAOYSA-N 0.000 claims 1
- QBLUEPJSLLJNQD-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(3-hydroxypropyl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NCCCO)CC1 QBLUEPJSLLJNQD-UHFFFAOYSA-N 0.000 claims 1
- ZXQRROQQVXOKIH-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(cyanomethyl)-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(C)CC#N)CC1 ZXQRROQQVXOKIH-UHFFFAOYSA-N 0.000 claims 1
- XKWMLLCLSSLJAR-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-(oxolan-2-ylmethyl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NCC2OCCC2)CC1 XKWMLLCLSSLJAR-UHFFFAOYSA-N 0.000 claims 1
- AXFCNUVWDCCBOI-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-methoxy-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N(C)OC)CC1 AXFCNUVWDCCBOI-UHFFFAOYSA-N 0.000 claims 1
- GSCHYMHIPYLQEB-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-methoxyacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)NOC)CC1 GSCHYMHIPYLQEB-UHFFFAOYSA-N 0.000 claims 1
- RLGDRYOGAMOMCS-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-n-propylacetamide Chemical compound C1CN(CC(=O)NCCC)CCN1C(=O)N1C(C=2C(=CC(=CC=2)C(F)(F)F)OCC)=NC(C=2C=CC(Cl)=CC=2)C1C1=CC=C(Cl)C=C1 RLGDRYOGAMOMCS-UHFFFAOYSA-N 0.000 claims 1
- AENZBYISSGOZDI-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(N)=O)CC1 AENZBYISSGOZDI-UHFFFAOYSA-N 0.000 claims 1
- LBVCBDILDVPPOO-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanesulfonamide;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCS(N)(=O)=O)CC1 LBVCBDILDVPPOO-UHFFFAOYSA-N 0.000 claims 1
- MOATXUKIKTWTKP-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C=2C(=CC=CN=2)C#N)CC1 MOATXUKIKTWTKP-UHFFFAOYSA-N 0.000 claims 1
- SPMCVMOJJXEZSU-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-1-(3-hydroxypiperidin-1-yl)ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)N2CC(O)CCC2)CC1 SPMCVMOJJXEZSU-UHFFFAOYSA-N 0.000 claims 1
- VLAHBHZQBPWVLV-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-1-[4-(trifluoromethyl)piperidin-1-yl]ethanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)N2CCC(CC2)C(F)(F)F)CC1 VLAHBHZQBPWVLV-UHFFFAOYSA-N 0.000 claims 1
- PNNVHVBOVLOBRS-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-(1-hydroxy-4-methylpentan-2-yl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)NC(CO)CC(C)C)CC1 PNNVHVBOVLOBRS-UHFFFAOYSA-N 0.000 claims 1
- IQCPDPHGEWITPU-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-(2-cyanoethyl)-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)N(C)CCC#N)CC1 IQCPDPHGEWITPU-UHFFFAOYSA-N 0.000 claims 1
- LFDQTBXTDLBOIL-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-(2-hydroxyethyl)-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)N(C)CCO)CC1 LFDQTBXTDLBOIL-UHFFFAOYSA-N 0.000 claims 1
- IQXDZQYVAZQWBA-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-(2-methylpropyl)acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)NCC(C)C)CC1 IQXDZQYVAZQWBA-UHFFFAOYSA-N 0.000 claims 1
- MRBWIPLARHRXHS-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-[(5-methylfuran-2-yl)methyl]acetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)NCC=2OC(C)=CC=2)CC1 MRBWIPLARHRXHS-UHFFFAOYSA-N 0.000 claims 1
- FZVLWLJYWZKHAC-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-methoxy-n-methylacetamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(NCC(=O)N(C)OC)CC1 FZVLWLJYWZKHAC-UHFFFAOYSA-N 0.000 claims 1
