NO317293B1 - Tetrahydrobenzindolderivat, farmasoytisk preparat samt mellomproduktforbindelse - Google Patents

Info

Publication number

NO317293B1

NO317293B1 NO20003285A NO20003285A NO317293B1 NO 317293 B1 NO317293 B1 NO 317293B1 NO 20003285 A NO20003285 A NO 20003285A NO 20003285 A NO20003285 A NO 20003285A NO 317293 B1 NO317293 B1 NO 317293B1

Authority

NO

Norway

Prior art keywords

mmol

tetrahydro

compound

synthesis example

group

Prior art date

1997-12-25

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 413
• 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
• GHDKZRYOSSRTLA-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-benzo[g]indole Chemical class C1C=C2C=CC=CC2=C2C1CCN2 GHDKZRYOSSRTLA-UHFFFAOYSA-N 0.000 title description 7
• 239000012450 pharmaceutical intermediate Substances 0.000 title 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 38
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 4
• 150000003839 salts Chemical class 0.000 claims description 39
• -1 t-butoxycarbonyl Chemical group 0.000 claims description 34
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 24
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• 208000020016 psychiatric disease Diseases 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 229910052727 yttrium Inorganic materials 0.000 claims description 4
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims description 3
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 229910052796 boron Inorganic materials 0.000 claims description 2
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 abstract description 15
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 14
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 abstract description 5
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 abstract description 5
• 230000005856 abnormality Effects 0.000 abstract description 5
• 229940076279 serotonin Drugs 0.000 abstract description 5
• 229910052717 sulfur Inorganic materials 0.000 abstract description 4
• 230000002093 peripheral effect Effects 0.000 abstract description 3
• 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
• 229910052799 carbon Inorganic materials 0.000 abstract 1
• 230000006806 disease prevention Effects 0.000 abstract 1
• 229910052760 oxygen Inorganic materials 0.000 abstract 1
• 229910052739 hydrogen Inorganic materials 0.000 description 752
• 238000003786 synthesis reaction Methods 0.000 description 284
• 230000015572 biosynthetic process Effects 0.000 description 283
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 261
• 239000000243 solution Substances 0.000 description 222
• 238000001819 mass spectrum Methods 0.000 description 173
• 238000006243 chemical reaction Methods 0.000 description 146
• 239000002904 solvent Substances 0.000 description 132
• 230000002829 reductive effect Effects 0.000 description 131
• 238000005160 1H NMR spectroscopy Methods 0.000 description 125
• 238000001704 evaporation Methods 0.000 description 121
• 230000008020 evaporation Effects 0.000 description 110
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 107
• 238000002451 electron ionisation mass spectrometry Methods 0.000 description 103
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 101
• 238000000034 method Methods 0.000 description 100
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 91
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
• 238000010898 silica gel chromatography Methods 0.000 description 62
• 239000000463 material Substances 0.000 description 61
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 52
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 42
• 101150041968 CDC13 gene Proteins 0.000 description 41
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• 238000005481 NMR spectroscopy Methods 0.000 description 38
• WTHVGNDEIMLIHE-UHFFFAOYSA-N n-methyl-2-[2-[4-(2-oxo-1,3,4,5-tetrahydrobenzo[cd]indol-2a-yl)butyl]-3,4-dihydro-1h-pyrido[3,4-b]indol-9-yl]acetamide Chemical compound C12=CC=CC=C2N(CC(=O)NC)C2=C1CCN(CCCCC13C(NC=4C=CC=C(C3=4)CCC1)=O)C2 WTHVGNDEIMLIHE-UHFFFAOYSA-N 0.000 description 32
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
• 239000012044 organic layer Substances 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 239000007795 chemical reaction product Substances 0.000 description 30
• 239000000203 mixture Substances 0.000 description 26
• 229910000027 potassium carbonate Inorganic materials 0.000 description 26
• 235000011181 potassium carbonates Nutrition 0.000 description 26
• 239000011734 sodium Substances 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• 239000011541 reaction mixture Substances 0.000 description 23
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 22
• 239000012312 sodium hydride Substances 0.000 description 22
• 229910000104 sodium hydride Inorganic materials 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 238000010828 elution Methods 0.000 description 21
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
• 239000000460 chlorine Substances 0.000 description 20
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
• 238000001914 filtration Methods 0.000 description 18
• 239000002585 base Substances 0.000 description 17
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 16
• XVCXKZISCOBPDZ-UHFFFAOYSA-N 2a-(4-bromobutyl)-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC3=C2C1(CCCCBr)C(=O)N3 XVCXKZISCOBPDZ-UHFFFAOYSA-N 0.000 description 14
• 239000002253 acid Substances 0.000 description 14
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
• 239000013078 crystal Substances 0.000 description 14
• 238000001035 drying Methods 0.000 description 14
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 14
• 239000013067 intermediate product Substances 0.000 description 14
• GFJCZDJPSXKGSF-UHFFFAOYSA-N tert-butyl 1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1CN(C(=O)OC(C)(C)C)CC2 GFJCZDJPSXKGSF-UHFFFAOYSA-N 0.000 description 14
• OGUWOLDNYOTRBO-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1NCCC2=C1C=CS2 OGUWOLDNYOTRBO-UHFFFAOYSA-N 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 12
• 108091005436 5-HT7 receptors Proteins 0.000 description 11
• WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 11
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 11
• 238000004519 manufacturing process Methods 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• HUCMZMNAPUWYOC-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)piperazine;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2C1N1CCNCC1 HUCMZMNAPUWYOC-UHFFFAOYSA-N 0.000 description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
• 239000001257 hydrogen Substances 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
• CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical class N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 description 8
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
• YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical compound C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
• GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
• 125000003118 aryl group Chemical group 0.000 description 7
• 239000012298 atmosphere Substances 0.000 description 7
• 230000027455 binding Effects 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 238000010790 dilution Methods 0.000 description 7
• 239000012895 dilution Substances 0.000 description 7
• 239000002244 precipitate Substances 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 238000006722 reduction reaction Methods 0.000 description 7
• GOUUEYJGXNNEIV-UHFFFAOYSA-N tert-butyl 4-(6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1C2=CC=CC=C2CCCC1 GOUUEYJGXNNEIV-UHFFFAOYSA-N 0.000 description 7
• UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 6
• 239000012442 inert solvent Substances 0.000 description 6
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
• 239000012266 salt solution Substances 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• DOBGHCDMPAGIGS-UHFFFAOYSA-N tert-butyl 4-(2,3-dihydro-1h-inden-1-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1C2=CC=CC=C2CC1 DOBGHCDMPAGIGS-UHFFFAOYSA-N 0.000 description 6
• ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• PTLTZFJYSSVFEC-UHFFFAOYSA-N 2-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1NCCC2=C1C=C(C)S2 PTLTZFJYSSVFEC-UHFFFAOYSA-N 0.000 description 5
• VYACEHZLOWZZEV-UHFFFAOYSA-N 5-[(2-methylpropan-2-yl)oxycarbonyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine-2-carboxylic acid Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C=C(C(O)=O)S2 VYACEHZLOWZZEV-UHFFFAOYSA-N 0.000 description 5
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
• 239000007868 Raney catalyst Substances 0.000 description 5
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
• 229910000564 Raney nickel Inorganic materials 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 238000010438 heat treatment Methods 0.000 description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
• 229910003446 platinum oxide Inorganic materials 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 5
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
• XCZJAIPXDKUJPJ-UHFFFAOYSA-N 2-o-tert-butyl 9-o-methyl 3,4-dihydro-1h-pyrido[3,4-b]indole-2,9-dicarboxylate Chemical compound C12=CC=CC=C2N(C(=O)OC)C2=C1CCN(C(=O)OC(C)(C)C)C2 XCZJAIPXDKUJPJ-UHFFFAOYSA-N 0.000 description 4
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
• ZUZMVTSAPQEJGT-UHFFFAOYSA-N 3-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1CNCC2=C1SC=C2C ZUZMVTSAPQEJGT-UHFFFAOYSA-N 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
• 238000004458 analytical method Methods 0.000 description 4
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
• 239000003814 drug Substances 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 150000002148 esters Chemical group 0.000 description 4
• 238000005658 halogenation reaction Methods 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
• AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 4
• 238000007363 ring formation reaction Methods 0.000 description 4
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
• SQEZXFSADTVEQB-UHFFFAOYSA-N 1-methylbenzo[cd]indol-2-one Chemical compound C1=CC(N(C)C2=O)=C3C2=CC=CC3=C1 SQEZXFSADTVEQB-UHFFFAOYSA-N 0.000 description 3
• FGGBJUOJAKQFRD-UHFFFAOYSA-N 1-oxido-5,6,7,8-tetrahydroquinolin-1-ium Chemical compound C1CCCC2=C1C=CC=[N+]2[O-] FGGBJUOJAKQFRD-UHFFFAOYSA-N 0.000 description 3
• MIBUNYFPYOXIFZ-UHFFFAOYSA-N 2,3-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1CNCC2=C1SC(C)=C2C MIBUNYFPYOXIFZ-UHFFFAOYSA-N 0.000 description 3
• CRJMOQUKRGIGLY-UHFFFAOYSA-N 2a,3,4,5-tetrahydro-1h-benzo[cd]indol-2-one Chemical compound C1CCC2C(=O)NC3=CC=CC1=C32 CRJMOQUKRGIGLY-UHFFFAOYSA-N 0.000 description 3
• QHZLYKACDALOBB-UHFFFAOYSA-N 2a-(3-bromopropyl)-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC3=C2C1(CCCBr)C(=O)N3 QHZLYKACDALOBB-UHFFFAOYSA-N 0.000 description 3
• MGSHXMOLUWTMGP-UHFFFAOYSA-N 3'-carboxy-alpha-chromanol Chemical compound C1=CC=C2C(O)CCOC2=C1 MGSHXMOLUWTMGP-UHFFFAOYSA-N 0.000 description 3
• CNXFGNVBRLEVBD-UHFFFAOYSA-N 4,5,6,7-tetrahydrofuro[3,2-c]pyridine Chemical compound C1NCCC2=C1C=CO2 CNXFGNVBRLEVBD-UHFFFAOYSA-N 0.000 description 3
• BSDGZUDFPKIYQG-UHFFFAOYSA-N 4-bromopyridine Chemical compound BrC1=CC=NC=C1 BSDGZUDFPKIYQG-UHFFFAOYSA-N 0.000 description 3
• YCQHYOBSOVFBEB-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinolin-8-ol Chemical compound C1=CN=C2C(O)CCCC2=C1 YCQHYOBSOVFBEB-UHFFFAOYSA-N 0.000 description 3
• QTEIQTRPDDPVKV-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinolin-8-yl acetate Chemical compound C1=CN=C2C(OC(=O)C)CCCC2=C1 QTEIQTRPDDPVKV-UHFFFAOYSA-N 0.000 description 3
• HZPXWGZCCZHHFH-UHFFFAOYSA-N 9-bromo-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound BrC1CCCC(=O)C2=CC=CC=C12 HZPXWGZCCZHHFH-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
• YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 3
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
• 239000005909 Kieselgur Substances 0.000 description 3
• 238000010521 absorption reaction Methods 0.000 description 3
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
• 239000012346 acetyl chloride Substances 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 230000010933 acylation Effects 0.000 description 3
• 238000005917 acylation reaction Methods 0.000 description 3
• 230000029936 alkylation Effects 0.000 description 3
• 238000005804 alkylation reaction Methods 0.000 description 3
• 235000011114 ammonium hydroxide Nutrition 0.000 description 3
• 239000012300 argon atmosphere Substances 0.000 description 3
• 239000000872 buffer Substances 0.000 description 3
• 238000010531 catalytic reduction reaction Methods 0.000 description 3
• 238000010511 deprotection reaction Methods 0.000 description 3
• 239000002552 dosage form Substances 0.000 description 3
• 230000026030 halogenation Effects 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
• 239000012046 mixed solvent Substances 0.000 description 3
• OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 235000019198 oils Nutrition 0.000 description 3
• 230000003647 oxidation Effects 0.000 description 3
• 238000007254 oxidation reaction Methods 0.000 description 3
• 239000002798 polar solvent Substances 0.000 description 3
• 235000015497 potassium bicarbonate Nutrition 0.000 description 3
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
• 239000011736 potassium bicarbonate Substances 0.000 description 3
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• 150000003335 secondary amines Chemical class 0.000 description 3
• 239000012279 sodium borohydride Substances 0.000 description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
• 238000006467 substitution reaction Methods 0.000 description 3
• 125000004434 sulfur atom Chemical group 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 238000001308 synthesis method Methods 0.000 description 3
• DUXYNAUJNWHWLS-UHFFFAOYSA-N tert-butyl 2,4,4a,5-tetrahydro-1h-pyrazino[2,1-c][1,4]benzothiazine-3-carboxylate Chemical compound C1=CC=C2N3CCN(C(=O)OC(C)(C)C)CC3CSC2=C1 DUXYNAUJNWHWLS-UHFFFAOYSA-N 0.000 description 3
• WNASTMXQUJOXDJ-UHFFFAOYSA-N tert-butyl 2-carbamoyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C=C(C(N)=O)S2 WNASTMXQUJOXDJ-UHFFFAOYSA-N 0.000 description 3
• QDJSWSBQYDDJGI-UHFFFAOYSA-N tert-butyl 3-methyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CC2=C1SC=C2C QDJSWSBQYDDJGI-UHFFFAOYSA-N 0.000 description 3
• DGYXRUYCQAYVDM-UHFFFAOYSA-N tert-butyl 6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C=CS2 DGYXRUYCQAYVDM-UHFFFAOYSA-N 0.000 description 3
• OJCPAWSZNLDKDV-UHFFFAOYSA-N tert-butyl 9-(2-methoxy-2-oxoethyl)-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(CC(=O)OC)C2=C1CCN(C(=O)OC(C)(C)C)C2 OJCPAWSZNLDKDV-UHFFFAOYSA-N 0.000 description 3
• XKXIQBVKMABYQJ-UHFFFAOYSA-N tert-butyl hydrogen carbonate Chemical compound CC(C)(C)OC(O)=O XKXIQBVKMABYQJ-UHFFFAOYSA-N 0.000 description 3
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
• APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 3
• 229910052721 tungsten Inorganic materials 0.000 description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
• LDUZILRBWUAJLE-UHFFFAOYSA-N 1,2,3,4-tetrahydro-[1]benzofuro[2,3-c]pyridine Chemical compound O1C2=CC=CC=C2C2=C1CNCC2 LDUZILRBWUAJLE-UHFFFAOYSA-N 0.000 description 2
• LOSHLRVJQKCQNH-UHFFFAOYSA-N 1,2,3,4-tetrahydro-[1]benzothiolo[2,3-c]pyridine Chemical compound S1C2=CC=CC=C2C2=C1CNCC2 LOSHLRVJQKCQNH-UHFFFAOYSA-N 0.000 description 2
• XDHYTSMMYGWXFI-UHFFFAOYSA-N 1,2,3,4-tetrahydro-[1]benzothiolo[2,3-c]pyridine;hydrochloride Chemical compound Cl.S1C2=CC=CC=C2C2=C1CNCC2 XDHYTSMMYGWXFI-UHFFFAOYSA-N 0.000 description 2
• FHTDAVICELDDEP-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrido[3,4-b]indole-9-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(C(=O)N)C2=C1CCNC2 FHTDAVICELDDEP-UHFFFAOYSA-N 0.000 description 2
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
• KBNFLEIETBDDCM-UHFFFAOYSA-N 1-(1,2,3,4,4a,5-hexahydropyrazino[1,2-a]quinoxalin-6-yl)-2,2,2-trifluoroethanone;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C(=O)C(F)(F)F)CC2N1CCNC2 KBNFLEIETBDDCM-UHFFFAOYSA-N 0.000 description 2
• PCWDIVRWNCOMOW-UHFFFAOYSA-N 1-(1,2,3,4-tetrahydronaphthalen-1-yl)piperidine;hydrochloride Chemical compound Cl.C1CCCCN1C1C2=CC=CC=C2CCC1 PCWDIVRWNCOMOW-UHFFFAOYSA-N 0.000 description 2
