NO910187L - Fremgangsmaate for fremstilling av indolsubstituerte, heteroaromatiske femringforbindelser. - Google Patents

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Publication number

NO910187L

NO910187L NO91910187A NO910187A NO910187L NO 910187 L NO910187 L NO 910187L NO 91910187 A NO91910187 A NO 91910187A NO 910187 A NO910187 A NO 910187A NO 910187 L NO910187 L NO 910187L

Authority

NO

Norway

Prior art keywords

indol

ethylamine

oxadiazol

dimethyl

ylmethyl

Prior art date

1990-01-17

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• 238000000034 method Methods 0.000 title claims description 61
• 238000002360 preparation method Methods 0.000 title claims description 23
• VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical class OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 title 1
• 239000000556 agonist Substances 0.000 claims abstract description 10
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 290
• 150000001875 compounds Chemical class 0.000 claims description 104
• 150000003839 salts Chemical class 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 239000001257 hydrogen Substances 0.000 claims description 46
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 150000002430 hydrocarbons Chemical class 0.000 claims description 20
• 239000004215 Carbon black (E152) Substances 0.000 claims description 18
• 229930195733 hydrocarbon Natural products 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• 239000001301 oxygen Substances 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 239000005864 Sulphur Substances 0.000 claims description 13
• 238000006243 chemical reaction Methods 0.000 claims description 13
• 239000000651 prodrug Substances 0.000 claims description 13
• 229940002612 prodrug Drugs 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 239000003153 chemical reaction reagent Substances 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 150000001450 anions Chemical class 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 238000010561 standard procedure Methods 0.000 claims description 7
• 239000002243 precursor Substances 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 4
• LUPGHCUZARGGAG-UHFFFAOYSA-N 5-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]-1,2,4-oxadiazol-3-amine Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(C=3ON=C(N)N=3)C=C12 LUPGHCUZARGGAG-UHFFFAOYSA-N 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 238000007126 N-alkylation reaction Methods 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• CQXMPRCDEFWGEN-UHFFFAOYSA-N n-[4-[[5-[[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]methyl]phenyl]methanesulfonamide Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2CC1=NC(CC=2C=CC(NS(C)(=O)=O)=CC=2)=NO1 CQXMPRCDEFWGEN-UHFFFAOYSA-N 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• SFVYCZXNJHFLNP-UHFFFAOYSA-N 5-[[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-amine Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2CC1=NC(N)=NO1 SFVYCZXNJHFLNP-UHFFFAOYSA-N 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 150000002825 nitriles Chemical class 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 239000011593 sulfur Chemical group 0.000 claims description 3
• MPSSFKDXUNOCMC-UHFFFAOYSA-N 1-[4-[5-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]phenyl]-n-methylmethanesulfonamide Chemical compound C1=CC(CS(=O)(=O)NC)=CC=C1C1=NOC(CC=2C=C3C(CCN(C)C)=CNC3=CC=2)=N1 MPSSFKDXUNOCMC-UHFFFAOYSA-N 0.000 claims description 2
