CA2633918A1 - Substituted imidazoline derivatives - Google Patents

Info

Publication number

CA2633918A1

CA2633918A1 CA002633918A CA2633918A CA2633918A1 CA 2633918 A1 CA2633918 A1 CA 2633918A1 CA 002633918 A CA002633918 A CA 002633918A CA 2633918 A CA2633918 A CA 2633918A CA 2633918 A1 CA2633918 A1 CA 2633918A1

Authority

CA

Canada

Prior art keywords

dihydro

imidazole

carboxylic acid

methyl ester

acid methyl

Prior art date

2005-12-22

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000002462 imidazolines Chemical class 0.000 title claims abstract description 48
• 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title claims abstract description 35
• 239000003814 drug Substances 0.000 claims abstract description 28
• 238000000034 method Methods 0.000 claims abstract description 12
• 239000000203 mixture Substances 0.000 claims description 67
• -1 4-Cl-benzyl Chemical group 0.000 claims description 48
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 150000001299 aldehydes Chemical class 0.000 claims description 33
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
• 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 description 26
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• 239000002253 acid Substances 0.000 claims description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• 208000002193 Pain Diseases 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 229920006395 saturated elastomer Polymers 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 13
• 238000003786 synthesis reaction Methods 0.000 claims description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 11
• 150000007513 acids Chemical class 0.000 claims description 11
• 150000005840 aryl radicals Chemical group 0.000 claims description 11
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 150000003254 radicals Chemical class 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 238000011282 treatment Methods 0.000 claims description 7
• 208000000094 Chronic Pain Diseases 0.000 claims description 6
• 239000013543 active substance Substances 0.000 claims description 6
• IWGVZQAPMJDBGE-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1CC1C(CCC)(C(=O)OC)N=CN1CC1=CC=CC=C1 IWGVZQAPMJDBGE-UHFFFAOYSA-N 0.000 claims description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 5
• 206010012735 Diarrhoea Diseases 0.000 claims description 4
• 208000003251 Pruritus Diseases 0.000 claims description 4
• 206010046543 Urinary incontinence Diseases 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 150000004702 methyl esters Chemical class 0.000 claims description 4
• 208000004296 neuralgia Diseases 0.000 claims description 4
• 230000002981 neuropathic effect Effects 0.000 claims description 4
• 208000021722 neuropathic pain Diseases 0.000 claims description 4
• 239000003960 organic solvent Substances 0.000 claims description 4
• MIHGGZOJCPTLTI-UHFFFAOYSA-N 2-[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]acetaldehyde Chemical compound C1CC(CC=O)CCC1C(N(C)C)CCC1=CC=CC=C1 MIHGGZOJCPTLTI-UHFFFAOYSA-N 0.000 claims description 3
• 208000019901 Anxiety disease Diseases 0.000 claims description 3
• DJAMXGJKOZCVJC-UHFFFAOYSA-N C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1CC1C(CCC(=O)OC)(C(=O)OC)N=CN1C(C)C1=CC=CC=C1 Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1CC1C(CCC(=O)OC)(C(=O)OC)N=CN1C(C)C1=CC=CC=C1 DJAMXGJKOZCVJC-UHFFFAOYSA-N 0.000 claims description 3
• HXJFSFOOAWTVQN-UHFFFAOYSA-N COC(=O)C1(N=CN(C1C1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CC1=CC=C(C=C1)Cl Chemical compound COC(=O)C1(N=CN(C1C1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CC1=CC=C(C=C1)Cl HXJFSFOOAWTVQN-UHFFFAOYSA-N 0.000 claims description 3
• UYSWIRADPTZPLN-UHFFFAOYSA-N COC(=O)C1(N=CN(C1C1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CCCC Chemical compound COC(=O)C1(N=CN(C1C1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CCCC UYSWIRADPTZPLN-UHFFFAOYSA-N 0.000 claims description 3
• GREDRVCBDLFPGT-UHFFFAOYSA-N COC(=O)C1(N=CN(C1C1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CSCC1=CC=CC=C1 Chemical compound COC(=O)C1(N=CN(C1C1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CSCC1=CC=CC=C1 GREDRVCBDLFPGT-UHFFFAOYSA-N 0.000 claims description 3
• MAUSLMGMYDVUQB-UHFFFAOYSA-N COC(=O)C1(N=CN(C1C1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CC1=CC=C(C=C1)Cl Chemical compound COC(=O)C1(N=CN(C1C1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CC1=CC=C(C=C1)Cl MAUSLMGMYDVUQB-UHFFFAOYSA-N 0.000 claims description 3
