AU2004282101A1 - Compounds and methods for treating dyslipidemia - Google Patents

Info

Publication number

AU2004282101A1

AU2004282101A1 AU2004282101A AU2004282101A AU2004282101A1 AU 2004282101 A1 AU2004282101 A1 AU 2004282101A1 AU 2004282101 A AU2004282101 A AU 2004282101A AU 2004282101 A AU2004282101 A AU 2004282101A AU 2004282101 A1 AU2004282101 A1 AU 2004282101A1

Authority

AU

Australia

Prior art keywords

trifluoromethyl

amino

azepine

mmol

acetyl

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 311
• 238000000034 method Methods 0.000 title claims abstract description 151
• 208000032928 Dyslipidaemia Diseases 0.000 title claims description 11
• 208000017170 Lipid metabolism disease Diseases 0.000 title claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 239000000203 mixture Substances 0.000 claims description 221
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 158
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 95
• 229910052757 nitrogen Inorganic materials 0.000 claims description 90
• 125000000623 heterocyclic group Chemical group 0.000 claims description 59
• 150000003839 salts Chemical class 0.000 claims description 44
• 125000003118 aryl group Chemical group 0.000 claims description 38
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
• 230000000694 effects Effects 0.000 claims description 29
• 239000012453 solvate Substances 0.000 claims description 28
• HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical group C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 24
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 20
• 125000004104 aryloxy group Chemical group 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 18
• 201000001320 Atherosclerosis Diseases 0.000 claims description 16
• 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
• 125000005843 halogen group Chemical group 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
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 9
• 238000008214 LDL Cholesterol Methods 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 230000001575 pathological effect Effects 0.000 claims description 8
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 239000003814 drug Substances 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 Chemical group 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 239000011593 sulfur Chemical group 0.000 claims description 6
• 108010028554 LDL Cholesterol Proteins 0.000 claims description 5
• 208000008589 Obesity Diseases 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 235000020824 obesity Nutrition 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 3
• 230000003828 downregulation Effects 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 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 3
• 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims description 2
• 108010023302 HDL Cholesterol Proteins 0.000 claims description 2
• 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 2
• 230000007423 decrease Effects 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
• CRZNWWQCQMNPDQ-UHFFFAOYSA-N ethyl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-bromo-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(Br)=CC=C2N(C(=O)OCC)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CRZNWWQCQMNPDQ-UHFFFAOYSA-N 0.000 claims description 2
• QZHRDXDOMBMPSR-UHFFFAOYSA-N ethyl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-methoxy-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(OC)=CC=C2N(C(=O)OCC)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QZHRDXDOMBMPSR-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
• RVRORVXTCVMLEC-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)C)C2=CC=CC=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RVRORVXTCVMLEC-UHFFFAOYSA-N 0.000 claims description 2
• BXRMMCDXDYARCY-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-8-chloro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)C)C2=CC(Cl)=CC=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BXRMMCDXDYARCY-UHFFFAOYSA-N 0.000 claims description 2
• ZSUWCVWQMAHOLR-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2-methyl-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)C(C)CCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZSUWCVWQMAHOLR-UHFFFAOYSA-N 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
• 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 2
• 102100037637 Cholesteryl ester transfer protein Human genes 0.000 claims 2
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
• 206010003210 Arteriosclerosis Diseases 0.000 claims 1
• 230000003042 antagnostic effect Effects 0.000 claims 1
• 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
• 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 1
• 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 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
• 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 1
• 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 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 595
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 287