- ORWDRQGNASMTJL-UHFFFAOYSA-N 2-[[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]amino]-n-propylacetamide Chemical compound C1CC(NCC(=O)NCCC)CCN1C(=O)N1C(C=2C(=CC(=CC=2)C(F)(F)F)OCC)=NC(C=2C=CC(Cl)=CC=2)C1C1=CC=C(Cl)C=C1 ORWDRQGNASMTJL-UHFFFAOYSA-N 0.000 claims 1
- DIYOAFOOTUNZJN-UHFFFAOYSA-N 2-[[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]sulfonyl]-n,n-diethylethanamine;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1S(=O)(=O)CCN(CC)CC DIYOAFOOTUNZJN-UHFFFAOYSA-N 0.000 claims 1
- GBEWNNRCXVTBHZ-UHFFFAOYSA-N 3-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(N2C(NC3=CC=CC=C32)=O)CC1 GBEWNNRCXVTBHZ-UHFFFAOYSA-N 0.000 claims 1
- HARPEZGBOPBKKK-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-(1-methoxypropan-2-yl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NC(C)COC HARPEZGBOPBKKK-UHFFFAOYSA-N 0.000 claims 1
- GKYXLJBDFMPMLF-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-(2-hydroxyethyl)-n-methyl-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N(C)CCO GKYXLJBDFMPMLF-UHFFFAOYSA-N 0.000 claims 1
- AEJMYUVWCMZRON-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-(2-methoxyethyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NCCOC AEJMYUVWCMZRON-UHFFFAOYSA-N 0.000 claims 1
- GLUQEDUKBIZHPI-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-(2-pyridin-2-ylethyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NCCC1=CC=CC=N1 GLUQEDUKBIZHPI-UHFFFAOYSA-N 0.000 claims 1
- JCGOSNURLUPGIP-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-(3-hydroxypropyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NCCCO JCGOSNURLUPGIP-UHFFFAOYSA-N 0.000 claims 1
- FOMFABDEFZKSHH-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-(3-imidazol-1-ylpropyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NCCCN1C=NC=C1 FOMFABDEFZKSHH-UHFFFAOYSA-N 0.000 claims 1
- AQLBJTDAHDNQPN-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-(pyridin-3-ylmethyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NCC1=CC=CN=C1 AQLBJTDAHDNQPN-UHFFFAOYSA-N 0.000 claims 1
- LHZWMTIERCWSEH-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-[(1-ethylpyrrolidin-2-yl)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NCC1N(CC)CCC1 LHZWMTIERCWSEH-UHFFFAOYSA-N 0.000 claims 1
- AMQDVMNSFPLZRM-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-methoxy-n-methyl-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N(C)OC AMQDVMNSFPLZRM-UHFFFAOYSA-N 0.000 claims 1
- IQOFQSGQBFVBNT-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-methyl-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NC IQOFQSGQBFVBNT-UHFFFAOYSA-N 0.000 claims 1
- MBTRQLAEOBOYRO-UHFFFAOYSA-N 4-[2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-oxoethyl]piperazin-2-one Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN2CC(=O)NCC2)CC1 MBTRQLAEOBOYRO-UHFFFAOYSA-N 0.000 claims 1
- YEKLFMLKZXWMMY-UHFFFAOYSA-N 4-[2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]acetyl]piperazin-2-one Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(=O)N2CC(=O)NCC2)CC1 YEKLFMLKZXWMMY-UHFFFAOYSA-N 0.000 claims 1
- MYIAAVVOARILMW-UHFFFAOYSA-N 4-[2-[[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]sulfonyl]ethyl]morpholine;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1S(=O)(=O)CCN1CCOCC1 MYIAAVVOARILMW-UHFFFAOYSA-N 0.000 claims 1
- HJVWVSNQXSAAQJ-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]-1-(2-methoxyethyl)piperazin-2-one Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CC(=O)N(CCOC)CC1 HJVWVSNQXSAAQJ-UHFFFAOYSA-N 0.000 claims 1
