KR20060085675A - 이상지혈증 치료를 위한 화합물 및 방법 - Google Patents

Info

Publication number

KR20060085675A

KR20060085675A KR1020067006837A KR20067006837A KR20060085675A KR 20060085675 A KR20060085675 A KR 20060085675A KR 1020067006837 A KR1020067006837 A KR 1020067006837A KR 20067006837 A KR20067006837 A KR 20067006837A KR 20060085675 A KR20060085675 A KR 20060085675A

Authority

KR

South Korea

Prior art keywords

amino

trifluoromethyl

azepine

acetyl

tetrahydro

Prior art date

2003-10-08

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

• Espacenet
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 331
• 238000000034 method Methods 0.000 title claims abstract description 147
• 208000032928 Dyslipidaemia Diseases 0.000 title claims description 12
• 208000017170 Lipid metabolism disease Diseases 0.000 title claims description 12
• 150000003839 salts Chemical class 0.000 claims abstract description 44
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 26
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 325
• 239000000203 mixture Substances 0.000 claims description 230
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 104
• 230000002829 reductive effect Effects 0.000 claims description 93
• 125000000623 heterocyclic group Chemical group 0.000 claims description 57
• 229910052757 nitrogen Inorganic materials 0.000 claims description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 41
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 38
• 238000011282 treatment Methods 0.000 claims description 37
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 29
• 230000000694 effects Effects 0.000 claims description 28
• 239000012453 solvate Substances 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 25
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 24
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
• 125000004104 aryloxy group Chemical group 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• 125000004043 oxo group Chemical group O=* 0.000 claims description 16
• CEOOTVIRKQRQCV-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CEOOTVIRKQRQCV-UHFFFAOYSA-N 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 238000008214 LDL Cholesterol Methods 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 230000002265 prevention Effects 0.000 claims description 13
• 108010028554 LDL Cholesterol Proteins 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 12
• 101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 claims description 11
• 230000001575 pathological effect Effects 0.000 claims description 11
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 108010023302 HDL Cholesterol Proteins 0.000 claims description 9
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 208000008589 Obesity Diseases 0.000 claims description 5
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 235000020824 obesity Nutrition 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 4
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004494 ethyl ester group Chemical group 0.000 claims description 4
• 239000011593 sulfur Chemical group 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
• PTXMTGKCQWZCPM-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(C(F)(F)F)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PTXMTGKCQWZCPM-UHFFFAOYSA-N 0.000 claims description 3
• WPZSUMUHYRSTFL-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-chloro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(Cl)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WPZSUMUHYRSTFL-UHFFFAOYSA-N 0.000 claims description 3
• 238000011321 prophylaxis Methods 0.000 claims description 3
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 2
• PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical group [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 230000008485 antagonism Effects 0.000 claims description 2
• 230000002222 downregulating effect Effects 0.000 claims description 2
• LLEVICHHUOYYRX-UHFFFAOYSA-N ethyl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OCC)CCCC1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LLEVICHHUOYYRX-UHFFFAOYSA-N 0.000 claims description 2
• HFURXXNCQGEELO-UHFFFAOYSA-N ethyl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-7-bromo-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical class C12=CC(Br)=CC=C2N(C(=O)OCC)CCCC1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HFURXXNCQGEELO-UHFFFAOYSA-N 0.000 claims description 2
• SWKQBNNYQOEXGJ-UHFFFAOYSA-N ethyl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OCC)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SWKQBNNYQOEXGJ-UHFFFAOYSA-N 0.000 claims description 2
• DNHBLWZQCXEDIO-UHFFFAOYSA-N propan-2-yl 4-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1C2=CC(C(F)(F)F)=CC=C2N(C(=O)OC(C)C)CCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DNHBLWZQCXEDIO-UHFFFAOYSA-N 0.000 claims description 2
• OJBVLLYNOIAHSN-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)C)C2=CC=C(C(F)(F)F)C=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OJBVLLYNOIAHSN-UHFFFAOYSA-N 0.000 claims description 2
• XWMINHIEXQWWII-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-7-bromo-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)C)C2=CC=C(Br)C=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XWMINHIEXQWWII-UHFFFAOYSA-N 0.000 claims description 2
• MQIZICRKQSYLHY-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MQIZICRKQSYLHY-UHFFFAOYSA-N 0.000 claims description 2
• KSYXXQMGFSWKMO-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-fluoro-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=C(F)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 KSYXXQMGFSWKMO-UHFFFAOYSA-N 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 claims 3
• 102100037637 Cholesteryl ester transfer protein Human genes 0.000 claims 3
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
• 239000005557 antagonist Substances 0.000 claims 1
• RKCWETOXNKAHRO-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-4,4-dimethyl-7-(trifluoromethyl)-3,5-dihydro-2h-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OC(C)C)CCC(C)(C)C1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RKCWETOXNKAHRO-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 626