• VOQRRSFSAOOBOA-UHFFFAOYSA-N 1-[4-[5-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]piperazin-1-yl]ethanone Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC(ON=1)=NC=1N1CCN(C(C)=O)CC1 VOQRRSFSAOOBOA-UHFFFAOYSA-N 0.000 claims description 2
• IMBUWDPVLHNYMC-UHFFFAOYSA-N 1-tert-butyl-3-[2-[5-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]ethyl]urea Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC1=NC(CCNC(=O)NC(C)(C)C)=NO1 IMBUWDPVLHNYMC-UHFFFAOYSA-N 0.000 claims description 2
• PGGBQIXTFVYDAU-UHFFFAOYSA-N 2-[5-(3-benzyl-1,2,4-oxadiazol-5-yl)-1h-indol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1C(ON=1)=NC=1CC1=CC=CC=C1 PGGBQIXTFVYDAU-UHFFFAOYSA-N 0.000 claims description 2
• LSUAPUGYEULDQN-UHFFFAOYSA-N 2-[5-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1C(ON=1)=NC=1C1CC1 LSUAPUGYEULDQN-UHFFFAOYSA-N 0.000 claims description 2
• RGZGVSMFNKBYQY-UHFFFAOYSA-N 2-[5-(3-ethyl-1,2,4-oxadiazol-5-yl)-1h-indol-3-yl]ethanamine Chemical compound CCC1=NOC(C=2C=C3C(CCN)=CNC3=CC=2)=N1 RGZGVSMFNKBYQY-UHFFFAOYSA-N 0.000 claims description 2
• FDPKHZFSVDEEFR-UHFFFAOYSA-N 2-[5-(3-phenyl-1,2,4-oxadiazol-5-yl)-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1C(ON=1)=NC=1C1=CC=CC=C1 FDPKHZFSVDEEFR-UHFFFAOYSA-N 0.000 claims description 2
• PKBMHXUBNRYPMY-UHFFFAOYSA-N 2-[5-(5-benzyl-1,2,4-oxadiazol-3-yl)-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1C(N=1)=NOC=1CC1=CC=CC=C1 PKBMHXUBNRYPMY-UHFFFAOYSA-N 0.000 claims description 2
• CXOIDKMODXFHCK-UHFFFAOYSA-N 2-[5-(5-methyl-1,2,4-oxadiazol-3-yl)-1h-indol-3-yl]ethanamine Chemical compound O1C(C)=NC(C=2C=C3C(CCN)=CNC3=CC=2)=N1 CXOIDKMODXFHCK-UHFFFAOYSA-N 0.000 claims description 2
• NAWLGGCQEZUAJT-UHFFFAOYSA-N 2-[5-[(3-benzyl-1,2,4-oxadiazol-5-yl)methyl]-1h-indol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC(ON=1)=NC=1CC1=CC=CC=C1 NAWLGGCQEZUAJT-UHFFFAOYSA-N 0.000 claims description 2
• NHIRYTRRCNWYFT-UHFFFAOYSA-N 2-[5-[(3-benzyl-1,2,4-oxadiazol-5-yl)methyl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1CC(ON=1)=NC=1CC1=CC=CC=C1 NHIRYTRRCNWYFT-UHFFFAOYSA-N 0.000 claims description 2
• PHNPQGKBBZNFFK-UHFFFAOYSA-N 2-[5-[(3-naphthalen-1-yl-1,2,4-oxadiazol-5-yl)methyl]-1h-indol-3-yl]ethanamine Chemical compound C1=CC=C2C(C=3N=C(ON=3)CC3=CC=C4NC=C(C4=C3)CCN)=CC=CC2=C1 PHNPQGKBBZNFFK-UHFFFAOYSA-N 0.000 claims description 2
• DUCJXOYLGYOOQB-UHFFFAOYSA-N 2-[5-[(3-phenyl-1,2,4-oxadiazol-5-yl)methyl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1CC(ON=1)=NC=1C1=CC=CC=C1 DUCJXOYLGYOOQB-UHFFFAOYSA-N 0.000 claims description 2
• LCMKXAZDWQVTEJ-UHFFFAOYSA-N 2-[5-[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]-1h-indol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC(N=1)=NOC=1CC1=CC=CC=C1 LCMKXAZDWQVTEJ-UHFFFAOYSA-N 0.000 claims description 2
• IEJZWIUEFHBSOU-UHFFFAOYSA-N 2-[5-[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1CC(N=1)=NOC=1CC1=CC=CC=C1 IEJZWIUEFHBSOU-UHFFFAOYSA-N 0.000 claims description 2
• FEBZQFFWELBCOG-UHFFFAOYSA-N 2-[5-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-1h-indol-3-yl]ethanamine Chemical compound O1C(C)=NC(CC=2C=C3C(CCN)=CNC3=CC=2)=N1 FEBZQFFWELBCOG-UHFFFAOYSA-N 0.000 claims description 2
• KYUWHJMADOFUBT-UHFFFAOYSA-N 2-[5-[2-(3-benzyl-1,2,4-oxadiazol-5-yl)ethyl]-1h-indol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CCC(ON=1)=NC=1CC1=CC=CC=C1 KYUWHJMADOFUBT-UHFFFAOYSA-N 0.000 claims description 2
• SCFZGOGBRPRNPV-UHFFFAOYSA-N 2-[5-[2-(3-benzyl-1,2,4-oxadiazol-5-yl)ethyl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1CCC(ON=1)=NC=1CC1=CC=CC=C1 SCFZGOGBRPRNPV-UHFFFAOYSA-N 0.000 claims description 2