- IEAJTKVIBAKADZ-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]-n-(2-methoxyethyl)piperazine-1-sulfonamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)NCCOC)CC1 IEAJTKVIBAKADZ-UHFFFAOYSA-N 0.000 claims 1
- YEQJREIXODTFNO-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]-n-(2-methylpropyl)piperazine-1-sulfonamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)NCC(C)C)CC1 YEQJREIXODTFNO-UHFFFAOYSA-N 0.000 claims 1
- KVDNVNFGTTXVFE-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]-n-(oxolan-2-ylmethyl)piperazine-1-sulfonamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)NCC2OCCC2)CC1 KVDNVNFGTTXVFE-UHFFFAOYSA-N 0.000 claims 1
- HDWAWXHTRJAHRX-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]-n-methylpiperazine-1-carbothioamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=S)NC)CC1 HDWAWXHTRJAHRX-UHFFFAOYSA-N 0.000 claims 1
- VCJLCHZOCWJUNP-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]-n-phenylpiperazine-1-carbothioamide Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=S)NC=2C=CC=CC=2)CC1 VCJLCHZOCWJUNP-UHFFFAOYSA-N 0.000 claims 1
- OIMJCEYUFFYQSQ-UHFFFAOYSA-N 4-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazine-1-carbonyl]piperazin-2-one Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)N2CC(=O)NCC2)CC1 OIMJCEYUFFYQSQ-UHFFFAOYSA-N 0.000 claims 1
- JQEHIFIBJWHIFW-UHFFFAOYSA-N 4-[[4-[4,5-bis(4-chlorophenyl)-2-[2-propan-2-yloxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]phenyl]methyl]piperazin-2-one;hydrochloride Chemical compound Cl.CC(C)OC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C=C1)=CC=C1CN1CC(=O)NCC1 JQEHIFIBJWHIFW-UHFFFAOYSA-N 0.000 claims 1
- YCHBIEKEWNEPIX-UHFFFAOYSA-N 6-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C=2N=CC(=CC=2)C#N)CC1 YCHBIEKEWNEPIX-UHFFFAOYSA-N 0.000 claims 1
- WSDWKCIUJGQZFE-UHFFFAOYSA-N [1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-methyl-1-oxopropan-2-yl] acetate Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)C(C)(C)OC(C)=O)CC1 WSDWKCIUJGQZFE-UHFFFAOYSA-N 0.000 claims 1
- TVTLQEQPTUOKGT-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC2(OCCO2)CC1 TVTLQEQPTUOKGT-UHFFFAOYSA-N 0.000 claims 1
- GOHWZWUGBHXOGV-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(4-butylsulfonylpiperazin-1-yl)methanone Chemical compound C1CN(S(=O)(=O)CCCC)CCN1C(=O)N1C(C=2C(=CC(=CC=2)C(F)(F)F)OCC)=NC(C=2C=CC(Cl)=CC=2)C1C1=CC=C(Cl)C=C1 GOHWZWUGBHXOGV-UHFFFAOYSA-N 0.000 claims 1
- ODUFUQGOMHVBET-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(4-morpholin-4-ylsulfonylpiperazin-1-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)N2CCOCC2)CC1 ODUFUQGOMHVBET-UHFFFAOYSA-N 0.000 claims 1
- BSMVNJNBGDPLJO-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(4-phenylpiperidin-1-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(C=2C=CC=CC=2)CC1 BSMVNJNBGDPLJO-UHFFFAOYSA-N 0.000 claims 1
- WMDMSSWUZRXHTG-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(4-piperidin-1-ylsulfonylpiperazin-1-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)N2CCCCC2)CC1 WMDMSSWUZRXHTG-UHFFFAOYSA-N 0.000 claims 1
- XUMOWPYPPBBYGC-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(4-propan-2-ylsulfonylpiperazin-1-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)C(C)C)CC1 XUMOWPYPPBBYGC-UHFFFAOYSA-N 0.000 claims 1
