WO2008049047A2 - Quinoline compounds - Google Patents
Quinoline compounds Download PDFInfo
- Publication number
- WO2008049047A2 WO2008049047A2 PCT/US2007/081738 US2007081738W WO2008049047A2 WO 2008049047 A2 WO2008049047 A2 WO 2008049047A2 US 2007081738 W US2007081738 W US 2007081738W WO 2008049047 A2 WO2008049047 A2 WO 2008049047A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- trifluoromethyl
- phenyl
- quinoline
- phenoxy
- methylsulfonyl
- Prior art date
Links
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 10
- 238000000034 method Methods 0.000 claims abstract description 115
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 66
- 102000004311 liver X receptors Human genes 0.000 claims abstract description 50
- 108090000865 liver X receptors Proteins 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims description 429
- 125000004429 atom Chemical group 0.000 claims description 288
- -1 Ci-C6 alkyl Inorganic materials 0.000 claims description 195
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 131
- 239000001257 hydrogen Substances 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 129
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 87
- 125000001072 heteroaryl group Chemical group 0.000 claims description 75
- 125000005843 halogen group Chemical group 0.000 claims description 71
- 125000000623 heterocyclic group Chemical group 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 125000001188 haloalkyl group Chemical group 0.000 claims description 61
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 47
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 45
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 41
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 39
- 125000004076 pyridyl group Chemical group 0.000 claims description 39
- 125000006413 ring segment Chemical group 0.000 claims description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000001153 fluoro group Chemical group F* 0.000 claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 230000000694 effects Effects 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
- 230000003143 atherosclerotic effect Effects 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 13
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 12
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 11
- 210000002966 serum Anatomy 0.000 claims description 11
- 125000005296 thioaryloxy group Chemical group 0.000 claims description 11
- 125000005404 thioheteroaryloxy group Chemical group 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 9
- YRLSCCZSKWRLSP-UHFFFAOYSA-N 3-phenylbenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 YRLSCCZSKWRLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 9
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 9
- 125000004419 alkynylene group Chemical group 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 201000001320 Atherosclerosis Diseases 0.000 claims description 8
- 206010061218 Inflammation Diseases 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 230000003902 lesion Effects 0.000 claims description 8
- 230000009759 skin aging Effects 0.000 claims description 8
- 230000001154 acute effect Effects 0.000 claims description 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
- 230000001684 chronic effect Effects 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 230000004141 reverse cholesterol transport Effects 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 7
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 206010012442 Dermatitis contact Diseases 0.000 claims description 6
- 238000008214 LDL Cholesterol Methods 0.000 claims description 6
- 206010040047 Sepsis Diseases 0.000 claims description 6
- 210000001367 artery Anatomy 0.000 claims description 6
- 208000010247 contact dermatitis Diseases 0.000 claims description 6
- 150000002632 lipids Chemical class 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
- JXCBEOWENFIDSM-UHFFFAOYSA-N 3-[3-(8-chloro-3-methylquinolin-4-yl)phenoxy]aniline Chemical compound CC1=CN=C2C(Cl)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(N)=C1 JXCBEOWENFIDSM-UHFFFAOYSA-N 0.000 claims description 5
- CJZCASOLCSCNID-UHFFFAOYSA-N 4-[2-chloro-5-(3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinoline Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C=C(C(Cl)=CC=2)C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=C1 CJZCASOLCSCNID-UHFFFAOYSA-N 0.000 claims description 5
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 102000004127 Cytokines Human genes 0.000 claims description 5
- 108090000695 Cytokines Proteins 0.000 claims description 5
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
- 201000009273 Endometriosis Diseases 0.000 claims description 5
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
- 108010003059 aggrecanase Proteins 0.000 claims description 5
- 125000005605 benzo group Chemical group 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 208000037803 restenosis Diseases 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 206010043778 thyroiditis Diseases 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 4
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 4
- HZBPHRRMQCPHHG-UHFFFAOYSA-N 4-[3-[3-(8-chloro-3-methylquinolin-4-yl)phenoxy]phenyl]sulfonylmorpholine Chemical compound CC1=CN=C2C(Cl)=CC=CC2=C1C(C=1)=CC=CC=1OC(C=1)=CC=CC=1S(=O)(=O)N1CCOCC1 HZBPHRRMQCPHHG-UHFFFAOYSA-N 0.000 claims description 4
