SK287273B6 - N-Substituované diazabicyklické zlúčeniny, farmaceutický prípravok s ich obsahom a ich použitie - Google Patents

Info

Publication number

SK287273B6

SK287273B6 SK1681-2002A SK16812002A SK287273B6 SK 287273 B6 SK287273 B6 SK 287273B6 SK 16812002 A SK16812002 A SK 16812002A SK 287273 B6 SK287273 B6 SK 287273B6

Authority

SK

Slovakia

Prior art keywords

pyridinyl

diazabicyclo

compound

covalent bond

pyrrole

Prior art date

2000-04-27

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 530
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
• 241000124008 Mammalia Species 0.000 claims abstract description 23
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 308
• -1 nitro, 5-tetrazolyl Chemical group 0.000 claims description 263
• 229910052739 hydrogen Inorganic materials 0.000 claims description 83
• 239000001257 hydrogen Substances 0.000 claims description 81
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 72
• 125000000217 alkyl group Chemical group 0.000 claims description 68
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
• 150000003839 salts Chemical class 0.000 claims description 38
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
• 239000003814 drug Substances 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 32
• 150000002367 halogens Chemical class 0.000 claims description 32
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 25
• 150000002431 hydrogen Chemical class 0.000 claims description 24
• 208000002193 Pain Diseases 0.000 claims description 23
• 230000036407 pain Effects 0.000 claims description 23
• 229940002612 prodrug Drugs 0.000 claims description 23
• 239000000651 prodrug Substances 0.000 claims description 23
• 208000035475 disorder Diseases 0.000 claims description 20
• 239000002858 neurotransmitter agent Substances 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 15
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 12
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
• 229960002715 nicotine Drugs 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 11
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 208000018737 Parkinson disease Diseases 0.000 claims description 7
• 230000001276 controlling effect Effects 0.000 claims description 7
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
• 125000004967 formylalkyl group Chemical group 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 230000001105 regulatory effect Effects 0.000 claims description 6
• RQYLYBKBTQKNMZ-GMSGAONNSA-N (1r,5s)-6-(5-azidopyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound [N-]=[N+]=NC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 RQYLYBKBTQKNMZ-GMSGAONNSA-N 0.000 claims description 5
• IQCDZVRYLPBQRD-CABZTGNLSA-N (1s,6r)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound COC1=CN=CC(N2[C@H]3CNCC[C@H]3C2)=C1 IQCDZVRYLPBQRD-CABZTGNLSA-N 0.000 claims description 5
• 208000000323 Tourette Syndrome Diseases 0.000 claims description 5
• 208000016620 Tourette disease Diseases 0.000 claims description 5
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
• 208000013403 hyperactivity Diseases 0.000 claims description 5
• 230000003957 neurotransmitter release Effects 0.000 claims description 5
• 201000000980 schizophrenia Diseases 0.000 claims description 5
• 208000011580 syndromic disease Diseases 0.000 claims description 5
• BWQKEWGYFNUHHX-VXNVDRBHSA-N (1r,5s)-6-(6-bromo-5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Br)C(OC)=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 BWQKEWGYFNUHHX-VXNVDRBHSA-N 0.000 claims description 4
• OSOHWFWLNDUPPP-WPRPVWTQSA-N (1s,6r)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CNCC[C@H]2C1 OSOHWFWLNDUPPP-WPRPVWTQSA-N 0.000 claims description 4
• NHOKDBHEVHBXTJ-ONGXEEELSA-N (1s,6r)-7-pyridin-3-yl-4,7-diazabicyclo[4.2.0]octane Chemical compound N1([C@H]2CNCC[C@H]2C1)C1=CC=CN=C1 NHOKDBHEVHBXTJ-ONGXEEELSA-N 0.000 claims description 4
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
• 230000005978 brain dysfunction Effects 0.000 claims description 4
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 4
• YHOMDZMYCWJHFA-WPRPVWTQSA-N (1s,6r)-4-(6-chloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NC[C@@H]2CC1 YHOMDZMYCWJHFA-WPRPVWTQSA-N 0.000 claims description 3
