NO329386B1 - Glukocorticoid-mimetica, farmasoytiske preparater og anvendelser for fremstilling av medikamenterfor behandling av sykdom - Google Patents
Glukocorticoid-mimetica, farmasoytiske preparater og anvendelser for fremstilling av medikamenterfor behandling av sykdom Download PDFInfo
- Publication number
- NO329386B1 NO329386B1 NO20044031A NO20044031A NO329386B1 NO 329386 B1 NO329386 B1 NO 329386B1 NO 20044031 A NO20044031 A NO 20044031A NO 20044031 A NO20044031 A NO 20044031A NO 329386 B1 NO329386 B1 NO 329386B1
- Authority
- NO
- Norway
- Prior art keywords
- trifluoro
- methyl
- ylmethyl
- fluoro
- methoxyphenyl
- Prior art date
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 57
- 201000010099 disease Diseases 0.000 title claims abstract description 49
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000003814 drug Substances 0.000 title description 29
- 239000003862 glucocorticoid Substances 0.000 title description 26
- 229940079593 drug Drugs 0.000 title description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 227
- 102000003676 Glucocorticoid Receptors Human genes 0.000 claims abstract description 65
- 108090000079 Glucocorticoid Receptors Proteins 0.000 claims abstract description 65
- 150000003839 salts Chemical class 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 44
- 239000012453 solvate Substances 0.000 claims abstract description 35
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 15
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 11
- 230000000172 allergic effect Effects 0.000 claims abstract description 10
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- 230000002062 proliferating effect Effects 0.000 claims abstract description 6
- -1 Aminocarbonyloxy Chemical group 0.000 claims description 168
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 101
- 125000001424 substituent group Chemical group 0.000 claims description 74
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 72
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 32
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 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 16
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 14
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Chemical group 0.000 claims description 10
- 150000003457 sulfones Chemical class 0.000 claims description 10
- 150000003462 sulfoxides Chemical class 0.000 claims description 10
- 239000011593 sulfur 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
- SLPDUPWHPOHLGL-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluoro-2-methoxyphenyl)-4-methyl-2-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CN=CC=C2N1 SLPDUPWHPOHLGL-UHFFFAOYSA-N 0.000 claims description 9
- DJRNAIGSFHOUFL-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=NC=C2N1 DJRNAIGSFHOUFL-UHFFFAOYSA-N 0.000 claims description 9
- 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 9
- QPLQDYDXYCUKKE-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound CC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=NC=C2N1 QPLQDYDXYCUKKE-UHFFFAOYSA-N 0.000 claims description 9
- ULOAOMMDFZMTER-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-phenyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CC=NC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 ULOAOMMDFZMTER-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
- 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 9
- 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 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
- 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000006274 (C1-C3)alkoxy group Chemical group 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
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- GFYMYOFEBUNRKS-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-phenyl-2-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CN=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 GFYMYOFEBUNRKS-UHFFFAOYSA-N 0.000 claims description 8
- 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 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
- 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 8
- 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 8
- LTJPVQNAJLSDLD-UHFFFAOYSA-N 5-fluoro-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=C(F)C=C1O LTJPVQNAJLSDLD-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- NLSXBFBIPNXUCU-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-(1-methoxynaphthalen-2-yl)-4-methylpentan-2-ol Chemical compound C1=CC=C2NC(CC(O)(CC(C)(C)C3=C(C4=CC=CC=C4C=C3)OC)C(F)(F)F)=CC2=C1 NLSXBFBIPNXUCU-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 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
- 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 7
- SUWLVCMUNWXUAI-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-naphthalen-2-ylpentan-2-ol Chemical compound C1=CC=CC2=CC(C(C)(CC(O)(CC=3NC4=CC=CC=C4C=3)C(F)(F)F)C)=CC=C21 SUWLVCMUNWXUAI-UHFFFAOYSA-N 0.000 claims description 7
- GEROBJZBAHWBME-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-phenylpentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 GEROBJZBAHWBME-UHFFFAOYSA-N 0.000 claims description 7
- GJRFHWFGIKDJJU-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-thiophen-3-ylpentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C=1C=CSC=1 GJRFHWFGIKDJJU-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- KZFHKECQQKPSOW-UHFFFAOYSA-N 1,1,1-trifluoro-4-(1-methoxynaphthalen-2-yl)-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C1=CC=C2C(CC(O)(CC(C)(C)C3=C(C4=CC=CC=C4C=C3)OC)C(F)(F)F)=CC=NC2=C1 KZFHKECQQKPSOW-UHFFFAOYSA-N 0.000 claims description 7
- ANPFZNKOHNLVIS-UHFFFAOYSA-N 1,1,1-trifluoro-4-(3-fluorophenyl)-4-methyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CC=NC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(F)=C1 ANPFZNKOHNLVIS-UHFFFAOYSA-N 0.000 claims description 7
- PLDKOIHIMFYGJQ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(3-fluorophenyl)-4-methyl-2-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CN=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(F)=C1 PLDKOIHIMFYGJQ-UHFFFAOYSA-N 0.000 claims description 7
- IJMQRMGMMOFNAQ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluoro-2-methoxyphenyl)-4-methyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=NC=C2N1 IJMQRMGMMOFNAQ-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- BOLIDOPRDLKIKT-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluorophenyl)-2-[(7-fluoroquinolin-4-yl)methyl]-4-methylpentan-2-ol Chemical compound C=1C=NC2=CC(F)=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 BOLIDOPRDLKIKT-UHFFFAOYSA-N 0.000 claims description 7
- XDSTVLMUZWFFOB-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluorophenyl)-4-methyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CC=NC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 XDSTVLMUZWFFOB-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 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 7
- HKLWSBIHHHYTLH-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CN=CC=C2N1 HKLWSBIHHHYTLH-UHFFFAOYSA-N 0.000 claims description 7
- USJCSARQNZRHOH-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(3-methyl-1h-pyrrolo[2,3-c]pyridin-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=C(C)C2=CC=NC=C2N1 USJCSARQNZRHOH-UHFFFAOYSA-N 0.000 claims description 7
- GYLMWPZPOHYPKG-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(4-methyl-1h-benzimidazol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NC2=CC=CC(C)=C2N1 GYLMWPZPOHYPKG-UHFFFAOYSA-N 0.000 claims description 7
- AMFCTLVRUQTYNN-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-[(4-methyl-1h-benzimidazol-2-yl)methyl]pentan-2-ol Chemical compound CC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NC2=CC=CC(C)=C2N1 AMFCTLVRUQTYNN-UHFFFAOYSA-N 0.000 claims description 7
- QHIDWZQTAZIRHR-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-naphthalen-2-yl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C1=CC=CC2=CC(C(C)(CC(O)(CC=3C4=CC=CC=C4N=CC=3)C(F)(F)F)C)=CC=C21 QHIDWZQTAZIRHR-UHFFFAOYSA-N 0.000 claims description 7
- SZSZDBFJCQKTRG-UHFFFAOYSA-N 1h-indole-6-carbonitrile Chemical compound N#CC1=CC=C2C=CNC2=C1 SZSZDBFJCQKTRG-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- IYZGETQLLSRYCB-UHFFFAOYSA-N 2-[(4,5-difluoro-1h-benzimidazol-2-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=NC2=CC=C(F)C(F)=C2N1 IYZGETQLLSRYCB-UHFFFAOYSA-N 0.000 claims description 7
- IXVTYKJTKOLGMW-UHFFFAOYSA-N 2-[(4,6-dimethyl-1h-benzimidazol-2-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=NC2=CC(C)=CC(C)=C2N1 IXVTYKJTKOLGMW-UHFFFAOYSA-N 0.000 claims description 7
- SKNXJHVYZREZQE-UHFFFAOYSA-N 2-[2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound C=1C=2C(C)=CC(C#N)=CC=2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 SKNXJHVYZREZQE-UHFFFAOYSA-N 0.000 claims description 7
- USMOYLYDVYZSFQ-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound C=1C=2C(C)=CC(C#N)=CC=2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(F)=C1 USMOYLYDVYZSFQ-UHFFFAOYSA-N 0.000 claims description 7
- KOARJQIBXYNLDX-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound C=1C=2C(C)=CC(C#N)=CC=2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 KOARJQIBXYNLDX-UHFFFAOYSA-N 0.000 claims description 7
- FMWNCAILQDBGQO-UHFFFAOYSA-N 2-[4-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound N1C2=CC=CC=C2C(C#N)=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(Br)=CC2=C1OCC2 FMWNCAILQDBGQO-UHFFFAOYSA-N 0.000 claims description 7
- RCHKMEIVQJJPEJ-UHFFFAOYSA-N 2-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=C(C)C=C(C#N)C=C2N1 RCHKMEIVQJJPEJ-UHFFFAOYSA-N 0.000 claims description 7
- BQBQHUCHUURBBK-UHFFFAOYSA-N 2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(quinolin-4-ylmethyl)pentan-2-yl]naphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C(C)(CC(O)(CC=3C4=CC=CC=C4N=CC=3)C(F)(F)F)C)=CC=C21 BQBQHUCHUURBBK-UHFFFAOYSA-N 0.000 claims description 7
- PZOGJBZBKUZEII-UHFFFAOYSA-N 3-[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(O)=C1 PZOGJBZBKUZEII-UHFFFAOYSA-N 0.000 claims description 7
- VGTCAEJTZVIZCE-UHFFFAOYSA-N 3-[5,5,5-trifluoro-4-hydroxy-4-(1h-indol-2-ylmethyl)-2-methylpentan-2-yl]phenol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(O)=C1 VGTCAEJTZVIZCE-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- SLISGNAJVILLSI-UHFFFAOYSA-N 4-(3,4-dihydro-2h-chromen-8-yl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C1CCOC2=C1C=CC=C2C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=CC=CC=C12 SLISGNAJVILLSI-UHFFFAOYSA-N 0.000 claims description 7
- KXJHLNHXRLTVLW-UHFFFAOYSA-N 4-fluoro-2-[5,5,5-trifluoro-4-[(7-fluoro-1h-indol-2-yl)methyl]-4-hydroxy-2-methylpentan-2-yl]phenol Chemical compound C=1C2=CC=CC(F)=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O KXJHLNHXRLTVLW-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 6
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 6
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 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 6
- DFRDWNXFQZYOEF-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(6-fluoro-1h-benzimidazol-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=NC2=CC=C(F)C=C2N1 DFRDWNXFQZYOEF-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- IHBNWWGBASPVLH-UHFFFAOYSA-N 1,1,1-trifluoro-4-(3-methoxyphenyl)-4-methyl-2-[[5-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound COC1=CC=CC(C(C)(C)CC(O)(CC=2NC3=CC=C(C=C3C=2)C(F)(F)F)C(F)(F)F)=C1 IHBNWWGBASPVLH-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 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 6
- XGXAKFFLMCSPMQ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(2-phenylimidazol-1-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C(C=2C=CC=CC=2)=NC=C1 XGXAKFFLMCSPMQ-UHFFFAOYSA-N 0.000 claims description 6
- OWKCEPYQUOFRFE-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(4-methyl-2-phenylimidazol-1-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C(C=2C=CC=CC=2)=NC(C)=C1 OWKCEPYQUOFRFE-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 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 6
- QWINIJIEBGMKHN-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)-4-thiophen-3-ylpentan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C=1C=CSC=1 QWINIJIEBGMKHN-UHFFFAOYSA-N 0.000 claims description 6
- GVEJOTUVUWNIDS-UHFFFAOYSA-N 2-[(2-chloropyridin-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=NC(Cl)=C1 GVEJOTUVUWNIDS-UHFFFAOYSA-N 0.000 claims description 6
- AUESDSZZWVSGRT-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-hydroxy-4-methyl-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=C(F)C=C1 AUESDSZZWVSGRT-UHFFFAOYSA-N 0.000 claims description 6
- PLGFUOXTFWTJQT-UHFFFAOYSA-N 2-[4-[(2,6-dichloropyridin-4-yl)methyl]-5,5,5-trifluoro-4-hydroxy-2-methylpentan-2-yl]-4-fluorophenol Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(F)(F)F)CC1=CC(Cl)=NC(Cl)=C1 PLGFUOXTFWTJQT-UHFFFAOYSA-N 0.000 claims description 6
- DULDZGGFYZBZAI-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-5-yl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C1=C2OCCC2=CC(C(C)(CC(O)(CC=2C3=CC=CC=C3N=CC=2)C(F)(F)F)C)=C1 DULDZGGFYZBZAI-UHFFFAOYSA-N 0.000 claims description 6
- LQEYCNOVTFYYNT-UHFFFAOYSA-N 4-(2,6-dimethylphenyl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound CC1=CC=CC(C)=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=CC=CC=C12 LQEYCNOVTFYYNT-UHFFFAOYSA-N 0.000 claims description 6
- LFLIFMULNYMVKK-UHFFFAOYSA-N 4-(3-ethyl-2-methoxyphenyl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound CCC1=CC=CC(C(C)(C)CC(O)(CC=2C3=CC=CC=C3N=CC=2)C(F)(F)F)=C1OC LFLIFMULNYMVKK-UHFFFAOYSA-N 0.000 claims description 6
- ICEYZVIJKKLKPQ-UHFFFAOYSA-N 4-(6-bromo-3,4-dihydro-2h-chromen-8-yl)-1,1,1-trifluoro-4-methyl-2-(quinolin-4-ylmethyl)pentan-2-ol Chemical compound C1CCOC2=C1C=C(Br)C=C2C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC2=CC=CC=C12 ICEYZVIJKKLKPQ-UHFFFAOYSA-N 0.000 claims description 6
- 208000012902 Nervous system disease Diseases 0.000 claims description 6
- 208000025966 Neurological disease Diseases 0.000 claims description 6
- 208000025747 Rheumatic disease Diseases 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 230000001919 adrenal effect Effects 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- PIEOAZCXKHZQBV-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-(4-methylphenyl)pentan-2-ol Chemical compound C1=CC(C)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 PIEOAZCXKHZQBV-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 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 5
- XBZXAMJYRGXECA-UHFFFAOYSA-N 1-[4-(2,3-dihydro-1-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]indole-3-carbonitrile Chemical compound C1=C(C#N)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCC2 XBZXAMJYRGXECA-UHFFFAOYSA-N 0.000 claims description 5