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 279
• 235000019439 ethyl acetate Nutrition 0.000 description 195
• 229940093499 ethyl acetate Drugs 0.000 description 194
• 239000000243 solution Substances 0.000 description 151
• 239000002904 solvent Substances 0.000 description 145
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 122
• 238000002360 preparation method Methods 0.000 description 118
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 117
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 106
• 238000003756 stirring Methods 0.000 description 103
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 98
• 230000002829 reductive effect Effects 0.000 description 92
• 239000007787 solid Substances 0.000 description 92
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 84
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 80
• 239000012044 organic layer Substances 0.000 description 78
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 74
• 239000012267 brine Substances 0.000 description 73
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 73
• 238000006243 chemical reaction Methods 0.000 description 71
• 230000015572 biosynthetic process Effects 0.000 description 66
• 238000003786 synthesis reaction Methods 0.000 description 65
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 58
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• 239000000741 silica gel Substances 0.000 description 56
• 229910002027 silica gel Inorganic materials 0.000 description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 52
• 239000000284 extract Substances 0.000 description 52
• 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 description 51
• 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 description 51
• 239000003153 chemical reaction reagent Substances 0.000 description 50
• 229910052938 sodium sulfate Inorganic materials 0.000 description 49
• 235000011152 sodium sulphate Nutrition 0.000 description 49
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
• 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 41
• 239000000725 suspension Substances 0.000 description 40
• 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 37
• 238000004587 chromatography analysis Methods 0.000 description 35
• 108010010234 HDL Lipoproteins Proteins 0.000 description 33
• 102000015779 HDL Lipoproteins Human genes 0.000 description 33
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 33
• 239000012298 atmosphere Substances 0.000 description 30
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 30
• 239000003921 oil Substances 0.000 description 29
• 235000019198 oils Nutrition 0.000 description 29
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 28
• 239000010410 layer Substances 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 26
• 238000005481 NMR spectroscopy Methods 0.000 description 25
• 235000011167 hydrochloric acid Nutrition 0.000 description 24
• 125000003342 alkenyl group Chemical group 0.000 description 23
• 238000003818 flash chromatography Methods 0.000 description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
• 239000000706 filtrate Substances 0.000 description 22
• 238000000746 purification Methods 0.000 description 21
• 239000011734 sodium Substances 0.000 description 21
• 238000003556 assay Methods 0.000 description 20
• 239000000651 prodrug Substances 0.000 description 19
• 229940002612 prodrug Drugs 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• 239000002253 acid Substances 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• 238000009472 formulation Methods 0.000 description 17
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 16
• 208000029078 coronary artery disease Diseases 0.000 description 16
• 238000010898 silica gel chromatography Methods 0.000 description 16
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• DHVHORCFFOSRBP-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DHVHORCFFOSRBP-UHFFFAOYSA-N 0.000 description 15
• 229960000583 acetic acid Drugs 0.000 description 15
• 150000001412 amines Chemical class 0.000 description 15
• 235000012000 cholesterol Nutrition 0.000 description 15
• 239000012043 crude product Substances 0.000 description 15
• 239000000543 intermediate Substances 0.000 description 15
• JHTAZINCWANFHY-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-bromo-8-chloro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(Br)=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 JHTAZINCWANFHY-UHFFFAOYSA-N 0.000 description 15
• 239000003480 eluent Substances 0.000 description 14
• 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
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 14
• IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 14
• 238000010926 purge Methods 0.000 description 14
• 239000012279 sodium borohydride Substances 0.000 description 14
• 229910000033 sodium borohydride Inorganic materials 0.000 description 14
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 13
• 125000001188 haloalkyl group Chemical group 0.000 description 13
