RU2006100730A - CIS-2, 4, 5-TRIARIL-IMIDAZOLES - Google Patents
CIS-2, 4, 5-TRIARIL-IMIDAZOLES Download PDFInfo
- Publication number
- RU2006100730A RU2006100730A RU2006100730/04A RU2006100730A RU2006100730A RU 2006100730 A RU2006100730 A RU 2006100730A RU 2006100730/04 A RU2006100730/04 A RU 2006100730/04A RU 2006100730 A RU2006100730 A RU 2006100730A RU 2006100730 A RU2006100730 A RU 2006100730A
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- trifluoromethyl
- bis
- dihydro
- chloro
- Prior art date
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- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 219
- 125000003545 alkoxy group Chemical group 0.000 claims 95
- 125000000623 heterocyclic group Chemical group 0.000 claims 88
- -1 substituted R 7 Chemical group 0.000 claims 88
- 125000001424 substituent group Chemical group 0.000 claims 64
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 61
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 60
- 150000001875 compounds Chemical class 0.000 claims 54
- 125000004043 oxo group Chemical group O=* 0.000 claims 49
- 125000001072 heteroaryl group Chemical group 0.000 claims 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 36
- 125000003118 aryl group Chemical group 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 12
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 7
- 125000002636 imidazolinyl group Chemical group 0.000 claims 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 150000004885 piperazines Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- IHLVPMGYVXHKLT-UHFFFAOYSA-N (4-aminopiperidin-1-yl)-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-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(N)CC1 IHLVPMGYVXHKLT-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 claims 2
- 125000005394 methallyl group Chemical group 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims 1
- 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
- GKOOQGZRWFECQN-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-carboxylic acid Chemical compound ClC1=CC=C(C=C1)C1N=C(N(C1C1=CC=C(C=C1)Cl)C(=O)N1CCN(CC1)C(CN1CC(CCC1)C(=O)O)=O)C1=C(C=C(C=C1)C(F)(F)F)OCC GKOOQGZRWFECQN-UHFFFAOYSA-N 0.000 claims 1
- MQFQJFNNVLKWIY-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-carboxylic acid Chemical compound ClC1=CC=C(C=C1)C1N=C(N(C1C1=CC=C(C=C1)Cl)C(=O)N1CCN(CC1)C(CN1CCC(CC1)C(=O)O)=O)C1=C(C=C(C=C1)C(F)(F)F)OCC MQFQJFNNVLKWIY-UHFFFAOYSA-N 0.000 claims 1
- AXJVUVMTTQXGCS-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-carboxylic acid Chemical compound ClC1=CC=C(C=C1)C1N=C(N(C1C1=CC=C(C=C1)Cl)C(=O)N1CCN(CC1)CC(=O)N1CC(CCC1)C(=O)O)C1=C(C=C(C=C1)C(F)(F)F)OCC AXJVUVMTTQXGCS-UHFFFAOYSA-N 0.000 claims 1
- SNOADVUMXDNNJH-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-carboxylic acid N-ethylethanamine Chemical compound CCNCC.CCOC(C=C(C(F)(F)F)C=C1)=C1C(N(C1C(C=C2)=CC=C2Cl)C(N2CCN(CC(N(CCC3)CC3C(O)=O)=O)CC2)=O)=NC1C(C=C1)=CC=C1Cl SNOADVUMXDNNJH-UHFFFAOYSA-N 0.000 claims 1
- DEWCFIYTKBRZDI-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-carboxylic acid Chemical compound ClC1=CC=C(C=C1)C1N=C(N(C1C1=CC=C(C=C1)Cl)C(=O)N1CCC(CC1)NC(=O)CN1CC(CCC1)C(=O)O)C1=C(C=C(C=C1)C(F)(F)F)OCC DEWCFIYTKBRZDI-UHFFFAOYSA-N 0.000 claims 1
- AYNOHPNGKRJXTL-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-carboxylic acid Chemical compound ClC1=CC=C(C=C1)C1N=C(N(C1C1=CC=C(C=C1)Cl)C(=O)N1CCC(CC1)NC(=O)CN1CCC(CC1)C(=O)O)C1=C(C=C(C=C1)C(F)(F)F)OCC AYNOHPNGKRJXTL-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
- 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 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
- 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 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
- 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 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