• VZSWVECFWCGGRD-UHFFFAOYSA-N 1-(1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)propan-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(CC(=O)C)C2=C1CCNC2 VZSWVECFWCGGRD-UHFFFAOYSA-N 0.000 description 2
• MMUMHCHGKODAIZ-UHFFFAOYSA-N 1-(2-phenylpropan-2-yl)piperazine Chemical compound C=1C=CC=CC=1C(C)(C)N1CCNCC1 MMUMHCHGKODAIZ-UHFFFAOYSA-N 0.000 description 2
• PTKBLKMIBNIWKW-UHFFFAOYSA-N 1-(3,4-dihydro-2h-chromen-4-yl)piperazine;hydrochloride Chemical compound Cl.C1CNCCN1C1C2=CC=CC=C2OCC1 PTKBLKMIBNIWKW-UHFFFAOYSA-N 0.000 description 2
• YEZOMSWXFZSYFB-UHFFFAOYSA-N 1-(3,4-dihydro-2h-thiochromen-4-yl)piperazine;hydrochloride Chemical compound Cl.C1CNCCN1C1C2=CC=CC=C2SCC1 YEZOMSWXFZSYFB-UHFFFAOYSA-N 0.000 description 2
• AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
• IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 2
• BYZKRKXJSNSHEE-UHFFFAOYSA-N 1-ethyl-2-benzo[cd]indolone Chemical compound C1=CC(N(CC)C2=O)=C3C2=CC=CC3=C1 BYZKRKXJSNSHEE-UHFFFAOYSA-N 0.000 description 2
• KXPKPBDFRGOZMB-UHFFFAOYSA-N 1-ethyl-2a,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC3=C2C1C(=O)N3CC KXPKPBDFRGOZMB-UHFFFAOYSA-N 0.000 description 2
• OHMYJENBKYRFGD-UHFFFAOYSA-N 1-pyridin-4-yl-2,3-dihydroinden-1-ol Chemical compound C1CC2=CC=CC=C2C1(O)C1=CC=NC=C1 OHMYJENBKYRFGD-UHFFFAOYSA-N 0.000 description 2
• ZCYWNEIJWZMTDS-UHFFFAOYSA-N 1-pyridin-4-yl-3,4-dihydro-2h-naphthalen-1-ol Chemical compound C1CCC2=CC=CC=C2C1(O)C1=CC=NC=C1 ZCYWNEIJWZMTDS-UHFFFAOYSA-N 0.000 description 2
• GPYLCFQEKPUWLD-UHFFFAOYSA-N 1h-benzo[cd]indol-2-one Chemical compound C1=CC(C(=O)N2)=C3C2=CC=CC3=C1 GPYLCFQEKPUWLD-UHFFFAOYSA-N 0.000 description 2
• PVOSECZBLPUJLZ-UHFFFAOYSA-N 2,3,4,4a,5,6-hexahydro-1h-pyrazino[1,2-a]quinoxaline Chemical class C1=CC=C2N3CCNCC3CNC2=C1 PVOSECZBLPUJLZ-UHFFFAOYSA-N 0.000 description 2
• WWQPGNZHJFFKRW-UHFFFAOYSA-N 2,3,4,5-tetrahydro-2-benzazepin-1-one Chemical compound O=C1NCCCC2=CC=CC=C12 WWQPGNZHJFFKRW-UHFFFAOYSA-N 0.000 description 2
• CBKHEZWKYMWCKX-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)acetonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(CC#N)C2=C1CCNC2 CBKHEZWKYMWCKX-UHFFFAOYSA-N 0.000 description 2
• UAFBGDLXUIBTFM-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-3,4-dihydro-1h-isoquinoline Chemical compound C1CC(N2CC3=CC=CC=C3CC2)CCN1CC1=CC=CC=C1 UAFBGDLXUIBTFM-UHFFFAOYSA-N 0.000 description 2
• UPVSBCHZSIHTBX-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-2-methylpropanenitrile Chemical compound C1CN(C(C)(C#N)C)CCN1CC1=CC=CC=C1 UPVSBCHZSIHTBX-UHFFFAOYSA-N 0.000 description 2
• NMIOWXDCRJVKAY-UHFFFAOYSA-N 2-[2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1h-pyrido[3,4-b]indol-9-yl]acetic acid Chemical compound OC(=O)CN1C2=CC=CC=C2C2=C1CN(C(=O)OC(C)(C)C)CC2 NMIOWXDCRJVKAY-UHFFFAOYSA-N 0.000 description 2
• MYWFDOPJSJFFBX-UHFFFAOYSA-N 2-[benzyl(furan-3-ylmethyl)amino]ethanol Chemical compound C=1C=CC=CC=1CN(CCO)CC=1C=COC=1 MYWFDOPJSJFFBX-UHFFFAOYSA-N 0.000 description 2
• JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 2
• REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 2
• NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 2
• DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
• AQEYJNQCMXIBFF-UHFFFAOYSA-N 2-oxido-5,6,7,8-tetrahydroisoquinolin-2-ium Chemical compound C1CCCC2=C[N+]([O-])=CC=C21 AQEYJNQCMXIBFF-UHFFFAOYSA-N 0.000 description 2
• VIDWEXGVLRTXHK-UHFFFAOYSA-N 2-piperidin-4-yl-3,4-dihydro-1h-isoquinoline;dihydrobromide Chemical compound Br.Br.C1CNCCC1N1CC2=CC=CC=C2CC1 VIDWEXGVLRTXHK-UHFFFAOYSA-N 0.000 description 2
• OJYTXMKMQSNBNA-UHFFFAOYSA-N 2a-(4-bromobutyl)-1-ethyl-4,5-dihydro-3h-benzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC3=C2C1(CCCCBr)C(=O)N3CC OJYTXMKMQSNBNA-UHFFFAOYSA-N 0.000 description 2
• LESDSISTSSTPBO-UHFFFAOYSA-N 2a-[4-(1,2,4,4a,5,6-hexahydropyrazino[1,2-a]quinoxalin-3-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1C2CNC3=CC=CC=C3N2CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 LESDSISTSSTPBO-UHFFFAOYSA-N 0.000 description 2
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
• ZPIFAYFILYYZIG-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-pyrazolo[4,3-c]pyridine;dihydrochloride Chemical compound Cl.Cl.C1NCCC2=C1C=NN2 ZPIFAYFILYYZIG-UHFFFAOYSA-N 0.000 description 2
• YUHGQAJWDAKLGV-UHFFFAOYSA-N 4,5,6,7-tetrahydro-3h-imidazo[4,5-c]pyridine;hydrate;dihydrochloride Chemical compound O.Cl.Cl.C1NCCC2=C1NC=N2 YUHGQAJWDAKLGV-UHFFFAOYSA-N 0.000 description 2
• ZKAYEFAKZWTAGS-UHFFFAOYSA-N 4,5,6,7-tetrahydrofuro[2,3-c]pyridine Chemical compound C1NCCC2=C1OC=C2 ZKAYEFAKZWTAGS-UHFFFAOYSA-N 0.000 description 2
• HXNOEHIMWZDRTK-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[2,3-c]pyridine Chemical compound C1NCCC2=C1SC=C2 HXNOEHIMWZDRTK-UHFFFAOYSA-N 0.000 description 2
• ANKLNNCOMMHGOL-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide Chemical compound C1NCCC2=C1C=C(C(=O)N)S2 ANKLNNCOMMHGOL-UHFFFAOYSA-N 0.000 description 2
• MEYKBMVFEXLJDF-UHFFFAOYSA-N 4-(2,3-dihydro-1h-inden-1-yl)piperidine;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2C1C1CCNCC1 MEYKBMVFEXLJDF-UHFFFAOYSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
• FZUMQCKAVKSWLQ-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinolin-5-ol Chemical compound N1=CC=C2C(O)CCCC2=C1 FZUMQCKAVKSWLQ-UHFFFAOYSA-N 0.000 description 2
• WBIXPHWUULORGW-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinolin-5-yl acetate Chemical compound N1=CC=C2C(OC(=O)C)CCCC2=C1 WBIXPHWUULORGW-UHFFFAOYSA-N 0.000 description 2
• YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 description 2
• MRHRDZQVWVKPIJ-UHFFFAOYSA-N 5-benzyl-6,7-dihydro-4h-furo[3,2-c]pyridine Chemical compound C1CC=2OC=CC=2CN1CC1=CC=CC=C1 MRHRDZQVWVKPIJ-UHFFFAOYSA-N 0.000 description 2
• HPLVZHZIUJGIDQ-UHFFFAOYSA-N 5-fluoro-1,2,3,4-tetrahydroisoquinoline Chemical compound C1NCCC2=C1C=CC=C2F HPLVZHZIUJGIDQ-UHFFFAOYSA-N 0.000 description 2
• ZZGXLZYBHQFPQV-UHFFFAOYSA-N 5-fluoro-3,4-dihydro-2h-isoquinolin-1-one Chemical compound O=C1NCCC2=C1C=CC=C2F ZZGXLZYBHQFPQV-UHFFFAOYSA-N 0.000 description 2
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 2
• ZBNIQZCMPPVSKL-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-ol Chemical compound OC1CCCCC2=CC=CC=C12 ZBNIQZCMPPVSKL-UHFFFAOYSA-N 0.000 description 2
• KWHUHTFXMNQHAA-UHFFFAOYSA-N 6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CCCCC2=CC=CC=C12 KWHUHTFXMNQHAA-UHFFFAOYSA-N 0.000 description 2
• NKFNEIYWSQIOLY-UHFFFAOYSA-N 7-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1CCC(O)C2=CC(OC)=CC=C21 NKFNEIYWSQIOLY-UHFFFAOYSA-N 0.000 description 2
• JJDAWRNLQIOJMC-UHFFFAOYSA-N 9-(methoxymethyl)-1,2,3,4-tetrahydropyrido[3,4-b]indole Chemical compound C12=CC=CC=C2N(COC)C2=C1CCNC2 JJDAWRNLQIOJMC-UHFFFAOYSA-N 0.000 description 2
• NIVCAESKRVQXBZ-UHFFFAOYSA-N 9-propan-2-yl-1,2,3,4-tetrahydropyrido[3,4-b]indole;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C(C)C)C2=C1CCNC2 NIVCAESKRVQXBZ-UHFFFAOYSA-N 0.000 description 2
• 208000019901 Anxiety disease Diseases 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
• 208000020925 Bipolar disease Diseases 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
• 208000024172 Cardiovascular disease Diseases 0.000 description 2
• XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
• 208000018522 Gastrointestinal disease Diseases 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• CEIXWJHURKEBMQ-UHFFFAOYSA-N Heliamine Chemical compound C1CNCC2=C1C=C(OC)C(OC)=C2 CEIXWJHURKEBMQ-UHFFFAOYSA-N 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• 206010020772 Hypertension Diseases 0.000 description 2
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
• 208000019695 Migraine disease Diseases 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
• 239000007832 Na2SO4 Substances 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• MWDCNELMZRFPEA-UHFFFAOYSA-N [O-]C(=O)C(F)(F)F.C1=[NH+]C=C2SC=CC2=C1 Chemical compound [O-]C(=O)C(F)(F)F.C1=[NH+]C=C2SC=CC2=C1 MWDCNELMZRFPEA-UHFFFAOYSA-N 0.000 description 2
• 239000004480 active ingredient Substances 0.000 description 2
• 150000001266 acyl halides Chemical class 0.000 description 2