• OGOGQDWGOWDHPZ-UHFFFAOYSA-N COC(=O)C1(N=CN(C1C1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CCCC Chemical compound COC(=O)C1(N=CN(C1C1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CCCC OGOGQDWGOWDHPZ-UHFFFAOYSA-N 0.000 claims description 3
• KBDOWHOIOUBRKJ-UHFFFAOYSA-N COC(=O)C1(N=CN(C1C1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CSCC1=CC=CC=C1 Chemical compound COC(=O)C1(N=CN(C1C1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CSCC1=CC=CC=C1 KBDOWHOIOUBRKJ-UHFFFAOYSA-N 0.000 claims description 3
• WWGKSILMGXHCQJ-UHFFFAOYSA-N COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CSCC1=CC=CC=C1 Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CSCC1=CC=CC=C1 WWGKSILMGXHCQJ-UHFFFAOYSA-N 0.000 claims description 3
• PLAHKKIIOPOVNT-UHFFFAOYSA-N COC(=O)C1(N=CN(C1CC1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CCCC Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CCCC PLAHKKIIOPOVNT-UHFFFAOYSA-N 0.000 claims description 3
• 230000001154 acute effect Effects 0.000 claims description 3
• 208000005298 acute pain Diseases 0.000 claims description 3
• 239000000654 additive Substances 0.000 claims description 3
• 230000036506 anxiety Effects 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
• OIICSYADHRIQJO-UHFFFAOYSA-N methyl 3-benzyl-4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-5-(2-methylpropyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1C1C(C(=O)OC)(CC(C)C)N=CN1CC1=CC=CC=C1 OIICSYADHRIQJO-UHFFFAOYSA-N 0.000 claims description 3
• AJRAORCRKJFDRX-UHFFFAOYSA-N methyl 3-benzyl-4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-5-[(4-chlorophenyl)methyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(CC=2C=CC=CC=2)C(C2CCC(CC2)C(N(C)C)C=2C=CC(Cl)=CC=2)C1(C(=O)OC)CC1=CC=C(Cl)C=C1 AJRAORCRKJFDRX-UHFFFAOYSA-N 0.000 claims description 3
• UMVZSUJJCJKGKW-UHFFFAOYSA-N methyl 3-benzyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(2-methylpropyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1C1C(C(=O)OC)(CC(C)C)N=CN1CC1=CC=CC=C1 UMVZSUJJCJKGKW-UHFFFAOYSA-N 0.000 claims description 3
• VLXDQVDEQYTOED-UHFFFAOYSA-N methyl 3-benzyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1C1C(CCC(=O)OC)(C(=O)OC)N=CN1CC1=CC=CC=C1 VLXDQVDEQYTOED-UHFFFAOYSA-N 0.000 claims description 3
• SAKCACZLKYADOK-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(2-methylpropyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1CC1C(C(=O)OC)(CC(C)C)N=CN1CC1=CC=CC=C1 SAKCACZLKYADOK-UHFFFAOYSA-N 0.000 claims description 3
• VTWRORWDADHKFE-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1CC1C(CCC(=O)OC)(C(=O)OC)N=CN1CC1=CC=CC=C1 VTWRORWDADHKFE-UHFFFAOYSA-N 0.000 claims description 3
• SWKNNMIWXDGVQV-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1CC1C(C(=O)OC)(CSC)N=CN1CC1=CC=CC=C1 SWKNNMIWXDGVQV-UHFFFAOYSA-N 0.000 claims description 3
• LJRRTUZRLNYNNV-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-[(4-chlorophenyl)methyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(CC=2C=CC=CC=2)C(CC2CCC(CC2)C(N(C)C)C=2C=CC(Cl)=CC=2)C1(C(=O)OC)CC1=CC=C(Cl)C=C1 LJRRTUZRLNYNNV-UHFFFAOYSA-N 0.000 claims description 3
• XCBPYRVYYVUORS-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1CC1C(C(=O)OC)(CCSC)N=CN1CC1=CC=CC=C1 XCBPYRVYYVUORS-UHFFFAOYSA-N 0.000 claims description 3
• KUOAGWCKWOCREZ-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1CC1C(CCC(=O)OC)(C(=O)OC)N=CN1CC1=CC=CC=C1 KUOAGWCKWOCREZ-UHFFFAOYSA-N 0.000 claims description 3
• KUOAMXRUFSIQIQ-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-methyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1CC1C(C(=O)OC)(C)N=CN1CC1=CC=CC=C1 KUOAMXRUFSIQIQ-UHFFFAOYSA-N 0.000 claims description 3
• SVTONLHXVSCFEC-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(F)=CC=2)CCC1CC1C(C(=O)OC)(CCSC)N=CN1CC1=CC=CC=C1 SVTONLHXVSCFEC-UHFFFAOYSA-N 0.000 claims description 3
• UFTNGKKYXRIDBG-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-methyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(F)=CC=2)CCC1CC1C(C(=O)OC)(C)N=CN1CC1=CC=CC=C1 UFTNGKKYXRIDBG-UHFFFAOYSA-N 0.000 claims description 3
• WARRDGNMHZRTQP-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(F)=CC=2)CCC1CC1C(CCC)(C(=O)OC)N=CN1CC1=CC=CC=C1 WARRDGNMHZRTQP-UHFFFAOYSA-N 0.000 claims description 3
• WRSJNNDEPMLFEJ-UHFFFAOYSA-N methyl 3-benzyl-5-(benzylsulfanylmethyl)-4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(CC=2C=CC=CC=2)C(C2CCC(CC2)C(N(C)C)C=2C=CC(Cl)=CC=2)C1(C(=O)OC)CSCC1=CC=CC=C1 WRSJNNDEPMLFEJ-UHFFFAOYSA-N 0.000 claims description 3
• SOPYTKCRBDRUQB-UHFFFAOYSA-N methyl 3-benzyl-5-(benzylsulfanylmethyl)-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(CC=2C=CC=CC=2)C(C2CCC(CC2)C(N(C)C)C=2C=C(F)C=CC=2)C1(C(=O)OC)CSCC1=CC=CC=C1 SOPYTKCRBDRUQB-UHFFFAOYSA-N 0.000 claims description 3