- VLLNTQMNUYPYHX-UHFFFAOYSA-N 8-bromo-3-methyl-4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline Chemical compound CC1=CN=C2C(Br)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(C)(=O)=O)=C1 VLLNTQMNUYPYHX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 208000018631 connective tissue disease Diseases 0.000 claims description 4
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 4
- 230000003247 decreasing effect Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- XPZRMBZMAJAPLC-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) 3-[[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenyl]methyl]benzenesulfonate Chemical compound CC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1CC(C=1)=CC=CC=1S(=O)(=O)OC1=C(F)C(F)=C(F)C(F)=C1F XPZRMBZMAJAPLC-UHFFFAOYSA-N 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- CBDRKJFYMHATMY-UHFFFAOYSA-N 2-methylsulfonyl-6-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]pyridin-4-amine Chemical compound CC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC(N)=CC(S(C)(=O)=O)=N1 CBDRKJFYMHATMY-UHFFFAOYSA-N 0.000 claims description 3
- VZFMPAWHLYJYFL-UHFFFAOYSA-N 3,5-dichloro-2-methylsulfonyl-6-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]pyridin-4-amine Chemical compound CC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC1=NC(S(C)(=O)=O)=C(Cl)C(N)=C1Cl VZFMPAWHLYJYFL-UHFFFAOYSA-N 0.000 claims description 3
- RZYPXOCXGMGYCN-UHFFFAOYSA-N 3-methyl-4-[3-(2-methylsulfanylpyridin-4-yl)oxyphenyl]-8-(trifluoromethyl)quinoline Chemical compound C1=NC(SC)=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 RZYPXOCXGMGYCN-UHFFFAOYSA-N 0.000 claims description 3
- ZDUOYBOFMKORCT-UHFFFAOYSA-N 3-methyl-4-[3-(3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinoline Chemical compound CC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(C)(=O)=O)=C1 ZDUOYBOFMKORCT-UHFFFAOYSA-N 0.000 claims description 3
- BCWPLOTXDYAXHD-UHFFFAOYSA-N 3-methyl-4-[3-(4-methylsulfanylpyridin-2-yl)oxyphenyl]-8-(trifluoromethyl)quinoline Chemical compound CSC1=CC=NC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 BCWPLOTXDYAXHD-UHFFFAOYSA-N 0.000 claims description 3
- OXAVBDIDWNTRGP-UHFFFAOYSA-N 4-[3-(3-chloro-5-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CS(=O)(=O)C1=CC(Cl)=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C(N)=O)C(F)(F)F)=C1 OXAVBDIDWNTRGP-UHFFFAOYSA-N 0.000 claims description 3
- ZIMHQMXADUASSG-UHFFFAOYSA-N 4-[3-(3-ethylsulfonylphenoxy)phenyl]-3-methyl-8-(trifluoromethyl)quinoline Chemical compound CCS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 ZIMHQMXADUASSG-UHFFFAOYSA-N 0.000 claims description 3
- CKHYMMLNOQQEMV-UHFFFAOYSA-N 4-[3-(3-ethylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinoline-3-carboxamide Chemical compound CCS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C(N)=O)C(F)(F)F)=C1 CKHYMMLNOQQEMV-UHFFFAOYSA-N 0.000 claims description 3
- WGKVDODXCWHATF-UHFFFAOYSA-N 4-[3-(3-fluoro-5-methylsulfonylphenoxy)phenyl]-8-methylsulfonylquinoline Chemical compound CS(=O)(=O)C1=CC(F)=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2)S(C)(=O)=O)=C1 WGKVDODXCWHATF-UHFFFAOYSA-N 0.000 claims description 3
- DHCPTZAZDOXILJ-UHFFFAOYSA-N 4-[3-(3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinoline-3-carbonitrile Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C#N)C(F)(F)F)=C1 DHCPTZAZDOXILJ-UHFFFAOYSA-N 0.000 claims description 3
- HRCBWCKPBWZCRB-UHFFFAOYSA-N 4-[3-(3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinoline-3-carboxylic acid Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C(O)=O)C(F)(F)F)=C1 HRCBWCKPBWZCRB-UHFFFAOYSA-N 0.000 claims description 3
- TYNVCZOGOQNEMM-UHFFFAOYSA-N 4-[3-(4-chloro-3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinoline Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=C1 TYNVCZOGOQNEMM-UHFFFAOYSA-N 0.000 claims description 3
- VNKGDDXILDCQBZ-UHFFFAOYSA-N 4-[3-(4-methyl-3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinoline Chemical compound C1=C(S(C)(=O)=O)C(C)=CC=C1OC1=CC=CC(C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=C1 VNKGDDXILDCQBZ-UHFFFAOYSA-N 0.000 claims description 3
- OWWIFUBZUNIFPL-UHFFFAOYSA-N 4-[3-(4-methyl-3-methylsulfonylphenyl)phenyl]-8-(trifluoromethyl)quinoline Chemical compound C1=C(S(C)(=O)=O)C(C)=CC=C1C1=CC=CC(C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=C1 OWWIFUBZUNIFPL-UHFFFAOYSA-N 0.000 claims description 3
- SDDBCVFEPAYBNR-UHFFFAOYSA-N 4-[3-(6-fluoropyridin-2-yl)oxyphenyl]-3-methyl-8-(trifluoromethyl)quinoline Chemical compound CC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(F)=N1 SDDBCVFEPAYBNR-UHFFFAOYSA-N 0.000 claims description 3
- BPCSTAWYKDXMJJ-UHFFFAOYSA-N 4-[5-(4-ethylsulfonylphenoxy)-2-fluorophenyl]-8-(trifluoromethyl)quinoline Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1OC1=CC=C(F)C(C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=C1 BPCSTAWYKDXMJJ-UHFFFAOYSA-N 0.000 claims description 3
- PBQUJALWEDBRLW-UHFFFAOYSA-N 8-chloro-3-methyl-4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline Chemical compound CC1=CN=C2C(Cl)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(C)(=O)=O)=C1 PBQUJALWEDBRLW-UHFFFAOYSA-N 0.000 claims description 3
- RWAFYOILUINOML-UHFFFAOYSA-N 8-chloro-3-methyl-4-[3-(3-nitrophenoxy)phenyl]quinoline Chemical compound CC1=CN=C2C(Cl)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC([N+]([O-])=O)=C1 RWAFYOILUINOML-UHFFFAOYSA-N 0.000 claims description 3
- PAZSKPAMPGSZKI-UHFFFAOYSA-N 8-chloro-4-[3-(3-ethylsulfonylphenoxy)phenyl]quinoline Chemical compound CCS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=CC=2)=C1 PAZSKPAMPGSZKI-UHFFFAOYSA-N 0.000 claims description 3
