JP2005511766A5 - - Google Patents
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- JP2005511766A5 JP2005511766A5 JP2003552292A JP2003552292A JP2005511766A5 JP 2005511766 A5 JP2005511766 A5 JP 2005511766A5 JP 2003552292 A JP2003552292 A JP 2003552292A JP 2003552292 A JP2003552292 A JP 2003552292A JP 2005511766 A5 JP2005511766 A5 JP 2005511766A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- dihydro
- bis
- chloro
- imidazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000004193 piperazinyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims 11
- 125000001246 bromo group Chemical group Br* 0.000 claims 10
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- CPFNRKGBALNLGO-UHFFFAOYSA-N 4-(3-hydroxybutan-2-yl)piperazine-1-carbaldehyde Chemical compound OC(C(C)N1CCN(CC1)C=O)C CPFNRKGBALNLGO-UHFFFAOYSA-N 0.000 claims 2
- JQEGHZZGJKDIEV-UHFFFAOYSA-N COC(=O)N1C(=NC(C1C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)Cl)C1=C(C=C(C=C1)OC)OCC Chemical compound COC(=O)N1C(=NC(C1C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)Cl)C1=C(C=C(C=C1)OC)OCC JQEGHZZGJKDIEV-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims 1
- OPZRTSZCJXIROV-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-(2,3-dimethoxyphenyl)-4,5-dihydroimidazol-1-yl]-2-methylpropan-1-one Chemical compound COC1=CC=CC(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)C(C)C)=C1OC OPZRTSZCJXIROV-UHFFFAOYSA-N 0.000 claims 1
- GJHWFURXLYZLSP-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-(2,4-dimethoxyphenyl)-4,5-dihydroimidazol-1-yl]-2,2-dimethylpropan-1-one Chemical compound COC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C)(C)C GJHWFURXLYZLSP-UHFFFAOYSA-N 0.000 claims 1
- FLBAPFPVYFYDFA-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-(2,4-dimethoxyphenyl)-4,5-dihydroimidazol-1-yl]-2-methylpropan-1-one Chemical compound COC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C)C FLBAPFPVYFYDFA-UHFFFAOYSA-N 0.000 claims 1
- OEHLHAMPBIBYAC-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-(2,4-dimethoxyphenyl)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound COC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(C)=O OEHLHAMPBIBYAC-UHFFFAOYSA-N 0.000 claims 1
- JICOEQLXABNUFN-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-(2-methoxy-3-methyl-5-morpholin-4-ylphenyl)-4,5-dihydroimidazol-1-yl]-2-methylpropan-1-one Chemical compound COC1=C(C)C=C(N2CCOCC2)C=C1C(N1C(=O)C(C)C)=NC(C=2C=CC(Cl)=CC=2)C1C1=CC=C(Cl)C=C1 JICOEQLXABNUFN-UHFFFAOYSA-N 0.000 claims 1
- SRSWLWHASCATGS-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-(2-methoxyphenyl)-4,5-dihydroimidazol-1-yl]-2-methylpropan-1-one Chemical compound COC1=CC=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C)C SRSWLWHASCATGS-UHFFFAOYSA-N 0.000 claims 1
- DUOFTOMXBGMGDU-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-(2-propan-2-yloxyphenyl)-4,5-dihydroimidazol-1-yl]-2-methylpropan-1-one Chemical compound CC(C)OC1=CC=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C)C DUOFTOMXBGMGDU-UHFFFAOYSA-N 0.000 claims 1
- RBPDLJJZVJQRGD-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-(4-methoxyphenyl)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(C)=O RBPDLJJZVJQRGD-UHFFFAOYSA-N 0.000 claims 1
- GUWSENNVDHRDKJ-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-(4-methylphenyl)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1C(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=C(C)C=C1 GUWSENNVDHRDKJ-UHFFFAOYSA-N 0.000 claims 1
- HEIYAGGHEDLEOG-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-[3-(hydroxymethyl)-5-(methoxymethyl)phenyl]-4,5-dihydroimidazol-1-yl]ethanone Chemical compound COCC1=CC(CO)=CC(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(C)=O)=C1 HEIYAGGHEDLEOG-UHFFFAOYSA-N 0.000 claims 1