- AGXGFLVIFZYEPO-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(4-pyridin-4-ylpiperazin-1-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C=2C=CN=CC=2)CC1 AGXGFLVIFZYEPO-UHFFFAOYSA-N 0.000 claims 1
- XHTVWKWDMXEDAZ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(4-pyrrolidin-1-ylsulfonylpiperazin-1-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)N2CCCC2)CC1 XHTVWKWDMXEDAZ-UHFFFAOYSA-N 0.000 claims 1
- BMOXVSPXJAECSB-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(4-thiophen-2-ylsulfonylpiperazin-1-yl)methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)C=2SC=CC=2)CC1 BMOXVSPXJAECSB-UHFFFAOYSA-N 0.000 claims 1
- HPPBFVDOYBMGRS-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(2,5-dichlorothiophen-3-yl)sulfonylpiperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)C2=C(SC(Cl)=C2)Cl)CC1 HPPBFVDOYBMGRS-UHFFFAOYSA-N 0.000 claims 1
- PAHOPVLKVGUHGH-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(2-methylsulfonylethyl)piperazin-1-yl]methanone;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCS(C)(=O)=O)CC1 PAHOPVLKVGUHGH-UHFFFAOYSA-N 0.000 claims 1
- KMEDWOHVELFZGS-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(2-morpholin-4-ylethyl)piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCN2CCOCC2)CC1 KMEDWOHVELFZGS-UHFFFAOYSA-N 0.000 claims 1
- ANVAHHLBXHTMLW-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(2-piperidin-1-ylethyl)piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCN2CCCCC2)CC1 ANVAHHLBXHTMLW-UHFFFAOYSA-N 0.000 claims 1
- HVHXOWJMRXYOCP-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(2-pyrrolidin-1-ylethyl)piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCN2CCCC2)CC1 HVHXOWJMRXYOCP-UHFFFAOYSA-N 0.000 claims 1
- IENPFQYAANHLIH-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(3,3,3-trifluoro-2-hydroxypropyl)piperazin-1-yl]methanone;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(O)C(F)(F)F)CC1 IENPFQYAANHLIH-UHFFFAOYSA-N 0.000 claims 1
- VTODHAYKVICOKB-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(3,3,3-trifluoropropyl)piperazin-1-yl]methanone;hydrochloride Chemical compound Cl.CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCC(F)(F)F)CC1 VTODHAYKVICOKB-UHFFFAOYSA-N 0.000 claims 1
- KJFQJCIJRMMCJI-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(3-piperidin-1-ylpropyl)piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCCN2CCCCC2)CC1 KJFQJCIJRMMCJI-UHFFFAOYSA-N 0.000 claims 1
- HWVOEJWMPGKSCQ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(3-pyrrolidin-1-ylpropyl)piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCCN2CCCC2)CC1 HWVOEJWMPGKSCQ-UHFFFAOYSA-N 0.000 claims 1
- SZIUGQAOGWXIDC-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(4-propylphenyl)sulfonylpiperazin-1-yl]methanone Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)N1CCN(C(=O)N2C(=NC(C2C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C=2C(=CC(=CC=2)C(F)(F)F)OCC)CC1 SZIUGQAOGWXIDC-UHFFFAOYSA-N 0.000 claims 1
- UHTZUSOEDCHFRN-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(5-chloro-1,3-dimethylpyrazol-4-yl)sulfonylpiperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)C2=C(N(C)N=C2C)Cl)CC1 UHTZUSOEDCHFRN-UHFFFAOYSA-N 0.000 claims 1
- HYSCMEGJZMGCLW-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(oxolan-2-ylmethyl)piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC2OCCC2)CC1 HYSCMEGJZMGCLW-UHFFFAOYSA-N 0.000 claims 1
- LGXDPMUBIGIGQG-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(pyridin-4-ylmethyl)piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC=2C=CN=CC=2)CC1 LGXDPMUBIGIGQG-UHFFFAOYSA-N 0.000 claims 1