• 229910052783 alkali metal Inorganic materials 0.000 description 2
• 150000001340 alkali metals Chemical class 0.000 description 2
• 150000001336 alkenes Chemical class 0.000 description 2
• 150000001350 alkyl halides Chemical class 0.000 description 2
• 239000002168 alkylating agent Substances 0.000 description 2
• 229940100198 alkylating agent Drugs 0.000 description 2
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 125000003277 amino group Chemical group 0.000 description 2
• 230000036506 anxiety Effects 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 239000003849 aromatic solvent Substances 0.000 description 2
• 150000005130 benzoxazines Chemical class 0.000 description 2
• QVZDETYQBCKQGQ-UHFFFAOYSA-N benzyl 6-(2,2,2-trifluoroacetyl)-2,4,4a,5-tetrahydro-1h-pyrazino[1,2-a]quinoxaline-3-carboxylate Chemical compound C1CN2C3=CC=CC=C3N(C(=O)C(F)(F)F)CC2CN1C(=O)OCC1=CC=CC=C1 QVZDETYQBCKQGQ-UHFFFAOYSA-N 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
• MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
• RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• 210000004027 cell Anatomy 0.000 description 2
• 239000001913 cellulose Substances 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 238000005660 chlorination reaction Methods 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 229940061627 chloromethyl methyl ether Drugs 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• 150000002009 diols Chemical class 0.000 description 2
• 239000007884 disintegrant Substances 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 238000007336 electrophilic substitution reaction Methods 0.000 description 2
• 206010015037 epilepsy Diseases 0.000 description 2
• UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 150000004820 halides Chemical class 0.000 description 2
• RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 description 2
• 125000000623 heterocyclic group Chemical group 0.000 description 2
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
• QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 2
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 2
• 229960005417 ketanserin Drugs 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• 239000012280 lithium aluminium hydride Substances 0.000 description 2
• 239000000314 lubricant Substances 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 239000012528 membrane Substances 0.000 description 2
• UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
• QJBXIDGMNXAENX-UHFFFAOYSA-N methyl 1,2,3,4-tetrahydropyrido[3,4-b]indole-9-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(C(=O)OC)C2=C1CCNC2 QJBXIDGMNXAENX-UHFFFAOYSA-N 0.000 description 2
• YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
• ZNIXEVSMQRBBEM-UHFFFAOYSA-N methyl 3-fluoro-2-methylbenzoate Chemical compound COC(=O)C1=CC=CC(F)=C1C ZNIXEVSMQRBBEM-UHFFFAOYSA-N 0.000 description 2
• 206010027599 migraine Diseases 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• QBPIDNWMEBXNOZ-UHFFFAOYSA-N morpholin-4-yl(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)methanone Chemical compound C=1C=2CNCCC=2SC=1C(=O)N1CCOCC1 QBPIDNWMEBXNOZ-UHFFFAOYSA-N 0.000 description 2
• 239000012452 mother liquor Substances 0.000 description 2
• WAFCDFXWCIATEV-UHFFFAOYSA-N n,n-diethyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-9-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(C(=O)N(CC)CC)C2=C1CCNC2 WAFCDFXWCIATEV-UHFFFAOYSA-N 0.000 description 2
• XMKPBADOQMDELY-UHFFFAOYSA-N n-benzyl-2-chloro-n-(furan-3-ylmethyl)ethanamine Chemical compound C=1C=CC=CC=1CN(CCCl)CC=1C=COC=1 XMKPBADOQMDELY-UHFFFAOYSA-N 0.000 description 2
• LTDNALOFCQTDGS-UHFFFAOYSA-N n-methyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-9-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(C(=O)NC)C2=C1CCNC2 LTDNALOFCQTDGS-UHFFFAOYSA-N 0.000 description 2
• GSJRUEBQWPLHSN-UHFFFAOYSA-N n-methylmethanamine;oxolane Chemical compound CNC.C1CCOC1 GSJRUEBQWPLHSN-UHFFFAOYSA-N 0.000 description 2
• 239000012454 non-polar solvent Substances 0.000 description 2
• 230000009871 nonspecific binding Effects 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 239000012285 osmium tetroxide Substances 0.000 description 2
• 229910000489 osmium tetroxide Inorganic materials 0.000 description 2
• 229910052763 palladium Inorganic materials 0.000 description 2
• QYMDEOQLJUUNOF-UHFFFAOYSA-N pinoline Chemical compound C1NCCC2=C1NC1=CC=C(OC)C=C12 QYMDEOQLJUUNOF-UHFFFAOYSA-N 0.000 description 2
• RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 230000033764 rhythmic process Effects 0.000 description 2
• 201000000980 schizophrenia Diseases 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• 208000019116 sleep disease Diseases 0.000 description 2
• 229910052938 sodium sulfate Inorganic materials 0.000 description 2
• 235000011152 sodium sulphate Nutrition 0.000 description 2
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
• 235000019345 sodium thiosulphate Nutrition 0.000 description 2
• 230000009870 specific binding Effects 0.000 description 2
• 150000003457 sulfones Chemical class 0.000 description 2
• 150000003462 sulfoxides Chemical class 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• FTIBIIQRTFOCKU-UHFFFAOYSA-N tert-butyl 2-(dimethylcarbamoyl)-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C=C(C(=O)N(C)C)S2 FTIBIIQRTFOCKU-UHFFFAOYSA-N 0.000 description 2
• GDBLVYAUPNQGLX-UHFFFAOYSA-N tert-butyl 2-(morpholine-4-carbonyl)-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carboxylate Chemical compound C=1C=2CN(C(=O)OC(C)(C)C)CCC=2SC=1C(=O)N1CCOCC1 GDBLVYAUPNQGLX-UHFFFAOYSA-N 0.000 description 2
• WMKIJUGTZNCUGS-UHFFFAOYSA-N tert-butyl 2-methyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-5-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C=C(C)S2 WMKIJUGTZNCUGS-UHFFFAOYSA-N 0.000 description 2
• XKQYXBJGGJFVTI-UHFFFAOYSA-N tert-butyl 4-(1,2,3,4-tetrahydronaphthalen-1-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1C2=CC=CC=C2CCC1 XKQYXBJGGJFVTI-UHFFFAOYSA-N 0.000 description 2
• VHUZTMWZJJEDSH-UHFFFAOYSA-N tert-butyl 4-(1-phenylethyl)piperazine-1-carboxylate Chemical compound C=1C=CC=CC=1C(C)N1CCN(C(=O)OC(C)(C)C)CC1 VHUZTMWZJJEDSH-UHFFFAOYSA-N 0.000 description 2
• LVQINCFYBNICFN-UHFFFAOYSA-N tert-butyl 4-(5,6,7,8-tetrahydroisoquinolin-5-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1C2=CC=NC=C2CCC1 LVQINCFYBNICFN-UHFFFAOYSA-N 0.000 description 2
• QUVMORDMIXPNQY-UHFFFAOYSA-N tert-butyl 4-(5,6,7,8-tetrahydroquinolin-8-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1C2=NC=CC=C2CCC1 QUVMORDMIXPNQY-UHFFFAOYSA-N 0.000 description 2
• OYWWVJOCHKUCCD-UHFFFAOYSA-N tert-butyl 4-(5-oxo-6,7,8,9-tetrahydrobenzo[7]annulen-9-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1C2=CC=CC=C2C(=O)CCC1 OYWWVJOCHKUCCD-UHFFFAOYSA-N 0.000 description 2
• NPUBWBLLXPSYQM-UHFFFAOYSA-N tert-butyl 4-(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)piperazine-1-carboxylate Chemical compound C12=CC(OC)=CC=C2CCCC1N1CCN(C(=O)OC(C)(C)C)CC1 NPUBWBLLXPSYQM-UHFFFAOYSA-N 0.000 description 2
• DPEQXCDBCMRTGN-UHFFFAOYSA-N tert-butyl 6,7-dihydroxy-1-methyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound OC1=C(O)C=C2C(C)N(C(=O)OC(C)(C)C)CCC2=C1 DPEQXCDBCMRTGN-UHFFFAOYSA-N 0.000 description 2
• MFXHRPOAIOBJIE-UHFFFAOYSA-N tert-butyl 9-(2-acetyloxyethyl)-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(CCOC(=O)C)C2=C1CCN(C(=O)OC(C)(C)C)C2 MFXHRPOAIOBJIE-UHFFFAOYSA-N 0.000 description 2
• UGPQJNQXWDLXRL-UHFFFAOYSA-N tert-butyl 9-(2-amino-2-oxoethyl)-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound NC(=O)CN1C2=CC=CC=C2C2=C1CN(C(=O)OC(C)(C)C)CC2 UGPQJNQXWDLXRL-UHFFFAOYSA-N 0.000 description 2
• DMZZDPJXWVNTNN-UHFFFAOYSA-N tert-butyl 9-(2-oxopropyl)-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(CC(=O)C)C2=C1CCN(C(=O)OC(C)(C)C)C2 DMZZDPJXWVNTNN-UHFFFAOYSA-N 0.000 description 2
• IHSOMTNHPMNCHB-UHFFFAOYSA-N tert-butyl 9-(diethylcarbamoyl)-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)N(CC)CC)C2=C1CCN(C(=O)OC(C)(C)C)C2 IHSOMTNHPMNCHB-UHFFFAOYSA-N 0.000 description 2
• PXGISSSWOQHYKC-UHFFFAOYSA-N tert-butyl 9-(dimethylcarbamoyl)-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)N(C)C)C2=C1CCN(C(=O)OC(C)(C)C)C2 PXGISSSWOQHYKC-UHFFFAOYSA-N 0.000 description 2
• FNVKUFZOQHVNKW-UHFFFAOYSA-N tert-butyl 9-(methoxymethyl)-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(COC)C2=C1CCN(C(=O)OC(C)(C)C)C2 FNVKUFZOQHVNKW-UHFFFAOYSA-N 0.000 description 2
• ZEEPAWDCVUITOJ-UHFFFAOYSA-N tert-butyl 9-(methylcarbamoyl)-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)NC)C2=C1CCN(C(=O)OC(C)(C)C)C2 ZEEPAWDCVUITOJ-UHFFFAOYSA-N 0.000 description 2
• NCDPBKRHARSTAX-UHFFFAOYSA-N tert-butyl 9-[2-(dimethylamino)-2-oxoethyl]-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(CC(=O)N(C)C)C2=C1CCN(C(=O)OC(C)(C)C)C2 NCDPBKRHARSTAX-UHFFFAOYSA-N 0.000 description 2
• SUJUERLBBIRWPZ-UHFFFAOYSA-N tert-butyl 9-acetyl-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)C)C2=C1CCN(C(=O)OC(C)(C)C)C2 SUJUERLBBIRWPZ-UHFFFAOYSA-N 0.000 description 2
• DLBSVUIHZJSLMT-UHFFFAOYSA-N tert-butyl 9-benzyl-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C2=CC=CC=C22)=C1N2CC1=CC=CC=C1 DLBSVUIHZJSLMT-UHFFFAOYSA-N 0.000 description 2
• UZXAKNSTLHWZRX-UHFFFAOYSA-N tert-butyl 9-carbamoyl-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound NC(=O)N1C2=CC=CC=C2C2=C1CN(C(=O)OC(C)(C)C)CC2 UZXAKNSTLHWZRX-UHFFFAOYSA-N 0.000 description 2
• KZJNIEOORDJITI-UHFFFAOYSA-N tert-butyl 9-methyl-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(C)C2=C1CCN(C(=O)OC(C)(C)C)C2 KZJNIEOORDJITI-UHFFFAOYSA-N 0.000 description 2
• RSAGSUMROALRRZ-UHFFFAOYSA-N tert-butyl n-(3,4-dihydro-2h-1,4-benzothiazin-3-ylmethyl)carbamate Chemical compound C1=CC=C2NC(CNC(=O)OC(C)(C)C)CSC2=C1 RSAGSUMROALRRZ-UHFFFAOYSA-N 0.000 description 2
• RCLVCCSIVMNZTF-UHFFFAOYSA-N tert-butyl n-[[4-(2-chloroacetyl)-2,3-dihydro-1,4-benzothiazin-3-yl]methyl]carbamate Chemical compound C1=CC=C2N(C(=O)CCl)C(CNC(=O)OC(C)(C)C)CSC2=C1 RCLVCCSIVMNZTF-UHFFFAOYSA-N 0.000 description 2
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 125000005270 trialkylamine group Chemical group 0.000 description 2
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
• SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical class COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
• ZGRLKUNDSJJMKD-UHFFFAOYSA-N 1,2,3,4,4a,5-hexahydropyrazino[2,1-c][1,4]benzoxazine;hydrochloride Chemical compound Cl.C1=CC=C2N3CCNCC3COC2=C1 ZGRLKUNDSJJMKD-UHFFFAOYSA-N 0.000 description 1
• FRZDVWUAWCOHDI-UHFFFAOYSA-N 1,2,3,4,4a,6-hexahydropyrazino[1,2-a]quinoxalin-5-one Chemical group C1CNCC2C(=O)NC3=CC=CC=C3N21 FRZDVWUAWCOHDI-UHFFFAOYSA-N 0.000 description 1
• JAAJQSRLGAYGKZ-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2C(O)CCCC2=C1 JAAJQSRLGAYGKZ-UHFFFAOYSA-N 0.000 description 1
• HRVRAYIYXRVAPR-UHFFFAOYSA-N 1,3,4,5-tetrahydro-1-benzazepin-2-one Chemical compound N1C(=O)CCCC2=CC=CC=C21 HRVRAYIYXRVAPR-UHFFFAOYSA-N 0.000 description 1
• VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
• DLLBLNFCUXJHHV-UHFFFAOYSA-N 1-(1,2,3,4-tetrahydronaphthalen-1-yl)piperazine Chemical compound C12=CC=CC=C2CCCC1N1CCNCC1 DLLBLNFCUXJHHV-UHFFFAOYSA-N 0.000 description 1
• ABMZSHYXRIBZEZ-UHFFFAOYSA-N 1-(1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)ethanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(C(=O)C)C2=C1CCNC2 ABMZSHYXRIBZEZ-UHFFFAOYSA-N 0.000 description 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
• UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 1
• AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 1
• MGKPCLNUSDGXGT-UHFFFAOYSA-N 1-benzofuran-3-one Chemical compound C1=CC=C2C(=O)COC2=C1 MGKPCLNUSDGXGT-UHFFFAOYSA-N 0.000 description 1
• DIRTUFVVQCBEDV-UHFFFAOYSA-N 1-benzyl-4-(2-phenylpropan-2-yl)piperazine Chemical compound C=1C=CC=CC=1C(C)(C)N(CC1)CCN1CC1=CC=CC=C1 DIRTUFVVQCBEDV-UHFFFAOYSA-N 0.000 description 1
• MLEGMEBCXGDFQT-UHFFFAOYSA-N 1-benzylpiperidin-2-one Chemical compound O=C1CCCCN1CC1=CC=CC=C1 MLEGMEBCXGDFQT-UHFFFAOYSA-N 0.000 description 1
• HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
• WSXIDSNEEOYBFA-UHFFFAOYSA-N 1-bromopent-1-ene Chemical compound CCCC=CBr WSXIDSNEEOYBFA-UHFFFAOYSA-N 0.000 description 1
• UWDCUCCPBLHLTI-UHFFFAOYSA-N 1-fluoropyridin-1-ium Chemical class F[N+]1=CC=CC=C1 UWDCUCCPBLHLTI-UHFFFAOYSA-N 0.000 description 1
• OGMGXKJQIOUTTB-UHFFFAOYSA-N 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide Chemical compound Br.OC1=C(O)C=C2C(C)NCCC2=C1 OGMGXKJQIOUTTB-UHFFFAOYSA-N 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• LLWVQXHVPIIHDZ-UHFFFAOYSA-N 1-methyl-2a,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC3=C2C1C(=O)N3C LLWVQXHVPIIHDZ-UHFFFAOYSA-N 0.000 description 1
• BEUJAVGQOANFRI-UHFFFAOYSA-N 1h-indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2NC=CC2=C1 BEUJAVGQOANFRI-UHFFFAOYSA-N 0.000 description 1
• MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
• SIQBPWRTJNBBER-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-2-benzazepine Chemical compound C1CCNCC2=CC=CC=C21 SIQBPWRTJNBBER-UHFFFAOYSA-N 0.000 description 1
• CFTOTSJVQRFXOF-JZRMKITLSA-N 2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical class N1C2=CC=CC=C2C2=C1[11CH2]NCC2 CFTOTSJVQRFXOF-JZRMKITLSA-N 0.000 description 1
• CVQSWZMJOGOPAV-UHFFFAOYSA-N 2,3-dihydrothiochromen-4-one Chemical compound C1=CC=C2C(=O)CCSC2=C1 CVQSWZMJOGOPAV-UHFFFAOYSA-N 0.000 description 1
• NNPSOAOENINXMR-UHFFFAOYSA-N 2,3-dimethyl-2,3-dihydro-1h-indole Chemical compound C1=CC=C2C(C)C(C)NC2=C1 NNPSOAOENINXMR-UHFFFAOYSA-N 0.000 description 1
• ULCHUSIKHCWCSZ-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(CC(=O)N)C2=C1CCNC2 ULCHUSIKHCWCSZ-UHFFFAOYSA-N 0.000 description 1
• GYLGMZAXBOCBSQ-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)ethyl acetate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(CCOC(=O)C)C2=C1CCNC2 GYLGMZAXBOCBSQ-UHFFFAOYSA-N 0.000 description 1
• BJAJKVZABJZXDC-UHFFFAOYSA-N 2-(1-benzofuran-3-yl)acetonitrile Chemical compound C1=CC=C2C(CC#N)=COC2=C1 BJAJKVZABJZXDC-UHFFFAOYSA-N 0.000 description 1
• DVADEBQIGFNXNC-UHFFFAOYSA-N 2-[2-[4-(2-oxo-1,3,4,5-tetrahydrobenzo[cd]indol-2a-yl)butyl]-3,4-dihydro-1h-pyrido[3,4-b]indol-9-yl]acetonitrile Chemical compound N#CCN1C2=CC=CC=C2C(CC2)=C1CN2CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 DVADEBQIGFNXNC-UHFFFAOYSA-N 0.000 description 1
• VWUKDNSEDPMMFR-UHFFFAOYSA-N 2-[4-(2-oxo-1,3,4,5-tetrahydrobenzo[cd]indol-2a-yl)butyl]-3,4-dihydro-1h-pyrido[3,4-b]indole-9-carboxamide Chemical compound C12=CC=CC=C2N(C(=O)N)C2=C1CCN(CCCCC13C(NC=4C=CC=C(C3=4)CCC1)=O)C2 VWUKDNSEDPMMFR-UHFFFAOYSA-N 0.000 description 1
• LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
• RGHQKFQZGLKBCF-UHFFFAOYSA-N 2-bromoethyl acetate Chemical compound CC(=O)OCCBr RGHQKFQZGLKBCF-UHFFFAOYSA-N 0.000 description 1
• WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
• PXFVJRYQSXKFJX-UHFFFAOYSA-N 2-methyl-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridine Chemical compound C1NCCC2=NN(C)C=C21 PXFVJRYQSXKFJX-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• DMWUYLTUCJIKFV-UHFFFAOYSA-N 2a-[3-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)propyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound N1C2=CC=CC=C2C(CC2)=C1CN2CCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 DMWUYLTUCJIKFV-UHFFFAOYSA-N 0.000 description 1
• FDHWGBQQOFQIKJ-UHFFFAOYSA-N 2a-[4-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound N1C2=CC=CC=C2C(CC2)=C1CN2CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 FDHWGBQQOFQIKJ-UHFFFAOYSA-N 0.000 description 1
• RTLYDCLNWRVYQW-UHFFFAOYSA-N 2a-[4-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound O=C1NC(C2=3)=CC=CC=3CCCC12CCCCN(C1)CCC2=C1C=NN2 RTLYDCLNWRVYQW-UHFFFAOYSA-N 0.000 description 1
• WUGZCZDBNJRMIS-UHFFFAOYSA-N 2a-[4-(2,3-dimethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-5-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCC1NCC(SC(=C2C)C)=C2C1 WUGZCZDBNJRMIS-UHFFFAOYSA-N 0.000 description 1
• QBBSYFPUMYVOEE-UHFFFAOYSA-N 2a-[4-(2,4,4a,5-tetrahydro-1h-pyrazino[2,1-c][1,4]benzothiazin-3-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1C2CSC3=CC=CC=C3N2CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 QBBSYFPUMYVOEE-UHFFFAOYSA-N 0.000 description 1
• ZEJVRNLENIYKIL-UHFFFAOYSA-N 2a-[4-(2-methyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCN1CC(C=C(S2)C)=C2CC1 ZEJVRNLENIYKIL-UHFFFAOYSA-N 0.000 description 1