• FZHVWHFLHSHANF-SCZZXKLOSA-N (3ar,6ar)-1-(6-chloropyridin-3-yl)-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CNC[C@H]2CC1 FZHVWHFLHSHANF-SCZZXKLOSA-N 0.000 claims description 3
• KOMXDDRATCALPT-AOOOYVTPSA-N (3as,6ar)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound C([C@H]1CNC[C@H]1C1)N1C1=CC=CN=C1 KOMXDDRATCALPT-AOOOYVTPSA-N 0.000 claims description 3
• GPXAWLDGWSBLKM-MWLCHTKSSA-N 5-[(1r,5s)-3,6-diazabicyclo[3.2.0]heptan-6-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 GPXAWLDGWSBLKM-MWLCHTKSSA-N 0.000 claims description 3
• VUGNXGAJCUBYBO-DTORHVGOSA-N 5-[(3as,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl]pyridin-3-ol Chemical compound OC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 VUGNXGAJCUBYBO-DTORHVGOSA-N 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
• LVRYCPLQUQOATD-RKDXNWHRSA-N (1r,5r)-7-(6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1[C@@H]2CCN[C@@H]2C1 LVRYCPLQUQOATD-RKDXNWHRSA-N 0.000 claims description 2
• OGULMRQWNAMFPB-GMSGAONNSA-N (1r,5s)-6-(5-bromopyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound BrC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 OGULMRQWNAMFPB-GMSGAONNSA-N 0.000 claims description 2
• XHYQJTGLPJMMEB-PSASIEDQSA-N (1r,5s)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1([C@@H]2CNC[C@@H]2C1)C1=CC=CN=C1 XHYQJTGLPJMMEB-PSASIEDQSA-N 0.000 claims description 2
• RZYCOPGGQSSESS-CBAPKCEASA-N (1s,5r)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1[C@H]2CNC[C@H]2C1 RZYCOPGGQSSESS-CBAPKCEASA-N 0.000 claims description 2
• VXCWOKWPZDBULP-XVKPBYJWSA-N (1s,6r)-7-(5,6-dichloropyridin-3-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@H]3CNCC[C@H]3C2)=C1 VXCWOKWPZDBULP-XVKPBYJWSA-N 0.000 claims description 2
• ZJLSTXGOFNDPFN-YPMHNXCESA-N (3ar,6ar)-5-(5-ethenylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C=CC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 ZJLSTXGOFNDPFN-YPMHNXCESA-N 0.000 claims description 2
• SLNSBOHQJODUJZ-SCZZXKLOSA-N (3ar,6ar)-5-(6-bromo-5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Br)C(OC)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 SLNSBOHQJODUJZ-SCZZXKLOSA-N 0.000 claims description 2
• OHWQUEIYHPZQPN-TXEJJXNPSA-N (3ar,6as)-5-(5-propoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound CCCOC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 OHWQUEIYHPZQPN-TXEJJXNPSA-N 0.000 claims description 2
• QCAHYIYDXVYFOH-AOOOYVTPSA-N (3as,6ar)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound COC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 QCAHYIYDXVYFOH-AOOOYVTPSA-N 0.000 claims description 2
• SUMBPLBCXUNGMO-GZMMTYOYSA-N (3as,6as)-5-(5-bromopyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound BrC1=CN=CC(N2C[C@H]3NCC[C@H]3C2)=C1 SUMBPLBCXUNGMO-GZMMTYOYSA-N 0.000 claims description 2
• YSAVCILVSULFGD-JOYOIKCWSA-N (3as,6as)-5-(5-methoxypyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound COC1=CN=CC(N2C[C@H]3NCC[C@H]3C2)=C1 YSAVCILVSULFGD-JOYOIKCWSA-N 0.000 claims description 2
• HMWDILXJWAOEJT-GXSJLCMTSA-N (3as,6as)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@@H]1CCN[C@@H]1C1)N1C1=CC=CN=C1 HMWDILXJWAOEJT-GXSJLCMTSA-N 0.000 claims description 2
• YKOUMOZMCMIKMG-JQWIXIFHSA-N 5-[(1s,6r)-4,7-diazabicyclo[4.2.0]octan-7-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2[C@H]3CNCC[C@H]3C2)=C1 YKOUMOZMCMIKMG-JQWIXIFHSA-N 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
• IWMPNPIMHCIYMC-HZGVNTEJSA-N (1r,5s)-6-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 IWMPNPIMHCIYMC-HZGVNTEJSA-N 0.000 claims 2
• ZUQWAAYYWZDXPL-APPZFPTMSA-N (1r,5r)-3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NC[C@@H]2C1 ZUQWAAYYWZDXPL-APPZFPTMSA-N 0.000 claims 1
• XLWRHIFAGPGATJ-NXEZZACHSA-N (1r,5r)-7-pyridin-3-yl-4,7-diazabicyclo[3.2.0]heptane Chemical compound N1([C@@H]2CCN[C@@H]2C1)C1=CC=CN=C1 XLWRHIFAGPGATJ-NXEZZACHSA-N 0.000 claims 1
• CIYRARKCUJBDET-ZYHUDNBSSA-N (1r,5s)-6-(5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C#CC1=CN=CC(N2[C@@H]3CNC[C@@H]3C2)=C1 CIYRARKCUJBDET-ZYHUDNBSSA-N 0.000 claims 1
• RZYCOPGGQSSESS-VXNVDRBHSA-N (1r,5s)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound C1=NC(Cl)=CC=C1N1[C@@H]2CNC[C@@H]2C1 RZYCOPGGQSSESS-VXNVDRBHSA-N 0.000 claims 1
• IWMPNPIMHCIYMC-RCOVLWMOSA-N (1s,5r)-6-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane Chemical compound N1=C(Cl)C(Cl)=CC(N2[C@H]3CNC[C@H]3C2)=C1 IWMPNPIMHCIYMC-RCOVLWMOSA-N 0.000 claims 1
• NBPGBNNVEWLKEW-KOLCDFICSA-N (3ar,6ar)-1-pyridin-3-yl-3,3a,4,5,6,6a-hexahydro-2h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@@H]1CNC[C@@H]11)CN1C1=CC=CN=C1 NBPGBNNVEWLKEW-KOLCDFICSA-N 0.000 claims 1
• SUMBPLBCXUNGMO-KCJUWKMLSA-N (3ar,6ar)-5-(5-bromopyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound BrC1=CN=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 SUMBPLBCXUNGMO-KCJUWKMLSA-N 0.000 claims 1
• KEKVMZXOMNEOQP-KOLCDFICSA-N (3ar,6ar)-5-(6-bromo-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Br)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 KEKVMZXOMNEOQP-KOLCDFICSA-N 0.000 claims 1
• RUEPBFNTOSWZAB-KOLCDFICSA-N (3ar,6ar)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 RUEPBFNTOSWZAB-KOLCDFICSA-N 0.000 claims 1
• DQHQCRQWOJTKBG-SCZZXKLOSA-N (3ar,6ar)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C1=NC(Cl)=CC=C1N1C[C@@H]2NCC[C@@H]2C1 DQHQCRQWOJTKBG-SCZZXKLOSA-N 0.000 claims 1
• HMWDILXJWAOEJT-KOLCDFICSA-N (3ar,6ar)-5-pyridin-3-yl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound C([C@H]1CCN[C@H]1C1)N1C1=CC=CN=C1 HMWDILXJWAOEJT-KOLCDFICSA-N 0.000 claims 1
• GGWINWDBVWLKNK-AOOOYVTPSA-N (3ar,6as)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3CNC[C@H]3C2)=C1 GGWINWDBVWLKNK-AOOOYVTPSA-N 0.000 claims 1
• DEARFOHLLIJAOI-AOOOYVTPSA-N (3ar,6as)-5-[5-(2,2,2-trifluoroethoxy)pyridin-3-yl]-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound FC(F)(F)COC1=CN=CC(N2C[C@H]3CNC[C@H]3C2)=C1 DEARFOHLLIJAOI-AOOOYVTPSA-N 0.000 claims 1
• RUEPBFNTOSWZAB-GXSJLCMTSA-N (3as,6as)-5-(6-chloro-5-methylpyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrole Chemical compound N1=C(Cl)C(C)=CC(N2C[C@H]3NCC[C@H]3C2)=C1 RUEPBFNTOSWZAB-GXSJLCMTSA-N 0.000 claims 1
• KQMSAFWRVJCRPS-PSASIEDQSA-N 2-bromo-5-[(1r,5s)-3,6-diazabicyclo[3.2.0]heptan-6-yl]pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Br)=NC=C1N1[C@@H]2CNC[C@@H]2C1 KQMSAFWRVJCRPS-PSASIEDQSA-N 0.000 claims 1
• KLNHDAVAIWEDTG-BETUJISGSA-N 3-[(3ar,6as)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl]quinoline Chemical compound C1=CC=CC2=CC(N3C[C@H]4CNC[C@H]4C3)=CN=C21 KLNHDAVAIWEDTG-BETUJISGSA-N 0.000 claims 1
• 208000012902 Nervous system disease Diseases 0.000 claims 1
• 230000001668 ameliorated effect Effects 0.000 claims 1
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 190
• 230000005062 synaptic transmission Effects 0.000 abstract description 11
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 298
• CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 255
• 238000000034 method Methods 0.000 description 195
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 174
• 239000000047 product Substances 0.000 description 169
• 230000002829 reductive effect Effects 0.000 description 152
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 119
• 229910004298 SiO 2 Inorganic materials 0.000 description 111
• 238000004587 chromatography analysis Methods 0.000 description 110
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 107
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 106
• 235000019439 ethyl acetate Nutrition 0.000 description 104
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 98
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
• 239000007787 solid Substances 0.000 description 86
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 77
• 239000000243 solution Substances 0.000 description 69
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
• 235000019441 ethanol Nutrition 0.000 description 58
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
• 239000000706 filtrate Substances 0.000 description 55
• 239000003921 oil Substances 0.000 description 53
• 235000019198 oils Nutrition 0.000 description 53
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 49
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
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