- DYICVQZJUJXORL-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-[3-(hydroxymethyl)-5-methoxyphenyl]-4,5-dihydroimidazol-1-yl]-2-methylpropan-1-one Chemical compound COC1=CC(CO)=CC(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)C(C)C)=C1 DYICVQZJUJXORL-UHFFFAOYSA-N 0.000 claims 1
- QFWUHFIENNVEOT-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-[3-methoxy-5-(methoxymethyl)phenyl]-4,5-dihydroimidazol-1-yl]-2-methylpropan-1-one Chemical compound COCC1=CC(OC)=CC(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)C(C)C)=C1 QFWUHFIENNVEOT-UHFFFAOYSA-N 0.000 claims 1
- WDHXVBYTXCIIGQ-UHFFFAOYSA-N 1-[4,5-bis(4-chlorophenyl)-2-[5-(ethoxymethyl)-2,4-dimethoxyphenyl]-4,5-dihydroimidazol-1-yl]-2-methylpropan-1-one Chemical compound C1=C(OC)C(COCC)=CC(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)C(C)C)=C1OC WDHXVBYTXCIIGQ-UHFFFAOYSA-N 0.000 claims 1
- JOWZHPPULRVFTI-UHFFFAOYSA-N 1-[4-[2-(4-chloro-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CCOC1=CC(Cl)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(C)=O)CC1 JOWZHPPULRVFTI-UHFFFAOYSA-N 0.000 claims 1
- XKQFXQJADXNRRY-UHFFFAOYSA-N 1-[4-[4,5-bis(4-bromophenyl)-2-(2-ethoxy-4-methoxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Br)=CC=2)C(C=2C=CC(Br)=CC=2)N1C(=O)N1CCN(C(C)=O)CC1 XKQFXQJADXNRRY-UHFFFAOYSA-N 0.000 claims 1
- ZWAVTSQWGCHVRF-UHFFFAOYSA-N 1-[4-[4,5-bis(4-bromophenyl)-2-(2-ethoxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CCOC1=CC=CC=C1C1=NC(C=2C=CC(Br)=CC=2)C(C=2C=CC(Br)=CC=2)N1C(=O)N1CCN(C(C)=O)CC1 ZWAVTSQWGCHVRF-UHFFFAOYSA-N 0.000 claims 1
- FMLWPNZSQOCJSO-UHFFFAOYSA-N 1-[4-[4,5-bis(4-bromophenyl)-2-(2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CC(C)OC1=CC=CC=C1C1=NC(C=2C=CC(Br)=CC=2)C(C=2C=CC(Br)=CC=2)N1C(=O)N1CCN(C(C)=O)CC1 FMLWPNZSQOCJSO-UHFFFAOYSA-N 0.000 claims 1
- XWMVWRJFQBHCAS-UHFFFAOYSA-N 1-[4-[4,5-bis(4-bromophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Br)=CC=2)C(C=2C=CC(Br)=CC=2)N1C(=O)N1CCN(C(C)=O)CC1 XWMVWRJFQBHCAS-UHFFFAOYSA-N 0.000 claims 1
- KDUFTDHEWWQGKP-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-(4-ethoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CC(C)OC1=CC(OCC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(C)=O)CC1 KDUFTDHEWWQGKP-UHFFFAOYSA-N 0.000 claims 1
- FDINGKBVWPGGAZ-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]-2-methylpiperazin-1-yl]ethanone Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CC(C)N(C(C)=O)CC1 FDINGKBVWPGGAZ-UHFFFAOYSA-N 0.000 claims 1
- FSURKMTYYLTMRB-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2,3-dihydroxypropan-1-one Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)C(O)CO)CC1 FSURKMTYYLTMRB-UHFFFAOYSA-N 0.000 claims 1
- GNHDEVZIZDNBNG-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CO)CC1 GNHDEVZIZDNBNG-UHFFFAOYSA-N 0.000 claims 1
- IYDMGGPKSVWQRT-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(C)=O)CC1 IYDMGGPKSVWQRT-UHFFFAOYSA-N 0.000 claims 1
- XHOLLDFTWGNSLK-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]propan-2-one Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(CC(C)=O)CC1 XHOLLDFTWGNSLK-UHFFFAOYSA-N 0.000 claims 1
- MZPDHXGYWITRKI-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-(5-chloro-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CC(C)OC1=CC=C(Cl)C=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(C)=O)CC1 MZPDHXGYWITRKI-UHFFFAOYSA-N 0.000 claims 1
- MQIJXEFETCOWOJ-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-(5-ethoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CCOC1=CC=C(OC(C)C)C(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)N2CCN(CC2)C(C)=O)=C1 MQIJXEFETCOWOJ-UHFFFAOYSA-N 0.000 claims 1
- MQBSGIABKRDXTL-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-(2-fluoroethoxy)-4-methoxyphenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound FCCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(C)=O)CC1 MQBSGIABKRDXTL-UHFFFAOYSA-N 0.000 claims 1