• JHEHDPXSLYHDAB-UHFFFAOYSA-N 2a-[4-(3,4-dihydro-1h-isoquinolin-2-yl)butyl]-1-ethyl-4,5-dihydro-3h-benzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC3=C2C1(CCCCN1CC2=CC=CC=C2CC1)C(=O)N3CC JHEHDPXSLYHDAB-UHFFFAOYSA-N 0.000 description 1
• YIPRVVVARXKUOR-UHFFFAOYSA-N 2a-[4-(3-methyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCN1CCC(SC=C2C)=C2C1 YIPRVVVARXKUOR-UHFFFAOYSA-N 0.000 description 1
• ZIMYOHPDDZSLCP-UHFFFAOYSA-N 2a-[4-(4-benzylpiperazin-1-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound O=C1NC(C2=3)=CC=CC=3CCCC12CCCCN(CC1)CCN1CC1=CC=CC=C1 ZIMYOHPDDZSLCP-UHFFFAOYSA-N 0.000 description 1
• IGYDTTJVYFLZMJ-UHFFFAOYSA-N 2a-[4-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound O=C1NC(C2=3)=CC=CC=3CCCC12CCCCN(C1)CCC2=C1SC=C2 IGYDTTJVYFLZMJ-UHFFFAOYSA-N 0.000 description 1
• CTGTXVHAPZSAFB-UHFFFAOYSA-N 2a-[4-(5-fluoro-3,4-dihydro-1h-isoquinolin-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCN1CC(C=CC=C2F)=C2CC1 CTGTXVHAPZSAFB-UHFFFAOYSA-N 0.000 description 1
• HYPWGIMZDOLBLN-UHFFFAOYSA-N 2a-[4-(6,7-dihydro-4h-furo[3,2-c]pyridin-5-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound O=C1NC(C2=3)=CC=CC=3CCCC12CCCCN(C1)CCC2=C1C=CO2 HYPWGIMZDOLBLN-UHFFFAOYSA-N 0.000 description 1
• PSWCYJDXBLJOMH-UHFFFAOYSA-N 2a-[4-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound O=C1NC(C2=3)=CC=CC=3CCCC12CCCCN(C1)CCC2=C1C=CS2 PSWCYJDXBLJOMH-UHFFFAOYSA-N 0.000 description 1
• ACCXXSBGCCOECP-UHFFFAOYSA-N 2a-[4-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)butyl]-1-ethyl-4,5-dihydro-3h-benzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC3=C2C1(CCCCN1CC=2C=CSC=2CC1)C(=O)N3CC ACCXXSBGCCOECP-UHFFFAOYSA-N 0.000 description 1
• NKBNPAVRJIVQDG-UHFFFAOYSA-N 2a-[4-(6,7-dimethoxy-1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCN1CCC(C=C(C(=C2)OC)OC)=C2C1C NKBNPAVRJIVQDG-UHFFFAOYSA-N 0.000 description 1
• RYTJTOGZJOWSHG-UHFFFAOYSA-N 2a-[4-(6-hydroxy-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCN1CC(NC2=CC=C(C=C22)O)=C2CC1 RYTJTOGZJOWSHG-UHFFFAOYSA-N 0.000 description 1
• HIERSXGFUPMUMD-UHFFFAOYSA-N 2a-[4-(6-methoxy-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCN1CC(NC2=CC=C(C=C22)OC)=C2CC1 HIERSXGFUPMUMD-UHFFFAOYSA-N 0.000 description 1
• FNLVSYVCTGWSJL-UHFFFAOYSA-N 2a-[4-(9-acetyl-3,4-dihydro-1h-pyrido[3,4-b]indol-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C12=CC=CC=C2N(C(=O)C)C2=C1CCN(CCCCC13C(NC=4C=CC=C(C3=4)CCC1)=O)C2 FNLVSYVCTGWSJL-UHFFFAOYSA-N 0.000 description 1
• DEAYIVIBPAQZTC-UHFFFAOYSA-N 2a-[4-(9-benzyl-3,4-dihydro-1h-pyrido[3,4-b]indol-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound O=C1NC(C2=3)=CC=CC=3CCCC12CCCCN(C1)CCC(C2=CC=CC=C22)=C1N2CC1=CC=CC=C1 DEAYIVIBPAQZTC-UHFFFAOYSA-N 0.000 description 1
• AQPAEUIJRBRZNA-UHFFFAOYSA-N 2a-[4-(9-methyl-3,4-dihydro-1h-pyrido[3,4-b]indol-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C12=CC=CC=C2N(C)C2=C1CCN(CCCCC13C(NC=4C=CC=C(C3=4)CCC1)=O)C2 AQPAEUIJRBRZNA-UHFFFAOYSA-N 0.000 description 1
• VWLFNRQOYFQCTL-UHFFFAOYSA-N 2a-[4-(9-propan-2-yl-3,4-dihydro-1h-pyrido[3,4-b]indol-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C12=CC=CC=C2N(C(C)C)C2=C1CCN(CCCCC13C(NC=4C=CC=C(C3=4)CCC1)=O)C2 VWLFNRQOYFQCTL-UHFFFAOYSA-N 0.000 description 1
• LVWGARUEIWPFHE-UHFFFAOYSA-N 2a-[4-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC=C2C1N(CC1)CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 LVWGARUEIWPFHE-UHFFFAOYSA-N 0.000 description 1
• FTRXLNMUMKNABI-UHFFFAOYSA-N 2a-[4-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC=C2C1C(CC1)CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 FTRXLNMUMKNABI-UHFFFAOYSA-N 0.000 description 1
• LASYGKVLZHCNSR-UHFFFAOYSA-N 2a-[4-[4-(1-phenylethyl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CN(CCCCC23C(NC=4C=CC=C(C3=4)CCC2)=O)CCN1C(C)C1=CC=CC=C1 LASYGKVLZHCNSR-UHFFFAOYSA-N 0.000 description 1
• XLWSDZBXXPZYTI-UHFFFAOYSA-N 2a-[4-[4-(2,3-dihydro-1h-inden-1-yl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CC2=CC=CC=C2C1N(CC1)CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 XLWSDZBXXPZYTI-UHFFFAOYSA-N 0.000 description 1
• ASYWKPWDEWMLGE-UHFFFAOYSA-N 2a-[4-[4-(2-phenylpropan-2-yl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CN(CCCCC23C(NC=4C=CC=C(C3=4)CCC2)=O)CCN1C(C)(C)C1=CC=CC=C1 ASYWKPWDEWMLGE-UHFFFAOYSA-N 0.000 description 1
• RZPVYONZMVKUPR-UHFFFAOYSA-N 2a-[4-[4-(3,4-dihydro-1h-isoquinolin-2-yl)piperidin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CC2=CC=CC=C2CN1C(CC1)CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 RZPVYONZMVKUPR-UHFFFAOYSA-N 0.000 description 1
• UQUWGGRHWUNWEY-UHFFFAOYSA-N 2a-[4-[4-(3,4-dihydro-2h-chromen-4-yl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1COC2=CC=CC=C2C1N(CC1)CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 UQUWGGRHWUNWEY-UHFFFAOYSA-N 0.000 description 1
• VOMBPWMWAQUVPY-UHFFFAOYSA-N 2a-[4-[4-(3,4-dihydro-2h-thiochromen-4-yl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CSC2=CC=CC=C2C1N(CC1)CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 VOMBPWMWAQUVPY-UHFFFAOYSA-N 0.000 description 1
• AKQFDZGPKAQOAQ-UHFFFAOYSA-N 2a-[4-[4-(5,6,7,8-tetrahydroisoquinolin-5-yl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CN=CC=C2C1N(CC1)CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 AKQFDZGPKAQOAQ-UHFFFAOYSA-N 0.000 description 1
• NRKMJVFYEJLVSM-UHFFFAOYSA-N 2a-[4-[4-(5,6,7,8-tetrahydroquinolin-8-yl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CN=C2C1N(CC1)CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 NRKMJVFYEJLVSM-UHFFFAOYSA-N 0.000 description 1
• REUPTHJVJFTFOF-UHFFFAOYSA-N 2a-[4-[4-(5-oxo-6,7,8,9-tetrahydrobenzo[7]annulen-9-yl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC(=O)C2=CC=CC=C2C1N(CC1)CCN1CCCCC1(C(=O)N2)CCCC3=C1C2=CC=C3 REUPTHJVJFTFOF-UHFFFAOYSA-N 0.000 description 1
• FQSMCRWKKQQYGM-UHFFFAOYSA-N 2a-[4-[4-(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)piperazin-1-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCN(CC1)CCN1C1CCCC2=CC=C(OC)C=C21 FQSMCRWKKQQYGM-UHFFFAOYSA-N 0.000 description 1
• GPNDTWVUURBCBH-UHFFFAOYSA-N 2a-[4-[9-(2-hydroxyethyl)-3,4-dihydro-1h-pyrido[3,4-b]indol-2-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C12=CC=CC=C2N(CCO)C2=C1CCN(CCCCC13C(NC=4C=CC=C(C3=4)CCC1)=O)C2 GPNDTWVUURBCBH-UHFFFAOYSA-N 0.000 description 1
• CRRKLNGYPLRVMF-UHFFFAOYSA-N 2a-[4-[9-(methoxymethyl)-3,4-dihydro-1h-pyrido[3,4-b]indol-2-yl]butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C12=CC=CC=C2N(COC)C2=C1CCN(CCCCC13C(NC=4C=CC=C(C3=4)CCC1)=O)C2 CRRKLNGYPLRVMF-UHFFFAOYSA-N 0.000 description 1
• AHLXYZLFKAUGCX-UHFFFAOYSA-N 2a-pent-4-enyl-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound C1CCC2=CC=CC3=C2C1(CCCC=C)C(=O)N3 AHLXYZLFKAUGCX-UHFFFAOYSA-N 0.000 description 1
• HGENHKQBSARIQT-UHFFFAOYSA-N 2h-pyrazino[2,3-h][1,2]benzoxazine Chemical class C1=CC2=NC=CN=C2C2=C1C=CNO2 HGENHKQBSARIQT-UHFFFAOYSA-N 0.000 description 1
• WVFRBEVHVKERPG-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzothiazin-3-ylmethanamine Chemical compound C1=CC=C2NC(CN)CSC2=C1 WVFRBEVHVKERPG-UHFFFAOYSA-N 0.000 description 1
• FWVSZXYNCFXKRT-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromen-4-ol Chemical compound C1=CC=C2C(O)CCSC2=C1 FWVSZXYNCFXKRT-UHFFFAOYSA-N 0.000 description 1
• XMKZAIHFVHJGPV-UHFFFAOYSA-N 3-fluoro-2-methylbenzoic acid Chemical compound CC1=C(F)C=CC=C1C(O)=O XMKZAIHFVHJGPV-UHFFFAOYSA-N 0.000 description 1
• RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 1
• AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 description 1
• SKNBYROUCJKRDB-UHFFFAOYSA-N 3-methyl-4,5,6,7-tetrahydro-2h-pyrazolo[4,3-c]pyridine Chemical compound C1CNCC2=C1NN=C2C SKNBYROUCJKRDB-UHFFFAOYSA-N 0.000 description 1
• OBFVQLRWLPFYED-UHFFFAOYSA-N 3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine-2-carboxylic acid Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C(C)=C(C(O)=O)S2 OBFVQLRWLPFYED-UHFFFAOYSA-N 0.000 description 1
• NWCYECXHIYEBJE-UHFFFAOYSA-N 3-oxobutyl acetate Chemical compound CC(=O)CCOC(C)=O NWCYECXHIYEBJE-UHFFFAOYSA-N 0.000 description 1
• VGMJQHONPAXABH-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-pyrazolo[4,3-c]pyridine Chemical compound C1NCCC2=C1C=NN2 VGMJQHONPAXABH-UHFFFAOYSA-N 0.000 description 1
• URMVFILWXLQJIP-UHFFFAOYSA-N 4,5,6,7-tetrahydro-3h-imidazo[4,5-c]pyridine Chemical compound C1NCCC2=C1NC=N2 URMVFILWXLQJIP-UHFFFAOYSA-N 0.000 description 1
• ZDKHUQDELHMHFD-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxylic acid Chemical compound C1CNCC2=C1C=C(C(=O)O)S2 ZDKHUQDELHMHFD-UHFFFAOYSA-N 0.000 description 1
• OEYJTWUFGQRSOD-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-ium-2-carboxylate Chemical compound C1NCCC2=C1C=C(C(=O)O)S2 OEYJTWUFGQRSOD-UHFFFAOYSA-N 0.000 description 1
• MWZDFPMMKQJYFB-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1NCCC2=C1C=C(C(=O)O)S2 MWZDFPMMKQJYFB-UHFFFAOYSA-N 0.000 description 1
• CUUPTAYSCIOICO-UHFFFAOYSA-N 4-(2-oxo-1,3,4,5-tetrahydrobenzo[cd]indol-2a-yl)butanal Chemical compound C1CCC2=CC=CC3=C2C1(CCCC=O)C(=O)N3 CUUPTAYSCIOICO-UHFFFAOYSA-N 0.000 description 1
• MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 1
• ABGXADJDTPFFSZ-UHFFFAOYSA-N 4-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCNCC1 ABGXADJDTPFFSZ-UHFFFAOYSA-N 0.000 description 1
• MPZMVUQGXAOJIK-UHFFFAOYSA-N 4-bromopyridine;hydron;chloride Chemical compound Cl.BrC1=CC=NC=C1 MPZMVUQGXAOJIK-UHFFFAOYSA-N 0.000 description 1
• YRKLJYRHSRRSMH-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4h-furo[2,3-c]azepine Chemical compound C1CCNCC2=C1C=CO2 YRKLJYRHSRRSMH-UHFFFAOYSA-N 0.000 description 1
• ZFSYBODWGHEZST-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4h-furo[2,3-d]azepine Chemical compound C1CNCCC2=C1OC=C2 ZFSYBODWGHEZST-UHFFFAOYSA-N 0.000 description 1
• GVLUAKKYTJQALV-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4h-thieno[2,3-c]azepine-2-carboxylic acid Chemical compound C1CCNCC2=C1C=C(C(=O)O)S2 GVLUAKKYTJQALV-UHFFFAOYSA-N 0.000 description 1
• RCTKBWSGKTWLFI-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4h-thieno[3,2-c]azepine-2-carboxylic acid Chemical compound C1NCCCC2=C1C=C(C(=O)O)S2 RCTKBWSGKTWLFI-UHFFFAOYSA-N 0.000 description 1
• HTMGQIXFZMZZKD-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinoline Chemical compound N1=CC=C2CCCCC2=C1 HTMGQIXFZMZZKD-UHFFFAOYSA-N 0.000 description 1
• 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 1
• 108091005479 5-HT2 receptors Proteins 0.000 description 1
• RYYDMZOUDODRDJ-UHFFFAOYSA-N 5-[4-(2-oxo-1,3,4,5-tetrahydrobenzo[cd]indol-2a-yl)butyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine-2-carboxamide Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCN1CC(C=C(S2)C(=O)N)=C2CC1 RYYDMZOUDODRDJ-UHFFFAOYSA-N 0.000 description 1
• 102100040368 5-hydroxytryptamine receptor 6 Human genes 0.000 description 1
• 101710150235 5-hydroxytryptamine receptor 6 Proteins 0.000 description 1
• IFDIAPORDJTSKP-UHFFFAOYSA-N 5-methoxynaphthalene-1-carbonitrile Chemical compound C1=CC=C2C(OC)=CC=CC2=C1C#N IFDIAPORDJTSKP-UHFFFAOYSA-N 0.000 description 1
• QGELVLBHMKUSTG-UHFFFAOYSA-N 6-bromo-2a-[4-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)butyl]-1,3,4,5-tetrahydrobenzo[cd]indol-2-one Chemical compound N1C2=CC=CC=C2C(CC2)=C1CN2CCCCC1(CCC2)C(=O)NC3=CC=C(Br)C2=C31 QGELVLBHMKUSTG-UHFFFAOYSA-N 0.000 description 1
• BDCCXYVTXRUGAN-UHFFFAOYSA-N 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline Chemical compound FC1=CC=C2NC(C)CCC2=C1 BDCCXYVTXRUGAN-UHFFFAOYSA-N 0.000 description 1
• PTENEIBPTFISMR-UHFFFAOYSA-N 6-methyl-2,3,4,4a-tetrahydro-1h-pyrazino[1,2-a]quinoxalin-5-one;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C(=O)C2N1CCNC2 PTENEIBPTFISMR-UHFFFAOYSA-N 0.000 description 1
• GABLTKRIYDNDIN-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(OC)=CC=C21 GABLTKRIYDNDIN-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
• SROMRGBJXFAAJU-UHFFFAOYSA-N 9-benzyl-1,2,3,4-tetrahydropyrido[3,4-b]indole Chemical compound C1=2CNCCC=2C2=CC=CC=C2N1CC1=CC=CC=C1 SROMRGBJXFAAJU-UHFFFAOYSA-N 0.000 description 1
• ICUPRAORSPYZJU-UHFFFAOYSA-N 9-benzyl-1,2,3,4-tetrahydropyrido[3,4-b]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2CNCCC=2C2=CC=CC=C2N1CC1=CC=CC=C1 ICUPRAORSPYZJU-UHFFFAOYSA-N 0.000 description 1
• LISMJSXHYGUASA-UHFFFAOYSA-N 9-methyl-1,2,3,4-tetrahydropyrido[3,4-b]indole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(C)C2=C1CCNC2 LISMJSXHYGUASA-UHFFFAOYSA-N 0.000 description 1
• OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
• 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• 239000004375 Dextrin Substances 0.000 description 1
• 229920001353 Dextrin Polymers 0.000 description 1
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 239000001856 Ethyl cellulose Substances 0.000 description 1
• ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
• IXLJAHJIOOPXAR-UHFFFAOYSA-K F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.[O-]C(=O)C1=CC=CO1.[O-]C(=O)C1=CC=CO1.[O-]C(=O)C1=CC=CO1 Chemical compound F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.F[N+]1=CC=CC=C1.[O-]C(=O)C1=CC=CO1.[O-]C(=O)C1=CC=CO1.[O-]C(=O)C1=CC=CO1 IXLJAHJIOOPXAR-UHFFFAOYSA-K 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
• 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
• UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
• ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
• LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
• 238000006929 Pictet-Spengler synthesis reaction Methods 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 239000004372 Polyvinyl alcohol Substances 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 239000005708 Sodium hypochlorite Substances 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 230000006978 adaptation Effects 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 230000009435 amidation Effects 0.000 description 1
• 238000007112 amidation reaction Methods 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 238000007281 aminoalkylation reaction Methods 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 159000000032 aromatic acids Chemical class 0.000 description 1
• 239000012131 assay buffer Substances 0.000 description 1
• ANTGQBPGYZDWAW-UHFFFAOYSA-N azane;1,4-dioxane Chemical compound N.C1COCCO1 ANTGQBPGYZDWAW-UHFFFAOYSA-N 0.000 description 1
• 125000004321 azepin-2-yl group Chemical group [H]N1C([H])=C([H])C([H])=C([H])C([H])=C1* 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• YROCJIFUJHOTPE-UHFFFAOYSA-N benzyl 4-(3,4-dihydro-1h-isoquinolin-2-yl)piperidine-1-carboxylate Chemical compound C1CC(N2CC3=CC=CC=C3CC2)CCN1C(=O)OCC1=CC=CC=C1 YROCJIFUJHOTPE-UHFFFAOYSA-N 0.000 description 1
• GIZBAAGXMPSCPZ-UHFFFAOYSA-N benzyl 5-[4-(2-oxo-1,3,4,5-tetrahydrobenzo[cd]indol-2a-yl)butyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine-2-carboxylate Chemical compound C=1C=2CN(CCCCC34C(NC=5C=CC=C(C4=5)CCC3)=O)CCC=2SC=1C(=O)OCC1=CC=CC=C1 GIZBAAGXMPSCPZ-UHFFFAOYSA-N 0.000 description 1
• WCGBEFSZJSHDDX-UHFFFAOYSA-N benzyl 5-oxo-2,4,4a,6-tetrahydro-1h-pyrazino[1,2-a]quinoxaline-3-carboxylate Chemical compound C1CN(C2=CC=CC=C2NC2=O)C2CN1C(=O)OCC1=CC=CC=C1 WCGBEFSZJSHDDX-UHFFFAOYSA-N 0.000 description 1
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 208000028683 bipolar I disease Diseases 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 229920005557 bromobutyl Polymers 0.000 description 1
• 239000007853 buffer solution Substances 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
• 239000001354 calcium citrate Substances 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
• 238000005810 carbonylation reaction Methods 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 210000003710 cerebral cortex Anatomy 0.000 description 1
• KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
• 238000007385 chemical modification Methods 0.000 description 1
• 239000007806 chemical reaction intermediate Substances 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 238000003403 chloroformylation reaction Methods 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 230000006835 compression Effects 0.000 description 1
• 238000007906 compression Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 210000004748 cultured cell Anatomy 0.000 description 1
• IGMWDYQIKLLYQH-UHFFFAOYSA-N cyanomethyl diethyl phosphate Chemical compound CCOP(=O)(OCC)OCC#N IGMWDYQIKLLYQH-UHFFFAOYSA-N 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• 150000001991 dicarboxylic acids Chemical class 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
• NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• 238000002651 drug therapy Methods 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 125000003700 epoxy group Chemical group 0.000 description 1
• 125000005949 ethanesulfonyloxy group Chemical group 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• LLGOMIPFKKCDSD-UHFFFAOYSA-N ethyl 3-oxo-4-phenylsulfanylbutanoate Chemical compound CCOC(=O)CC(=O)CSC1=CC=CC=C1 LLGOMIPFKKCDSD-UHFFFAOYSA-N 0.000 description 1
• OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
• WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
• 235000019325 ethyl cellulose Nutrition 0.000 description 1
• 229920001249 ethyl cellulose Polymers 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 239000012530 fluid Substances 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 238000005187 foaming Methods 0.000 description 1
• 239000008098 formaldehyde solution Substances 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 230000002140 halogenating effect Effects 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
• PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
• 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 239000007927 intramuscular injection Substances 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229910001629 magnesium chloride Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000003340 mental effect Effects 0.000 description 1
• LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
• WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
• 229960004650 metergoline Drugs 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
• RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• DEHZQOLNSNVIHK-UHFFFAOYSA-N methyl 2-(1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)acetate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(CC(=O)OC)C2=C1CCNC2 DEHZQOLNSNVIHK-UHFFFAOYSA-N 0.000 description 1
• JZULUDYJULULLS-UHFFFAOYSA-N methyl 2-(bromomethyl)-3-fluorobenzoate Chemical compound COC(=O)C1=CC=CC(F)=C1CBr JZULUDYJULULLS-UHFFFAOYSA-N 0.000 description 1
• ZBNCXBRZFRYZMS-UHFFFAOYSA-N methyl 2-(cyanomethyl)-3-fluorobenzoate Chemical compound COC(=O)C1=CC=CC(F)=C1CC#N ZBNCXBRZFRYZMS-UHFFFAOYSA-N 0.000 description 1
• XTFUQNZBEFAKHW-UHFFFAOYSA-N methyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate;hydrochloride Chemical compound Cl.C1NCCC2=C1C=C(C(=O)OC)S2 XTFUQNZBEFAKHW-UHFFFAOYSA-N 0.000 description 1
• RDBQMDQEQBBROF-UHFFFAOYSA-N methyl 5-[4-(2-oxo-1,3,4,5-tetrahydrobenzo[cd]indol-2a-yl)butyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine-2-carboxylate Chemical compound C1CCC2=CC=CC(NC3=O)=C2C31CCCCN1CC(C=C(S2)C(=O)OC)=C2CC1 RDBQMDQEQBBROF-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• XIIQEOQKQGGTKI-UHFFFAOYSA-N n,n-diethyl-2-[4-(2-oxo-1,3,4,5-tetrahydrobenzo[cd]indol-2a-yl)butyl]-3,4-dihydro-1h-pyrido[3,4-b]indole-9-carboxamide Chemical compound C12=CC=CC=C2N(C(=O)N(CC)CC)C2=C1CCN(CCCCC13C(NC=4C=CC=C(C3=4)CCC1)=O)C2 XIIQEOQKQGGTKI-UHFFFAOYSA-N 0.000 description 1
• GLDFSSJVXDULKQ-UHFFFAOYSA-N n,n-dimethyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-9-carboxamide;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C(=O)N(C)C)C2=C1CCNC2 GLDFSSJVXDULKQ-UHFFFAOYSA-N 0.000 description 1
• UALFGRGWDLRGSM-UHFFFAOYSA-N n,n-dimethyl-2-(1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)acetamide Chemical compound C12=CC=CC=C2N(CC(=O)N(C)C)C2=C1CCNC2 UALFGRGWDLRGSM-UHFFFAOYSA-N 0.000 description 1
• VKRIABWUQIFJPH-UHFFFAOYSA-N n,n-dimethyl-2-(1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(CC(=O)N(C)C)C2=C1CCNC2 VKRIABWUQIFJPH-UHFFFAOYSA-N 0.000 description 1
• BNLDNEGQLKGZII-UHFFFAOYSA-N n,n-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide Chemical compound C1NCCC2=C1C=C(C(=O)N(C)C)S2 BNLDNEGQLKGZII-UHFFFAOYSA-N 0.000 description 1
• YDDVFDYCEFZGMB-UHFFFAOYSA-N n-(3,4-dihydro-2h-1,4-benzothiazin-3-ylmethyl)-4-hydroxybutanamide Chemical compound C1=CC=C2NC(CNC(=O)CCCO)CSC2=C1 YDDVFDYCEFZGMB-UHFFFAOYSA-N 0.000 description 1
• HYVHSMSLCFIRFA-UHFFFAOYSA-N n-(furan-3-ylmethyl)-1-phenylmethanamine Chemical compound C1=COC=C1CNCC1=CC=CC=C1 HYVHSMSLCFIRFA-UHFFFAOYSA-N 0.000 description 1
• METAARIXCOAZDH-UHFFFAOYSA-N n-cyclohexyl-1-(4-methylphenyl)methanimine Chemical compound C1=CC(C)=CC=C1C=NC1CCCCC1 METAARIXCOAZDH-UHFFFAOYSA-N 0.000 description 1
• ANWSCQFYUDOLCH-UHFFFAOYSA-N n-fluoro-4-methyl-n-propylbenzenesulfonamide Chemical class CCCN(F)S(=O)(=O)C1=CC=C(C)C=C1 ANWSCQFYUDOLCH-UHFFFAOYSA-N 0.000 description 1
• CJYQZTZSYREQBD-UHFFFAOYSA-N n-fluorobenzenesulfonamide Chemical compound FNS(=O)(=O)C1=CC=CC=C1 CJYQZTZSYREQBD-UHFFFAOYSA-N 0.000 description 1
• RUMHTMNQOVBBRY-UHFFFAOYSA-N n-methyl-2-(1,2,3,4-tetrahydropyrido[3,4-b]indol-9-yl)acetamide Chemical compound C12=CC=CC=C2N(CC(=O)NC)C2=C1CCNC2 RUMHTMNQOVBBRY-UHFFFAOYSA-N 0.000 description 1
• WLEXIGGRHOXDNF-UHFFFAOYSA-N n-methyl-2-[4-(2-oxo-1,3,4,5-tetrahydrobenzo[cd]indol-2a-yl)butyl]-3,4-dihydro-1h-pyrido[3,4-b]indole-9-carboxamide Chemical compound C12=CC=CC=C2N(C(=O)NC)C2=C1CCN(CCCCC13C(NC=4C=CC=C(C3=4)CCC1)=O)C2 WLEXIGGRHOXDNF-UHFFFAOYSA-N 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
• 230000035790 physiological processes and functions Effects 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920002451 polyvinyl alcohol Polymers 0.000 description 1
• 229920001289 polyvinyl ether Polymers 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
• 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
• 238000005063 solubilization Methods 0.000 description 1
• 230000007928 solubilization Effects 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 238000001179 sorption measurement Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• XXMUVWBKJNJFOF-UHFFFAOYSA-N tert-butyl 3,4-dihydro-1h-[1]benzothiolo[2,3-c]pyridine-2-carboxylate Chemical compound S1C2=CC=CC=C2C2=C1CN(C(=O)OC(C)(C)C)CC2 XXMUVWBKJNJFOF-UHFFFAOYSA-N 0.000 description 1
• YUSMZDVTEOAHDL-UHFFFAOYSA-N tert-butyl 3-(dimethylaminomethylidene)-4-oxopiperidine-1-carboxylate Chemical compound CN(C)C=C1CN(C(=O)OC(C)(C)C)CCC1=O YUSMZDVTEOAHDL-UHFFFAOYSA-N 0.000 description 1
• YALDBRAWOJVXRF-UHFFFAOYSA-N tert-butyl 4,5,6,7-tetrahydropyrazolo[4,3-c]pyridine-1-carboxylate Chemical compound C1NCCC2=C1C=NN2C(=O)OC(C)(C)C YALDBRAWOJVXRF-UHFFFAOYSA-N 0.000 description 1
• MPRVNFLYIVNNAN-UHFFFAOYSA-N tert-butyl 4-(3,4-dihydro-2h-chromen-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1OC2=CC=CC=C2CC1 MPRVNFLYIVNNAN-UHFFFAOYSA-N 0.000 description 1
• UBYLDYRKWSCXAQ-UHFFFAOYSA-N tert-butyl 4-(3,4-dihydro-2h-chromen-4-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1C2=CC=CC=C2OCC1 UBYLDYRKWSCXAQ-UHFFFAOYSA-N 0.000 description 1
• WAHYOSBZOHZMHV-UHFFFAOYSA-N tert-butyl 4-(3,4-dihydro-2h-thiochromen-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1SC2=CC=CC=C2CC1 WAHYOSBZOHZMHV-UHFFFAOYSA-N 0.000 description 1
• JGSGDDQOULGAKS-UHFFFAOYSA-N tert-butyl 4-(3,4-dihydro-2h-thiochromen-4-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1C2=CC=CC=C2SCC1 JGSGDDQOULGAKS-UHFFFAOYSA-N 0.000 description 1
• ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
• CRSHBCSIJWVDOT-UHFFFAOYSA-N tert-butyl 6,7-dimethoxy-1-methyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)C(C)C2=C1C=C(OC)C(OC)=C2 CRSHBCSIJWVDOT-UHFFFAOYSA-N 0.000 description 1
• HGSARGFDCSXUBC-UHFFFAOYSA-N tert-butyl 9-(cyanomethyl)-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound N#CCN1C2=CC=CC=C2C2=C1CN(C(=O)OC(C)(C)C)CC2 HGSARGFDCSXUBC-UHFFFAOYSA-N 0.000 description 1
• KMHNZGRISWSBEX-UHFFFAOYSA-N tert-butyl 9-[2-(methylamino)-2-oxoethyl]-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(CC(=O)NC)C2=C1CCN(C(=O)OC(C)(C)C)C2 KMHNZGRISWSBEX-UHFFFAOYSA-N 0.000 description 1
• CCHMUQRTLBOGLD-UHFFFAOYSA-N tert-butyl 9-propan-2-yl-3,4-dihydro-1h-pyrido[3,4-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(C(C)C)C2=C1CCN(C(=O)OC(C)(C)C)C2 CCHMUQRTLBOGLD-UHFFFAOYSA-N 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
• YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
• 235000013337 tricalcium citrate Nutrition 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 239000002023 wood Substances 0.000 description 1