• UGSDRXNLIQGMCN-UHFFFAOYSA-N methyl 3-benzyl-5-(benzylsulfanylmethyl)-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(CC=2C=CC=CC=2)C(CC2CCC(CC2)C(N(C)C)C=2C=CC(Cl)=CC=2)C1(C(=O)OC)CSCC1=CC=CC=C1 UGSDRXNLIQGMCN-UHFFFAOYSA-N 0.000 claims description 3
• MPNCLXBLPSQJMJ-UHFFFAOYSA-N methyl 3-benzyl-5-(benzylsulfanylmethyl)-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(CC=2C=CC=CC=2)C(CC2CCC(CC2)C(N(C)C)C=2C=C(F)C=CC=2)C1(C(=O)OC)CSCC1=CC=CC=C1 MPNCLXBLPSQJMJ-UHFFFAOYSA-N 0.000 claims description 3
• QTPBGYPVWOIAFP-UHFFFAOYSA-N methyl 3-benzyl-5-[(4-chlorophenyl)methyl]-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(CC=2C=CC=CC=2)C(C2CCC(CC2)C(N(C)C)C=2C=C(F)C=CC=2)C1(C(=O)OC)CC1=CC=C(Cl)C=C1 QTPBGYPVWOIAFP-UHFFFAOYSA-N 0.000 claims description 3
• VNVIXYWKQXGNFQ-UHFFFAOYSA-N methyl 3-butyl-4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1C1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 VNVIXYWKQXGNFQ-UHFFFAOYSA-N 0.000 claims description 3
• WLDLICZFVWOUTE-UHFFFAOYSA-N methyl 3-butyl-4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-5-[(4-chlorophenyl)methyl]-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1C1N(CCCC)C=NC1(C(=O)OC)CC1=CC=C(Cl)C=C1 WLDLICZFVWOUTE-UHFFFAOYSA-N 0.000 claims description 3
• REZARQLAHUEAOG-UHFFFAOYSA-N methyl 3-butyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(2-methylpropyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CC(C)C)(C(=O)OC)C1C1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 REZARQLAHUEAOG-UHFFFAOYSA-N 0.000 claims description 3
• JNASVVSNXIRSGH-UHFFFAOYSA-N methyl 3-butyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(methylsulfanylmethyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CSC)(C(=O)OC)C1C1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 JNASVVSNXIRSGH-UHFFFAOYSA-N 0.000 claims description 3
• AJADKPRMVOXCKO-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 AJADKPRMVOXCKO-UHFFFAOYSA-N 0.000 claims description 3
• UKRNLSDIOFQGQP-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 UKRNLSDIOFQGQP-UHFFFAOYSA-N 0.000 claims description 3
• VTCOBRHXWIBSFZ-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-[(4-chlorophenyl)methyl]-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1CC1N(CCCC)C=NC1(C(=O)OC)CC1=CC=C(Cl)C=C1 VTCOBRHXWIBSFZ-UHFFFAOYSA-N 0.000 claims description 3
• HHCOWMRXOBBYEI-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 HHCOWMRXOBBYEI-UHFFFAOYSA-N 0.000 claims description 3
• SCJYTXWDTANZHP-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(F)=CC=2)CC1 SCJYTXWDTANZHP-UHFFFAOYSA-N 0.000 claims description 3
• QPYFAEQAZRVDIK-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(F)=CC=2)CC1 QPYFAEQAZRVDIK-UHFFFAOYSA-N 0.000 claims description 3
• NIWDBFQCBIRAAY-UHFFFAOYSA-N methyl 3-butyl-5-[(4-chlorophenyl)methyl]-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1C1N(CCCC)C=NC1(C(=O)OC)CC1=CC=C(Cl)C=C1 NIWDBFQCBIRAAY-UHFFFAOYSA-N 0.000 claims description 3
• QFEYWLJWQHGTAH-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(2-methylpropyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(CC(C)C)N=CN(C2CCCCC2)C1C(CC1)CCC1C(N(C)C)C1=CC=CC(F)=C1 QFEYWLJWQHGTAH-UHFFFAOYSA-N 0.000 claims description 3
• XKUMVTDDJYRYRX-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)CCC1(C(=O)OC)N=CN(C2CCCCC2)C1C(CC1)CCC1C(N(C)C)C1=CC=CC(F)=C1 XKUMVTDDJYRYRX-UHFFFAOYSA-N 0.000 claims description 3
• AYGNULSLFTYDIP-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-methyl-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(C)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)CCC1=CC=CC=C1 AYGNULSLFTYDIP-UHFFFAOYSA-N 0.000 claims description 3
• WNWWSUOCXNXRAQ-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-propyl-4h-imidazole-5-carboxylate Chemical compound CCCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)CCC1=CC=CC=C1 WNWWSUOCXNXRAQ-UHFFFAOYSA-N 0.000 claims description 3
• XGSYPCLYMGCBFG-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-4h-imidazole-5-carboxylate Chemical compound CSCCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=CC(F)=C1 XGSYPCLYMGCBFG-UHFFFAOYSA-N 0.000 claims description 3
• YNBNWAIGBFERQF-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-methyl-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(C)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=CC(F)=C1 YNBNWAIGBFERQF-UHFFFAOYSA-N 0.000 claims description 3
• IBSXYVMWVYBDAS-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-propyl-4h-imidazole-5-carboxylate Chemical compound CCCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=CC(F)=C1 IBSXYVMWVYBDAS-UHFFFAOYSA-N 0.000 claims description 3