- QDGJAAOFBIEXOC-UHFFFAOYSA-N 1-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-2-thiophen-2-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(C(=O)CC=2SC=CC=2)CC1 QDGJAAOFBIEXOC-UHFFFAOYSA-N 0.000 claims 1
- JVRHHKSACMBALZ-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-carboxylic acid Chemical compound ClC1=CC=C(C=C1)C1N=C(N(C1C1=CC=C(C=C1)Cl)C(=O)N1CCN(CC1)C(=O)N1CCC(CC1)C(=O)O)C1=C(C=C(C=C1)C(F)(F)F)OCC JVRHHKSACMBALZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZSHRJBMPUVRXKC-UHFFFAOYSA-N 1-[4-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazine-1-carbonyl]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)C2CCN(CC2)C(C)=O)CC1 ZSHRJBMPUVRXKC-UHFFFAOYSA-N 0.000 claims 1
- NXMXETCTWNXSFG-UHFFFAOYSA-N 1-methoxypropan-2-amine Chemical compound COCC(C)N NXMXETCTWNXSFG-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
- 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 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
- 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 1
- 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 1
- 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 1
- WEDUREKGKXARTL-UHFFFAOYSA-N 2-[4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-1-morpholin-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)N2CCOCC2)CC1 WEDUREKGKXARTL-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
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- 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 1
- 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 1
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- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- 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 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
- 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
- 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 1
- AZFCHKRYFQIJDY-UHFFFAOYSA-N 2-amino-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)CN)CC1 AZFCHKRYFQIJDY-UHFFFAOYSA-N 0.000 claims 1
- OUPBWFCDNYIFCF-UHFFFAOYSA-N 2-aminoethanol 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carboxylic acid Chemical compound CCOC(C=C(C(F)(F)F)C=C1)=C1C(N(C1C(C=C2)=CC=C2Cl)C(O)=O)=NC1C(C=C1)=CC=C1Cl.NCCO OUPBWFCDNYIFCF-UHFFFAOYSA-N 0.000 claims 1
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 claims 1
- UNIJBMUBHBAUET-UHFFFAOYSA-N 3-(methylamino)propanenitrile Chemical compound CNCCC#N UNIJBMUBHBAUET-UHFFFAOYSA-N 0.000 claims 1
- KZGMKPKDEDWOIT-UHFFFAOYSA-N 3-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-1,1-dimethylurea 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)N(C)C)CC1 KZGMKPKDEDWOIT-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
- ABZGTIUIMHXVIS-UHFFFAOYSA-N 3-oxopiperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNC(=O)C1 ABZGTIUIMHXVIS-UHFFFAOYSA-N 0.000 claims 1
- BOQXMGLSCWGFFY-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carboxylic acid 1-(furan-2-yl)-N-methylmethanamine Chemical compound CCOC(C=C(C(F)(F)F)C=C1)=C1C(N(C1C(C=C2)=CC=C2Cl)C(O)=O)=NC1C(C=C1)=CC=C1Cl.CNCC1=CC=CO1 BOQXMGLSCWGFFY-UHFFFAOYSA-N 0.000 claims 1
- OJVYNBFFEMPAGF-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carboxylic acid 2,5-dimethoxyaniline Chemical class CCOC(C=C(C(F)(F)F)C=C1)=C1C(N(C1C(C=C2)=CC=C2Cl)C(O)=O)=NC1C(C=C1)=CC=C1Cl.COC(C=C1)=CC(N)=C1OC OJVYNBFFEMPAGF-UHFFFAOYSA-N 0.000 claims 1
- PNGTXCVQHIWTPO-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carboxylic acid 2-(methylamino)acetonitrile Chemical compound CCOC(C=C(C(F)(F)F)C=C1)=C1C(N(C1C(C=C2)=CC=C2Cl)C(O)=O)=NC1C(C=C1)=CC=C1Cl.CNCC#N PNGTXCVQHIWTPO-UHFFFAOYSA-N 0.000 claims 1
- LDTPKBJARBOUAO-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carboxylic acid 2-(methylamino)ethanol Chemical class CCOC(C=C(C(F)(F)F)C=C1)=C1C(N(C1C(C=C2)=CC=C2Cl)C(O)=O)=NC1C(C=C1)=CC=C1Cl.CNCCO LDTPKBJARBOUAO-UHFFFAOYSA-N 0.000 claims 1
- QPNUUSJOQVONAH-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carboxylic acid 2-methoxy-N-(2-methoxyethyl)ethanamine Chemical class CCOC(C=C(C(F)(F)F)C=C1)=C1C(N(C1C(C=C2)=CC=C2Cl)C(O)=O)=NC1C(C=C1)=CC=C1Cl.COCCNCCOC QPNUUSJOQVONAH-UHFFFAOYSA-N 0.000 claims 1