- KQPXLFKTKFUEFZ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(trifluoromethylsulfonyl)piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)C(F)(F)F)CC1 KQPXLFKTKFUEFZ-UHFFFAOYSA-N 0.000 claims 1
- RTCPQZJEAKVSFG-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[(1-methylpiperidin-3-yl)methyl]piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC2CN(C)CCC2)CC1 RTCPQZJEAKVSFG-UHFFFAOYSA-N 0.000 claims 1
- UGGKGXFEVHJJCV-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[(2,4-dimethyl-1,3-thiazol-5-yl)sulfonyl]piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(S(=O)(=O)C2=C(N=C(C)S2)C)CC1 UGGKGXFEVHJJCV-UHFFFAOYSA-N 0.000 claims 1
- IUFNDDQDOBQUPA-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[2-(diethylamino)ethyl]piperazin-1-yl]methanone Chemical compound CCOC1=CC(C(F)(F)F)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CCN(CC)CC)CC1 IUFNDDQDOBQUPA-UHFFFAOYSA-N 0.000 claims 1
- IBZXBAGFPOOVFD-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[2-(dipropylamino)ethyl]piperazin-1-yl]methanone Chemical compound C1CN(CCN(CCC)CCC)CCN1C(=O)N1C(C=2C(=CC(=CC=2)C(F)(F)F)OCC)=NC(C=2C=CC(Cl)=CC=2)C1C1=CC=C(Cl)C=C1 IBZXBAGFPOOVFD-UHFFFAOYSA-N 0.000 claims 1
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- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- SFQSZZGLAJRHHB-UHFFFAOYSA-N piperazin-2-one;hydrochloride Chemical compound Cl.O=C1CNCCN1 SFQSZZGLAJRHHB-UHFFFAOYSA-N 0.000 description 1
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 208000023958 prostate neoplasm Diseases 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000025915 regulation of apoptotic process Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- XBMXAAOSSFWPED-UHFFFAOYSA-N tert-butyl 4-morpholin-4-ylsulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)N1CCOCC1 XBMXAAOSSFWPED-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- C07D233/20—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 substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- 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
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
-
- 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US47935103P | 2003-06-17 | 2003-06-17 | |
US60/479,351 | 2003-06-17 | ||
PCT/EP2004/006176 WO2005003097A1 (en) | 2003-06-17 | 2004-06-08 | Cis-2,4,5-triaryl-imidazolines |
Publications (1)
Publication Number | Publication Date |
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CA2528119A1 true CA2528119A1 (en) | 2005-01-13 |
Family
ID=33563793
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA002528119A Abandoned CA2528119A1 (en) | 2003-06-17 | 2004-06-08 | Cis-2,4,5-triaryl-imidazolines |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP1638942A1 (ko) |
JP (1) | JP2006527712A (ko) |
KR (1) | KR100768021B1 (ko) |
CN (1) | CN100465163C (ko) |
AR (1) | AR044703A1 (ko) |
AU (1) | AU2004254187A1 (ko) |
BR (1) | BRPI0411841A (ko) |
CA (1) | CA2528119A1 (ko) |
CL (1) | CL2004001484A1 (ko) |
MX (1) | MXPA05013279A (ko) |
RU (1) | RU2319696C2 (ko) |
TW (1) | TW200510387A (ko) |
WO (1) | WO2005003097A1 (ko) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
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RU2411238C2 (ru) * | 2005-03-16 | 2011-02-10 | Ф.Хоффманн-Ля Рош Аг | Цис-2,4,5-триарилимидазолины и их применение в качестве противораковых лекарственных средств |
BRPI0619236A2 (pt) * | 2005-12-01 | 2011-09-20 | Hoffmann La Roche | derivados de 2,4,5-trifenil imidazolina, composição farmacêutica que os compreende, uso e processo para a sìntese dos mesmos |
US8114095B2 (en) * | 2006-11-10 | 2012-02-14 | Bausch & Lomb Incorporated | Intraocular lens injection apparatus and method |
MX2009006397A (es) | 2006-12-14 | 2009-08-13 | Daiichi Sankyo Co Ltd | Derivados de imidazotiazol. |
US7625895B2 (en) * | 2007-04-12 | 2009-12-01 | Hoffmann-Le Roche Inc. | Diphenyl-dihydro-imidazopyridinones |
WO2009151069A1 (ja) | 2008-06-12 | 2009-12-17 | 第一三共株式会社 | 4,7-ジアザスピロ[2.5]オクタン環構造を有するイミダゾチアゾール誘導体 |
MX2011007598A (es) | 2009-01-16 | 2011-08-08 | Daiichi Sankyo Co Ltd | Derivados de imidazotiazol que tienen estructura de anillo de prolina. |
IT1396520B1 (it) | 2009-12-10 | 2012-12-14 | Nuovo Pignone Spa | Accoppiamento per bilanciamento rotore |
US20140328893A1 (en) | 2011-10-11 | 2014-11-06 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Nutlin compounds for use in the treatment of pulmonary hypertension |
WO2017201449A1 (en) | 2016-05-20 | 2017-11-23 | Genentech, Inc. | Protac antibody conjugates and methods of use |
EP3883925A4 (en) * | 2018-11-20 | 2021-12-29 | Sironax Ltd | Cyclic ureas |
WO2023056069A1 (en) | 2021-09-30 | 2023-04-06 | Angiex, Inc. | Degrader-antibody conjugates and methods of using same |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CA2030158A1 (en) * | 1989-11-22 | 1991-05-23 | Nahed K. Ahmed | Cancer treatments |
DE10043456A1 (de) * | 2000-09-04 | 2002-03-14 | Merck Patent Gmbh | Verwendung von Ectoin oder Ectoin-Derivaten zur Stabilisierung von p53 |
WO2003051359A1 (en) * | 2001-12-18 | 2003-06-26 | F.Hoffmann-La Roche Ag | Cis-2,4,5- triphenyl-imidazolines and their use in the treatment of tumors |
-
2004
- 2004-06-08 KR KR1020057024295A patent/KR100768021B1/ko not_active IP Right Cessation
- 2004-06-08 RU RU2006100730/04A patent/RU2319696C2/ru not_active IP Right Cessation
- 2004-06-08 BR BRPI0411841-3A patent/BRPI0411841A/pt not_active IP Right Cessation
- 2004-06-08 JP JP2006515856A patent/JP2006527712A/ja not_active Ceased
- 2004-06-08 WO PCT/EP2004/006176 patent/WO2005003097A1/en active Application Filing
- 2004-06-08 CN CNB2004800170350A patent/CN100465163C/zh not_active Expired - Fee Related
- 2004-06-08 EP EP04739704A patent/EP1638942A1/en not_active Withdrawn
- 2004-06-08 MX MXPA05013279A patent/MXPA05013279A/es unknown
- 2004-06-08 CA CA002528119A patent/CA2528119A1/en not_active Abandoned
- 2004-06-08 AU AU2004254187A patent/AU2004254187A1/en not_active Abandoned
- 2004-06-11 TW TW093116988A patent/TW200510387A/zh unknown
- 2004-06-15 CL CL200401484A patent/CL2004001484A1/es unknown
- 2004-06-15 AR ARP040102068A patent/AR044703A1/es not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
CN1809538A (zh) | 2006-07-26 |
KR100768021B1 (ko) | 2007-10-18 |
EP1638942A1 (en) | 2006-03-29 |
AU2004254187A1 (en) | 2005-01-13 |
TW200510387A (en) | 2005-03-16 |
RU2006100730A (ru) | 2006-08-10 |
MXPA05013279A (es) | 2006-03-09 |
AR044703A1 (es) | 2005-09-21 |
CN100465163C (zh) | 2009-03-04 |
WO2005003097A1 (en) | 2005-01-13 |
BRPI0411841A (pt) | 2006-08-08 |
JP2006527712A (ja) | 2006-12-07 |
KR20060021902A (ko) | 2006-03-08 |
RU2319696C2 (ru) | 2008-03-20 |
CL2004001484A1 (es) | 2005-05-27 |
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