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 279
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 266
• 235000019439 ethyl acetate Nutrition 0.000 description 207
• 239000000243 solution Substances 0.000 description 149
• 239000002904 solvent Substances 0.000 description 148
• 238000002360 preparation method Methods 0.000 description 121
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 112
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 99
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• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 95
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 84
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• 239000012044 organic layer Substances 0.000 description 82
• 239000012267 brine Substances 0.000 description 79
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 79
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 77
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
• 230000015572 biosynthetic process Effects 0.000 description 72
• 238000006243 chemical reaction Methods 0.000 description 70
• 238000003786 synthesis reaction Methods 0.000 description 70
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 66
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 56
• 239000000741 silica gel Substances 0.000 description 54
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• 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 description 49
• 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 description 49
• 229910052938 sodium sulfate Inorganic materials 0.000 description 49
• 235000011152 sodium sulphate Nutrition 0.000 description 49
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
• 239000003153 chemical reaction reagent Substances 0.000 description 48
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 41
• 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 description 39
• VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 38
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 38
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• 238000003756 stirring Methods 0.000 description 31
• 239000003921 oil Substances 0.000 description 30
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• LVKIESWJKHVPIN-UHFFFAOYSA-N azepine-1-carboxylic acid Chemical compound OC(=O)N1C=CC=CC=C1 LVKIESWJKHVPIN-UHFFFAOYSA-N 0.000 description 29
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 29
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 27
• VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 27
• 239000012299 nitrogen atmosphere Substances 0.000 description 26
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• 238000003818 flash chromatography Methods 0.000 description 25
• 239000000706 filtrate Substances 0.000 description 23
• FTXHIVWBDJEPSZ-UHFFFAOYSA-N propan-2-yl azepine-1-carboxylate Chemical compound CC(C)OC(=O)N1C=CC=CC=C1 FTXHIVWBDJEPSZ-UHFFFAOYSA-N 0.000 description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
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• 229960000583 acetic acid Drugs 0.000 description 15
• 150000002632 lipids Chemical class 0.000 description 15
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• 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 14
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• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
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• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 12
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• LQHITAZWAJOHKO-UHFFFAOYSA-N methyl 2-[(4-ethoxy-4-oxobutyl)-propan-2-yloxycarbonylamino]-6-fluorobenzoate Chemical compound CCOC(=O)CCCN(C(=O)OC(C)C)C1=CC=CC(F)=C1C(=O)OC LQHITAZWAJOHKO-UHFFFAOYSA-N 0.000 description 2
• HTPZAAMADGUHKJ-UHFFFAOYSA-N methyl 2-[(4-ethoxy-4-oxobutyl)-propan-2-yloxycarbonylamino]-6-methylbenzoate Chemical compound CCOC(=O)CCCN(C(=O)OC(C)C)C1=CC=CC(C)=C1C(=O)OC HTPZAAMADGUHKJ-UHFFFAOYSA-N 0.000 description 2
• WRMXVYXQRBFGGP-UHFFFAOYSA-N methyl 2-[(4-methoxy-4-oxobutyl)-[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-(trifluoromethyl)benzoate Chemical compound COC(=O)CCCN(C(=O)OC(C)(C)C)C1=CC=C(C(F)(F)F)C=C1C(=O)OC WRMXVYXQRBFGGP-UHFFFAOYSA-N 0.000 description 2
• GUYWKWAFWXEKFU-UHFFFAOYSA-N methyl 2-[(4-methoxy-4-oxobutyl)-[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-methyl-4-(trifluoromethoxy)benzoate Chemical compound COC(=O)CCCN(C(=O)OC(C)(C)C)C1=CC(OC(F)(F)F)=C(C)C=C1C(=O)OC GUYWKWAFWXEKFU-UHFFFAOYSA-N 0.000 description 2
• RNGGLSYTTUHJIO-UHFFFAOYSA-N methyl 2-[(4-methylphenyl)sulfonylamino]-5-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC(C(F)(F)F)=CC=C1NS(=O)(=O)C1=CC=C(C)C=C1 RNGGLSYTTUHJIO-UHFFFAOYSA-N 0.000 description 2
• COTQUWGKILPGMY-UHFFFAOYSA-N methyl 2-amino-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=CC(C(F)(F)F)=C1N COTQUWGKILPGMY-UHFFFAOYSA-N 0.000 description 2
• ZPXIVPLXMVFFKP-UHFFFAOYSA-N methyl 2-amino-5-bromo-4-chlorobenzoate Chemical compound COC(=O)C1=CC(Br)=C(Cl)C=C1N ZPXIVPLXMVFFKP-UHFFFAOYSA-N 0.000 description 2
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• GEXXXHIFKGCKOJ-UHFFFAOYSA-N methyl 2-fluoro-6-(propan-2-yloxycarbonylamino)benzoate Chemical compound COC(=O)C1=C(F)C=CC=C1NC(=O)OC(C)C GEXXXHIFKGCKOJ-UHFFFAOYSA-N 0.000 description 2
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• DVKDTXRSCIAOFN-UHFFFAOYSA-N methyl 4-(propan-2-yloxycarbonylamino)-2,3-dihydro-1h-indene-5-carboxylate Chemical compound COC(=O)C1=CC=C2CCCC2=C1NC(=O)OC(C)C DVKDTXRSCIAOFN-UHFFFAOYSA-N 0.000 description 2
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• INBMKFKLRKILSD-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methylamino]-6-fluoro-7-methyl-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=C(F)C(C)=CC=C2N(C(=O)OC(C)C)CCCC1NCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 INBMKFKLRKILSD-UHFFFAOYSA-N 0.000 description 1
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• QPXMOLDCXLPFIU-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2,3,4,5-tetrahydrobenzo[h][1]benzazepine-1-carboxylate Chemical compound C12=CC3=CC=CC=C3C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QPXMOLDCXLPFIU-UHFFFAOYSA-N 0.000 description 1
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