• WBZVRZYJUXWCRS-UHFFFAOYSA-N 2-[5-[2-[3-[(4-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]ethyl]-1h-indol-3-yl]ethanamine Chemical compound C1=CC(OC)=CC=C1CC1=NOC(CCC=2C=C3C(CCN)=CNC3=CC=2)=N1 WBZVRZYJUXWCRS-UHFFFAOYSA-N 0.000 claims description 2
• OVCUAXXAZOYIFP-UHFFFAOYSA-N 2-[5-[3-(2-phenylethyl)-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1C(ON=1)=NC=1CCC1=CC=CC=C1 OVCUAXXAZOYIFP-UHFFFAOYSA-N 0.000 claims description 2
• JTBDYCCVUAQYMO-UHFFFAOYSA-N 2-[5-[3-(3-benzyl-1,2,4-oxadiazol-5-yl)propyl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1CCCC(ON=1)=NC=1CC1=CC=CC=C1 JTBDYCCVUAQYMO-UHFFFAOYSA-N 0.000 claims description 2
• HSJQSSUOMJZTMK-UHFFFAOYSA-N 2-[5-[3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)propyl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1CCCC(ON=1)=NC=1C1CC1 HSJQSSUOMJZTMK-UHFFFAOYSA-N 0.000 claims description 2
• FZVHHUSZLLUIQC-UHFFFAOYSA-N 2-[5-[3-(3-methyl-1,2,4-oxadiazol-5-yl)propyl]-1h-indol-3-yl]ethanamine Chemical compound CC1=NOC(CCCC=2C=C3C(CCN)=CNC3=CC=2)=N1 FZVHHUSZLLUIQC-UHFFFAOYSA-N 0.000 claims description 2
• NJDHGOXGGNXAKI-UHFFFAOYSA-N 2-[5-[3-(3-phenylpropyl)-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1C(ON=1)=NC=1CCCC1=CC=CC=C1 NJDHGOXGGNXAKI-UHFFFAOYSA-N 0.000 claims description 2
• NPFRJMBPAZUERU-UHFFFAOYSA-N 2-[5-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1C1=NC(CN)=NO1 NPFRJMBPAZUERU-UHFFFAOYSA-N 0.000 claims description 2
• ZBVQOYFWQDPVBU-UHFFFAOYSA-N 2-[5-[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]ethanamine Chemical compound COCC1=NOC(C=2C=C3C(CCN)=CNC3=CC=2)=N1 ZBVQOYFWQDPVBU-UHFFFAOYSA-N 0.000 claims description 2
• YSBPVPHNOKZUKE-UHFFFAOYSA-N 2-[5-[3-[(2-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]-n,n-dimethylethanamine Chemical compound COC1=CC=CC=C1CC1=NOC(C=2C=C3C(CCN(C)C)=CNC3=CC=2)=N1 YSBPVPHNOKZUKE-UHFFFAOYSA-N 0.000 claims description 2
• TWZLBEKNARALNH-UHFFFAOYSA-N 2-[5-[3-[(2-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]ethanamine Chemical compound COC1=CC=CC=C1CC1=NOC(C=2C=C3C(CCN)=CNC3=CC=2)=N1 TWZLBEKNARALNH-UHFFFAOYSA-N 0.000 claims description 2
• XYSVDZDGDYOEQP-UHFFFAOYSA-N 2-[5-[3-[(3-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]ethanamine Chemical compound COC1=CC=CC(CC=2N=C(ON=2)C=2C=C3C(CCN)=CNC3=CC=2)=C1 XYSVDZDGDYOEQP-UHFFFAOYSA-N 0.000 claims description 2
• LJFAPKDDNIXRTD-UHFFFAOYSA-N 2-[5-[3-[(4-methylsulfonylphenyl)methyl]-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]ethanamine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC1=NOC(C=2C=C3C(CCN)=CNC3=CC=2)=N1 LJFAPKDDNIXRTD-UHFFFAOYSA-N 0.000 claims description 2
• NISBLVDKMALBFA-UHFFFAOYSA-N 2-[5-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]-1,2,4-oxadiazol-3-yl]ethanamine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1C1=NC(CCN)=NO1 NISBLVDKMALBFA-UHFFFAOYSA-N 0.000 claims description 2
• MVCDNIJSCRIQST-UHFFFAOYSA-N 2-[5-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]-1,2,4-oxadiazol-3-yl]ethylurea Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1C1=NC(CCNC(N)=O)=NO1 MVCDNIJSCRIQST-UHFFFAOYSA-N 0.000 claims description 2
• RJQWPRYMOKNGFR-UHFFFAOYSA-N 2-[5-[3-[[4-(trifluoromethyl)phenyl]methyl]-1,2,4-oxadiazol-5-yl]-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=CNC2=CC=C1C(ON=1)=NC=1CC1=CC=C(C(F)(F)F)C=C1 RJQWPRYMOKNGFR-UHFFFAOYSA-N 0.000 claims description 2
• AWKHPNLMHRTDEQ-UHFFFAOYSA-N 2-[5-[[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]methyl]-1h-indol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC1=NC(CN)=NO1 AWKHPNLMHRTDEQ-UHFFFAOYSA-N 0.000 claims description 2
