MXPA98010331A - - Google Patents

Info

Publication number

MXPA98010331A

MXPA98010331A MXPA/A/1998/010331A MX9810331A MXPA98010331A MX PA98010331 A MXPA98010331 A MX PA98010331A MX 9810331 A MX9810331 A MX 9810331A MX PA98010331 A MXPA98010331 A MX PA98010331A

Authority

MX

Mexico

Prior art keywords

indole

tetrahydropyridin

mmol

benzothiophene

methyl

Prior art date

1998-12-07

Links

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• 150000001875 compounds Chemical class 0.000 claims description 315
• -1 2-methylphenoxy Chemical group 0.000 claims description 284
• 230000002829 reduced Effects 0.000 claims description 210
• 239000011541 reaction mixture Substances 0.000 claims description 174
• 239000000243 solution Substances 0.000 claims description 152
• 239000007787 solid Substances 0.000 claims description 150
• YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 144
• 239000000203 mixture Substances 0.000 claims description 141
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 136
• XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 126
• FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 90
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 90
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 86
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 84
• 239000000047 product Substances 0.000 claims description 72
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 72
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 68
• 238000006243 chemical reaction Methods 0.000 claims description 64
• 239000011780 sodium chloride Substances 0.000 claims description 62
• PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 60
• 229910052938 sodium sulfate Inorganic materials 0.000 claims description 60
• 235000011152 sodium sulphate Nutrition 0.000 claims description 60
• UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 56
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 56
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 56
• FCEHBMOGCRZNNI-UHFFFAOYSA-N Benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 52
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 52
• 238000003818 flash chromatography Methods 0.000 claims description 50
• 239000012074 organic phase Substances 0.000 claims description 50
• 239000000741 silica gel Substances 0.000 claims description 48
• 229910002027 silica gel Inorganic materials 0.000 claims description 48
• 238000002360 preparation method Methods 0.000 claims description 46
• 238000000034 method Methods 0.000 claims description 45
• MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 44
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 42
• 230000002401 inhibitory effect Effects 0.000 claims description 38
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
• 239000003921 oil Substances 0.000 claims description 36
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 claims description 34
• 238000010992 reflux Methods 0.000 claims description 34
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 32
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 32
• 201000010099 disease Diseases 0.000 claims description 30
• BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 claims description 30
• 229940076279 Serotonin Drugs 0.000 claims description 29
• 238000007792 addition Methods 0.000 claims description 28
• 238000006297 dehydration reaction Methods 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 235000017557 sodium bicarbonate Nutrition 0.000 claims description 28
• 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 28
• 239000002904 solvent Substances 0.000 claims description 28
• YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 26
• 230000000875 corresponding Effects 0.000 claims description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
• 239000012071 phase Substances 0.000 claims description 24
• 238000003756 stirring Methods 0.000 claims description 24
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 24
• 239000003814 drug Substances 0.000 claims description 22
• 229940079593 drugs Drugs 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 22
• 238000004587 chromatography analysis Methods 0.000 claims description 20
• VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 18
• 239000003112 inhibitor Substances 0.000 claims description 18
• CSRZQMIRAZTJOY-UHFFFAOYSA-N Trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 16
• 238000005984 hydrogenation reaction Methods 0.000 claims description 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
• 239000001184 potassium carbonate Substances 0.000 claims description 16
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 229960002464 Fluoxetine Drugs 0.000 claims description 14
• RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 claims description 14