- OMCYTVXQWCFALO-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-N-(methoxymethyl)-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)NCOC OMCYTVXQWCFALO-UHFFFAOYSA-N 0.000 claims 1
- OVYZOSNOYGXIRL-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-[(4-sulfamoylphenyl)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)NCC1=CC=C(S(N)(=O)=O)C=C1 OVYZOSNOYGXIRL-UHFFFAOYSA-N 0.000 claims 1
- NJQKQSHAGFJUHN-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-n-methoxy-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)NOC NJQKQSHAGFJUHN-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
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- BCRXVTIICGAQSG-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-(4-thiophen-3-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)C2=CSC=C2)CC1 BCRXVTIICGAQSG-UHFFFAOYSA-N 0.000 claims 1
- AFNFFRKSDJQCIJ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(1,2-dimethylimidazol-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)C=2N=C(C)N(C)C=2)CC1 AFNFFRKSDJQCIJ-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
- OPYWECJIKLJLGC-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(2-ethoxyethyl)piperazin-1-yl]methanone Chemical compound C1CN(CCOCC)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 OPYWECJIKLJLGC-UHFFFAOYSA-N 0.000 claims 1
- MKWZOCOMXIXIHZ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(2-methoxyethyl)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(CCOC)CC1 MKWZOCOMXIXIHZ-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
- ZBIZRPTWKDPGON-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(3,5-dimethoxyphenyl)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(C=2C=C(OC)C=C(OC)C=2)CC1 ZBIZRPTWKDPGON-UHFFFAOYSA-N 0.000 claims 1
- XRYPQDXFWZERNP-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(3-hydroxypiperidin-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)N2CC(O)CCC2)CC1 XRYPQDXFWZERNP-UHFFFAOYSA-N 0.000 claims 1
- YRLQJUVSNRSRMP-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-(3-methoxypropyl)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(CCCOC)CC1 YRLQJUVSNRSRMP-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
- 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 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
- 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 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
- 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 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
- 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 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
- 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 1
- NJROZHSIDXNWOA-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[3-(diethylamino)propyl]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(CCCN(CC)CC)CC1 NJROZHSIDXNWOA-UHFFFAOYSA-N 0.000 claims 1
- QRNSLQCDKUKGGQ-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[3-(dimethylamino)propyl]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(CCCN(C)C)CC1 QRNSLQCDKUKGGQ-UHFFFAOYSA-N 0.000 claims 1
- JYJHDPXRHVGMTC-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[3-(dipropylamino)propyl]piperazin-1-yl]methanone Chemical compound C1CN(CCCN(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 JYJHDPXRHVGMTC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BPPOPIKNOBHFLF-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[5-(trifluoromethyl)pyridin-2-yl]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(C=2N=CC(=CC=2)C(F)(F)F)CC1 BPPOPIKNOBHFLF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- YWCVPNHASCELHD-UHFFFAOYSA-N [4,5-bis(4-chlorophenyl)-2-[2-propan-2-yloxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]-[4-[(4-pyrrolidin-1-ylpiperidin-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=C1CN1CCC(N2CCCC2)CC1 YWCVPNHASCELHD-UHFFFAOYSA-N 0.000 claims 1