• RTXHASOGARYSJN-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-4h-imidazole-5-carboxylate Chemical compound CSCCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(F)C=C1 RTXHASOGARYSJN-UHFFFAOYSA-N 0.000 claims description 3
• SOMPOOCLHYJBGV-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-methyl-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(C)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(F)C=C1 SOMPOOCLHYJBGV-UHFFFAOYSA-N 0.000 claims description 3
• ZVRLAGYLHFCASN-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-propyl-4h-imidazole-5-carboxylate Chemical compound CCCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(F)C=C1 ZVRLAGYLHFCASN-UHFFFAOYSA-N 0.000 claims description 3
• FOWMRXMAENPXIX-UHFFFAOYSA-N methyl 4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-3-cyclohexyl-5-(2-methylpropyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(CC(C)C)N=CN(C2CCCCC2)C1C(CC1)CCC1C(N(C)C)C1=CC=C(Cl)C=C1 FOWMRXMAENPXIX-UHFFFAOYSA-N 0.000 claims description 3
• UQPUMJIREWXFSH-UHFFFAOYSA-N methyl 4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-3-cyclohexyl-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)CCC1(C(=O)OC)N=CN(C2CCCCC2)C1C(CC1)CCC1C(N(C)C)C1=CC=C(Cl)C=C1 UQPUMJIREWXFSH-UHFFFAOYSA-N 0.000 claims description 3
• GCDPODRUDPUGEY-UHFFFAOYSA-N methyl 4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-5-(2-methylpropyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1C1C(C(=O)OC)(CC(C)C)N=CN1C(C)C1=CC=CC=C1 GCDPODRUDPUGEY-UHFFFAOYSA-N 0.000 claims description 3
• CMRAJPYCLCBWRR-UHFFFAOYSA-N methyl 4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-5-(3-methoxy-3-oxopropyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1C1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 CMRAJPYCLCBWRR-UHFFFAOYSA-N 0.000 claims description 3
• HLYFOJRRGFMHKA-UHFFFAOYSA-N methyl 4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(2-methylpropyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CC(C)C)(C(=O)OC)C1C1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 HLYFOJRRGFMHKA-UHFFFAOYSA-N 0.000 claims description 3
• VCQIDKQWKIGUPE-UHFFFAOYSA-N methyl 4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(3-methoxy-3-oxopropyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1C1C(CCC(=O)OC)(C(=O)OC)N=CN1C(C)C1=CC=CC=C1 VCQIDKQWKIGUPE-UHFFFAOYSA-N 0.000 claims description 3
• LXKMRYDOALSBQK-UHFFFAOYSA-N methyl 4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(methylsulfanylmethyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CSC)(C(=O)OC)C1C1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 LXKMRYDOALSBQK-UHFFFAOYSA-N 0.000 claims description 3
• UOCLNASTGKMBGT-UHFFFAOYSA-N methyl 4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-3-cyclohexyl-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)CCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(Cl)C=C1 UOCLNASTGKMBGT-UHFFFAOYSA-N 0.000 claims description 3
• SZRFJRYDBNOOBN-UHFFFAOYSA-N methyl 4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-3-cyclohexyl-5-(methylsulfanylmethyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(CSC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(Cl)C=C1 SZRFJRYDBNOOBN-UHFFFAOYSA-N 0.000 claims description 3
• VBERTXPENGLIEG-UHFFFAOYSA-N methyl 4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(2-methylpropyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1CC1C(C(=O)OC)(CC(C)C)N=CN1C(C)C1=CC=CC=C1 VBERTXPENGLIEG-UHFFFAOYSA-N 0.000 claims description 3
• BDTVIRQRXDRHGF-UHFFFAOYSA-N methyl 4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1CC1C(CCC(=O)OC)(C(=O)OC)N=CN1C(C)C1=CC=CC=C1 BDTVIRQRXDRHGF-UHFFFAOYSA-N 0.000 claims description 3
• NFSKAEQBOYBCAK-UHFFFAOYSA-N methyl 4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 NFSKAEQBOYBCAK-UHFFFAOYSA-N 0.000 claims description 3
• ZWPYOPROTVGVBN-UHFFFAOYSA-N methyl 4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 ZWPYOPROTVGVBN-UHFFFAOYSA-N 0.000 claims description 3
• ISCXJARTILLMPP-UHFFFAOYSA-N methyl 4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-[(4-chlorophenyl)methyl]-3-cyclohexyl-4h-imidazole-5-carboxylate Chemical compound N1=CN(C2CCCCC2)C(CC2CCC(CC2)C(N(C)C)C=2C=CC(Cl)=CC=2)C1(C(=O)OC)CC1=CC=C(Cl)C=C1 ISCXJARTILLMPP-UHFFFAOYSA-N 0.000 claims description 3
• DUDXSPVEEAMNEB-UHFFFAOYSA-N methyl 4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-[(4-chlorophenyl)methyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1CC1N(CCC)C=NC1(C(=O)OC)CC1=CC=C(Cl)C=C1 DUDXSPVEEAMNEB-UHFFFAOYSA-N 0.000 claims description 3
• XLDWAYVSNDCSBW-UHFFFAOYSA-N methyl 4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-3,5-dipropyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCC)(C(=O)OC)C1CC1CCC(C(CCC=2C=CC=CC=2)N(C)C)CC1 XLDWAYVSNDCSBW-UHFFFAOYSA-N 0.000 claims description 3
