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

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims description 313
• -1 2-methylphenoxy Chemical group 0.000 claims description 259
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 216
• 230000002829 reductive effect Effects 0.000 claims description 210
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 204
• 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
• 239000000203 mixture Substances 0.000 claims description 139
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 126
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 126
• 238000000034 method Methods 0.000 claims description 117
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 90
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 86
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 86
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 84
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 84
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 78
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 76
• 239000000047 product Substances 0.000 claims description 72
• 238000006243 chemical reaction Methods 0.000 claims description 64
• 229920006395 saturated elastomer Polymers 0.000 claims description 62
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate 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
• 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
• 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
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 44
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 44
• 238000002360 preparation method Methods 0.000 claims description 44
• 239000011780 sodium chloride Substances 0.000 claims description 44
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 42
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 40
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 40
• 238000011282 treatment Methods 0.000 claims description 40
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
• 239000003921 oil Substances 0.000 claims description 36
• SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 claims description 34
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 34
• 238000010992 reflux Methods 0.000 claims description 34
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 32
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 30
• 229940076279 serotonin Drugs 0.000 claims description 29
• 238000006297 dehydration reaction Methods 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000002904 solvent Substances 0.000 claims description 28
• 230000018044 dehydration Effects 0.000 claims description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
• VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-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
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 22
• 235000017557 sodium bicarbonate Nutrition 0.000 claims description 22
• 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 22
• 238000004587 chromatography analysis Methods 0.000 claims description 20
• 229940079593 drug Drugs 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 20
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 18
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 16
• 238000005984 hydrogenation reaction Methods 0.000 claims description 16
• 230000005764 inhibitory process Effects 0.000 claims description 16
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 16
• CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 238000009472 formulation Methods 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 14
• 230000002378 acidificating effect 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
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 239000003054 catalyst Substances 0.000 claims description 14
• 229960002464 fluoxetine Drugs 0.000 claims description 14
• 239000006260 foam Substances 0.000 claims description 14
• 239000000843 powder Substances 0.000 claims description 14
• 230000009467 reduction Effects 0.000 claims description 14
• 238000006722 reduction reaction Methods 0.000 claims description 14
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
• 125000005518 carboxamido group Chemical group 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
• 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
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
• 239000000908 ammonium hydroxide Substances 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
• 239000000706 filtrate Substances 0.000 claims description 12
• 238000001914 filtration Methods 0.000 claims description 12
• 239000003112 inhibitor Substances 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
• 239000000463 material Substances 0.000 claims description 12
• 239000007858 starting material Substances 0.000 claims description 12
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 10
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 10
• 238000002425 crystallisation Methods 0.000 claims description 10
• 230000008025 crystallization Effects 0.000 claims description 10
• 238000010511 deprotection reaction Methods 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 10
• 230000000694 effects Effects 0.000 claims description 10
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 10
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 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
• 239000012312 sodium hydride Substances 0.000 claims description 10
• 229910000104 sodium hydride Inorganic materials 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
• AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-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
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 8
• 208000020401 Depressive disease Diseases 0.000 claims description 8
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 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
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 239000008346 aqueous phase Substances 0.000 claims description 8
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
• 230000015572 biosynthetic process Effects 0.000 claims description 8
• 210000004556 brain Anatomy 0.000 claims description 8
• 230000002490 cerebral effect Effects 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
• 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
• 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
• 238000010561 standard procedure Methods 0.000 claims description 8
• 239000000725 suspension Substances 0.000 claims description 8
• 150000003509 tertiary alcohols Chemical class 0.000 claims description 8
• 238000002560 therapeutic procedure Methods 0.000 claims description 8
• 241000124008 Mammalia Species 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
• YWZYSNVYMLGLEU-UHFFFAOYSA-N 1-benzothiophene trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.S1C=CC2=C1C=CC=C2 YWZYSNVYMLGLEU-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
• YGYUMNQONHLLNC-UHFFFAOYSA-N 4-chloro-1-benzothiophene Chemical compound ClC1=CC=CC2=C1C=CS2 YGYUMNQONHLLNC-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
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
• JSZIVRJLGDGLHV-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)(=O)O.S1C=CC2=C1C=CC=C2 Chemical compound CC1=CC=C(C=C1)S(=O)(=O)O.S1C=CC2=C1C=CC=C2 JSZIVRJLGDGLHV-UHFFFAOYSA-N 0.000 claims description 6
• 241000282412 Homo Species 0.000 claims description 6
• 241001465754 Metazoa Species 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
• 229940124639 Selective inhibitor Drugs 0.000 claims description 6
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 6
• 239000002168 alkylating agent Substances 0.000 claims description 6
• 229940100198 alkylating agent Drugs 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 6
• 230000004888 barrier function Effects 0.000 claims description 6
• 230000008901 benefit Effects 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
• 210000004369 blood Anatomy 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
• 238000007596 consolidation process Methods 0.000 claims description 6
• 239000013078 crystal Substances 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
• 230000007062 hydrolysis Effects 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
• 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
• 230000003287 optical effect Effects 0.000 claims description 6
• 239000002245 particle Substances 0.000 claims description 6
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