- XWVDHKMHPOKLKO-UHFFFAOYSA-N 2-[2-hydroxy-4-(3-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound COC1=CC=CC(C(C)(C)CC(O)(CC=2NC3=CC(=CC(C)=C3C=2)C#N)C(F)(F)F)=C1 XWVDHKMHPOKLKO-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- IVPSJHJAAPZNIN-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)-2-hydroxy-4-methyl-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(F)=C1 IVPSJHJAAPZNIN-UHFFFAOYSA-N 0.000 claims description 5
- VTYZNTMDLMMGMW-UHFFFAOYSA-N 2-[4-(4-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-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=C(F)C=C1O VTYZNTMDLMMGMW-UHFFFAOYSA-N 0.000 claims description 5
- WIBFEMNIEOWHBW-UHFFFAOYSA-N 2-[4-(4-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carbonitrile Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C#N)=CC=C2N1 WIBFEMNIEOWHBW-UHFFFAOYSA-N 0.000 claims description 5
- QMRUOODXWAEHCK-UHFFFAOYSA-N 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carboxamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C(N)=O)=CC=C2N1 QMRUOODXWAEHCK-UHFFFAOYSA-N 0.000 claims description 5
- QDLIZDYYYDEGAP-UHFFFAOYSA-N 2-[4-[(2-chloroquinolin-4-yl)methyl]-5,5,5-trifluoro-4-hydroxy-2-methylpentan-2-yl]-4-fluorophenol Chemical compound C=1C(Cl)=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O QDLIZDYYYDEGAP-UHFFFAOYSA-N 0.000 claims description 5
- AFQWVQYUXVOOQO-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-2-[(7-fluoro-1h-indol-2-yl)methyl]-4-methylpentan-2-ol Chemical compound C=1C2=CC=CC(F)=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCC2 AFQWVQYUXVOOQO-UHFFFAOYSA-N 0.000 claims description 5
- QOZZBCZFOZCNQK-UHFFFAOYSA-N 7-[5,5,5-trifluoro-4-hydroxy-4-(1h-indol-2-ylmethyl)-2-methylpentan-2-yl]-2,3-dihydro-1-benzofuran-5-carbonitrile Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(C#N)=CC2=C1OCC2 QOZZBCZFOZCNQK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 125000003435 aroyl group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- ZJGBFIBRJHQFCH-UHFFFAOYSA-N methyl 2-[4-(4-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carboxylate Chemical compound C=1C2=CC(C(=O)OC)=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1OC ZJGBFIBRJHQFCH-UHFFFAOYSA-N 0.000 claims description 5
- PETRTAAVHJUNEX-UHFFFAOYSA-N methyl 2-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carboxylate Chemical compound C=1C2=CC(C(=O)OC)=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(Br)=CC=C1OC PETRTAAVHJUNEX-UHFFFAOYSA-N 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- DQNHEYWVKKTREE-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(7-fluoro-1h-indol-2-yl)methyl]-4-methyl-4-phenylpentan-2-ol Chemical compound C=1C2=CC=CC(F)=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 DQNHEYWVKKTREE-UHFFFAOYSA-N 0.000 claims description 4
- BMSOMRULZKHEPL-UHFFFAOYSA-N 2-[(2-chloroquinolin-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)=NC2=CC=CC=C12 BMSOMRULZKHEPL-UHFFFAOYSA-N 0.000 claims description 4
- HCEASXKSEDQONW-UHFFFAOYSA-N 2-[2-hydroxy-4-(3-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carbonitrile Chemical compound COC1=CC=CC(C(C)(C)CC(O)(CC=2NC3=CC=C(C=C3C=2)C#N)C(F)(F)F)=C1 HCEASXKSEDQONW-UHFFFAOYSA-N 0.000 claims description 4
- BVKNEEHRUPFXKI-UHFFFAOYSA-N 2-[2-hydroxy-4-methyl-4-phenyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound N1C2=CC=CC=C2C(C#N)=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1 BVKNEEHRUPFXKI-UHFFFAOYSA-N 0.000 claims description 4
- AYUHUGSCKKIDFF-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1-benzofuran-7-yl)-2-hydroxy-4-methyl-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=CC2=C1OCC2 AYUHUGSCKKIDFF-UHFFFAOYSA-N 0.000 claims description 4
- YFAOESSGNMZISB-UHFFFAOYSA-N 2-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound C=1C=2C(C)=CC(C#N)=CC=2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O YFAOESSGNMZISB-UHFFFAOYSA-N 0.000 claims description 4
- JHVUZNHBPRRJBX-UHFFFAOYSA-N 2-[4-[(2-chloropyridin-4-yl)methyl]-5,5,5-trifluoro-4-hydroxy-2-methylpentan-2-yl]-4-fluorophenol Chemical compound C=1C(F)=CC=C(O)C=1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC(Cl)=C1 JHVUZNHBPRRJBX-UHFFFAOYSA-N 0.000 claims description 4
- LSVLESAUMAVYQD-UHFFFAOYSA-N 2-[4-[(4,6-dimethyl-1h-benzimidazol-2-yl)methyl]-5,5,5-trifluoro-4-hydroxy-2-methylpentan-2-yl]-4-fluorophenol Chemical compound N=1C2=CC(C)=CC(C)=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O LSVLESAUMAVYQD-UHFFFAOYSA-N 0.000 claims description 4
- NKYOEYPIQBZEFS-UHFFFAOYSA-N 2-ethyl-6-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(quinolin-4-ylmethyl)pentan-2-yl]phenol Chemical compound CCC1=CC=CC(C(C)(C)CC(O)(CC=2C3=CC=CC=C3N=CC=2)C(F)(F)F)=C1O NKYOEYPIQBZEFS-UHFFFAOYSA-N 0.000 claims description 4
- SBLAWIRDDWUXFJ-UHFFFAOYSA-N 2-ethyl-6-[5,5,5-trifluoro-4-hydroxy-4-(1h-indol-2-ylmethyl)-2-methylpentan-2-yl]phenol Chemical compound CCC1=CC=CC(C(C)(C)CC(O)(CC=2NC3=CC=CC=C3C=2)C(F)(F)F)=C1O SBLAWIRDDWUXFJ-UHFFFAOYSA-N 0.000 claims description 4
- TWYKKBHWFGXBOH-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-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=C(Cl)C(Cl)=C1 TWYKKBHWFGXBOH-UHFFFAOYSA-N 0.000 claims description 4
- PPZFUNVOMAEIRC-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-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=C(F)C(F)=C1 PPZFUNVOMAEIRC-UHFFFAOYSA-N 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000007913 Pituitary Neoplasms Diseases 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- NGIMZRPAXNAGHH-UHFFFAOYSA-N methyl 2-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-6-carboxylate Chemical compound N1C2=CC(C(=O)OC)=CC=C2C=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O NGIMZRPAXNAGHH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- FGPTVWSEADMQBZ-UHFFFAOYSA-N 1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methyl-4-pyridin-2-ylpentan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=N1 FGPTVWSEADMQBZ-UHFFFAOYSA-N 0.000 claims description 3
- KNEYKCUMUCBZNB-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(6-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=C(F)C=C2N1 KNEYKCUMUCBZNB-UHFFFAOYSA-N 0.000 claims description 3
- HMFLWDMRCSPEKE-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(7-fluoro-1h-indol-2-yl)methyl]-4-(4-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC(F)=C2N1 HMFLWDMRCSPEKE-UHFFFAOYSA-N 0.000 claims description 3
- NPDROCFMZCYVGA-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(7-fluoro-1h-indol-2-yl)methyl]-4-(4-fluorophenyl)-4-methylpentan-2-ol Chemical compound C=1C2=CC=CC(F)=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 NPDROCFMZCYVGA-UHFFFAOYSA-N 0.000 claims description 3
- ICYYQBKTTWAOTH-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(7-fluoro-1h-indol-2-yl)methyl]-4-(5-fluoro-2-methylphenyl)-4-methylpentan-2-ol Chemical compound CC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC(F)=C2N1 ICYYQBKTTWAOTH-UHFFFAOYSA-N 0.000 claims description 3
- XEBKNJMUCCJLCQ-UHFFFAOYSA-N 1,1,1-trifluoro-2-[[1-(4-fluorophenyl)cyclopropyl]methyl]-3-(1h-indol-2-yl)propan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC1(C=2C=CC(F)=CC=2)CC1 XEBKNJMUCCJLCQ-UHFFFAOYSA-N 0.000 claims description 3
- NCBSBCXNCTUHJA-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluoro-2-methoxyphenyl)-4-methyl-2-[[5-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C(F)(F)F)=CC=C2N1 NCBSBCXNCTUHJA-UHFFFAOYSA-N 0.000 claims description 3
- QBKCPBAHFMEZRA-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluorophenyl)-4-methyl-2-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CN=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 QBKCPBAHFMEZRA-UHFFFAOYSA-N 0.000 claims description 3
- JLAWYYSURNAWJG-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-2-[(2-fluoropyridin-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=NC(F)=C1 JLAWYYSURNAWJG-UHFFFAOYSA-N 0.000 claims description 3
- JYZRBYOHMWPNEL-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(pyridin-2-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=CC=N1 JYZRBYOHMWPNEL-UHFFFAOYSA-N 0.000 claims description 3
- YHGOQAJBOFCBRJ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(1-methylindol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1C YHGOQAJBOFCBRJ-UHFFFAOYSA-N 0.000 claims description 3
- BERMAIZPHSZFBG-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(3-methyl-1h-indol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=C(C)C2=CC=CC=C2N1 BERMAIZPHSZFBG-UHFFFAOYSA-N 0.000 claims description 3
- MIEQHOMXSUWXEK-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-nitro-1h-indol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC([N+]([O-])=O)=CC=C2N1 MIEQHOMXSUWXEK-UHFFFAOYSA-N 0.000 claims description 3
- JZFUUMIFIPVITG-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(6-methyl-1h-indol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=C(C)C=C2N1 JZFUUMIFIPVITG-UHFFFAOYSA-N 0.000 claims description 3
- WHCDWQKQXRPMKS-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[[4-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=C(C(F)(F)F)C=CC=C2N1 WHCDWQKQXRPMKS-UHFFFAOYSA-N 0.000 claims description 3
- HGNYBRFKHNQBPB-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[[5-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C(F)(F)F)=CC=C2N1 HGNYBRFKHNQBPB-UHFFFAOYSA-N 0.000 claims description 3
- NBSZSBITSXNGHC-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[[6-(trifluoromethyl)-1h-benzimidazol-2-yl]methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NC2=CC=C(C(F)(F)F)C=C2N1 NBSZSBITSXNGHC-UHFFFAOYSA-N 0.000 claims description 3
- NIJXJFCGNYEYSG-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[[6-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=C(C(F)(F)F)C=C2N1 NIJXJFCGNYEYSG-UHFFFAOYSA-N 0.000 claims description 3
- WPABLAUGQPSKHQ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[[7-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC(C(F)(F)F)=C2N1 WPABLAUGQPSKHQ-UHFFFAOYSA-N 0.000 claims description 3
- NBFOBKAWNMHDGY-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-[[5-(trifluoromethyl)-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=CC(C(F)(F)F)=CC=C2N1 NBFOBKAWNMHDGY-UHFFFAOYSA-N 0.000 claims description 3
- GMEQBMRWYQQDNV-UHFFFAOYSA-N 2-[(2-bromopyridin-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=NC(Br)=C1 GMEQBMRWYQQDNV-UHFFFAOYSA-N 0.000 claims description 3
- METQZGZXPFILTQ-UHFFFAOYSA-N 2-[(5-chloro-6-fluoro-1h-benzimidazol-2-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=NC2=CC(Cl)=C(F)C=C2N1 METQZGZXPFILTQ-UHFFFAOYSA-N 0.000 claims description 3
- YQJRXMSBSHRVKO-UHFFFAOYSA-N 2-[(6-chloro-1h-benzimidazol-2-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=NC2=CC(Cl)=CC=C2N1 YQJRXMSBSHRVKO-UHFFFAOYSA-N 0.000 claims description 3
- GQDTUUYOHPZKDP-UHFFFAOYSA-N 2-[4-(5-fluoro-2-methylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carbonitrile Chemical compound CC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C#N)=CC=C2N1 GQDTUUYOHPZKDP-UHFFFAOYSA-N 0.000 claims description 3
- WWEBXLJRICHTKV-UHFFFAOYSA-N 2-[[4-chloro-6-(trifluoromethyl)-1h-benzimidazol-2-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=NC2=CC(C(F)(F)F)=CC(Cl)=C2N1 WWEBXLJRICHTKV-UHFFFAOYSA-N 0.000 claims description 3
- QWKDBNYNXLXWAF-UHFFFAOYSA-N 2-[[6-chloro-4-(trifluoromethyl)pyridin-2-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(C(F)(F)F)=CC(Cl)=N1 QWKDBNYNXLXWAF-UHFFFAOYSA-N 0.000 claims description 3
- SDWHNRRHSCXODH-UHFFFAOYSA-N 4-(3-ethyl-2-methoxyphenyl)-1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound CCC1=CC=CC(C(C)(C)CC(O)(CC=2NC3=CC=CC=C3C=2)C(F)(F)F)=C1OC SDWHNRRHSCXODH-UHFFFAOYSA-N 0.000 claims description 3
- LRQZZRZVGAKDIB-UHFFFAOYSA-N 4-fluoro-2-[5,5,5-trifluoro-4-hydroxy-4-(isoquinolin-1-ylmethyl)-2-methylpentan-2-yl]phenol Chemical compound N=1C=CC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O LRQZZRZVGAKDIB-UHFFFAOYSA-N 0.000 claims description 3
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
- 208000019838 Blood disease Diseases 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 208000012659 Joint disease Diseases 0.000 claims description 3
- 208000019693 Lung disease Diseases 0.000 claims description 3
- 208000024447 adrenal gland neoplasm Diseases 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 208000030172 endocrine system disease Diseases 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 208000030533 eye disease Diseases 0.000 claims description 3
- 208000014951 hematologic disease Diseases 0.000 claims description 3
- 208000018706 hematopoietic system disease Diseases 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 208000017169 kidney disease Diseases 0.000 claims description 3
- 208000019423 liver disease Diseases 0.000 claims description 3
- JCAXAZOGOYLIFZ-UHFFFAOYSA-N methyl 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carboxylate Chemical compound C=1C2=CC(C(=O)OC)=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OC JCAXAZOGOYLIFZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 230000035939 shock Effects 0.000 claims description 3
- 230000003156 vasculitic effect Effects 0.000 claims description 3
- NNAQLJKWSWVSKP-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(7-fluoro-1h-indol-2-yl)methyl]-4-(3-fluorophenyl)-4-methylpentan-2-ol Chemical compound C=1C2=CC=CC(F)=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(F)=C1 NNAQLJKWSWVSKP-UHFFFAOYSA-N 0.000 claims description 2
- MJFBFGHCASVXDP-UHFFFAOYSA-N 1,1,1-trifluoro-4-(3-fluorophenyl)-4-methyl-2-[[5-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound C=1C2=CC(C(F)(F)F)=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(F)=C1 MJFBFGHCASVXDP-UHFFFAOYSA-N 0.000 claims description 2
- KGTZDLNZUPDLNN-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluoro-2-methylphenyl)-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound CC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC=C2N1 KGTZDLNZUPDLNN-UHFFFAOYSA-N 0.000 claims description 2
- DKDHDXLQHUNPRH-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluorophenyl)-4-methyl-2-[[5-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound C=1C2=CC(C(F)(F)F)=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 DKDHDXLQHUNPRH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- BWYPALCGFDZYRK-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-2-[(6-fluoro-4-methyl-1h-indol-2-yl)methyl]-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=C(C)C=C(F)C=C2N1 BWYPALCGFDZYRK-UHFFFAOYSA-N 0.000 claims description 2
- KUCGJKONRCMKSD-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-2-[(7-fluoro-4-methyl-1h-indol-2-yl)methyl]-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=C(C)C=CC(F)=C2N1 KUCGJKONRCMKSD-UHFFFAOYSA-N 0.000 claims description 2
- SMYUZCJLGBMSME-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(4-methyl-1h-indol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=C(C)C=CC=C2N1 SMYUZCJLGBMSME-UHFFFAOYSA-N 0.000 claims description 2