• NROOPDGYHXQHJT-UHFFFAOYSA-N 2-[5-[[3-[(2-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]-1h-indol-3-yl]ethanamine Chemical compound COC1=CC=CC=C1CC1=NOC(CC=2C=C3C(CCN)=CNC3=CC=2)=N1 NROOPDGYHXQHJT-UHFFFAOYSA-N 0.000 claims description 2
• JCZWGZKYZYBIIG-UHFFFAOYSA-N 2-[5-[[3-[(6-methoxypyridin-3-yl)methyl]-1,2,4-oxadiazol-5-yl]methyl]-1h-indol-3-yl]-n,n-dimethylethanamine Chemical compound C1=NC(OC)=CC=C1CC1=NOC(CC=2C=C3C(CCN(C)C)=CNC3=CC=2)=N1 JCZWGZKYZYBIIG-UHFFFAOYSA-N 0.000 claims description 2
• KFICIUZZUVCGKV-UHFFFAOYSA-N 2-[5-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]acetamide Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC1=NC(CC(N)=O)=NO1 KFICIUZZUVCGKV-UHFFFAOYSA-N 0.000 claims description 2
• QPFQAMAECLOAMI-UHFFFAOYSA-N 2-[5-[[3-[4-(benzenesulfonyl)piperazin-1-yl]-1,2,4-oxadiazol-5-yl]methyl]-1h-indol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC(ON=1)=NC=1N(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 QPFQAMAECLOAMI-UHFFFAOYSA-N 0.000 claims description 2
• PRTCSIDNPRTJHA-UHFFFAOYSA-N 4-[5-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=NOC(CC=2C=C3C(CCN(C)C)=CNC3=CC=2)=N1 PRTCSIDNPRTJHA-UHFFFAOYSA-N 0.000 claims description 2
• SEQRRDDBAQJBTP-UHFFFAOYSA-N 4-[5-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]-n-methylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)NC)CCN1C1=NOC(CC=2C=C3C(CCN(C)C)=CNC3=CC=2)=N1 SEQRRDDBAQJBTP-UHFFFAOYSA-N 0.000 claims description 2
• PXRPVIKQMBGGBX-UHFFFAOYSA-N 4-[5-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]benzamide Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC(ON=1)=NC=1C1=CC=C(C(N)=O)C=C1 PXRPVIKQMBGGBX-UHFFFAOYSA-N 0.000 claims description 2
• KPULPRRFVSBRHP-UHFFFAOYSA-N 4-[[5-[3-(2-aminoethyl)-1h-indol-5-yl]-1,2,4-oxadiazol-3-yl]methyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1CC1=NOC(C=2C=C3C(CCN)=CNC3=CC=2)=N1 KPULPRRFVSBRHP-UHFFFAOYSA-N 0.000 claims description 2
• HUZDZSZTHSEWGI-UHFFFAOYSA-N 4-[[5-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]-1,2,4-oxadiazol-3-yl]methyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1CC1=NOC(C=2C=C3C(CCN(C)C)=CNC3=CC=2)=N1 HUZDZSZTHSEWGI-UHFFFAOYSA-N 0.000 claims description 2
• JUIAOPBIMMONAG-UHFFFAOYSA-N 4-[[5-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]methyl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1CC1=NOC(CC=2C=C3C(CCN(C)C)=CNC3=CC=2)=N1 JUIAOPBIMMONAG-UHFFFAOYSA-N 0.000 claims description 2
• RZROEUJADIXUOQ-UHFFFAOYSA-N 4-[[5-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,2,4-oxadiazol-3-yl]methyl]benzamide Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC(ON=1)=NC=1CC1=CC=C(C(N)=O)C=C1 RZROEUJADIXUOQ-UHFFFAOYSA-N 0.000 claims description 2
• QMDXYKSJNYUFML-UHFFFAOYSA-N 5-[2-[3-(2-aminoethyl)-1h-indol-5-yl]ethyl]-n,n-dimethyl-1,2,4-oxadiazol-3-amine Chemical compound CN(C)C1=NOC(CCC=2C=C3C(CCN)=CNC3=CC=2)=N1 QMDXYKSJNYUFML-UHFFFAOYSA-N 0.000 claims description 2
• CVSXIEGQYNXATH-UHFFFAOYSA-N 5-[2-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]ethyl]-1,2,4-oxadiazol-3-amine Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CCC1=NC(N)=NO1 CVSXIEGQYNXATH-UHFFFAOYSA-N 0.000 claims description 2
• AZPGZTOVCHWLMC-UHFFFAOYSA-N 5-[3-(2-aminoethyl)-1h-indol-5-yl]-1,2,4-oxadiazol-3-amine Chemical compound C1=C2C(CCN)=CNC2=CC=C1C1=NC(N)=NO1 AZPGZTOVCHWLMC-UHFFFAOYSA-N 0.000 claims description 2
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