• ZHSVWBIMKQNTHM-UHFFFAOYSA-N methyl 4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(CCC=2C=CC=CC=2)N(C)C)CCC1CC1C(C(=O)OC)(CCSC)N=CN1C(C)C1=CC=CC=C1 ZHSVWBIMKQNTHM-UHFFFAOYSA-N 0.000 claims description 3
• BDNBBAXMEOAQJP-UHFFFAOYSA-N methyl 4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCSC)(C(=O)OC)C1CC1CCC(C(CCC=2C=CC=CC=2)N(C)C)CC1 BDNBBAXMEOAQJP-UHFFFAOYSA-N 0.000 claims description 3
• PLBONUWJQZOADP-UHFFFAOYSA-N methyl 4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(CCC=2C=CC=CC=2)N(C)C)CCC1CC1C(CCC(=O)OC)(C(=O)OC)N=CN1C(C)C1=CC=CC=C1 PLBONUWJQZOADP-UHFFFAOYSA-N 0.000 claims description 3
• PYBDTQRCOJCMFB-UHFFFAOYSA-N methyl 4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1CC1CCC(C(CCC=2C=CC=CC=2)N(C)C)CC1 PYBDTQRCOJCMFB-UHFFFAOYSA-N 0.000 claims description 3
• JNWXAISXZFYSPY-UHFFFAOYSA-N methyl 4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-methyl-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(CCC1=CC=CC=C1)N(C)C)C(C)C1=CC=CC=C1)C JNWXAISXZFYSPY-UHFFFAOYSA-N 0.000 claims description 3
• WLHLSMGXPCYYPU-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-3,5-dipropyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 WLHLSMGXPCYYPU-UHFFFAOYSA-N 0.000 claims description 3
• XYSWUMKLRGUTCG-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-methyl-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(C)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 XYSWUMKLRGUTCG-UHFFFAOYSA-N 0.000 claims description 3
• DUEMRIDOKVCHAO-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-3,5-dipropyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(F)=CC=2)CC1 DUEMRIDOKVCHAO-UHFFFAOYSA-N 0.000 claims description 3
• NLHQNESOJZRKOU-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(F)=CC=2)CC1 NLHQNESOJZRKOU-UHFFFAOYSA-N 0.000 claims description 3
• HYYPVXOREJPWCK-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-3-butyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1CC1N(CCCC)C=NC1(C(=O)OC)CSCC1=CC=CC=C1 HYYPVXOREJPWCK-UHFFFAOYSA-N 0.000 claims description 3
• LNSOHNWWBRUVKN-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-3-butyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound C1CC(C(CCC=2C=CC=CC=2)N(C)C)CCC1CC1N(CCCC)C=NC1(C(=O)OC)CSCC1=CC=CC=C1 LNSOHNWWBRUVKN-UHFFFAOYSA-N 0.000 claims description 3
• BKSFAMIJYPYVFD-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-3-butyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1CC1N(CCCC)C=NC1(C(=O)OC)CSCC1=CC=CC=C1 BKSFAMIJYPYVFD-UHFFFAOYSA-N 0.000 claims description 3
• VNSLSUKERKFYLK-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-3-cyclohexyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(C2CCCCC2)C(C2CCC(CC2)C(N(C)C)C=2C=C(F)C=CC=2)C1(C(=O)OC)CSCC1=CC=CC=C1 VNSLSUKERKFYLK-UHFFFAOYSA-N 0.000 claims description 3
• BMSRTONGNNEHSI-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-3-cyclohexyl-4h-imidazole-5-carboxylate Chemical compound N1=CN(C2CCCCC2)C(C2CCC(CC2)C(N(C)C)C=2C=CC(Cl)=CC=2)C1(C(=O)OC)CSCC1=CC=CC=C1 BMSRTONGNNEHSI-UHFFFAOYSA-N 0.000 claims description 3
• CXICYXNSHPYDBW-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1C1N(CCC)C=NC1(C(=O)OC)CSCC1=CC=CC=C1 CXICYXNSHPYDBW-UHFFFAOYSA-N 0.000 claims description 3
• CXGSCIVCHWYZCK-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1C1N(CCC)C=NC1(C(=O)OC)CSCC1=CC=CC=C1 CXGSCIVCHWYZCK-UHFFFAOYSA-N 0.000 claims description 3
• IQFJDUNSHNDMPA-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-3-cyclohexyl-4h-imidazole-5-carboxylate Chemical compound N1=CN(C2CCCCC2)C(CC2CCC(CC2)C(N(C)C)C=2C=CC(Cl)=CC=2)C1(C(=O)OC)CSCC1=CC=CC=C1 IQFJDUNSHNDMPA-UHFFFAOYSA-N 0.000 claims description 3
• FSEDYUOXARTCQS-UHFFFAOYSA-N methyl 5-[(4-chlorophenyl)methyl]-3-cyclohexyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(C2CCCCC2)C(C2CCC(CC2)C(N(C)C)C=2C=C(F)C=CC=2)C1(C(=O)OC)CC1=CC=C(Cl)C=C1 FSEDYUOXARTCQS-UHFFFAOYSA-N 0.000 claims description 3
• SCVGIOKQZFKPOH-UHFFFAOYSA-N methyl 5-[(4-chlorophenyl)methyl]-3-cyclohexyl-4-[[4-[dimethylamino(thiophen-2-yl)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(C2CCCCC2)C(CC2CCC(CC2)C(N(C)C)C=2SC=CC=2)C1(C(=O)OC)CC1=CC=C(Cl)C=C1 SCVGIOKQZFKPOH-UHFFFAOYSA-N 0.000 claims description 3
• FVASXSXRJLPEAX-UHFFFAOYSA-N methyl 5-butan-2-yl-3-butyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(C(C)CC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 FVASXSXRJLPEAX-UHFFFAOYSA-N 0.000 claims description 3
• YQSXCVHDRMLYEZ-UHFFFAOYSA-N methyl 5-butan-2-yl-3-butyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(C(C)CC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 YQSXCVHDRMLYEZ-UHFFFAOYSA-N 0.000 claims description 3