- ICUQBHIVWGFWAR-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-methyl-1h-indol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C)=CC=C2N1 ICUQBHIVWGFWAR-UHFFFAOYSA-N 0.000 claims description 2
- AXAIJGRNQQORMC-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(7-methyl-1h-indol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC(C)=C2N1 AXAIJGRNQQORMC-UHFFFAOYSA-N 0.000 claims description 2
- JJSZJRHRVRGDNH-UHFFFAOYSA-N 2-(benzimidazol-1-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)CN1C2=CC=CC=C2N=C1 JJSZJRHRVRGDNH-UHFFFAOYSA-N 0.000 claims description 2
- ZUEBHTRVRHRRGN-UHFFFAOYSA-N 2-[(4,6-dimethyl-1h-indol-2-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=CC2=C(C)C=C(C)C=C2N1 ZUEBHTRVRHRRGN-UHFFFAOYSA-N 0.000 claims description 2
- FESDGEMNPBYTJP-UHFFFAOYSA-N 2-[(6-chloro-4-methyl-1h-indol-2-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=CC2=C(C)C=C(Cl)C=C2N1 FESDGEMNPBYTJP-UHFFFAOYSA-N 0.000 claims description 2
- DVMOIBMNWXMHAV-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound C=1C=2C(C)=CC(C#N)=CC=2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCC2 DVMOIBMNWXMHAV-UHFFFAOYSA-N 0.000 claims description 2
- UIHNOUFKZHHJFI-UHFFFAOYSA-N 2-[5,5,5-trifluoro-4-hydroxy-4-(1h-indol-2-ylmethyl)-2-methylpentan-2-yl]naphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C(C)(CC(O)(CC=3NC4=CC=CC=C4C=3)C(F)(F)F)C)=CC=C21 UIHNOUFKZHHJFI-UHFFFAOYSA-N 0.000 claims description 2
- SGOZDXYRIAUTEY-UHFFFAOYSA-N 4-fluoro-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-[[5-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-yl]phenol Chemical compound C=1C2=CC(C(F)(F)F)=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O SGOZDXYRIAUTEY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- FGJBQPNVKINOAU-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound N1C2=CC=CC=C2C(C#N)=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCC2 FGJBQPNVKINOAU-UHFFFAOYSA-N 0.000 claims 4
- DMNBBFMQKWSMKA-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound N1C2=CC=CC=C2C(C#N)=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(F)=C1 DMNBBFMQKWSMKA-UHFFFAOYSA-N 0.000 claims 4
- VDIOFMJYOYVMOO-UHFFFAOYSA-N 2-[4-(4-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CC1=C(C#N)C2=CC=CC=C2N1 VDIOFMJYOYVMOO-UHFFFAOYSA-N 0.000 claims 4
- HKECIGWAKOKEQT-UHFFFAOYSA-N 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-n,n-dimethyl-1h-indole-5-carboxamide Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C(=O)N(C)C)=CC=C2N1 HKECIGWAKOKEQT-UHFFFAOYSA-N 0.000 claims 4
- LGGOQGCCYIYZRO-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-5-yl)-1,1,1-trifluoro-2-(1h-indol-2-ylmethyl)-4-methylpentan-2-ol Chemical compound C1=C2OCCC2=CC(C(C)(CC(O)(CC=2NC3=CC=CC=C3C=2)C(F)(F)F)C)=C1 LGGOQGCCYIYZRO-UHFFFAOYSA-N 0.000 claims 4
- JFUAWXPBHXKZGA-UHFFFAOYSA-N 4-fluoro-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C=1C2=CC=NC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O JFUAWXPBHXKZGA-UHFFFAOYSA-N 0.000 claims 4
- UCWWMUPWYRSGBY-UHFFFAOYSA-N 4-fluoro-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C=1C2=CN=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O UCWWMUPWYRSGBY-UHFFFAOYSA-N 0.000 claims 4
- HWFMMNOUTPEJKK-UHFFFAOYSA-N [2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indol-5-yl]-morpholin-4-ylmethanone Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C(=O)N3CCOCC3)=CC=C2N1 HWFMMNOUTPEJKK-UHFFFAOYSA-N 0.000 claims 4
- ANBHXCMGMQRMDH-UHFFFAOYSA-N 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]indole-3-carbonitrile Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2C(C#N)=C1 ANBHXCMGMQRMDH-UHFFFAOYSA-N 0.000 claims 3
- XVXPGVPWIBHGHC-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound N1C2=CC=CC=C2C(C#N)=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 XVXPGVPWIBHGHC-UHFFFAOYSA-N 0.000 claims 3
- HMVIXMZWCAEUSB-UHFFFAOYSA-N 2-[4-(5-fluoro-2,3-dihydro-1-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound N1C2=CC=CC=C2C(C#N)=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC2=C1OCC2 HMVIXMZWCAEUSB-UHFFFAOYSA-N 0.000 claims 3
- FAFXAGRBAMSJJF-UHFFFAOYSA-N 5-fluoro-2-[5,5,5-trifluoro-4-[(7-fluoro-1h-indol-2-yl)methyl]-4-hydroxy-2-methylpentan-2-yl]phenol Chemical compound C=1C2=CC=CC(F)=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1O FAFXAGRBAMSJJF-UHFFFAOYSA-N 0.000 claims 3
- GDYRGFVBOXXUOV-UHFFFAOYSA-N 5-fluoro-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C=1C2=CN=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1O GDYRGFVBOXXUOV-UHFFFAOYSA-N 0.000 claims 3
- ASLXDRZYYUJLPP-UHFFFAOYSA-N methyl 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-6-carboxylate Chemical compound N1C2=CC(C(=O)OC)=CC=C2C=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OC ASLXDRZYYUJLPP-UHFFFAOYSA-N 0.000 claims 3
- NAKVZBYNDIOTLA-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2,3-dihydro-1-benzofuran-7-yl)-4-methyl-2-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CC=NC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC2=C1OCC2 NAKVZBYNDIOTLA-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- JEQQYTQEYLRLQF-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(3-methyl-1-benzofuran-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=C(C)C2=CC=CC=C2O1 JEQQYTQEYLRLQF-UHFFFAOYSA-N 0.000 claims 2
- HGYBFMUSGUKXAE-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-phenyl-1,3-benzoxazol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NC2=CC(C=3C=CC=CC=3)=CC=C2O1 HGYBFMUSGUKXAE-UHFFFAOYSA-N 0.000 claims 2
- QWBADPWLMMOKQB-UHFFFAOYSA-N 2-(1-benzofuran-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=CC2=CC=CC=C2O1 QWBADPWLMMOKQB-UHFFFAOYSA-N 0.000 claims 2
- QXRBREJTACEPRH-UHFFFAOYSA-N 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-3-carbonitrile Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=C(C#N)C2=CC=CC=C2N1 QXRBREJTACEPRH-UHFFFAOYSA-N 0.000 claims 2
- UVNQTHIANKSLKK-UHFFFAOYSA-N 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-7-carbonitrile Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=CC(C#N)=C2N1 UVNQTHIANKSLKK-UHFFFAOYSA-N 0.000 claims 2
- AIPDSUAKVHJRJF-UHFFFAOYSA-N 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-4-methyl-1h-indole-6-carbonitrile Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=C(C)C=C(C#N)C=C2N1 AIPDSUAKVHJRJF-UHFFFAOYSA-N 0.000 claims 2
- LCYRIRNMUWKSLD-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-[[5-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound C=1C2=CC(C(F)(F)F)=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCC2 LCYRIRNMUWKSLD-UHFFFAOYSA-N 0.000 claims 2
- CYQHEACZISHSLN-UHFFFAOYSA-N 4-(5-bromo-2-methoxyphenyl)-1,1,1-trifluoro-4-methyl-2-[[5-(trifluoromethyl)-1h-indol-2-yl]methyl]pentan-2-ol Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C(F)(F)F)=CC=C2N1 CYQHEACZISHSLN-UHFFFAOYSA-N 0.000 claims 2
- MLNIORYTZANUHV-UHFFFAOYSA-N 5-fluoro-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C=1C2=CC=NC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1O MLNIORYTZANUHV-UHFFFAOYSA-N 0.000 claims 2
- YMUSTOVFCKGNHP-UHFFFAOYSA-N 6-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=C(C#N)C=N1 YMUSTOVFCKGNHP-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- VAKGPQCVNHUBLU-UHFFFAOYSA-N 1,1,1-trifluoro-2-(7-fluoro-4-methylquinolin-8-yl)-4-(4-fluorophenyl)-4-methylpentan-2-ol Chemical compound FC1=CC=C2C(C)=CC=NC2=C1C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 VAKGPQCVNHUBLU-UHFFFAOYSA-N 0.000 claims 1
- MHXGSAZAKQCFCR-UHFFFAOYSA-N 1,1,1-trifluoro-2-(quinolin-4-ylmethyl)-3-[1-[2-(trifluoromethoxy)phenyl]cyclopropyl]propan-2-ol Chemical compound C=1C=NC2=CC=CC=C2C=1CC(O)(C(F)(F)F)CC1(C=2C(=CC=CC=2)OC(F)(F)F)CC1 MHXGSAZAKQCFCR-UHFFFAOYSA-N 0.000 claims 1
- FLAQYRSYSGUXIZ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-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=C(F)C=C1 FLAQYRSYSGUXIZ-UHFFFAOYSA-N 0.000 claims 1
- ZYDGAZMITUNRQM-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(pyrazin-2-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CN=CC=N1 ZYDGAZMITUNRQM-UHFFFAOYSA-N 0.000 claims 1
- CVCYFBWQKVWBBB-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(pyridazin-3-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=CN=N1 CVCYFBWQKVWBBB-UHFFFAOYSA-N 0.000 claims 1
- LBLATFUXABORLM-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(pyridin-3-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=CN=C1 LBLATFUXABORLM-UHFFFAOYSA-N 0.000 claims 1
- DRUOALSKQUSRNH-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(pyrimidin-4-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=NC=N1 DRUOALSKQUSRNH-UHFFFAOYSA-N 0.000 claims 1
- HFZNNUVFBOLNEK-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(quinolin-2-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=C(C=CC=C2)C2=N1 HFZNNUVFBOLNEK-UHFFFAOYSA-N 0.000 claims 1
- SLMPSFHIYPUHEV-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(thiophen-2-ylmethyl)pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=CS1 SLMPSFHIYPUHEV-UHFFFAOYSA-N 0.000 claims 1
- IAZHBHTUFASNKI-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(1-methylimidazol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NC=CN1C IAZHBHTUFASNKI-UHFFFAOYSA-N 0.000 claims 1
- ZHWMCPUNVFPZJY-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(1-phenylpyrazol-3-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NN(C=2C=CC=CC=2)C=C1 ZHWMCPUNVFPZJY-UHFFFAOYSA-N 0.000 claims 1
- LDJGZEKJPVKHBO-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(3-methylpyridin-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NC=CC=C1C LDJGZEKJPVKHBO-UHFFFAOYSA-N 0.000 claims 1
- NSAGRVSYONUGJN-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(4-methylpyridin-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC(C)=CC=N1 NSAGRVSYONUGJN-UHFFFAOYSA-N 0.000 claims 1
- ZCVWFEIVPSIPCU-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(4-methylquinolin-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC(C)=C(C=CC=C2)C2=N1 ZCVWFEIVPSIPCU-UHFFFAOYSA-N 0.000 claims 1
- LZNQYGOSRHQXGG-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-methyl-1,3-benzothiazol-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NC2=CC(C)=CC=C2S1 LZNQYGOSRHQXGG-UHFFFAOYSA-N 0.000 claims 1
- YFLBQOLQVBWGMD-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(5-methylpyridin-3-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CN=CC(C)=C1 YFLBQOLQVBWGMD-UHFFFAOYSA-N 0.000 claims 1
- MSZOIWWALFRMNA-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(6-methylpyridin-2-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=CC(C)=N1 MSZOIWWALFRMNA-UHFFFAOYSA-N 0.000 claims 1
- HHEGQKQPIMPWII-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-phenyl-2-(pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C=CC=CC=1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=CC=N1 HHEGQKQPIMPWII-UHFFFAOYSA-N 0.000 claims 1
- BNAINDQSNRHQSP-UHFFFAOYSA-N 2-(1,3-benzothiazol-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=C2S1 BNAINDQSNRHQSP-UHFFFAOYSA-N 0.000 claims 1
- CGYARZVYHHRAAF-UHFFFAOYSA-N 2-(1,3-benzoxazol-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=C2O1 CGYARZVYHHRAAF-UHFFFAOYSA-N 0.000 claims 1
- WTWAMGSIUROHFB-UHFFFAOYSA-N 2-[(4,5-dimethyl-1,3-oxazol-2-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=NC(C)=C(C)O1 WTWAMGSIUROHFB-UHFFFAOYSA-N 0.000 claims 1
- DYHSSVVSIMVRNS-UHFFFAOYSA-N 2-[(4,5-dimethyl-1,3-thiazol-2-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=NC(C)=C(C)S1 DYHSSVVSIMVRNS-UHFFFAOYSA-N 0.000 claims 1
- JYSHRPNSKNFMIR-UHFFFAOYSA-N 2-[(4,6-dimethylpyridin-2-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(C)=CC(C)=N1 JYSHRPNSKNFMIR-UHFFFAOYSA-N 0.000 claims 1
- NLXARDIONINMQW-UHFFFAOYSA-N 2-[(4,6-dimethylpyridin-2-yl)methyl]-1,1,1-trifluoro-4-methyl-4-phenylpentan-2-ol Chemical compound CC1=CC(C)=NC(CC(O)(CC(C)(C)C=2C=CC=CC=2)C(F)(F)F)=C1 NLXARDIONINMQW-UHFFFAOYSA-N 0.000 claims 1
- DORQSUNHACTGLQ-UHFFFAOYSA-N 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carbonitrile Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C#N)=CC=C2N1 DORQSUNHACTGLQ-UHFFFAOYSA-N 0.000 claims 1
- ZAELWWZZEIHSRO-UHFFFAOYSA-N 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-3h-benzimidazole-5-carbonitrile Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=NC2=CC=C(C#N)C=C2N1 ZAELWWZZEIHSRO-UHFFFAOYSA-N 0.000 claims 1
- QBXCAMRAOGSUKN-UHFFFAOYSA-N 2-[[1-(2,5-difluorophenyl)cyclopropyl]methyl]-1,1,1-trifluoro-3-(1h-indol-2-yl)propan-2-ol Chemical compound C=1C2=CC=CC=C2NC=1CC(O)(C(F)(F)F)CC1(C=2C(=CC=C(F)C=2)F)CC1 QBXCAMRAOGSUKN-UHFFFAOYSA-N 0.000 claims 1
- SKMRYTFZHOJBSC-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C2=CN=CC=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCC2 SKMRYTFZHOJBSC-UHFFFAOYSA-N 0.000 claims 1
- HBFSVSJFVVLEAD-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,1,1-trifluoro-4-methyl-2-(pyridin-2-ylmethyl)pentan-2-ol Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)CC(O)(C(F)(F)F)CC1=CC=CC=N1 HBFSVSJFVVLEAD-UHFFFAOYSA-N 0.000 claims 1
- STLAXKKJJYYXHA-UHFFFAOYSA-N 4-fluoro-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-[(5-methyl-1,3-benzothiazol-2-yl)methyl]pentan-2-yl]phenol Chemical compound N=1C2=CC(C)=CC=C2SC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O STLAXKKJJYYXHA-UHFFFAOYSA-N 0.000 claims 1
- CVBHEORVTJZYAX-UHFFFAOYSA-N 4-fluoro-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-[(5-methyl-1,3-benzoxazol-2-yl)methyl]pentan-2-yl]phenol Chemical compound N=1C2=CC(C)=CC=C2OC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O CVBHEORVTJZYAX-UHFFFAOYSA-N 0.000 claims 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims 1
- CUOCLLZYYVCTNU-UHFFFAOYSA-N 5-(5-fluoro-2-methoxyphenyl)-5-methyl-2-pyridin-2-yl-3-(trifluoromethyl)hexan-3-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)C(C)C1=CC=CC=N1 CUOCLLZYYVCTNU-UHFFFAOYSA-N 0.000 claims 1
- SYOLGFCCFZBULZ-UHFFFAOYSA-N 5-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-n-methyl-3-phenyl-1,2-oxazole-4-carboxamide Chemical compound O1N=C(C=2C=CC=CC=2)C(C(=O)NC)=C1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OC SYOLGFCCFZBULZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 1
- 235000013405 beer Nutrition 0.000 claims 1
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims 1
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 claims 1
- 230000006870 function Effects 0.000 abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 239000000651 prodrug Substances 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 113
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 108
- 239000000243 solution Substances 0.000 description 92
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 45
- 210000004027 cell Anatomy 0.000 description 42
- 230000000694 effects Effects 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 39