- VTSSJUIGCYCGKA-UHFFFAOYSA-N [4-[(4-aminopiperidin-1-yl)methyl]phenyl]-[4,5-bis(4-chlorophenyl)-2-[2-propan-2-yloxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazol-1-yl]methanone Chemical compound 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(N)CC1 VTSSJUIGCYCGKA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GRTRICISKIPFQP-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-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)C2OC3=CC=CC=C3OC2)CC1 GRTRICISKIPFQP-UHFFFAOYSA-N 0.000 claims 1
- RTXIAHIHLNKSAI-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-(2,5-dichlorothiophen-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=C(SC(Cl)=C2)Cl)CC1 RTXIAHIHLNKSAI-UHFFFAOYSA-N 0.000 claims 1
- ITADBKAAYQFMBH-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-(2,5-dimethylfuran-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=C(OC(C)=C2)C)CC1 ITADBKAAYQFMBH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- OIOXXEAFLDNPPJ-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-(furan-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)C=2OC=CC=2)CC1 OIOXXEAFLDNPPJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- MBWSRQPGPPWUGB-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-pyridin-4-ylmethanone 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=2C=CN=CC=2)CC1 MBWSRQPGPPWUGB-UHFFFAOYSA-N 0.000 claims 1
- KEQQOWBTQSHSKX-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-thiophen-2-ylmethanone 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=2SC=CC=2)CC1 KEQQOWBTQSHSKX-UHFFFAOYSA-N 0.000 claims 1
- DLJSPKRDWBJMDG-UHFFFAOYSA-N [4-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperazin-1-yl]-thiophen-3-ylmethanone 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=CSC=C2)CC1 DLJSPKRDWBJMDG-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HZTMLJLCAPPFDV-UHFFFAOYSA-N n-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-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)CN2CCC3(CC2)OCCO3)CC1 HZTMLJLCAPPFDV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- HQZBIQHTOHZTPE-UHFFFAOYSA-N n-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-2-(dimethylamino)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)CN(C)C)CC1 HQZBIQHTOHZTPE-UHFFFAOYSA-N 0.000 claims 1
- SWDYPEDVVHRLMH-UHFFFAOYSA-N n-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-2-(methylamino)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)CNC)CC1 SWDYPEDVVHRLMH-UHFFFAOYSA-N 0.000 claims 1
- YKJLSOQWRNRPFT-UHFFFAOYSA-N n-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-2-[1,3-dioxolan-2-ylmethyl(methyl)amino]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)CN(C)CC2OCCO2)CC1 YKJLSOQWRNRPFT-UHFFFAOYSA-N 0.000 claims 1
- NXMIYADOTCPWNS-UHFFFAOYSA-N n-[1-[4,5-bis(4-chlorophenyl)-2-[2-ethoxy-4-(trifluoromethyl)phenyl]-4,5-dihydroimidazole-1-carbonyl]piperidin-4-yl]-2-[4-(hydroxymethyl)piperidin-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)CN2CCC(CO)CC2)CC1 NXMIYADOTCPWNS-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- IIKFXOLJMNWWCH-UHFFFAOYSA-N piperidine-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCN(C(O)=O)CC1 IIKFXOLJMNWWCH-UHFFFAOYSA-N 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- 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
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
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- 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
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- Bioinformatics & Cheminformatics (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Claims (51)
Applications Claiming Priority (2)
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| US47935103P | 2003-06-17 | 2003-06-17 | |
| US60/479,351 | 2003-06-17 |
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| RU2006100730A true RU2006100730A (en) | 2006-08-10 |
| RU2319696C2 RU2319696C2 (en) | 2008-03-20 |
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| EP (1) | EP1638942A1 (en) |
| JP (1) | JP2006527712A (en) |
| KR (1) | KR100768021B1 (en) |
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| AR (1) | AR044703A1 (en) |
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| CL (1) | CL2004001484A1 (en) |
| MX (1) | MXPA05013279A (en) |
| RU (1) | RU2319696C2 (en) |
| TW (1) | TW200510387A (en) |
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| US7579368B2 (en) * | 2005-03-16 | 2009-08-25 | Hoffman-La Roche Inc. | Cis-imidazolines |
| ES2538714T3 (en) * | 2005-12-01 | 2015-06-23 | F. Hoffmann-La Roche Ag | 2,4,5-Triphenyl-imidazoline derivatives as inhibitors of the interaction between p53 and MDM2 proteins for use as anti-cancer agents |
| US8114095B2 (en) * | 2006-11-10 | 2012-02-14 | Bausch & Lomb Incorporated | Intraocular lens injection apparatus and method |
| MX2009006397A (en) | 2006-12-14 | 2009-08-13 | Daiichi Sankyo Co Ltd | Imidazothiazole derivatives. |
| US7625895B2 (en) * | 2007-04-12 | 2009-12-01 | Hoffmann-Le Roche Inc. | Diphenyl-dihydro-imidazopyridinones |
| EP2298778A4 (en) | 2008-06-12 | 2011-10-05 | Daiichi Sankyo Co Ltd | IMIDAZOTHIAZOLE DERIVATE HAVING A CYCLIC STRUCTURE OF 4,7-DIAZASPIRO®2.5OCITANE |
| CN102356085A (en) | 2009-01-16 | 2012-02-15 | 第一三共株式会社 | Imidazothiazole derivative having proline ring structure |
| IT1396520B1 (en) | 2009-12-10 | 2012-12-14 | Nuovo Pignone Spa | COUPLING FOR ROTOR BALANCING |
| 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 |
| JP2019522633A (en) | 2016-05-20 | 2019-08-15 | ジェネンテック, インコーポレイテッド | 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 |
| WO2024240858A1 (en) | 2023-05-23 | 2024-11-28 | Valerio Therapeutics | Protac molecules directed against dna damage repair system and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2030158A1 (en) * | 1989-11-22 | 1991-05-23 | Nahed K. Ahmed | Cancer treatments |
| GB9127050D0 (en) * | 1991-12-20 | 1992-02-19 | Orion Yhtymae Oy | Substituted imidazole derivatives and their preparation and use |
| DE10043456A1 (en) * | 2000-09-04 | 2002-03-14 | Merck Patent Gmbh | Use of ectoin or ectoin derivatives to stabilize p53 |
| RU2305095C2 (en) * | 2001-12-18 | 2007-08-27 | Ф.Хоффманн-Ля Рош Аг | Cis-2,4,5-triphenylimidazolines and pharmaceutical composition based on thereof |
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2004
- 2004-06-08 MX MXPA05013279A patent/MXPA05013279A/en unknown
- 2004-06-08 RU RU2006100730/04A patent/RU2319696C2/en not_active IP Right Cessation
- 2004-06-08 CA CA002528119A patent/CA2528119A1/en not_active Abandoned
- 2004-06-08 JP JP2006515856A patent/JP2006527712A/en not_active Ceased
- 2004-06-08 WO PCT/EP2004/006176 patent/WO2005003097A1/en not_active Ceased
- 2004-06-08 KR KR1020057024295A patent/KR100768021B1/en not_active Expired - Fee Related
- 2004-06-08 BR BRPI0411841-3A patent/BRPI0411841A/en not_active IP Right Cessation
- 2004-06-08 AU AU2004254187A patent/AU2004254187A1/en not_active Abandoned
- 2004-06-08 CN CNB2004800170350A patent/CN100465163C/en not_active Expired - Fee Related
- 2004-06-08 EP EP04739704A patent/EP1638942A1/en not_active Withdrawn
- 2004-06-11 TW TW093116988A patent/TW200510387A/en unknown
- 2004-06-15 CL CL200401484A patent/CL2004001484A1/en unknown
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| CN100465163C (en) | 2009-03-04 |
| CA2528119A1 (en) | 2005-01-13 |
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| CN1809538A (en) | 2006-07-26 |
| KR20060021902A (en) | 2006-03-08 |
| RU2319696C2 (en) | 2008-03-20 |
| WO2005003097A1 (en) | 2005-01-13 |
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| MXPA05013279A (en) | 2006-03-09 |
| JP2006527712A (en) | 2006-12-07 |
| CL2004001484A1 (en) | 2005-05-27 |
| TW200510387A (en) | 2005-03-16 |
| EP1638942A1 (en) | 2006-03-29 |
| BRPI0411841A (en) | 2006-08-08 |
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