• WLJZCQLTOQQPED-UHFFFAOYSA-N methyl 5-butan-2-yl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(C(C)CC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 WLJZCQLTOQQPED-UHFFFAOYSA-N 0.000 claims description 3
• DERPEMCHDGVREK-UHFFFAOYSA-N methyl 5-butyl-3-cyclohexyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound CCCCC1(C(=O)OC)N=CN(C2CCCCC2)C1C(CC1)CCC1C(N(C)C)C1=CC=CC(F)=C1 DERPEMCHDGVREK-UHFFFAOYSA-N 0.000 claims description 3
• YQKNRFFVZLGAAC-UHFFFAOYSA-N methyl 5-butyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCCC1(C(=O)OC)N=CN(CCC)C1C1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 YQKNRFFVZLGAAC-UHFFFAOYSA-N 0.000 claims description 3
• VGRKVGNCRJBHDN-UHFFFAOYSA-N methyl 5-butyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCCC1(C(=O)OC)N=CN(CCC)C1CC1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 VGRKVGNCRJBHDN-UHFFFAOYSA-N 0.000 claims description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• AEDHDWSEIWJPNN-UHFFFAOYSA-N COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)C Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)C AEDHDWSEIWJPNN-UHFFFAOYSA-N 0.000 claims description 2
• JSVFNTXHMJSQAA-UHFFFAOYSA-N COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)C(C)CC Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)C(C)CC JSVFNTXHMJSQAA-UHFFFAOYSA-N 0.000 claims description 2
• VWNGOHLPRNXWSI-UHFFFAOYSA-N COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CCC Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC(=CC=C1)F)N(C)C)C(C)C1=CC=CC=C1)CCC VWNGOHLPRNXWSI-UHFFFAOYSA-N 0.000 claims description 2
• ZUQIBNCWRPPZGA-UHFFFAOYSA-N COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC=C(C=C1)F)N(C)C)C(C)C1=CC=CC=C1)C Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC=C(C=C1)F)N(C)C)C(C)C1=CC=CC=C1)C ZUQIBNCWRPPZGA-UHFFFAOYSA-N 0.000 claims description 2
• WGOOYOGUPPPBFZ-UHFFFAOYSA-N COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC=C(C=C1)F)N(C)C)C(C)C1=CC=CC=C1)CCC Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(C1=CC=C(C=C1)F)N(C)C)C(C)C1=CC=CC=C1)CCC WGOOYOGUPPPBFZ-UHFFFAOYSA-N 0.000 claims description 2
• RHGRPTRWSNOMSX-UHFFFAOYSA-N COC(=O)C1(N=CN(C1CC1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CC1=CC=C(C=C1)Cl Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(N(C)C)C1=CC=C(C=C1)Cl)C(C)C1=CC=CC=C1)CC1=CC=C(C=C1)Cl RHGRPTRWSNOMSX-UHFFFAOYSA-N 0.000 claims description 2
• RVLDMZMSKNSEKL-UHFFFAOYSA-N methyl 1-benzyl-5-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-4-(3-methoxy-3-oxopropyl)-4,5-dihydroimidazole-2-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(F)=CC=2)CCC1CC1C(CCC(=O)OC)N=C(C(=O)OC)N1CC1=CC=CC=C1 RVLDMZMSKNSEKL-UHFFFAOYSA-N 0.000 claims description 2
• CCXOXPMGQFLQHJ-UHFFFAOYSA-N methyl 3,5-dibutyl-4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCCC)(C(=O)OC)C1C1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 CCXOXPMGQFLQHJ-UHFFFAOYSA-N 0.000 claims description 2
• HZSDETPZXMKBHT-UHFFFAOYSA-N methyl 3,5-dibutyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCCC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(Cl)=CC=2)CC1 HZSDETPZXMKBHT-UHFFFAOYSA-N 0.000 claims description 2
• PBJSGMLNNZKQOM-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-4h-imidazole-5-carboxylate Chemical compound C1CC(C(CCC=2C=CC=CC=2)N(C)C)CCC1CC1C(C(=O)OC)(CCSC)N=CN1CC1=CC=CC=C1 PBJSGMLNNZKQOM-UHFFFAOYSA-N 0.000 claims description 2
• YLUHHXLCDOZSMK-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-methyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(CCC=2C=CC=CC=2)N(C)C)CCC1CC1C(C(=O)OC)(C)N=CN1CC1=CC=CC=C1 YLUHHXLCDOZSMK-UHFFFAOYSA-N 0.000 claims description 2
• SGYIPPLJSBCLBH-UHFFFAOYSA-N methyl 3-benzyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(CCC=2C=CC=CC=2)N(C)C)CCC1CC1C(CCC)(C(=O)OC)N=CN1CC1=CC=CC=C1 SGYIPPLJSBCLBH-UHFFFAOYSA-N 0.000 claims description 2
• LVNCRMSUSOJHHD-UHFFFAOYSA-N methyl 3-benzyl-5-butyl-4-[[4-[(2-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C(=CC=CC=2)Cl)CCC1CC1C(CCCC)(C(=O)OC)N=CN1CC1=CC=CC=C1 LVNCRMSUSOJHHD-UHFFFAOYSA-N 0.000 claims description 2
• MZIFSGBZMCSNOA-UHFFFAOYSA-N methyl 3-butyl-4-[4-[(2-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-5-(2-methylpropyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CC(C)C)(C(=O)OC)C1C1CCC(C(N(C)C)C=2C(=CC=CC=2)Cl)CC1 MZIFSGBZMCSNOA-UHFFFAOYSA-N 0.000 claims description 2
• ALOWJZPJDRSSTI-UHFFFAOYSA-N methyl 3-butyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1C1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 ALOWJZPJDRSSTI-UHFFFAOYSA-N 0.000 claims description 2