- 235000002639 sodium chloride Nutrition 0.000 description 39
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 37
- 235000019341 magnesium sulphate Nutrition 0.000 description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 239000003921 oil Substances 0.000 description 33
- 235000019198 oils Nutrition 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 32
- 239000005557 antagonist Substances 0.000 description 29
- 239000012267 brine Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 29
- 229920006395 saturated elastomer Polymers 0.000 description 29
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
- 239000000741 silica gel Substances 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- 238000012360 testing method Methods 0.000 description 26
- 239000012044 organic layer Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 150000001721 carbon Chemical group 0.000 description 23
- 238000005259 measurement Methods 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 125000000217 alkyl group Chemical group 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 19
- 229960003957 dexamethasone Drugs 0.000 description 18
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 18
- 125000002950 monocyclic group Chemical group 0.000 description 18
- WKOKIMCPHGHWIF-UHFFFAOYSA-N pentan-2-ol Chemical compound C[CH]CC(C)O WKOKIMCPHGHWIF-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 229940037128 systemic glucocorticoids Drugs 0.000 description 16
- 239000010410 layer Substances 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 239000000556 agonist Substances 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 238000009739 binding Methods 0.000 description 14
- 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 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 230000027455 binding Effects 0.000 description 12
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical class [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 238000003556 assay Methods 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 11
- 102000003998 progesterone receptors Human genes 0.000 description 11
- 108090000468 progesterone receptors Proteins 0.000 description 11
- IWAOTAUGPGIVIN-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(=O)C(F)(F)F IWAOTAUGPGIVIN-UHFFFAOYSA-N 0.000 description 10
- 239000013543 active substance Substances 0.000 description 10
- 235000019270 ammonium chloride Nutrition 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 239000003826 tablet Substances 0.000 description 10
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000005909 Kieselgur Substances 0.000 description 9
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000004071 biological effect Effects 0.000 description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- 125000003367 polycyclic group Chemical group 0.000 description 9
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 230000003637 steroidlike Effects 0.000 description 9
- CHIFTAQVXHNVRW-UHFFFAOYSA-N 1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=CNC2=C1 CHIFTAQVXHNVRW-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 8
- 125000002619 bicyclic group Chemical group 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 210000002950 fibroblast Anatomy 0.000 description 8
- 230000006698 induction Effects 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 230000035903 transrepression Effects 0.000 description 8
- 230000001154 acute effect Effects 0.000 description 7
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 7
- 238000002875 fluorescence polarization Methods 0.000 description 7
- 230000014509 gene expression Effects 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 102000014654 Aromatase Human genes 0.000 description 6
- 108010078554 Aromatase Proteins 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 6
- 108090001005 Interleukin-6 Proteins 0.000 description 6
- 102000003979 Mineralocorticoid Receptors Human genes 0.000 description 6
- 108090000375 Mineralocorticoid Receptors Proteins 0.000 description 6
- 108010085012 Steroid Receptors Proteins 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- 229940099112 cornstarch Drugs 0.000 description 6
- 239000003246 corticosteroid Substances 0.000 description 6
- 229960001334 corticosteroids Drugs 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 210000003953 foreskin Anatomy 0.000 description 6
- 230000009229 glucose formation Effects 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 208000027866 inflammatory disease Diseases 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 description 6
- 229960003248 mifepristone Drugs 0.000 description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 102000005969 steroid hormone receptors Human genes 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WGTODYJZXSJIAG-UHFFFAOYSA-N tetramethylrhodamine chloride Chemical compound [Cl-].C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C(O)=O WGTODYJZXSJIAG-UHFFFAOYSA-N 0.000 description 6
- 108010002352 Interleukin-1 Proteins 0.000 description 5
- 241000713333 Mouse mammary tumor virus Species 0.000 description 5
- 102000016540 Tyrosine aminotransferases Human genes 0.000 description 5
- 108010042606 Tyrosine transaminase Proteins 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 125000005724 cycloalkenylene group Chemical group 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 201000008482 osteoarthritis Diseases 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 150000003431 steroids Chemical class 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 4
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical class OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Chemical class 0.000 description 4
- 102100040247 Tumor necrosis factor Human genes 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000002993 cycloalkylene group Chemical group 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 4
- 238000002405 diagnostic procedure Methods 0.000 description 4
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical class ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 4
- 229940043279 diisopropylamine Drugs 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229960005309 estradiol Drugs 0.000 description 4
- 229930182833 estradiol Natural products 0.000 description 4
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 208000026278 immune system disease Diseases 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000008101 lactose Chemical class 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 239000006166 lysate Substances 0.000 description 4
- 125000001979 organolithium group Chemical group 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 230000036961 partial effect Effects 0.000 description 4
- 125000004193 piperazinyl group Chemical group 0.000 description 4
- 125000003386 piperidinyl group Chemical group 0.000 description 4
- 239000013612 plasmid Substances 0.000 description 4
- 238000000159 protein binding assay Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 239000008107 starch Chemical class 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 229960003604 testosterone Drugs 0.000 description 4
- 125000003831 tetrazolyl group Chemical group 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 3
- TXYPEBKMDWRSAJ-UHFFFAOYSA-N 4-fluoro-2-[5,5,5-trifluoro-4-hydroxy-2-methyl-4-[(4-methyl-1h-indol-2-yl)methyl]pentan-2-yl]phenol Chemical compound C=1C=2C(C)=CC=CC=2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O TXYPEBKMDWRSAJ-UHFFFAOYSA-N 0.000 description 3
- UDWFSJAYXTXMLM-UHFFFAOYSA-N 5-bromo-2,3-dihydro-1-benzofuran Chemical compound BrC1=CC=C2OCCC2=C1 UDWFSJAYXTXMLM-UHFFFAOYSA-N 0.000 description 3
- 241000220479 Acacia Species 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 208000011231 Crohn disease Diseases 0.000 description 3
- 206010012442 Dermatitis contact Diseases 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 3
- 108090001007 Interleukin-8 Proteins 0.000 description 3
- 102000004890 Interleukin-8 Human genes 0.000 description 3
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
- 108060001084 Luciferase Proteins 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 201000009906 Meningitis Diseases 0.000 description 3
- 206010027476 Metastases Diseases 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 208000010247 contact dermatitis Diseases 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 3
- 229960001680 ibuprofen Drugs 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000028709 inflammatory response Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000017306 interleukin-6 production Effects 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000006199 nebulizer Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000004031 partial agonist Substances 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 239000013641 positive control Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000000552 rheumatic effect Effects 0.000 description 3
- 201000000306 sarcoidosis Diseases 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000015424 sodium Nutrition 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- HFWXCPFGOCGJDK-UHFFFAOYSA-N 1,1,1-trifluoro-2-[(5-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(F)=CC=C2N1 HFWXCPFGOCGJDK-UHFFFAOYSA-N 0.000 description 2
- NIMVTGRQESOYIJ-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluoro-2-methoxyphenyl)-4-methylpentan-2-one Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC(=O)C(F)(F)F NIMVTGRQESOYIJ-UHFFFAOYSA-N 0.000 description 2
- CVQNZRCLXBEQHH-UHFFFAOYSA-N 1,1,1-trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-one Chemical compound FC(F)(F)C(=O)CC(C)(C)C1=CC=C(F)C=C1 CVQNZRCLXBEQHH-UHFFFAOYSA-N 0.000 description 2
- NIJLKCTUHJTDTK-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-pyridin-2-ylpentan-2-ol Chemical compound FC(F)(F)C(O)CC(C)(C)C1=CC=CC=N1 NIJLKCTUHJTDTK-UHFFFAOYSA-N 0.000 description 2
- MNTDFXIXPXOKQV-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-pyridin-2-ylpentan-2-one Chemical compound FC(F)(F)C(=O)CC(C)(C)C1=CC=CC=N1 MNTDFXIXPXOKQV-UHFFFAOYSA-N 0.000 description 2
- MADVMHHBWSVUQF-UHFFFAOYSA-N 1,1,1-trifluoro-4-methylpent-3-en-2-one Chemical compound CC(C)=CC(=O)C(F)(F)F MADVMHHBWSVUQF-UHFFFAOYSA-N 0.000 description 2
- VNGQMLSLYDFRJX-UHFFFAOYSA-N 1,1,1-trifluoro-4-pyridin-2-ylbutan-2-ol Chemical compound FC(F)(F)C(O)CCC1=CC=CC=N1 VNGQMLSLYDFRJX-UHFFFAOYSA-N 0.000 description 2
- 150000000180 1,2-diols Chemical class 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 2
- YJMADHMYUJFMQE-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-amine Chemical compound NC1=CC=C2OCCC2=C1 YJMADHMYUJFMQE-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 2
- FTWPJQWUUXWKRT-UHFFFAOYSA-N 3,3,3-trifluoro-2-[[1-(5-fluoro-2-methoxyphenyl)cyclopropyl]methyl]propane-1,2-diol Chemical compound COC1=CC=C(F)C=C1C1(CC(O)(CO)C(F)(F)F)CC1 FTWPJQWUUXWKRT-UHFFFAOYSA-N 0.000 description 2
- GOKYGXMEVQWDSB-UHFFFAOYSA-N 3-(4-fluoro-2-methoxyphenyl)-3-methylbutanal Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC=O GOKYGXMEVQWDSB-UHFFFAOYSA-N 0.000 description 2
- SZIXKCOKIGPRBV-UHFFFAOYSA-N 3-(4-fluoro-2-methoxyphenyl)-3-methylbutanenitrile Chemical compound COC1=CC(F)=CC=C1C(C)(C)CC#N SZIXKCOKIGPRBV-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- BLYPSHVDSAPASP-UHFFFAOYSA-N 3-pyridin-2-ylpropanal Chemical compound O=CCCC1=CC=CC=N1 BLYPSHVDSAPASP-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- TYPKKUFDAHEIOP-UHFFFAOYSA-N 5-nitro-2,3-dihydro-1-benzofuran Chemical compound [O-][N+](=O)C1=CC=C2OCCC2=C1 TYPKKUFDAHEIOP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 208000026872 Addison Disease Diseases 0.000 description 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 206010002199 Anaphylactic shock Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 206010048962 Brain oedema Diseases 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- 208000000094 Chronic Pain Diseases 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 206010010356 Congenital anomaly Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 238000008157 ELISA kit Methods 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 2
- 229930182566 Gentamicin Natural products 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 2
- 206010051606 Necrotising colitis Diseases 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 206010037423 Pulmonary oedema Diseases 0.000 description 2
- 206010063837 Reperfusion injury Diseases 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- 206010039085 Rhinitis allergic Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 208000016247 Soft tissue disease Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 108700009124 Transcription Initiation Site Proteins 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 208000005298 acute pain Diseases 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 201000010105 allergic rhinitis Diseases 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 208000019664 bone resorption disease Diseases 0.000 description 2
- 208000006752 brain edema Diseases 0.000 description 2
- 229960001948 caffeine Drugs 0.000 description 2
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000023852 carbohydrate metabolic process Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000006037 cell lysis Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004296 chiral HPLC Methods 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 238000007887 coronary angioplasty Methods 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 102000015694 estrogen receptors Human genes 0.000 description 2
- 108010038795 estrogen receptors Proteins 0.000 description 2
- HGQBYZCLEZVTJO-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-[[1-(5-fluoro-2-methoxyphenyl)cyclopropyl]methyl]-2-hydroxypropanoate Chemical compound C=1C(F)=CC=C(OC)C=1C1(CC(O)(C(=O)OCC)C(F)(F)F)CC1 HGQBYZCLEZVTJO-UHFFFAOYSA-N 0.000 description 2
- DGTCAOIDDPQGPT-UHFFFAOYSA-N ethyl 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)pent-4-enoate Chemical compound CCOC(=O)C(O)(C(F)(F)F)CC(=C)C1=CC(F)=CC=C1OC DGTCAOIDDPQGPT-UHFFFAOYSA-N 0.000 description 2
- AXFJMVYMYLLDNO-UHFFFAOYSA-N ethyl 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoate Chemical compound CCOC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OC AXFJMVYMYLLDNO-UHFFFAOYSA-N 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000004129 fatty acid metabolism Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000012737 fresh medium Substances 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 210000003714 granulocyte Anatomy 0.000 description 2
- 238000001631 haemodialysis Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000000322 hemodialysis Effects 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 2
- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical class CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical group [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 229940071648 metered dose inhaler Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- JVMYUZGOJMWOAF-UHFFFAOYSA-N methyl 2-cyano-3-(4-fluoro-2-methoxyphenyl)-3-methylbutanoate Chemical compound COC(=O)C(C#N)C(C)(C)C1=CC=C(F)C=C1OC JVMYUZGOJMWOAF-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000002395 mineralocorticoid Substances 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 208000004995 necrotizing enterocolitis Diseases 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000007248 oxidative elimination reaction Methods 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229960001639 penicillamine Drugs 0.000 description 2
- 201000006195 perinatal necrotizing enterocolitis Diseases 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 201000006292 polyarteritis nodosa Diseases 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000022558 protein metabolic process Effects 0.000 description 2
- 208000005333 pulmonary edema Diseases 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229940107700 pyruvic acid Drugs 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical group [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- 239000000454 talc Chemical class 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- HSKHRZQJHMFPLZ-UHFFFAOYSA-N tert-butyl-dimethyl-(1,1,1-trifluoro-4-methyl-4-pyridin-2-ylpentan-2-yl)oxysilane Chemical compound CC(C)(C)[Si](C)(C)OC(C(F)(F)F)CC(C)(C)C1=CC=CC=N1 HSKHRZQJHMFPLZ-UHFFFAOYSA-N 0.000 description 2
- FBIGPRPVVRZJBP-UHFFFAOYSA-N tert-butyl-dimethyl-(1,1,1-trifluoro-4-pyridin-2-ylpentan-2-yl)oxysilane Chemical compound CC(C)(C)[Si](C)(C)OC(C(F)(F)F)CC(C)C1=CC=CC=N1 FBIGPRPVVRZJBP-UHFFFAOYSA-N 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 206010043778 thyroiditis Diseases 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 238000002424 x-ray crystallography Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- MQFKLCWETPKBCH-UHFFFAOYSA-N (3-fluoro-5-methoxyphenyl)boronic acid Chemical compound COC1=CC(F)=CC(B(O)O)=C1 MQFKLCWETPKBCH-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 1
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- WWMVTBBUANVHFD-UHFFFAOYSA-N 1,1,1-trifluoro-2-[[1-(5-fluoro-2-methoxyphenyl)cyclopropyl]methyl]-3-(1h-indol-2-yl)propan-2-ol Chemical compound COC1=CC=C(F)C=C1C1(CC(O)(CC=2NC3=CC=CC=C3C=2)C(F)(F)F)CC1 WWMVTBBUANVHFD-UHFFFAOYSA-N 0.000 description 1
- IXIRRHVGPUATCU-UHFFFAOYSA-N 1,1,1-trifluoro-3-[1-(4-fluorophenyl)cyclopropyl]propan-2-one Chemical compound C1=CC(F)=CC=C1C1(CC(=O)C(F)(F)F)CC1 IXIRRHVGPUATCU-UHFFFAOYSA-N 0.000 description 1
- COFBKORXGRCIBN-UHFFFAOYSA-N 1,1,1-trifluoro-3-[1-[2-(trifluoromethoxy)phenyl]cyclopropyl]propan-2-one Chemical compound FC(F)(F)OC1=CC=CC=C1C1(CC(=O)C(F)(F)F)CC1 COFBKORXGRCIBN-UHFFFAOYSA-N 0.000 description 1
- KEHBKJSUNCQGEB-UHFFFAOYSA-N 1,1,1-trifluoro-4-(1-methoxynaphthalen-2-yl)-4-methylpentan-2-one Chemical compound C1=CC=C2C(OC)=C(C(C)(C)CC(=O)C(F)(F)F)C=CC2=C1 KEHBKJSUNCQGEB-UHFFFAOYSA-N 0.000 description 1
- XLRDEYDUDYBJBH-UHFFFAOYSA-N 1,1,1-trifluoro-4-(3-methoxyphenyl)-4-methylpentan-2-one Chemical compound COC1=CC=CC(C(C)(C)CC(=O)C(F)(F)F)=C1 XLRDEYDUDYBJBH-UHFFFAOYSA-N 0.000 description 1
- GPADRZXMFHEAOA-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2,3-dihydro-1-benzofuran-7-yl)-4-methylpentan-2-one Chemical compound FC(F)(F)C(=O)CC(C)(C)C1=CC(F)=CC2=C1OCC2 GPADRZXMFHEAOA-UHFFFAOYSA-N 0.000 description 1
- UQHUARJVUFCJHO-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-(5-methyl-2,3-dihydro-1-benzofuran-7-yl)pentan-2-one Chemical compound FC(F)(F)C(=O)CC(C)(C)C1=CC(C)=CC2=C1OCC2 UQHUARJVUFCJHO-UHFFFAOYSA-N 0.000 description 1
- MLNQNUVPNBYQKL-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-[3-(trifluoromethyl)phenyl]pentan-2-one Chemical compound FC(F)(F)C(=O)CC(C)(C)C1=CC=CC(C(F)(F)F)=C1 MLNQNUVPNBYQKL-UHFFFAOYSA-N 0.000 description 1
- QAFGQCHGVPVDCZ-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-4-naphthalen-2-ylpentan-2-one Chemical compound C1=CC=CC2=CC(C(C)(CC(=O)C(F)(F)F)C)=CC=C21 QAFGQCHGVPVDCZ-UHFFFAOYSA-N 0.000 description 1
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical class CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- MEMYAJNODSYPGC-UHFFFAOYSA-N 1,3-dichlorocyclobutane Chemical compound ClC1CC(Cl)C1 MEMYAJNODSYPGC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YOXBPWVWNQROBJ-UHFFFAOYSA-N 1-(4-fluoro-2-methoxyphenyl)ethanone Chemical compound COC1=CC(F)=CC=C1C(C)=O YOXBPWVWNQROBJ-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- DEFNUDNHTUZJAL-UHFFFAOYSA-N 1-bromo-2-methylprop-1-ene Chemical compound CC(C)=CBr DEFNUDNHTUZJAL-UHFFFAOYSA-N 0.000 description 1
- FNVMKIIACPAWOH-UHFFFAOYSA-N 1-bromoprop-2-ynyl(trimethyl)silane Chemical compound C[Si](C)(C)C(Br)C#C FNVMKIIACPAWOH-UHFFFAOYSA-N 0.000 description 1
- VIPWUFMFHBIKQI-UHFFFAOYSA-N 1-fluoro-4-methoxybenzene Chemical compound COC1=CC=C(F)C=C1 VIPWUFMFHBIKQI-UHFFFAOYSA-N 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- YGBXXWTZWLALGR-UHFFFAOYSA-N 2,3-Dimethylbenzofuran Chemical compound C1=CC=C2C(C)=C(C)OC2=C1 YGBXXWTZWLALGR-UHFFFAOYSA-N 0.000 description 1
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 description 1
- GBGPVUAOTCNZPT-UHFFFAOYSA-N 2-Methylcumarone Chemical compound C1=CC=C2OC(C)=CC2=C1 GBGPVUAOTCNZPT-UHFFFAOYSA-N 0.000 description 1
- XFTQHXCONPZFRK-UHFFFAOYSA-N 2-[(5-chloro-7-fluoro-1h-indol-2-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=CC2=CC(Cl)=CC(F)=C2N1 XFTQHXCONPZFRK-UHFFFAOYSA-N 0.000 description 1
- SZKAYVKGAZWCHZ-UHFFFAOYSA-N 2-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-5-carbonitrile Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC(C#N)=CC=C2N1 SZKAYVKGAZWCHZ-UHFFFAOYSA-N 0.000 description 1
- APFRIAPSFXIGNM-UHFFFAOYSA-N 2-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-6-carboxylic acid Chemical compound C=1C2=CC=C(C(O)=O)C=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O APFRIAPSFXIGNM-UHFFFAOYSA-N 0.000 description 1
- WHRGIYXHZXRJFX-UHFFFAOYSA-N 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1h-indole-6-carboxylic acid Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC1=CC2=CC=C(C(O)=O)C=C2N1 WHRGIYXHZXRJFX-UHFFFAOYSA-N 0.000 description 1
- LDRYBABUAMXCLX-UHFFFAOYSA-N 2-[4-[(4,5-difluoro-1h-benzimidazol-2-yl)methyl]-5,5,5-trifluoro-4-hydroxy-2-methylpentan-2-yl]-4-fluorophenol Chemical compound N=1C2=CC=C(F)C(F)=C2NC=1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O LDRYBABUAMXCLX-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- LUPQCAARZVEFMT-UHFFFAOYSA-N 2-bromoprop-2-enyl(trimethyl)silane Chemical compound C[Si](C)(C)CC(Br)=C LUPQCAARZVEFMT-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- QKRMFCXDTFLKKT-UHFFFAOYSA-N 2-hydroxyethanesulfonic acid Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O QKRMFCXDTFLKKT-UHFFFAOYSA-N 0.000 description 1
- CHZDPBVCBBQQRP-UHFFFAOYSA-N 2-methyl-5-phenyl-1,3-benzoxazole Chemical compound C=1C=C2OC(C)=NC2=CC=1C1=CC=CC=C1 CHZDPBVCBBQQRP-UHFFFAOYSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-L 2-oxoglutarate(2-) Chemical compound [O-]C(=O)CCC(=O)C([O-])=O KPGXRSRHYNQIFN-UHFFFAOYSA-L 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- JRIDNJRPMHCUMK-UHFFFAOYSA-N 3,3,3-triphenylpropanamide Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(CC(=O)N)C1=CC=CC=C1 JRIDNJRPMHCUMK-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- UMCMPZBLKLEWAF-BCTGSCMUSA-N 3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 UMCMPZBLKLEWAF-BCTGSCMUSA-N 0.000 description 1
- RHFBDHYGXPNMIF-UHFFFAOYSA-N 3-[1-(2,5-difluorophenyl)cyclopropyl]-1,1,1-trifluoropropan-2-one Chemical compound FC1=CC=C(F)C(C2(CC(=O)C(F)(F)F)CC2)=C1 RHFBDHYGXPNMIF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PZVZGDBCMQBRMA-UHFFFAOYSA-N 3-pyridin-4-ylpropan-1-ol Chemical compound OCCCC1=CC=NC=C1 PZVZGDBCMQBRMA-UHFFFAOYSA-N 0.000 description 1
- ZBFKMZVKDHJDCX-UHFFFAOYSA-N 4-(3,5-dimethoxyphenyl)-1,1,1-trifluoro-4-methylpentan-2-one Chemical compound COC1=CC(OC)=CC(C(C)(C)CC(=O)C(F)(F)F)=C1 ZBFKMZVKDHJDCX-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FHVKKMBQYRKMHT-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,1,1-trifluoro-4-methylpentan-2-one Chemical compound FC(F)(F)C(=O)CC(C)(C)C1=CC=C(Cl)C=C1 FHVKKMBQYRKMHT-UHFFFAOYSA-N 0.000 description 1
- MJQCRZFXQWLGFJ-UHFFFAOYSA-N 4-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one Chemical compound FC(F)(F)C(=O)CC(C)(C)C1=CC(Br)=CC2=C1OCC2 MJQCRZFXQWLGFJ-UHFFFAOYSA-N 0.000 description 1
- DTDUCWHRYUZKBH-UHFFFAOYSA-N 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(CO)C(F)(F)F DTDUCWHRYUZKBH-UHFFFAOYSA-N 0.000 description 1
- ZHWNUQPXXSPXLX-UHFFFAOYSA-N 4-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)-1,1,1-trifluoro-4-methylpentan-2-one Chemical compound BrC1=CC(C(C)(CC(=O)C(F)(F)F)C)=CC2=C1OCC2 ZHWNUQPXXSPXLX-UHFFFAOYSA-N 0.000 description 1
- XDKGMGJZRFOZRV-UHFFFAOYSA-N 4-(bromomethyl)-2,6-dichloropyridine Chemical compound ClC1=CC(CBr)=CC(Cl)=N1 XDKGMGJZRFOZRV-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- PAVTXINZFWRQOD-UHFFFAOYSA-N 5-fluoro-2,3-dihydro-1-benzofuran Chemical compound FC1=CC=C2OCCC2=C1 PAVTXINZFWRQOD-UHFFFAOYSA-N 0.000 description 1
- OLHBKXYPKCHVNW-UHFFFAOYSA-N 5-methyl-2,3-dihydro-1-benzofuran Chemical compound CC1=CC=C2OCCC2=C1 OLHBKXYPKCHVNW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- 208000005676 Adrenogenital syndrome Diseases 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 206010057380 Allergic keratitis Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical class O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
- 206010001889 Alveolitis Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 206010003267 Arthritis reactive Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004364 Benzylated hydrocarbon Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 206010006417 Bronchial carcinoma Diseases 0.000 description 1
- 206010006811 Bursitis Diseases 0.000 description 1
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 1
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000002691 Choroiditis Diseases 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 208000015943 Coeliac disease Diseases 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 1
- 208000014311 Cushing syndrome Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 230000004568 DNA-binding Effects 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012441 Dermatitis bullous Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 206010060742 Endocrine ophthalmopathy Diseases 0.000 description 1
- 206010015218 Erythema multiforme Diseases 0.000 description 1
- 206010015226 Erythema nodosum Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000920033 Eugenes Species 0.000 description 1
- 208000028387 Felty syndrome Diseases 0.000 description 1
- 208000036119 Frailty Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 208000005577 Gastroenteritis Diseases 0.000 description 1
- 108700039691 Genetic Promoter Regions Proteins 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 229940123037 Glucocorticoid antagonist Drugs 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 206010018498 Goitre Diseases 0.000 description 1
- 208000003807 Graves Disease Diseases 0.000 description 1
- 208000015023 Graves' disease Diseases 0.000 description 1
- 208000001204 Hashimoto Disease Diseases 0.000 description 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 101000926939 Homo sapiens Glucocorticoid receptor Proteins 0.000 description 1
- 101001055222 Homo sapiens Interleukin-8 Proteins 0.000 description 1
- 101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
- 206010021750 Infantile Spasms Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 208000029523 Interstitial Lung disease Diseases 0.000 description 1
- 208000003456 Juvenile Arthritis Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- 239000005089 Luciferase Substances 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 229920000881 Modified starch Chemical class 0.000 description 1
- 208000010428 Muscle Weakness Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 108010057466 NF-kappa B Proteins 0.000 description 1
- 102000003945 NF-kappa B Human genes 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 208000011623 Obstructive Lung disease Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 208000003435 Optic Neuritis Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- 206010033078 Otitis media Diseases 0.000 description 1
- 201000011152 Pemphigus Diseases 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 241001307210 Pene Species 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
- 201000005746 Pituitary adenoma Diseases 0.000 description 1
- 206010061538 Pituitary tumour benign Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000007048 Polymyalgia Rheumatica Diseases 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000003971 Posterior uveitis Diseases 0.000 description 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
- 206010036774 Proctitis Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 206010037765 Radiation pneumonitis Diseases 0.000 description 1
- 108091027981 Response element Proteins 0.000 description 1
- 208000030934 Restrictive pulmonary disease Diseases 0.000 description 1
- 241001303601 Rosacea Species 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
- 206010039807 Secondary adrenocortical insufficiency Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 206010042742 Sympathetic ophthalmia Diseases 0.000 description 1
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 1
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000000491 Tendinopathy Diseases 0.000 description 1
- 206010043255 Tendonitis Diseases 0.000 description 1
- 201000002015 Thyroid Crisis Diseases 0.000 description 1
- 206010043786 Thyrotoxic crisis Diseases 0.000 description 1
- 108010018242 Transcription Factor AP-1 Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102100023118 Transcription factor JunD Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 206010048873 Traumatic arthritis Diseases 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 208000021017 Weight Gain Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229910001115 Zinc-copper couple Inorganic materials 0.000 description 1
- 239000003655 absorption accelerator Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 231100000354 acute hepatitis Toxicity 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229960000250 adipic acid Drugs 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 208000004631 alopecia areata Diseases 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 102000001307 androgen receptors Human genes 0.000 description 1