- IKEBXOQTSPUHRL-UHFFFAOYSA-N 8-chloro-4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=CC=2)=C1 IKEBXOQTSPUHRL-UHFFFAOYSA-N 0.000 claims description 3
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- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
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- WOSSYGNCERDFGK-UHFFFAOYSA-N 2,2-dimethyl-3-[3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]sulfonylpropan-1-ol Chemical compound CC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(=O)(=O)CC(C)(C)CO)=C1 WOSSYGNCERDFGK-UHFFFAOYSA-N 0.000 claims description 2
- ZEVWDMAPKJGEMJ-UHFFFAOYSA-N 2-[3-[3-[3-(8-chloro-3-methylquinolin-4-yl)phenoxy]phenyl]-2-oxoimidazolidin-1-yl]acetic acid Chemical compound CC1=CN=C2C(Cl)=CC=CC2=C1C(C=1)=CC=CC=1OC(C=1)=CC=CC=1N1CCN(CC(O)=O)C1=O ZEVWDMAPKJGEMJ-UHFFFAOYSA-N 0.000 claims description 2
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- UCPCLSOVORSWOU-UHFFFAOYSA-N 2-methyl-4-[3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]sulfonylbutan-2-ol Chemical compound CC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(=O)(=O)CCC(C)(C)O)=C1 UCPCLSOVORSWOU-UHFFFAOYSA-N 0.000 claims description 2
- QDFSVNLEYCFYBN-UHFFFAOYSA-N 2-methyl-4-[3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenyl]phenyl]sulfonylbutan-2-ol Chemical compound CC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1C1=CC=CC(S(=O)(=O)CCC(C)(C)O)=C1 QDFSVNLEYCFYBN-UHFFFAOYSA-N 0.000 claims description 2
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- XDGAIWDXJNLLJT-UHFFFAOYSA-N 8-chloro-4-[2-fluoro-5-(3-propan-2-ylsulfonylphenoxy)phenyl]-2-methylquinoline Chemical compound CC(C)S(=O)(=O)C1=CC=CC(OC=2C=C(C(F)=CC=2)C=2C3=CC=CC(Cl)=C3N=C(C)C=2)=C1 XDGAIWDXJNLLJT-UHFFFAOYSA-N 0.000 claims 1
- LPSBFBUYCOTTJC-UHFFFAOYSA-N 8-chloro-4-[2-fluoro-5-[(3-methylsulfonylphenyl)methoxy]phenyl]-2-methylquinoline Chemical compound C=12C=CC=C(Cl)C2=NC(C)=CC=1C(C(=CC=1)F)=CC=1OCC1=CC=CC(S(C)(=O)=O)=C1 LPSBFBUYCOTTJC-UHFFFAOYSA-N 0.000 claims 1
- CGDSEFFFLPRQGT-UHFFFAOYSA-N 8-chloro-4-[3-(3-chloro-5-methylsulfonylphenoxy)phenyl]quinoline-3-carboxamide Chemical compound CS(=O)(=O)C1=CC(Cl)=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=CC=2C(N)=O)=C1 CGDSEFFFLPRQGT-UHFFFAOYSA-N 0.000 claims 1
- QEYCVPYSEZFGHC-UHFFFAOYSA-N 8-chloro-4-[3-(3-ethylsulfonyl-5-fluorophenoxy)phenyl]-2-methylquinoline Chemical compound CCS(=O)(=O)C1=CC(F)=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=C(C)C=2)=C1 QEYCVPYSEZFGHC-UHFFFAOYSA-N 0.000 claims 1
- MCOHAXYKUQCYKM-UHFFFAOYSA-N 8-chloro-4-[3-(3-ethylsulfonylphenoxy)phenyl]-2-methylquinoline Chemical compound CCS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=C(C)C=2)=C1 MCOHAXYKUQCYKM-UHFFFAOYSA-N 0.000 claims 1
- PFFUNCOQAROXGV-UHFFFAOYSA-N 8-chloro-4-[3-(3-ethylsulfonylphenoxy)phenyl]quinoline-3-carboxamide Chemical compound CCS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=CC=2C(N)=O)=C1 PFFUNCOQAROXGV-UHFFFAOYSA-N 0.000 claims 1
- DJLAEAMAEHLFQV-UHFFFAOYSA-N 8-chloro-4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline-3-carbonitrile Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=CC=2C#N)=C1 DJLAEAMAEHLFQV-UHFFFAOYSA-N 0.000 claims 1
- LCRUTDAWNZRMRN-UHFFFAOYSA-N 8-chloro-4-[3-(3-methylsulfonylphenyl)phenyl]quinoline Chemical compound CS(=O)(=O)C1=CC=CC(C=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=CC=2)=C1 LCRUTDAWNZRMRN-UHFFFAOYSA-N 0.000 claims 1
- VYLWXGYHEVCLHE-UHFFFAOYSA-N 8-chloro-4-[5-(3-ethylsulfonyl-5-fluorophenoxy)-2-fluorophenyl]-2-methylquinoline Chemical compound CCS(=O)(=O)C1=CC(F)=CC(OC=2C=C(C(F)=CC=2)C=2C3=CC=CC(Cl)=C3N=C(C)C=2)=C1 VYLWXGYHEVCLHE-UHFFFAOYSA-N 0.000 claims 1
- WBCYHJJQXUSRSD-UHFFFAOYSA-N 8-chloro-4-[5-(3-ethylsulfonylphenoxy)-2-fluorophenyl]-2-methylquinoline Chemical compound CCS(=O)(=O)C1=CC=CC(OC=2C=C(C(F)=CC=2)C=2C3=CC=CC(Cl)=C3N=C(C)C=2)=C1 WBCYHJJQXUSRSD-UHFFFAOYSA-N 0.000 claims 1
- TXMYIUFOVCNBNJ-UHFFFAOYSA-N 8-cyano-4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C(N)=O)C#N)=C1 TXMYIUFOVCNBNJ-UHFFFAOYSA-N 0.000 claims 1
- JTEVUVYURIYBRA-UHFFFAOYSA-N 8-fluoro-4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(F)=C3N=CC=2)=C1 JTEVUVYURIYBRA-UHFFFAOYSA-N 0.000 claims 1
- XKPNHROGCHUKLN-UHFFFAOYSA-N 8-fluoro-4-[3-(3-methylsulfonylphenyl)phenyl]quinoline Chemical compound CS(=O)(=O)C1=CC=CC(C=2C=C(C=CC=2)C=2C3=CC=CC(F)=C3N=CC=2)=C1 XKPNHROGCHUKLN-UHFFFAOYSA-N 0.000 claims 1
- WUGCUIMHGIMUEX-UHFFFAOYSA-N 8-methoxy-4-[3-(3-methylsulfonylphenyl)phenyl]quinoline Chemical compound C1=CN=C2C(OC)=CC=CC2=C1C(C=1)=CC=CC=1C1=CC=CC(S(C)(=O)=O)=C1 WUGCUIMHGIMUEX-UHFFFAOYSA-N 0.000 claims 1
- GRPQJFRTFBPJTC-UHFFFAOYSA-N 8-methoxy-4-[3-(3-propan-2-ylsulfonylphenoxy)phenyl]quinoline Chemical compound C1=CN=C2C(OC)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(=O)(=O)C(C)C)=C1 GRPQJFRTFBPJTC-UHFFFAOYSA-N 0.000 claims 1
- JAGPCBYKLKIANY-UHFFFAOYSA-N 8-methyl-4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline Chemical compound C1=CN=C2C(C)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(C)(=O)=O)=C1 JAGPCBYKLKIANY-UHFFFAOYSA-N 0.000 claims 1
- XBDCCVVGSIGGTL-UHFFFAOYSA-N 8-methyl-4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline-3-carboxamide Chemical compound NC(=O)C1=CN=C2C(C)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(C)(=O)=O)=C1 XBDCCVVGSIGGTL-UHFFFAOYSA-N 0.000 claims 1
- ABRGSBDQNNWQCM-UHFFFAOYSA-N 8-methyl-4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline-3-carboxylic acid Chemical compound OC(=O)C1=CN=C2C(C)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(C)(=O)=O)=C1 ABRGSBDQNNWQCM-UHFFFAOYSA-N 0.000 claims 1
- OMRZJADIOZUUMD-UHFFFAOYSA-N 8-methyl-4-[3-(3-propan-2-ylsulfonylphenoxy)phenyl]quinoline Chemical compound CC(C)S(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(C)=C3N=CC=2)=C1 OMRZJADIOZUUMD-UHFFFAOYSA-N 0.000 claims 1
- ODZIMWSYAGRMNM-UHFFFAOYSA-N 8-methylsulfonyl-4-[3-(3-methylsulfonylphenyl)phenyl]quinoline Chemical compound CS(=O)(=O)C1=CC=CC(C=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2)S(C)(=O)=O)=C1 ODZIMWSYAGRMNM-UHFFFAOYSA-N 0.000 claims 1
- MTYQVMOMEWENQX-UHFFFAOYSA-N N-ethyl-3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenyl]benzenesulfonamide Chemical compound CCNS(=O)(=O)c1cccc(c1)-c1cccc(c1)-c1c(C)cnc2c(cccc12)C(F)(F)F MTYQVMOMEWENQX-UHFFFAOYSA-N 0.000 claims 1
- RKGUCTQUPQWZOT-UHFFFAOYSA-N [4-[3-(3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinolin-3-yl]methanamine Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2CN)C(F)(F)F)=C1 RKGUCTQUPQWZOT-UHFFFAOYSA-N 0.000 claims 1
- MVLGJDAVFKAYAE-UHFFFAOYSA-N benzyl 4-[3-[3-[8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]sulfanylpiperidine-1-carboxylate Chemical compound C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC(C=1)=CC=CC=1SC(CC1)CCN1C(=O)OCC1=CC=CC=C1 MVLGJDAVFKAYAE-UHFFFAOYSA-N 0.000 claims 1
- ONNVYGYELGWUEJ-UHFFFAOYSA-N benzyl 4-[3-[3-[8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]sulfonylpiperidine-1-carboxylate Chemical compound C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC(C=1)=CC=CC=1S(=O)(=O)C(CC1)CCN1C(=O)OCC1=CC=CC=C1 ONNVYGYELGWUEJ-UHFFFAOYSA-N 0.000 claims 1
- YWSKTMKEHLXONK-UHFFFAOYSA-N benzyl 4-[3-[3-[8-(trifluoromethyl)quinolin-4-yl]phenyl]phenyl]sulfanylpiperidine-1-carboxylate Chemical compound C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1C(C=1)=CC=CC=1SC(CC1)CCN1C(=O)OCC1=CC=CC=C1 YWSKTMKEHLXONK-UHFFFAOYSA-N 0.000 claims 1
- DDJNOHWFVIFZLI-UHFFFAOYSA-N benzyl 4-[3-[3-[8-(trifluoromethyl)quinolin-4-yl]phenyl]phenyl]sulfonylpiperidine-1-carboxylate Chemical compound C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1C(C=1)=CC=CC=1S(=O)(=O)C(CC1)CCN1C(=O)OCC1=CC=CC=C1 DDJNOHWFVIFZLI-UHFFFAOYSA-N 0.000 claims 1
- PFGKZIFECFSGMT-UHFFFAOYSA-N ethyl 4-[3-[3-(3-aminopropylsulfonyl)phenyl]phenyl]-8-(trifluoromethyl)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1C1=CC=CC(S(=O)(=O)CCCN)=C1 PFGKZIFECFSGMT-UHFFFAOYSA-N 0.000 claims 1
- CIANMBBVJFDYPQ-UHFFFAOYSA-N ethyl 4-[5-(3-methylsulfonylphenyl)thiophen-2-yl]-8-(trifluoromethyl)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 CIANMBBVJFDYPQ-UHFFFAOYSA-N 0.000 claims 1
- VXXKJCBHYXFMGL-UHFFFAOYSA-N ethyl 4-[5-[5-(3-methylsulfonylphenyl)thiophen-2-yl]thiophen-2-yl]-8-(trifluoromethyl)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(S1)=CC=C1C(S1)=CC=C1C1=CC=CC(S(C)(=O)=O)=C1 VXXKJCBHYXFMGL-UHFFFAOYSA-N 0.000 claims 1
- ASYHCAAQWWZYAG-UHFFFAOYSA-N ethyl n-[3-[3-(8-chloro-3-methylquinolin-4-yl)phenoxy]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=CC=2C)=C1 ASYHCAAQWWZYAG-UHFFFAOYSA-N 0.000 claims 1
- DLVMCWPOXNXONH-UHFFFAOYSA-N methyl 4-[3-(3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinoline-3-carboxylate Chemical compound COC(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(C)(=O)=O)=C1 DLVMCWPOXNXONH-UHFFFAOYSA-N 0.000 claims 1
- MIESWKZAQLLAKI-UHFFFAOYSA-N methyl 4-[3-(3-methylsulfonylphenoxy)phenyl]quinoline-8-carboxylate Chemical compound C1=CN=C2C(C(=O)OC)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(C)(=O)=O)=C1 MIESWKZAQLLAKI-UHFFFAOYSA-N 0.000 claims 1
- ANRXHSGXLIYWML-UHFFFAOYSA-N methyl n-[3-[3-(8-chloro-3-methylquinolin-4-yl)phenoxy]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=CC=2C)=C1 ANRXHSGXLIYWML-UHFFFAOYSA-N 0.000 claims 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N methylquinoline Natural products C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims 1
- VZONGKKLJJHNOT-UHFFFAOYSA-N n,n-bis[(4-methoxyphenyl)methyl]-3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1CN(S(=O)(=O)C=1C=C(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)C=CC=1)CC1=CC=C(OC)C=C1 VZONGKKLJJHNOT-UHFFFAOYSA-N 0.000 claims 1
- HZLMHMBEWNIOIC-UHFFFAOYSA-N n,n-bis[(4-methoxyphenyl)methyl]-4-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1CN(S(=O)(=O)C=1C=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=CC=1)CC1=CC=C(OC)C=C1 HZLMHMBEWNIOIC-UHFFFAOYSA-N 0.000 claims 1
- HMDLRORXNBINQC-UHFFFAOYSA-N n,n-bis[(4-methoxyphenyl)methyl]-4-[3-[8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1CN(S(=O)(=O)C=1C=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=CC=1)CC1=CC=C(OC)C=C1 HMDLRORXNBINQC-UHFFFAOYSA-N 0.000 claims 1
- IXFFIQGAGXFVQX-UHFFFAOYSA-N n-(2-fluoroethyl)-3-[3-[3-[8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]sulfonylpropan-1-amine Chemical compound FCCNCCCS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=C1 IXFFIQGAGXFVQX-UHFFFAOYSA-N 0.000 claims 1
- VURGQNRVFBORKB-UHFFFAOYSA-N n-(2-hydroxy-2-methylpropyl)-n-methyl-3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound CC(O)(C)CN(C)S(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 VURGQNRVFBORKB-UHFFFAOYSA-N 0.000 claims 1
- QVBIXBVVTUJYMT-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound CC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(=O)(=O)NCCO)=C1 QVBIXBVVTUJYMT-UHFFFAOYSA-N 0.000 claims 1
- YWJBNSJSZKBCOQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methyl-3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound OCCN(C)S(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 YWJBNSJSZKBCOQ-UHFFFAOYSA-N 0.000 claims 1
- QGOKRDOWCZJLBX-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methyl-3-[[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenyl]methyl]benzenesulfonamide Chemical compound OCCN(C)S(=O)(=O)C1=CC=CC(CC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 QGOKRDOWCZJLBX-UHFFFAOYSA-N 0.000 claims 1
- IWFFUODRXZGVGF-UHFFFAOYSA-N n-(2-hydroxypropyl)-3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound CC(O)CNS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 IWFFUODRXZGVGF-UHFFFAOYSA-N 0.000 claims 1
- LFHAMUBPHSQFQL-UHFFFAOYSA-N n-(2-methoxy-2-methylpropyl)-3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound COC(C)(C)CNS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 LFHAMUBPHSQFQL-UHFFFAOYSA-N 0.000 claims 1
- IBORPXQXVHIBGU-UHFFFAOYSA-N n-(2-methoxy-2-methylpropyl)-n-methyl-3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound COC(C)(C)CN(C)S(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 IBORPXQXVHIBGU-UHFFFAOYSA-N 0.000 claims 1
- PXJOQMCXFIRYTG-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]-3-[3-[3-[8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]sulfonylpropan-1-amine Chemical compound C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC(C=1)=CC=CC=1S(=O)(=O)CCCNCC1=CC=CC(Cl)=C1 PXJOQMCXFIRYTG-UHFFFAOYSA-N 0.000 claims 1
- PYKMQNNQUWEOOX-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-[3-[3-[8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]sulfonylpropan-1-amine Chemical compound C1=CC(F)=CC=C1CNCCCS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=C1 PYKMQNNQUWEOOX-UHFFFAOYSA-N 0.000 claims 1
- MVPYZESGZJMOFK-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-n-methyl-3-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1CN(C)S(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 MVPYZESGZJMOFK-UHFFFAOYSA-N 0.000 claims 1
- ZYOZKZFIAYJNJS-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-n-methyl-4-[3-[3-methyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1CN(C)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC(C=2C3=CC=CC(=C3N=CC=2C)C(F)(F)F)=C1 ZYOZKZFIAYJNJS-UHFFFAOYSA-N 0.000 claims 1
- KUCGAMZFDRXPPO-UHFFFAOYSA-N n-[3-[3-(8-chloro-3-methylquinolin-4-yl)phenoxy]phenyl]benzenesulfonamide Chemical compound CC1=CN=C2C(Cl)=CC=CC2=C1C(C=1)=CC=CC=1OC(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 KUCGAMZFDRXPPO-UHFFFAOYSA-N 0.000 claims 1
- YPADPIALCHYXBO-UHFFFAOYSA-N n-[3-[3-(8-chloro-3-methylquinolin-4-yl)phenoxy]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(Cl)=C3N=CC=2C)=C1 YPADPIALCHYXBO-UHFFFAOYSA-N 0.000 claims 1
- JNLDEHXZYWKVRY-UHFFFAOYSA-N n-[3-[3-(8-chloro-3-methylquinolin-4-yl)phenoxy]phenyl]methanesulfonamide Chemical compound CC1=CN=C2C(Cl)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(NS(C)(=O)=O)=C1 JNLDEHXZYWKVRY-UHFFFAOYSA-N 0.000 claims 1
- LGKPARYIEKQSAA-UHFFFAOYSA-N n-[3-[3-[3-[8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]sulfonylpropyl]acetamide Chemical compound CC(=O)NCCCS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=C1 LGKPARYIEKQSAA-UHFFFAOYSA-N 0.000 claims 1
- QTLVXTLZQQVJRO-UHFFFAOYSA-N n-[3-[3-[3-[8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]sulfonylpropyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCCS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=C1 QTLVXTLZQQVJRO-UHFFFAOYSA-N 0.000 claims 1
- MWBLBJWLAVHPCU-UHFFFAOYSA-N n-[3-[3-[3-cyano-8-(trifluoromethyl)quinolin-4-yl]phenyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2C#N)C(F)(F)F)=C1 MWBLBJWLAVHPCU-UHFFFAOYSA-N 0.000 claims 1
- IOVDFYSLDOTXLI-UHFFFAOYSA-N n-[4-[3-(3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinolin-3-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CN=C2C(C(F)(F)F)=CC=CC2=C1C(C=1)=CC=CC=1OC1=CC=CC(S(C)(=O)=O)=C1 IOVDFYSLDOTXLI-UHFFFAOYSA-N 0.000 claims 1
- YJAGXGJQDHHFSC-UHFFFAOYSA-N n-[4-[3-[3-cyano-8-(trifluoromethyl)quinolin-4-yl]phenyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CC=CC(C=2C3=CC=CC(=C3N=CC=2C#N)C(F)(F)F)=C1 YJAGXGJQDHHFSC-UHFFFAOYSA-N 0.000 claims 1
- AJPBCXPFQOSMIN-UHFFFAOYSA-N n-[[4-[3-(3-methylsulfonylphenoxy)phenyl]-8-(trifluoromethyl)quinolin-3-yl]methyl]cyclopentanamine Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C=C(C=CC=2)C=2C3=CC=CC(=C3N=CC=2CNC2CCCC2)C(F)(F)F)=C1 AJPBCXPFQOSMIN-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
-
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A—HUMAN NECESSITIES
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- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- 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
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Definitions
- R 2 is:
- X is -C(O)-; -O-; -S(O) r , wherein t is 0-2; -NR 9 -; -C(O)NR 9 -; -C(NH)NR 9 ; -C(O)O-; -CH 2 O-; -NR 9 SO 2 -; or -SO 2 NR 9 -, wherein R 9 is hydrogen or Ci-C 6 alkyl; and R 8 is:
- W at each occurrence is, independently, a bond; -O-; -S(O) t -, wherein t is 0-2; -NR 9 -; -C(O)NR 9 -; Ci_ 6 alkylene; or C 2 . 6 alkynylene; -W 1 Cd -6 alkylene)-; or -(Ci_ 6 alkylene ⁇ 1 -; W 1 at each occurrence is, independently, -O-; -S(O) r , wherein t is 0-2;
- a at each occurrence is, independently: (i) C 6 -Ci 0 aryl, which is: (a) substituted with from 1-5 (e.g., 1-4, 1-3, 1-2, or 1, e.g., 1-2) R f ; and
- R 1 is hydrogen or Ci-Ce alkyl
- Example 43 the title compound of Example 43 is "4- ⁇ 3-[3-(ethylsulfonyl)phenoxy]phenyl ⁇ -3-methyl-8-(trifluoromethyl)quinoline," and one of the title compounds of Example 397 is "4-[3'-(ethylsulfonyl)-4'-methylbiphenyl-3-yl]-3- methyl-8-(trifluoromethyl)quinoline.”
- the invention also relates generally to modulating (e.g., activating) LXRs with the quinoline compounds described herein.
- the methods can include, e.g., contacting an LXR in a sample (e.g., a tissue, a cell free assay medium, a cell-based assay medium) with a compound of formula (I) (including any subgenera or specific compounds thereof).
- the methods can include administering a compound of formula (I) (including any subgenera or specific compounds thereof) to a subject (e.g., a mammal, e.g., a human, e.g., a human having or at risk of having one or more of the diseases or disorders described herein).
- this invention relates to methods of modulating (e.g., increasing) reverse cholesterol transport in a subject (e.g., a subject in need thereof), which includes administering to the subject an effective amount of a compound of formula (I) (including any subgenera or specific compounds thereof) or a pharmaceutically acceptable salt or prodrug thereof.
- a at each occurrence is, independently, arylsulfinylcyclyl, heteroarylsulfinylcyclyl, arylsulfonylcyclyl or heteroarylsulfonylcyclyl, each of which includes 8-10 atoms and is optionally substituted with from 1 -4 R e ; or
- R A22 , R A23 , R A24 , and R A25 is provided that only one of R A22 , R A23 , R A24 , and R A25 is
- A can be benzo[b]thienyl- 1,1 -dioxide, 3,4-dihydro-2H-thiopyrano[2,3-b]pyridyl-l,l- dioxide, or 2,3-dihydrobenzo[b]thienyl- 1,1 -dioxide, each of which is optionally substituted with from 1-3 R e .
- R 3 can have formula D-I;
- R 32 can be hydrogen or R e (e.g., halo, e.g., fluoro, or chloro); and
- R e at each occurrence can be, independently, halo; C 1 -C 3 alkyl, optionally substituted with from 1-2 R a ; C 1 -C 3 haloalkyl; C 1 -C 3 alkoxy; hydroxyl; nitro; cyano; NR s R h ; phenyl; or 4-fluorophenyl.
- the hydrogen atoms can each be replaced by the same halogen (e.g., fluoro) or the hydrogen atoms can be replaced by a combination of different halogens (e.g., fluoro and chloro).
- Haloalkyl also includes alkyl moieties in which all hydrogens have been replaced by halo (e.g., perhaloalkyl, e.g., perfluoroalkyl, such as trifluoromethyl).
- heterocyclyl refers to a saturated monocyclic, bicyclic, tricyclic or other polycyclic ring system having 1-4 heteroatoms if monocyclic, 1-8 heteroatoms if bicyclic, or 1-10 heteroatoms if tricyclic, said heteroatoms selected from O, N, or S (and mono and dioxides thereof, e.g., N ⁇ O ⁇ , S(O), SO 2 ).
- heterocycloalkenyl refers to partially unsaturated monocyclic, bicyclic, tricyclic, or other polycyclic hydrocarbon groups having 1-4 heteroatoms if monocyclic, 1-8 heteroatoms if bicyclic, or 1-10 heteroatoms if tricyclic, said heteroatoms selected from O, N, or S (and mono and dioxides thereof, e.g., N ⁇ O ⁇ , S(O), SO 2 ) (e.g., carbon atoms and 1-4, 1-8, or 1-10 heteroatoms of N, O, or S if monocyclic, bicyclic, or tricyclic, respectively).
- R can be hydrogen
- R 2 can be heteroaryl including 5-10atoms that is optionally substituted with from 1-3 (e.g., 1-2, 1) R d (e.g., C r C 3 alkyl; C r C 3 haloalkyl, e.g., Q-C 3 perfluoroalkyl; halogen; CN; NR s R h ; or Ci-C 3 alkoxy).
- R d e.g., C r C 3 alkyl; C r C 3 haloalkyl, e.g., Q-C 3 perfluoroalkyl; halogen; CN; NR s R h ; or Ci-C 3 alkoxy.
- X can be -NR 9 -, thereby forming an amino moiety of the formula -NR 8 R 9 .
- R 9 can be hydrogen or Ci-C 6 (e.g., Ci-C 4 ) alkyl, and R 8 can be as defined anywhere herein. In certain embodiment, R 8 and R 9 can both be hydrogen.
- W can be -O-.
- A can be C 6 -Ci 0 aryl, which is (i) substituted with from 1-3 (e.g., 1-2, 1) R f and (ii) optionally substituted with 1 or 2 R e .
- A can have formula (B- ), in which the phenyl ring is substituted with (a) 1 R f and (b) 2 R e : (B-8)
- A can have formula (B-9):
- R A24 can be R f (e.g., -SO 2 R n ), and each of R ⁇ 2 , R ⁇ 3 , and R A25 can be hydrogen.
- R ⁇ 4 can be R f (e.g., -SO 2 R n ), one of R A22 , R A23 , and R A25 (e.g., R A22 ) can be R e , and the other two can each be hydrogen.
- A can be tetrahydroquinolyl or tetrahydroisoquinolyl, which is substituted with 1 R f .
- W can be attached to the aromatic ring portion of the tetrahydroquinolyl or tetrahydroisoquinolyl ring (e.g., the 5-position).
- R f can be attached to the tetrahydroquinolyl or tetrahydroisoquinolyl nitrogen ring atom (e.g., when R f is SO 2 R n ).
- R e at each occurrence can be, independently, halo; C 1 -C 3 alkyl, optionally substituted with from 1-2 R a (e.g., R a can be C(O)NR s R h ); hydroxyl; cyano; or nitro.
- 0x0 and optionally substituted with from 1-3 (e.g., 1-2, 1) R e ; and/or
- R n can be Ci-Ci 0 (e.g., Ci-C 5 or Ci-C 3 ) haloalkyl.
- R n can be CF 3 or CH 2 CH 2 CH 2 Cl.
- R n can be branched or unbranched Ci-C 8 (e.g., Ci, C 2 , or C 3 ) alkyl, which is substituted with 1 R a .
- R a can be: (i) hydroxyl; or
- C 2 -CiO alkenyl or C 2 -C 2 O alkynyl e.g., C 3 alkenyl or alkynyl
- C 7 -C 20 aralkyl e.g., benzyl
- halo e.g., fluoro or chloro
- C 7 -C 20 e.g., C 7 -Ci 0
- aralkyl e.g., benzyl
- halo e.g., fluoro or chloro
- one of R s and R h can be hydrogen or Ci-C 3 alkyl; and the other can be:
- R s and R h can both be: (i) hydrogen; or
- R n can be heterocyclyl including 5-10 (e.g., 5-8, 5-6) atoms, optionally substituted with from 1-5 (e.g., 1-4, 1-3, 1-2, 1, e.g., 1) R b .
- R n can be C 2 -C 6 alkenyl (e.g., allyl, 1-propenyl), optionally substituted with from 1-2 R c .
- R f can be -NR k S(O) n R n .
- R k can be hydrogen.
- R n can be Ci-C 6 alkyl (CH 3 , CH 2 CH 3 ), optionally substituted with from 1-2 R a ; or C 6 -Ci 0 (e.g., phenyl) aryl, optionally substituted with from 1- 2 R d (e.g., CH 3 ).
- R f can be -NR k C(O)OR J or -NR k C(O)NR s R h .
- R k can be hydrogen.
- R s , R h , and R can each be, independently of one another, hydrogen; Ci-Ce alkyl, optionally substituted with from 1-2 R a (e.g., chloro) or C 6 -Ci 0 aryl, optionally substituted with from 1-2 R d (e.g., CH 3 ).
- R J can be Ci-C 6 alkyl, optionally substituted with from 1-2 R a (e.g., chloro).
- one of R s and R h can be hydrogen.
- heterocyclyl including 5-7 atoms that is substituted with 1 oxo and optionally substituted with from 1 -2 R e ;
- R 7 can be chloro or bromo (e.g., chloro); cyano, Ci-Ci 0 (e.g., Q-C 6 , Ci-C 3 ) alkyl, or Q-Q 0 (e.g., Q-C 6 , Q-C 3 ) haloalkyl, or SO 2 R m
- R 7 can be halo (e.g., fluoro or chloro, e.g., chloro).
- Another subset of compounds includes those in which R has formula D- 1 :
- R 3 has formula (A-4); and W is a bond;
- Another subset of compounds includes those in which:
- W can be a bond; -O-; Ci_ 3 alkylene (e.g., -CH 2 -); C 2 ⁇ alkynylene (e.g., -C ⁇ C-); - O(Ci_3 alkylene)- (e.g., -OCH 2 -); or -(Ci -3 alkylene)O- (e.g., -CH 2 O-);
- R f can be:
- R e can be hydrogen; halo; C 1 -C 3 alkyl, optionally substituted with from 1-2 R a ; C 1 - C3 haloalkyl; C 1 -C3 alkoxy; hydroxyl; cyano; nitro; NR s R h ; phenyl; or 4-fluorophenyl.
- R e can be hydrogen; halo; Ci-Ce alkyl, optionally substituted with from 1-2 R a (e.g., R a can be C(O)NR s R h ); C 1 -C 3 haloalkyl; C 1 -C 3 alkoxy; NR s R h ; phenyl; or 4- fluorophenyl.
- R e can be hydrogen; halo; C 1 -C 3 alkyl, optionally substituted with from 1-2 R a (e.g., R a can be C(O)NR s R h ); hydroxyl; cyano; or nitro.
- halogen is a fluorine or chlorine
- an aromatic displacement is typically performed, usually in a polar, aprotic solvent such as DMF, DSMO, and the like in the presence of a base, e.g., potassium carbonate or cesium carbonate, at elevated temperatures, typically from about 100-150 0 C for several hours to several days.
- a base e.g., potassium carbonate or cesium carbonate
- a coupling procedure using a copper salt e.g., CuI
- a ligand such as N,N-dimethylglycine or L-proline
- a solvent such as 1,4-dioxane.
- halogenated thiophenols can be alkylated with an alkylating agent in the presence of a base, typically potassium carbonate, in an appropriate solvent such as acetone.
- a base typically potassium carbonate
- the reaction is typically heated at 40 to 65°C for 1-4 h, cooled, and treated with aqueous sodium bicarbonate and Oxone. After 18-48 h, the desired halogenated arylsulfones is isolated (Scheme 3).
- halogenated arylsulfonamides can be prepared by reaction of halogenated arylsulfonyl chlorides with amines (Scheme 5).
- biarylethers can be prepared by displacement reactions between 4-(3-hydroxyphenyl)-quino lines and halogenated arylsulfones in which the halogen is preferably fluorine or chlorine.
- the reactions are typically heated at 100 to 150 0 C in a polar solvent such as DMF, DMSO, and N-methylpyrrolidine for several hours to several days (Scheme 6).
- biarylethers can be synthesized by a coupling reaction between 4-(3-hydroxyphenyl)-quino lines and halogenated arylsulfones where the halogen is preferably bromine or iodine.
- the reactions are typically heated at 100 to 150 0 C in a polar solvent such as DMSO, for several hours to several days, with a copper solubilizing reagent such as L-proline (Scheme 7).