- UULOZZMRJZRFKQ-UHFFFAOYSA-N 1-[5-(4-chlorophenyl)-2-(4-methoxyphenyl)-4-(4-nitrophenyl)-4,5-dihydroimidazol-1-yl]-2-methylpropan-1-one Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=CC(=CC=2)[N+]([O-])=O)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C)C UULOZZMRJZRFKQ-UHFFFAOYSA-N 0.000 claims 1
- OATVZKIQWCAKJW-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-1-(2-methylpropanoyl)-4,5-dihydroimidazol-2-yl]phenoxy]acetic acid Chemical compound CC(C)C(=O)N1C(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=C(OCC(O)=O)C=C1 OATVZKIQWCAKJW-UHFFFAOYSA-N 0.000 claims 1
- ATPUMWBTXBIDLR-UHFFFAOYSA-N 2-amino-1-[4-[4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]ethanone Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)CN)CC1 ATPUMWBTXBIDLR-UHFFFAOYSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- FMOICKVRFIVFSJ-UHFFFAOYSA-N 2-methyl-1-[2,4,5-tris(4-chlorophenyl)-4,5-dihydroimidazol-1-yl]propan-1-one Chemical compound CC(C)C(=O)N1C(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N=C1C1=CC=C(Cl)C=C1 FMOICKVRFIVFSJ-UHFFFAOYSA-N 0.000 claims 1
- PPUNIXZMUJDFGD-UHFFFAOYSA-N 3-[4,5-bis(4-chlorophenyl)-1-(2-methylpropanoyl)-4,5-dihydroimidazol-2-yl]-5-(methoxymethyl)benzoic acid Chemical compound COCC1=CC(C(O)=O)=CC(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)C(C)C)=C1 PPUNIXZMUJDFGD-UHFFFAOYSA-N 0.000 claims 1
- ZURPLQIDQHOEOM-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carboxylic acid Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(O)=O ZURPLQIDQHOEOM-UHFFFAOYSA-N 0.000 claims 1
- MOFYICNYPORLEK-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-n-(2-morpholin-4-ylethyl)-4,5-dihydroimidazole-1-carboxamide;hydrochloride Chemical compound Cl.CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NCCN1CCOCC1 MOFYICNYPORLEK-UHFFFAOYSA-N 0.000 claims 1
- JLIPANGOVCFWMA-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-n-[2-(dimethylamino)ethyl]-2-(2-ethoxy-4-methoxyphenyl)-4,5-dihydroimidazole-1-carboxamide Chemical class CCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NCCN(C)C JLIPANGOVCFWMA-UHFFFAOYSA-N 0.000 claims 1
- XASBVDPJXRXAIE-UHFFFAOYSA-N 4-[4,5-bis(4-bromophenyl)-2-(2-ethoxy-4-methoxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-2-one Chemical compound CCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Br)=CC=2)C(C=2C=CC(Br)=CC=2)N1C(=O)N1CC(=O)NCC1 XASBVDPJXRXAIE-UHFFFAOYSA-N 0.000 claims 1
- DWZCLLZNCHBXJE-UHFFFAOYSA-N 4-[4,5-bis(4-bromophenyl)-2-(2-ethoxy-4-methoxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazine-1-carbaldehyde Chemical compound CCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Br)=CC=2)C(C=2C=CC(Br)=CC=2)N1C(=O)N1CCN(C=O)CC1 DWZCLLZNCHBXJE-UHFFFAOYSA-N 0.000 claims 1
- MNDBVGIWGAGWLS-UHFFFAOYSA-N 4-[4,5-bis(4-bromophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-2-one Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Br)=CC=2)C(C=2C=CC(Br)=CC=2)N1C(=O)N1CC(=O)NCC1 MNDBVGIWGAGWLS-UHFFFAOYSA-N 0.000 claims 1
- DWSUDQAVAPLLLN-UHFFFAOYSA-N 4-[4,5-bis(4-bromophenyl)-2-[4-methoxy-2-(2,2,2-trifluoroethoxy)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-2-one Chemical compound FC(F)(F)COC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Br)=CC=2)C(C=2C=CC(Br)=CC=2)N1C(=O)N1CC(=O)NCC1 DWSUDQAVAPLLLN-UHFFFAOYSA-N 0.000 claims 1
- PWPDABWEHKHFFU-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-(2,4-diethoxyphenyl)-4,5-dihydroimidazole-1-carbonyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound CCOC1=CC(OCC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(=O)N(C)C)CC1 PWPDABWEHKHFFU-UHFFFAOYSA-N 0.000 claims 1
- OTEMIQJFRGXMLT-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-(2,4-diethoxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazine-1-carboxylic acid Chemical compound CCOC1=CC(OCC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCN(C(O)=O)CC1 OTEMIQJFRGXMLT-UHFFFAOYSA-N 0.000 claims 1