- 108010080146 androgen receptors Proteins 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 230000000947 anti-immunosuppressive effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001399 anti-metabolic effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 206010003230 arteritis Diseases 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
- 208000002479 balanitis Diseases 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000035587 bioadhesion Effects 0.000 description 1
- 239000004305 biphenyl Chemical group 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 208000010217 blepharitis Diseases 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000003914 blood derivative Substances 0.000 description 1
- 230000009045 body homeostasis Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 201000009267 bronchiectasis Diseases 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 208000003362 bronchogenic carcinoma Diseases 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229920003086 cellulose ether Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000005557 chiral recognition Methods 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000009137 competitive binding Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
- 229960000258 corticotropin Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000009260 cross reactivity Effects 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000005725 cyclohexenylene group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000002074 deregulated effect Effects 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- OUJRZMYAWPFRSV-UHFFFAOYSA-N ethyl 2-hydroxy-4-methyl-2-(trifluoromethyl)pent-4-enoate Chemical compound CCOC(=O)C(O)(C(F)(F)F)CC(C)=C OUJRZMYAWPFRSV-UHFFFAOYSA-N 0.000 description 1
- KJHQVUNUOIEYSV-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-oxopropanoate Chemical compound CCOC(=O)C(=O)C(F)(F)F KJHQVUNUOIEYSV-UHFFFAOYSA-N 0.000 description 1
- RDPQDILTDWPYDD-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-2-oxobutanoate Chemical compound CCOC(=O)C(=O)CC(F)(F)F RDPQDILTDWPYDD-UHFFFAOYSA-N 0.000 description 1
- XTEGTICBBDTCEO-UHFFFAOYSA-N ethyl 4-bromo-2-hydroxy-2-(trifluoromethyl)pent-4-enoate Chemical compound CCOC(=O)C(O)(C(F)(F)F)CC(Br)=C XTEGTICBBDTCEO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000013604 expression vector Substances 0.000 description 1
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003635 glucocorticoid antagonist Substances 0.000 description 1
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 description 1
- 230000004110 gluconeogenesis Effects 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 201000003872 goiter Diseases 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- 208000007475 hemolytic anemia Diseases 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- UKACHOXRXFQJFN-UHFFFAOYSA-N heptafluoropropane Chemical compound FC(F)C(F)(F)C(F)(F)F UKACHOXRXFQJFN-UHFFFAOYSA-N 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000006028 immune-suppresssive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000021995 interleukin-8 production Effects 0.000 description 1
- 102000027411 intracellular receptors Human genes 0.000 description 1
- 108091008582 intracellular receptors Proteins 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 201000004614 iritis Diseases 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 201000004990 juvenile ankylosing spondylitis Diseases 0.000 description 1
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 1
- 208000025036 lymphosarcoma Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- FFUIUNZKXBJVSC-UHFFFAOYSA-M magnesium;2-methylprop-1-ene;bromide Chemical compound [Mg+2].[Br-].CC(C)=[CH-] FFUIUNZKXBJVSC-UHFFFAOYSA-M 0.000 description 1
- BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical group COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- FROUTVVQOQLALX-UHFFFAOYSA-N methyl 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]indole-3-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OC)=CN1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OC FROUTVVQOQLALX-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 208000037890 multiple organ injury Diseases 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 208000028931 non-acquired combined pituitary hormone deficiency Diseases 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 125000005593 norbornanyl group Chemical group 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 231100001143 noxa Toxicity 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- QHGUCRYDKWKLMG-UHFFFAOYSA-N octopamine Chemical compound NCC(O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-UHFFFAOYSA-N 0.000 description 1
- 229960001576 octopamine Drugs 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000008816 organ damage Effects 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000000963 osteoblast Anatomy 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229920003175 pectinic acid Polymers 0.000 description 1
- 201000001976 pemphigus vulgaris Diseases 0.000 description 1
- 208000000689 peptic esophagitis Diseases 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229930029653 phosphoenolpyruvate Natural products 0.000 description 1
- DTBNBXWJWCWCIK-UHFFFAOYSA-N phosphoenolpyruvic acid Chemical compound OC(=O)C(=C)OP(O)(O)=O DTBNBXWJWCWCIK-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 208000021310 pituitary gland adenoma Diseases 0.000 description 1
- 206010035116 pityriasis rubra pilaris Diseases 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- 230000000757 progestagenic effect Effects 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- RNTLGNBDNIPFCO-UHFFFAOYSA-N prop-2-ynylaluminum Chemical compound [Al]CC#C RNTLGNBDNIPFCO-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 210000003370 receptor cell Anatomy 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000003938 response to stress Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 208000023087 secondary adrenal insufficiency Diseases 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical class O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000011301 standard therapy Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FUKNUVWILSPUSJ-UHFFFAOYSA-N tert-butyl n-(4-iodopyridin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CN=CC=C1I FUKNUVWILSPUSJ-UHFFFAOYSA-N 0.000 description 1
- RWIJHMNTPYNDIB-UHFFFAOYSA-N tert-butyl n-[4-[6-(5-fluoro-2-methoxyphenyl)-4-hydroxy-6-methyl-4-(trifluoromethyl)hept-1-ynyl]pyridin-3-yl]carbamate Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CC#CC1=CC=NC=C1NC(=O)OC(C)(C)C RWIJHMNTPYNDIB-UHFFFAOYSA-N 0.000 description 1
- VPQQCEAKWJTCFK-UHFFFAOYSA-N tert-butyl-dimethyl-(1,1,1-trifluoro-4-pyridin-2-ylbutan-2-yl)oxysilane Chemical compound CC(C)(C)[Si](C)(C)OC(C(F)(F)F)CCC1=CC=CC=N1 VPQQCEAKWJTCFK-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229960000257 tiotropium bromide Drugs 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 208000002003 vulvitis Diseases 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- C07D233/64—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 with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Transplantation (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US36775802P | 2002-03-26 | 2002-03-26 | |
US43181702P | 2002-12-09 | 2002-12-09 | |
US44240403P | 2003-01-24 | 2003-01-24 | |
PCT/US2003/008901 WO2003082280A1 (en) | 2002-03-26 | 2003-03-21 | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20044031L NO20044031L (no) | 2004-10-19 |
NO329386B1 true NO329386B1 (no) | 2010-10-11 |
Family
ID=28678922
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20044031A NO329386B1 (no) | 2002-03-26 | 2004-09-24 | Glukocorticoid-mimetica, farmasoytiske preparater og anvendelser for fremstilling av medikamenterfor behandling av sykdom |
NO20100827A NO20100827L (no) | 2002-03-26 | 2010-06-10 | Glukocorticoid-mimetica, fremgangsmater for fremstilling av dem, farmasoytiske blandinger, og anvendelser derav |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20100827A NO20100827L (no) | 2002-03-26 | 2010-06-10 | Glukocorticoid-mimetica, fremgangsmater for fremstilling av dem, farmasoytiske blandinger, og anvendelser derav |
Country Status (33)
Country | Link |
---|---|
US (4) | US6903215B2 (zh) |
EP (1) | EP1490062B1 (zh) |
JP (1) | JP4324480B2 (zh) |
KR (1) | KR101022977B1 (zh) |
CN (1) | CN1633296A (zh) |
AR (1) | AR039140A1 (zh) |
AT (1) | ATE381333T1 (zh) |
AU (1) | AU2003218342B8 (zh) |
BR (1) | BR0308784A (zh) |
CA (1) | CA2478156C (zh) |
CL (1) | CL2010000375A1 (zh) |
CO (1) | CO5611110A2 (zh) |
CY (1) | CY1107244T1 (zh) |
DE (1) | DE60318188T2 (zh) |
DK (1) | DK1490062T3 (zh) |
EA (1) | EA008830B1 (zh) |
EC (1) | ECSP045315A (zh) |
ES (1) | ES2298508T3 (zh) |
HR (1) | HRP20040887A2 (zh) |
IL (1) | IL163366A (zh) |
MX (1) | MXPA04009329A (zh) |
NO (2) | NO329386B1 (zh) |
NZ (1) | NZ535889A (zh) |
PE (1) | PE20040164A1 (zh) |
PL (1) | PL373043A1 (zh) |
PT (1) | PT1490062E (zh) |
RS (1) | RS51097B (zh) |
SA (3) | SA07280239B1 (zh) |
TW (1) | TWI326213B (zh) |
UA (1) | UA80120C2 (zh) |
UY (1) | UY27736A1 (zh) |
WO (1) | WO2003082280A1 (zh) |
ZA (1) | ZA200406225B (zh) |
Families Citing this family (173)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003059899A1 (en) * | 2002-01-14 | 2003-07-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof |
NZ535889A (en) * | 2002-03-26 | 2006-03-31 | Boehringer Ingelheim Pharma | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
JP2005521717A (ja) * | 2002-03-26 | 2005-07-21 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | グルココルチコイドミメチックス、その製造方法、その医薬組成物、及び使用 |
US7186864B2 (en) * | 2002-05-29 | 2007-03-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
US7074806B2 (en) * | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
JP2006504678A (ja) | 2002-08-21 | 2006-02-09 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | グルココルチコイドミメチックス、その製造方法、その医薬組成物、及び使用 |
JP4619786B2 (ja) * | 2002-08-29 | 2011-01-26 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 炎症性、アレルギー性及び増殖性疾患の治療において糖質コルチコイドミメティックスとして使用するための3−(スルホンアミドエチル)−インドール誘導体 |
WO2004063163A1 (en) * | 2003-01-03 | 2004-07-29 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1-propanol and 1-propylamine derivatives and their use as glucocorticoid ligands |
AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
GB0316290D0 (en) | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Novel compounds |
UY28526A1 (es) * | 2003-09-24 | 2005-04-29 | Boehringer Ingelheim Pharma | Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos |
WO2005034939A1 (de) | 2003-10-08 | 2005-04-21 | Schering Aktiengesellschaft | Tetrahydronaphthalinderivate, verfahren zu ihrer herstellung und ihre verwendung als entzündungshemmer |
US7662821B2 (en) | 2003-10-08 | 2010-02-16 | Bayer Schering Pharma Ag | Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
US7638515B2 (en) | 2003-10-08 | 2009-12-29 | Bayer Schering Pharma Aktiengesellschaft | Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
US7795272B2 (en) * | 2004-03-13 | 2010-09-14 | Boehringer Ingelheim Pharmaceutical, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof |
US7179919B2 (en) * | 2004-03-18 | 2007-02-20 | Boehringer Ingelheim Pharmaceuticals, Inc. | Stereoselective synthesis of certain trifluoromethyl-substituted alcohols |
EP1730145A1 (en) * | 2004-03-22 | 2006-12-13 | Boehringer Ingelheim Pharmaceuticals Inc. | Alpha-trifluoromethyl alcohols or amines as glucocorticoid mimetics |
WO2005097162A2 (en) * | 2004-04-01 | 2005-10-20 | Elan Pharmaceuticals, Inc. | Steroid sparing agents and their use |
US20080153859A1 (en) | 2004-04-05 | 2008-06-26 | Hartmut Rehwinkel | Multiply-substituted tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
WO2005110985A2 (en) | 2004-05-03 | 2005-11-24 | Janssen Pharmaceutica N.V. | Indole, benzofuran and benzothiophene derivatives as selective androgen receptor modulators (sarms) |
GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
DE102004025791A1 (de) * | 2004-05-19 | 2005-12-15 | Schering Ag | Chromanol-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
AR049384A1 (es) | 2004-05-24 | 2006-07-26 | Glaxo Group Ltd | Derivados de purina |
TWI307630B (en) | 2004-07-01 | 2009-03-21 | Glaxo Group Ltd | Immunoglobulins |
US20070293532A1 (en) | 2004-07-28 | 2007-12-20 | Takeda Pharmaceutical Compan6Y Limited | Pyrrolo [2,3-C] Pyridine Compound, Process for Producing the Same, and Use |
US20060030608A1 (en) * | 2004-08-04 | 2006-02-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti aromatase compounds pharmaceutical compositions and uses thereof |
GB0418045D0 (en) | 2004-08-12 | 2004-09-15 | Glaxo Group Ltd | Compounds |
DE102004044680B3 (de) * | 2004-09-09 | 2006-06-08 | Schering Ag | Alkyliden-Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer sowie diese enthaltende pharmazeutische Präparate |
GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
DE102005020331A1 (de) * | 2005-04-26 | 2006-11-02 | Schering Ag | 5-substituierte Chinolin- und Isochinolin-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
DE102004063227A1 (de) * | 2004-12-22 | 2006-07-06 | Schering Ag | Tricylische Aminoalkohole, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
PE20060776A1 (es) * | 2004-12-27 | 2006-09-26 | Boehringer Ingelheim Pharma | Mimeticos de glucocorticoides, metodos para prepararlos y composiciones farmaceuticas |
JP5281291B2 (ja) | 2005-01-10 | 2013-09-04 | グラクソ グループ リミテッド | 新規化合物 |
US20090176807A1 (en) * | 2005-03-04 | 2009-07-09 | John Robinson Regan | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
AR053450A1 (es) | 2005-03-25 | 2007-05-09 | Glaxo Group Ltd | Derivados de 3,4-dihidro-pirimido(4,5-d)pirimidin-2-(1h)-ona 1,5,7 trisustituidos como inhibidores de la quinasa p38 |
PE20100737A1 (es) | 2005-03-25 | 2010-11-27 | Glaxo Group Ltd | Nuevos compuestos |
GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
WO2006108699A1 (en) * | 2005-04-14 | 2006-10-19 | Glaxo Group Limited | Indazoles as glucocorticoid receptor ligands |
GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
WO2006135826A1 (en) * | 2005-06-10 | 2006-12-21 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
GB0514809D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
US20100190768A1 (en) * | 2005-09-30 | 2010-07-29 | Dainippon Sumitomo Pharma Co., Ltd. | Novel fused pyrole derivative |
EP1934218B1 (en) | 2005-09-30 | 2009-11-18 | Boehringer Ingelheim International GmbH | Stereoselective synthesis of certain trifluoromethyl-substituted alcohols |
KR20080049113A (ko) | 2005-10-21 | 2008-06-03 | 노파르티스 아게 | Il-13에 대항한 인간 항체 및 치료적 용도 |
KR101025139B1 (ko) * | 2005-12-09 | 2011-03-31 | 에프. 호프만-라 로슈 아게 | 항염증제로서의 프로피온아미드 화합물 |
BRPI0619518A2 (pt) * | 2005-12-09 | 2011-10-11 | Hoffmann La Roche | moduladores do receptor de glicocorticoide, composição farmacêutica que os compreende e usos dos mesmos |