- the quinoline-biarylether-methylsulfones described herein can be further elaborated by forming the anion of the methylsulfone, typically using a strong base such as n-butyl lithium of sec-butyl lithium in a solvent such as ether or THF, typically at 0 0 C to ambient temperatures, followed by addition of an epoxide to form the 3- hydroxypropylsulfone as shown in Scheme 8 below.
- biarylethers with sulfonamide groups can be prepared by displacement reactions between 4-(3-hydroxyphenyl)-quino lines and halogenated arylsulfonamides where the halogen is preferably fluorine.
- the reactions are typically heated at 100 to 150 0 C in a polar solvent such as DMF, DMSO, or N-methylpyrrolidine for 2 hours to 2 days (Scheme 9).
- alkylation of 4-(3-hydroxyphenyl)-quinolines with arylalkylhalides (aralkyl halides) in a solvent such as acetonitrile or DMF in the presence of a base, typically cesium carbonate or potassium carbonate, generally with heating at reflux for 6 to 24 hours, can provide the benzylsulfone substitution as shown in Scheme 11.
- Preparation of quino line-aryl-CH 2 O-arylsulfones or quino line-aryl-CH 2 O- arylsulfonamides can be accomplished by conversion of a 4-(3-hydroxymethylphenyl) quinoline into the corresponding bromide by conventional methods, e.g., reaction with a brominating agent such as phosphorous tribromide in a solvent such as dichloromethane or the like.
- a phenol (or heterophenol) can be alkylated with the benyzlic bromide under typical alkylation conditions as described in Scheme 11 above or using other conditions such as sodium hydride or other base in the presence of a solvent such as DMF or THF (Scheme 12).
- pyridine-sulfone can be prepared by the copper- induced coupling of 3-bromo-5-(methylsulfonyl)pyridine with a 4-(3-hydroxyphenyl)quinoline, typically using CuI in the presence of N,N-dimethylglycine hydrochloride in the presence of a base such as cesium carbonate in 1 ,4-dioxane at elevated temperature, typically at reflux (Scheme 21).
- Quinoline biarylethers containing substitutents NHSO 2 R 11 , NHC(O)OR, and NHC(0)NHR h can be prepared by reacting a fluoronitrobenzene with a quinoline -phenol in a polar solvent such as DMF or DMA in the presence of a base, typically potassium carbonate at elevated temperatures, typically 80 - 150 0 C, for typically 4 to 24 hours.
- the nitro group is reduced in the product, typically with tin metal in hydrochloric acid with a cosolvent such as methanol or ethanol, or by hydrogenation with a palladium catalyst where applicable.
- oxadiazoles can be prepared by the reaction of an ester with an amino-oxime as in Scheme 29.
- imidazolines can be prepared by reaction of an ester with a diamine as in Scheme 30.
- the title compound was prepared using 3-fluorobenzenesulfonyl chloride as the arylsulfonyl chloride and cyclopenyliodide as the alkylating agent.
- the title compound was prepared using 4-fluorobenzenesulfonyl chloride as the arylsulfonyl chloride and ethyl 2-(4-(bromomethyl)phenyl)acetate as the alkylating agent.
- Example 34 2,5-dimethylbenzyl-4-fhiorophenyl sulfone
- the title compound was prepared using 4-fluorobenzenesulfonyl chloride as the arylsulfonyl chloride and 2-(bromomethyl)-l,4-dimethylbenzene as the alkylating agent.
- the title compound was prepared using 3-fluorobenzenethiol as the as the thiophenol and iodomethane as the alkylating agent.
- Example 67 3-benzyl-4- ⁇ 3-[4-(methylsulfonyl)phenoxy]phenyl ⁇ -8-(trifluoromethyl)quinoline MS (ES) m/z 533.8.
- Example 68 3-benzyl-4- ⁇ 3-[3-(isobutylsulfonyl)phenoxy]phenyl ⁇ -8-(trifluoromethyl)quinoline
- Example 84 4- ⁇ 3-[3-(ethylsulfonyl)phenoxy]phenyl ⁇ -8-(trifluoromethyl)quinoline mp 147 0 C; MS (ES) m/z 457.9; HRMS: calcd for C 24 H 18 F 3 NO 3 S + H+, 458.10322; found (ESI, [M+H] + ), 458.1019.
- Example 110 4- ⁇ 3-[4-methyl-3-(methylsulfonyl)phenoxy]phenyl ⁇ -8-(trifluoromethyl)quinoline mp 147-149 0 C; MS (ES) m/z 457.8.
- Example 125 is the same compound as Example 1 10 but using the method described in Example 124.
- Example 127 In a similar manner to that described for Example 127 above, the following compounds were prepared using the corresponding halogenated arylsulfonamide and quinoline phenol, and eluting with an appropriate eluent, varying temperature based on substitution.
- meta-haloarylsulfonamides were subjected to higher temperatures, typically 150 0 C, while ortho- and para-haloarylsulfonamides can react at lower temperatures, typically 100 0 C to 150 0 C. In some instances, higher yields were obtained when R is not H.
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Abstract
Description
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EP07844372A EP2074098A2 (en) | 2006-10-18 | 2007-10-18 | Quinoline compounds |
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MX2009003942A MX2009003942A (en) | 2006-10-18 | 2007-10-18 | Quinoline compounds. |
JP2009533516A JP2010506954A (en) | 2006-10-18 | 2007-10-18 | Quinoline compounds |
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Cited By (28)
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WO2009021740A2 (en) | 2007-08-15 | 2009-02-19 | Sanofis-Aventis | Substituted tetrahydronaphthalenes, process for the preparation thereof and the use thereof as medicaments |
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CN103539734B (en) * | 2013-09-25 | 2015-10-14 | 上海交通大学 | The preparation method of 3-allyl group quinoline |
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Also Published As
Publication number | Publication date |
---|---|
TW200825054A (en) | 2008-06-16 |
JP2010506954A (en) | 2010-03-04 |
CL2007002996A1 (en) | 2008-06-13 |
AU2007311046A1 (en) | 2008-04-24 |
WO2008049047A3 (en) | 2008-07-24 |
CN101541751A (en) | 2009-09-23 |
CA2666508A1 (en) | 2008-04-24 |
MX2009003942A (en) | 2009-04-24 |
EP2074098A2 (en) | 2009-07-01 |
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