- SQBHMUWQZWKOAR-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-(2-ethoxy-4-methoxyphenyl)-4,5-dihydroimidazol-1-yl]piperazin-2-one Chemical compound CCOC1=C(C=CC(=C1)OC)C2=NC(C(N2N3CCNC(=O)C3)C4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl SQBHMUWQZWKOAR-UHFFFAOYSA-N 0.000 claims 1
- CMCSILRTJUOMGB-UHFFFAOYSA-N 4-[4,5-bis(4-chlorophenyl)-2-(4-ethoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-2-one Chemical compound CC(C)OC1=CC(OCC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CC(=O)NCC1 CMCSILRTJUOMGB-UHFFFAOYSA-N 0.000 claims 1
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- UWSWIDJMKXUGBJ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-(4-methyl-2-propan-2-ylphenyl)-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone Chemical compound CC1=CC(=C(C=C1)C2=NC(C(N2C(=O)N3CCNCC3)C4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl)C(C)C UWSWIDJMKXUGBJ-UHFFFAOYSA-N 0.000 claims 1
- AKTGWBSSJRWHRA-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-(5-ethoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazol-1-yl]-[4-(2-hydroxyethyl)piperazin-1-yl]methanone;hydrochloride Chemical compound Cl.CCOC1=CC=C(OC(C)C)C(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)N2CCN(CCO)CC2)=C1 AKTGWBSSJRWHRA-UHFFFAOYSA-N 0.000 claims 1
- HOZGIYCMSARBRJ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-(5-ethoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone Chemical compound CCOC1=CC=C(OC(C)C)C(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)N2CCNCC2)=C1 HOZGIYCMSARBRJ-UHFFFAOYSA-N 0.000 claims 1
- SFIXMZFYJSODBZ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-(5-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone Chemical compound COC1=CC=C(OC(C)C)C(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)N2CCNCC2)=C1 SFIXMZFYJSODBZ-UHFFFAOYSA-N 0.000 claims 1
- BAZOGFBMHDFPQV-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2,4-di(propan-2-yloxy)phenyl]-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone Chemical compound CC(C)OC1=CC(OC(C)C)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCNCC1 BAZOGFBMHDFPQV-UHFFFAOYSA-N 0.000 claims 1
- VDXRSWYRKORPPX-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2,5-di(propan-2-yloxy)phenyl]-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone;hydrochloride Chemical compound Cl.CC(C)OC1=CC=C(OC(C)C)C(C=2N(C(C(N=2)C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)C(=O)N2CCNCC2)=C1 VDXRSWYRKORPPX-UHFFFAOYSA-N 0.000 claims 1
- KILCMOMKEKCCTJ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-(2-fluoroethoxy)-4-methoxyphenyl]-4,5-dihydroimidazol-1-yl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone;hydrochloride Chemical compound Cl.FCCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(N2CCCC2)CC1 KILCMOMKEKCCTJ-UHFFFAOYSA-N 0.000 claims 1
- NHWRVSGFPNJWGS-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-(2-imidazol-1-ylethoxy)-4-methoxyphenyl]-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone Chemical compound C1=CN=CN1CCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCNCC1 NHWRVSGFPNJWGS-UHFFFAOYSA-N 0.000 claims 1
- DKRGIRUBVHOIDA-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-[2-(dimethylamino)ethoxy]-4-methoxyphenyl]-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone Chemical compound CN(C)CCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCNCC1 DKRGIRUBVHOIDA-UHFFFAOYSA-N 0.000 claims 1
- DVYHGBWJLLQBBU-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[4-(dimethylamino)-2-ethoxyphenyl]-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone Chemical compound CCOC1=CC(N(C)C)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCNCC1 DVYHGBWJLLQBBU-UHFFFAOYSA-N 0.000 claims 1