TW200730498A (en) | 2005-12-20 | 2007-08-16 | Glaxo Group Ltd | Compounds |
GB0526244D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
EP1834948A1 (de) | 2006-03-15 | 2007-09-19 | Bayer Schering Pharma Aktiengesellschaft | Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
AU2007242851A1 (en) | 2006-04-20 | 2007-11-01 | Glaxo Group Limited | Novel compounds |
SI2013211T1 (sl) | 2006-04-21 | 2012-07-31 | Novartis Ag | Purinski derivati za uporabo kot agonisti receptorja adenozina A A |
GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
JP2009542704A (ja) * | 2006-07-07 | 2009-12-03 | ボーシュ アンド ローム インコーポレイティド | ドライ・アイを治療するための医薬組成物と方法 |
EP2049112B1 (en) * | 2006-08-07 | 2012-03-14 | Bausch & Lomb Incorporated | Treating infections and sequelae thereof with combined dissociated glucocorticoid receptor agonists and anti-infective agents |
KR20090050091A (ko) * | 2006-08-31 | 2009-05-19 | 보오슈 앤드 롬 인코포레이팃드 | 녹내장 또는 그의 진행을 치료 또는 예방하기 위한 조성물 및 방법 |
US20110104159A1 (en) * | 2006-09-11 | 2011-05-05 | Rohrs Brian R | Compositions and methods for treating, controlling, reducing, ameliorating, or preventing allergy |
ES2361585T3 (es) * | 2006-09-11 | 2011-06-20 | BAUSCH & LOMB INCORPORATED | Composiciones y métodos para tratar, controlar, reducir, mejorar o prevenir la alergia. |
US20110105559A1 (en) * | 2006-09-11 | 2011-05-05 | Rohrs Brian R | Compositions and Methods for Treating, Controlling, Reducing, Ameliorating, or Preventing Allergy |
ATE502943T1 (de) | 2006-09-29 | 2011-04-15 | Novartis Ag | Pyrazolopyrimidine als pi3k-lipidkinasehemmer |
WO2008055709A1 (en) * | 2006-11-08 | 2008-05-15 | Bayer Schering Pharma Aktiengesellschaft | Indazole and indole derivatives as anti -inflammatory agents |
EP1921067A1 (en) * | 2006-11-08 | 2008-05-14 | Bayer Schering Pharma Aktiengesellschaft | Indole and indazole derivatives as anti-inflammatory agents |
EP1921068A1 (en) * | 2006-11-08 | 2008-05-14 | Bayer Schering Pharma Aktiengesellschaft | Indazole and indole derivatives as anti-inflammatory agents |
JP2010512331A (ja) * | 2006-12-06 | 2010-04-22 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | グルココルチコイド模倣薬、それらの製造方法、医薬組成物、及びこれらの使用 |
DK2104535T3 (da) | 2007-01-10 | 2011-04-04 | Irm Llc | Forbindelser og sammensætninger som kanalaktiverende proteaseinhibitorer |
AR065804A1 (es) | 2007-03-23 | 2009-07-01 | Smithkline Beecham Corp | Compuesto de indol carboxamida, composicion farmaceutica que lo comprende y uso de dicho compuesto para preparar un medicamento |
JP5244904B2 (ja) | 2007-05-07 | 2013-07-24 | ノバルティス アーゲー | 有機化合物 |
US20090042936A1 (en) * | 2007-08-10 | 2009-02-12 | Ward Keith W | Compositions and Methods for Treating or Controlling Anterior-Segment Inflammation |
US9254275B2 (en) * | 2007-09-17 | 2016-02-09 | Cornell University | Branched chain fatty acids for prevention or treatment of gastrointestinal disorders |
US8143280B2 (en) * | 2007-09-27 | 2012-03-27 | Hoffmann-La Roche Inc. | Glucocorticoid receptor antagonists |
US20090087443A1 (en) | 2007-09-27 | 2009-04-02 | Bartels Stephen P | Pharmacological Adjunctive Treatment Associated with Glaucoma Filtration Surgery |
AR069637A1 (es) | 2007-12-10 | 2010-02-10 | Novartis Ag | Derivados de pirazinas |
JP5584138B2 (ja) | 2008-01-11 | 2014-09-03 | ノバルティス アーゲー | キナーゼ阻害剤としてのピリミジン類 |
US20090239836A1 (en) * | 2008-03-24 | 2009-09-24 | Mary Lee Ciolkowski | Multifunctional Ophthalmic Compositions |
US20090291073A1 (en) * | 2008-05-20 | 2009-11-26 | Ward Keith W | Compositions Comprising PKC-theta and Methods for Treating or Controlling Ophthalmic Disorders Using Same |
CA2724726C (en) | 2008-05-23 | 2018-02-27 | Amira Pharmaceuticals, Inc. | 5-lipoxygenase-activating protein inhibitor |
WO2009147187A1 (en) | 2008-06-05 | 2009-12-10 | Glaxo Group Limited | 4-carboxamide indazole derivatives useful as inhibitors of p13-kinases |
US8765743B2 (en) | 2008-06-05 | 2014-07-01 | Glaxosmithkline Intellectual Property Development Limited | Compounds |
CA2726449A1 (en) * | 2008-06-06 | 2009-12-10 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
JP2011522860A (ja) | 2008-06-10 | 2011-08-04 | ノバルティス アーゲー | 上皮性ナトリウムチャネルブロッカーとしてのピラジン誘導体 |
WO2010049073A1 (en) * | 2008-10-30 | 2010-05-06 | Bayer Schering Pharma Aktiengesellschaft | 1,1,1-trifluoro-3-amino-3-heteroaryl-2-propanoles, a process for their production and their use as anti-inflammatory agents |
JP2012516345A (ja) | 2009-01-29 | 2012-07-19 | ノバルティス アーゲー | 星細胞腫治療用置換ベンゾイミダゾール |
WO2010094643A1 (en) | 2009-02-17 | 2010-08-26 | Glaxo Group Limited | Quinoline derivatives and their uses for rhinitis and urticaria |
WO2010102958A1 (en) | 2009-03-09 | 2010-09-16 | Glaxo Group Limited | 4-oxadiazol-2 -yl- indazoles as inhibitors of p13 kinases |
EP2406249A1 (en) | 2009-03-10 | 2012-01-18 | Glaxo Group Limited | Indole derivatives as ikk2 inhibitors |
US20120058984A1 (en) | 2009-03-17 | 2012-03-08 | Catherine Mary Alder | Pyrimidine derivatives used as itk inhibitors |
CA2755773A1 (en) | 2009-03-19 | 2010-09-23 | Merck Sharp & Dohme Corp. | Rna interference mediated inhibition of btb and cnc homology 1, basic leucine zipper transcription factor 1 (bach 1) gene expression using short interfering nucleic acid (sina) |
US20120016011A1 (en) | 2009-03-19 | 2012-01-19 | Merck Sharp & Dohme Corp. | RNA Interference Mediated Inhibition of Connective Tissue Growth Factor (CTGF) Gene Expression Using Short Interfering Nucleic Acid (siNA) |
JP2012520685A (ja) | 2009-03-19 | 2012-09-10 | メルク・シャープ・エンド・ドーム・コーポレイション | 低分子干渉核酸(siNA)を用いたGATA結合タンパク質3(GATA3)遺伝子発現のRNA干渉媒介性阻害 |
US20120035247A1 (en) | 2009-03-19 | 2012-02-09 | Merck Sharp & Dohme Corp. | RNA Interference Mediated Inhibition of Signal Transducer and Activator of Transcription 6 (STAT6) Gene Expression Using Short Interfering Nucleic Acid (siNA) |
WO2010111497A2 (en) | 2009-03-27 | 2010-09-30 | Merck Sharp & Dohme Corp. | RNA INTERFERENCE MEDIATED INHIBITION OF THE INTERCELLULAR ADHESION MOLECULE 1 (ICAM-1)GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA) |
US20120004281A1 (en) | 2009-03-27 | 2012-01-05 | Merck Sharp & Dohme Corp | RNA Interference Mediated Inhibition of the Nerve Growth Factor Beta Chain (NGFB) Gene Expression Using Short Interfering Nucleic Acid (siNA) |
US20120022142A1 (en) | 2009-03-27 | 2012-01-26 | Merck Sharp & Dohme Corp. | RNA Interference Mediated Inhibition of Signal Transducer and Activator of Transcription 1 (STAT1) Gene Expression Using Short Interfering Nucleic Acid (siNA) |
EP2411516A1 (en) | 2009-03-27 | 2012-02-01 | Merck Sharp&Dohme Corp. | RNA INTERFERENCE MEDIATED INHIBITION OF APOPTOSIS SIGNAL-REGULATING KINASE 1 (ASK1) GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACID (siNA) |
US20120022143A1 (en) | 2009-03-27 | 2012-01-26 | Merck Sharp & Dohme Corp | RNA Interference Mediated Inhibition of the Thymic Stromal Lymphopoietin (TSLP) Gene Expression Using Short Interfering Nucliec Acid (siNA) |
US8456662B2 (en) * | 2009-04-15 | 2013-06-04 | Ricoh Company, Ltd. | Control for display of multiple versions of a printable document for locked print |
US20110077270A1 (en) * | 2009-04-21 | 2011-03-31 | Pfeffer Bruce A | Compositions and Methods for Treating Ocular Inflammation with Lower Risk of Increased Intraocular Pressure |
UY32571A (es) | 2009-04-24 | 2010-11-30 | Glaxo Group Ltd | Compuestos derivados de pirazol amida |
WO2010122088A1 (en) | 2009-04-24 | 2010-10-28 | Glaxo Group Limited | Pyrazole and triazole carboxamides as crac channel inhibitors |
SI2899191T1 (sl) | 2009-04-30 | 2017-11-30 | Glaxo Group Limited | Z oksazolom substituirani indazoli kot PI3-kinazni inhibitorji |
US20100312013A1 (en) | 2009-06-03 | 2010-12-09 | Boehringer Ingelheim International Gmbh | Steroselective synthesis of certain trifluoromethyl-substituted alcohols |
US20110130578A1 (en) | 2009-06-03 | 2011-06-02 | Boehringer Ingelheim International Gmbh | Stereoselective synthesis of certain trifluoromethyl-substituted alcohols |
US20110130567A1 (en) * | 2009-06-03 | 2011-06-02 | Boehringer Ingelheim International Gmbh | Steroselective synthesis of certain trifluoromethyl-substituted alcohols |
US8420819B2 (en) | 2009-06-03 | 2013-04-16 | Boehringer Ingelheim International Gmbh | Process for optimizing the particle size of an active pharmaceutical ingredient by crystallization |
US20110130591A1 (en) * | 2009-06-03 | 2011-06-02 | Boehringer Ingelheim International Gmbh | Steroselective synthesis of certain trifluoromethyl-substituted alcohols |
WO2011016050A2 (en) | 2009-07-31 | 2011-02-10 | Cadila Healthcare Limited | Novel compounds as modulators of glucocorticoid receptors |
US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
AU2010283806A1 (en) | 2009-08-12 | 2012-03-01 | Novartis Ag | Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation |
ES2709108T3 (es) | 2009-08-17 | 2019-04-15 | Intellikine Llc | Compuestos heterocíclicos y usos de los mismos |
AU2010284972A1 (en) | 2009-08-20 | 2012-03-08 | Novartis Ag | Heterocyclic oxime compounds |
EP2813227A1 (en) | 2009-10-22 | 2014-12-17 | Vertex Pharmaceuticals Incorporated | Compositions for treatment of cystic fibrosis and other chronic diseases |
JP2013512878A (ja) | 2009-12-03 | 2013-04-18 | グラクソ グループ リミテッド | 新規化合物 |
JP2013512879A (ja) | 2009-12-03 | 2013-04-18 | グラクソ グループ リミテッド | Pi3キナーゼの阻害剤としてのベンズピラゾール誘導体 |
EP2507231A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Indazole derivatives as pi 3 - kinase inhibitors |
US20120272951A1 (en) | 2009-12-16 | 2012-11-01 | 3M Innovative Properties Company | Formulations and methods for controlling mdi particle size delivery |
WO2011110575A1 (en) | 2010-03-11 | 2011-09-15 | Glaxo Group Limited | Derivatives of 2-[2-(benzo- or pyrido-) thiazolylamino]-6-aminopyridine, useful in the treatment of respiratoric, allergic or inflammatory diseases |
US8247436B2 (en) | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
GB201007203D0 (en) | 2010-04-29 | 2010-06-16 | Glaxo Group Ltd | Novel compounds |
PL2614058T3 (pl) | 2010-09-08 | 2015-12-31 | Glaxosmithkline Ip Dev Ltd | Polimorfy i sole n-[5-[4-(5-{[(2r,6s)-2,6-dimetylo-4-morfolinylo]-metylo}-1,3-oksazol-2-ilo)-1h-indazol-6-ilo]-2-(metyloksy)-3-pirydynylo]metanosulfonamidu |
US9326987B2 (en) | 2010-09-08 | 2016-05-03 | Glaxo Group Limited | Indazole derivatives for use in the treatment of influenza virus infection |
WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
WO2012035055A1 (en) | 2010-09-17 | 2012-03-22 | Glaxo Group Limited | Novel compounds |
US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
ES2532213T3 (es) | 2010-10-21 | 2015-03-25 | Glaxo Group Limited | Compuestos de pirazol que actúan contra afecciones alérgicas, inmunitarias e inflamatorias |
WO2012052459A1 (en) | 2010-10-21 | 2012-04-26 | Glaxo Group Limited | Pyrazole compounds acting against allergic, inflammatory and immune disorders |
GB201018124D0 (en) | 2010-10-27 | 2010-12-08 | Glaxo Group Ltd | Polymorphs and salts |
EP2673277A1 (en) | 2011-02-10 | 2013-12-18 | Novartis AG | [1, 2, 4]triazolo [4, 3 -b]pyridazine compounds as inhibitors of the c-met tyrosine kinase |
US9127000B2 (en) | 2011-02-23 | 2015-09-08 | Intellikine, LLC. | Heterocyclic compounds and uses thereof |
WO2012116217A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Compounds and compositions as trk inhibitors |
US20140005188A1 (en) | 2011-03-11 | 2014-01-02 | Glaxo Group Limited | Pyrido[3,4-b]pyrazine derivatives as syk inhibitors |
GB201104153D0 (en) | 2011-03-11 | 2011-04-27 | Glaxo Group Ltd | Novel compounds |
US20120316199A1 (en) | 2011-06-07 | 2012-12-13 | Ward Keith W | Compositions and methods for treating, controlling, reducing, or ameliorating inflammatory pain |
UY34305A (es) | 2011-09-01 | 2013-04-30 | Novartis Ag | Derivados de heterociclos bicíclicos para el tratamiento de la hipertensión arterial pulmonar |
BR112014006223A8 (pt) | 2011-09-15 | 2018-01-09 | Novartis Ag | 3-(quinolin-6-iltio)-[1,2,4-triazol[4,3-a] piradinas 6-substituídas, seus usos, composições farmacêuticas, e combinação |
WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
US9056867B2 (en) | 2011-09-16 | 2015-06-16 | Novartis Ag | N-substituted heterocyclyl carboxamides |
CN103946221B (zh) | 2011-09-16 | 2016-08-03 | 诺华股份有限公司 | 用于治疗囊性纤维化的杂环化合物 |
WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
JP6130391B2 (ja) | 2011-11-23 | 2017-05-17 | インテリカイン, エルエルシー | Mtor阻害剤を使用する強化された治療レジメン |
US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
CN104245701A (zh) | 2012-04-03 | 2014-12-24 | 诺华有限公司 | 有酪氨酸激酶抑制剂的组合产品和其应用 |
US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
EP2968340A4 (en) | 2013-03-15 | 2016-08-10 | Intellikine Llc | COMBINING KINASE INHIBITORS AND USES THEREOF |
EP3007697B1 (en) | 2013-06-14 | 2020-09-02 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Rac1 inhibitors for inducing bronchodilation |
CA2920059A1 (en) | 2013-09-22 | 2015-03-26 | Calitor Sciences, Llc | Substituted aminopyrimidine compounds and methods of use |
CA2923995A1 (en) | 2013-10-17 | 2015-04-23 | Glaxosmithkline Intellectual Property Development Limited | Pi3k inhibitor for treatment of respiratory disease |
US20160263109A1 (en) | 2013-10-17 | 2016-09-15 | Glaxosmithkline Intellectual Property Development Limited | P13k inhibitor for treatment of respiratory disease |
WO2015084804A1 (en) | 2013-12-03 | 2015-06-11 | Novartis Ag | Combination of mdm2 inhibitor and braf inhibitor and their use |
EP3327006B1 (en) | 2014-03-28 | 2020-05-20 | Calitor Sciences, LLC | Substituted heteroaryl compounds and methods of use |
AU2014391610B2 (en) | 2014-04-24 | 2018-01-25 | Novartis Ag | Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
US10004732B2 (en) | 2014-04-24 | 2018-06-26 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
PT3134396T (pt) | 2014-04-24 | 2019-12-16 | Novartis Ag | Derivados de amino piridina como inibidores da fosfatidilinositol 3-quinase |
KR20170003673A (ko) | 2014-05-12 | 2017-01-09 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | 감염성 질환을 치료하기 위한 다니릭신을 포함하는 약제 조성물 |
WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
MX2017001461A (es) | 2014-07-31 | 2017-05-11 | Novartis Ag | Terapia de combinacion. |
WO2017044434A1 (en) | 2015-09-11 | 2017-03-16 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
CN105418529B (zh) * | 2015-12-30 | 2017-07-18 | 商丘师范学院 | 一种含4‑硝基异噁唑基三氟甲基叔醇化合物及其制备方法 |
CN105622536B (zh) * | 2015-12-30 | 2018-06-29 | 商丘师范学院 | 一种三氟甲基化烯基异噁唑化合物及其制备方法和应用 |
GB201602527D0 (en) | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
EP3497100A1 (en) | 2016-08-08 | 2019-06-19 | GlaxoSmithKline Intellectual Property Development Limited | Chemical compounds |
GB201706102D0 (en) | 2017-04-18 | 2017-05-31 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
GB201712081D0 (en) | 2017-07-27 | 2017-09-13 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
JP7254076B2 (ja) | 2017-11-19 | 2023-04-07 | サンシャイン・レイク・ファーマ・カンパニー・リミテッド | 置換ヘテロアリール化合物及び使用方法 |
AU2019209960B2 (en) | 2018-01-20 | 2023-11-23 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
BR112021024668A2 (pt) | 2019-06-10 | 2022-05-31 | Novartis Ag | Derivado de piridina e pirazina para o tratamento de fc, dpoc e bronquiectasia |
PE20220346A1 (es) | 2019-08-28 | 2022-03-14 | Novartis Ag | Derivados de 1,3-fenil heteroarilo sustituidos y su uso en el tratamiento de enfermedades |
TW202140550A (zh) | 2020-01-29 | 2021-11-01 | 瑞士商諾華公司 | 使用抗tslp抗體治療炎性或阻塞性氣道疾病之方法 |
WO2021191875A1 (en) | 2020-03-26 | 2021-09-30 | Glaxosmithkline Intellectual Property Development Limited | Cathepsin inhibitors for preventing or treating viral infections |
Family Cites Families (80)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1017612B (de) | 1954-02-05 | 1957-10-17 | Thomae Gmbh Dr K | Verfahren zur Herstellung von tertiaeren Aminen, ihren Saeureadditionssalzen und quaternaeren Ammoniumverbindungen |
US3772273A (en) | 1969-01-17 | 1973-11-13 | Allied Chem | Derivatives of quinoxaline |
NL8402755A (nl) | 1983-09-22 | 1985-04-16 | Sandoz Ag | Azool-derivaten, werkwijze voor het bereiden daarvan, preparaten die ze bevatten, en toepassing daarvan. |
JPS60163814A (ja) | 1984-02-06 | 1985-08-26 | Wataru Mori | グルココルチコイド拮抗剤 |
GB8406000D0 (en) | 1984-03-07 | 1984-04-11 | Ici Plc | Olefine derivatives |
US4551534A (en) | 1984-03-30 | 1985-11-05 | American Home Products Corporation | Aralkyl or aryloxyalkyl 1,7-naphthyridine-3-carboxylic acid esters |
DE3514696A1 (de) | 1985-04-24 | 1986-11-06 | Bayer Ag, 5090 Leverkusen | N-indolylethyl-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung |
GB8617653D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Amide derivatives |
GB8617652D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
GB2210875B (en) | 1987-10-09 | 1991-05-29 | Farmos Oy | Aromatase inhibiting 4(5)-imidazoles |
US5039691A (en) | 1989-06-08 | 1991-08-13 | Marion Merrell Dow Inc. | 5-(1-(imidazol)methyl)-3,3-disubstituted-2(3H)furanone derivatives |
US5206377A (en) | 1991-12-05 | 1993-04-27 | Whitby Research, Inc. | Compounds useful as antiproliferative agents |
JPH05194404A (ja) | 1992-01-22 | 1993-08-03 | Zeria Pharmaceut Co Ltd | カルボスチリル誘導体 |
GB9201755D0 (en) | 1992-01-28 | 1992-03-11 | British Bio Technology | Compounds |
US5948820A (en) | 1994-08-22 | 1999-09-07 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzene compound and pharmaceutical use thereof |
EP1382597A3 (en) | 1994-12-22 | 2004-04-07 | Ligand Pharmaceuticals, Inc. | Steroid receptor modulator compounds and methods |
US5688810A (en) | 1994-12-22 | 1997-11-18 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
JP2000504014A (ja) | 1996-01-30 | 2000-04-04 | メルク エンド カンパニー インコーポレーテッド | ファルネシル―タンパク質転移酵素の阻害剤 |
DE19723722A1 (de) | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
JPH1180131A (ja) | 1997-09-01 | 1999-03-26 | Mitsubishi Chem Corp | エチニルピリミジン誘導体 |
CO4980885A1 (es) | 1997-12-29 | 2000-11-27 | Ortho Mcneil Pharm Inc | Compuestos de trifenilpropanamida utiles en el tratamiento de inflamaciones y metodos para preparar dicho compuesto |
PL193323B1 (pl) | 1998-02-13 | 2007-02-28 | Abbott Lab | Glukokortykoido-selektywne benzopirano[3,4-f]chinoliny, kompozycja farmaceutyczna je zawierająca oraz ich zastosowanie |
US6506766B1 (en) | 1998-02-13 | 2003-01-14 | Abbott Laboratories | Glucocortiocoid-selective antinflammatory agents |
DE69906849T2 (de) | 1998-02-16 | 2004-01-22 | Ajinomoto Co., Inc. | Verfahren zur Herstellung von optisch aktiven Phenylpropionsäure-Derivat |
DE19816624A1 (de) | 1998-04-15 | 1999-10-21 | Boehringer Ingelheim Pharma | Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
US6169106B1 (en) | 1998-04-15 | 2001-01-02 | Boehringer Ingelheim Pharma Kg | Indolinones having kinase inhibitory activity |
EP1143948A3 (en) | 1998-06-08 | 2002-09-11 | Karo Bio Ab | Liver-selective glucocorticoid antagonist for treating diabetes |
US6187918B1 (en) | 1999-03-15 | 2001-02-13 | Dupont Pharmaceuticals Company | Catalysts for asymmetric addition of organozinc reagents to aldehydes and method for preparation |
NZ510845A (en) | 1998-09-25 | 2003-10-31 | Boehringer Ingelheim Pharma | Novel substituted indolinones with an inhibitory effect on various kinases and cyclin/CDK complexes |
DE19856475A1 (de) | 1998-11-27 | 2000-05-31 | Schering Ag | Nichtsteroidale Entzündungshemmer |
MXPA01011018A (es) * | 1999-04-30 | 2002-05-06 | Pfizer Prod Inc | Moduladores del receptor glucocorticoide. |
WO2001005784A1 (en) | 1999-07-16 | 2001-01-25 | Bristol-Myers Squibb Pharma Company | NITROGEN CONTAINING HETEROBICYCLES AS FACTOR Xa INHIBITORS |
US6329534B1 (en) | 1999-09-01 | 2001-12-11 | Abbott Laboratories | Glucocorticoid receptor antagonists for treatment of diabetes |
US6436986B1 (en) | 1999-09-01 | 2002-08-20 | Abbott Laboratories | Glucocorticoid receptor antagonists for treatment of diabetes |
CO5271670A1 (es) * | 1999-10-29 | 2003-04-30 | Pfizer Prod Inc | Antagonistas del factor de liberacion de corticitropina y composiciones relacionadas |
US7713989B2 (en) * | 2000-04-27 | 2010-05-11 | Dow Robert L | Glucocorticoid receptor modulators |
AU779041B2 (en) | 2000-05-02 | 2005-01-06 | Meiji Seika Kaisha Ltd. | Novel indole derivatives exhibiting chymase-inhibitory activities and process for preparation thereof |
EP1157682A1 (en) | 2000-05-25 | 2001-11-28 | Cilag AG | Blister package for topiramate tablets |
DE10038639A1 (de) | 2000-07-28 | 2002-02-21 | Schering Ag | Nichtsteroidale Entzündungshemmer |
CN1450896A (zh) | 2000-07-28 | 2003-10-22 | 印斯拜尔药品股份有限公司 | 用吲哚衍生物降低眼内压的方法 |
US7064123B1 (en) | 2000-12-22 | 2006-06-20 | Aventis Pharmaceuticals Inc. | Compounds and compositions as cathepsin inhibitors |
US7030116B2 (en) | 2000-12-22 | 2006-04-18 | Aventis Pharmaceuticals Inc. | Compounds and compositions as cathepsin inhibitors |
US6583180B2 (en) | 2001-02-14 | 2003-06-24 | Abbott Laboratories | Glucocorticoid receptor modulators |
DK1363876T3 (da) | 2001-02-14 | 2009-11-30 | Karobio Ab | Glucocorticoidreceptormodulatorer |
US6872533B2 (en) | 2001-07-27 | 2005-03-29 | The Regents Of The University Of California | STK15 (STK6) gene polymorphism and methods of determining cancer risk |
GB0124299D0 (en) | 2001-10-10 | 2001-11-28 | Astrazeneca Ab | Crystal structure of enzyme and uses thereof |
ATE407678T1 (de) | 2001-10-17 | 2008-09-15 | Boehringer Ingelheim Pharma | Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung |
WO2003059899A1 (en) | 2002-01-14 | 2003-07-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof |
NZ535889A (en) | 2002-03-26 | 2006-03-31 | Boehringer Ingelheim Pharma | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
JP2005521717A (ja) | 2002-03-26 | 2005-07-21 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | グルココルチコイドミメチックス、その製造方法、その医薬組成物、及び使用 |
US6897224B2 (en) | 2002-04-02 | 2005-05-24 | Schering Ag | Quinoline and isoquinoline derivatives, a process for their production and their use as inflammation inhibitors |
DE10215316C1 (de) | 2002-04-02 | 2003-12-18 | Schering Ag | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
US7186864B2 (en) | 2002-05-29 | 2007-03-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
US7074806B2 (en) | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
ITMI20021247A1 (it) | 2002-06-07 | 2003-12-09 | Menarini Ricerche Spa | Antagonisti basici non peptidici della bradichinina e loro impiego informulazioni farmaceutiche |
GB0215650D0 (en) | 2002-07-05 | 2002-08-14 | Cyclacel Ltd | Bisarylsufonamide compounds |
JP2006504678A (ja) | 2002-08-21 | 2006-02-09 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | グルココルチコイドミメチックス、その製造方法、その医薬組成物、及び使用 |
JP4619786B2 (ja) | 2002-08-29 | 2011-01-26 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 炎症性、アレルギー性及び増殖性疾患の治療において糖質コルチコイドミメティックスとして使用するための3−(スルホンアミドエチル)−インドール誘導体 |
US7112584B2 (en) | 2002-12-20 | 2006-09-26 | Schering Ag | Nonsteroidal antiinflammatory agents |
WO2004063163A1 (en) | 2003-01-03 | 2004-07-29 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1-propanol and 1-propylamine derivatives and their use as glucocorticoid ligands |
DE602004022633D1 (de) | 2003-01-30 | 2009-10-01 | Boehringer Ingelheim Pharma | 2,4-diaminopyrimidinderivate, die sich als inhibitoren von pkc-theta eignen |
WO2004071389A2 (en) | 2003-02-15 | 2004-08-26 | Glaxo Group Limited | Non-steroidal infalmmation inhibitors |
US20040224992A1 (en) | 2003-02-27 | 2004-11-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
JP2006522744A (ja) | 2003-04-11 | 2006-10-05 | ノボ ノルディスク アクティーゼルスカブ | グルココルチコイド受容体アゴニスト療法に伴う副作用を最小化するための、11β−ヒドロキシステロイドデヒドロゲナーゼ1型阻害剤およびグルココルチコイド受容体アゴニストを使用する併用療法 |
EP1656366A1 (en) | 2003-08-20 | 2006-05-17 | Amgen Inc. | Substituted pyrimdinone derivatives and methods of use |
UY28526A1 (es) | 2003-09-24 | 2005-04-29 | Boehringer Ingelheim Pharma | Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos |
JP4949845B2 (ja) | 2003-10-03 | 2012-06-13 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | タンパク質キナーゼインヒビター結合アッセイにおける使用のための蛍光プローブ |
ATE366726T1 (de) | 2003-10-16 | 2007-08-15 | Boehringer Ingelheim Pharma | Stereoselektive synthese bestimmter trifluormethylsubstituierter alkohole |
US7795272B2 (en) | 2004-03-13 | 2010-09-14 | Boehringer Ingelheim Pharmaceutical, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof |
US7179919B2 (en) | 2004-03-18 | 2007-02-20 | Boehringer Ingelheim Pharmaceuticals, Inc. | Stereoselective synthesis of certain trifluoromethyl-substituted alcohols |
EP1730145A1 (en) * | 2004-03-22 | 2006-12-13 | Boehringer Ingelheim Pharmaceuticals Inc. | Alpha-trifluoromethyl alcohols or amines as glucocorticoid mimetics |
WO2005100335A1 (en) | 2004-03-30 | 2005-10-27 | Boehringer Ingelheim Pharmaceuticals, Inc. | Stereoselective synthesis of certain trifluoromethyl-substituted oxiranes |
US20060030608A1 (en) | 2004-08-04 | 2006-02-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti aromatase compounds pharmaceutical compositions and uses thereof |
BRPI0517263A (pt) | 2004-10-29 | 2008-10-07 | Astrazeneca Ab | novos derivados de sulfonamida como moduladores do receptor de glicocorticóide para o tratamento de doenças inflamatórias |
US20070072870A2 (en) | 2004-12-08 | 2007-03-29 | Solvay Pharmeceuticals B.V. | Phenylpiperazine derivatives with a combination of partial dopamine-d2 receptor agonism and serotonin reuptake inhibition |
PE20060776A1 (es) | 2004-12-27 | 2006-09-26 | Boehringer Ingelheim Pharma | Mimeticos de glucocorticoides, metodos para prepararlos y composiciones farmaceuticas |
US20090176807A1 (en) | 2005-03-04 | 2009-07-09 | John Robinson Regan | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
WO2006135826A1 (en) | 2005-06-10 | 2006-12-21 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
EP1934218B1 (en) * | 2005-09-30 | 2009-11-18 | Boehringer Ingelheim International GmbH | Stereoselective synthesis of certain trifluoromethyl-substituted alcohols |
CA2726449A1 (en) | 2008-06-06 | 2009-12-10 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
-
2003
- 2003-03-21 NZ NZ535889A patent/NZ535889A/xx not_active IP Right Cessation
- 2003-03-21 BR BR0308784-0A patent/BR0308784A/pt not_active Expired - Fee Related
- 2003-03-21 ES ES03714339T patent/ES2298508T3/es not_active Expired - Lifetime
- 2003-03-21 MX MXPA04009329A patent/MXPA04009329A/es active IP Right Grant
- 2003-03-21 DE DE60318188T patent/DE60318188T2/de not_active Expired - Lifetime
- 2003-03-21 KR KR1020047015403A patent/KR101022977B1/ko not_active IP Right Cessation
- 2003-03-21 JP JP2003579818A patent/JP4324480B2/ja not_active Expired - Fee Related
- 2003-03-21 AU AU2003218342A patent/AU2003218342B8/en not_active Ceased
- 2003-03-21 CN CNA038071800A patent/CN1633296A/zh active Pending
- 2003-03-21 CA CA2478156A patent/CA2478156C/en not_active Expired - Fee Related
- 2003-03-21 DK DK03714339T patent/DK1490062T3/da active
- 2003-03-21 EA EA200401194A patent/EA008830B1/ru not_active IP Right Cessation
- 2003-03-21 EP EP03714339A patent/EP1490062B1/en not_active Expired - Lifetime
- 2003-03-21 PT PT03714339T patent/PT1490062E/pt unknown
- 2003-03-21 PL PL03373043A patent/PL373043A1/xx unknown
- 2003-03-21 WO PCT/US2003/008901 patent/WO2003082280A1/en active IP Right Grant
- 2003-03-21 AT AT03714339T patent/ATE381333T1/de active
- 2003-03-21 UA UA20041008648A patent/UA80120C2/uk unknown
- 2003-03-21 RS YUP-828/04A patent/RS51097B/sr unknown
- 2003-03-21 US US10/394,303 patent/US6903215B2/en not_active Expired - Lifetime
- 2003-03-24 PE PE2003000290A patent/PE20040164A1/es not_active Application Discontinuation
- 2003-03-25 TW TW092106617A patent/TWI326213B/zh not_active IP Right Cessation
- 2003-03-26 AR ARP030101045A patent/AR039140A1/es not_active Suspension/Interruption
- 2003-03-26 UY UY27736A patent/UY27736A1/es not_active Application Discontinuation
- 2003-07-19 SA SA07280239A patent/SA07280239B1/ar unknown
- 2003-07-19 SA SA03240209A patent/SA03240209B1/ar unknown
- 2003-07-19 SA SA7280240A patent/SA07280240B1/ar unknown
-
2004
- 2004-08-04 ZA ZA200406225A patent/ZA200406225B/en unknown
- 2004-08-05 IL IL163366A patent/IL163366A/en not_active IP Right Cessation
- 2004-09-17 US US10/944,615 patent/US7553966B2/en not_active Expired - Lifetime
- 2004-09-24 NO NO20044031A patent/NO329386B1/no not_active IP Right Cessation
- 2004-09-24 EC EC2004005315A patent/ECSP045315A/es unknown
- 2004-09-24 HR HR20040887A patent/HRP20040887A2/hr not_active Application Discontinuation
- 2004-10-21 CO CO04105799A patent/CO5611110A2/es not_active Application Discontinuation
-
2005
- 2005-07-20 US US11/185,349 patent/US7932392B2/en active Active
-
2006
- 2006-04-25 US US11/410,408 patent/US8212040B2/en not_active Expired - Lifetime
-
2008
- 2008-03-17 CY CY20081100298T patent/CY1107244T1/el unknown
-
2010
- 2010-04-15 CL CL2010000375A patent/CL2010000375A1/es unknown
- 2010-06-10 NO NO20100827A patent/NO20100827L/no not_active Application Discontinuation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1490062B1 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof | |
US7795272B2 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof | |
US7074806B2 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof | |
EP1539141B1 (en) | 3-(sulfonamidoethyl)-indole derivatives for use as glucocorticoid mimetics in the treatment of inflammatory, allergic and proliferative diseases | |
US8741897B2 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof | |
US20040010020A1 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof | |
EP1893588A1 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof | |
EP1490317A1 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof | |
PT2300472E (pt) | Miméticos de glucocorticóides, métodos de os preparar, composições farmacêuticas e suas utilizações | |
EP2183217A2 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof | |
EP1730145A1 (en) | Alpha-trifluoromethyl alcohols or amines as glucocorticoid mimetics |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |