CA2253941A1 - Derives de la thiophenetryptamine et de la furanetryptamine - Google Patents
Derives de la thiophenetryptamine et de la furanetryptamine Download PDFInfo
- Publication number
- CA2253941A1 CA2253941A1 CA002253941A CA2253941A CA2253941A1 CA 2253941 A1 CA2253941 A1 CA 2253941A1 CA 002253941 A CA002253941 A CA 002253941A CA 2253941 A CA2253941 A CA 2253941A CA 2253941 A1 CA2253941 A1 CA 2253941A1
- Authority
- CA
- Canada
- Prior art keywords
- indole
- group
- thienyl
- substituted
- compound according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- JQUVCSIKDFMPBC-UHFFFAOYSA-N NCCC1=CNC2=CC=CC=C12.O1C=CC=C1.S1C=CC=C1 Chemical class NCCC1=CNC2=CC=CC=C12.O1C=CC=C1.S1C=CC=C1 JQUVCSIKDFMPBC-UHFFFAOYSA-N 0.000 title description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 10
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 119
- -1 N-substituted amino Chemical group 0.000 claims description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- 229930192474 thiophene Natural products 0.000 claims description 10
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
- 150000002475 indoles Chemical class 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000003577 thiophenes Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 150000002240 furans Chemical class 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- KULFBKTWESBCBG-UHFFFAOYSA-N 2-(5-thiophen-2-yl-1h-indol-3-yl)ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1C1=CC=CS1 KULFBKTWESBCBG-UHFFFAOYSA-N 0.000 claims description 2
- MVFRAIQWDQLKDO-UHFFFAOYSA-N 3-(1-methylpyrrolidin-3-yl)-5-thiophen-2-yl-1h-indole Chemical compound C1N(C)CCC1C1=CNC2=CC=C(C=3SC=CC=3)C=C12 MVFRAIQWDQLKDO-UHFFFAOYSA-N 0.000 claims description 2
- FEMUZGKPUZGQOO-UHFFFAOYSA-N 3-(1-methylpyrrolidin-3-yl)-5-thiophen-3-yl-1h-indole Chemical compound C1N(C)CCC1C1=CNC2=CC=C(C3=CSC=C3)C=C12 FEMUZGKPUZGQOO-UHFFFAOYSA-N 0.000 claims description 2
- LKKUCWJBPPXBRE-UHFFFAOYSA-N 3-[2-(2,5-dihydropyrrol-1-yl)ethyl]-5-thiophen-2-yl-1h-indole Chemical compound C1C=CCN1CCC(C1=C2)=CNC1=CC=C2C1=CC=CS1 LKKUCWJBPPXBRE-UHFFFAOYSA-N 0.000 claims description 2
- GRSKIEPWQOSYKY-UHFFFAOYSA-N 3-[2-(2,5-dimethylpyrrolidin-1-yl)ethyl]-5-thiophen-2-yl-1h-indole Chemical compound CC1CCC(C)N1CCC1=CNC2=CC=C(C=3SC=CC=3)C=C12 GRSKIEPWQOSYKY-UHFFFAOYSA-N 0.000 claims description 2
- PVZFDEHUGPXEHY-UHFFFAOYSA-N 3-[2-(2-methylpiperidin-1-yl)ethyl]-5-thiophen-2-yl-1h-indole Chemical compound CC1CCCCN1CCC1=CNC2=CC=C(C=3SC=CC=3)C=C12 PVZFDEHUGPXEHY-UHFFFAOYSA-N 0.000 claims description 2
- DRHJCTDOIDOKII-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)ethyl]-5-(furan-2-yl)-1h-indole Chemical compound C1CCN1CCC(C1=C2)=CNC1=CC=C2C1=CC=CO1 DRHJCTDOIDOKII-UHFFFAOYSA-N 0.000 claims description 2
- JPQGCWNLEUEINE-KRWDZBQOSA-N 3-[2-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]ethyl]-5-thiophen-2-yl-1h-indole Chemical compound COC[C@@H]1CCCN1CCC1=CNC2=CC=C(C=3SC=CC=3)C=C12 JPQGCWNLEUEINE-KRWDZBQOSA-N 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- WERVGTAJEZPWCD-UHFFFAOYSA-N 2-(1h-indol-3-yl)ethanamine;thiophene Chemical class C=1C=CSC=1.C1=CC=C2C(CCN)=CNC2=C1 WERVGTAJEZPWCD-UHFFFAOYSA-N 0.000 claims 10
- 150000003235 pyrrolidines Chemical class 0.000 claims 2
- QSSFRZLAEANSQV-UHFFFAOYSA-N 3-(2-piperidin-2-ylethyl)-5-thiophen-2-yl-1h-indole Chemical compound C1CCCNC1CCC(C1=C2)=CNC1=CC=C2C1=CC=CS1 QSSFRZLAEANSQV-UHFFFAOYSA-N 0.000 claims 1
- OYZHICOMJJQVRH-UHFFFAOYSA-N 3-(2-pyrrolidin-1-ylethyl)-5-thiophen-2-yl-1h-indole Chemical compound C1CCCN1CCC(C1=C2)=CNC1=CC=C2C1=CC=CS1 OYZHICOMJJQVRH-UHFFFAOYSA-N 0.000 claims 1
- QFGZJPXIMQJHHQ-UHFFFAOYSA-N 5-(furan-2-yl)-3-(2-pyrrolidin-1-ylethyl)-1h-indole Chemical compound C1CCCN1CCC(C1=C2)=CNC1=CC=C2C1=CC=CO1 QFGZJPXIMQJHHQ-UHFFFAOYSA-N 0.000 claims 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims 1
- 101000724739 Homo sapiens 5-hydroxytryptamine receptor 1D Proteins 0.000 claims 1
- VWTQLLNPBQMWDB-INIZCTEOSA-N [(2s)-1-[2-(5-thiophen-2-yl-1h-indol-3-yl)ethyl]pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1CCC1=CNC2=CC=C(C=3SC=CC=3)C=C12 VWTQLLNPBQMWDB-INIZCTEOSA-N 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 16
- 208000019695 Migraine disease Diseases 0.000 abstract description 4
- 206010027599 migraine Diseases 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 208000024891 symptom Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
- 239000000203 mixture Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 102000005962 receptors Human genes 0.000 description 16
- 108020003175 receptors Proteins 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 229910052786 argon Inorganic materials 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 229960004132 diethyl ether Drugs 0.000 description 10
- 239000012442 inert solvent Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 239000006188 syrup Substances 0.000 description 10
- 235000020357 syrup Nutrition 0.000 description 10
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 9
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000002243 precursor Substances 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- 150000004678 hydrides Chemical class 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 6
- 229960003708 sumatriptan Drugs 0.000 description 6
- 101710138068 5-hydroxytryptamine receptor 1D Proteins 0.000 description 5
- 102100027493 5-hydroxytryptamine receptor 1D Human genes 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006880 cross-coupling reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- VXWVFZFZYXOBTA-UHFFFAOYSA-N 5-bromo-1h-indole Chemical compound BrC1=CC=C2NC=CC2=C1 VXWVFZFZYXOBTA-UHFFFAOYSA-N 0.000 description 4
- ZZQOVQIQWNYKBJ-UHFFFAOYSA-N 5-bromo-3-(1-methylpyrrolidin-3-yl)-1h-indole Chemical compound C1N(C)CCC1C1=CNC2=CC=C(Br)C=C12 ZZQOVQIQWNYKBJ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229940076279 serotonin Drugs 0.000 description 4
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- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- JXGVXCZADZNAMJ-LLVKDONJSA-N (2r)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-LLVKDONJSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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- 238000011534 incubation Methods 0.000 description 3
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- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 3
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- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 2
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
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- 239000012448 Lithium borohydride Substances 0.000 description 2
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- PHLDAGMHTNKYED-UHFFFAOYSA-N [3-[2-(1,3-dioxoisoindol-2-yl)ethyl]-1h-indol-5-yl] trifluoromethanesulfonate Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC1=CNC2=CC=C(OS(=O)(=O)C(F)(F)F)C=C21 PHLDAGMHTNKYED-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000004479 aerosol dispenser Substances 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Dérivés de substitution en 5 de tryptamine, sélectifs vis-à-vis des récepteurs D1 de la 5-HT et, par conséquent, aptes à soulager les symptômes de la migraine. Les analogues sont représentés par la formule chimique générale (I), dans laquelle T représente un groupe thiophène avec substitution facultative, de formule (a), lié au noyau d'indole via sa position 2 ou 3, ou un groupe furane avec substitution facultative, de formule (b), lié au noyau d'indole via sa position 2 ou 3; X représente H, un alkyle C1-C4, un hydroxyalkyle C1-C4 ou un halogène en position 4 ou 5 du noyau; Y représente une liaison directe ou un groupe alkylène C1-C3 avec substitution facultative par un hydroxyle; enfin Z représente un groupe amino, amino avec substitution mono- ou di-N-alkyle inférieur, amino avec substitution par un alkyle inférieur, ou un groupe N-hétérocyclique choisi parmi la pyrrolidine, la pyrroline, l'azétidine et la pipéridine; le groupe N-hétérocyclique est avec substitution facultative par au moins un substituant choisi indépendamment parmi un alkyle inférieur, un alcoxy(inférieur)alkyle(inférieur) et un hydroxyalkyle(inférieur).
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/648,842 US5770742A (en) | 1996-05-16 | 1996-05-16 | Thiophene-tryptamine derivatives |
| US08/648,842 | 1996-05-16 | ||
| US83577897A | 1997-04-07 | 1997-04-07 | |
| US08/835,778 | 1997-04-07 | ||
| PCT/CA1997/000333 WO1997043281A1 (fr) | 1996-05-16 | 1997-05-16 | Derives de la thiophenetryptamine et de la furanetryptamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2253941A1 true CA2253941A1 (fr) | 1997-11-20 |
Family
ID=27095474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002253941A Abandoned CA2253941A1 (fr) | 1996-05-16 | 1997-05-16 | Derives de la thiophenetryptamine et de la furanetryptamine |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU2759597A (fr) |
| CA (1) | CA2253941A1 (fr) |
| WO (1) | WO1997043281A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9651534B1 (en) | 2015-12-02 | 2017-05-16 | Sani-Hawk Optical Solutions LLC | Optical chemical test systems and methods |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| US6251893B1 (en) * | 1998-06-15 | 2001-06-26 | Nps Allelix Corp. | Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity |
| US6562809B1 (en) * | 1998-09-18 | 2003-05-13 | Nps Allelix Corp. | 3-bicycloindole compounds |
| WO2004056769A2 (fr) | 2002-12-20 | 2004-07-08 | Ciba Specialty Chemicals Holding Inc. | Synthèse d'amines et intermédiaires pour cette synthèse |
| IL301066A (en) * | 2020-09-04 | 2023-05-01 | Gilgamesh Pharmaceuticals Inc | Azetidinyl tryptamines and methods for the treatment of psychiatric disorders |
| WO2025104490A1 (fr) * | 2023-11-14 | 2025-05-22 | Mindset Pharma Inc. | Dérivés d'indole utilisés en tant qu'agents sérotoninergiques utiles pour le traitement de troubles associés |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9208161D0 (en) * | 1992-04-14 | 1992-05-27 | Pfizer Ltd | Indoles |
| GB9313913D0 (en) * | 1993-07-06 | 1993-08-18 | Smithkline Beecham Plc | Novel compounds |
| JPH07271066A (ja) * | 1994-03-29 | 1995-10-20 | Mitsubishi Paper Mills Ltd | 電子写真感光体 |
| US5504101A (en) * | 1994-05-06 | 1996-04-02 | Allelix Biopharmaceuticals, Inc. | 5-HT-1D receptor ligands |
-
1997
- 1997-05-16 AU AU27595/97A patent/AU2759597A/en not_active Abandoned
- 1997-05-16 CA CA002253941A patent/CA2253941A1/fr not_active Abandoned
- 1997-05-16 WO PCT/CA1997/000333 patent/WO1997043281A1/fr not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9651534B1 (en) | 2015-12-02 | 2017-05-16 | Sani-Hawk Optical Solutions LLC | Optical chemical test systems and methods |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1997043281A1 (fr) | 1997-11-20 |
| AU2759597A (en) | 1997-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |