NO331805B1 - N-arylsulfonyl-3-aminoalkoksyindoler - Google Patents

Info

Publication number

NO331805B1

NO331805B1 NO20052825A NO20052825A NO331805B1 NO 331805 B1 NO331805 B1 NO 331805B1 NO 20052825 A NO20052825 A NO 20052825A NO 20052825 A NO20052825 A NO 20052825A NO 331805 B1 NO331805 B1 NO 331805B1

Authority

NO

Norway

Prior art keywords

indol

yloxy

ethyl

dimethylamine

bromo

Prior art date

2002-11-28

Links

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• 150000001875 compounds Chemical class 0.000 claims abstract description 181
• 238000000034 method Methods 0.000 claims abstract description 131
• 150000003839 salts Chemical class 0.000 claims abstract description 54
• 238000002360 preparation method Methods 0.000 claims abstract description 21
• 239000012453 solvate Substances 0.000 claims abstract description 20
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 9
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 879
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 401
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical group C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 57
• -1 sulfonyloxy Chemical group 0.000 claims description 53
• 238000006243 chemical reaction Methods 0.000 claims description 45
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
• 239000000203 mixture Substances 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 239000000243 solution Substances 0.000 claims description 11
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 239000000460 chlorine Substances 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 9
• 108050009605 Melatonin receptor Chemical group 0.000 claims description 8
• 102000001419 Melatonin receptor Human genes 0.000 claims description 8
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 229910052744 lithium Inorganic materials 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 239000000825 pharmaceutical preparation 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
• 239000002243 precursor Substances 0.000 claims description 6
• 125000006239 protecting group Chemical group 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
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• PRUCGZIRLHZBSV-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5-bromoindol-3-yl]oxy-n,n-dimethylethanamine Chemical compound C12=CC=C(Br)C=C2C(OCCN(C)C)=CN1S(=O)(=O)C1=CC=CC=C1 PRUCGZIRLHZBSV-UHFFFAOYSA-N 0.000 claims description 4
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• 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 4
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• OAXFDZHGJIJOSH-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5-chloro-2-phenylindol-3-yl]oxy-n,n-dimethylethanamine Chemical compound C=1C=CC=CC=1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(OCCN(C)C)=C1C1=CC=CC=C1 OAXFDZHGJIJOSH-UHFFFAOYSA-N 0.000 claims description 3
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• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
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• XUSDOKWUKUREPG-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5,7-dibromo-2-phenylindol-3-yl]oxy-n,n-dimethylethanamine Chemical compound C=1C=CC=CC=1S(=O)(=O)N1C2=C(Br)C=C(Br)C=C2C(OCCN(C)C)=C1C1=CC=CC=C1 XUSDOKWUKUREPG-UHFFFAOYSA-N 0.000 claims description 2
• JJZMRZHOFDURJI-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5,7-dibromoindol-3-yl]oxy-n,n-dimethylethanamine Chemical compound C12=C(Br)C=C(Br)C=C2C(OCCN(C)C)=CN1S(=O)(=O)C1=CC=CC=C1 JJZMRZHOFDURJI-UHFFFAOYSA-N 0.000 claims description 2
• WSMSZDFVZZEPME-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5,7-dichloro-2-methylindol-3-yl]oxy-n,n-dimethylethanamine Chemical compound C12=C(Cl)C=C(Cl)C=C2C(OCCN(C)C)=C(C)N1S(=O)(=O)C1=CC=CC=C1 WSMSZDFVZZEPME-UHFFFAOYSA-N 0.000 claims description 2
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• FMRNYLJYBBHMQY-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5-bromo-2-methylindol-3-yl]oxy-n,n-dimethylethanamine Chemical compound C12=CC=C(Br)C=C2C(OCCN(C)C)=C(C)N1S(=O)(=O)C1=CC=CC=C1 FMRNYLJYBBHMQY-UHFFFAOYSA-N 0.000 claims description 2
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