• 230000002378 acidificating Effects 0.000 claims description 14
• 239000004480 active ingredient Substances 0.000 claims description 14
• 150000001450 anions Chemical class 0.000 claims description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
• 239000003054 catalyst Substances 0.000 claims description 14
• 239000006260 foam Substances 0.000 claims description 14
• 239000000463 material Substances 0.000 claims description 14
• 239000010452 phosphate Substances 0.000 claims description 14
• 239000000843 powder Substances 0.000 claims description 14
• 238000006722 reduction reaction Methods 0.000 claims description 14
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 125000005518 carboxamido group Chemical group 0.000 claims description 13
• 238000009472 formulation Methods 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• QDXQAOGNBCOEQX-UHFFFAOYSA-N 1-methylcyclohexa-1,4-diene Chemical compound CC1=CCC=CC1 QDXQAOGNBCOEQX-UHFFFAOYSA-N 0.000 claims description 12
• CIRSPTXGPFAXRE-UHFFFAOYSA-N 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Chemical class C1NCCC(C=2C3=CC=CC=C3NC=2)=C1 CIRSPTXGPFAXRE-UHFFFAOYSA-N 0.000 claims description 12
• VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-Piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 12
• MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
• ZCSHNCUQKCANBX-UHFFFAOYSA-N Lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 12
• NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 12
• VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 12
• 239000000908 ammonium hydroxide Substances 0.000 claims description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 239000000706 filtrate Substances 0.000 claims description 12
• 238000001914 filtration Methods 0.000 claims description 12
• 239000008079 hexane Substances 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
• 239000007858 starting material Substances 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
• VHNKCGJYSJENJZ-UHFFFAOYSA-N 3-bromo-5-chloro-1-benzothiophene Chemical compound ClC1=CC=C2SC=C(Br)C2=C1 VHNKCGJYSJENJZ-UHFFFAOYSA-N 0.000 claims description 10
• 238000002425 crystallisation Methods 0.000 claims description 10
• 230000005712 crystallization Effects 0.000 claims description 10
• 238000010511 deprotection reaction Methods 0.000 claims description 10
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 10
• VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 claims description 10
• 239000002480 mineral oil Substances 0.000 claims description 10
• 235000010446 mineral oil Nutrition 0.000 claims description 10
• 235000006408 oxalic acid Nutrition 0.000 claims description 10
• 229920005989 resin Polymers 0.000 claims description 10
• 239000011347 resin Substances 0.000 claims description 10
• 239000000758 substrate Substances 0.000 claims description 10
• 238000003786 synthesis reaction Methods 0.000 claims description 10
• 239000003039 volatile agent Substances 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• KVSMPYHREBMONS-UHFFFAOYSA-N 1-ethyl-1$l^{5}-phosphinane 1-oxide Chemical compound CCP1(=O)CCCCC1 KVSMPYHREBMONS-UHFFFAOYSA-N 0.000 claims description 8
• ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 claims description 8
• KAIRZPVWWIMPFT-UHFFFAOYSA-N 3-piperidin-4-yl-1H-indole Chemical class C1CNCCC1C1=CNC2=CC=CC=C12 KAIRZPVWWIMPFT-UHFFFAOYSA-N 0.000 claims description 8
• NFMSZJSCUCJVCH-UHFFFAOYSA-N 4-(5-chloro-1-benzothiophen-3-yl)-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CSC2=CC=C(Cl)C=C12 NFMSZJSCUCJVCH-UHFFFAOYSA-N 0.000 claims description 8
• SNYURIHMNFPQFL-UHFFFAOYSA-N 5-chloro-1-benzothiophene Chemical compound ClC1=CC=C2SC=CC2=C1 SNYURIHMNFPQFL-UHFFFAOYSA-N 0.000 claims description 8
• DQGWEDRPBNHZDE-UHFFFAOYSA-N 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1C1=CCNCC1 DQGWEDRPBNHZDE-UHFFFAOYSA-N 0.000 claims description 8
• 210000004556 Brain Anatomy 0.000 claims description 8
• 206010012378 Depression Diseases 0.000 claims description 8
• XOTGOPCBFKMOEQ-UHFFFAOYSA-N OC(=O)C(O)=O.C1=CC=C2SC=CC2=C1 Chemical compound OC(=O)C(O)=O.C1=CC=C2SC=CC2=C1 XOTGOPCBFKMOEQ-UHFFFAOYSA-N 0.000 claims description 8
• JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
• 239000008346 aqueous phase Substances 0.000 claims description 8
• 230000015572 biosynthetic process Effects 0.000 claims description 8
• 230000002490 cerebral Effects 0.000 claims description 8
• 230000000694 effects Effects 0.000 claims description 8
• KZMGYPLQYOPHEL-UHFFFAOYSA-N ethoxyethane;trifluoroborane Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 239000004615 ingredient Substances 0.000 claims description 8
• 229910052740 iodine Inorganic materials 0.000 claims description 8
• 229910052744 lithium Inorganic materials 0.000 claims description 8