• QPNIIOCKINOLFT-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[(2-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-5-(2-methylpropyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CC(C)C)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C(=CC=CC=2)Cl)CC1 QPNIIOCKINOLFT-UHFFFAOYSA-N 0.000 claims description 2
• NKQQWQRRZRRFRX-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1CC1CCC(C(CCC=2C=CC=CC=2)N(C)C)CC1 NKQQWQRRZRRFRX-UHFFFAOYSA-N 0.000 claims description 2
• PBAAOJZERQIIBB-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 PBAAOJZERQIIBB-UHFFFAOYSA-N 0.000 claims description 2
• AJUOYZJWHWRCCU-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-methyl-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(C)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 AJUOYZJWHWRCCU-UHFFFAOYSA-N 0.000 claims description 2
• LPGVYFOFYXQYHY-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-propyl-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 LPGVYFOFYXQYHY-UHFFFAOYSA-N 0.000 claims description 2
• JKALKYGKBNRTHA-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-propyl-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(F)=CC=2)CC1 JKALKYGKBNRTHA-UHFFFAOYSA-N 0.000 claims description 2
• GNYPIBKKZXSZKO-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-4h-imidazole-5-carboxylate Chemical compound CSCCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)CCC1=CC=CC=C1 GNYPIBKKZXSZKO-UHFFFAOYSA-N 0.000 claims description 2
• SNTVZUISJPOPCK-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)CCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)CCC1=CC=CC=C1 SNTVZUISJPOPCK-UHFFFAOYSA-N 0.000 claims description 2
• NUDGQZDSDCRMDJ-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(CSC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)CCC1=CC=CC=C1 NUDGQZDSDCRMDJ-UHFFFAOYSA-N 0.000 claims description 2
• NGCDMEKTROWHHE-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)CCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=CC(F)=C1 NGCDMEKTROWHHE-UHFFFAOYSA-N 0.000 claims description 2
• OUYNSHAMKRABSI-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(CSC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=CC(F)=C1 OUYNSHAMKRABSI-UHFFFAOYSA-N 0.000 claims description 2
• VHKBTODLZLQWCR-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)CCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(F)C=C1 VHKBTODLZLQWCR-UHFFFAOYSA-N 0.000 claims description 2
• IAZCLGMPQUOEOY-UHFFFAOYSA-N methyl 3-cyclohexyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(CSC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(F)C=C1 IAZCLGMPQUOEOY-UHFFFAOYSA-N 0.000 claims description 2
• VBWXCKMTEHQIPD-UHFFFAOYSA-N methyl 4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-5-[(4-chlorophenyl)methyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1C1N(CCC)C=NC1(C(=O)OC)CC1=CC=C(Cl)C=C1 VBWXCKMTEHQIPD-UHFFFAOYSA-N 0.000 claims description 2
• VMWKTXSJEUCPKU-UHFFFAOYSA-N methyl 4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-5-(2-methylpropyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1C1C(C(=O)OC)(CC(C)C)N=CN1C(C)C1=CC=CC=C1 VMWKTXSJEUCPKU-UHFFFAOYSA-N 0.000 claims description 2
• ANVCXFPGVBXCOW-UHFFFAOYSA-N methyl 4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-3-cyclohexyl-5-(2-methylpropyl)-4h-imidazole-5-carboxylate Chemical compound COC(=O)C1(CC(C)C)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(Cl)C=C1 ANVCXFPGVBXCOW-UHFFFAOYSA-N 0.000 claims description 2
• JVQNSVNIQSDZQL-UHFFFAOYSA-N methyl 4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-3-(1-phenylethyl)-5-propyl-4H-imidazole-5-carboxylate Chemical compound COC(=O)C1(N=CN(C1CC1CCC(CC1)C(CCC1=CC=CC=C1)N(C)C)C(C)C1=CC=CC=C1)CCC JVQNSVNIQSDZQL-UHFFFAOYSA-N 0.000 claims description 2
• OXHFCRDSQJVWCH-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1CC1C(C(=O)OC)(CCSC)N=CN1C(C)C1=CC=CC=C1 OXHFCRDSQJVWCH-UHFFFAOYSA-N 0.000 claims description 2
• IWGGCJZBMXBIDZ-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 IWGGCJZBMXBIDZ-UHFFFAOYSA-N 0.000 claims description 2
• SQUOVQSUDQKHKP-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 SQUOVQSUDQKHKP-UHFFFAOYSA-N 0.000 claims description 2
• ZCGSVAGZEPPMSS-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 ZCGSVAGZEPPMSS-UHFFFAOYSA-N 0.000 claims description 2
• KYOZQSKUJRFGOU-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(F)=CC=2)CCC1CC1C(C(=O)OC)(CCSC)N=CN1C(C)C1=CC=CC=C1 KYOZQSKUJRFGOU-UHFFFAOYSA-N 0.000 claims description 2
• ASUOJGUWRMGALT-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-3-(1-phenylethyl)-4H-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(F)=CC=2)CCC1CC1C(CCC(=O)OC)(C(=O)OC)N=CN1C(C)C1=CC=CC=C1 ASUOJGUWRMGALT-UHFFFAOYSA-N 0.000 claims description 2
• GRSHKVALSFDMQZ-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(3-methoxy-3-oxopropyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CCC(=O)OC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(F)=CC=2)CC1 GRSHKVALSFDMQZ-UHFFFAOYSA-N 0.000 claims description 2
• NWPOHFOHYBJQKQ-UHFFFAOYSA-N methyl 4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(methylsulfanylmethyl)-3-propyl-4h-imidazole-5-carboxylate Chemical compound CCCN1C=NC(CSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(F)=CC=2)CC1 NWPOHFOHYBJQKQ-UHFFFAOYSA-N 0.000 claims description 2
• FFOOAAURSHVRMP-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-3-butyl-4-[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1C1N(CCCC)C=NC1(C(=O)OC)CSCC1=CC=CC=C1 FFOOAAURSHVRMP-UHFFFAOYSA-N 0.000 claims description 2
• AVXBEDJIZLNNCL-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-3-butyl-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1C1N(CCCC)C=NC1(C(=O)OC)CSCC1=CC=CC=C1 AVXBEDJIZLNNCL-UHFFFAOYSA-N 0.000 claims description 2
• PYSFUFAZWFPFAX-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-3-cyclohexyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(C2CCCCC2)C(CC2CCC(CC2)C(CCC=2C=CC=CC=2)N(C)C)C1(C(=O)OC)CSCC1=CC=CC=C1 PYSFUFAZWFPFAX-UHFFFAOYSA-N 0.000 claims description 2
• IWKWOZDLMDYKQR-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-3-cyclohexyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound N1=CN(C2CCCCC2)C(CC2CCC(CC2)C(N(C)C)C=2C=C(F)C=CC=2)C1(C(=O)OC)CSCC1=CC=CC=C1 IWKWOZDLMDYKQR-UHFFFAOYSA-N 0.000 claims description 2
• VGECIDUREMTGJU-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(Cl)=CC=2)CCC1CC1N(CCC)C=NC1(C(=O)OC)CSCC1=CC=CC=C1 VGECIDUREMTGJU-UHFFFAOYSA-N 0.000 claims description 2
• YZRLOXNTLZUMIM-UHFFFAOYSA-N methyl 5-(benzylsulfanylmethyl)-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=CC(F)=CC=2)CCC1CC1N(CCC)C=NC1(C(=O)OC)CSCC1=CC=CC=C1 YZRLOXNTLZUMIM-UHFFFAOYSA-N 0.000 claims description 2
• MOVJZAOFEKCKLI-UHFFFAOYSA-N methyl 5-[(4-chlorophenyl)methyl]-4-[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]-3-propyl-4h-imidazole-5-carboxylate Chemical compound C1CC(C(N(C)C)C=2C=C(F)C=CC=2)CCC1C1N(CCC)C=NC1(C(=O)OC)CC1=CC=C(Cl)C=C1 MOVJZAOFEKCKLI-UHFFFAOYSA-N 0.000 claims description 2
• UOBANTQSQBAULK-UHFFFAOYSA-N methyl 5-butan-2-yl-3-cyclohexyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound CCC(C)C1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=CC(F)=C1 UOBANTQSQBAULK-UHFFFAOYSA-N 0.000 claims description 2
• PMIRAVXKFWDXKT-UHFFFAOYSA-N methyl 5-butan-2-yl-3-cyclohexyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-4h-imidazole-5-carboxylate Chemical compound CCC(C)C1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(F)C=C1 PMIRAVXKFWDXKT-UHFFFAOYSA-N 0.000 claims description 2
• IOZOWVJZVPDWQS-UHFFFAOYSA-N methyl 5-butyl-4-[[4-[(4-chlorophenyl)-(dimethylamino)methyl]cyclohexyl]methyl]-3-cyclohexyl-4h-imidazole-5-carboxylate Chemical compound CCCCC1(C(=O)OC)N=CN(C2CCCCC2)C1CC(CC1)CCC1C(N(C)C)C1=CC=C(Cl)C=C1 IOZOWVJZVPDWQS-UHFFFAOYSA-N 0.000 claims description 2
• YTYAMJXQLTYBTK-UHFFFAOYSA-N 4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexane-1-carbaldehyde 4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexane-1-carbaldehyde 4-[1-(dimethylamino)-3-phenylpropyl]cyclohexane-1-carbaldehyde Chemical compound CN(C)C(C1CCC(CC1)C=O)C1=CC(=CC=C1)F.CN(C(CCC1=CC=CC=C1)C1CCC(CC1)C=O)C.CN(C)C(C1CCC(CC1)C=O)C1=CC=C(C=C1)F YTYAMJXQLTYBTK-UHFFFAOYSA-N 0.000 claims 1
• 208000020401 Depressive disease Diseases 0.000 claims 1
• MXZJLJCDQXVXEA-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCSC)(C(=O)OC)C1CC1CCC(C(CCC=2C=CC=CC=2)N(C)C)CC1 MXZJLJCDQXVXEA-UHFFFAOYSA-N 0.000 claims 1
• SBTIJPLBBCHHRC-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[1-(dimethylamino)-3-phenylpropyl]cyclohexyl]methyl]-5-propyl-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCC)(C(=O)OC)C1CC1CCC(C(CCC=2C=CC=CC=2)N(C)C)CC1 SBTIJPLBBCHHRC-UHFFFAOYSA-N 0.000 claims 1
• RDKJWOIQLZCMIU-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[dimethylamino-(3-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=C(F)C=CC=2)CC1 RDKJWOIQLZCMIU-UHFFFAOYSA-N 0.000 claims 1
• LLFKSPSUUKWVTI-UHFFFAOYSA-N methyl 3-butyl-4-[[4-[dimethylamino-(4-fluorophenyl)methyl]cyclohexyl]methyl]-5-(2-methylsulfanylethyl)-4h-imidazole-5-carboxylate Chemical compound CCCCN1C=NC(CCSC)(C(=O)OC)C1CC1CCC(C(N(C)C)C=2C=CC(F)=CC=2)CC1 LLFKSPSUUKWVTI-UHFFFAOYSA-N 0.000 claims 1
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