UA80120C2 - Glucocorticoid mimetics, pharmaceutical composition based thereon - Google Patents
Glucocorticoid mimetics, pharmaceutical composition based thereon Download PDFInfo
- Publication number
- UA80120C2 UA80120C2 UA20041008648A UA20041008648A UA80120C2 UA 80120 C2 UA80120 C2 UA 80120C2 UA 20041008648 A UA20041008648 A UA 20041008648A UA 20041008648 A UA20041008648 A UA 20041008648A UA 80120 C2 UA80120 C2 UA 80120C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methyl
- trifluoro
- ylmethyl
- fluoro
- methoxyphenyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- 239000003862 glucocorticoid Substances 0.000 title description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 364
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- 229940002612 prodrug Drugs 0.000 claims abstract description 57
- 239000000651 prodrug Substances 0.000 claims abstract description 57
- 239000012453 solvate Substances 0.000 claims abstract description 57
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 387
- -1 aminocarbonyloxy Chemical group 0.000 claims description 221
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 197
- 125000001424 substituent group Chemical group 0.000 claims description 120
- 150000003254 radicals Chemical class 0.000 claims description 119
- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 59
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
- 125000003342 alkenyl group Chemical group 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 150000001408 amides Chemical class 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 150000004702 methyl esters Chemical class 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000004434 sulfur atom Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 150000003457 sulfones Chemical class 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 150000003462 sulfoxides Chemical class 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 20
- 125000004043 oxo group Chemical group O=* 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 19
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 16
- NNBYAHPLGNHESK-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-phenyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 NNBYAHPLGNHESK-UHFFFAOYSA-N 0.000 claims description 15
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 14
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 13
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 13
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 13
- 125000001041 indolyl group Chemical group 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 12
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- HINCRROTVFUICG-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 HINCRROTVFUICG-UHFFFAOYSA-N 0.000 claims description 10
- LOHRDYFAXVJDTF-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound CC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 LOHRDYFAXVJDTF-UHFFFAOYSA-N 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 10
- DUPWFLAOXJABMP-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-(2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 DUPWFLAOXJABMP-UHFFFAOYSA-N 0.000 claims description 9
- ZEVOUDMOXREUQH-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-(3-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=CC(C(C)(C)CC(O)(CC=2NC3=CC=CC=C3C=2)C(F)(F)F)=C1 ZEVOUDMOXREUQH-UHFFFAOYSA-N 0.000 claims description 9
- JGIQIFOAVGJQSZ-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-(2-methylphenyl)pentan-2-ol Chemical compound CC1=CC=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 JGIQIFOAVGJQSZ-UHFFFAOYSA-N 0.000 claims description 9
- SSXCZELUNHJHQF-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-[3-(trifluoromethyl)phenyl]pentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(C(F)(F)F)=C1 SSXCZELUNHJHQF-UHFFFAOYSA-N 0.000 claims description 9
- BZCPPLRFFOYHHY-UHFFFAOYSA-N 1,1,1-trifluoro-4-(2-methoxyphenyl)-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound COC1=CC=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=CC=CC=C12 BZCPPLRFFOYHHY-UHFFFAOYSA-N 0.000 claims description 9
- BQFDDLPMAZIFJA-UHFFFAOYSA-N 1,1,1-trifluoro-4-(3-fluorophenyl)-4-methyl-2-[(4-methyl-1h-indol-2-yl)methyl]pentan-2-ol Chemical compound C=1C=2C(C)=CC=CC=2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(F)=C1 BQFDDLPMAZIFJA-UHFFFAOYSA-N 0.000 claims description 9
- BPNWRLGSGVFULW-UHFFFAOYSA-N 1,1,1-trifluoro-4-(3-methoxyphenyl)-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound COC1=CC=CC(C(C)(C)CC(O)(CC=2C3=CC=CC=C3N=CC=2)C(F)(F)F)=C1 BPNWRLGSGVFULW-UHFFFAOYSA-N 0.000 claims description 9
- QHTICTLHALFTKE-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluoro-2-methoxyphenyl)-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 QHTICTLHALFTKE-UHFFFAOYSA-N 0.000 claims description 9
- VJUQJVSNWZXJNG-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluoro-2-methoxyphenyl)-4-methyl-2-(5,6,7,8-tetrahydroquinolin-4-ylmethyl)pentan-2-ol Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=C1CCCC2 VJUQJVSNWZXJNG-UHFFFAOYSA-N 0.000 claims description 9
- GDQRBBODPQZBJE-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluoro-2-methoxyphenyl)-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=CC=CC=C12 GDQRBBODPQZBJE-UHFFFAOYSA-N 0.000 claims description 9
- PRWLUWXEPRMYHC-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluorophenyl)-4-methyl-2-[(4-methyl-1h-indol-2-yl)methyl]pentan-2-ol Chemical compound C=1C=2C(C)=CC=CC=2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 PRWLUWXEPRMYHC-UHFFFAOYSA-N 0.000 claims description 9