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 239000012299 nitrogen atmosphere Substances 0.000 claims description 8
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
• 238000000746 purification Methods 0.000 claims description 8
• 238000007363 ring formation reaction Methods 0.000 claims description 8
• 238000010898 silica gel chromatography Methods 0.000 claims description 8
• 239000000725 suspension Substances 0.000 claims description 8
• 230000002194 synthesizing Effects 0.000 claims description 8
• 150000003509 tertiary alcohols Chemical class 0.000 claims description 8
• 238000002560 therapeutic procedure Methods 0.000 claims description 8
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 7
• 230000003287 optical Effects 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• DZVADPDEULVABU-UHFFFAOYSA-N 1-(1-benzothiophen-2-yl)piperidine Chemical class C1CCCCN1C1=CC2=CC=CC=C2S1 DZVADPDEULVABU-UHFFFAOYSA-N 0.000 claims description 6
• SWZALEXJVROXGX-UHFFFAOYSA-N 1-benzothiophene;phosphoric acid Chemical compound OP(O)(O)=O.C1=CC=C2SC=CC2=C1 SWZALEXJVROXGX-UHFFFAOYSA-N 0.000 claims description 6
• SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 claims description 6
• WNJUSZXHGGTZJQ-UHFFFAOYSA-N 4-(cyclopropylmethoxy)-1H-indole Chemical compound C=1C=CC=2NC=CC=2C=1OCC1CC1 WNJUSZXHGGTZJQ-UHFFFAOYSA-N 0.000 claims description 6
• YTYIMDRWPTUAHP-UHFFFAOYSA-N 6-Chloroindole Chemical compound ClC1=CC=C2C=CNC2=C1 YTYIMDRWPTUAHP-UHFFFAOYSA-N 0.000 claims description 6
• APAMKXUATGRDBB-UHFFFAOYSA-N 6-chloro-1-benzothiophene Chemical compound ClC1=CC=C2C=CSC2=C1 APAMKXUATGRDBB-UHFFFAOYSA-N 0.000 claims description 6
• UUUZYHSWCJGNBA-UHFFFAOYSA-N 6-chloro-3-piperidin-4-yl-1H-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1C1CCNCC1 UUUZYHSWCJGNBA-UHFFFAOYSA-N 0.000 claims description 6
• 210000004369 Blood Anatomy 0.000 claims description 6
• 241000282412 Homo Species 0.000 claims description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
• 239000002168 alkylating agent Substances 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims description 6
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
• 239000008280 blood Substances 0.000 claims description 6
• 239000003153 chemical reaction reagent Substances 0.000 claims description 6
• 239000000460 chlorine Substances 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
• 238000006114 decarboxylation reaction Methods 0.000 claims description 6
• 239000006185 dispersion Substances 0.000 claims description 6
• 239000000284 extract Substances 0.000 claims description 6
• 238000000605 extraction Methods 0.000 claims description 6
• 239000007903 gelatin capsule Substances 0.000 claims description 6
• 238000006460 hydrolysis reaction Methods 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 239000000543 intermediate Substances 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
• KRRAZMUPVIGDCU-UHFFFAOYSA-N methyl 1-benzothiophene-2-carboxylate Chemical compound C1=CC=C2SC(C(=O)OC)=CC2=C1 KRRAZMUPVIGDCU-UHFFFAOYSA-N 0.000 claims description 6
• MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 claims description 6
• 230000001537 neural Effects 0.000 claims description 6
• 239000002245 particle Substances 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 229920000137 polyphosphoric acid Polymers 0.000 claims description 6
• 238000001953 recrystallisation Methods 0.000 claims description 6
• 239000001187 sodium carbonate Substances 0.000 claims description 6
• 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• CDEKBCJJKMKRFT-UHFFFAOYSA-N tert-butyl 4-(6-chloro-1-benzothiophen-2-yl)-4-hydroxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(O)C1=CC2=CC=C(Cl)C=C2S1 CDEKBCJJKMKRFT-UHFFFAOYSA-N 0.000 claims description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 6
• 239000003021 water soluble solvent Substances 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• ZKSGPMLZIPWJAF-ODZAUARKSA-N (Z)-but-2-enedioic acid;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)\C=C/C(O)=O ZKSGPMLZIPWJAF-ODZAUARKSA-N 0.000 claims description 4
• DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
• AMFUNLJGQHGZDN-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3,6-dihydro-2H-pyridine Chemical class C1C=CCCN1C1=CSC2=CC=CC=C12 AMFUNLJGQHGZDN-UHFFFAOYSA-N 0.000 claims description 4
• VDWLCYCWLIKWBV-UHFFFAOYSA-N 1-(benzenesulfonyl)indole Chemical compound C1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 VDWLCYCWLIKWBV-UHFFFAOYSA-N 0.000 claims description 4
• YHYLDEVWYOFIJK-UHFFFAOYSA-N 1H-indole-5-carbonitrile Chemical compound N#CC1=CC=C2NC=CC2=C1 YHYLDEVWYOFIJK-UHFFFAOYSA-N 0.000 claims description 4
• ZZXDRXVIRVJQBT-UHFFFAOYSA-M 2,3-dimethylbenzenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 claims description 4
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