- SPMWPUNSIVBQNC-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[4-methoxy-2-(2-methoxyethoxy)phenyl]-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone Chemical compound COCCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCNCC1 SPMWPUNSIVBQNC-UHFFFAOYSA-N 0.000 claims 1
- JWKPQFRUXCPVPK-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[4-methoxy-2-(2-methylpropoxy)phenyl]-4,5-dihydroimidazol-1-yl]-piperazin-1-ylmethanone;hydrochloride Chemical compound Cl.CC(C)COC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCNCC1 JWKPQFRUXCPVPK-UHFFFAOYSA-N 0.000 claims 1
- VVECYSDOSOLUMK-UHFFFAOYSA-N [4,5-bis(4-ethynylphenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazol-1-yl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C#C)C(C=2C=CC(=CC=2)C#C)N1C(=O)N1CCC(N2CCCC2)CC1 VVECYSDOSOLUMK-UHFFFAOYSA-N 0.000 claims 1
- FNOTTWTWTBKWBL-UHFFFAOYSA-N [4-(aminomethyl)piperidin-1-yl]-[4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazol-1-yl]methanone Chemical compound CC(C)OC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)N1CCC(CN)CC1 FNOTTWTWTBKWBL-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
- QBNWWEJEFAZMOM-UHFFFAOYSA-N ethyl 2-[4-[4,5-bis(4-chlorophenyl)-1-(2-methylpropanoyl)-4,5-dihydroimidazol-2-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)C(C)C QBNWWEJEFAZMOM-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006005 fluoroethoxy group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UAGBUOPEUGMWLB-UHFFFAOYSA-N n-(2-aminoethyl)-4,5-bis(4-chlorophenyl)-2-(2-ethoxy-4-methoxyphenyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CCOC1=CC(OC)=CC=C1C1=NC(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)N1C(=O)NCCN UAGBUOPEUGMWLB-UHFFFAOYSA-N 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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| PCT/EP2002/013904 WO2003051359A1 (en) | 2001-12-18 | 2002-12-09 | Cis-2,4,5- triphenyl-imidazolines and their use in the treatment of tumors |
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| WO2019218904A1 (zh) * | 2018-05-18 | 2019-11-21 | 四川科伦博泰生物医药股份有限公司 | 非天然氨基酸类衍生物、其制备方法及用途 |
| CN112912143A (zh) | 2018-10-08 | 2021-06-04 | 美国密歇根州立大学试剂中心 | 小分子mdm2蛋白降解剂 |
| KR20230005160A (ko) | 2020-03-19 | 2023-01-09 | 카이메라 쎄라퓨틱스 인코포레이티드 | Mdm2 분해제 및 이의 용도 |
| WO2023056069A1 (en) | 2021-09-30 | 2023-04-06 | Angiex, Inc. | Degrader-antibody conjugates and methods of using same |
| WO2023191513A1 (ko) * | 2022-03-29 | 2023-10-05 | 주식회사 퓨전바이오텍 | 당 결합된 이미다졸린 유도체 및 이의 용도 |
| WO2024240858A1 (en) | 2023-05-23 | 2024-11-28 | Valerio Therapeutics | Protac molecules directed against dna damage repair system and uses thereof |
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| US11981640B1 (en) | 2023-11-08 | 2024-05-14 | King Faisal University | 4,5-bis(4-chlorophenyl)-1-hexyl-2-(3-hydroxy-4-methoxyphenyl)-1H-imidazole as an antimicrobial compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL158178B (nl) * | 1974-07-12 | 1978-10-16 | Philips Nv | Werkwijze ter bereiding van insekticide preparaten die een pyrazolinederivaat bevatten, aldus verkregen gevormde preparaten, en werkwijze ter bereiding van pyrazolinederivaten met insekticide werking. |
| US5182268A (en) * | 1989-11-22 | 1993-01-26 | Marion Merrell Dow, Inc. | Pharmaceutical composition comprising daunorubicin potentiated with 2,4,5-tri (4-methoxyphenyl)-4,5-dihydroimidazole |
| US5474998A (en) | 1990-08-17 | 1995-12-12 | E. I. Du Pont De Nemours And Company | Arthropodicidal pyrazolines, pyrazolidines and hydrazines |
| DE19831987A1 (de) | 1998-07-16 | 2000-01-20 | Bayer Ag | Diphenylimidazoline |
| AU1199600A (en) | 1998-10-02 | 2000-04-26 | Board Of Trustees Of The University Of Illinois, The | Estrogen receptor ligands |
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2002
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