- KYILFYYEUKXGSZ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-[(4-methyl-1h-indol-2-yl)methyl]pentan-2-ol Chemical compound CC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=C(C)C=CC=C2N1 KYILFYYEUKXGSZ-UHFFFAOYSA-N 0.000 claims description 9
- RGEBCARNFMSLJW-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)-4-[3-(trifluoromethyl)phenyl]pentan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(C(F)(F)F)=C1 RGEBCARNFMSLJW-UHFFFAOYSA-N 0.000 claims description 9
- GCKNMQIBTQCWOW-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-(5-methyl-2,3-dihydro-1-benzofuran-7-yl)-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C1=CC=C2C(CC(O)(CC(C)(C)C=3C=4OCCC=4C=C(C=3)C)C(F)(F)F)=CC=NC2=C1 GCKNMQIBTQCWOW-UHFFFAOYSA-N 0.000 claims description 9
- DXOQPLYIBQRHNE-UHFFFAOYSA-N 2-[(2,6-dichloropyridin-4-yl)methyl]-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC(Cl)=NC(Cl)=C1 DXOQPLYIBQRHNE-UHFFFAOYSA-N 0.000 claims description 9
- NNTHLQVZGURUAX-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCC2 NNTHLQVZGURUAX-UHFFFAOYSA-N 0.000 claims description 9
- KNPSVTJNZFMZCK-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCC2 KNPSVTJNZFMZCK-UHFFFAOYSA-N 0.000 claims description 9
- YRFFGAKAOAFAAM-UHFFFAOYSA-N 4-(5-bromo-2-methoxyphenyl)-1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 YRFFGAKAOAFAAM-UHFFFAOYSA-N 0.000 claims description 9
- RXZIEDJKPJAEHF-UHFFFAOYSA-N 4-(5-bromo-2-methoxyphenyl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=CC=CC=C12 RXZIEDJKPJAEHF-UHFFFAOYSA-N 0.000 claims description 9
- XUCNQJXHQCKOJI-UHFFFAOYSA-N 4-(5-bromo-4-fluoro-2-methoxyphenyl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound COC1=CC(F)=C(Br)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=CC=CC=C12 XUCNQJXHQCKOJI-UHFFFAOYSA-N 0.000 claims description 9
- XHRGPBXBIQZZGI-UHFFFAOYSA-N 4-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C(C=C1Br)=CC2=C1OCC2 XHRGPBXBIQZZGI-UHFFFAOYSA-N 0.000 claims description 9
- YWLNVHAUUYYOKM-UHFFFAOYSA-N 4-bromo-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(quinolin-4-ylmethyl)pentan-2-yl]phenol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(Br)=CC=C1O YWLNVHAUUYYOKM-UHFFFAOYSA-N 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 9
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- USMFOMVHIKQVEN-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-(5-methyl-2,3-dihydro-1-benzofuran-7-yl)pentan-2-ol Chemical compound C1=CC=C2NC(CC(O)(CC(C)(C)C=3C=4OCCC=4C=C(C=3)C)C(F)(F)F)=CC2=C1 USMFOMVHIKQVEN-UHFFFAOYSA-N 0.000 claims description 8
- BCWFWNBNYVPLRF-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(7-fluoro-1h-indol-2-yl)methyl]-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC(F)=C2N1 BCWFWNBNYVPLRF-UHFFFAOYSA-N 0.000 claims description 8
- BPMHJOIMPDPVBS-UHFFFAOYSA-N 1,1,1-trifluoro-4-(3-fluorophenyl)-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(F)=C1 BPMHJOIMPDPVBS-UHFFFAOYSA-N 0.000 claims description 8
- QICUTOZJKBWXDZ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluorophenyl)-2-[(5-fluoroquinolin-4-yl)methyl]-4-methylpentan-2-ol Chemical compound C=1C=NC2=CC=CC(F)=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 QICUTOZJKBWXDZ-UHFFFAOYSA-N 0.000 claims description 8
- UUIWYLMDKKQBJQ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2,3-dihydro-1-benzofuran-7-yl)-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC2=C1OCC2 UUIWYLMDKKQBJQ-UHFFFAOYSA-N 0.000 claims description 8
- OYHFMGSEEBIQAO-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2,3-dihydro-1-benzofuran-7-yl)-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC2=C1OCC2 OYHFMGSEEBIQAO-UHFFFAOYSA-N 0.000 claims description 8
- ZDGKSVJQXBLJCQ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-2-[(7-fluoroquinolin-4-yl)methyl]-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=CC(F)=CC=C12 ZDGKSVJQXBLJCQ-UHFFFAOYSA-N 0.000 claims description 8
- GYORCMNBZVAVFU-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=CC=CC=C12 GYORCMNBZVAVFU-UHFFFAOYSA-N 0.000 claims description 8
- IZEQVUQTMWGQGC-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NC2=CC=CC=C2N1 IZEQVUQTMWGQGC-UHFFFAOYSA-N 0.000 claims description 8
- OJTDOISCGJSBED-UHFFFAOYSA-N 2-[2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carbonitrile Chemical compound C=1C2=CC(C#N)=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 OJTDOISCGJSBED-UHFFFAOYSA-N 0.000 claims description 8
- JYZHKMJQCRYWMS-UHFFFAOYSA-N 2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(quinolin-4-ylmethyl)pentan-2-yl]phenol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1O JYZHKMJQCRYWMS-UHFFFAOYSA-N 0.000 claims description 8
- PKGWJFNRGGGBJB-UHFFFAOYSA-N 4-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(Br)=CC2=C1OCC2 PKGWJFNRGGGBJB-UHFFFAOYSA-N 0.000 claims description 8
- VPHCWEPTKXINGC-UHFFFAOYSA-N 4-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(Br)=CC2=C1OCC2 VPHCWEPTKXINGC-UHFFFAOYSA-N 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000003435 aroyl group Chemical group 0.000 claims description 8
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
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- NFZVFCYMIGXGEO-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-(4-methoxyphenyl)-4-methylpentan-2-ol Chemical compound C1=CC(OC)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 NFZVFCYMIGXGEO-UHFFFAOYSA-N 0.000 claims description 7
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