• 239000005457 ice water Substances 0.000 description 13
• 150000002632 lipids Chemical class 0.000 description 13
• YPSSCICDVDOEAI-UHFFFAOYSA-N methyl-2-amino-4-chlorobenzoate Natural products COC(=O)C1=CC=C(Cl)C=C1N YPSSCICDVDOEAI-UHFFFAOYSA-N 0.000 description 13
• BFTNJCIVUBVMPP-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-bromo-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(Br)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BFTNJCIVUBVMPP-UHFFFAOYSA-N 0.000 description 13
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• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 2
• 230000001631 hypertensive effect Effects 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 125000001041 indolyl group Chemical group 0.000 description 2
• 230000002401 inhibitory effect Effects 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
• 239000012948 isocyanate Substances 0.000 description 2
• 150000002513 isocyanates Chemical class 0.000 description 2
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
• 230000000670 limiting effect Effects 0.000 description 2
• 108010053156 lipid transfer protein Proteins 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
• 235000019341 magnesium sulphate Nutrition 0.000 description 2
• 238000003760 magnetic stirring Methods 0.000 description 2
• 238000001819 mass spectrum Methods 0.000 description 2
• 230000001404 mediated effect Effects 0.000 description 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• PYJKHLVSWUVFGT-UHFFFAOYSA-N methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=CC(C(F)(F)F)=C1NC(=O)OC(C)(C)C PYJKHLVSWUVFGT-UHFFFAOYSA-N 0.000 description 2
• 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
• 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
• 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
• VKJYAPKCOSGXAD-UHFFFAOYSA-N methyl 2-amino-6-fluorobenzoate Chemical compound COC(=O)C1=C(N)C=CC=C1F VKJYAPKCOSGXAD-UHFFFAOYSA-N 0.000 description 2
• HCLLOQLXKCCWLJ-UHFFFAOYSA-N methyl 2-amino-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1N HCLLOQLXKCCWLJ-UHFFFAOYSA-N 0.000 description 2
• 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
• FCFDTXFPVQIHKX-UHFFFAOYSA-N methyl 2-fluoro-6-[(4-methoxy-4-oxobutyl)-propan-2-yloxycarbonylamino]-3-methylbenzoate Chemical compound COC(=O)CCCN(C(=O)OC(C)C)C1=CC=C(C)C(F)=C1C(=O)OC FCFDTXFPVQIHKX-UHFFFAOYSA-N 0.000 description 2
• JQONJINUHIREOI-UHFFFAOYSA-N methyl 2-methyl-6-(propan-2-yloxycarbonylamino)benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1NC(=O)OC(C)C JQONJINUHIREOI-UHFFFAOYSA-N 0.000 description 2
• 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
• LGJFZFQJSRMCMW-UHFFFAOYSA-N methyl 4-[(4-ethoxy-4-oxobutyl)-propan-2-yloxycarbonylamino]-2,3-dihydro-1h-indene-5-carboxylate Chemical compound C1=C(C(=O)OC)C(N(C(=O)OC(C)C)CCCC(=O)OCC)=C2CCCC2=C1 LGJFZFQJSRMCMW-UHFFFAOYSA-N 0.000 description 2
• YOULVVVUZMFFRU-UHFFFAOYSA-N methyl 4-amino-7-bromo-2,3-dihydro-1h-indene-5-carboxylate Chemical compound COC(=O)C1=CC(Br)=C2CCCC2=C1N YOULVVVUZMFFRU-UHFFFAOYSA-N 0.000 description 2
• YCGJNRITCDQDJW-UHFFFAOYSA-N methyl 4-bromo-2-(propan-2-yloxycarbonylamino)benzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1NC(=O)OC(C)C YCGJNRITCDQDJW-UHFFFAOYSA-N 0.000 description 2
• DOJNVKCYNMYYLR-UHFFFAOYSA-N methyl 4-bromo-2-[(4-ethoxy-4-oxobutyl)-propan-2-yloxycarbonylamino]-3-methylbenzoate Chemical compound CCOC(=O)CCCN(C(=O)OC(C)C)C1=C(C)C(Br)=CC=C1C(=O)OC DOJNVKCYNMYYLR-UHFFFAOYSA-N 0.000 description 2
• MAZBZVJZEXQUGP-UHFFFAOYSA-N methyl 4-bromo-2-[(4-methoxy-4-oxobutyl)-propan-2-yloxycarbonylamino]benzoate Chemical compound COC(=O)CCCN(C(=O)OC(C)C)C1=CC(Br)=CC=C1C(=O)OC MAZBZVJZEXQUGP-UHFFFAOYSA-N 0.000 description 2
• YTWDMAAPIWOIFZ-UHFFFAOYSA-N methyl 4-bromo-2-nitrobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1[N+]([O-])=O YTWDMAAPIWOIFZ-UHFFFAOYSA-N 0.000 description 2
• ALTNJBMTNKTQPH-UHFFFAOYSA-N methyl 4-bromo-3-methyl-2-(propan-2-yloxycarbonylamino)benzoate Chemical compound COC(=O)C1=CC=C(Br)C(C)=C1NC(=O)OC(C)C ALTNJBMTNKTQPH-UHFFFAOYSA-N 0.000 description 2
• DETWLLNYSWQPSD-UHFFFAOYSA-N methyl 4-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1NC(=O)OC(C)(C)C DETWLLNYSWQPSD-UHFFFAOYSA-N 0.000 description 2
• HZJJUCYZMHSDMU-UHFFFAOYSA-N methyl 4-chloro-2-[(4-methoxy-4-oxobutyl)-[(2-methylpropan-2-yl)oxycarbonyl]amino]benzoate Chemical compound COC(=O)CCCN(C(=O)OC(C)(C)C)C1=CC(Cl)=CC=C1C(=O)OC HZJJUCYZMHSDMU-UHFFFAOYSA-N 0.000 description 2
• PQIUCRLKGPRYBE-UHFFFAOYSA-N methyl 5-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(trifluoromethoxy)benzoate Chemical compound COC(=O)C1=CC(C)=C(OC(F)(F)F)C=C1NC(=O)OC(C)(C)C PQIUCRLKGPRYBE-UHFFFAOYSA-N 0.000 description 2
• NPOOCZGCWRRWPO-UHFFFAOYSA-N n-(1-acetyl-8-chloro-2,3,4,5-tetrahydro-1-benzazepin-5-yl)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C1CCN(C(C)=O)C2=CC(Cl)=CC=C2C1N(C(=O)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NPOOCZGCWRRWPO-UHFFFAOYSA-N 0.000 description 2
• QUMHHDIXNRMGPW-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-4-yl)-2-hydroxyiminoacetamide Chemical compound ON=CC(=O)NC1=CC=CC2=C1CCC2 QUMHHDIXNRMGPW-UHFFFAOYSA-N 0.000 description 2
• JGYVIPWUIQREKH-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-5-yl)-2-hydroxyiminoacetamide Chemical compound ON=CC(=O)NC1=CC=C2CCCC2=C1 JGYVIPWUIQREKH-UHFFFAOYSA-N 0.000 description 2
• LRRMXJLMFOFDOR-UHFFFAOYSA-N n-(3-fluoro-4-methylphenyl)-2-hydroxyiminoacetamide Chemical compound CC1=CC=C(NC(=O)C=NO)C=C1F LRRMXJLMFOFDOR-UHFFFAOYSA-N 0.000 description 2
• IDKUPQARCGUVRQ-UHFFFAOYSA-N n-[2-bromo-4-(trifluoromethyl)phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C(F)(F)F)C=C1Br IDKUPQARCGUVRQ-UHFFFAOYSA-N 0.000 description 2
• OSOIPBSUGCAQPZ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[7-(trifluoromethyl)-2,3,4,5-tetrahydro-1h-1-benzazepin-5-yl]acetamide Chemical compound C1CCNC2=CC=C(C(F)(F)F)C=C2C1N(C(=O)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OSOIPBSUGCAQPZ-UHFFFAOYSA-N 0.000 description 2
• QWVHZUVBNCIZFP-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1h-1-benzazepin-5-yl]acetamide Chemical compound C1CCNC2=CC(C(F)(F)F)=C(C)C=C2C1N(C(=O)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QWVHZUVBNCIZFP-UHFFFAOYSA-N 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
• 239000010502 orange oil Substances 0.000 description 2
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• 150000002923 oximes Chemical class 0.000 description 2
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• 230000036470 plasma concentration Effects 0.000 description 2
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• 239000011698 potassium fluoride Substances 0.000 description 2
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• DRXIHXUEWVVBMY-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-3,4,5,8,9,10-hexahydro-2h-cyclopenta[i][1]benzazepine-1-carboxylate Chemical compound C12=CC=C3CCCC3=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DRXIHXUEWVVBMY-UHFFFAOYSA-N 0.000 description 2
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• REJHQPOTUVZHPQ-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-bromo-8-fluoro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(Br)=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 REJHQPOTUVZHPQ-UHFFFAOYSA-N 0.000 description 2
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• KIZQWGRVSWYHCE-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-methyl-3,4,5,8,9,10-hexahydro-2h-cyclopenta[i][1]benzazepine-1-carboxylate Chemical compound C12=CC(C)=C3CCCC3=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 KIZQWGRVSWYHCE-UHFFFAOYSA-N 0.000 description 2
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• WAXBZSZLZWGBLG-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-(dimethylamino)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(N(C)C)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WAXBZSZLZWGBLG-UHFFFAOYSA-N 0.000 description 2
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• NSPYLQDVOKNZCJ-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-chloro-7-(dimethylamino)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(N(C)C)=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 NSPYLQDVOKNZCJ-UHFFFAOYSA-N 0.000 description 2
• PVOCAERXCLWILN-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-fluoro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=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 PVOCAERXCLWILN-UHFFFAOYSA-N 0.000 description 2
• KCIUQCFQRFWYRA-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-morpholin-4-yl-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(N3CCOCC3)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 KCIUQCFQRFWYRA-UHFFFAOYSA-N 0.000 description 2
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• OVBRKMOHSLYVCY-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-9-bromo-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=CC(Br)=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OVBRKMOHSLYVCY-UHFFFAOYSA-N 0.000 description 2
• HNRBRSFOGWTCJS-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-9-methyl-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC(C)=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HNRBRSFOGWTCJS-UHFFFAOYSA-N 0.000 description 2
• UDYLCNVDYONNQB-UHFFFAOYSA-N propan-2-yl 5-oxo-2,3,4,7,8,9-hexahydrocyclopenta[h][1]benzazepine-1-carboxylate Chemical compound C1=C2N(C(=O)OC(C)C)CCCC(=O)C2=CC2=C1CCC2 UDYLCNVDYONNQB-UHFFFAOYSA-N 0.000 description 2
• ZIAPNHIGEHLYPJ-UHFFFAOYSA-N propan-2-yl 5-oxo-2,3,4,8,9,10-hexahydrocyclopenta[i][1]benzazepine-1-carboxylate Chemical compound CC(C)OC(=O)N1CCCC(=O)C2=CC=C(CCC3)C3=C12 ZIAPNHIGEHLYPJ-UHFFFAOYSA-N 0.000 description 2
• FMLGGXFJRAWONV-UHFFFAOYSA-N propan-2-yl 5-oxo-3,4-dihydro-2h-1-benzazepine-1-carboxylate Chemical compound CC(C)OC(=O)N1CCCC(=O)C2=CC=CC=C12 FMLGGXFJRAWONV-UHFFFAOYSA-N 0.000 description 2
• OSISYENSMFLOPM-UHFFFAOYSA-N propan-2-yl 6-fluoro-5-oxo-3,4-dihydro-2h-1-benzazepine-1-carboxylate Chemical compound CC(C)OC(=O)N1CCCC(=O)C2=C(F)C=CC=C12 OSISYENSMFLOPM-UHFFFAOYSA-N 0.000 description 2
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